DE19505005C2 - Cationized vegetable protein surfactants - Google Patents
Cationized vegetable protein surfactantsInfo
- Publication number
- DE19505005C2 DE19505005C2 DE19505005A DE19505005A DE19505005C2 DE 19505005 C2 DE19505005 C2 DE 19505005C2 DE 19505005 A DE19505005 A DE 19505005A DE 19505005 A DE19505005 A DE 19505005A DE 19505005 C2 DE19505005 C2 DE 19505005C2
- Authority
- DE
- Germany
- Prior art keywords
- cationized
- vegetable protein
- quaternary ammonium
- ammonium salts
- range
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000004094 surface-active agent Substances 0.000 title claims description 15
- 108010082495 Dietary Plant Proteins Proteins 0.000 title claims description 11
- 239000003531 protein hydrolysate Substances 0.000 claims description 50
- 241000209140 Triticum Species 0.000 claims description 43
- 235000021307 Triticum Nutrition 0.000 claims description 43
- 102000035195 Peptidases Human genes 0.000 claims description 23
- 108091005804 Peptidases Proteins 0.000 claims description 23
- 235000019833 protease Nutrition 0.000 claims description 22
- -1 2-hydroxy-3-chloro-n-propyl Chemical group 0.000 claims description 17
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 12
- 235000018102 proteins Nutrition 0.000 claims description 11
- 102000004169 proteins and genes Human genes 0.000 claims description 11
- 108090000623 proteins and genes Proteins 0.000 claims description 11
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 10
- 108010084695 Pea Proteins Proteins 0.000 claims description 8
- 108010009736 Protein Hydrolysates Proteins 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 235000019702 pea protein Nutrition 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 230000007062 hydrolysis Effects 0.000 claims description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 125000002091 cationic group Chemical group 0.000 description 29
- 229930182478 glucoside Natural products 0.000 description 21
- 150000008131 glucosides Chemical class 0.000 description 20
- 229940057950 sodium laureth sulfate Drugs 0.000 description 19
- 102000008186 Collagen Human genes 0.000 description 17
- 108010035532 Collagen Proteins 0.000 description 17
- 229920001436 collagen Polymers 0.000 description 17
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 15
- 235000014113 dietary fatty acids Nutrition 0.000 description 15
- 239000000194 fatty acid Substances 0.000 description 15
- 229930195729 fatty acid Natural products 0.000 description 15
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 13
- 235000002639 sodium chloride Nutrition 0.000 description 13
- 150000004665 fatty acids Chemical class 0.000 description 10
- SXHLENDCVBIJFO-UHFFFAOYSA-M sodium;2-[2-(2-dodecoxyethoxy)ethoxy]ethyl sulfate Chemical compound [Na+].CCCCCCCCCCCCOCCOCCOCCOS([O-])(=O)=O SXHLENDCVBIJFO-UHFFFAOYSA-M 0.000 description 10
- FPVVYTCTZKCSOJ-UHFFFAOYSA-N Ethylene glycol distearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCOC(=O)CCCCCCCCCCCCCCCCC FPVVYTCTZKCSOJ-UHFFFAOYSA-N 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- AZLWQVJVINEILY-UHFFFAOYSA-N 2-(2-dodecoxyethoxy)ethanol Chemical compound CCCCCCCCCCCCOCCOCCO AZLWQVJVINEILY-UHFFFAOYSA-N 0.000 description 8
- 229920002884 Laureth 4 Polymers 0.000 description 8
- MRUAUOIMASANKQ-UHFFFAOYSA-N cocamidopropyl betaine Chemical compound CCCCCCCCCCCC(=O)NCCC[N+](C)(C)CC([O-])=O MRUAUOIMASANKQ-UHFFFAOYSA-N 0.000 description 8
- SFNALCNOMXIBKG-UHFFFAOYSA-N ethylene glycol monododecyl ether Chemical compound CCCCCCCCCCCCOCCO SFNALCNOMXIBKG-UHFFFAOYSA-N 0.000 description 8
- 229940100608 glycol distearate Drugs 0.000 description 8
- 229940100491 laureth-2 Drugs 0.000 description 8
- 229940061515 laureth-4 Drugs 0.000 description 8
- 239000011780 sodium chloride Substances 0.000 description 8
- 229940081733 cetearyl alcohol Drugs 0.000 description 7
- 229940073507 cocamidopropyl betaine Drugs 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 229940075529 glyceryl stearate Drugs 0.000 description 7
- 239000002453 shampoo Substances 0.000 description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 6
- 229940073669 ceteareth 20 Drugs 0.000 description 6
- 239000003925 fat Substances 0.000 description 6
- 235000011187 glycerol Nutrition 0.000 description 6
- 102000004196 processed proteins & peptides Human genes 0.000 description 6
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
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- 239000000975 dye Substances 0.000 description 5
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- 229940074046 glyceryl laurate Drugs 0.000 description 5
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- 229940086539 peg-7 glyceryl cocoate Drugs 0.000 description 5
- 239000011591 potassium Substances 0.000 description 5
- 229910052700 potassium Inorganic materials 0.000 description 5
- ARIWANIATODDMH-UHFFFAOYSA-N rac-1-monolauroylglycerol Chemical compound CCCCCCCCCCCC(=O)OCC(O)CO ARIWANIATODDMH-UHFFFAOYSA-N 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- LEACJMVNYZDSKR-UHFFFAOYSA-N 2-octyldodecan-1-ol Chemical compound CCCCCCCCCCC(CO)CCCCCCCC LEACJMVNYZDSKR-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- 239000003463 adsorbent Substances 0.000 description 4
- 229940024606 amino acid Drugs 0.000 description 4
- 235000001014 amino acid Nutrition 0.000 description 4
- 150000001413 amino acids Chemical class 0.000 description 4
- BTFJIXJJCSYFAL-UHFFFAOYSA-N arachidyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCO BTFJIXJJCSYFAL-UHFFFAOYSA-N 0.000 description 4
- SASYSVUEVMOWPL-NXVVXOECSA-N decyl oleate Chemical compound CCCCCCCCCCOC(=O)CCCCCCC\C=C/CCCCCCCC SASYSVUEVMOWPL-NXVVXOECSA-N 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- 229920001184 polypeptide Polymers 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000001993 wax Substances 0.000 description 4
- 229920001661 Chitosan Polymers 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 230000000035 biogenic effect Effects 0.000 description 3
- 239000003093 cationic surfactant Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000002304 perfume Substances 0.000 description 3
- 239000003755 preservative agent Substances 0.000 description 3
- JJMIAJGBZGZNHA-UHFFFAOYSA-N sodium;styrene Chemical compound [Na].C=CC1=CC=CC=C1 JJMIAJGBZGZNHA-UHFFFAOYSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 239000002562 thickening agent Substances 0.000 description 3
- NKJOXAZJBOMXID-UHFFFAOYSA-N 1,1'-Oxybisoctane Chemical compound CCCCCCCCOCCCCCCCC NKJOXAZJBOMXID-UHFFFAOYSA-N 0.000 description 2
- FLPJVCMIKUWSDR-UHFFFAOYSA-N 2-(4-formylphenoxy)acetamide Chemical compound NC(=O)COC1=CC=C(C=O)C=C1 FLPJVCMIKUWSDR-UHFFFAOYSA-N 0.000 description 2
- YBRJTUFWBLSLHY-UHFFFAOYSA-N 2-[2-(2-octadecanoyloxyethoxy)ethoxy]ethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCOCCOCCOC(=O)CCCCCCCCCCCCCCCCC YBRJTUFWBLSLHY-UHFFFAOYSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- XVZIAZAFOVOYAT-TTWKNDKESA-N 2-methyloxirane;(e)-octadec-9-enoic acid;oxirane Chemical compound C1CO1.CC1CO1.CCCCCCCC\C=C\CCCCCCCC(O)=O XVZIAZAFOVOYAT-TTWKNDKESA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 241001340526 Chrysoclista linneella Species 0.000 description 2
- 108010016626 Dipeptides Proteins 0.000 description 2
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- 108700035782 EC 3.4.3.- Proteins 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 102000011782 Keratins Human genes 0.000 description 2
- 108010076876 Keratins Proteins 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 108010022999 Serine Proteases Proteins 0.000 description 2
