WO2022128452A1 - Polymère se présentant sous la forme d'un solide pulvérulent et présentant des propriétés épaississantes de milieux polaires - Google Patents
Polymère se présentant sous la forme d'un solide pulvérulent et présentant des propriétés épaississantes de milieux polaires Download PDFInfo
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- WO2022128452A1 WO2022128452A1 PCT/EP2021/083620 EP2021083620W WO2022128452A1 WO 2022128452 A1 WO2022128452 A1 WO 2022128452A1 EP 2021083620 W EP2021083620 W EP 2021083620W WO 2022128452 A1 WO2022128452 A1 WO 2022128452A1
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- 229920000642 polymer Polymers 0.000 title claims abstract description 85
- 239000007787 solid Substances 0.000 title claims abstract description 12
- 230000008719 thickening Effects 0.000 title description 10
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims abstract description 31
- 235000013922 glutamic acid Nutrition 0.000 claims abstract description 31
- 239000004220 glutamic acid Substances 0.000 claims abstract description 31
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 24
- OZDAOHVKBFBBMZ-UHFFFAOYSA-N 2-aminopentanedioic acid;hydrate Chemical compound O.OC(=O)C(N)CCC(O)=O OZDAOHVKBFBBMZ-UHFFFAOYSA-N 0.000 claims abstract description 13
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims abstract description 8
- -1 hydroxyoctadecyl Chemical group 0.000 claims description 79
- 239000000203 mixture Substances 0.000 claims description 62
- 150000001875 compounds Chemical class 0.000 claims description 45
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 35
- 229920002643 polyglutamic acid Polymers 0.000 claims description 33
- 108010020346 Polyglutamic Acid Proteins 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 17
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 15
- 239000002537 cosmetic Substances 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 239000002798 polar solvent Substances 0.000 claims description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 8
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 8
- 239000007864 aqueous solution Substances 0.000 claims description 7
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
- 229920006395 saturated elastomer Polymers 0.000 claims description 7
- AOBIOSPNXBMOAT-UHFFFAOYSA-N 2-[2-(oxiran-2-ylmethoxy)ethoxymethyl]oxirane Chemical compound C1OC1COCCOCC1CO1 AOBIOSPNXBMOAT-UHFFFAOYSA-N 0.000 claims description 6
- 239000004215 Carbon black (E152) Substances 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 6
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims description 6
- 229930195733 hydrocarbon Natural products 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 6
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 5
- 125000001204 arachidyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 230000000699 topical effect Effects 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 4
- 125000005644 linolenyl group Chemical group 0.000 claims description 4
- 125000005645 linoleyl group Chemical group 0.000 claims description 4
- 125000002960 margaryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 claims description 4
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 4
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000005065 undecenyl group Chemical group C(=CCCCCCCCCC)* 0.000 claims description 4
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 4
- SHKUUQIDMUMQQK-UHFFFAOYSA-N 2-[4-(oxiran-2-ylmethoxy)butoxymethyl]oxirane Chemical compound C1OC1COCCCCOCC1CO1 SHKUUQIDMUMQQK-UHFFFAOYSA-N 0.000 claims description 3
- 238000000889 atomisation Methods 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 3
- VDFVNEFVBPFDSB-UHFFFAOYSA-N 1,3-dioxane Chemical compound C1COCOC1 VDFVNEFVBPFDSB-UHFFFAOYSA-N 0.000 claims description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- HDPLHDGYGLENEI-UHFFFAOYSA-N 2-[1-(oxiran-2-ylmethoxy)propan-2-yloxymethyl]oxirane Chemical compound C1OC1COC(C)COCC1CO1 HDPLHDGYGLENEI-UHFFFAOYSA-N 0.000 claims description 2
- VLKXLWGYPOUERV-UHFFFAOYSA-N 2-[3-(oxiran-2-ylmethoxy)propoxymethyl]oxirane Chemical compound C1OC1COCCCOCC1CO1 VLKXLWGYPOUERV-UHFFFAOYSA-N 0.000 claims description 2
- JROOCDXTPKCUIO-UHFFFAOYSA-N 2-[4-(oxiran-2-ylmethoxy)butan-2-yloxymethyl]oxirane Chemical compound C1OC1COC(C)CCOCC1CO1 JROOCDXTPKCUIO-UHFFFAOYSA-N 0.000 claims description 2
- WTYYGFLRBWMFRY-UHFFFAOYSA-N 2-[6-(oxiran-2-ylmethoxy)hexoxymethyl]oxirane Chemical compound C1OC1COCCCCCCOCC1CO1 WTYYGFLRBWMFRY-UHFFFAOYSA-N 0.000 claims description 2
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims description 2
- PHKGGXPMPXXISP-DFWYDOINSA-N azanium;(4s)-4-amino-5-hydroxy-5-oxopentanoate Chemical compound [NH4+].[O-]C(=O)[C@@H]([NH3+])CCC([O-])=O PHKGGXPMPXXISP-DFWYDOINSA-N 0.000 claims description 2
- 235000013921 calcium diglutamate Nutrition 0.000 claims description 2
- UMVAYAXXQSFULN-QHTZZOMLSA-L calcium;(2s)-2-aminopentanedioate;hydron Chemical compound [Ca+2].[O-]C(=O)[C@@H](N)CCC(O)=O.[O-]C(=O)[C@@H](N)CCC(O)=O UMVAYAXXQSFULN-QHTZZOMLSA-L 0.000 claims description 2
