CA1236639A - Polymeres d'alcool vinylique renfermant des groupes d'azote quaternaire, pour le conditionnement de la peau, comme cosmetique, et dans des formulations pharmaceutiques - Google Patents

Polymeres d'alcool vinylique renfermant des groupes d'azote quaternaire, pour le conditionnement de la peau, comme cosmetique, et dans des formulations pharmaceutiques

Info

Publication number: CA1236639A
Authority: CA; Canada
Prior art keywords: composition; polyvinyl alcohol; weight; aqueous; molecular weight
Prior art date: 1983-10-07
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

Application number

CA000463380A

Other languages

English (en)

Inventor

Ronald I. Davis

George R. Titus

Charalambos J. Phalangas

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Zeneca Inc

Original Assignee

ICI Americas Inc

Priority date (The priority date 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 date listed.)

1983-10-07

Filing date

1984-09-17

Publication date

1988-05-10

1984-09-17 Application filed by ICI Americas Inc filed Critical ICI Americas Inc

1988-05-10 Application granted granted Critical

1988-05-10 Publication of CA1236639A publication Critical patent/CA1236639A/fr

Status Expired legal-status Critical Current

Links

229920002451 polyvinyl alcohol Polymers 0.000 title claims abstract description 60
239000002537 cosmetic Substances 0.000 title claims abstract description 11
230000003750 conditioning effect Effects 0.000 title claims abstract description 8
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 title claims abstract description 7
239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 52
239000000203 mixture Substances 0.000 claims description 50
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 44
239000004372 Polyvinyl alcohol Substances 0.000 claims description 44
239000000243 solution Substances 0.000 claims description 40
-1 alkylsulfate ion Chemical class 0.000 claims description 35
229920000642 polymer Polymers 0.000 claims description 35
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 30
229910052757 nitrogen Inorganic materials 0.000 claims description 27
239000007864 aqueous solution Substances 0.000 claims description 18
238000000034 method Methods 0.000 claims description 18
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
238000006243 chemical reaction Methods 0.000 claims description 12
239000003995 emulsifying agent Substances 0.000 claims description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 10
230000003197 catalytic effect Effects 0.000 claims description 10
238000001556 precipitation Methods 0.000 claims description 10
239000006185 dispersion Substances 0.000 claims description 9
125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 claims description 8
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
239000002253 acid Substances 0.000 claims description 7
125000004432 carbon atom Chemical group C* 0.000 claims description 7
150000004820 halides Chemical class 0.000 claims description 7
239000011541 reaction mixture Substances 0.000 claims description 7
238000000502 dialysis Methods 0.000 claims description 6
PUVAFTRIIUSGLK-UHFFFAOYSA-M trimethyl(oxiran-2-ylmethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1CO1 PUVAFTRIIUSGLK-UHFFFAOYSA-M 0.000 claims description 6
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 6
239000003974 emollient agent Substances 0.000 claims description 5
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
239000001301 oxygen Substances 0.000 claims description 4
229910052760 oxygen Inorganic materials 0.000 claims description 4
150000001450 anions Chemical class 0.000 claims description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
229940071125 manganese acetate Drugs 0.000 claims description 3
UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 claims description 3
230000008569 process Effects 0.000 claims description 3
229920002689 polyvinyl acetate Polymers 0.000 claims description 2
239000011118 polyvinyl acetate Substances 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims 2
125000002947 alkylene group Chemical group 0.000 claims 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
229920001577 copolymer Polymers 0.000 claims 1
125000005208 trialkylammonium group Chemical group 0.000 claims 1
238000000108 ultra-filtration Methods 0.000 claims 1
239000006210 lotion Substances 0.000 abstract description 17
230000004888 barrier function Effects 0.000 abstract description 16
239000002674 ointment Substances 0.000 abstract description 5
238000011282 treatment Methods 0.000 abstract description 4
125000002091 cationic group Chemical group 0.000 abstract description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 47
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
239000000047 product Substances 0.000 description 21
238000002360 preparation method Methods 0.000 description 20
210000003491 skin Anatomy 0.000 description 19
239000002585 base Substances 0.000 description 15
239000010408 film Substances 0.000 description 14
238000012360 testing method Methods 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
238000009472 formulation Methods 0.000 description 11
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
239000003921 oil Substances 0.000 description 9
229920003171 Poly (ethylene oxide) Polymers 0.000 description 8
235000014113 dietary fatty acids Nutrition 0.000 description 8
238000001035 drying Methods 0.000 description 8
239000000194 fatty acid Substances 0.000 description 8
229930195729 fatty acid Natural products 0.000 description 8
150000004665 fatty acids Chemical class 0.000 description 8
238000001914 filtration Methods 0.000 description 8
239000012071 phase Substances 0.000 description 8
239000006071 cream Substances 0.000 description 7
150000002148 esters Chemical class 0.000 description 7
239000012153 distilled water Substances 0.000 description 6
239000002244 precipitate Substances 0.000 description 6