- 102000012479 Serine Proteases Human genes 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
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- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
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- 229940079868 disodium laureth sulfosuccinate Drugs 0.000 description 2
- YGAXLGGEEQLLKV-UHFFFAOYSA-L disodium;4-dodecoxy-4-oxo-2-sulfonatobutanoate Chemical compound [Na+].[Na+].CCCCCCCCCCCCOC(=O)CC(C([O-])=O)S([O-])(=O)=O YGAXLGGEEQLLKV-UHFFFAOYSA-L 0.000 description 2
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- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- UBHWBODXJBSFLH-UHFFFAOYSA-N hexadecan-1-ol;octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO.CCCCCCCCCCCCCCCCCCO UBHWBODXJBSFLH-UHFFFAOYSA-N 0.000 description 2
- PXDJXZJSCPSGGI-UHFFFAOYSA-N hexadecanoic acid hexadecyl ester Natural products CCCCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCCCC PXDJXZJSCPSGGI-UHFFFAOYSA-N 0.000 description 2
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- REZZEXDLIUJMMS-UHFFFAOYSA-M dimethyldioctadecylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC REZZEXDLIUJMMS-UHFFFAOYSA-M 0.000 description 1
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- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
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- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
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- 125000003976 glyceryl group Chemical group [H]C([*])([H])C(O[H])([H])C(O[H])([H])[H] 0.000 description 1
- 239000003676 hair preparation Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
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- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
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- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
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- BOUCRWJEKAGKKG-UHFFFAOYSA-N n-[3-(diethylaminomethyl)-4-hydroxyphenyl]acetamide Chemical compound CCN(CC)CC1=CC(NC(C)=O)=CC=C1O BOUCRWJEKAGKKG-UHFFFAOYSA-N 0.000 description 1
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- 229940120511 oleyl erucate Drugs 0.000 description 1
- 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 description 1
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- 125000001151 peptidyl group Chemical group 0.000 description 1
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
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- 239000002244 precipitate Substances 0.000 description 1
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- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
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- 239000004334 sorbic acid Substances 0.000 description 1
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- 229940033331 soy sterol Drugs 0.000 description 1
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- 239000003760 tallow Substances 0.000 description 1
- OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 229960004072 thrombin Drugs 0.000 description 1
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- 239000012588 trypsin Substances 0.000 description 1
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- 235000013343 vitamin Nutrition 0.000 description 1
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
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- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/30—Proteins; Protein hydrolysates
-
- 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
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/41—Amines
- A61K8/416—Quaternary ammonium compounds
-
- 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
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/64—Proteins; Peptides; Derivatives or degradation products thereof
-
- 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
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/64—Proteins; Peptides; Derivatives or degradation products thereof
- A61K8/645—Proteins of vegetable origin; Derivatives or degradation products thereof
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/16—Amines or polyamines
-
- 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
- A61Q19/10—Washing or bathing preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/02—Preparations for cleaning the hair
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Molecular Biology (AREA)
- Dermatology (AREA)
- Cosmetics (AREA)
Description
Die Erfindung betrifft kationisierte Proteinhydrolysate auf Basis von Weizen- und/oder Erbsenprotein, ein Verfahren zu ihrer Herstellung durch definierten enzymatischen Abbau der Ausgangsproteine und nachfolgende Quaternierung der Hydrolysate sowie die Verwendung der Stoffe zur Herstellung von oberflächenaktiven Mitteln.The invention relates to cationized protein hydrolysates based on wheat and / or pea protein, a process for their preparation by defined enzymatic degradation of the starting proteins and subsequent quaternization of the hydrolysates and the use of the substances for the production of surfactants.
Abbauprodukte von Polypeptiden, sogenannte Proteinhydrolysate, sind seit langem bekannt. Obschon sie wegen des Fehlens einer lipophilen Gruppe keine Detergenseigenschaften besitzen, werden sie wegen ihrer dispergierenden Eigenschaften und ihrer Fähigkeit, die dermatologische Verträglichkeit anionischer Tenside durch Wechselwirkung mit den Eiweißmolekülen der Haut günstig zu beeinflussen, in einer Vielzahl von oberflächenaktiven Mitteln eingesetzt. Übersichtsartikel hierzu finden sich beispielsweise von A.Domsch et al. in Ärztl. Kosmetol. 13, 524 (1983), G.Schuster et al. in Cosmet. Toil., 99, 12 (1984) und H.Lindner in Parfüm.Kosmet., 66, 85 (1985).Degradation products of polypeptides, so-called protein hydrolysates, have long been known. Although they do not have detergent properties due to the lack of a lipophilic group they become because of their dispersing properties and their dermatological compatibility anionic surfactants favorably influenced by interaction with the protein molecules of the skin, used in a variety of surfactants. Reviews can be found here for example, by A.Domsch et al. in doctor Kosmetol. 13, 524 (1983), G. Schuster et al. in Cosmet. Toil., 99, 12 (1984) and H. Lindner in Parfum. Cosmet., 66, 85 (1985).
Auch kationisierte Proteintenside auf Basis von tierischem Kollagen oder Keratin, aber auch auf Basis von Soja- und Weizenprotein sind bekannt [vgl. Firmenschrift "Cosmetic Ingredients & Ideas", Brroks Industries Inc., Issue # 14, (1994)] und werden überwiegend in haarkosmetischen Mitteln ein gesetzt. Hier besteht jedoch der Nachteil, daß die Produkte häufig dunkel verfärbt sind, in wäßriger Lö sung nicht ausreichend lagerstabil sind und zu Austrübungen neigen und auch im Hinblick auf ihre der matologische Verträglichkeit nicht voll zufriedenstellend sind. Schließlich besteht ein Bedarf an Pro dukten mit verbesserten antistatischen und avivierenden Eigenschaften.Also cationized protein surfactants based on animal collagen or keratin, but also based of soy and wheat protein are known [cf. Company publication "Cosmetic Ingredients & Ideas", Brroks Industries Inc., Issue # 14, (1994)] and are predominantly used in hair cosmetics set. Here, however, there is the disadvantage that the products are often discolored dark, in aqueous Lö are not sufficiently stable in storage and prone to clouding and also with regard to their matological compatibility are not fully satisfactory. Finally, there is a need for Pro products with improved antistatic and scavenging properties.
