Composition for rheology control

Abstract

The invention relates to a rheology control agent containing i) 15-95% by weight of an amide compound (A), ii) 5-75% by weight of a urea compound (B), iii) 0-50% by weight of an ionogenic compound (C) and iv) 0-35% weight of an organic solvent (D).

Claims

1. A composition comprising i) 15-95 wt % of an amide compound (A), ii) 5-75 wt % of a urea compound (B), iii) 0-50 wt % of an ionogenic compound (C), and iv) 0-35 wt % of an organic solvent (D), where the amide compound (A) has a molar mass of 70 to 600 g/mol, the amide compound (A) contains not more than one amide group with hydrogen bonded to its nitrogen atom, the amide compound (A) has no urea group, no phosphorus, no silicon, and no halogen, and the amide compound (A) is present in accordance with the general formula (I), ##STR00013## where Xx is identical or different and is represented by an amide group C(O)N which is linked to Rz, Ra, and Rb in accordance with one of the general formulae RzC(O)NRaRb (Xx1), RaC(O)NRzRb (Xx2), and RbC(O)NRzRa (Xx3) Xy is identical or different and is represented by an amide group C(O)N which is linked to Rz, Rc, and Rd in accordance with one of the general formulae RzC(O)NRcRd (Xy1), RcC(O)NRzRd (Xy2), and RdC(O)NRzRc (Xy3) Rz in each case is identical or different and is represented by a branched or unbranched, saturated or unsaturated hydrocarbon radical which has 1 to 32 carbon atoms and which as heteroatom-containing groups may optionally contain exclusively amino groups, amide groups, or mixtures thereof Ra, Rb, Rc, and Rd, in each case identically or differently and in each case independently of one another, are represented by hydrogen or a branched or unbranched, saturated or unsaturated organic radical containing 1 to 16 carbon atoms, with the proviso that Ra, Rb, Re, and Rd in their entirety have at least four carbon atoms, not more than one of the radicals from the group of Ra, Rb, Rc, and Rd is present in the form of hydrogen, at least one of i) Ra and Rb, together with the CON moiety joining Ra to Rb or ii) Re and Rd, together with the CON moiety joining Rc to Rd, may optionally together, in accordance with the general formula (-1), form a cyclic structure having 4 to 10 ring atoms, and ##STR00014## at least one of iii) Ra and Rb, together with the N atom joining Ra to Rb or iv) Rc and Rd, together with the N atom joining Rc to Rd, may optionally together, in accordance with the general formula (-1), form a cyclic structure having 4 to 7 ring atoms, or ##STR00015## Rb and Rc together with the N atom bonded to each of Rb and Rc, and also with the radical Rz, may optionally, in accordance with the general formula (-1), form a cyclic structure having 5 to 7 ring atoms ##STR00016## Ra, Rb, Re, Rd, and Rz in their entirety have not more than 36 carbon atoms and also not more than 8 heteroatoms from the group of N and O, the urea compound (B) has a molecular weight of at least 350 g/mol and at least one urea group, the ionogenic compound (C) contains a cationic component and an anionic component and is different from the amide compound (A) and from the urea compound (B), and the organic solvent (D) contains no urea group and no ionic group and also has not more than two heteroatoms selected from the group consisting of nitrogen and oxygen.

2. The composition as claimed in claim 1, comprising i) 30-90 wt % of the amide compound (A), ii) 8-55 wt % of the urea compound (B), iii) 0-15 wt % of the ionogenic compound (C), and iv) 2-25 wt % of the organic solvent (D).

3. The composition as claimed in claim 1, characterized in that 50-100 wt % of the amide compound (A) has no amide group with hydrogen bonded to its nitrogen atom.

4. The composition as claimed in claim 3, characterized in that said 50-100 wt % of the amide compound (A) is present in accordance with a general formula (I) in which none of the radicals from the group of Ra, Rb, Rc, and Rd is represented by hydrogen.

5. The composition as claimed in claim 1, characterized in that 50-100 wt % of the amide compound (A) is present in accordance with the general formula (Ia) ##STR00017##

6. The composition as claimed in claim 1, characterized in that 50-100 wt % of the amide compound (A) is present in accordance with the general formula (Ia), where at least one of i) Ra and Rb, together with the N atom joining Ra to Rb or ii) Rc and Rd, together with the N atom joining Rc to Rd, in accordance with the general formula (-1), together form a branched or unbranched, saturated or unsaturated cyclic structure having 4 to 7 ring atoms which has not more than two heteroatoms from the group consisting of O and N.