- WDRWZVWLVBXVOI-QTNFYWBSSA-L dipotassium;(2s)-2-aminopentanedioate Chemical compound [K+].[K+].[O-]C(=O)[C@@H](N)CCC([O-])=O WDRWZVWLVBXVOI-QTNFYWBSSA-L 0.000 claims description 2
- PXEDJBXQKAGXNJ-QTNFYWBSSA-L disodium L-glutamate Chemical compound [Na+].[Na+].[O-]C(=O)[C@@H](N)CCC([O-])=O PXEDJBXQKAGXNJ-QTNFYWBSSA-L 0.000 claims description 2
- 235000013918 magnesium diglutamate Nutrition 0.000 claims description 2
- 229940063886 magnesium glutamate Drugs 0.000 claims description 2
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- WUIQPLSONDMSBW-UHFFFAOYSA-N 2-[1-(oxiran-2-ylmethoxy)butan-2-yloxymethyl]oxirane Chemical compound C1OC1COC(CC)COCC1CO1 WUIQPLSONDMSBW-UHFFFAOYSA-N 0.000 claims 1
- MYUGVHJLXONYNC-QHTZZOMLSA-J magnesium;(2s)-2-aminopentanedioate Chemical compound [Mg+2].[O-]C(=O)[C@@H](N)CCC([O-])=O.[O-]C(=O)[C@@H](N)CCC([O-])=O MYUGVHJLXONYNC-QHTZZOMLSA-J 0.000 claims 1
- 239000000178 monomer Chemical group 0.000 abstract description 6
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/40—Polyamides containing oxygen in the form of ether groups
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
- A61K8/88—Polyamides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/08—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from amino-carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/08—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from amino-carboxylic acids
- C08G69/10—Alpha-amino-carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/48—Polymers modified by chemical after-treatment
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/12—Powdering or granulating
- C08J3/122—Pulverisation by spraying
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/20—Compounding polymers with additives, e.g. colouring
- C08J3/203—Solid polymers with solid and/or liquid additives
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/24—Crosslinking, e.g. vulcanising, of macromolecules
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
- C08L77/04—Polyamides derived from alpha-amino carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2377/00—Characterised by the use of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Derivatives of such polymers
- C08J2377/04—Polyamides derived from alpha-amino carboxylic acids
Definitions
- the present invention relates to a polymer (P) in the form of a pulverulent solid, the process for preparing said polymer and a cosmetic composition comprising the polymer.
- Cosmetic compositions contain polar phases, such as for example phases consisting of water, and in most cases require the use of rheology modifying agents to increase the viscosity of these polar phases as well as to confer a rheological behavior well defined.
- rheology-modifying polymers of polar phases we can cite natural polymers, such as, for example, polysaccharides based on oses or derivatives of oses, or else synthetic polymers of the polyelectrolyte, anionic, cationic or amphiphilic type, linear or branched, reticulated or not.
- synthetic polymers Predominantly present on the market for ingredients intended for cosmetic formulations, synthetic polymers have the property of being deployed in the polar phase under the effect of electrostatic repulsions due to the presence of negative and/or positive charges on the polymer backbone.
- rheology modifiers provide both an increase in the viscosity of the polar phase as well as a certain consistency and/or a stabilizing effect conferred on the cosmetic, dermo-cosmetic or dermo-pharmaceutical formulation to be thickened.
- Agents conferring particular sensory properties softness to the touch, ease of gripping and application, freshness effect, etc.
- Agents that also have a direct impact on the appearance of the formula transparent, translucent or opaque.
- the rheology-modifying polymers of polar phases, and more particularly of aqueous phases are mainly polyelectrolytes which result from the radical polymerization of monomers of the (meth)acrylic type, that is to say acrylic or methacrylic acid, esters derived from acrylic or methacrylic acid or alternatively acrylamide or methacrylamide derivatives.
- Glutamic acid As an example of a polymer of natural origin, we can cite polyglutamic acid (PGA), which is today the subject of numerous research works. It is a predominantly linear polymer and consists of monomeric glutamic acid (GA) units. Glutamic acid is an amino acid characterized by an amine function in position a and by two carboxylic acid functions (or carboxylates depending on the pH) in positions a and y (cf. chemical formula n°l).
- the cross-linking of polymer chains aims to connect several polymer chains to each other which, when added to a polar phase, and more particularly to water, are in the form of an insoluble but swellable three-dimensional network in the atmosphere. water then leading to the production of an aqueous gel.
- the preparation of crosslinked polymers can be carried out in 1 or 2 steps according to the following two routes:
- - Way 2 In at least two stages, the first of which consists in preparing the polymer, and the second consists in reacting the polymer with a crosslinking agent to obtain a crosslinked polymer.