Die Aufgabe der Erfindung hat somit darin bestanden, neue kationisierte Proteintenside zur Verfügung zu stellen, die frei von den geschilderten Nachteilen sind, über eine verbesserte Farbqualität und Lagerstabilität, eine vergleichsweise höhere dermatologische Verträglichkeit und schließlich auch verbesserte anwendungstechnische Eigenschaften verfügen. The object of the invention has thus been to provide new cationized protein surfactants to provide, which are free from the disadvantages described above an improved color quality and Storage stability, a comparatively higher dermatological compatibility and finally have improved performance characteristics.
Gegenstand der Erfindung sind kationisierte pflanzliche Proteinhydrolysate, die man erhält, indem man Weizen- und/oder ErbsenproteinThe invention relates to cationized vegetable protein hydrolysates obtained by Wheat and / or pea protein
- (a) zunächst bei einem pH-Wert im Bereich von 8 bis 10 mit Proteinasen und dann(a) first at a pH in the range of 8 to 10 with proteinases and then
- (b) bei einem pH-Wert im Bereich von 6 bis 7 mit Peptidasen hydrolysiert, und schließlich(b) hydrolyzed at a pH in the range of 6 to 7 with peptidases, and finally
- (c) das erhaltene Hydrolysat mit quartären Ammoniumsalzen umsetzt.(c) reacting the resulting hydrolyzate with quaternary ammonium salts.
Überraschenderweise wurde gefunden, daß die Quaternierung von Proteinhydrolysaten auf Basis von Weizen- und/oder Erbsenprotein zu kationischen Tensiden führt, die nicht nur besonders hellfarbig, sondern auch ausgesprochen augenschleimhautverträglich sind. Die neuen kationischen Tenside sind ferner in wäßriger Lösung stabil, d. h. trüben auch bei längerer Lagerung nicht aus und weisen gegen über vergleichbaren Produkten auf Kollagenbasis auch eine höhere avivierende Wirkung auf.Surprisingly, it has been found that the quaternization of protein hydrolysates based on Wheat and / or pea protein leads to cationic surfactants that are not only particularly light-colored, but also pronounced ocular mucosa are compatible. The new cationic surfactants are further stable in aqueous solution, d. H. Do not tarnish even during prolonged storage and reject also has a higher avivating effect on comparable products based on collagen.
Ein weiterer Gegenstand der Erfindung betrifft ein Verfahren zur Herstellung von kationisierten pflanzli chen Proteinhydrolysaten, bei dem man Weizen- und/oder ErbsenproteinAnother object of the invention relates to a process for the preparation of cationized Pflanzenli protein hydrolysates, which include wheat and / or pea protein
- (a) zunächst bei einem pH-Wert im Bereich von 8 bis 10 mit Proteinasen und dann(a) first at a pH in the range of 8 to 10 with proteinases and then
- (b) bei einem pH-Wert im Bereich von 6 bis 7 mit Peptidasen hydrolysiert, und schließlich(b) hydrolyzed at a pH in the range of 6 to 7 with peptidases, and finally
- (c) das erhaltene Hydrolysat mit quartären Ammoniumsalzen umsetzt.(c) reacting the resulting hydrolyzate with quaternary ammonium salts.
Die pflanzliche Proteinhydrolysate stellen Abbauprodukte von Weizen- und/oder Erbsenprotein dar, die durch saure, alkalische und/oder enzymatische Hydrolyse gespalten werden und danach ein durch schnittliches Molekulargewicht im Bereich von 600 bis 4000, vorzugsweise 2000 bis 3500 aufweisen.The vegetable protein hydrolysates are degradation products of wheat and / or pea protein, which be cleaved by acid, alkaline and / or enzymatic hydrolysis and then by a average molecular weight in the range of 600 to 4000, preferably 2000 to 3500 have.
Proteinasen und Peptidasen zählen zur Gruppe der Proteasen, also Enzymen, welche die hydrolytische Spaltung der Peptidbindung katalysieren und daher systematisch gesehen zu den Hydrolasen gehören. Proteinasen, die auch als Endoproteasen oder Endopeptidasen bezeichnet werden, spalten Peptidbin dungen im Inneren des Proteins. Sie sind von den (Exo-)Peptidasen zu unterscheiden, die einen Abbau an der Amino- oder Carboxylgruppe bewirken. Typische Beispiele für im Sinne des erfindungsgemäßen Verfahrens geeignete Proteinasen sind die im Handel erhältlichen Serin-Proteinasen (EC 3.4.21), Cystein- bzw. Thiol-Proteinasen (EC 3.4.22), saure Proteinasen vom Typ der Aspartat- bzw. Carboxyproteinasen (EC 3.4.23) sowie untergeordnet auch Metall-Proteinasen (EC 3.4.24). Beispiele für geeignete Serin-Proteinasen sind Chymotrypsin, Elastase, Kallikrein, Plasmin, Trypsin, Thrombin und Subtilisin. Zu den geeigneten Peptidasen zählen beispielsweise die α-Aminoacylpeptid- Hydrolasen oder Aminopeptidasen (EC 3.4.11), die am Ende des Polypeptids einzelne Aminosäuren ablösen, die Dipeptid-Hydrolasen bzw. Dipeptidasen (EC 3.4.13), die Dipeptide zu Aminosäuren hydrolysieren, die Dipeptidylpeptid-Hydrolasen bzw. Dipeptidylpeptidasen (EC 3.4.14), die Aminostän dige Dipeptide eines Polypeptids freisetzen, Peptidyldipeptid-Hydrolasen bzw. Dipeptidylcarboxy-pep tidasen (EC 3.4.15), die einzelne Aminosäuren des Carboxy-Terminus abtrennen, Carboxypeptidasen (EC 3.4.16 - 3.4.18) und Omega-Peptidasen (EC 3.4.19), die modifizierte Aminosäuren von beiden Ende des Polypeptids abspalten. Die Menge der eingesetzten Proteinasen bzw. Peptidasen ist an sich nicht kritisch, sollte jedoch jeweils im Bereich von 0,1 bis 5, vorzugsweise 0,5 bis 2 Gew.-% - bezogen auf die Ausgangsstoffe - liegen.Proteinases and peptidases belong to the group of proteases, ie enzymes, which are hydrolytic Catalyze cleavage of the peptide bond and therefore belong systematically to the hydrolases. Proteinases, also referred to as endoproteases or endopeptidases, cleave peptide bin tions inside the protein. They are to be distinguished from the (exo-) peptidases, which are a degradation effect on the amino or carboxyl group. Typical examples for the purposes of the invention Suitable proteinases are the commercially available serine proteinases (EC 3.4.21), Cysteine or thiol proteinases (EC 3.4.22), acidic proteinases of the aspartate or Carboxyproteinases (EC 3.4.23) as well as subordinate metalloproteinases (EC 3.4.24). Examples suitable serine proteinases include chymotrypsin, elastase, kallikrein, plasmin, trypsin, thrombin and subtilisin. Suitable peptidases include, for example, the α-aminoacylpeptide Hydrolases or aminopeptidases (EC 3.4.11), which at the end of the polypeptide single amino acids replace the dipeptide hydrolases or dipeptidases (EC 3.4.13), the dipeptides to amino acids hydrolyze, the dipeptidyl-peptide hydrolases or dipeptidyl peptidases (EC 3.4.14), the Aminostän release dipeptides of a polypeptide peptidyl dipeptide hydrolases or dipeptidylcarboxy-pep tidases (EC 3.4.15) that separate single amino acids of the carboxy terminus, carboxypeptidases (EC 3.4.16 - 3.4.18) and omega peptidases (EC 3.4.19), the modified amino acids of both Cleave off the end of the polypeptide. The amount of proteinases or peptidases used is per se not critical, but should in each case in the range of 0.1 to 5, preferably 0.5 to 2 wt .-% - related on the starting materials - lie.
