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The imidyl compounds, according to the invention, of the formula I are suitable for the manufacture of polymers which can be crosslinked by light, which polymers can be, for example, polyesters, polyamides, polyamide-imides, polyimides, polyester-polyamides, polyester-amide-imides, polyethers, polyamines, polysaccharides and polysiloxanes. Polymers of this type are suitable for carrying out photochemical processes. Compared with known polymers, the polymers based on the imidyl compounds according to the invention have the advantage that they are photochemically substantially more sensitive. In addition, this sensitivity can also be further increased effectively by a combination with sensitisers.

The imidyl compounds, according to the invention, of the formula I are suitable for the manufacture of polymers which can be crosslinked by light, which polymers can be, for example, polyesters, polyamides, polyamide-imides, polyimides, polyester-polyamides, polyester-amide-imides, polyethers, polyamines, polysaccharides and polysiloxanes. Polymers of this type are suitable for carrying out photochemical processes. Compared with known polymers, the polymers based on the imidyl compounds according to the invention have the advantage that they are photochemically substantially more sensitive. In addition, this sensitivity can also be further increased effectively by a combination with sensitizers.

The invention relates to the manufacture of crystalline epoxide resins which exhibit a marked crystallite melt temperature. The formation of the crystallites is caused by molecule blocks which are derived from aliphatic polyester-polycarboxylic acids. According to the invention, two aliphatic polyester-polycarboxylic acids (A and B) are reacted under very specific quantitative conditions with epoxide compounds which contain at least 2 epoxide groups and optionally with curing agents. The polyester-polycarboxylic acids A are purely n-aliphatic in character, whereas the polyester-polycarboxylic acids B are not. They contain, for example, neopentyl radicals which are derived from neopentyl alcohol during the ester formation. These crystalline synthetic resins are particularly suitable for use as material for absorbing solar energy in solar energy collectors.

The invention relates to the manufacture of crystalline epoxide resins which have at least two crystallite melt temperatures. The cause of the crystallites are molecule blocks which are derived from aliphatic polyesterpolycarboxylic acids. According to the invention, at least two aliphatic polyester-polycarboxylic acids (D and E), which bear a special relation to each other in respect of the number of --CH.sub.2 groups in the primary chain member, are reacted under very specific quantitative conditions with epoxide compounds which contain at least 2 epoxide groups and optionally with curing agents. The synthetic resins thereby obtained are particularly suitable for use as storage material in latent heat accumulators.

Feeds and feed additives for domestic animals and productive animals, which feeds and feed additives contain 1 to 500 ppm of avilamycin.

Nickel complexes containing ortho- or para-hydroxybenzoate anions and a non-ionic amine ligand are valuable light-stabilizers for polymers, particularly for polyolefins. The complexes may also contain a second carboxylate anion, different from the benzoate anion, and in this case also the amine-free nickel compounds show a high stabilizing action.

A softening agent is provided which contains (a) a diester/amine adduct of the formula ##STR1## in which X.sub.1, X.sub.2 and X.sub.3 are --H, 1-4 C alkyl, 2-4 C hydroxyalkyl or hydroxyhalogenalkyl or ##STR2## Y.sub.1 is 1-4 C alkyl or ##STR3## R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are 12-22 C alkyl or alkenyl, A.sub.1 and A.sub.2 are 2-3 C alkylene or 2-hydroxy-n-propylene m, s, s' and s" are 1 or 2 and n is 1, 2, 3 or 4, and (b) a quaternary ammonium salt of the formula ##STR4## in which Q.sub.1 and T.sub.2 are --H, 1-8 C alkyl or 2-8 C alkenyl, Q.sub.2 is 1-8 C alkyl or 2-8 C alkenyl, Q.sub.3, T.sub.1 and T.sub.3 are 8-30 C alkyl or alkenyl, Q.sub.4 is 1-30 C alkyl or 2-30 C alkenyl and D.sub.1.sup..crclbar. and E.sub.1.sup..crclbar. are an anion imparting water-solubility or water-dispersability. These softening agent are valuable for use as after-rinse softeners and hair-conditioners.

An electrophotographic imaging process, wherein the electrically photosensitive particles for the image reproduction consist of a black pigment selected from the series of the anthraquinoid pigments which contain at least 2 anthraquinone radicals or at least 6 condensed rings, of the perylenetetracarboxylic diimides or of the metal complexes of the formula ##STR1## wherein A represents a nitrogen atom or the ##STR2## X represents a hydrogen or halogen atom or an alkyl group of 1 to 6 carbon atoms, Y represents a hydrogen or halogen atom, an alkyl, alkoxy or alkylsulphonyl group of 1 to 6 carbon atoms, a nitro or carbamoyl group, an alkylcarbamoyl or alkoxycarbonyl group of 2 to 6 carbon atoms or an arylcarbamoyl or aryloxycarbonyl group of 7 to 11 carbon atoms.

Bis-anthranilates of the formula ##STR1## or mixtures thereof, in which, in the formula, m and n are each 0 or a number from 1 to 5 and the sum of m and n must be at least 1, y is 0 or 1 and X is an alkylene radical having 1 to 8 C atoms, para- or meta-phenylene or para-cyclohexylene. The novel compounds are valuable chain extenders and crosslinking agents for the production of polyurethanes and polyurea resins and are also suitable as curing agents for epoxide resins.

Curable mixtures comprising a polyepoxide compound having on average more than one epoxide group per molecule and a 1,3-diaminopropane of the formula ##STR1## wherein R.sup.1 denotes hydrogen and R.sup.1, R.sup.2, R.sup.3 and R.sup.4 each denote an alkyl having 1 to 12 C atoms, a phenyl or a heterocyclic 5-membered or 6-membered radical, or wherein R.sup.1 and R.sup.2 together with the C atom in the .alpha.-position of the propylenediamine from a substituted or unsubstituted aliphatic 5-membered or 6-membered ring having at most 12 C atoms and R.sup.3 and R.sup.4 together with the two C atoms in the .alpha.-position and the .beta.-position of the propylenediamine form a substituted or unsubstituted aliphatic or N-heterocyclic 5-membered or 6-membered ring having at most 12 C atoms, said mixtures containing 0.5 to 1.5 equivalents of active hydrogen atoms, bonded to nitrogen, in the 1,3-diaminopropane per 1 equivalent of epoxide groups in the epoxide compound. The curable mixtures are valuable casting resins and adhesives and are suitable for the preparation of storable B-stage resins.

The imidyl compounds, according to the invention, of the formula I are suitable for the manufacture of polymers which can be crosslinked by light, which polymers can be, for example, polyesters, polyamides, polyamide-imides, polyimides, polyester-polyamides, polyester-amide-imides, polyethers, polyamines, polysaccharides and polysiloxanes. Polymers of this type are suitable for carrying out photochemical processes. Compared with known polymers, the polymers based on the imidyl compounds according to the invention have the advantage that they are photochemically substantially more sensitive. In addition, this sensitivity can also be further increased effectively by a combination with sensitizers.

The compositons of matter according to the invention consist of at least one polymeric compound and at least one compound of the formula I ##STR1## in which R is a divalent organic radical. The weight ratio of polymer to compound of the formula I is about 9:1 to 1:4. The compounds of the formula I and thus also the compositions of matter are photo-curable (-crosslinkable). They are superior to known systems in respect of heat stability and oxidation resistance, while possessing photosensitivity which is equally as good.

A process for producing paper or cardboard which is sized in the pulp with epoxide-amine-polyamide reaction products is disclosed. In this process there are added to the fibre suspension (A) at least one water-soluble, anionic, substantive direct dye and/or optical brightener, followed by (B) at least one water-soluble or water-dispersible salt of an epoxide-amine-polyamide reaction product, whereupon the fibre suspension is further processed into paper or into cardboard.

The invention relates to a process for the production of cured shaped articles based on epoxide resins, the compounds used as curing agents being derivatives of cyanoacetic acid, and to compositions for carrying out this process. Such compositions are used for the production of casting resins, laminating resins, lacquers, compression moulding compositions, fluidized-bed sinter powders, adhesives and glass fibre-reinforced plastics.