239000007787 solid Substances 0.000 description 6
229920000180 alkyd Polymers 0.000 description 5
239000000463 material Substances 0.000 description 5
239000000843 powder Substances 0.000 description 5
239000002002 slurry Substances 0.000 description 5
239000000344 soap Substances 0.000 description 5
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
241001465754 Metazoa Species 0.000 description 4
239000004615 ingredient Substances 0.000 description 4
239000012528 membrane Substances 0.000 description 4
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 4
238000003756 stirring Methods 0.000 description 4
125000001424 substituent group Chemical group 0.000 description 4
HBXWUCXDUUJDRB-UHFFFAOYSA-N 1-octadecoxyoctadecane Chemical compound CCCCCCCCCCCCCCCCCCOCCCCCCCCCCCCCCCCCC HBXWUCXDUUJDRB-UHFFFAOYSA-N 0.000 description 3
239000004166 Lanolin Substances 0.000 description 3
229910019142 PO4 Inorganic materials 0.000 description 3
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical class OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
239000000839 emulsion Substances 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
239000012467 final product Substances 0.000 description 3
239000000118 hair dye Substances 0.000 description 3
235000019388 lanolin Nutrition 0.000 description 3
229940039717 lanolin Drugs 0.000 description 3
239000007788 liquid Substances 0.000 description 3
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 description 3
235000019271 petrolatum Nutrition 0.000 description 3
235000021317 phosphate Nutrition 0.000 description 3
125000001453 quaternary ammonium group Chemical group 0.000 description 3
238000011084 recovery Methods 0.000 description 3
230000009467 reduction Effects 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
239000012265 solid product Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
239000010409 thin film Substances 0.000 description 3
229920002554 vinyl polymer Polymers 0.000 description 3
KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
206010019049 Hair texture abnormal Diseases 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
229930006000 Sucrose Natural products 0.000 description 2
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
235000018936 Vitellaria paradoxa Nutrition 0.000 description 2
239000005862 Whey Substances 0.000 description 2
102000007544 Whey Proteins Human genes 0.000 description 2
108010046377 Whey Proteins Proteins 0.000 description 2
XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
239000000443 aerosol Substances 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
229910052782 aluminium Inorganic materials 0.000 description 2
230000001166 anti-perspirative effect Effects 0.000 description 2
239000003213 antiperspirant Substances 0.000 description 2
239000003125 aqueous solvent Substances 0.000 description 2
230000005540 biological transmission Effects 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
230000000694 effects Effects 0.000 description 2
150000002191 fatty alcohols Chemical class 0.000 description 2
239000007789 gas Substances 0.000 description 2
IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
238000000338 in vitro Methods 0.000 description 2
239000002480 mineral oil Substances 0.000 description 2
235000010446 mineral oil Nutrition 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Chemical compound [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 2
239000002304 perfume Substances 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
239000010452 phosphate Substances 0.000 description 2
239000000049 pigment Substances 0.000 description 2
239000003755 preservative agent Substances 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
230000003068 static effect Effects 0.000 description 2
210000000434 stratum corneum Anatomy 0.000 description 2
239000000126 substance Substances 0.000 description 2
239000005720 sucrose Substances 0.000 description 2
HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 2
239000002562 thickening agent Substances 0.000 description 2
239000001993 wax Substances 0.000 description 2
239000011787 zinc oxide Substances 0.000 description 2
235000014692 zinc oxide Nutrition 0.000 description 2
CPYIZQLXMGRKSW-UHFFFAOYSA-N zinc;iron(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[Fe+3].[Fe+3].[Zn+2] CPYIZQLXMGRKSW-UHFFFAOYSA-N 0.000 description 2
XINQFOMFQFGGCQ-UHFFFAOYSA-L (2-dodecoxy-2-oxoethyl)-[6-[(2-dodecoxy-2-oxoethyl)-dimethylazaniumyl]hexyl]-dimethylazanium;dichloride Chemical compound [Cl-].[Cl-].CCCCCCCCCCCCOC(=O)C[N+](C)(C)CCCCCC[N+](C)(C)CC(=O)OCCCCCCCCCCCC XINQFOMFQFGGCQ-UHFFFAOYSA-L 0.000 description 1
XPPODKQKBFSUCU-UHFFFAOYSA-M (3-chloro-3-hydroxypropyl)-trimethylazanium;chloride Chemical compound [Cl-].C[N+](C)(C)CCC(O)Cl XPPODKQKBFSUCU-UHFFFAOYSA-M 0.000 description 1
QBUKAFSEUHGMMX-MTJSOVHGSA-N (5z)-5-[[3-(1-hydroxyethyl)thiophen-2-yl]methylidene]-10-methoxy-2,2,4-trimethyl-1h-chromeno[3,4-f]quinolin-9-ol Chemical compound C1=CC=2NC(C)(C)C=C(C)C=2C2=C1C=1C(OC)=C(O)C=CC=1O\C2=C/C=1SC=CC=1C(C)O QBUKAFSEUHGMMX-MTJSOVHGSA-N 0.000 description 1
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
KZEVSDGEBAJOTK-UHFFFAOYSA-N 1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-2-[5-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]-1,3,4-oxadiazol-2-yl]ethanone Chemical compound N1N=NC=2CN(CCC=21)C(CC=1OC(=NN=1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)=O KZEVSDGEBAJOTK-UHFFFAOYSA-N 0.000 description 1
IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
OFQCQIGMURIECL-UHFFFAOYSA-N 2-[2-(diethylamino)ethyl]-2',6'-dimethylspiro[isoquinoline-4,4'-oxane]-1,3-dione;phosphoric acid Chemical compound OP(O)(O)=O.O=C1N(CCN(CC)CC)C(=O)C2=CC=CC=C2C21CC(C)OC(C)C2 OFQCQIGMURIECL-UHFFFAOYSA-N 0.000 description 1
LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
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229940018563 3-aminophenol Drugs 0.000 description 1
