Material formed from dendritic molecules containing associative groups

Patent metadata

Field	Value
Publication number	US-9301912-B2
Application number	US-201514592461-A
Country	US
Kind code	B2
Filing date	Jan 8, 2015
Priority date	Dec 6, 2007
Publication date	Apr 5, 2016
Grant date	Apr 5, 2016

Abstract

The present invention relates to a material comprising dendritic molecules each constituted of fragments that are at least bifunctional and of fragments that are at least trifunctional joined together by ester or thioester bridges, alone or in combination with amide or urea bridges, said bridges being formed from two functions carried by different fragments, said molecules containing, on the fragments located at the ends of the dendritic branches, associative end groups capable of forming associations with one another by hydrogen bonds and joined covalently to the functions that are not involved in said bridges. It also relates to the method of production thereof, as well as to its uses and to compositions, notably cosmetic, containing this material.

First claim

The invention claimed is:

1. A material comprising talc and branched molecules whose backbone has at least two branchings, wherein each molecule is constituted of fragments that are at least bifunctional, obtained from compounds (C) containing at least two functions, identical or different, and of fragments that are at least trifunctional, obtained from compounds (A) containing at least three functions, identical or different, such that these fragments are joined together by ester bridges formed on each end of the bifunctional fragments, said bridges being formed by reacting one function from compound (C) with one function from compound (A), said molecules containing moreover, on the at least trifunctional fragments located at the ends of the branches, associative end groups capable of forming associations with one another by hydrogen bonds, wherein said associative end groups are connected to the trifunctional fragments via a direct bond or via a chain, wherein said associative end groups are obtained by reacting compounds (B) bearing each at least one of such associative end groups with functions of compound (A) that have not been involved in the formation of said ester bridges, wherein the associative end groups are selected from the imidazolidonyl, triazolyl, triazinyl, bis-ureyl, and ureido-pyrimidyl groups;
wherein the material contains at least 25% by number of said branched molecules, and
wherein said branched molecules each have C 6 -C 24 alkyl chains.

2. The material according to claim 1 , wherein a fraction of the branched molecules is insoluble and a fraction of the branched molecules is soluble.

3. The material according to claim 2 , wherein the soluble fraction of said branched molecules has a number-average molecular weight between 300 and 300 000 g/mol.

4. Material according to claim 1 , which is obtained according to the method comprising the following successive stages:
(a) reaction of at least one compound that is at least trifunctional (A) bearing each at least three reactive functions, which are identical or different, including a first function and a second function, which are identical or different, with compounds (B) bearing each, on the one hand, at least one reactive group capable of reacting with the first functions of (A) and, on the other hand, at least one of said associative end groups;
(b) reaction of the compound or compounds obtained in stage (a) with at least one compound that is at least bifunctional (C) containing functions, which are identical or different, and that are capable of reacting with the second functions of compound (A) to form ester bridges; and
(c) addition of talc to the material obtained from stage (b).

5. The material according to claim 4 , wherein:
compound (A) contains at least three functions, identical or different, selected from the acid, ester or acyl chloride functions,
compound (B) contains at least one reactive group selected from the primary or secondary amine or alcohol groups, and
compound (C) contains at least two functions, identical or different, selected from the epoxy functions and alcohol functions.

6. The material according to claim 4 , wherein compound (A) contains from 5 to 100 carbon atoms.

7. The material according to claim 4 , wherein compound (A) is a trimer of fatty acid of vegetable origin.

8. The material according to claim 4 , wherein compound (B) corresponds to formula (B1), (B2) or (B3):

where:
R denotes a unit containing at least one primary or secondary amine or alcohol group,
R′ denotes a hydrogen atom,
A denotes an oxygen.

9. The material according to claim 8 , wherein compound (B) is selected from the group consisting of 2-aminoethylimidazolidone (UDETA), 1-(2-[(2-aminoethyl)amino]ethyl)imidazolidone (UTETA), 1-(2-{2-[2-aminoethylamino]ethyl}amino)ethyl]imidazolidone (UTEPA), 3-amino-1,2,4-triazole and 4-amino-1,2,4-triazole.