Zur Entfernung von Spuren an unerwünschten Farbverursachern hat es sich als vorteilhaft erwiesen, die proteinhaltigen Ausgangsstoffe zusammen mit geeigneten Adsorbentien in die Hydrolyse einzu setzen. Als Adsorbentien kommen beispielsweise Kieselgele, Aluminiumoxide und vorzugsweise Aktivkohlen in Betracht, die in Mengen von 0,1 bis 15, vorzugsweise 1 bis 5 Gew.-% - bezogen auf den Stickstoffgehalt der proteinhaltigen Ausgangsstoffe - eingesetzt werden können.To remove traces of unwanted colorants, it has proven to be advantageous the protein-containing starting materials enter into the hydrolysis together with suitable adsorbents put. As adsorbents, for example, silica gels, aluminum oxides and preferably Activated carbons into consideration, in amounts of 0.1 to 15, preferably 1 to 5 wt .-% - based on the Nitrogen content of protein-containing starting materials - can be used.
Zur Durchführung der enzymatischen Hydrolyse wird eine wäßrige Suspension des proteinhaltigen Ausgangsstoffs gegebenenfalls zusammen mit den Adsorbentien wie oben beschrieben bei wech selnden pH-Werten über einen Zeitraum von 1 bis 24 h im Temperaturoptimum der eingesetzten Proteinasen und Peptidasen unterhalb von 70 und vorzugsweise unterhalb von 60°C, beispielsweise bei 30 bis 55°C abgebaut. Im Anschluß an die Hydrolyse empfiehlt es sich, den pH-Wert in den sauren Bereich, beispielsweise auf pH = 3 bis 4 zu verschieben. Wird der Aufschluß in Gegenwart von Calciumoxid bzw. Calciumhydroxid als Base durchgeführt, bilden sich Calciumpeptide, die vom Rückstand abfiltriert werden müssen. Werden die Alkalipeptide gewünscht, empfiehlt es sich, die Cal ciumpeptide mit Soda- oder Pottaschelösung zu behandeln und das schwerlösliche Calciumcarbonat anschließend abzutrennen. Es ist ebenfalls möglich, das Calcium in Form von Calciumsulfat oder Calciumoxalat zu fällen. Die Abtrennung der schwerlöslichen Salze erfolgt vorzugsweise in Gegenwart von Filterhilfsmitteln über Filternutschen oder Filterpressen. Es werden wäßrige Pflanzenproteinhydro lysatlösungen erhalten, die nach Bedarf beispielsweise unter Einsatz von Fallstromverdampfern auf konzentriert werden können. Die dabei erhältlichen Hydrolysate weisen ein mittleres Molekulargewicht im Bereich von 100 bis 30.000, vorzugsweise 100 bis 10.000 und insbesondere 2000 bis 5000 auf sowie einen Feststoffgehalt von etwa 5 bis 50 Gew.-%.To carry out the enzymatic hydrolysis, an aqueous suspension of the proteinaceous Starting material optionally together with the adsorbents as described above in wech selnden pH values over a period of 1 to 24 h in the optimum temperature of the used Proteinases and peptidases below 70 and preferably below 60 ° C, for example degraded at 30 to 55 ° C. Following the hydrolysis, it is recommended that the pH in the acidic Range, for example, to pH = 3 to 4 to move. If the digestion in the presence of Calcium oxide or calcium hydroxide carried out as a base, calcium peptides formed by the Residue must be filtered off. If the alkali peptides are desired, it is recommended that the Cal ciumpeptide with soda or potash solution to treat and the sparingly soluble calcium carbonate then separate. It is also possible to use the calcium in the form of calcium sulfate or Precipitate calcium oxalate. The separation of the sparingly soluble salts is preferably carried out in the presence filter aids via filter suction or filter presses. There are aqueous vegetable protein hydro obtained lysate solutions, as needed, for example, using falling-stream evaporators on can be concentrated. The available hydrolysates have an average molecular weight in the range of 100 to 30,000, preferably 100 to 10,000 and especially 2000 to 5,000 and a solids content of about 5 to 50 wt .-%.
Die Kationisierung der pflanzlichen Proteinhydrolysate findet zwischen den freien Amino- und/oder Carboxylgruppen des Oligopeptids und einer Halogengruppe des eingesetzten quartären Ammonium salzes statt, wobei Halogenwasserstoff abgespalten wird. Die bevorzugt eingesetzten quartären Ammo niumsalze folgen der Formel (I),The cationization of vegetable protein hydrolysates takes place between the free amino and / or Carboxyl groups of the oligopeptide and a halogen group of the quaternary ammonium used salts, whereby hydrogen halide is split off. The preferably used quaternary ammo Niumsalze follow the formula (I),
in der R¹ für einen Alkyl- und/oder Alkenylrest mit 1 bis 22 Kohlenstoffatomen, R² und R³ unabhängig voneinander für einen Alkylrest mit 1 bis 4 Kohlenstoffatomen, Z für einen gegebenenfalls hy droxysubstituierten Alkylenrest sowie X und Hal unabhängig voneinander für Chlor oder Brom stehen. In einer besonderen Ausführungsform der Erfindung setzt man als quartäre Ammoniumsalze N,N-Dime thyl-N-(n-Alkyl)-N-(2-hydroxy-3-chloro-n-propyl)-ammoniumhalogenide und insbesondere N,N-Dimethyl- N-(n-Dodecyl)-N-(2-hydroxy-3-chloro-n-propyl)-ammoniumchlorid ein.in the R¹ is an alkyl and / or alkenyl radical having 1 to 22 carbon atoms, R² and R³ are independently each other for an alkyl radical having 1 to 4 carbon atoms, Z is an optionally hy Droxy-substituted alkylene radical and X and Hal independently represent chlorine or bromine. In a particular embodiment of the invention, the quaternary ammonium salts used are N, N-dime ethyl N- (n-alkyl) -N- (2-hydroxy-3-chloro-n-propyl) ammonium halides and in particular N, N-dimethyl N- (n-dodecyl) -N- (2-hydroxy-3-chloro-n-propyl) ammonium chloride.