7. The composition as claimed in claim 1, characterized in that 50-100 wt % of the amide compound (A) is present in accordance with the general formula (Ia), where i) Ra, Rb, Rc or Rd, or ii) Ra, Rb, Rc and Rd, in each case are not present in cyclic structures.

8. The composition as claimed in claim 1, characterized in that the general formula (I) for 50-100 wt % of the amide compound (A) is present in accordance with the general formula (Ib) ##STR00018##

9. The composition as claimed in claim 1, characterized in that the general formula (I) for 50-100 wt % of the amide compound (A) is present in accordance with the general formula (Ib), where Rb and Rc together with the N atom bonded to each of Rb and Rc, and also with the radical Rz, in accordance with the general formula (-1), form a branched or unbranched, saturated or unsaturated cyclic structure having 5 to 7 ring atoms which has not more than two heteroatoms from the group consisting of O and N.

10. The composition as claimed in claim 1, characterized in that the general formula (I) for 50-100 wt % of the amide compound (A) is present in accordance with the general formula (Ib), where at least one of i) Ra and Rb, together with the CON moiety joining Ra to Rb or ii) Rc and Rd, together with the CON moiety joining Rc to Rd, in accordance with the general formula (-1), together form a branched or unbranched, saturated or unsaturated cyclic structure having 4 to 10 ring atoms which has not more than two heteroatoms from the group consisting of O and N.

11. The composition as claimed in claim 1, characterized in that 70-100 wt % of the urea compound (B) either has at least two urea groups or has at least one urea group and at least one urethane group.

12. The composition as claimed in claim 1, characterized in that 50-100 wt % of the urea compound (B) is present in accordance with the general formula (II)
R.sup.31[R.sup.33ZR.sup.34W].sub.nR.sup.32 (II) where R.sup.31 and R.sup.32 each identically or differently and also each independently of one another are represented by a branched or unbranched, saturated or unsaturated organic radical which contains 1-100 carbon atoms and which has not more than one urea group each and not more than one urethane group each, R.sup.33 and R.sup.34 each identically or differently and also each independently of one another are represented by branched or unbranched polyester radicals containing 1-300 carbon atoms and optionally containing ether groups, branched or unbranched polyether radicals containing 2-300 carbon atoms, branched or unbranched polyamide radicals containing 1-300 carbon atoms, polysiloxane radicals containing 3 to 100 silicon atoms, branched or unbranched C2-C22 alkylene radicals, branched or unbranched C3-C18 alkenylene radicals, C5-C12 arylene radicals, or branched or unbranched C7-C22 arylalkylene radicals, Z and W each identically or differently and also each independently of one another are represented by NHCOO or NHCONH, n is in each case identical or different and is represented by an integer from 1 to 150.

13. The composition as claimed in claim 1, characterized in that 50-100 wt % of the urea compound (B) has a molecular weight of 2000 to 55000 and also 4-150 urea groups.

14. The composition as claimed in claim 1, characterized in that 50-100 wt % of the urea compound (B) is present in accordance with one of the general formulae selected from the group consisting of (IIIa), (IIIb), (IIIc), and (IIId) ##STR00019## where AM is identical or different and is represented by a linear or branched, saturated or unsaturated, aliphatic, aromatic or aliphatic-aromatic organic radical having 2 to 50 carbon atoms, AM1 and AM2 are identical or different and independently of one another represented by a linear or branched, saturated or unsaturated, aliphatic, aromatic or aliphatic-aromatic organic radical having 1 to 50 carbon atoms, IC1 and IC2 are identical or different and independently of one another represented by a linear or branched, saturated or unsaturated, aliphatic, aromatic or aliphatic-aromatic hydrocarbon radical having 2 to 40 carbon atoms, IC3 is identical or different and is represented by a linear or branched, saturated or unsaturated, aliphatic, aromatic or aliphatic-aromatic hydrocarbon radical having 2 to 24 carbon atoms, RP1 and RP2 are identical or different and independently of one another represented by a linear or branched, saturated or unsaturated, aliphatic, aromatic or aliphatic-aromatic organic radical having 1 to 24 carbon atoms or by a polyether radical having 1 to 120 ether oxygen atoms or by a polyester radical having 1 to 100 ester groups and optionally containing ether groups, or by a polyamide radical having 1 to 100 amide groups, or by a polysiloxane radical having 3 to 100 silicon atoms, RP3 is identical or different and is represented by a linear or branched, saturated or unsaturated, aliphatic, aromatic or aliphatic-aromatic hydrocarbon radical having 2 to 24 carbon atoms or by a (poly)ether radical having 1 to 120 ether oxygen atoms or by a polyamide radical having 1 to 100 amide groups or by a polysiloxane radical having 3 to 100 silicon atoms or by a polyester radical having 1 to 100 ester groups and optionally containing ether groups, and p is identical or different and is represented by 0 or 1.