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240000002132 Beaucarnea recurvata Species 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
241001315286 Damon Species 0.000 description 1
SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
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DCTZSBXXVOFRIL-UHFFFAOYSA-M benzyl-(2-ethoxy-2-oxoethyl)-dimethylazanium;chloride Chemical compound [Cl-].CCOC(=O)C[N+](C)(C)CC1=CC=CC=C1 DCTZSBXXVOFRIL-UHFFFAOYSA-M 0.000 description 1
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DTPCFIHYWYONMD-UHFFFAOYSA-N decaethylene glycol Polymers OCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO DTPCFIHYWYONMD-UHFFFAOYSA-N 0.000 description 1
125000003074 decanoyl 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(*)=O 0.000 description 1
230000002939 deleterious effect Effects 0.000 description 1
GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
229960004132 diethyl ether Drugs 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
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 description 1
239000000975 dye Substances 0.000 description 1
238000004043 dyeing Methods 0.000 description 1
GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
150000002195 fatty ethers Chemical class 0.000 description 1
238000009501 film coating Methods 0.000 description 1
239000003205 fragrance Substances 0.000 description 1
239000000499 gel Substances 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
238000000227 grinding Methods 0.000 description 1
230000003648 hair appearance Effects 0.000 description 1
150000003944 halohydrins Chemical group 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229910052864 hemimorphite Inorganic materials 0.000 description 1
239000003906 humectant Substances 0.000 description 1
UTSOXZIZVGUTCF-UHFFFAOYSA-N hydrate;hydroiodide Chemical compound O.I UTSOXZIZVGUTCF-UHFFFAOYSA-N 0.000 description 1
150000004677 hydrates Chemical class 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
229920001477 hydrophilic polymer Polymers 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
230000006872 improvement Effects 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
239000002085 irritant Substances 0.000 description 1
231100000021 irritant Toxicity 0.000 description 1
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
XUGNVMKQXJXZCD-UHFFFAOYSA-N isopropyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC(C)C XUGNVMKQXJXZCD-UHFFFAOYSA-N 0.000 description 1
229940075495 isopropyl palmitate Drugs 0.000 description 1
239000000787 lecithin Substances 0.000 description 1
235000010445 lecithin Nutrition 0.000 description 1
229940067606 lecithin Drugs 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
239000011159 matrix material Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
125000005395 methacrylic acid group Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
229940105132 myristate Drugs 0.000 description 1
229940043348 myristyl alcohol Drugs 0.000 description 1
WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
125000000016 octadecenoyl group Chemical group O=C([*])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])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
125000005064 octadecenyl group Chemical group C(=CCCCCCCCCCCCCCCCC)* 0.000 description 1
239000003883 ointment base Substances 0.000 description 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
150000002924 oxiranes Chemical class 0.000 description 1
125000000466 oxiranyl group Chemical group 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
239000012188 paraffin wax Substances 0.000 description 1
235000019809 paraffin wax Nutrition 0.000 description 1
230000008775 paternal effect Effects 0.000 description 1
229940066842 petrolatum Drugs 0.000 description 1
150000003904 phospholipids Chemical class 0.000 description 1
229920001281 polyalkylene Polymers 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
229920006254 polymer film Polymers 0.000 description 1
229920001184 polypeptide Polymers 0.000 description 1
229920000136 polysorbate Polymers 0.000 description 1
102000004196 processed proteins & peptides Human genes 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
238000000746 purification Methods 0.000 description 1
150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
229960000948 quinine Drugs 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011347 resin Substances 0.000 description 1
GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 1
229960001755 resorcinol Drugs 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000003352 sequestering agent Substances 0.000 description 1
230000037394 skin elasticity Effects 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
235000010199 sorbic acid Nutrition 0.000 description 1
229940075582 sorbic acid Drugs 0.000 description 1
239000004334 sorbic acid Substances 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
241000894007 species Species 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
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 description 1
230000000475 sunscreen effect Effects 0.000 description 1
239000000516 sunscreening agent Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
TUNFSRHWOTWDNC-UHFFFAOYSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 1
239000001585 thymus vulgaris Substances 0.000 description 1
238000005809 transesterification reaction Methods 0.000 description 1
229910052723 transition metal Inorganic materials 0.000 description 1
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 description 1
JMMAMAWBEJRFQN-UHFFFAOYSA-M trimethyl(oxiran-2-ylmethyl)azanium;bromide Chemical compound [Br-].C[N+](C)(C)CC1CO1 JMMAMAWBEJRFQN-UHFFFAOYSA-M 0.000 description 1
229910052721 tungsten Inorganic materials 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
238000005303 weighing Methods 0.000 description 1
230000004580 weight loss Effects 0.000 description 1