Microbicidally active compounds of the formula I ##STR1## wherein R.sub.1 represents alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms or halogen, R.sub.2 represents hydrogen, alkyl of 1 to 3 carbon atoms, alkoxy of 1 to 4 carbon atoms or halogen, R.sub.5 represents hydrogen, alkyl of 1 to 3 carbon atoms or halogen, R.sub.6 represents hydrogen or methyl, the total number of carbon atoms of the substituents R.sub.1, R.sub.2, R.sub.5 and R.sub.6 in the phenyl ring not exceeding 8, X represents --CH.sub.2 -- or ##STR2## R'.sub.3 represents --COOR' or ##STR3## wherein each of R', R" and R'" independently represents hydogen, methyl, or ethyl, and R.sub.4 represents alkyl of 1 to 6 carbon atoms, which is unsubstituted or substituted by cyano (--CN) or rhodano (--SCN), alkenyl of 2 to 5 carbon atoms or cycloalkyl of 3 to 7 carbon atoms.

Benzimidazole derivatives of the formula ##STR1## in which R and R.sub.1 independently of one another are each hydrogen, an alkanoyl group having 1 to 4 carbon atoms, an alkoxycarbonyl group having 1 to 4 carbon atoms, an alkylsulphonyl group having 1 to 4 carbon atoms, a benzoyl group, a phenylsulphonyl group or a p-methylphenylsulphonyl group; R.sub.2 and R.sub.4 independently of one another are each hydrogen, halogen or a methyl group, R.sub.3 is hydrogen, halogen, a methyl group or a methoxy group; X is oxygen or sulphur; Y is halogen, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a methylthio group, a methylsulphinyl group, a methylsulphonyl group, a trifluoromethyl group, a nitro group, a hydroxyl group, a cyano group or an acetyl group; and m is 0, 1, 2 or 3; and if one of the two radicals R or R.sub.1 is hydrogen, the position of the other of these radicals on the N atoms cannot be clearly established, including, when at least one of the two radicals R or R.sub.1 is hydrogen, the possible tautomeric compounds of the formula I; and the disulphides obtainable by oxidation of compounds of the formula I. The compounds are useful for combating helminths in domestic animals and productive animals.

New acylanilides are disclosed which act as microbicides. They may preferably be used for combating phytopathogenic fungi.

Hydrazino-acetanilide derivatives of the formula I ##STR1## wherein R.sub.1 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or halogen, R.sub.2 is C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.4 alkoxy or halogen, R.sub.3 is hydrogen, C.sub.1 -C.sub.3 alkyl or halogen, R.sub.4 is hydrogen or methyl, with the total number of C atoms of the substituents R.sub.1, R.sub.2, R.sub.3 and R.sub.4 in the phenyl ring not exceeding 6, R.sub.5 is C.sub.1 -C.sub.5 alkyl which is unsubstituted or substituted by halogen, or it is phenyl which is unsubstituted or substituted by methyl, nitro and/or halogen, or it is the benzyl group, and R.sub.6 is hydrogen or C.sub.1 -C.sub.5 alkyl, possess valuable microbicidal properties, and contained in appropriate compositions these derivatives can be used in particular for combating phytopathogenic fungi.

Bis-triazinylaminostilbene compounds of the formula ##STR1## in which R.sub.1 is alkyl, alkenyl, cyclohexyl or phenylalkyl, R.sub.2 is hydrogen, alkyl, cyclohexyl, benzyl, alkyl which is substituted by hydroxyl, cyano, sulpho or carbamoyl, alkoxyalkyl or hydroxyalkoxyalkyl or alkoxyalkoxyalkyl or mono- or di-alkylaminoalkyl, and R.sub.3 is hydrogen, alkyl, alkyl which is substituted by hydroxyl, cyano or sulpho, or alkoxyalkyl or hydroxyalkoxyalkyl or R.sub.2 and R.sub.3 together with the nitrogen atom to which they are bonded are a morpholine ring or a pyrrolidine, piperidine, hexamethyleneimine or piperazine ring which is unsubstituted or substituted by 1 or 2 alkyl groups, and M is hydrogen or an alkali metal, ammonium or amine ion, and, if R.sub.2 or R.sub.3 is hydroxyalkyl, R.sub.1 is methyl, cyclohexyl or alkenyl only, and their use as fluorescent brightening agents for organic material of high molecular weight are disclosed.

Compounds of the formula I ##STR1## wherein R.sub.1 represents C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or halogen, R.sub.2 represents C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.4 alkoxy or halogen, R.sub.3 represents hydrogen, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.4 alkoxy or halogen, R.sub.4 represents hydrogen or methyl, R.sub.5 represents C.sub.1 -C.sub.4 alkyl or phenyl, and n is 1, 2 or 3. These compounds possess fungicidal action.

A process for the production of 2-aryl-2H-benzotriazoles comprises reducing and cyclizing the corresponding o-nitroazobenzenes with hydrogen at a temperature in the range of about 20.degree. C. to about 100.degree. C. and at a pressure in the range of about 15 psia (1 atmosphere) to about 1000 psia (66 atmospheres) in an alkaline medium at a pH over 10 in the presence of a nickel catalyst, preferably molybdenum-promoted Raney nickel. High yields of pure product are obtained directly with a concomitant reduction of undesired by-product and a reduction in effluent pollution problems.

The invention relates to a process for the preparation of crosslinked polymers by reacting liquid epoxide compounds and polyisocyanates and, if desired, polyhydroxy compounds. The curing catalysts used are complex compounds of BF.sub.3 with ethers or phosphonium compounds or H.sub.2 O. If desired, a compound of one of the metals Sn, Zn or Fe which is soluble in the reaction mixture is also added. In most cases it is possible to dispense completely with the external supply of heat when carrying out the process according to the invention, since the reaction is sufficiently exothermic. The technical advance lies in the fact that it is largely possible to dispense with heating and insulating equipment when carrying out the reaction industrially. Despite this, astonishingly high glass transition temperatures are obtained.

This invention comprises new compounds as well as a composition and method for influencing, in particular for inhibiting plant growth, which composition contains as active ingredient a quaternary pyrrolidinium acetic acid anilide of the formula ##STR1## wherein X.crclbar. represents the anion of any non-phytotoxic acid. Methods for manufacturing the bromide of this compound are described and its use for inhibiting the growth of plants, in particular ornamentals.

Esters of phenol-dithiocarbamic acids when added even in very small amounts to lubricants are effective as stabilizers against oxidation and corrosion, and also as extreme-pressure additives and anti-wear additives.

Novel compounds of the general formula I ##STR1## wherein M.sup.q.sym. is a metal ion carrying a double or triple positive charge and q is 2 or 3 and r is 1 or 2, the quotient q/r being 1, 1.5, 2 or 3, and L is a piperidine which is substituted by at least one enolate group in the 1-position or 4-position and wherein the ring nitrogen is sterically hindered by alkyl substituents in the adjacent positions, and m is 0, 1 or 2 and A is H.sub.2 O or an amine.

Acylated phenylaminotetrahydro-2-furanones of the formula I disclosed herein, which have a systemic action, are suggested as novel microbicides. They can be used in the form of pesticidal compositions in particular for combating phytopathogenic fungi, or for preventing fungus infections on cultivated plants.

Amino aceto anilides of the formula I shown hereinafter are effective microbicides. They may be used to control fungi on plants or parts of plants or to prevent them from fungi attack.

The invention relates to the use of crystalline resins as storage material in latent heat accumulators. Crystalline synthetic resins replace the crystalline inorganic salt of the known latent heat reservoirs. Preferably epoxide resins, polyurethane resins and polyester resins, which contain very specific long-chain polyester molecule moieties, are used. The crystalline synthetic resins have one or more, preferably two, crystallite melt temperatures.

New substituted N-phenyl-N'-fluorobenzoylureas of the formula ##STR1## wherein R.sub.1 is a C.sub.2 -C.sub.3 -alkenyl group, a C.sub.2 -C.sub.4 -alkenyl group mono- or disubstituted by chlorine, or it is the propargyl group, R.sub.2 and R.sub.3 independently of one another are hydrogen or chlorine, and R.sub.4 is hydrogen or fluorine; processes for producing the said compounds and their use for combating pests, especially for the control of insects and representatives of the order Acarina, which infest plants and animals. The new compounds also have an antifeedant action on insects which cause damage to plants.

Metal phenolates having at least one piperidinyl group sterically hindered on the nitrogen atom are suitable as additives for organic material.

The compounds according to the invention have the formula I ##STR1## in which R.sup.1, R.sup.2 and R.sup.3 are monovalent organic radicals or chlorine and Z is a tetravalent organic radical and A is a divalent organic grouping. These products are to be used as adhesion promoters, especially between inorganic solids and organic resins. 4 processes of preparation are given.