Die Umsetzung zwischen den Proteinhydrolysaten und den quartären Ammoniumsalzen findet wie schon erwähnt unter Abspaltung von Halogenwasserstoff statt und wird durch Alkalibasen katalysiert. Die Auswahl dieser Basen ist an sich unkritisch, vorzugsweise werden jedoch konzentrierte wäßrige Lösungen von Natrium- oder Kaliumhydroxid eingesetzt. Der pH-Wert während der Umsetzung liegt demzufolge vorzugsweise im Bereich von 8 bis 12 und insbesondere um 10. Es hat sich als vorteilhaft erwiesen, die molaren Einsatzverhältnisse so zu wählen, daß auf ein 1 Mol eines Proteinhydrolysates, das im Mittel p Mol Peptideinheiten aufweist, p/10 bis p/100 Mol und vorzugsweise p/20 bis p/50 Mol quartäre Ammoniumsalze entfallen. Anders ausgedrückt bedeutet dies, daß auf ein 1 Mol eines Proteinhydrolysates, das im Mittel 100 Peptideinheiten aufweist (p = 100), 1 bis 10 Mol (p/100 bis p/10) und vorzugsweise 2 bis 5 (p/50 bis p/20) quartäre Ammoniumsalze eingesetzt werden. Die Umsetzung findet üblicherweise bei einer Temperatur im Bereich von 20 bis 90, vorzugsweise 40 bis 60°C statt; die Reaktionszeit liegt typischerweise bei 1 bis 24 und insbesondere 4 bis 12 h. Es hat sich als vorteilhaft erwiesen, das Endprodukt durch Zugabe von Mineralsäure auf einen neutralen pH-Wert einzustellen und in üblicher Weise, also beispielsweise durch Zugabe von pHB-Estern gegen mikrobiellen Befall zu stabilisieren.The reaction between the protein hydrolyzates and the quaternary ammonium salts takes place as already mentioned with elimination of hydrogen halide instead and is catalyzed by alkali metal bases. The choice of these bases is not critical per se, but are preferably concentrated aqueous Solutions of sodium or potassium hydroxide used. The pH during the reaction is therefore, preferably in the range of 8 to 12 and especially around 10. It has proved to be advantageous proved to choose the molar ratios so that a 1 mol of a protein hydrolyzate, having on average p moles of peptide units, p / 10 to p / 100 moles, and preferably p / 20 to p / 50 moles Quaternary ammonium salts omitted. In other words, this means that to a 1 mole of a Protein hydrolyzate having an average of 100 peptide units (p = 100), 1 to 10 moles (p / 100 to p / 10) and preferably 2 to 5 (p / 50 to p / 20) quaternary ammonium salts are used. The implementation usually takes place at a temperature in the range of 20 to 90, preferably 40 to 60 ° C instead; the Reaction time is typically 1 to 24 and especially 4 to 12 hours. It has proven to be beneficial proved to adjust the final product by the addition of mineral acid to a neutral pH and in the usual way, so for example by the addition of pHB esters against microbial infestation stabilize.
Die erfindungsgemäßen kationisierten Weizen- und Erbsenproteinhydrolysate sind ausgesprochen hellfarbig, weisen ausgezeichnete antistatische und haaravivierende Eigenschaften auf und sind aus dermatologischer Sicht signifikant verträglicher als vergleichbare Produkte auf Basis tierischen Kol lagens. Ein weiterer Gegenstand der Erfindung betrifft daher ihre Verwendung zur Herstellung von oberflächenaktiven Mitteln, insbesondere solchen zur Haar- und Körperpflege.The cationized wheat and pea protein hydrolysates according to the invention are pronounced light-colored, have excellent antistatic and hair-revitalizing properties and are off dermatological view significantly more compatible than comparable products based on animal col lagens. Another object of the invention therefore relates to their use for the production of surfactants, especially those for hair and body care.
Die Haut- und Haarpflegemittel können in untergeordneten Mengen weitere, mit den anderen Inhalts stoffen kompatible Tenside enthalten. Typische Beispiele sind Fettalkoholpolyglycolethersulfate, Mono glyceridsulfate, Ethercarbonsäuren, Mono- und/oder Dialkylsulfosuccinate, Fettsäureisethionate, Fett säuridesarcosinate, Fettsäuretauride, Alkyl- und/oder Alkenyloligoglucoside, Fettsäure-N-alkylpoly hydroxyalkylamide, Alkylamidobetaine und/oder Proteinhydrolysate bzw. deren Kondensate mit Fett säuren auf tierischer oder vorzugsweise pflanzlicher Basis. In besonderer Weise bevorzugt sind kos metische Mittel, die die kationonisierten Weizen- bzw. Erbsenproteintenside zusammen mit Alkyl oligoglucosiden und/oder Fettsäure-N-methylglucamiden enthalten. Das Mischungsverhältnis kann da bei 10 : 90 bis 90 : 10, vorzugsweise 25 : 75 bis 75 : 25 und insbesondere 40 : 60 bis 60 : 40 betragen. Ferner ist es selbstverständlich möglich, die erfindungsgemäßen kationisierten pflanzlichen Pro teintenside mit weiteren bekannten kationischen Tensiden, also beispielsweise typischen quartären Ammoniumsalzen wie Dimethyldistearylammoniumchlorid oder Benzyltrimethylammoniumchlorid sowie quaternierten Fettsäuretriethanolammoniumsalzen ("Esterquats") sowie bekannten Esterquat/Fett alkohol-Compounds abzumischen.The skin and hair products can be added in minor amounts, with the other content contain compatible surfactants. Typical examples are fatty alcohol polyglycol ether sulfates, mono glyceride sulfates, ether carboxylic acids, mono- and / or dialkyl sulfosuccinates, fatty acid isethionates, fat acid dysarcosinates, fatty acid taurides, alkyl and / or alkenyl oligoglucosides, fatty acid N-alkyl poly Hydroxyalkylamide, Alkylamidobetaine and / or protein hydrolysates or their condensates with fat acids on an animal or preferably vegetable basis. Particularly preferred are kos metic agents containing the cationized wheat or pea protein surfactants together with alkyl oligoglucosides and / or fatty acid N-methylglucamiden included. The mixing ratio can there at 10:90 to 90:10, preferably 25:75 to 75:25 and especially 40:60 to 60:40. Furthermore, it is of course possible, the cationized vegetable Pro invention tain surfactants with other known cationic surfactants, for example, typical quaternary Ammonium salts such as dimethyldistearylammonium chloride or benzyltrimethylammonium chloride and quaternized fatty acid triethanolammonium salts ("esterquats") and known esterquat / fat mix alcohol compounds.
