Performance boosting UV-absorbing compounds
View Patent ↗UV-absorbing compounds are disclosed that are derived from at least: (a) a UV absorber having at least one hydroxyl group, primary amine group, or secondary amine group, (b) a coupling agent having anhydride functionality, and (c) a graft host comprising an unsaturated fatty acid. These compounds absorb, scatter, deflect, or scatter ultraviolet radiation in a variety of personal care and performance chemical applications. R″ and R′″ are alkyl or alkenyl groups that naturally occur in oil.
1. A method of preparing a UV-absorbing compound that comprises the steps: (a) selecting a UV absorber having at least one hydroxyl group, primary amine, or secondary amine group, and further comprising one or more of a ρ-aminobenzoic derivative, benzophenone derivative, benzotriazole derivative, benzimidazole derivative, camphor derivative, cinnamate, quinone, salicylate, or triazine derivative, (b) selecting a preformed ene graft reaction product formed from an ene graft reaction between an anhydride coupling agent and an unsaturated fatty acid, (c) creating a mixture comprising the components of steps (a) and (b), and (d) heating said mixture to a temperature from about 50° C. to about 250° C.
2. The method of claim 1 additionally comprises the steps of (a) selecting at least one initiator, reaction solvent, or catalyst, and (b) adding to said mixture.
3. A method of preparing a UV-absorbing compound that comprises the steps: (a) selecting a UV absorber having at least one hydroxyl group, primary amine, or secondary amine group, and further comprising one or more of a ρ-aminobenzoic derivative, benzophenone derivative, benzotriazole derivative, benzimidazole derivative, camphor derivative, cinnamate, quinone, salicylate, or triazine derivative, (b) selecting an anhydride coupling agent (c) selecting an unsaturated fatty acid, (d) creating a mixture comprising the components of steps (a) through (c), and (e) heating said mixtures to a temperature range from about 50° C. to about 250° C.
4. The method of claim 3 additionally comprising the steps of (a) selecting at least one initiator, reaction solvent, or catalyst, and (b) adding to said mixture.
5. The method of claim 1 wherein the UV absorber is selected from the group consisting of: aminobenzoic acid; 2-aminobenzophenone; amyl dimethyl PABA; bemotrizinol; benzophenone-3; benzophenone-4; benzophenone-9; 2-(2H-benzotriazole-2-yl)-4, 6-di-tert-pentylphenol; 2-(2H-benzotriazole-2-yl)-4-methylphenol; 2-(2H-benzotriazole-2-yl)-4,6-bis(1-methyl-1-phenylethyl)phenol; bis-benzoxazoyl phenyl ethylhexyl amino triazine; 3-benzylidene camphor sulfonic acid; N,N-bisformyl-N,N-bis-(2,2,6,6-tetramethyl-4-piperidinyl)-hexamethylendi-amine; bisoctrizole; 2-Rp-(tert-butylamido)-anilino]-4,6,-bis [(p-(2′-ethylhexyl-1′-oxycarbony-1)-anilinol-1,3,5-triazine; 6-tert-butyl-2-(5-chloro-2H-benzotriazole-2-yl)-4-methylphenol; 2,4-di-tert-butyl-6-(5-chloro-2H-benzotriazole-2-yl)-phenol; camphor benzalkonium methosulfate; diethanolamine p-methoxycinnamate; diethylaminohydroxybenzoylhexylbenzoate; diethylhexyl butamido triazone; digalloyl trioleate; dioxybenzone; disodium phenyl dibenzimidazole tetrasulfonate; drometrizole trisiloxane; ecamsule; ensulizole; ethyl 4-bis(hydroxypropyl)aminobenzoate; ethylhexyl p-methoxycinnamate; 2-ethylhexyl salicylate; ethylhexyl triazone; beta-2-glucopyranoxypropylhydroxybenzophenone; glyceryl aminobenzoate; homomethyl salicylate; [2-hydroxy-4-(octyloxy)phenyl](phenyl)methanone; 2-[bis (2-hydroxyethyl)amino] ethyl salicylate; (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid; lawsone with dihydroxyacetone; meradimate; methoxycinnamido propyl hydroxy sultaine menthyl anthranilate; meradimate; methyl-2-aminobenzoate; oxybenzone; 2-phenylbenzimidazole-5-sulfonic acid (and its potassium, sodium and triethanolamine salts); sulisobenzone; bis-(2,2,6,6-tetramethyl-4-piperidyl)-sebacate; sterically hindered oligomeric amine; triethanolamine salicylate; N-(2-ethoxyphenyl)-N-(2-ethylphenyl)oxamide; 4-methylhexyl 3-(3-benzotriazol-2-yl-4-hydroxy-5-tert-butyl-phenyl) propanoate; and combinations thereof.