15. The composition as claimed in claim 14, characterized in that 70-100 wt % of the urea compound (B) is present in each case in accordance with one of the general formulae selected from the group consisting of (IIIa), (IIIb), (IIIb), and (IIId), where AM is identical or different and is selected from the group consisting of ##STR00020## where R.sub.x and Ry are identical or different and are in each case independently represented by CH.sub.3 or hydrogen,
(CH.sub.2).sub.q where q is identical or different and is represented by an integer from 2 to 12, AM1 and AM2 are each identical or different and are selected from the group consisting of n-propyl, isopropyl, butyl, isobutyl, tert-butyl, lauryl, oleyl, stearyl, polyisobutylene, and polyethers having 2 to 40 ether oxygen atoms, benzyl, methylbenzyl, cyclohexyl, carboxyalkyl, hydroxyalkyl, and alkylalkoxysilane, IC1 and IC2 are each identical or different and are selected from the group consisting of ##STR00021## IC3 is identical or different and is selected from the group consisting of methyl, ethyl, phenyl, benzyl, cyclohexyl, and stearyl, RP1 and RP2 are each identical or different and are selected from the group consisting of branched or unbranched C1 to C18 alkyl, oleyl, benzyl, allyl, polyether radical optionally containing structural units of ethylene oxide, propylene oxide, butylene oxide or mixtures thereof, and polyester radical containing structural units of epsilon-caprolactone, delta-valerolactone or mixtures thereof, RP3 is identical or different and is selected from the group consisting of linear or branched C1 to C18 alkylene, linear or branched C2 to C18 alkenylene, polyether optionally containing structural units of ethylene oxide, propylene oxide, butylene oxide or mixtures thereof and having 1 to 25 ether oxygen atoms.

16. The composition as claimed in claim 1, characterized in that 70-100 wt % of the urea compound (B) in each case is prepared by reaction of monofunctional amines with isocyanates oligomerized by isocyanurate formation or uretdione formation, or by isocyanurate formation and uretdione formation.

17. The composition as claimed in claim 1, characterized in that 95-100 wt % of the urea compound (B) contains in each case at least one molecule segment of the general formula (IVa)
OCONHY.sub.1NHCONH(IVa) where Y.sub.1 is identical or different and is represented by a saturated or unsaturated, branched or unbranched hydrocarbon radical containing 6 to 20 carbon atoms, and in each case contains no molecule segment of the general formula (IVb)
OCONHY.sub.2NHCOO(IVb) where Y2 is identical or different and is represented by a saturated or unsaturated, branched or unbranched hydrocarbon radical containing 6 to 20 carbon atoms.

18. The composition as claimed in claim 1, comprising 0.5-4.0 wt % of the ionogenic compound (C), where 50-100 wt % of the ionogenic compound (C) is present in the form of lithium salt or calcium salt, optionally in the form of a chloride, acetate, nitrate, or mixtures thereof.

19. The composition as claimed in claim 1, which is suitable for rheology control or for thixotroping of liquid systems.

20. The composition as claimed in claim 1, characterized in that 50-100 wt % of the amide compound (A) is present in accordance with a general formula (I) in which none of the radicals from the group of Ra, Rb, Rc, and Rd is represented by hydrogen.

21. A method comprising adding the composition of claim 1 to a liquid mixture for rheology control or thixotroping, characterized in that the liquid mixture is present in the form of a coating, a paint or varnish, a plastics formulation, a pigment paste, a sealant formulation, cosmetics, a ceramic formulation, an adhesive formulation, an encapsulating composition, a drilling mud solution, a building material formulation, a lubricant, a filling compound, a printing ink or a liquid ink.

22. A preparation which is present in the form of a paint or varnish, a plastics formulation, a pigment paste, a sealant formulation, cosmetics, a ceramic formulation, an adhesive formulation, an encapsulating composition, a building material formulation, a lubricant, a drilling mud solution, a filling compound, a printing ink or a liquid ink and to which 0.1 to 7.5 wt % of a composition as claimed in claim 1 has been added.

Description

COMPARATIVE EXAMPLES (NOT INVENTIVE)

Comparative Example C1

(1) Stage 1

(2) First of all 64.4 g of a diisocyanate monoadduct are prepared in accordance with patent specification EP 1188779 from a polyethylene glycol monobutyl ether having a hydroxyl number of 220 mg KOH/g (determined according to DIN/ISO 4629) and a mixture of 35% 2,4-tolylene diisocyanate and 65% 2,6-tolylene diisocyanate.