- the polyepoxide derivatives are the most described, because they make it possible to implement crosslinking processes under conditions that respect the environment (moderate temperatures, reactions in aqueous and absence of harmful solvents).
- a solution of the present invention is a polymer (P) in the form of a pulverulent solid comprising monomeric units derived from partially or totally salified glutamic acid (GA), and monomeric units of at least one crosslinking agent (AR) bearing at least two glycidyl functions.
- powdery solid is meant in the sense of the invention a solid consisting of fine particles little or not linked together.
- the monomeric units derived from partially or totally salified glutamic acid (GA) are bonded together either:
- the PGA can be prepared chemically according to peptide synthesis methods known to those skilled in the art, in particular passing through stages of selective protection(s), activation, coupling and deprotection(s).
- the coupling generally consists of a nucleophilic attack of the amine function of a monomeric glutamic acid unit on an activated carboxylic acid function of another monomeric glutamic acid unit.
- PGGA can also be obtained by processes comprising at least one microbial fermentation step involving the use of at least one bacterial strain.
- the term “salified” indicates that the “pendant” carboxylic acid function present on each monomeric glutamic acid (GA) unit of the polymer (in position y in the case of PAGA or a in the case of PGGA) is in the anionic or carboxylate form.
- the counter-ion of this carboxylate function is a cation derived, for example, from salts of alkali metals such as sodium, potassium or from salts of nitrogenous bases such as amines, lysine or monoethanolamine (HO-CH2-CH2 -NH2).
- crosslinking agent RA
- crosslinking agent (RA) carrying at least two glycidyl functions is meant within the meaning of the present invention a crosslinking agent (RA) as defined above whose molecular structure comprises at least two glycidyl units or functions of formula ( !'): [Chem 3]
- the cross-linking of the polymer chains of the polymer (P) takes place according to a reaction between the terminal free amine function (-NH2) and/or one or more "pendent" or terminal carboxylic (-COOH) or carboxylate (-COO) functions present in the structure of said polymer (P), and at least one epoxy group present in the structure of the crosslinking agent (AR) carrying at least two glycidyl functions.
- the crosslinking agent (RA) may be chosen from the members of the group consisting of:
- R3 representing a hydrogen atom or the glycidyl radical [ and x, y, z, o, p and q, independent of each other, representing an integer greater than or equal to 2 and less than or equal to 10.
- polymer (P) according to the invention may have one or more of the characteristics below:
- the polymer (P) is PGGA in acid or partially or totally salified form
- the crosslinking agent (RA) represents from 0.5% to 10% by mass
- the polymer (P) further comprises a compound of formula (XIV): [Chem 28] With R4 representing a linear or branched, saturated or unsaturated hydrocarbon radical, optionally comprising at least one hydroxyl function and comprising from 6 to 22 carbon atoms,
- R4 representing a hydrocarbon radical chosen from the elements of the group consisting of the radical heptyl, octyl, nonyl, decyl, undecyl, undecenyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, hydroxyoctadecyl, oleyl, linoleyl, linolenyl, eicosyl and dodecosyl,
- the compound of formula (XIV) represents from 1% to 50% by mass.
- PGGA can exist in different conformational forms in solution in water. These depend on the inter and intra molecular hydrogen bonds and therefore on the pH, the polymer concentration, the ionic strength of the solution, as well as the temperature.
- the PGGA chains can thus adopt the form of an a-helix, a P-sheet, aggregates or else be in a disordered and random state.
- the polymer (P) is in helical conformation when it is present in a solution at a mass content less than or equal to 0.1% and of which said aqueous solution shows a pH value less than or equal to 7 .
- the polymer (P) is in sheet conformation when it is present in an aqueous solution at a mass content less than or equal to 0.1% and of which said aqueous solution shows a pH value greater than 7.
- the crosslinking agent (RA) represents from 0.5% to 8% by mass, and even more particularly from 0.5% to 5% by weight.
- R4 representing a hydrocarbon radical is chosen from the elements of the group consisting of the n-octyl, n-nonyl, n-decyl, n-undecyl, n-undecenyl, n-dodecyl, n-tetradecyl, n-hexadecyl, n-octadecyl, 12-hydroxy octadecyl, n-eicosyl and n-dodecosyl.
- the present invention also relates to a method for preparing a polymer (P) as defined above, comprising the following 3 steps: a) A step for preparing a polar phase (PP) comprising partially or totally salified PGA , at least one polar solvent (SP) and at least one crosslinking agent (AR) comprising at least two glycidyl functions, b) A step of adjusting the pH of the aqueous solution obtained in step a) to a pH between 3 and 11, and c) A step of drying by atomization of the polar phase (PP) resulting from step b) so as to obtain the polymer (P).