Acylated phenylaminotetrahydro-2-furanones of the formula ##STR1## in which R is C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy or halogen, R.sub.1 is hydrogen, C.sub.1 -C.sub.3 -alkyl, C.sub.1 -C.sub.4 -alkoxy or halogen, R.sub.2 is hydrogen, C.sub.1 -C.sub.3 -alkyl or halogen, R.sub.3 is hydrogen or methyl, with the total number of C atoms of the substituents R, R.sub.1, R.sub.2 and R.sub.3 in the phenyl ring not exceeding 8, R.sub.4 and R.sub.5 independently of one another are hydrogen or methyl, and R.sub.6 is a C.sub.1 -C.sub.4 -alkyl group unsubstituted or substituted by halogen, thiocyano, cyano, C.sub.1 -C.sub.4 -alkoxy or C.sub.1 -C.sub.4 -alkylthio, or R.sub.6 is a C.sub.2 -C.sub.5 -alkenyl or C.sub.3 -C.sub.7 -cycloalkyl group each unsubstituted or mono- or polysubstituted by halogen, or R.sub.6 is a phenyl or benzyl group each unsubstituted or substituted by halogen, nitro, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy, or R.sub.6 is a 5- or 6-membered heterocyclic radical unsubstituted or substituted by methyl, have a systemic action, are suggested as novel microbicides. They can be used in the form of pesticidal compositions in particular for combating phytopathogenic fungi, or for preventing fungus infections on cultivated plants.

Novel substituted 11-amino-undeca-4,8-dienal and 11-amino-undecanal aldehyde-derivatives of the formulae Ia ##STR1## in which R.sub.1 to R.sub.6, Y and m are as defined in patent claim 1, and processes for their preparation are described. The compounds of the formulae Ia and Ib can be catalytically hydrogenated to novel 1,11-diaminoundecanes, which, in turn, can be used, for example, for the preparation of polycondensation products, in particular transparent polyamides, or as curing agents for epoxide resins.

Compounds which contain, in their molecule, at least one 2-(2'-hydroxyphenyl)-benztriazole group or one 2-hydroxybenzophenone group and at least one polyalkylpiperidine group are effective light stabilizers for organic materials, in particular for polymers. The use of the compounds as light stabilizers for lacquers is of particular importance.

The mixture contains as reinforcing agent needle-shaped crystals insoluble in epoxide resin, the crystals being for example of aluminium oxide or hydroxide and acetic acid, propionic acid, benzoic acid, adipic acid or sebacic acid. These crystals improve specific mechanical properties of the elastomeric polymers obtained by curing the epoxide resin/curing agent mixture, without the elastomeric properties being lost.

New acylanilides of the formula ##STR1## wherein R.sub.1 represents alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms or halogen, R.sub.2 represents hydrogen, alkyl of 1 to 3 carbon atoms, alkoxy of 1 to 4 carbon atoms or halogen, R.sub.7 represents hydrogen, alkyl of 1 to 3 carbon atoms, alkoxy of 1 to 4 carbon atoms or halogen, R.sub.8 represents hydrogen or methyl, the total number of carbon atoms of the substituents R.sub.1, R.sub.2, R.sub.7 and R.sub.8 in the phenyl ring not exceeding 8, X represents ##STR2## wherein each of R', R" and R'" independently represents hydrogen, methyl, or ethyl, and Y represents one of the following groups: ##STR3## wherein Hal is a halogen anion, (b) --O--R.sub.4, (c) --S--R.sub.4, wherein R.sub.4 represents alkyl of 1 to 6 carbon atoms, alkenyl of 3 to 6 carbon atoms, alkynyl of 3 to 6 carbon atoms, each of them unsubstituted or substituted by a halogen atom, or R.sub.4 represents benzyl of phenyl which independently may be unsubstituted or substituted by halogen or alkyl of 1 to 4 carbon atoms or ##STR4## wherein each of R.sub.5 and R.sub.6 independently represents alkyl of 1 to 4 carbon atoms are disclosed which act as microbicides. They may preferably be used for combating phytopathogenic fungi.

N-Acylated N-phenyl-aminotetrahydro-2-furanones of tthe formula ##STR1## wherein R represents C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy or halogen, R.sub.1 represents C.sub.1 -C.sub.3 -alkyl, C.sub.1 -C.sub.4 -alkoxy or halogen, R.sub.2 represents hydrogen, C.sub.1 -C.sub.3 -alkyl, C.sub.1 -C.sub.4 -alkoxy or halogen, R.sub.3 represents hydrogen or methyl, with the total number of C atoms of the substituents R, R.sub.1, R.sub.2 and R.sub.3 in the phenyl ring not exceeding the number 8, R.sub.4 represents hydrogen or methyl, while R.sub.5 represents one of the following groups: an alkylthioalkyl or alkoxyalkyl group having 2 to 5 carbon atoms or an alkoxyalkoxymethyl group having a maximum of 6 carbon atoms, a 2-furanyl or 2-tetrahydrofuranyl group optionally substituted by halogen, a 1,2,4-triazolymethyl group, a 1,2-pyrazolylmethyl group, or a group -CH.sub.2 -OR.sub.6 in which R.sub.6 represents a 5- or 6-membered heterocycle having oxygen as the hetero atom are valuable fungicidal active substances. They can be used as fungicidal compositions, particularly for combating phytopathogenic fungi, e.g. against downy mildew on potatoes, tomatoes, grape vines and sugar beet and other plants. The novel compounds have a systemic action.

Novel oligomeric and polymeric phenolic 1,3,5-triazines, for example those of the formula ##STR1## their preparation and their use for stabilizing organic material and also the organic material protected against oxidative and light-induced degradation with the aid of these compounds.

Adhesion of metals to vulcanizable elastomers is promoted by a process of incorporating into the elastomer a metal deactivator and then vulcanizing the elastomeric composition while it is in contact with the metal surface.

Fluorochemical surfactants of the formula ##STR1## wherein R.sub.f is perfluoroalkyl of 4-20 carbon atoms or perfluoroalkoxyperfluoroalkyl of 4-20 carbon atoms; A is straight or branched chain alkylene of 1-10 carbon atoms which is unsubstituted or substituted by halo; n is 1 to 50; R.sub.1 is hydrogen or alkyl of 1-4 carbon atoms and R.sub.2 is hydrogen or alkyl of 1-4 carbon atoms.

Aromatic-aliphatic ketones of the formulae I, II, III or IV ##STR1## wherein n is 1 or 2, Ar is an aryl radical, R.sup.1 and R.sup.2 are monovalent aliphatic, cycloaliphatic or araliphatic radicals, R.sup.3 is a direct bond or a divalent organic radical, X is a hydroxyl or amino group or the monovalent etherification or silylation products thereof, and X' is a divalent amino, ether or silyloxy group, Y is a direct bond or CH.sub.2 and Z is O, S, SO.sub.2, CH.sub.2 or C(CH.sub.3).sub.2, are suitable sensitizers for the photopolymerization of unsaturated compounds and for the photochemical crosslinking of polyolefins. Some of these compounds are novel and can be obtained by methods analogous to those for obtaining the known compounds of this type.

N-Acylated N-phenyl-aminotetrahydro-2-furanones of the formula ##STR1## wherein R represents C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy or halogen, R.sub.1 represents C.sub.1 -C.sub.3 -alkyl, C.sub.1 -C.sub.4 -alkoxy or halogen, R.sub.2 represents hydrogen, C.sub.1 -C.sub.3 -alkyl, C.sub.1 -C.sub.4 -alkoxy or halogen, R.sub.3 represents hydrogen or methyl, with the total number of C atoms of the substituents R, R.sub.1, R.sub.2 and R.sub.3 in the phenyl ring not exceeding the number 8, R.sub.4 represents hydrogen or methyl, while R.sub.5 represents one of the following groups: an alkylthioalkyl or alkoxyalkyl group having 2 to 5 carbon atoms or an alkoxyalkoxymethyl group having a maximum of 6 carbon atoms, a 2-furanyl or 2-tetrahydrofuranyl group optionally substituted by halogen, a 1,2,4-triazolylmethyl group, a 1,2-pyrazolylmethyl group, or a group --CH.sub.2 --OR.sub.6 in which R.sub.6 represents a 5- or 6-membered heterocycle having oxygen as the hetero atom are valuable fungicidal active substances. They can be used as fungicidal compositions, particuarly for combating phytopathogenic fungi, e.g. against downy mildew on potatoes, tomatoes, grape vines and sugar beet and other plants. The novel compounds have a systemic action.