Hautpflegemittel, wie Cremes, Lotionen und dergleichen, weisen in der Regel - neben den bereits genannten Tensiden - einen Gehalt an Ölkörpern, Emulgatoren, Fetten und Wachsen, Stabilisatoren sowie ebenfalls Überfettungsmitteln, Verdickungsmitteln, biogenen Wirkstoffen, Filmbildnern, Konser vierungsmitteln, Farb- und Duftstoffen auf. Haarpflegemittel, wie beispielsweise Haarshampoos, Haar lotionen, Schaumbäder und dergleichen, können als weitere Hilfs- und Zusatzstoffe - neben den bereits genannten Tensiden - Emulgatoren, Überfettungsmittel, Verdickungsmittel, biogene Wirkstoffe, Film bildner, Konservierungsmittel, Farb- und Duftstoffe enthalten.Skin care products, such as creams, lotions and the like, usually have - in addition to those already surfactants - a content of oil bodies, emulsifiers, fats and waxes, stabilizers as well as superfatting agents, thickeners, biogenic agents, film formers, Konser vierungsmitteln, dyes and fragrances. Hair care products, such as hair shampoos, hair Lotions, bubble baths and the like, as other auxiliaries and additives - in addition to the already surfactants mentioned - emulsifiers, superfatting agents, thickeners, biogenic agents, film artists, preservatives, dyes and fragrances.
Als Ölkörper kommen beispielsweise Guerbetalkohole auf Basis von Fettalkoholen mit 6 bis 18, vor zugsweise 8 bis 10 Kohlenstoffatomen, Ester von linearen C₆-C₂₀-Fettsäuren mit linearen C₆- C₂₀-Fett alkoholen, Ester von verzweigten C₆-C₁₃-Carbonsäuren mit linearen C₁₆-C₁₈-Fettalkoholen, Ester von linearen C₁₀-C₁₈-Fettsäuren mit verzweigten Alkoholen, insbesondere 2-Ethylhexanol, Ester von linea ren und/oder verzweigten Fettsäuren mit zweiwertigen Alkoholen und/oder Guerbetalkoholen, Triglyce ride auf Basis C₆-C₁₀-Fettsäuren, pflanzliche Öle, verzweigte primäre Alkohole, substituierte Cyclo hexane, Guerbetcarbonate und/oder Dialkylether in Betracht. Als Emulgatoren kommen sowohl be kannte W/O- als auch O/W-Emulgatoren wie beispielsweise gehärtetes und ethoxyliertes Ricinusöl, Polyglycerinfettsäureester oder Polyglycerinpolyricinoleate in Frage. Typische Beispiele für Fette sind Glyceride, als Wachse kommen u. a. Bienenwachs, Paraffinwachs oder Mikrowachse gegebenenfalls in Kombination mit hydrophilen Wachsen, z. B. Cetylstearylalkohol in Frage. Als Stabilisatoren können Metallsalze von Fettsäuren wie z. B. Magnesium-, Aluminium- und/oder Zinkstearat eingesetzt werden. Als Überfettungsmittel können Substanzen wie beispielsweise polyethoxylierte Lanolinderivate, Leci thinderivate, Polyolfettsäureester, Monoglyceride und Fettsäurealkanolamide verwendet werden, wobei die letzteren gleichzeitig als Schaumstabilisatoren dienen. Geeignete Verdickungsmittel sind bei spielsweise Polysaccharide, insbesondere Xanthan-Gum, Guar-Guar, Agar-Agar, Alginate und Tylosen, Carboxymethylcellulose und Hydroxyethylcellulose, ferner höhermolekulare Polyethylenglycolmono- und -diester von Fettsäuren, Polyacrylate, Polyvinylalkohol und Polyvinylpyrrolidon, Tenside wie bei spielsweise Fettalkoholethoxylate mit eingeengter Homologenverteilung oder Alkyloligoglucoside sowie Elektrolyte wie Kochsalz und Ammoniumchlorid. Unter biogenen Wirkstoffen sind beispielsweise Pflanzenextrakte und Vitaminkomplexe zu verstehen. Gebräuchliche Filmbildner sind beispielsweise Chitosan, mikrokristallines Chitosan, quaterniertes Chitosan, Polyvinylpyrrolidon, Vinylpyrrolidon-Vinyl acetat-Copolymerisate, Polymere der Acrylsäurereihe, quaternäre Cellulose-Derivate, Kollagen, Hya luronsäure bzw. deren Salze und ähnliche Verbindungen. Als Konservierungsmittel eignen sich beispielsweise Phenoxyethanol, Formaldehydlösung, Parabene, Pentandiol oder Sorbinsäure. Als Perl glanzmittel kommen beispielsweise Glycoldistearinsäureester wie Ethylenglycoldistearat, aber auch Fettsäuremonoglycolester in Betracht. Als Farbstoffe können die für kosmetische Zwecke geeigneten und zugelassenen Substanzen verwendet werden, wie sie beispielsweise in der Publikation "Kosme tische Färbemittel" der Farbstoffkommission der Deutschen Forschungsgemeinschaft, veröf fentlicht im Verlag Chemie, Weinheim, 1984, S. 81-106 zusammengestellt sind. Diese Farbstoffe werden üblicherweise in Konzentrationen von 0,001 bis 0,1 Gew.-%, bezogen auf die gesamte Mi schung, eingesetzt. Der Gesamtanteil der Hilfs- und Zusatzstoffe kann 1 bis 50, vorzugsweise 5 bis 40 Gew.-% und der nicht wäßrige Anteil ("Aktivsubstanzgehalt") 20 bis 80, vorzugsweise 30 bis 70 Gew.-% - bezogen auf die Mittel - betragen. Die Herstellung der Mittel kann in an sich bekannter Weise, d. h. beispielsweise durch Heiß-, Kalt-, Heiß-Heiß/Kalt- bzw. PIT-Emulgierung erfolgen. Hierbei handelt es sich um ein rein mechanisches Verfahren, eine chemische Reaktion findet nicht statt. Guerbet alcohols based on fatty alcohols with 6 to 18, for example, are used as the oil body preferably 8 to 10 carbon atoms, esters of linear C₆-C₂₀ fatty acids with linear C₆- C₂₀-fat alcohols, esters of branched C₆-C₁₃ carboxylic acids with linear C₁₆-C₁₈ fatty alcohols, esters of linear C₁₀-C₁₈ fatty acids with branched alcohols, in particular 2-ethylhexanol, esters of linea ren and / or branched fatty acids with dihydric alcohols and / or Guerbet alcohols, triglyce Ride based on C₆-C₁₀ fatty acids, vegetable oils, branched primary alcohols, substituted cyclo Hexanes, Guerbetcarbonate and / or dialkyl ethers into consideration. As emulsifiers come both be knew W / O and O / W emulsifiers such as, for example, hydrogenated and ethoxylated castor oil, Polyglycerin fatty acid esters or Polyglycerinpolyricinoleates in question. Typical examples of fats are Glycerides, as waxes come u. a. Beeswax, paraffin wax or microwaxes optionally in Combination with hydrophilic waxes, e.g. As cetylstearyl alcohol in question. As stabilizers can Metal salts of fatty acids such. As magnesium, aluminum and / or zinc stearate. As superfatting agents, substances such as polyethoxylated lanolin derivatives, Leci thinderivatives, polyol fatty acid esters, monoglycerides and fatty acid alkanolamides, wherein the latter simultaneously serve as foam stabilizers. Suitable thickening agents are included For example, polysaccharides, especially xanthan gum, guar guar, agar-agar, alginates and tyloses, Carboxymethyl cellulose and hydroxyethyl cellulose, and also higher molecular weight polyethylene glycol mono- and diesters of fatty acids, polyacrylates, polyvinyl alcohol and polyvinylpyrrolidone, surfactants as in For example, fatty alcohol ethoxylates with narrow homolog distribution or Alkyloligoglucoside and Electrolytes such as table salt and ammonium chloride. Among biogenic agents are, for example Plant extracts and vitamin complexes to understand. Common film makers are for example Chitosan, microcrystalline chitosan, quaternized chitosan, polyvinyl pyrrolidone, vinyl pyrrolidone vinyl acetate copolymers, polymers of the acrylic acid series, quaternary cellulose derivatives, collagen, Hya Luronic acid or its salts and similar compounds. As preservatives are suitable for example, phenoxyethanol, formaldehyde solution, parabens, pentanediol or sorbic acid. As Perl gloss agents include, for example, glycol distearic acid esters such as ethylene glycol distearate, but also Fatty acid monoglycol esters. As dyes, those suitable for cosmetic purposes and approved substances such as those described in the publication "Kosme Tische Färbemittel "of the Dye Commission of the Deutsche Forschungsgemeinschaft, publ fentlicht compiled by Verlag Chemie, Weinheim, 1984, pp. 81-106. These dyes are usually in concentrations of 0.001 to 0.1 wt .-%, based on the total Mi used. The total proportion of auxiliaries and additives may be 1 to 50, preferably 5 to 40 Wt .-% and the non-aqueous portion ("active substance content") 20 to 80, preferably 30 to 70 wt .-% - in terms of resources - amount. The preparation of the agent can in a conventional manner, d. H. for example, by hot, cold, hot-hot / cold or PIT emulsification. This is it it is a purely mechanical process, a chemical reaction does not take place.