- a a preparing a polar phase (PP) comprising partially or totally salified PGA , at least one polar solvent (SP) and at least one crosslinking agent (AR) comprising at least two glycidyl functions
- SP polar solvent
- AR crosslinking agent
- the method according to the invention may have one or more of the following characteristics:
- the polyglutamic acid involved is PGGA,
- All of the monomeric units constituting the PGA are derived from sodium glutamate, potassium glutamate, ammonium glutamate, calcium glutamate, magnesium glutamate or a mixture of these forms,
- the polar phase (PP) comprises for 100% of its mass: from 5% to 80% by mass of polyglutamic acid (PGA), from 0.025% to 8% by mass of the crosslinking agent (RA), from 12% at 94.975% by mass of at least one polar solvent,
- the polar solvent is chosen from the following list: water, methanol, ethanol, 1-propanol, 2-propanol, isobutanol, tert-butanol, 2-methyl-2-propanol, 1-butanol, 2-butanol, acetone, dimethyl ketone, diethyl ketone, tetrahydropyran, tetrahydrofiirane, 2- methyltetrahydrofuran, 1,3-dioxane and 1,4-dioxane,
- the polar phase (PP) further comprises at least one compound of formula (XIV): [Chem 29]
- R4 representing a linear or branched, saturated or unsaturated hydrocarbon radical, optionally comprising at least one hydroxyl function and comprising from 6 to 22 carbon atoms,
- R4 representing a hydrocarbon radical chosen from the elements of the group consisting of the radical heptyl, octyl, nonyl, decyl, undecyl, undecenyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, hydroxyoctadecyl, oleyl, linoleyl, linolenyl, eicosyl and dodecosyl,
- the content of compound of formula (XIV) in the polar phase (PP) is comprised, for 100% by mass of said polar phase (PP), between 0.05% and 35% by mass, it being understood that the sum of the proportions by mass of the polyglutamic acid (PGA), the crosslinking agent (RA), the polar solvent (SP) and the compound of formula (XIV) is equal to 100%.
- PGA poly
- the pH is between 4 and 10, preferably between 5 and 7,
- the drying is carried out using an atomizer implementing an air flow and a nozzle,
- the inlet temperature of the air flow is between 80 and 180°C, preferably between 100 and 170° vs.
- the polar phase (PP) comprises for 100% of its mass: from 5% to 70% by mass of the polyglutamic acid (PGA) of the polymer (P), from 0.025% to 7% by mass of the crosslinking agent (RA), from 23% to 94.975% by weight of at least one polar solvent (SP).
- PGA polyglutamic acid
- RA crosslinking agent
- SP polar solvent
- the polar phase (PP) comprises for 100% of its mass: from 5% to 60% by mass of polyglutamic acid (PGA) of the polymer (P), from 0.025% to 6% by mass of the crosslinking agent (RA), from 34% to 94.975% by weight of at least one polar solvent (SP).
- PGA polyglutamic acid
- RA crosslinking agent
- SP polar solvent
- the polar solvent is chosen from the following list: water, ethanol, acetone, dimethyl ketone.
- the polar solvent (SP) is water.
- R4 representing a hydrocarbon radical is chosen from the elements of the group consisting of the n-octyl, n-nonyl, n-decyl, n-undecyl, n-undecenyl, n-dodecyl, n-tetradecyl, n-hexadecyl, n-octadecyl, 12-hydroxy octadecyl, n-eicosyl and n-dodecosyl.
- the content of compound of formula (XIV) in the polar phase (PP) is comprised, for 100% by mass of said polar phase (PP), between 0.05% and 20% by mass, and even more particularly between 0.05% and 15% by mass, it being understood that the sum of the proportions by mass of the polyglutamic acid (PGA), of the crosslinking agent (RA), of the polar solvent (SP) and of the compound of formula ( XIV) is equal to 100%.
- the present invention also relates to a cosmetic composition for topical use (F) comprising, for 100% of its total mass, between 0.05% by mass and 10% by mass, more particularly between 0.1% by mass and 5% by mass, even more particularly between 0.1% by mass and 3% by mass of at least one polymer (P) as defined previously.
- a cosmetic composition for topical use comprising, for 100% of its total mass, between 0.05% by mass and 10% by mass, more particularly between 0.1% by mass and 5% by mass, even more particularly between 0.1% by mass and 3% by mass of at least one polymer (P) as defined previously.
- topical used in the definition of said composition (F) means that it is implemented by application to the skin, the hair, the scalp or the mucous membranes, whether it is a direct application in the case of a cosmetic or dermocosmetic preparation, or indirect application, for example in the case of a body care product in the form of a textile or paper wipe or sanitary products intended to be in contact with skin or mucous membranes.
- Said composition (F) is generally in the form of an aqueous or hydro-alcoholic or hydro-glycolic solution, in the form of a suspension, an emulsion, a microemulsion or a nano-emulsion, which they are of the water-in-oil, oil-in-water, water-in-oil-in-water or oil-in-water-in-oil type.
- Said composition (F) as defined previously can be packaged in a bottle, in a device of the pump “bottle” type, in pressurized form in an aerosol device, in a device provided with an openwork wall such as a grid or in a device provided with a ball applicator (known as a "roll-on").
- said composition (F) also comprises excipients and/or active principles usually used in the field of formulations for topical use, in particular cosmetic or dermocosmetic, such as thickening and/or gelling surfactants, stabilizers, film-forming compounds, hydrotropic agents, plasticizers, emulsifying and co-emulsifying agents, opacifying agents, pearlescent agents, superfatting agents, sequestering agents, chelating agents, antioxidants, perfumes, preservatives, conditioning agents , bleaching agents intended for the bleaching of hair and skin, active ingredients intended to provide a treatment action vis-à-vis the skin or hair, sunscreens, mineral fillers or pigments, particles providing a visual effect or intended for the encapsulation of active ingredients, exfoliating particles, texture agents.