(3) Stage 2

(4) A four-neck flask is provided with stirrer, dropping funnel, thermometer, and reflux condenser. It is charged with 72.7 g of 1-ethylpyrrolidin-2-one, which is heated under a nitrogen atmosphere with stirring to 120 C. 4.2 g of lithium chloride are added and at this temperature are dissolved with stirring in one hour.

(5) Temperature is then lowered to 80 C. 10.2 g of m-xylylenediamine are added and the mixture is homogenized.

(6) The isocyanate adduct prepared beforehand (stage 1) is added dropwise with stirring over the course of 1 hour to the amine solution at a slow rate such that the temperature does not exceed 85 C. To complete the reaction, the reaction mixture is stirred at 80 C. for a further three hours. A clear, yellow product is obtained. The amine number is 1 mg KOH/g (determined according to DIN 16945). The product contains 49 wt % of the urea compound.

Comparative Example C2

(7) Stage 1

(8) First of all 64.4 g of a diisocyanate monoadduct are prepared in accordance with patent specification EP 1188779 from a polyethylene glycol monobutyl ether having a hydroxyl number of 220 mg KOH/g (determined according to DIN/ISO 4629) and a mixture of 35% 2,4-tolylene diisocyanate and 65% 2,6-tolylene diisocyanate.

(9) Stage 2

(10) A four-neck flask is provided with stirrer, dropping funnel, thermometer, and reflux condenser. It is charged with 72.7 g of dimethyl sulfoxide, which is heated under a nitrogen atmosphere with stirring to 120 C. 4.2 g of lithium chloride are added and at this temperature are dissolved with stirring in one hour. Temperature is then lowered to 80 C. 10.2 g of m-xylylenediamine are added and the mixture is homogenized.

(11) The isocyanate adduct prepared beforehand (stage 1) is added dropwise with stirring over the course of 1 hour to the amine solution at a slow rate such that the temperature does not exceed 85 C. To complete the reaction, the reaction mixture is stirred at 80 C. for a further three hours. A clear, yellow product is obtained. The amine number is 1 mg KOH/g (determined according to DIN 16945). The product contains 49 wt % of the urea compound.

Comparative Example C3

(12) Stage 1

(13) First of all 64.4 g of a diisocyanate monoadduct are prepared in accordance with patent specification EP 1188779 from a polyethylene glycol monobutyl ether having a hydroxyl number of 220 mg KOH/g (determined according to DIN/ISO 4629) and a mixture of 35% 2,4-tolylene diisocyanate and 65% 2,6-tolylene diisocyanate.

(14) Stage 2

(15) A four-neck flask is provided with stirrer, dropping funnel, thermometer, and reflux condenser. It is charged with 72.7 g of N-methylpyrrolidone, which is heated under a nitrogen atmosphere with stirring to 120 C. 4.2 g of lithium chloride are added and at this temperature are dissolved with stirring in one hour. Temperature is then lowered to 80 C. 10.2 g of m-xylylenediamine are added and the mixture is homogenized.

(16) The isocyanate adduct prepared beforehand (stage 1) is added dropwise with stirring over the course of 1 hour to the amine solution at a slow rate such that the temperature does not exceed 85 C. To complete the reaction, the reaction mixture is stirred at 80 C. for a further three hours. A clear, yellow product is obtained. The product contains 49 wt % of the urea compound.

Comparative Example C4

(17) First of all a monoadduct is prepared in accordance with patent specification EP 1188779 from 2,4-tolylene diisocyanate (Desmodur T100, Bayer) and lauryl alcohol. In a reaction vessel (round-bottom flask with stirrer, reflux condenser, and dropping funnel), under a nitrogen atmosphere and with stirring, 1.7 (0.039 mol) of LiCl are dissolved in 75 g of N-methylpyrrolidone (commercial product). Then 3.6 g (0.026 mol) of meta-xylylenediamine are added and the clear mixture is heated to 80 C. Subsequently 19.8 g (0.052 mol) of the monoadduct of Desmodur T100 and lauryl alcohol are added dropwise with stirring over the course of 1 hour at a rate such that the temperature does not exceed 85 C. To complete the reaction, the reaction mixture is stirred at 80 C. for 3 hours. A clear and liquid product is obtained. The fraction of the urea compound in the resulting product is 23 wt %.