Landscapes

Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Medicinal Preparation (AREA)
Cosmetics (AREA)

CA000463380A 1983-10-07 1984-09-17 Polymeres d'alcool vinylique renfermant des groupes d'azote quaternaire, pour le conditionnement de la peau, comme cosmetique, et dans des formulations pharmaceutiques Expired CA1236639A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US54004183A	1983-10-07	1983-10-07
US06/540,041		1983-10-07

Publications (1)

Publication Number	Publication Date
CA1236639A true CA1236639A (fr)	1988-05-10

Family

ID=24153730

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000463380A Expired CA1236639A (fr)	1983-10-07	1984-09-17	Polymeres d'alcool vinylique renfermant des groupes d'azote quaternaire, pour le conditionnement de la peau, comme cosmetique, et dans des formulations pharmaceutiques

Country Status (5)

Country	Link
JP (1)	JPS60133008A (fr)
AU (1)	AU564745B2 (fr)
CA (1)	CA1236639A (fr)
MX (1)	MX202910A (fr)
NZ (1)	NZ209699A (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH0627205B2 (ja) *	1986-12-27	1994-04-13	日本合成化学工業株式会社	アルカリ性物質包装用のポリビニルアルコ−ルフイルム
WO2017024110A1 (fr) *	2015-08-04	2017-02-09	Isp Investments Llc	Polymères dérivés d'éthers d'alcool vinylique à fonction amino et leurs applications
WO2021002337A1 (fr) *	2019-07-03	2021-01-07	株式会社資生堂	Procédé cosmétique
CN114025851B (zh) *	2019-07-03	2024-08-16	株式会社资生堂	保湿用膜化妆料