- cosmetic or dermocosmetic such as thickening and/or gelling surfactants, stabilizers, film-forming compounds, hydrotropic agents, plasticizers, emulsifying and co-emulsifying agents, opacifying agents, pearl
- foaming surfactants and/or detergents which can be combined with the polymer (P) in said composition (F) as defined previously, mention may be made of foaming surfactants and/or anionic, cationic, amphoteric or nonionic detergents.
- anionic foaming and/or detergent surfactants which can be combined with the polymer (P) in the said composition (F) as defined previously, mention may be made of the salts of alkali metals, alkaline-earth metals, ammonium, d amines, or amino alcohols of alkyl ether sulphates, alkyl sulphates, alkylamidoether sulphates, alkylaryl polyether sulphates, monoglyceride sulphates, alpha-olefin sulphonates, paraffin sulphonates, alkyl phosphates, alkyl ether phosphates, alkyl sulfonates, alkylamide sulfonates, alkylaryl sulfonates, alkyl carboxylates, alkyl sulfosuccinates, alkyl ether sulfosuccinates, alkylamide sulfosuccinates, alkyl sulfoa
- foaming and/or detergent amphoteric surfactants which can be combined with the polymer (P) in the said composition (F) as defined previously, mention may be made of alkylbetaines, alkylamidobetaines, sultaines, alkylamidoalkylsulfobetaines, derivatives of imidazolines, phosphobetaines, amphopolyacetates and amphopropionates.
- foaming and/or detergent cationic surfactants which can be combined with the polymer (P) in the said composition (F) as defined previously, mention may be made in particular of the quaternary ammonium derivatives.
- nonionic foaming and/or detergent surfactants which can be combined with the polymer (P) in the said composition (F) as defined above, mention may be made more particularly of the alkylpolyglycosides comprising an aliphatic, linear or branched, saturated or unsaturated, and comprising from 8 to 16 carbon atoms, such as F octyl polyglucoside, decyl polyglucoside, undecylenyl polyglucoside, dodecyl polyglucoside, tetradecyl polyglucoside, hexadecyl polyglucoside, 1-12 dodecanediyl polyglucoside; ethoxylated hydrogenated castor oil derivatives such as the product marketed under the INCI name "Peg-40 hydrogenated castor oil”; polysorbates such as Polysorbate 20, Polysorbate 40, Polysorbate 60, Polysorbate 70, Polysorbate 80, Polysorbate 85; copra amides; N-alkylamines, N
- thickening and/or gelling surfactants which can be combined with the polymer (P) in the said composition (F) as defined above
- fatty esters of optionally alkoxylated alkylpolyglycosides such as ethoxylated methylpolyglucoside esters such as that PEG 120 methyl glucose trioleate and PEG 120 methyl glucose dioleate marketed respectively under the names GLUCAMATETM LT and GLUMATETM DOE120
- alkoxylated fatty esters such as PEG 150 pentaerythrytyl tetrastearate sold under the name CROTHIXTM DS53, PEG 55 propylene glycol oleate sold under the name ANTILTM 141
- polyalkylene glycol carbamates with fatty chains such as PPG-14 laureth isophoryl dicarbamate marketed under the name ELFACOSTM T211, PPG-14 palmeth-60 hexyl dicarbamate marketed under the
- thickening and/or gelling agents which can be combined with the polymer (P) in the said composition (F) as defined previously, mention may be made of the copolymers of AMPS and of alkyl acrylates whose carbon chain comprises between four and thirty carbon atoms and more particularly between ten and thirty carbon atoms, linear, branched or cross-linked terpolymers of at least one monomer possessing a strong, free, partially salified or totally salified acid function, with at at least one neutral monomer, and at least one monomer of formula (XXX):
- R' 3 represents a hydrogen atom or a methyl radical
- R' 4 represents a linear or branched alkyl radical comprising from eight to thirty carbon atoms and n′ represents a number greater than or equal to one and less than or equal to fifty.
- thickening and/or gelling agents which can be combined with the polymer (P) in the said composition (F) as defined above
- thickening and/or gelling agents which can be combined with the polymer (P) in the said composition (F) as defined above, mention may be made of polysaccharides consisting of derivatives of oses, such as sulphated galactans and more particularly carrageenans and agar, uronans and more particularly algins, alginates and pectins, heteropolymers of oses and uronic acids and more particularly xanthan gum, gellan gum, exudates of gum arabic and karaya gum, glucosaminoglycans.
- oses such as sulphated galactans and more particularly carrageenans and agar, uronans and more particularly algins, alginates and pectins, heteropolymers of oses and uronic acids and more particularly xanthan gum, gellan gum, exudates of gum arabic and karaya gum, glucosaminoglycans.
- thickening and/or gelling agents which can be combined with the polymer (P) in the said composition (F) as defined above, mention may be made of cellulose, cellulose derivatives such as methyl cellulose, ethyl cellulose, F hydroxypropyl cellulose, silicates, starch, hydrophilic derivatives of starch, polyurethanes.