Herstellung von kationisiertem Weizenproteinhydrolysat. In einem 1-m³-Rührkessel mit Rückfluß kühler wurden 390 kg erfindungsgemäß hergestelltes Weizenproteinhydrolysat vorgelegt, auf 60°C erhitzt und mit 20 Gew.-%iger Natriumhydroxidlösung auf einen pH-Wert von 10 eingestellt. Innerhalb 1 h wurden 178 kg N,N-Dimethyl-N-dodecyl-N-(2-hydroxy-3-chloro-n-propyl)-ammoniumchlor-id zudosiert. Die Reaktionsmischung wurde 4 h bei 55°C gerührt, auf Raumtemperatur abgekühlt und weitere 12 h gerührt. Schließlich wurde der Ansatz durch Zugabe von 32 Gew.-%iger Salzsäure auf einen pHB-Wert von 6,5 eingestellt und mit pHB-Methyl/Ethylester konserviert. Preparation of cationized wheat protein hydrolyzate. In a 1 m³ stirred tank with reflux 390 kg of wheat protein hydrolyzate produced according to the invention were initially charged to a cooler temperature of 60 ° C. heated and adjusted to a pH of 10 with 20 wt .-% sodium hydroxide solution. Within 1 178 kg of N, N-dimethyl-N-dodecyl-N- (2-hydroxy-3-chloro-n-propyl) -ammoniumchlor-id were metered. The reaction mixture was stirred for 4 h at 55 ° C, cooled to room temperature and a further 12 h touched. Finally, the batch was adjusted to a pHB by addition of 32% by weight hydrochloric acid of 6.5 and preserved with pHB methyl / ethyl ester.
Die dermatologische Verträglichkeit kationisierter Proteintenside pflanzlicher bzw. tierischer Herkunft wurde durch Untersuchungen an der Chorionallantoismembran des bebrüteten Hühnereis (HET-CAM) beurteilt. Bei diesem Test, der ein Modell für die Augenschleimhautverträglichkeit einer Substanz darstellt, wird die Cytotoxizität bestimmt. Zur Durchführung vgl. F.Bartnik et. al. in Seifen-Öle-Fette- Wachse, 114, 41 (1988). Die Messungen wurden gegen einen Standard (C12/18-Kokosfettalkohol+8EO- ethersulfat-Na/Mg-Salz) in 5 Gew.-%iger wäßriger Lösung durchgeführt. Die Ergebnisse sind in Tabelle 1 zusammengefaßt (Prozentangaben als Gew.-%)The dermatological compatibility of cationized protein surfactants of plant or animal origin was assessed by studies on the chorionallantoic membrane of the incubated chicken egg (HET-CAM). In this test, which is a model for the ocular mucosa compatibility of a substance, the cytotoxicity is determined. For the implementation cf. F. Bartnik et. al. in soap oils-fats-waxes, 114, 41 (1988). The measurements were carried out against a standard (C 12/18 coconut fatty alcohol + 8EO-ether sulfate Na / Mg salt) in 5% by weight aqueous solution. The results are summarized in Table 1 (percentages as wt .-%)
Das Beispiel und die Vergleichsversuche zeigen, daß die erfindungsgemäß hergestellten kationisierten Weizenproteinhydrolysate sowohl gegenüber Vergleichsprodukten auf Basis von tierischem Kollagen als auch anderer Pflanzenproteinhydrolysate eine verbesserte dermatologische Verträglichkeit be sitzen. Beispielrezepturen finden sich nachfolgend. Die Zusammensetzung ist gemäß INCl- Nomenklatur, angegeben alle Angaben verstehen sich als Gew.-%, Wasser und Konservierungsmittel ad 100.The example and the comparative experiments show that the cationized wheat protein hydrolysates prepared in accordance with the invention have an advantage over both animal collagen based comparison products as well as other vegetable protein hydrolysates improved dermatological compatibility be sit. Example formulations can be found below. The composition is according to INCl Nomenclature, all figures are by weight, water and preservative ad 100.
Claims (8)
- (a) zunächst bei einem pH-Wert im Bereich von 8 bis 10 mit Proteinasen und dann
- (b) bei einem pH-Wert im Bereich von 6 bis 7 mit Peptidasen hydrolysiert, und schließlich
- (c) das erhaltene Hydrolysat mit quartären Ammoniumsalzen umsetzt.
- (a) first at a pH in the range of 8 to 10 with proteinases and then
- (b) hydrolyzed at a pH in the range of 6 to 7 with peptidases, and finally
- (c) reacting the resulting hydrolyzate with quaternary ammonium salts.
- (a) zunächst bei einem pH-Wert im Bereich von 8 bis 10 mit Proteinasen und dann
- (b) bei einem pH-Wert im Bereich von 6 bis 7 mit Peptidasen hydrolysiert, und schließlich
- (c) das erhaltene Hydrolysat mit quartären Ammoniumsalzen umsetzt.
- (a) first at a pH in the range of 8 to 10 with proteinases and then
- (b) hydrolyzed at a pH in the range of 6 to 7 with peptidases, and finally
- (c) reacting the resulting hydrolyzate with quaternary ammonium salts.