Comparative Example C5

(18) First of all a monoadduct is prepared in accordance with patent specification EP 1188779 from 2,4-tolylene diisocyanate (Desmodur T100, Bayer) and lauryl alcohol. In a reaction vessel (round-bottom flask with stirrer, reflux condenser, and dropping funnel), under a nitrogen atmosphere and with stirring, 1.7 g (0.039 mol) of LiCl are dissolved in 75 g of 1-N-ethylpyrrolidone (commercial product). Then 3.6 g (0.026 mol) of meta-xylylenediamine are added and the clear mixture is heated to 80 C. Subsequently 19.8 g (0.052 mol) of the monoadduct of Desmodur T100 and lauryl alcohol are added dropwise with stirring over the course of 1 hour at a rate such that the temperature does not exceed 85 C. To complete the reaction, the reaction mixture is stirred at 80 C. for 3 hours. A clear and low-viscosity product is obtained. The fraction of the urea compound in the resulting product is 23 wt %.

Comparative Example C6

(19) Stage 1

(20) First of all 93.6 g of a monoadduct are prepared in accordance with patent specification EP 1188779 from a polyethylene glycol monomethyl ether having a molar mass of 450 g/mol and a mixture of 35% 2,4-tolylene diisocyanate and 65% 2,6-tolylene diisocyanate.

(21) Stage 2

(22) In a four-neck flask with stirrer, dropping funnel, thermometer, and reflux condenser, 99.7 g of N-methylpyrrolidone (commercial product, BASF) are heated to 100 C. and, when the temperature is reached, 4.2 g of lithium chloride are added. The lithium chloride is thereafter dissolved with stirring at 100 C. within one hour. The temperature is then lowered to 80 C.

(23) 10.2 g of m-xylylenediamine are added and the mixture is homogenized.

(24) The isocyanate adduct prepared beforehand (stage 1) is added dropwise with stirring over the course of 1 hour to the amine solution at a slow rate such that the temperature does not exceed 85 C. To complete the reaction, the reaction mixture is stirred at 80 C. for three hours. A clear, yellowish product is obtained. The product contains 48 wt % of urea compound.

Comparative Example C7

(25) Stage 1

(26) First of all 93.6 g of a monoadduct are prepared in accordance with patent specification EP 1188779 from a polyethylene glycol monomethyl ether having a molar mass of 450 g/mol and a mixture of 35% 2,4-tolylene diisocyanate and 65% 2,6-tolylene diisocyanate.

(27) Stage 2

(28) In a four-neck flask with stirrer, dropping funnel, thermometer, and reflux condenser, 132.0 g of dimethyl sulfoxide (commercial product from Sigma Aldrich) are heated to 100 C. and, when the temperature is reached, 4.2 g of lithium chloride are added. The lithium chloride is thereafter dissolved with stirring at 100 C. within one hour. The temperature is then lowered to 80 C.

(29) 10.2 g of m-xylylenediamine are added and the mixture is homogenized.

(30) The isocyanate adduct prepared beforehand (stage 1) is added dropwise with stirring over the course of 1 hour to the amine solution at a slow rate such that the temperature does not exceed 85 C. To complete the reaction, the reaction mixture is stirred at 80 C. for three hours. A clear, yellowish product is obtained. The product contains 43 wt % of urea compound.

Comparative Example C8

(31) Stage 1

(32) First of all 93.6 g of a monoadduct are prepared in accordance with patent specification EP 1188779 from a polyethylene glycol monomethyl ether having a molar mass of 450 g/mol and a mixture of 35% 2,4-tolylene diisocyanate and 65% 2,6-tolylene diisocyanate.

(33) Stage 2

(34) In a four-neck flask with stirrer, dropping funnel, thermometer, and reflux condenser, 99.7 g of N-ethylpyrrolidone (commercial product, BASF) are heated to 100 C. and, when the temperature is reached, 4.2 g of lithium chloride are added. The lithium chloride is thereafter dissolved with stirring at 100 C. within one hour. The temperature is then lowered to 80 C.

(35) 10.2 g of m-xylylenediamine are added and the mixture is homogenized.

(36) The isocyanate adduct prepared beforehand (stage 1) is added dropwise with stirring over the course of 1 hour to the amine solution at a slow rate such that the temperature does not exceed 85 C. To complete the reaction, the reaction mixture is stirred at 80 C. for three hours. A clear, yellowish product is obtained. The product contains 50 wt % of urea compound.

Comparative Example C11

(37) Stage 1

(38) First of all 64.4 g of a diisocyanate monoadduct are prepared in accordance with patent specification EP 1188779 from a polyethylene glycol monobutyl ether having a hydroxyl number of 220 mg KOH/g (determined according to DIN/ISO 4629) and a mixture of 35% 2,4-tolylene diisocyanate and 65% 2,6-tolylene diisocyanate.

(39) Stage 2

(40) A four-neck flask is provided with stirrer, dropping funnel, thermometer, and reflux condenser. It is charged with 118.2 g of methyl 5-(dimethylamino)-2-methyl-5-oxopentanoate, which is heated under a nitrogen atmosphere with stirring to 120 C. 4.2 g of lithium chloride are added and at this temperature are dissolved with stirring in one hour. Temperature is then lowered to 80 C. 10.2 g of m-xylylenediamine are added and the mixture is homogenized.