- stabilizing agents which can be combined with the polymer (P) in the said composition (F) as defined above, mention may be made of microcrystalline waxes, and more particularly ozokerite, mineral salts such as sodium chloride or magnesium chloride, silicone polymers such as polysiloxane polyalkyl polyether copolymers.
- solvents which can be combined with the polymer (P) in the said composition (F) as defined above, mention may be made of water, organic solvents such as glycerol, diglycerol, glycerol oligomers, ethylene glycol, propylene glycol, butylene glycol, 1,3 -propanediol, 1,2-propanediol, hexylene glycol, diethylene glycol, xylitol, erythritol, sorbitol, water-soluble alcohols such as ethanol , isopropanol or butanol, mixtures of water and said organic solvents.
- organic solvents such as glycerol, diglycerol, glycerol oligomers, ethylene glycol, propylene glycol, butylene glycol, 1,3 -propanediol, 1,2-propanediol, hexylene glycol, diethylene glycol, xylitol, erythr
- thermal or mineral waters having a mineralization of at least 300 mg/l, in particular water from Avène, water from Vittel, water from the Vichy basin, water from Uriage, water from Roche Posay, water from La Bourboule, water from Enghien -les-bains, water from Saint-Gervais-les-bains, water from Néris-les-bains, water from Allevard-les-bains, water from Digne, water from Maizines, water from Neyrac-les-bains, water from Lons le Saunier, water from Rochefort, water from Saint Christau, water from Fumades and water from Tercis-les-bains.
- hydrotropic agents which can be combined with the polymer (P) in the said composition (F) as defined above, mention may be made of xylene sulphonates, cumene sulphonates, F hexylpolyglucoside, 2-ethylhexylpolyglucoside, n- heptylpolyglucoside.
- emulsifying surfactants which can be combined with the polymer (P) in the said composition (F) as defined above, mention may be made of nonionic surfactants, anionic surfactants, cationic surfactants.
- esters of fatty acids and of sorbitol such as the products marketed under the names MONTANETM40, MONTANETM60, MONTANETM70, MONTANETM80 and MONTANETM85; compositions comprising glycerol stearate and ethoxylated stearic acid between 5 moles and 150 moles of ethylene oxide, such as the composition comprising ethoxylated stearic acid at 135 moles of ethylene oxide and glycerol stearate marketed under the name SIMULSOLTM 165; mannitan esters; ethoxylated mannitan esters; sucrose esters; methylglucoside esters; alkylpolyglycosides comprising an aliphatic radical, linear or branched, saturated or unsaturated, and comprising from
- anionic surfactants which can be combined with the polymer (P) in the said composition (F) as defined above, mention may be made of glyceryl stearate citrate, cetearyl sulphate, soaps such as sodium stearate or triethanolammonium, N-acyl derivatives of salified amino acids, for example stearoyl glutamate.
- emulsifying cationic surfactants which can be combined with the polymer (P) in the said composition (F) as defined above, mention may be made of the amine oxides, quaternium-82 and the surfactants described in patent application W096/00719 and mainly those whose fatty chain comprises at least 16 carbon atoms.
- opacifying and/or pearlescent agents which can be combined with the polymer (P) in the said composition (F) as defined above, mention may be made of sodium palmitate, sodium stearate, sodium hydroxy stearate , magnesium palmitate, magnesium stearate, F hydroxy magnesium stearate, ethylene glycol monostearate, ethylene glycol distearate, polyethylene glycol monostearate, polyethylene glycol distearate, fatty alcohols comprising from 12 to 22 carbon atoms.
- texture agents which can be combined with the polymer (P) in the said composition (F) as defined previously, mention may be made of N-acylated derivatives of amino acids, such as lauroyl lysine marketed under the name AMINOHOPETMLL, octenyl starch succinate marketed under the name DRYFLOTM, myristyl polyglucoside marketed under the name MONTANOVTM 14, cellulose fibers, cotton fibers, chitosan fibers, talc, sericite , mica
- deodorant agents which can be combined with the polymer (P) in the said composition (F) as defined above, mention may be made of alkali metal silicates, zinc salts such as zinc sulphate, zinc gluconate, zinc chloride, zinc lactate; quaternary ammonium salts such as cetyltrimethylammonium salts, salts of cetylpyridinium; glycerol derivatives such as glycerol caprate, glycerol caprylate, polyglycerol caprate; 1,2 decanediol; 1,3 propanediol; salicylic acid; sodium bicarbonate; cyclodextrins; metallic zeolites; TRICLOSANTM; aluminum bromohydrate, aluminum hydrochlorides, aluminum chloride, aluminum sulphate, aluminum and zirconium hydrochlorides, aluminum and zirconium trihydrochloride, aluminum and zirconium tetrahydrochloride , aluminum zirconium pentahydrochlor
- waxes which can be combined with the polymer (P) in the said composition (F) as defined above, mention may be made of beeswax, carnauba wax, candelilla wax, ouricoury wax , Japan wax, cork fiber wax, sugar cane wax, paraffin waxes, lignite waxes, microcrystalline waxes, lanolin wax; ozokerite; polyethylene wax; silicone waxes; vegetable waxes; fatty alcohols and fatty acids which are solid at room temperature; solid glycerides at room temperature.