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19505005A DE19505005C2 (en) | 1995-02-15 | 1995-02-15 | Cationized vegetable protein surfactants |
PCT/EP1996/000477 WO1996025141A1 (en) | 1995-02-15 | 1996-02-06 | Cationised vegetable protein tensides |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19505005A DE19505005C2 (en) | 1995-02-15 | 1995-02-15 | Cationized vegetable protein surfactants |
Publications (2)
Publication Number | Publication Date |
---|---|
DE19505005C1 DE19505005C1 (en) | 1996-04-04 |
DE19505005C2 true DE19505005C2 (en) | 1998-02-26 |
Family
ID=7753997
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE19505005A Expired - Lifetime DE19505005C2 (en) | 1995-02-15 | 1995-02-15 | Cationized vegetable protein surfactants |
Country Status (2)
Country | Link |
---|---|
DE (1) | DE19505005C2 (en) |
WO (1) | WO1996025141A1 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102004045186B4 (en) * | 2004-05-25 | 2011-08-18 | Engelhard Lyon S.A. | Liposomes which stimulate the intracellular penetration of active substances, their use for the preparation of topical pharmaceutical or cosmetic compositions containing these liposomes and a screening method for finding substances for stimulating intracellular penetration |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19631035C1 (en) * | 1996-08-01 | 1998-02-12 | Wella Ag | Hair coloring and tinting preparations |
DE19640831C2 (en) * | 1996-10-02 | 2002-11-21 | Kao Corp | Means for dyeing and tinting human hair |
EP0834303A3 (en) * | 1996-10-02 | 1998-08-19 | Kao Corporation | Composition for coloring of human hair |
DE19640792C1 (en) * | 1996-10-02 | 1998-03-05 | Kao Corp | Aqueous toning shampoo containing cationic plant protein hydrolysate |
FR2802418B1 (en) * | 1999-12-16 | 2002-02-15 | Silab Sa | PROCESS FOR OBTAINING A TENSIONING ACTIVE INGREDIENT FOR FIGHTING AGING OF THE SKIN, TENSIONER OBTAINED AND COMPOSITION USING SUCH TENSIONER |
DE10042445A1 (en) * | 2000-08-29 | 2002-03-14 | Cognis Deutschland Gmbh | Use of quaternized protein hydrolyzates |
DE10154628A1 (en) * | 2001-09-25 | 2003-04-10 | Beiersdorf Ag | Surfactant(s) for use in cosmetic or dermatological cleaning, comprise alkyl glucosides |
DE10253217A1 (en) * | 2002-11-15 | 2004-05-27 | Cognis Deutschland Gmbh & Co. Kg | Use of quaternized protein hydrolyzates in washing and cleaning agents |
BE1016329A3 (en) * | 2004-11-22 | 2006-08-01 | Nannic Internat Bvba | Deodorant application method comprises spraying foam onto hand, applying foam to skin and rinsing foam off in shower |
CN103599730B (en) * | 2013-11-25 | 2015-08-19 | 齐齐哈尔大学 | A kind of quaternary cationics and preparation method thereof |
BR112019004023B1 (en) | 2016-09-13 | 2022-08-30 | Basf Se | PROTEIN HYDROLYSATE, METHOD FOR PREPARING PROTEIN HYDROLYSATE, USE OF PROTEIN HYDROLYSATE, AND, COSMETIC COMPOSITIONS |
ES2913151T3 (en) * | 2016-09-13 | 2022-05-31 | Basf Se | Low molecular weight keratin hydrolysates. |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS6368514A (en) * | 1986-09-09 | 1988-03-28 | Kurooda Japan Kk | Cosmetic containing vegetable polypeptide derivative |
JPH04139113A (en) * | 1990-09-27 | 1992-05-13 | Seiwa Kasei:Kk | Hair-treatment agent |
JPH04154713A (en) * | 1990-10-15 | 1992-05-27 | Seiwa Kasei:Kk | First agent for permanent wave |
JPH06345625A (en) * | 1993-06-14 | 1994-12-20 | Kao Corp | Hair nourishing and growing agent |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0109074A1 (en) * | 1982-11-16 | 1984-05-23 | Inolex Chemical Company | Quarternary ammonium derivatives of amino acid units |
US4793992A (en) * | 1987-03-25 | 1988-12-27 | Redken Laboratories, Inc. | Hair treatment composition |
JPH0548728A (en) * | 1991-08-08 | 1993-02-26 | Fujitsu Ltd | Exchange processing system |
JPH06345626A (en) * | 1993-06-04 | 1994-12-20 | Kurooda Japan Kk | Hair cleaning agent |
-
1995
- 1995-02-15 DE DE19505005A patent/DE19505005C2/en not_active Expired - Lifetime
-
1996
- 1996-02-06 WO PCT/EP1996/000477 patent/WO1996025141A1/en active Application Filing
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS6368514A (en) * | 1986-09-09 | 1988-03-28 | Kurooda Japan Kk | Cosmetic containing vegetable polypeptide derivative |
JPH04139113A (en) * | 1990-09-27 | 1992-05-13 | Seiwa Kasei:Kk | Hair-treatment agent |
JPH04154713A (en) * | 1990-10-15 | 1992-05-27 | Seiwa Kasei:Kk | First agent for permanent wave |
JPH06345625A (en) * | 1993-06-14 | 1994-12-20 | Kao Corp | Hair nourishing and growing agent |
Non-Patent Citations (4)
Title |
---|
FIEDLER: Lexikon der Hilfsstoffe für Pharmazie, Kosmetik und angrenzende Gebiete, 3. Auflage 1989,S. 1023 * |
Firmenschrift: "Cosmetic Ingredients and Ideas" "Plant Proteins" der Brooks Industries Inc., Data VEGP/Issue 3, 1994 * |
Firmenschrift: "Cosmetic Ingredients and Ideas" der Brooks Industries Inc., Issue #14, März 1994 * |
Firmenschrift: "Hydrotriticum" der Firma Croda, Mai 1991 * |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102004045186B4 (en) * | 2004-05-25 | 2011-08-18 | Engelhard Lyon S.A. | Liposomes which stimulate the intracellular penetration of active substances, their use for the preparation of topical pharmaceutical or cosmetic compositions containing these liposomes and a screening method for finding substances for stimulating intracellular penetration |
DE102004045186B9 (en) * | 2004-05-25 | 2012-02-16 | Engelhard Lyon S.A. | Liposomes that stimulate the intracellular penetration of drugs, their use for the preparation of topical pharmaceutical or cosmetic compositions containing these liposomes and a screening method for finding substances to stimulate intracellular penetration |
Also Published As
Publication number | Publication date |
---|---|
DE19505005C1 (en) | 1996-04-04 |
WO1996025141A1 (en) | 1996-08-22 |
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D1 | Grant (no unexamined application published) patent law 81 | ||
8363 | Opposition against the patent | ||
8366 | Restricted maintained after opposition proceedings | ||
8305 | Restricted maintenance of patent after opposition | ||
D3 | Patent maintained restricted (no unexamined application published) | ||
8327 | Change in the person/name/address of the patent owner |
Owner name: COGNIS DEUTSCHLAND GMBH, 40589 DUESSELDORF, DE |
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8327 | Change in the person/name/address of the patent owner |
Owner name: COGNIS DEUTSCHLAND GMBH & CO. KG, 40589 DUESSELDOR |
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8327 | Change in the person/name/address of the patent owner |
Owner name: COGNIS IP MANAGEMENT GMBH, 40589 DUESSELDORF, DE |
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R071 | Expiry of right | ||
R071 | Expiry of right |