New cyanuric acid derivatives containing at least one hindered phenolic moiety and at least one hindered amine moiety are effectful light stabilizers and antioxidants for polymeric materials.

Aromatic-aliphatic ketones of the formulae I, II, III or IV ##STR1## wherein n is 1 or 2, Ar is an aryl radical, R.sup.1 and R.sup.2 are monovalent aliphatic, cycloaliphatic or araliphatic radicals, R.sup.3 is a direct bond or a divalent organic radical, X is a hydroxyl or amino group or the monovalent etherification or silylation products thereof, and X' is a divalent amino, ether or silyloxy group, Y is a direct bond or CH.sub.2 and Z is O, S, SO.sub.2, CH.sub.2 or C(CH.sub.3).sub.2, are suitable sensitizers for the photopolymerization of unsaturated compounds and for the photochemical crosslinking of polyolefins. Some of these compounds are novel and can be obtained by methods analogous to those for obtaining the known compounds of this type.

The title compounds are prepared by reacting alkylated 1,1'-biphenyl-2,2'-diol or alkylated 2,2'-alkylidene-bis-phenol with phosphorus trichloride in an organic solvent and then reacting the intermediate phosphorochlorodite with an alkanolamine. Said phosphites are useful as stabilizers of organic polymers and lubricating oils, especially as processing stabilizers for polyolefins, elastomers, polyesters and polycarbonates.

Compounds of the formula I ##STR1## wherein R.sub.1 is hydrogen, C.sub.1 -C.sub.18 alkyl, C.sub.5 -C.sub.12 cycloalkyl, phenyl or C.sub.7 -C.sub.9 phenylalkyl and R.sub.2 is hydrogen or C.sub.1 -C.sub.18 alkyl, or, if R.sub.1 is hydrogen, R.sub.2 is a divalent 1,1,3,3,-tetramethylpropylene radical fused in the 2-position and 3-position or the 9-position and 10-position, and X is sulfur or a group --CH(R).sub.3 --, in which R.sub.3 is hydrogen or a radical of the formula II --CH(R.sub.4)--CH(R.sub.5)SR.sub.6, and each of R.sub.4 and R.sub.5 independently is hydrogen or C.sub.1 -C.sub.6 alkyl and R.sub.6 is C.sub.1 -C.sub.20 alkyl, while the alkyl group can be interrupted by one or more sulfur atoms, and A is a primary or secondary aliphatic or alicyclic, aromatic or araliphatic amine which contains substituents of the same type or mixed substituents, or a heterocyclic amine or a hydrazine derivative. These compounds are useful stabilizers for organic material.

N-substituted aspartic acid monoesters of the formula I ##STR1## wherein for example R.sub.1 is an alkyl group having 1 to 12 C atoms, cyclohexyl, phenyl, tolyl or benzyl, x is 2 or 3, R.sub.2 and R.sub.3 are each a methyl or ethyl group, or together with the N atom they form an N-heterocyclic ring, are obtained by adding, by means of an addition reaction, to 1 mol of a maleic acid monoester of the formula II ##STR2## 1 mol of an amine of the formula III ##STR3## in the presence of a tertiary amine. The novel N-substituted aspartic acid monoesters are valuable curing accelerators for epoxide resin mixtures containing dicyandiamide or a polycarboxylic acid anhydride as curing agent. They are also suitable alone as catalytically acting curing agents for epoxide resins.

Aluminium monohydroxide salts of a carboxylic acid which are free from water of crystallization and have the formula ##STR1## or contain the structural element of the formula ##STR2## in which R is methyl, ethyl or phenyl or R.sup.1 is the divalent group --C.sub.n H.sub.2n --, in which n is a number from 3 to 10, and which can also be in the form of a dimer, have an acicular to rod-shaped crystal form. They are suitable as fillers for polymers, especially as reinforcing fillers for elastomeric epoxide resins.

A resinous hardener system comprising the reaction product of diamino diphenylsulfone compounds and diglycidyl ethers of polyhydric phenols. The hardener system can be incorporated into a variety of epoxy resins for use as improved prepreg or laminating resins, as resin molded castings, and the like.

One-component systems which are stable on storage and can be converted to crosslinked epoxide resins on heating and which contain a crystalline epoxide resin with, on average, more than one epoxide group per molecule and a melting point between 40.degree. and 150.degree. C., and, homogeneous distribution, a curing catalyst.

Amino aceto anilides of the formula ##STR1## wherein R.sub.1 represents C.sub.1 -C.sub.4 -alkyl, a C.sub.1 -C.sub.4 -alkoxy or a halogen, R.sub.2 represents hydrogen, C.sub.1 -C.sub.3 -alkyl, C.sub.1 -C.sub.4 -alkoxy or halogen, R.sub.3 represents a hydrogen, C.sub.1 -C.sub.3 -alkyl or halogen, R.sub.4 represents hydrogen or methyl, with the proviso that the total number of carbon atoms contained by the substituents R.sub.1, R.sub.2, R.sub.3 and R.sub.4 does not exceed 8, and X represents --CH.sub.2 -- or ##STR2## R.sub.5 represents --COOR', COSR' or ##STR3## wherein each of R', R" and R''' independently represents methyl or ethyl, R.sub.6 represents hydrogen or has a meaning assigned to R.sub.7, albeit an independent one, R.sub.7 represents a C.sub.1 -C.sub.6 -alkyl group which is unsubstituted or substituted by cyano, hydroxyl or C.sub.1 -C.sub.3 -alkoxy, or a C.sub.3 -C.sub.6 -alkenyl which is unsubstituted or substituted by halogen, or else represents a C.sub.3 -C.sub.6 -alkynyl or C.sub.3 -C.sub.7 -cycloalkyl, while R.sub.6 and R.sub.7 together with the nitrogen atom to which they are attached can represent a C.sub.2 -C.sub.6 -alkylene or alkenylene group which is unsubstituted or mono- or polysubstituted by halogen or C.sub.1 -C.sub.3 -alkyl and which can contain one or two heteroatoms, and salts of the compounds of the formula I with inorganic or organic acids; are effective microbicides. They may be used to control fungi on plants or parts of plants or to prevent them from fungi attack.

The compounds according to the invention have the formula I ##STR1## in which R.sup.1, R.sup.2 and R.sup.3 are monovalent organic radicals or chlorine and Z is a tetravalent organic radical and A is a divalent organic grouping. These products are to be used as adhesion promoters, especially between inorganic solids and organic resins. 4 processes of preparation are given.

The process according to the invention is performed by reaction of epoxide resins with primary and/or secondary polyamines with simultaneous quaternizing by means of aromatic and aliphatic polysulfonic esters, halogen-free organic phosphoric esters, or organic compounds which contain at least 1 chlorine or bromine atom, and which are free from -COOH groups and corresponding salt groups. The crosslinked plastics thus obtained are distinguished by an improved electrical conductivity.

Chlorine-containing thermoplastics, containing a pyrrole of the formula I ##STR1## in which R.sub.1 is hydrogen, alkyl, cycloalkyl, aryl, alkoxycarbonylmethyl, free or esterified .alpha.-hydroxyalkyl, free or esterified .alpha.-hydroxycycloalkylmethyl, free or esterified .alpha.-hydroxyaralkyl, alkoxymethyl, alkylthiomethyl, aryloxymethyl, arylthiomethyl, cycloalkoxymethyl, cycloalkylthiomethyl, aralkoxymethyl, aralkylthiomethyl, alkoxy, alkylthio, cycloalkoxy, cycloalkylthio, aralkoxy, arylalkylthio, aryloxy, arylthic, halogen, mercapto, mercaptomethyl or hydroxyl, R.sub.2 is hydrogen, alkyl, cycloalkyl, aryl, free or esterified .alpha.-hydroxyalkyl, in which the alkyl moiety together with R.sub.1 can be alkylene, or free or esterified .alpha.-hydroxycycloalkylmethyl, free or esterified .alpha.-hydroxyaralkyl, alkoxy, cycloalkoxy, aralkoxy, aryloxy, alkylthio, cycloalkylthio, aralkylthio, arylthio, alkoxymethyl, alkylthiomethyl, aryloxymethyl, arylthiomethyl, cycloalkoxymethyl, cycloalkylthiomethyl, aralkoxymethyl, aralkylthiomethyl, hydroxyl, cyano, free carboxyl or carboxyl in the form of a salt or an ester, or acyl, it being possible for acyl together with R.sub.1 to be --CO-alkylene, in which --CO-- is bonded in the 3-position, or R.sub.2 is halogen, mercapto or mercaptomethyl, and R.sub.3 is alkyl, cycloalkyl, aralkyl, aryl, free or esterified hydroxymethyl, alkoxymethyl, alkylthiomethyl, cycloalkoxymethyl, cycloalkylthiomethyl, aralkoxymethyl, arylalkylthiomethyl, aryloxymethyl or arylthiomethyl, alkoxy, alkylthio, cycloalkoxy, cycloalkylthio, aralkoxy, aralkylthio, aryloxy, arylthio, halogen, mercapto or mercaptomethyl, or if R.sub.2 is carboxyl in the form of a salt, R.sub.3 is hydrogen and R.sub.1 is as defined, or in which R.sub.3 is hydroxyl and R.sub.1 is hydrogen, alkyl or aryl and R.sub.2 is hydrogen, alkyl, aryl or acyl, or a salt thereof.