(41) The isocyanate adduct prepared beforehand (stage 1) is added dropwise with stirring over the course of 1 hour to the amine solution at a slow rate such that the temperature does not exceed 85 C. To complete the reaction, the reaction mixture is stirred at 80 C. for a further three hours. A clear, yellow product is obtained. The amine number is 1 mg KOH/g (determined according to DIN 16945). The product contains 38 wt % of the urea compound.

Comparative Example C12

(42) Stage 1

(43) First of all 64.4 g of a diisocyanate monoadduct are prepared in accordance with patent specification EP 1188779 from a polyethylene glycol monobutyl ether having a hydroxyl number of 220 mg KOH/g (determined according to DIN/ISO 4629) and a mixture of 35% 2,4-tolylene diisocyanate and 65% 2,6-tolylene diisocyanate.

(44) Stage 2

(45) A four-neck flask is provided with stirrer, dropping funnel, thermometer, and reflux condenser. It is charged with 118.2 g of 1-(morpholine-4-yl)ethanone, which is heated under a nitrogen atmosphere with stirring to 120 C. 4.2 g of lithium chloride are added and at this temperature are dissolved with stirring in one hour.

(46) Temperature is then lowered to 80 C. 10.2 g of m-xylylenediamine are added and the mixture is homogenized.

(47) The isocyanate adduct prepared beforehand (stage 1) is added dropwise with stirring over the course of 1 hour to the amine solution at a slow rate such that the temperature does not exceed 85 C. To complete the reaction, the reaction mixture is stirred at 80 C. for a further three hours. A clear, yellow product is obtained. The amine number is 1 mg KOH/g (determined according to DIN 16945). The product contains 38 wt % of the urea compound.

Comparative Example C13: Combination of Noninventive Amide Compounds with Urea Compounds

(48) For the following combination experiments, in analogy to WO 2011/091812, BYK-430 (30% strength solution of a high-molecular modified polyamide, from BYK-Chemie GmbH) is used as noninventive amide compound. This amide component was combined with various urea compounds in accordance with comparative examples above (i.e., dissolved urea compounds containing no inventive amide component as a mixing constituent). Mixing was carried out with continuous stirring.

(49) TABLE-US-00002 Weight ratio of Appearance urea solution to of the Ex. Urea solution BYK-430 combination C13-1 C3 (410) 7:3 slightly cloudy, gelled C13-2 C3 (410) 5:5 slightly cloudy, gelled C13-3 C3 (410) 3:7 very cloudy, gelled C13-4 C6 (420) 7:3 slightly cloudy, gelled C13-5 C6 (420) 5:5 cloudy, gelled C13-6 C6 (420) 3:7 cloudy, gelled

(50) The example shows that the compositions of the invention ensure high compatibility of the relevant urea and amide components, leading to ease of preparation combined with good storage stability of the rheologically active compositions comprising amide and urea, whereas the noninventive amide compounds do not enable a storage-stable combination and therefore also do not enable easy handling as a whole composition. In the case of the noninventive combinations, therefore, incorporation into the system must always take place separately, meaning that more worksteps and therefore extra production effort and complexity are required.

(51) Performance Testing of the Compositions Suitable as Rheology Additives

(52) Test System 1: Solvent Mixture of n-Butyl Acetate and Methoxypropanol

(53) For this series of tests an amount of the urea compound of 28 wt % in the additive composition is set for all of the products tested, by the addition to the compositionwhere necessaryof a further quantity of the respective amide compound. In a 100 ml glass bottle, 50 g of the solvent mixture n-butyl acetate/Dowanol PM 75:25 (w/w) are introduced, and then the respective additive composition is added in an amount corresponding to 0.5 wt % of the urea compound. This incorporation takes place with stirring with the Dispermat CV (toothed disk d=2.5 cm at 1000 rpm). The addition is followed by a further minute of stirring. The samples are then left to stand at RT for one hour, after which a visual appraisal is made of the gel strength, as a measure of the rheological activity, and of the clouding, for the compatibility of the additive.

(54) Evaluation Scale:

(55) TABLE-US-00003 Gel strength: 1 very strong 2 strong 3 moderate 4 very weak 5 no gel Cloudiness 1 clear (compatibility): 2 slightly cloudy 3 cloudy 4 very cloudy 5 extremely cloudy
Results:

(56) TABLE-US-00004 Composition (each containing Gel 28 wt % of urea) strength Cloudiness Control 5 1 Comparative Ex. C1 4 2 K1 3 1 K2 3 1 K4 4 1 K3 4 1 K6 3 2

(57) From the results it is evident that the inventive compositions in comparison to comparative example C1 permit either better compatibility (i.e., less cloudiness in the system) or the development of a greater gel strength (i.e., better rheological activity) or exhibit both advantageous effects in combination.