6. The method of claim 1 wherein selecting a UV absorber further comprises selecting a first UV absorber and a second UV absorber, each of the first and second UV absorber having at least one hydroxyl group, primary amine, or secondary amine group.
7. The method of claim 6 wherein the one of the first and second UV absorber is a UV-A active and the other of the first and second UV absorber is a UV-B active.
8. The method of claim 1 further comprising hydrogenating the preformed ene graft reaction product.
9. The method of claim 3 wherein selecting a UV absorber further comprises selecting a first UV absorber and a second UV absorber, each of the first and second UV absorber having at least one hydroxyl group, primary amine, or secondary amine group.
10. The method of claim 3 wherein the UV absorber is selected from the group consisting of: aminobenzoic acid; 2-aminobenzophenone; amyl dimethyl PABA; bemotrizinol; benzophenone-3; benzophenone-4; benzophenone-9; 2-(2H-benzotriazole-2-yl)-4,6-di-tert-pentylphenol; 2-(2H-benzotriazole-2-yl)-4-methylphenol; 2-(2H-benzotriazole-2-yl)-4,6-bis (1-methyl-1-phenylethyl)phenol; bis-benzoxazoyl phenyl ethylhexyl amino triazine; 3-benzylidene camphor sulfonic acid; N,N-bisformyl-N,N-bis-(2,2,6,6-tetramethyl-4-piperidinyl)-hexamethylendi-amine; bisoctrizole; 2-Rp-(tert-butylamido)-anilino]-4,6,-bis [(p-(2′-ethylhexyl-1′-oxycarbony-1)-anilinol-1,3,5-triazine; 6-tert-butyl-2-(5-chloro-2H-benzotriazole-2-yl)-4-methylphenol; 2,4-di-tert-butyl-6-(5-chloro-2H-benzotriazole-2-yl)-phenol; camphor benzalkonium methosulfate; diethanolamine p-methoxycinnamate; diethylaminohydroxybenzoylhexylbenzoate; diethylhexyl butamido triazone; digalloyl trioleate; dioxybenzone; disodium phenyl dibenzimidazole tetrasulfonate; drometrizole trisiloxane; ecamsule; ensulizole; ethyl 4-bis(hydroxypropyl)aminobenzoate; ethylhexyl p-methoxycinnamate; 2-ethylhexyl salicylate; ethylhexyl triazone; beta-2-glucopyranoxypropylhydroxybenzophenone; glyceryl aminobenzoate; homomethyl salicylate; [2-hydroxy-4-(octyloxy)phenyl](phenyl)methanone; 2-[bis (2-hydroxyethyl)amino] ethyl salicylate; (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid; lawsone with dihydroxyacetone; meradimate; methoxycinnamido propyl hydroxy sultaine menthyl anthranilate; meradimate; methyl-2-aminobenzoate; oxybenzone; 2-phenylbenzimidazole-5-sulfonic acid (and its potassium, sodium and triethanolamine salts); sulisobenzone; bis-(2,2,6,6-tetramethyl-4-piperidyl)-sebacate; sterically hindered oligomeric amine; triethanolamine salicylate; N-(2-ethoxyphenyl)-N-(2-ethylphenyl)oxamide; 4-methylhexyl 3-(3-benzotriazol-2-yl-4-hydroxy-5-tert-butyl-phenyl) propanoate; and combinations thereof.