The title compounds are prepared by reacting alkylated 1,1'-biphenyl-2,2'-diol or alkylated 2,2'-alkylidene-bis-phenol with phosphorus trichloride in an organic solvent and then reacting the intermediate phosphorochlorodite with an alkanolamine. Said phosphites are useful as stabilizers of organic polymers and lubricating oils, especially as processing stabilizers for polyolefins, elastomers, polyesters and polycarbonates.

Novel ligands of the general formula wherein r is 1 or 2, and L is a piperidine which is substituted by at least one enolate group in the 1-position or 4-position and wherein the ring nitrogen is sterically hindered by alkyl substituents in the adjacent positions. These ligands are useful in preparing light stabilizers.

The invention relates to novel 4-(1H-azolylmethyl)-1,3-dioxolan-5-one derivatives of the formula I ##STR1## and to the production and use of these compounds. In formula I, R.sub.1 and R.sub.2 are unsubstituted or substituted alkyl or phenyl, or together form a 3- to 7-membered carbocyclic ring which is unsubstituted or substituted, A is an unsubstituted or substituted phenyl radical, and X is --CH.dbd. or --N.dbd.. The compounds of the formula I can be used in the form of appropriate compositions for regulating plant growth and/or for controlling and/or protecting plants from attack by phytopathogenic microorganisms.

Compounds of the formula I ##STR1## wherein R.sub.1 is hydrogen, C.sub.1 -C.sub.18 alkyl, C.sub.5 -C.sub.12 cycloalkyl, phenyl or C.sub.7 -C.sub.9 phenylalkyl and R.sub.2 is hydrogen or C.sub.1 -C.sub.18 alkyl, or, if R.sub.1 is hydrogen, R.sub.2 is a divalent 1,1,3,3-tetramethylpropylene radical fused in the 2-position and 3-position or the 9-position and 10-position, and X is sulfur or a group --CH(R).sub.3 --, in which R.sub.3 is hydrogen or a radical of the formula II --CH(R.sub.4)--CH(R.sub.5)SR.sub.6, and each of R.sub.4 and R.sub.5 independently is hydrogen or C.sub.1 -C.sub.6 alkyl and R.sub.6 is C.sub.1 -C.sub.20 alkyl, while the alkyl group can be interrupted by one or more sulfur atoms, and A is a primary or secondary aliphatic or alicyclic, aromatic or araliphatic amine which contains substituents of the same type or mixed substituents, or a heterocyclic amine or a hydrazine derivative. These compounds are useful stabilizers for organic material.

Mixtures which contain (a) polymeric ammonium salts which are soluble or give microemulsions in aqueous surfactant systems and which can be obtained by water-in-oil emulsion polymerization or solution polymerization of a quaternary ammonium salt of the acrylic acid series and optionally at least one other acrylic monomer, and which has a molecular weight distribution of 10.sup.4 to 10.sup.9, the molecular weight of at least 5 percent of the polymer being 10.sup.7 to 10.sup.9, and (b) a non-ionic surfactant or a surfactant with one positive and one negative charge within the molecule, can be used as cosmetics, in particular as hair cosmetics, the hair treated according to the invention having an excellent ease of dry combing and, in particular, wet combing.

A process is proposed for bleaching textiles or removing stains from textiles and for combating micro-organisms in or on organic or inorganic substrates, or for protecting the latter against attack by micro-organisms, by treating the textiles or the substrates to be freed of or protected from micro-organisms with a water-soluble zinc phthalocyanine or aluminium phthalocyanine, in the presence of water and under irradiation with light, in which process a sulfonated zinc phthalocyanine or aluminium phthalocyanine which is further substituted by neutral groups which do not confer solubility in water, for example by halogen atoms or pseudo-halogens, or a mixture of these phthalocyanine compounds, is used as the water-soluble zinc phthalocyanine or aluminium phthalocyanine. Bleaching, washing and soaking agents or agents having an antimicrobial action, for carrying out the process, are also proposed, which, in addition to the active ingredient, contain, if appropriate, inorganic salts, water and also, in the case of washing agents, customary washing agent constituents. Novel sulfonated zinc phthalocyanine and aluminium phthalocyanine compounds and their preparation are furthermore described.

Aqueous dispersions of a phenolic resole and a thermoplastics polymeric material or a rubber, suitable for use as adhesives, are prepared by (a) dissolving a solid thermoplastics polymeric material, such as a polyvinyl acetal or a nylon polyamide, or rubber in a phenol, (b) adding a nonionic or anionic surface active agent and/or protective colloid, (c) adjusting the mixture to a pH above 7 by addition of a base, (d) adding aqueous formaldehyde solution, or a formaldehyde donor, to a molar ratio of phenol to formaldehyde within the range 1:1 to 1:3, (e) if necessary, adding water, and (f) heating the mixture to form a phenolic resole.

Use of succinosuccinic acid diesters of the formula ##STR1## in which R is an alkyl, alkenyl or cycloalkyl having 4 to 24 C atoms, either dissolved in a water-immiscible organic solvent, or at elevated temperature in the form of their melts, as cation-selective liquid membranes.

Amino aceto anilides of the formula I shown hereinafter are effective microbicides. They may be used to control fungi on plants or parts of plants or to prevent them from fungi attack.

The alpha crystalline modification of 2,2',2"-nitrilo[triethyl-tris-(3,3',5,5'-tetra-tert-butyl-1,1'-biphenyl-2, 2'-diyl)phosphite] is obtained by crystallizing said compound from selected solvents, preferably from a mixture of an aromatic hydrocarbon solvent and a lower alkanol. The alpha crystalline form is an effective process stabilizer for polyolefins, particularly polypropylene.

Compounds of formula (I): ##STR1## and of formula (I).sub.w : ##STR2## in which: A represents group having one of the following formulae: ##STR3## wherein R.sup.2, R.sup.3 and R.sup.4 are independently selected from the group consisting of hydrogen atoms, halogen atoms, alkyl groups having from 1 to 4 carbon atoms, and alkoxy groups having from 1 to 4 carbon atoms; R.sup.1, R.sub.w.sup.1 and R.sub.w.sup.2 are, for example, hydrogen, halogen, cyano, nitro, optically substituted alkyl, alkoxy or alkoxyalkoxy; X or X.sub.w is hydroxy, alkanoyloxy, substituted alkanoyloxy or hydroxyimino; R.sup.3.sub.w and R.sup.4.sub.w are each hydrogen, alkyl or alkoxy; R.sup.5 and R.sup.5.sub.w are methyl, ethyl, isopropyl or sec-butyl; and salts thereof have valuable anthelmintic, acaricidal and insecticidal activities.

Novel phthalocyanine compounds are described, which have the formula ##STR1## in which MePc is the Si(IV)-, P(V)-, Ti(IV)-, Ge(IV)-, Cr(IV)-, Ga(III)-, Zr(IV)-, In(III)-, Sn(IV)- or Hf(IV)- phthalocyanine or -naphthalocyanine ring system, A is an anionic, nonionic or cationic group which imparts solubility in water, Z is the counter-ion to A, if the latter is an ionic group, and is 0 if A is a nonionic group, n is any desired number from 1 to 8, Y is a neutral substituent which does not impart solubility in water and p is any desired number from 0 to 6, it being possible for the groups AZ and Y present in the molecule to be identical or different in either case, and the sum of n+p being not more than 8 and MePc not being the Sn(IV)-phthalocyanine or Sn(IV)-naphthalocyanine ring system if p is 0 and if the only groups imparting water-solubility in the molecule are sulfo groups. The novel compounds can be used as photoactivators, particularly for bleaching textiles and for controlling microorganisms in or on organic or inorganic substrates. Bleaching, washing and steeping agents and agents having antimicrobial activity, which contain the novel phthalocyanine compounds, are also described.