- waxes in the present application is meant compounds and/or mixtures of compounds that are insoluble in water, appearing in a solid appearance at a temperature greater than or equal to 45° C.
- vitamins and their derivatives in particular their esters, such as retinol (vitamin A) and its esters (e.g.
- vitamin C ascorbic acid
- vitamin E sugar derivatives of ascorbic acid (such as ascorbyl glucoside), tocopherol (vitamin E) and its esters (such as tocopherol acetate), vitamins B3 or B10 (niacinamide and its derivatives); compounds showing a lightening or depigmenting action on the skin such as co-undecelynoyl phenylalanine marketed under the name SEPIWHITETMMSH, SEPICALMTMVG, the mono ester and/or the glycerol diester of co-undecelynoyl phenylalanine, the co- undecelynoyl dipeptides, arbutin, kojic acid, F hydroquinone; compounds showing a soothing action, in particular SEPICALMTM S, allantoin and bisabolol; anti-inflammatory agents; compounds showing a moisturizing action such as urea, hydroxyureas, g
- Biotanning (INCI name: Hydrolyzed citrus Aurantium dulcis fruit extract) by the company Silab and known to be rich in lemon flavonoids (hesperidin type); agents intended for the treatment of hair and/or body hair, for example protective agents for the melanocytes of the hair follicle, intended to protect the said melanocytes against the cytotoxic agents responsible for the senescence and/or the apoptosis of the said melanocytes, such as mimetics of the activity of DOPAchrome tautomerase chosen from those described in the European patent application published under number EPI 515688 A2, synthetic molecules mimetic of SOD, for example manganese complexes, antioxidant compounds, for example derivatives of cyclodextrin, siliceous compounds derived from ascorbic acid, lysine or arginine pyrrolidone carboxylate, combinations of mono- and diester of cinnamic acid and vitamin C, and more generally those cited in the published European patent application under the number
- antioxidant agents which can be combined with the polymer (P) in the said composition (F) as defined above, mention may be made of EDTA and its salts, citric acid, tartaric acid, oxalic acid, BHA (butylhydroxyanisole), BHT (butylhydroxytoluene), tocopherol derivatives such as tocopherol acetate, mixtures of antioxidant compounds such as DISSOL VINETM GL 47S sold by Akzo Nobel under the INCI name: Tetrasodium Glutamate Diacetate.
- sunscreens that can be combined with the polymer (P) in said composition (F) as defined above, mention can be made of all those appearing in cosmetics directive 76/768/EEC, as amended in appendix VII.
- organic sunscreens that can be combined with the polymer (P) in said composition (F) as defined above, mention may be made of the family of benzoic acid derivatives such as para-aminobenzoic acids (PABA), in particular monoglycerol esters of PABA, ethyl esters of N,N25 propoxy PABA, ethyl esters of N,N-diethoxy PABA, ethyl esters of N,N-dimethyl PABA, methyl esters of N,N-dimethyl PABA, esters butyls of N,Ndimethyl PABA; the family of anthranilic acid derivatives such as homomenthyl-N-acetyl anthranilate; the family of salicylic acid derivatives such as amyl salicylate, homomenthyl salicylate, ethylhexyl salicylate, phenyl salicylate, benzyl salicylate, p-isopropanolphenyl salicylate;
- mineral screens which can be combined with the polymer (P) in the said composition (F) as defined above, mention may be made of titanium oxides, zinc oxides, cerium oxide, zirconium oxide, yellow, red or black iron oxides, chromium oxides. These mineral screens may or may not be micronized, may or may not have undergone surface treatments and may optionally be presented in the form of aqueous or oily pre-dispersions.
- Example 1 Preparation of a sodium PGGA according to the invention crosslinked with Polyethylene glycol Diglycidyl Ether and atomized:
- the synthesis process comprises the following 4 steps:
- Step 1) Production of an aqueous gel of sodium PGGA:
- the aqueous solution obtained in step 3 is concentrated by passage through an atomizer whose operating parameters are as follows:
- Circulating air temperature 150°C
- composition (El) is finally isolated in the form of a pulverulent powder.
- Example 2 Preparation of a sodium PGGA according to the invention crosslinked with L4-Butanediol diglycidyl ether and atomized:
- Example 1 The synthesis process of Example 1 is reproduced by replacing the 1.2 grams of Polyethylene glycol Diglycidyl Ether (PEGDGE) by 0.48 grams of 1,4-Butanediol Diglycidyl Ether sold under the name ERISYSTM GE 21 by EMERALD Company.
- PEGDGE Polyethylene glycol Diglycidyl Ether
- ERISYSTM GE 21 1,4-Butanediol Diglycidyl Ether sold under the name ERISYSTM GE 21 by EMERALD Company.
- composition (E2) obtained is finally isolated in the form of a pulverulent powder.
- a control was produced from non-crosslinked PGGA marketed by the Lubon Company under the name “cosmetic grade PGGA”.