10. The material according to claim 4 , wherein compound (C) is a diepoxide.

11. The material according to claim 10 , wherein compound (C) is selected from the group consisting of bisphenol A diglycidyl ether, bisphenol F diglycidyl ether, tetrabromo bisphenol A diglycidyl ether, hydroquinone diglycidyl ether, ethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, butylene glycol diglycidyl ether, neopentyl glycol diglycidyl ether, 1,4-butanediol diglycidyl ether, 1,6-hexanediol diglycidyl ether, cyclohexanedimethanol diglycidyl ether, polyethylene glycol diglycidyl ether, polypropylene glycol diglycidyl ether, polytetramethylene glycol diglycidyl ether, resorcinol diglycidyl ether, bisphenol A polyethylene glycol diglycidyl ether, bisphenol A polypropylene glycol diglycidyl ether, diglycidyl ester of terephthalic acid, polyunsaturated epoxidized fatty acids, and epoxidized limonene; and mixtures thereof.

12. The material according to claim 4 , wherein compound (C) is a diol.

13. The material according to claim 12 , wherein compound (C) is selected from the group consisting of ethylene glycol, propylene glycol, tetramethylene glycol, hexamethylene glycol, octanediol, nonanediol, decanediol, diethylene glycol, dipropylene glycol, triethylene glycol, tetraethylene glycol, polyethylene glycol, polypropylene glycol, polytetramethylene glycol, polyesters with hydroxy ends, polybutadienes with hydroxy ends, polydimethylsiloxanes with hydroxy ends, polyisobutylenes with hydroxy ends, polybutadiene-co-acrylonitrile copolymers with hydroxy ends, diol dimers obtained from fatty acids and mixtures thereof.

14. The material according to claim 4 , wherein the ratio by number of the reactive groups of compound (B) to the sum of the first functions of compound (A) is in the range from 0.1:1 to 0.8:1.

15. The material according to claim 14 , wherein the ratio by number of the reactive groups of compound (B) to the sum of the first functions of compound (A) is in the range from 0.3:1 to 0.8:1.

16. The material according to claim 4 , wherein compound (A) contains from 24 to 90 carbon atoms.

17. The material according to claim 1 , wherein compound (A) is a trimer of at least one of the acids selected from the group consisting of undecylenic, myristoleic, palmitoleic, oleic, linoleic, linolenic, ricinoleic, eicosenoic, docosenoic, eicosapentaenoic and docosahexaenoic acid.

18. A method of preparation of a material according to claim 1 comprising the following successive stages:
(a) reacting compounds that are at least trifunctional (A) bearing each at least three reactive functions, which are identical or different, including a first and a second group of functions, which are identical or different, with compounds (B) bearing each, on the one hand, at least one reactive group capable of reacting with the first group of functions of (A) and, on the other hand, at least one of said associative end groups;
(b) reacting a compound or compounds obtained in stage (a) with compounds that are at least bifunctional (C) containing functions, which are identical or different, and that are capable of reacting with the second group of functions of (A) to form ester bridges.

19. A method for making seals, watch straps, thermal or acoustic insulation, tyres, rubber bands, cables, cladding, soles of footwear, packaging, coatings patches or other systems for trapping and release of actives, wound dressings, flexible hose clips, vacuum tubes, pipes and hoses for conveying fluids, additives for hot-melt glues and

Assignees

• Arkema France
• Centre Nat Rech Scient

Inventors

• Tournilhac François-Genes
• Hidalgo Manuel
• Leibler Ludwik

Classifications

• C08G63/685

  containing nitrogen · CPC title

• C08G63/12

  derived from polycarboxylic acids and polyhydroxy compounds · CPC title

• A61Q5/06

  Preparations for styling the hair, e.g. by temporary shaping or colouring · CPC title

• C07D253/02

  not condensed with other rings · CPC title

• C07D251/02

  not condensed with other rings · CPC title