Phosphonous acid monoester-monoamides of the formula ##STR1## in which n is 1, R.sub.1 is phenyl, R.sub.2, R.sub.3 and R.sub.4 are independently hydrogen or alkyl, R.sub.5 is alkyl or cyclohexyl, R.sub.6 is 2,2,6,6-tetramethylpiperidin-4-yl or ##STR2## R.sub.3 may also be ##STR3## where X is methylene or isopropylidene and R.sub.6 is alkyl or cyclohexyl. Said compounds are suitable for protecting organic material from the harmful effect of heat, oxygen and light.

Novel azaphthalocyanines are described which are of the formula ##STR1## in which Me is Al(III), Zn(II), Ge(IV) or Sn(IV), E is an anionic group, Z is a cation, Y is a halogen, n is any desired number from 1 to 3 and p is any desired number from 0 to 2, the sum n+p being at most 8 and A, B, C and D independently of one another completing a benzene ring or a ring of the formula ##STR2## at least one of the rings completed by A, B, C or D being one of the said heterocyclic rings. The novel compounds can be used as photoactivators, in particular for bleaching textiles and for controlling microorganisms in or on organic or inorganic substrates. Bleaching, washing and steeping agents and antimicrobially active agents are also described which contain the novel azaphthalocyanine compounds. The azaphthalocyanine pigments which arise as intermediates and which do not carry groups EZ imparting solubility in water, their preparation and their use as photosensitizers in non-aqueous or heterogeneous systems are likewise described.

There are described microbicidally effective mandelic acid derivatives and mandelonitriles of the formula I ##STR1## wherein X is --CH.dbd. or --N.dbd.; Ar is phenyl, diphenyl or naphthyl group, which can be substituted in the form of the substituents R.sub.1 -R.sub.3 by nitro, halogen, alkyl, alkoxy or haloalkyl; R is any one of the groups --COOR.sub.5, --COSR.sub.6, --CON(R.sub.7)(R.sub.8) or CN; n is 0, 1 or 2; and R.sub.4 to R.sub.8 are aliphatic and aromatic and in part also heterocyclic substituents which are described in the text in greater detail; with the inclusion of the salts and metal complexes thereof. Also methods for producing these products are disclosed, and also pesticidal compositions containing as active ingredient one of these compounds. There is described too a method for combating phytopathogenic microorganisms with the aid of these substances.

Organic aprotic solvent insoluble polymers which are derivatives of a polyvinyl alcohol, having a weight average molecular weight of at least about 2,000, and containing from about 0.5 to about 90 percent, based on the number of hydroxyl groups in said polyvinyl alcohol, of an addition reaction product of units of the formula ##STR1## with a vinylic monomer, wherein R.sub.1 and R.sub.2 are independently alkylene, arylene, cycloaliphatic, aralkylene or aralkarylene, n is 0 or 1, A.sub.1 is a carbamoyloxy or ureido linking group, A is an oxa, imino or ureido group, R.sub.3 is hydrogen or methyl, R.sub.4 is hydrogen, or when R.sub.3 is hydrogen, methyl or also --COOR.sub.5 where R.sub.5 is hydrogen or lower alkyl, and hydrogel contact lenses made therefrom and their preparation.

The invention relates to lipopeptides of the formula I, ##STR1## in which each of R.sub.a.sup.1 and R.sub.b.sup.1, independently of the other, represents an aliphatic or cycloaliphatic-aliphatic hydrocarbon radical having from 7 to 21 carbon atoms that is optionally substituted by oxygen functions, or one of the radicals R.sub.a.sup.1 --CO-- and R.sub.b.sup.1 --CO-- represents hydrogen and the other of the radicals R.sub.a.sup.1 --CO-- and R.sub.b.sup.1 --CO-- represents an acyl radical, wherein R.sub.a.sup.1 and R.sub.b.sup.1 have the meanings given above, R.sup.2 represents an aliphatic or cycloaliphatic-aliphatic hydrocarbon radical having from 1 to 21 carbon atoms that is optionally substituted by oxygen functions, n=0 or 1, As.degree. represents a radical of the formula --O--Kw--CO-- or --NH--Kw--CO-- wherein Kw represents an aliphatic hydrocarbon radical having a maximum of 12 carbon atoms, As.sup.1 represents a D- or L-.alpha.-amino acid, each of Z.sup.1 and Z.sup.2, independently of the other, represents hydroxy or the N-terminal radical of a D- or L-.alpha.-aminocarboxylic acid, of an amino-lower alkanesulphonic acid or of a peptide having a maximum of 6 amino acids from the group consisting of D- or L-.alpha.-aminocarboxylic acids and amino-lower alkanesulphonic acids, and Z.sup.3 represents hydrogen or --CO--Z.sup.4 wherein Z.sup.4 represents hydroxy or the N-terminal radical of a D- or L-.alpha.-amino acid, of an amino-lower alkanesulphonic acid or of a peptide having a maximum of 6 amino acids from the group consisting of D- or L-.alpha.-aminocarboxylic acids and amino-lower alkanesulphonic acids, and the amides and esters of such compounds that contain carboxy groups. The novel lipopeptides have an immunity-stimulating action.

Linear polyether resins containing 100 to 10 mol % of the repeating structural unit of formula I ##STR1## and 90 to 0 mol % of the repeating structural unit of formula II ##STR2## wherein A is a linear unsubstituted or methyl-substituted alkylene group containing 4 to 100 carbon atoms in the linear alkylene chain, X denotes bridge members as defined in claim 1 and Y is an aromatic radical of a divalent phenol as defined in claim 1, are self-crosslinkable and can be crosslinked by heating to a temperature of not less than 250.degree. C. or by irradiation with energy-rich electromagnetic rays, affording products which are insoluble in organic solvents and which have high glass transition temperatures.

High molecular weight organic material is effectively colored by the incorporation therein of a copper or nickel complex of the ligand compound of formula I ##STR1## wherein A is an isocyclic or heterocyclic aromatic moiety, R is H, halogen, lower alkyl or alkoxy, R.sub.1 is H, lower alkyl, phenyl or substituted phenyl, and B is H, lower alkyl, ureido or substituted ureido, guanidino, anilino, benzamido or a heterocyclic aromatic moiety.

Organic aprotic solvent soluble polymers which are derivatives of a polyvinyl alcohol, having a weight average molecular weight of at least about 2,000, and containing from about 0.5 to about 90 percent, based on the number of hydroxyl groups in said polyvinyl alcohol, of units of the formula ##STR1## wherein R.sub.1 and R.sub.2 are independently alkylene, arylene, cycloaliphatic, aralkylene or aralkarylene, n is 0 or 1, A.sub.1 is a carbamoyloxy or ureido linking group, A is an oxa, imino or ureido group, R.sub.3 is hydrogen or methyl, R.sub.4 is hydrogen, or when R.sub.3 is hydrogen, methyl or also -COOR.sub.5 where B.sub.5 is hydrogen or lower alkyl, and crosslinked hydrogel contact lenses made therefrom and their preparation.

Compounds of the formula ##STR1## are described in which R.sub.1 represents a perfluoroalkyl radical of from 1 to 2 carbon atoms, and at least one of R.sub.2 and R.sub.3 represents hydrogen, and the other, or both represent lower alkyl, and R.sub.4 represents a lower alkyl radical which may be unsubstituted or bear certain substitution, and which are useful as herbicides in a method for controlling weeds and wild grasses. Compositions containing such compounds are also described. Finally, novel fluoro-thio semicarbazides are described which are useful intermediates in the production of the compounds of Formula I.

Aqueous or partly aqueous systems are treated against the corrosion of metals, especially ferrous metals, in contact therewith, and/or against scale deposition therefrom, by adding to these systems from 0.1 to 50 000 ppm of 2-hydroxyphosphonoacetic acid having the formula I ##STR1## or a water-soluble salt thereof.