- control sodium PGGA gels exhibit viscosities of between 100 and 200 mPa.s in the presence or absence of NaCl.
- crosslinked and atomized sodium PGGA gels In the absence of NaCl, crosslinked and atomized sodium PGGA gels have viscosities respectively equal to 30400 mPa.s in the case where the crosslinker is PEGDGE and 41520 mPa.s with ERISYSTM GE 21 as crosslinker . In the presence of NaCl, the viscosity of the gel of sodium PGGA crosslinked by PEGDGE and atomized is equal to 9320 mPa. s.
- compositions (E1) and (E2) according to the invention therefore make it possible to thicken aqueous phases.
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- Polymers & Plastics (AREA)
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Abstract
Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
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CN202180087862.0A CN117222690A (zh) | 2020-12-14 | 2021-11-30 | 呈粉状固体形式并具有增稠极性介质的特性的聚合物 |
JP2023535788A JP2024501468A (ja) | 2020-12-14 | 2021-11-30 | 粉状固体の形態を取り、且つ極性媒体を増粘するための特性を有するポリマー |
US18/256,553 US20240026078A1 (en) | 2020-12-14 | 2021-11-30 | Polymer taking the form of a pulverulent solid and having properties for thickening polar media |
EP21816480.4A EP4259693A1 (fr) | 2020-12-14 | 2021-11-30 | Polymère se présentant sous la forme d'un solide pulvérulent et présentant des propriétés épaississantes de milieux polaires |
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FR2013174A FR3117491B1 (fr) | 2020-12-14 | 2020-12-14 | Polymère se présentant sous la forme d’un solide pulvérulent et présentant des propriétés épaississantes de milieux polaires |
FR2013174 | 2020-12-14 |
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WO2022128452A1 true WO2022128452A1 (fr) | 2022-06-23 |
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PCT/EP2021/083620 WO2022128452A1 (fr) | 2020-12-14 | 2021-11-30 | Polymère se présentant sous la forme d'un solide pulvérulent et présentant des propriétés épaississantes de milieux polaires |
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US (1) | US20240026078A1 (fr) |
EP (1) | EP4259693A1 (fr) |
JP (1) | JP2024501468A (fr) |
CN (1) | CN117222690A (fr) |
FR (1) | FR3117491B1 (fr) |
WO (1) | WO2022128452A1 (fr) |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1996000719A1 (fr) | 1994-06-28 | 1996-01-11 | Societe D'exploitation De Produits Pour Les Industries Chimiques-Seppic | Nouveaux derives d'ammoniums quaternaires, leur procede de preparation et leur utilisation comme agents de surface |
EP0971683A1 (fr) | 1997-04-04 | 2000-01-19 | L'oreal | Compositions comprenant des santalines, santarubines pour la coloration artificielle de la peau |
EP1515688A2 (fr) | 2002-06-11 | 2005-03-23 | L'oreal | Utilisation d un agent mimetique de l activite de la do pachrome tautomerase (trp-2) comme agent protecteur des melanocytes du follicule pileux et applications |
WO2018222545A1 (fr) * | 2017-05-27 | 2018-12-06 | Ecovia Renewables Inc. | Compositions de modificateur de rhéologie de poly(acide aminé) et procédés d'utilisation |
-
2020
- 2020-12-14 FR FR2013174A patent/FR3117491B1/fr active Active
-
2021
- 2021-11-30 US US18/256,553 patent/US20240026078A1/en active Pending
- 2021-11-30 EP EP21816480.4A patent/EP4259693A1/fr active Pending
- 2021-11-30 WO PCT/EP2021/083620 patent/WO2022128452A1/fr active Application Filing
- 2021-11-30 JP JP2023535788A patent/JP2024501468A/ja active Pending
- 2021-11-30 CN CN202180087862.0A patent/CN117222690A/zh active Pending
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1996000719A1 (fr) | 1994-06-28 | 1996-01-11 | Societe D'exploitation De Produits Pour Les Industries Chimiques-Seppic | Nouveaux derives d'ammoniums quaternaires, leur procede de preparation et leur utilisation comme agents de surface |
EP0971683A1 (fr) | 1997-04-04 | 2000-01-19 | L'oreal | Compositions comprenant des santalines, santarubines pour la coloration artificielle de la peau |
EP1515688A2 (fr) | 2002-06-11 | 2005-03-23 | L'oreal | Utilisation d un agent mimetique de l activite de la do pachrome tautomerase (trp-2) comme agent protecteur des melanocytes du follicule pileux et applications |
WO2018222545A1 (fr) * | 2017-05-27 | 2018-12-06 | Ecovia Renewables Inc. | Compositions de modificateur de rhéologie de poly(acide aminé) et procédés d'utilisation |
Also Published As
Publication number | Publication date |
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CN117222690A (zh) | 2023-12-12 |
FR3117491B1 (fr) | 2024-01-19 |
JP2024501468A (ja) | 2024-01-12 |
EP4259693A1 (fr) | 2023-10-18 |
US20240026078A1 (en) | 2024-01-25 |
FR3117491A1 (fr) | 2022-06-17 |
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