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS523689A (en) *	1975-06-27	1977-01-12	Yotsukaichi Gosei Kk	Process for preparing cationic high polymers
JPS5811046A (ja) *	1981-07-13	1983-01-21	Mitsubishi Chem Ind Ltd	多孔質陰イオン交換樹脂およびその製法

1984
- 1984-09-17 CA CA000463380A patent/CA1236639A/fr not_active Expired
- 1984-09-25 AU AU33479/84A patent/AU564745B2/en not_active Ceased
- 1984-09-27 NZ NZ20969984A patent/NZ209699A/en unknown
- 1984-10-01 MX MX20291084A patent/MX202910A/es unknown
- 1984-10-08 JP JP21120584A patent/JPS60133008A/ja active Pending

Also Published As

Publication number	Publication date
MX202910A (es)	1994-02-28
NZ209699A (en)	1987-11-27
AU564745B2 (en)	1987-08-27
AU3347984A (en)	1985-04-18
JPS60133008A (ja)	1985-07-16

Legal Events

Date	Code	Title	Description
2005-05-10	MKEX	Expiry

Publication	Publication Date	Title
US4690817A (en)	1987-09-01	Quaternary nitrogen containing polyvinyl alcohol polymers for use in skin conditioning, cosmetic and pharmaceutical formulations
US4645794A (en)	1987-02-24	Quaternary nitrogen containing polyvinyl alcohol polymers for use in skin conditioning, cosmetic and pharmaceutical formulations
US4921949A (en)	1990-05-01	Process for making quaternary chitosan derivatives for cosmetic agents
US4411891A (en)	1983-10-25	Cationized dextran and salts thereof and manufacturing process and utilization thereof
US5384334A (en)	1995-01-24	Alkoxylated alkyl glucoside ether quaternaries useful in personal care
US4976952A (en)	1990-12-11	Macromolecular, surface-active, quaternary, N-substituted chitosan derivatives as well as cosmetic composition based on these new chitosan derivatives
EP0570532B1 (fr)	1996-08-28	Composes quaternaires de panthenol et utilisation desdits composes
US4689217A (en)	1987-08-25	Amine and ammonium nitrogen containing polyvinyl alcohol polymers having improved lipophilic properties for use in skin conditioning, cosmetic and pharmaceutical formulations
US3766267A (en)	1973-10-16	Quaternary halides of gluconamides
EP1624851B1 (fr)	2014-05-28	Applications de soins capillaires faisant intervenir des emulsions contenant des silanes et des siloxanes elastomeres comportant des atomes d'azote
CA1276380C (fr)	1990-11-13	Utilisation de poly (n-acylaklylenimines) partiellement hydrolisees pour les soins d'hygiene personnelle
US4584196A (en)	1986-04-22	Perfluorinated surface-active oligomers and compositions for treating hair containing these oligomers
CA2664326C (fr)	2016-01-19	Ether de cellulose quaternise destine a des produits d'hygiene personnelle
US5196499A (en)	1993-03-23	Terminal silicone ester quaternary compounds
US5112886A (en)	1992-05-12	Allantoin salts of quaternary nitrogen containing polymers for use in skin conditioning, cosmetic and pharmaceutical formulations
JPS6360725B2 (fr)	1988-11-25
JPS598701A (ja)	1984-01-18	キトサン誘導体をベ−スとした理容剤、新規キトサン誘導体および該誘導体の製造法
US3855290A (en)	1974-12-17	Quaternary halides of gluconamides
US5280099A (en)	1994-01-18	Silicone taurine polymers
JPH0717786B2 (ja)	1995-03-01	グリコサミノグリカンとカチオン重合体との組成物
JPS6334851B2 (fr)	1988-07-12
US6010707A (en)	2000-01-04	Cosmetic and dermatological compositions containing aminoalcohol derivatives containing a urea functional group and uses thereof
US4243659A (en)	1981-01-06	Compositions for improving hair body and method of use
US4576967A (en)	1986-03-18	Novel polyol ether compounds, process preparing the compounds, and cosmetics comprising same
US5254335A (en)	1993-10-19	Hair conditioning compounds containing reactive nonionic surfactants and isothiuronium compounds and method of use