The invention relates to curable mixtures comprising (a) at least one epoxy resin containing on average more than one epoxy group in the molecule, (b) at least one diethylphenyl-biguanide of formula I ##STR1## or a combination of a biguanide of formula I and a ketone resin, a ketone/formaledhyde resin or a phenoxy resin, as curing agent, and (c) optionally a curing accelerator. These mixtures are suitable for example as casting resins, laminating resins and, in particular, as powder coating compositions.

The invention relates to 1-aryl-2-fluoro-2-azolyl alkanones, alkanols, esters and ethers of formula I ##STR1## wherein Az is 1H-1,2,4-triazole, 4H-1,2,4-triazole or 1H-imidazole; T is --C(O)--, --CH(OH)-- or one of the groups ##STR2## wherein R.sub.7 is C.sub.1 -C.sub.6 alkyl which is unsubstituted or substituted by C.sub.1 -C.sub.3 -alkoxy, halogen or cyano, or is C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 alkynyl, C.sub.3 -C.sub.6 cycloalkyl, 2-furyl, 2-tetrahydrofuryl, or is phenyl or benzyl, each unsubstituted or substituted by halogen, nitro, C.sub.1 -C.sub.3 -alkyl, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 haloalkyl and/or C.sub.1 -C.sub.3 haloalkoxy; R.sub.8, R.sub.9 and R.sub.10 are each independently hydrogen, nitro, halogen, cyano, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 haloalkoxy, --COO(C.sub.1 -C.sub.3 alkyl), NH.sub.2 or NHCOCH.sub.3 ; R is hydrogen or C.sub.1 -C.sub.6 alkyl; R.sub.1 and R.sub.2 are each independently hydrogen, halogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 haloalkyl, C.sub.1 -C.sub.6 haloalkoxy, nitro and/or cyano; and R.sub.3 is hydrogen, halogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 haloalkyl, C.sub.1 -C.sub.6 haloalkoxy, nitro, cyano and/or the group ##STR3## wherein X is O, S, SO or SO.sub.2 ; R.sub.4, R.sub.5 and R.sub.6 are each independently hydrogen, halogen, cyano, nitro, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 haloalkyl and/or C.sub.1 -C.sub.6 haloalkoxy; and to the acid addition salts and metal complexes thereof. These compounds have microbicidal properties and can be used in particular against diseases occurring in rice. The invention also relates to the preparation and use of these compounds.

Mixtures of substances which are obtainable by reacting elementary sulfur with compounds of the formula I ##STR1## are described. The radical X contains an olefinic double bond. R is a hydrocarbon radical, p is 0, 1 or 2 and t is 1, 2 or 3. The mixtures of substances according to the invention can be employed as antioxidants in organic polymers and in lubricants. They can also be used as high-pressure additives or anti-wear additives.

Compounds of formula I or II ##STR1## wherein R.sup.1 and R.sup.2 are hydrogen, alkyl, cyclohexyl, phenyl, benzyl or tolyl, or are a --CH.sub.2 --CHR.sup.3 --CH.sub.2 --S--CO--R.sup.4 radical, R.sup.3 is hydrogen or methyl, R.varies.is alkyl, cyclohexyl, phenyl, benzyl or tolyl, X is alkylene, --S--, --SO--, --SO.sub.2 -- or substituted alkylene, in which R.sup.5 and R.sup.6 are hydrogen or alkyl, and n is an integer from 1 to 10, can be used as latent hardeners for epoxy resins. The compositions containing epoxy resins and these hardeners are particularly suitable for use as single component adhesive formulations. The cured products have good hot water resistance.

The invention relates to a novel process for the preparation of the optically pure 2S- or 2R-indolinecarboxylic acid of the formula ##STR1## and salts thereof. The process comprises forming the heterocyclic 5-membered ring in formula I from an open chain precursor by diastereoselective cyclization.

Monoazo compounds of the formula ##STR1## in which one of the two substituents R.sub.1 or R.sub.2 or both substituents are C.sub.3 -C.sub.8 -alkyl or a group of the formula ##STR2## in which R.sub.3 and R.sub.4 are independently of each other hydrogen or C.sub.1 -C.sub.4 -alkyl and R.sub.5 is hydrogen, halogen or C.sub.1 -C.sub.4 -alkyl and the other of the two substitutents R.sub.1 or R.sub.2, when the two are not C.sub.3 -C.sub.8 -alkyl or a group of the formula (1a), is hydrogen, halogen or C.sub.1 -C.sub.4 -alkyl, and KK is the radical of a coupling component which is free of water-solubilizing groups the two described. These compounds can be used as dyes for dyeing or printing for example polyester fibre materials.

Imides of formula I ##STR1## wherein R.sup.1 and R.sup.2 are independently hydrogen or methyl, R.sup.3 is a direct bond, alkylene, oxaalkylene, cycloalkylene, arylene or arylene-T-arylene where T is methylene or isopropylidene, and R.sup.4 alkyl, cycloalkyl, aryl, benzyl or alkaryl are suitable as catalysts for the crosslinking of specific unsaturated imides.

Organic aprotic solvent soluble polymers which are derivatives of a polyvinyl alcohol, having a weight average molecular weight of at least about 2,000, and containing from about 0.5 to about 90 percent, based on the number of hydroxyl groups in said polyvinyl alcohol, of units of the formula ##STR1## wherein R.sub.1 and R.sub.2 are independently alkylene, arylene, cycloaliphatic, aralkylene or aralkarylene, n is 0 or 1, A.sub.1 is a carbamoyloxy or ureido linking group, A is an oxa, imino or ureido group, R.sub.3 is hydrogen or methyl, R.sub.4 is hydrogen, or when R.sub.3 is hydrogen, methyl or also --COOR.sub.5 where R.sub.5 is hydrogen or lower alkyl, and crosslinked hydrogel contact lenses made therefrom and their preparation.

Copper phthalocyanine pigment systems with improved rheological and optical performance characteristics comprising copper phthalocyanine or halogen-substituted copper phthalocyanines blended with sulfonated copper phthalocyanine and provided with an anionic-cationic surfactant coating, and a process for the preparation thereof.

Oxime sulfonates of formula I ##STR1## wherein Y is a polymerizable unsaturated group or epoxide group or an --OH, --NHR.sup.5, --COOH, COOR.sup.6, --COCl, --CH.sub.2 Hal, --SO.sub.2 Cl or --NCO group, Z is an (x+y)-valent connecting member, R.sup.1 and R.sup.2 are monovalent organic radicals, m is 0 or 1, x is 1 or 2 and y is 1 or 2, can be converted into polymers which can be thermally or photochemically dissociated to form free sulfonic acid groups. Said polymers can therefore be used as photoresists which can be developed with aqueous alkalis.

The invention relates to material containing aldosemarcaptals of the formula I ##STR1## wherein n can be an integer from 2 to 6, and wherein R.sup.1 and R.sup.2 are identical or different, and in each case are C.sub.1 -C.sub.18 -alkyl, which is unsubstituted, substituted or interrupted by --O-- or --S--, or are --(CH.sub.2).sub.r --CO--N(C.sub.1 -C.sub.17 -alkyl).sub.2, r being 1 or 2, or are phenyl, benzyl or --(CH.sub.2).sub.r --CO--O--R.sup.3, in which r can be 1 or 2 and R.sup.3 is an alkali metal or C.sub.1 -C.sub.14 -alkyl; also wherein R.sup.1 and R.sup.2 are --CH.sub.2 --CH(OH)--R.sup.4, in which R.sup.4 is hydrogen, or C.sub.1 -C.sub.16 -alkyl, unsubstituted or substituted by --OH, or --CH.sub.2 --Y--(C.sub.1 -C.sub.15 -alkyl), in which Y is --O-- or --S--; or wherein R.sup.1 and R.sup.2 together form --(CH.sub.2).sub.m --, in which m can be an integer from 2 to 4; to the use of the aldosemercaptals in lubricants and hydraulic fluids which can be based on oil or water or mixtures thereof, or in plastics; and to some novel aldosemercaptals.

The invention relates to novel substituted 1,3,5-oxadiazin-2-ones of the formula ##STR1## wherein R.sub.1 and R.sub.4 are each independently of the other C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 alkynyl, phenyl, or benzyl; R.sub.2 and R.sub.3 are each independently of the other hydrogen, C.sub.1 -C.sub.4 alkyl, or R.sub.2 and R.sub.3, together with the carbon atom to which they are attached, are C.sub.3 -C.sub.6 cycloalkyl; and n is 0, 1 or 2; to the preparation of these compounds and to compositions containing them for use in pest control, in particular for controlling insects and representatives of the order Acarina that attack plants and animals. In particular, the novel compounds are very effective against plant-destructive sucking and feeding insects.