(58) Test System 2: Setalux D A 870 BA Clear Coat

(59) For this series of tests an amount of the urea compound of 28 wt % in the additive composition is set for all of the products tested, by the addition to the compositionwhere necessaryof a further quantity of the respective amide compound. In a 100 ml glass bottle, 50 g of Setalux D A 870 BA clear coat are introduced and then the respective additive is incorporated with stirring using the Dispermat CV (toothed disk d=2.5 cm at 1000 rpm). The amount of the additive composition is selected in each case to correspond to 0.4 wt %, relative to the urea compound. The addition is followed by stirring for a further minute.

(60) The samples are then left to stand at RT for one day, after which they are first appraised visually for the gel strength, as a measure of the rheological activity, and for cloudiness, for the compatibility of the additive. This is followed by testing of the sag resistance, as a measure of the rheological activity under application conditions.

(61) For this purpose, the sample is stirred evenly with a spatula and then applied to contrast charts using the 30-300 m stepped doctor and an automatic applicator from BYK Gardner, at a speed of 5 cm/s. Following application, the contrast charts are hung up directly, in horizontal position, for drying. After drying has taken place, a determination is made of the wet film thickness, in m, at which the coating does not run, meaning that no runs or fat edging are apparent. The higher the figure for the sag resistance for a given active substance employed, the better the rheological activity.

(62) Coating Formulation (Parts by Weight):

(63) TABLE-US-00005 Setalux D A 870 BA 80.0 Butyl acetate 9.9 Dowanol PMA 9.9 BYK-066 0.2
Results:

(64) TABLE-US-00006 Composition Sag (each containing Gel resistance 28 wt % of urea) strength Cloudiness m wet Control 5 1 30 Comparative Ex. C3 2 2 90 K1 1 1 150 K2 1 2 450 K4 2 1 200 K3 1-2 2 400

(65) From the results it is apparent that the inventive compositions in comparison to comparative example C3 allow either better compatibility (i.e., less cloudiness in the system) or the development of a greater gel strength and also an improved sag resistance (i.e., maximum possible film thickness) or exhibit the advantageous effects in combination.

(66) Test System 3: Epikote 1001-X75Clear Coat

(67) For this series of tests an amount of the urea compound of 38 wt % in the additive composition is set for all of the products tested, by the addition to the compositionwhere necessaryof a further quantity of the respective amide compound. In a 100 ml glass bottle, 50 g of Epikote 1001-X75 clear coat are introduced and then the respective additive is incorporated with stirring using the Dispermat CV (toothed disk d=2.5 cm at 1000 rpm). The amount selected in each case corresponds to 0.8 wt % of the urea compound. The addition is followed by stirring for a further minute. The samples are then left to stand at RT for one day, after which they are first appraised visually for the gel strength, as a measure of the rheological activity, and for cloudiness, for the compatibility of the additive. This is followed by testing of the sag resistance, as a measure of the rheological activity under application conditions.

(68) For this purpose, the sample is stirred evenly with a spatula and then applied to contrast charts using the 30-300 m stepped doctor and an automatic applicator from BYK Gardner, at a speed of 5 cm/s. Following application, the contrast charts are hung up directly, in horizontal position, for drying. After drying has taken place, a determination is made of the wet film thickness, in m, at which the coating does not run, meaning that no runs or fat edging are apparent. The higher the figure for the sag resistance for a given active substance employed, the better the rheological activity.

(69) Coating Formulation (Parts by Weight):

(70) TABLE-US-00007 Epikote 1001-X75 75.3 Methyl isobutyl ketone 17.3 Isobutanol 7.4
Results:

(71) TABLE-US-00008 Composition Sag (each containing Gel resistance 38 wt % of urea) strength Cloudiness m wet Control 5 1 <50 Comparative Ex. C3 3 1 200 K1 2 1 300

(72) From the results it is apparent that the inventive composition in comparison to comparative example C3, while having equally good compatibility, permits a greater gel strength and also an improved sag resistance (i.e., maximum possible film thickness).

(73) Test System 4: Worleekyd S 351 Binder

(74) In a 100 ml glass bottle, 50 g of Worleekyd S 351 binder are introduced and then the respective additive is incorporated with stirring using the Dispermat CV (toothed disk d=2.5 cm at 1000 rpm). The amount selected in each case corresponds to 0.7 wt % of the urea compound. The addition is followed by stirring for a further minute.

