Material formed from dendritic molecules containing associative groups

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.

1 . 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 moreover, 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. 
     
     
         2 . Material according to  claim 1 , wherein a fraction of the dendritic molecules is insoluble. 
     
     
         3 . Material according to  claim 1 , wherein the soluble fraction of said dendritic molecules has a number-average molecular weight between 300 and 300 000 g/mol. 
     
     
         4 . Material according to  claim 1 , wherein furthermore said dendritic molecules each have C 6 -C 20  alkyl chains, preferably in greater number than said associative end groups. 
     
     
         5 . Material according to  claim 1 , which contains at least 25% by number of said dendritic molecules. 
     
     
         6 . Material according to  claim 5 , which contains at least 50% by number of said dendritic molecules. 
     
     
         7 . Material according to  claim 1 , wherein the associative groups are selected from the imidazolidonyl, triazolyl, triazinyl, bis-ureyl, and ureido-pyrimidyl groups. 
     
     
         8 . Material according to  claim 1 , which can be obtained according to the method comprising the following successive stages:
 (a) reaction of at least one compound that is at least trifunctional (A) bearing first and second functions with at least one compound (B) bearing, 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 associative group, preferably at a ratio by number of the reactive groups of compound (B) to the sum of the first functions of compound (A) in the range from 0.1 to 0.8 and preferably from 0.3 to 0.8;   (b) reaction of the compound or compounds obtained in stage (a) with at least one compound that is at least bifunctional (C) whose functions are capable of reacting with the second functions of compound (A) to form ester or thioester bridges, alone or in combination with amide or urea bridges.   
     
     
         9 . Material according to  claim 8 , wherein the method further includes stage (c) comprising addition of talc to the material obtained from stage (b), for example by dusting. 
     
     
         10 . Material according to  claim 8 , 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, alcohol and amine functions.   
     
     
         11 . Material according to  claim 8 , wherein compound (A) contains from 5 to 100, preferably from 12 to 100 and more preferably from 24 to 90 carbon atoms. 
     
     
         12 . Material according to  claim 8 , wherein compound (A) is a trimer of fatty acid of vegetable origin. 
     
     
         13 . Material according to  claim 12 , wherein compound (A) is a trimer of at least one of the following acids: undecylenic, myristoleic, palmitoleic, oleic, linoleic, linolenic, ricinoleic, eicosenoic, docosenoic, eicosapentaenoic and docosahexaenoic acid. 
     
     
         14 . Material according to  claim 8 , 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 or sulphur atom or a group —NH, preferably an oxygen atom. 
       
     
     
         15 . Material according to  claim 14 , wherein compound (B) is selected from: 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. 
     
     
         16 . Material according to  claim 8 , wherein compound (C) is a diepoxide. 
     
     
         17 . Material according to  claim 16 , wherein compound (C) is selected from:
 bisphenol A diglycidyl ether, bisphenol F diglycidyl ether, tetrabromo bisphenol A diglycidyl ether, or 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, neopentylglycol 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.   
     
     
         18 . Material according to  claim 8 , wherein compound (C) is, a diol. 
     
     
         19 . Material according to  claim 18 , wherein compound (C) is selected from:
 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.   
     
     
         20 . Method of preparation of a material according to  claim 1 , wherein it comprises the following successive stages:
 (a) reaction of at least one compound that is at least trifunctional (A) bearing first and second functions with at least one compound (B) bearing, 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 associative group, preferably at a ratio by number of the reactive groups of compound (B) to the sum of the first functions of compound (A) in the range from 0.1 to 0.8 and preferably from 0.3 to 0.8;   (b) reaction of the compound or compounds obtained in stage (a) with at least one compound that is at least bifunctional (C) whose functions are capable of reacting with the second functions of compound (A) to form ester or thioester bridges, alone or in combination with amide or urea bridges.   
     
     
         21 . Method for making seals, watch straps, thermal or acoustic insulation, tyres, rubber bands, cables, cladding, soles of footwear, packaging, coatings (paints, films, cosmetics, sealing coatings), patches (cosmetic or dermo-pharmaceutical) 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 adhesives, and O-ring or flat seals, notably by abutting the two ends of a straight tube, plate, cylinder or lamina, comprising mixing the material of  claim 1 , in single-phase or multi-phase mixtures, with one or more compounds such as petroleum fractions, solvents, mineral and organic fillers, plasticizers, tackifying resins, antioxidants, pigments and/or colorants. 
     
     
         22 . Cosmetic composition containing a material according to  claim 1  as well as optionally at least one oil and/or water and/or an alcohol. 
     
     
         23 . Cosmetic method for the care and/or make-up of the skin and/or of its appendages (such as the eyelashes and the nails) and/or of the lips, comprising the use of the composition according to  claim 22 . 
     
     
         24 . Cosmetic method for the washing, conditioning and/or dressing of the hair, comprising the use of the composition according to  claim 22 .