The invention relates to a novel microorganism of the genus Rhodococcus, to the use thereof in a process for the microbiological degradation of amino-s-triazines and cyanuric acid in wastewaters, as well as to a process for the microbiological degradation of s-triazine derivatives to biomass or to degradation products such as NH.sup.30.sub.4 and/or chloride, which comprises the combined use of said microorganism with Pseudomonas spp.

The invention relates to novel phenylcarbamoylbarbituric acid derivatives of the general formula ##STR1## wherein R.sub.1 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.3 alkoxy, allyl or C.sub.3 -C.sub.6 cycloalkyl, R.sub.2 is C.sub.1 -C.sub.4 alkyl or allyl, R.sub.3 is an unsubstituted or substituted heteroaromatic 6-membered ring which contains 2 or 3 nitrogen atoms, or is an unsubstituted or substituted heteroaromatic 6-membered ring which is fused to a benzene ring and which contains 1 to 3 nitrogen atoms, R.sub.4 and R.sub.5 are each independently of the other hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.3 haloalkyl and X is an oxygen or sulfur atom, and to the tautomers and salts thereof. These compounds may be used for controlling helminths which are parasites of animals.

Various substituted aminoxy alkylamine derivatives are effective in stabilizing organic materials against oxidative, thermal and actinic degradation, said derivatives being particularly effective as color improvers and process stabilizers in organic materials containing phenolic antioxidants and/or metal salts of fatty acids and/or hindered amine light stabilizers and/or organic phosphorus compounds; and certain of said derivatives as new compounds.

Zinc compounds of formula II wherein y is 1 or 2 and L is a solvent ligand selected from the group of the N-disubstituted acid amides, N-substituted lactams and the organic sulfoxides, are suitable for reaction with CO.sub.2, COS or SO.sub.2 to give, after working up, the acids of formula I wherein X is --CO.sub.2 H, --CSOH or --SO.sub.2 H, in good yield.

The invention relates to novel heterocyclic organosilyl compounds of the general formula I ##STR1## wherein R.sub.1 is hydrogen, C.sub.1 -C.sub.10 alkyl, C.sub.3 -C.sub.7 cycloalkyl, phenyl or trimethylsilyl, R.sub.2 is hydrogen or C.sub.1 -C.sub.4 alkyl, or R.sub.1 and R.sub.2 together form a saturated or unsaturated ring containing 6 carbon atoms; R.sub.3 and R.sub.4 are each independently of the other hydrogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy, and R.sub.4 may also be C.sub.3 -C.sub.7 cycloalkyl; R.sub.5 to R.sub.12 are each independently hydrogen or C.sub.1 -C.sub.4 alkyl, and R.sub.8 and R.sub.9 together may also form a saturated or unsaturated ring containing 6 carbon atoms; X is CH.sub.2, oxygen or sulfur, and n and Z are each independently of the other 0 or 1, and, if Z is 0, to the acid addition salts thereof. The novel compounds have microbicidal properties and are suitable in particular for controlling phytopathogenic microorganisms.

The invention relates to novel 5-(azolyloxyphenylcarbamoyl)barbituric acid derivatives of the general formula I ##STR1## wherein X is oxygen or sulfur; R.sub.1 is C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.3 -C.sub.6 cycloalkyl or allyl; R.sub.2 is C.sub.1 -C.sub.6 alkyl or allyl; R.sub.3 is an unsubstituted or substituted five-membered azole ring which is bound through carbon and is selected from the group consisting of benzimadazole, benzoxazole, benzothiazole, imidazole, oxazole, thiazole, oxadiazole, thiadiazole and triazole; and R.sub.4 and R.sub.5 are each independently of the other hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.1 -C.sub.6 alkoxy or C.sub.1 -C.sub.6 haloalkoxy; and to the tautomers and salts thereof, as anthelmintic compounds. Together with suitable carriers and further assistants, these compounds may be used in particular for controlling helminths which are parasites of animals.

A method of inhibiting the deposition of paraffin wax, asphaltene, or mixtures thereof in a crude oil contaminated with paraffin wax, asphaltene, or mixtures thereof and susceptible to such depositions comprising the step of incorporating into said crude oil an effective deposition inhibiting amount of an oil soluble organic compound having at least one oleophobic and hydrophobic fluoroaliphatic group, and antideposition stabilized crude oil compositions containing said compound, are disclosed.

A method of reducing a viscosity of asphaltenic crude oils by incorporating into said crude oil an effective viscosity reducing amount of an oil soluble organic compound having at least one oleophobic and hydrophobic fluoroaliphatic group, and optionally a low viscosity diluent, and compositions thereof.

A method of laser marking ceramic materials, glazes, glass ceramics and glasses that contain at least one radiation-sensitive additive, utilizing a laser beam as radiation energy source which is either applied to, or focused on, the surface of the material to be marked in accordance with the form of the graphic symbols to be reproduced, such that a change in color is induced at the irradiated areas, wherein the wavelength of said laser beam used as energy source is in the near UV and/or visible range and/or infra-red range, and the radiation-sensitive additive is an inorganic pigment.

The invention relates to compositions of a soluble polyimide and polypyrrole. These compositions can preferably be prepared by anodic oxidation of pyrrole or a pyrrole derivative at electrodes coated with polyimide. They make it possible to prepare free standing electrically conductive films.

Compounds of the general formula I ##STR1## in which R.sup.1 is hydrogen, C.sub.1 -C.sub.12 -alkyl, C.sub.5 -C.sub.7 -cycloalkyl, phenyl or benzyl and R.sup.2 is hydrogen or C.sub.1 -C.sub.4 -alkyl, or R.sup.1 and R.sup.2, together with the C atom to which they are attached, form a 5-membered or 6-membered ring, and R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are identical or different and are hydrogen, C.sub.1 -C.sub.12 -alkyl, phenyl which is unsubstituted or monosubstituted to trisubstituted by C.sub.1 -C.sub.4 -alkyl, halogen or C.sub.1 -C.sub.4 -alkoxy, or is a group of the formula --CH.sub.2 OR.sup.7 (II) in which R.sup.7 is C.sub.1 -C.sub.12 -alkyl, phenyl which is unsubstituted or monosubstituted to trisubstituted by C.sub.1 -C.sub.4 -alkyl, halogen or C.sub.1 -C.sub.4 -alkoxy, or is --C(O)--R.sup.8, and R.sup.8 is C.sub.1 -C.sub.12 -alkyl, and also not more than two of the radicals R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are one or two groups of the formula --CH.sub.2 CH.sub.2 Si(OR.sup.9).sub.3 (III), --CH.sub.2 OC(O)CH.sub.2 CH.sub.2 Si(OR.sup.9).sub.3 (IV), --CH.sub.2 O(C.sub.m H.sub.2m)Si(OR.sup.9).sub.3 (V) or ##STR2## in which R.sup.9 is C.sub.1 -C.sub.4 -alkyl or phenyl and m is a number from 1 to 8 and r is a number 1 or 2 and t is 0, 1 or 2 and R.sup.1 is as defined above, and, in addition, compounds of the formula I in which R.sup.4 and R.sup.5 together form a group of the formula ##STR3## in which R.sup.9 is as defined above and R.sup.3 and R.sup.6 in this case are hydrogen and n is 1 or 2 and, if n is 1, Z is an organic radical which is derived from a primary amine ZnH.sub.2 and can contain one or two --Si(OR.sup.9).sub.3 groups and, if n is 2, Z is a divalent organic radical derived from a diprimary diamine H.sub.2 NZNH.sub.2 ; subject to the proviso that the compounds of the formula I contain one to three --Si(OR.sup.9).sub.3 groups, are suitable for use as adhesion promoters, particularly for moisture-curing epoxide and polyurethane resins.

An esterification process particularly for the preparation of rosin esters, polyesters and polymeric esters wherein aliphatic or aromatic carboxylic acids are reacted with appropriate alcohols in the presence of catalytic amounts of a mixture of a calcium hydroxyaryl phosphonate and an organosilicon heterocycle, the presence of said mixture serving to reduce the time necessary for complete esterification and to provide esters with increased oxidation stability and better color.