The present invention relates to a method to synthesize with high yield a colored metal complex of β-diketones and/or polyphenols by mechanochemistry without using aqueous or organic solvents and covers new complexes obtained therefrom. In an embodiment, only the reactants, a metal alkoxide and a β-diketone and/or a polyphenol, are present and react at different molar ratios to form a metal complex in the form of a homogeneous colored material (i.e. powder) with high yield. If curcumin is used, the color of the final metal complex dye depends on several factors such as the curcuminoids, the metal, the type of alkoxide used, the stoichiometric molar ratio of both reactants and the additives used. If titanium alkoxide and any additive is used, a red or violet colored titanium curcumin complex in powder form is produced. The production process of the metal complex in powder form is characterized by facility of scale up. The entire product is ready to be used in several applications. If polyphenols such as ferulic acid, quercetin, ellagic acid or lignin are used instead of curcumin, other colored complexes are obtained using mechanochemistry. In addition, the product comprising metal complexes of β-diketones and/or polyphenols is characterized by green chemistry manufacture. Besides, these metal complexes of β-diketones and/or polyphenols in several formulations are characterized by improved stability under storage conditions and improved sun protection against UV rays for human skin and human hair. The product is ready to be used alone or in combination with other additives or active ingredients in different formulations. The invention also covers the use of these metal β-diketones/polyphenol complexes in food, cosmetics, the pharmaceutical field and in the creativity field, as sunscreen, skin and hair concealer or foundation in powder form or cream, keratinous dye, textile dye, food dye, dye emulsions, miniemulsions, polymer colloids and catalysts.

The production process of these novel metal-complex dyes is also characterized by rapid production of colored compounds without using solvents and, thus, ecofriendliness. The process of the production of metal β-diketone and/or polyphenol complexes is characterized by the non-formation of toxic by-products and high yield.

In addition, the present invention comprises a hair dyeing molecule or formulation and procedure combining excellent dyeing properties with reduced risk of development cancer or allergies, while being ecological and of the natural origin.

The present invention relates to a method to synthesize with high yield a colored metal complex of β-diketones and/or polyphenols by mechanochemistry without using aqueous or organic solvents and covers new complexes obtained therefrom. In an embodiment, only the reactants, a metal alkoxide and a β-diketone and/or a polyphenol, are present and react at different molar ratios to form a metal complex in the form of a homogeneous colored material (i.e. powder) with high yield. If curcumin is used, the color of the final metal complex dye depends on several factors such as the curcuminoids, the metal, the type of alkoxide used, the stoichiometric molar ratio of both reactants and the additives used. If titanium alkoxide and any additive is used, a red or violet colored titanium curcumin complex in powder form is produced. The production process of the metal complex in powder form is characterized by facility of scale up. The entire product is ready to be used in several applications. If polyphenols such as ferulic acid, quercetin, ellagic acid or lignin are used instead of curcumin, other colored complexes are obtained using mechanochemistry. In addition, the product comprising metal complexes of β-diketones and/or polyphenols is characterized by green chemistry manufacture. Besides, these metal complexes of β-diketones and/or polyphenols in several formulations are characterized by improved stability under storage conditions and improved sun protection against UV rays for human skin and human hair. The product is ready to be used alone or in combination with other additives or active ingredients in different formulations. The invention also covers the use of these metal β-diketones/polyphenol complexes in food, cosmetics, the pharmaceutical field and in the creativity field, as sunscreen, skin and hair concealer or foundation in powder form or cream, keratinous dye, textile dye, food dye, dye emulsions, miniemulsions, polymer colloids and catalysts.

The production process of these novel metal-complex dyes is also characterized by rapid production of colored compounds without using solvents and, thus, ecofriendliness. The process of the production of metal β-diketone and/or polyphenol complexes is characterized by the non-formation of toxic by-products and high yield.

In addition, the present invention comprises a hair dyeing molecule or formulation and procedure combining excellent dyeing properties with reduced risk of development cancer or allergies, while being ecological and of the natural origin.

The present invention relates to a method to synthesize with high yield a colored metal complex of β-diketones and/or polyphenols by mechanochemistry without using aqueous or organic solvents and covers new complexes obtained therefrom. In an embodiment, only the reactants, a metal alkoxide and a β-diketone and/or a polyphenol, are present and react at different molar ratios to form a metal complex in the form of a homogeneous colored material (i.e. powder) with high yield. If curcumin is used, the color of the final metal complex dye depends on several factors such as the curcuminoids, the metal, the type of alkoxide used, the stoichiometric molar ratio of both reactants and the additives used. If titanium alkoxide and any additive is used, a red or violet colored titanium curcumin complex in powder form is produced. The production process of the metal complex in powder form is characterized by facility of scale up. The entire product is ready to be used in several applications. If polyphenols such as ferulic acid, quercetin, ellagic acid or lignin are used instead of curcumin, other colored complexes are obtained using mechanochemistry. In addition, the product comprising metal complexes of β-diketones and/or polyphenols is characterized by green chemistry manufacture. Besides, these metal complexes of β-diketones and/or polyphenols in several formulations are characterized by improved stability under storage conditions and improved sun protection against UV rays for human skin and human hair. The product is ready to be used alone or in combination with other additives or active ingredients in different formulations. The invention also covers the use of these metal β-diketones/polyphenol complexes in food, cosmetics, the pharmaceutical field and in the creativity field, as sunscreen, skin and hair concealer or foundation in powder form or cream, keratinous dye, textile dye, food dye, dye emulsions, miniemulsions, polymer colloids and catalysts.

The production process of these novel metal-complex dyes is also characterized by rapid production of colored compounds without using solvents and, thus, ecofriendliness. The process of the production of metal β-diketone and/or polyphenol complexes is characterized by the non-formation of toxic by-products and high yield.