(75) The samples are then left to stand at RT for one day, after which an assessment is made of the sag resistance, as a measure of the rheological activity under application conditions. For this purpose, the sample is stirred evenly with a spatula and then applied to contrast charts using the 50-500 m stepped doctor and an automatic applicator from BYK Gardner, at a speed of 5 cm/s. Following application, the contrast charts are hung up directly, in horizontal position, for drying. After drying has taken place, a determination is made of the wet film thickness, in m, at which the coating does not run, meaning that no runs or fat edging are apparent. The higher the figure for the sag resistance for an identical active substance employed, the better the rheological activity.

(76) Results:

(77) TABLE-US-00009 Composition Sag (each containing Gel resistance 23 wt % of urea) strength Cloudiness m wet Control 5 1 <50 Comparative Ex. C4 3 3 300 Comparative Ex. C5 3-4 3 350 K7 1 2 450

(78) From the results it is apparent that the inventive composition in comparison to comparative examples C4 and C5, while having equally improved compatibility, permits a greater gel strength and also an improved sag resistance (i.e., maximum possible film thickness).

(79) Test System 5: Worleekyd S 366 Clear Coat

(80) In a 100 ml glass bottle, 50 g of Worleekyd S 366 clear coat are introduced and then the respective additive is incorporated with stirring using the Dispermat CV (toothed disk d=2.5 cm at 1000 rpm). The amount selected in each case corresponds to 0.5 wt % of the urea compound. The addition is followed by stirring for a further minute. The samples are then left to stand at RT for one day, after which an assessment is made of the sag resistance, as a measure of the rheological activity under application conditions.

(81) For this purpose, the sample is stirred evenly with a spatula and then applied to contrast charts using the 50-500 m stepped doctor and an automatic applicator from BYK Gardner, at a speed of 5 cm/s. Following application, the contrast charts are hung up directly, in horizontal position, for drying. After drying has taken place, a determination is made of the wet film thickness, in m, at which the coating does not run, meaning that no runs or fat edging are apparent. The higher the figure for the sag resistance for a given active substance employed, the better the rheological activity.

(82) Coating Formulation (Parts by Weight):

(83) TABLE-US-00010 Worlekyd S 366 60% in Isopar H 80.9 Isopar H 16.0 Nuodex Combi APB 2.6 Borchi Nox M 2 0.3 BYK-066 0.2
Results:

(84) TABLE-US-00011 Composition Sag (each containing Gel resistance 23 wt % of urea) strength m wet Control 5 50 Comparative Ex. C4 3-4 150 K7 1 300

(85) From the results it is apparent that the inventive composition in comparison to comparative example C4, permits a significantly increased gel strength and also improved sag resistance (i.e., maximum possible film thickness).

(86) Test System 6: Polystyrene Palapreg P17-02/Palapreg H 814-01

(87) In a 175 ml PE beaker, first of all the two resin components Palapreg P17-02 and Palapreg H 814-01 are homogenized with the Dispermat CV, with a 4 cm toothed disk, at 1200 rpm for one minute. 50 g of this mixture are then placed in a 175 ml PE beaker, and the respective additive is incorporated with stirring using the Dispermat CV (toothed disk d=2.5 cm at 1000 rpm). The amount selected in each case is that corresponding to 0.8 wt % of the urea compound. Following addition, stirring is continued for two minutes more.

(88) The samples are then introduced directly into 50 ml snap-on lid bottles, and left to stand at RT. After three days, the separation of the samples is assessed, in percent relative to the total amount introduced, and there is also visual evaluation of the gel strength, as a measure of the rheological activity. The lower the separation of the samples, the better the rheological activity of the samples. Besides the rheological activity, color influence by the additive on the formulation also plays a part, and must be as small as possible. At the same time, a high boiling point of the amide compound is relevant for application in the sheet molding compounds sector, since otherwise the ambient air will be polluted when the compounds are subjected to hot pressing, and gas bubbles which form cause unwanted air inclusions in the pressed compound.

(89) Resin Formulation (Parts by Weight):

(90) TABLE-US-00012 Palapreg P 17-02 70 Palapreg H 814-01 30
Results:

(91) TABLE-US-00013 Separation after Composition Gel three days at (each containing strength room temperature 38 wt % of urea) visual % Control 38 Comparative Ex. C11 5 37 Comparative Ex. C12 5 38 K1 1 0

(92) From the results it is apparent that the inventive composition in comparison to comparative examples C11 and C12 has a marked influence on the unwanted phase separation and, by increasing the gel strength, effectively and completely prevents separation.