In addition, the present invention comprises a hair dyeing molecule or formulation and procedure combining excellent dyeing properties with reduced risk of development cancer or allergies, while being ecological and of the natural origin.

An object is to provide a method for producing a ketene derivative that decreases the consumption quantity of phosphorus compounds, and the discharge quantity of the phosphorus compounds into the environment.

A method for producing a ketene derivative includes a step (i) of conducting thermal decomposition reaction of acetic acid in a presence of a phosphorus-containing catalyst in a reactor to produce a thermal decomposition gas containing ketene, a step (ii) of cooling the thermal decomposition gas to be separated into a gaseous component containing ketene, and a condensed liquid containing a phosphorus compound (a), and a step (iii) of causing the ketene to react with a different organic compound to produce a ketene derivative. The step (i) includes conducting the thermal decomposition reaction while supplying, into the reactor, the condensed liquid containing the phosphorus compound (a) or a concentrated liquid of the condensed liquid.

Methods are provided for synthesizing W(IV) beta-diketonate precursors. Additionally, methods are provided for forming W containing thin films, such as WS.sub.2, WN.sub.x, WO.sub.3, and W via vapor deposition processes, such as atomic layer deposition (ALD) type processes and chemical vapor deposition (CVD) type processes. Methods are also provided for forming 2D materials containing W.

Methods are provided for synthesizing W(IV) beta-diketonate precursors. Additionally, methods are provided for forming W containing thin films, such as WS.sub.2, WN.sub.x, WO.sub.3, and W via vapor deposition processes, such as atomic layer deposition (ALD) type processes and chemical vapor deposition (CVD) type processes. Methods are also provided for forming 2D materials containing W.

Methods are provided for synthesizing W(IV) beta-diketonate precursors. Additionally, methods are provided for forming W containing thin films, such as WS.sub.2, WN.sub.x, WO.sub.3, and W via vapor deposition processes, such as atomic layer deposition (ALD) type processes and chemical vapor deposition (CVD) type processes. Methods are also provided for forming 2D materials containing W.

A phosphine oxide compound represented by the following formula (I) and a rare earth complex containing the same are disclosed:

##STR00001## wherein n represents an integer of 3 or more, Ar.sup.1 represents an n-valent aromatic group, L represents a divalent linker group, and Ar.sup.2 and Ar.sup.3 each independently represent a monovalent aromatic groups.

To provide europium complexes having high photostability. A europium complex expressed with the following formula (A): ##STR00001##
{wherein, R.sup.A and R.sup.B are independently a cyclic alkyl group with 3 to 10 carbons, respectively, and R.sup.C is a cyclic alkyl group with 3 to 10 carbons or a phenyl group expressed with the following formula (B): ##STR00002##
(wherein, X.sup.A, X.sup.B, A.sup.C, X.sup.D and X.sup.E independently represent a hydrogen atom; a fluorine atom; an alkyl group with 1 to 3 carbon(s); an alkyloxy group with 1 to 3 carbon(s); an aryloxy group with 6 to 10 carbons; a fluoroalkyl group with 1 to 3 carbon(s); a fluoroalkyloxy group with 1 to 3 carbon(s); or a phenyl group that may be substituted with a fluorine atom, an alkyl group with 1 to 3 carbon(s), an alkyloxy group with 1 to 3 carbon(s), a fluoroalkyl group with 1 to 3 carbon(s), a fluoroalkyloxy group with 1 to 3 carbon(s), a fluorophenyl group, a hydroxyl group or a cyano group, respectively); R.sup.A is a cyclic alkyl group with 3 to 10 carbons; R.sup.B and R.sup.C are a phenyl group expressed with the formula (B), provided, however, that a case where R.sup.A a cyclohexyl group, and, R.sup.B and R.sup.C are a phenyl group is excluded; or R.sup.A, R.sup.B and R.sup.C independently represent an ortho-substituted phenyl group expressed with the following formula (Ba): ##STR00003##
(wherein, X.sup.E represents a hydrogen atom, an alkyl group with 1 to 3 carbon(s), an alkyloxy group with 1 to 3 carbon(s), a fluoroalkyl group with 1 to 3 carbon(s), a fluoroalkyloxy group with 1 to 3 carbon(s), a naphthyl group that may be substituted with a fluorine atom, a pyridyl group that may be substituted with a fluorine atom, or a phenyl group that is expressed with a formula (C): ##STR00004##
[wherein, Z.sup.A, Z.sup.C and Z.sup.E independently represent a hydrogen atom, a fluorine atom, an alkyl group with 1 to 3 carbon(s), an alkyloxy group with 1 to 3 carbon(s), a fluoroalkyl group with 1 to 3 carbon(s), a fluoroalkyloxy group with 1 to 3 carbon(s), a phenyl group that may be substituted with a fluorine atom, a hydroxyl group or a cyano group; Z.sup.B and Z.sup.D independently represent a hydrogen atom or a fluorine atom, respectively], provided, however, that a case where R.sup.A, R.sup.B and R.sup.C are all a phenyl group is excluded), respectively; R.sup.D represents a hydrogen atom, a deuterium atom or a fluorine atom; W.sup.A and W.sup.B independently represent an alkyl group with 1 to 6 carbon(s), a fluoroalkyl group with 1 to 6 carbon(s), a phenyl group, a 2-thienyl group or a 3-thienyl group; and ‘n’ represents an integer of 1 to 3}.

A method for converting an N,N-dialkylamide compound into an ester compound includes using a fourth period transition metal complex as a catalyst. The fourth period transition metal complex is obtained by a reaction of a precursor having a fourth period transition metal with a nitrogen-containing compound or a phosphorus-containing compound.