WO2005097834A2 - Liquid dispersion polymer compositions, their preparation and their use - Google Patents
Liquid dispersion polymer compositions, their preparation and their use Download PDFInfo
- Publication number
- WO2005097834A2 WO2005097834A2 PCT/EP2005/051429 EP2005051429W WO2005097834A2 WO 2005097834 A2 WO2005097834 A2 WO 2005097834A2 EP 2005051429 W EP2005051429 W EP 2005051429W WO 2005097834 A2 WO2005097834 A2 WO 2005097834A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- weight
- liquid dispersion
- water
- polymer
- aqueous
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 84
- 239000007788 liquid Substances 0.000 title claims abstract description 45
- 239000004815 dispersion polymer Substances 0.000 title claims abstract description 22
- 238000002360 preparation method Methods 0.000 title claims description 8
- 229920000642 polymer Polymers 0.000 claims abstract description 56
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 52
- 239000004094 surface-active agent Substances 0.000 claims abstract description 28
- 238000006386 neutralization reaction Methods 0.000 claims abstract description 27
- 239000008365 aqueous carrier Substances 0.000 claims abstract description 19
- 230000008719 thickening Effects 0.000 claims abstract description 17
- 239000012530 fluid Substances 0.000 claims abstract description 16
- 239000011859 microparticle Substances 0.000 claims abstract description 11
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000000178 monomer Substances 0.000 claims description 38
- 239000006071 cream Substances 0.000 claims description 30
- 239000006210 lotion Substances 0.000 claims description 21
- 125000000129 anionic group Chemical group 0.000 claims description 18
- 238000009472 formulation Methods 0.000 claims description 17
- 239000002245 particle Substances 0.000 claims description 15
- 239000006185 dispersion Substances 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 11
- 239000004615 ingredient Substances 0.000 claims description 10
- 238000006116 polymerization reaction Methods 0.000 claims description 9
- 239000002537 cosmetic Substances 0.000 claims description 7
- 239000002674 ointment Substances 0.000 claims description 7
- 239000000499 gel Substances 0.000 claims description 6
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- XHZPRMZZQOIPDS-UHFFFAOYSA-N 2-Methyl-2-[(1-oxo-2-propenyl)amino]-1-propanesulfonic acid Chemical compound OS(=O)(=O)CC(C)(C)NC(=O)C=C XHZPRMZZQOIPDS-UHFFFAOYSA-N 0.000 claims description 3
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- MNCGMVDMOKPCSQ-UHFFFAOYSA-M sodium;2-phenylethenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C=CC1=CC=CC=C1 MNCGMVDMOKPCSQ-UHFFFAOYSA-M 0.000 claims description 3
- 229940124597 therapeutic agent Drugs 0.000 claims description 3
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims description 2
- 239000013503 personal care ingredient Substances 0.000 claims description 2
- 229940124531 pharmaceutical excipient Drugs 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 3
- 239000012071 phase Substances 0.000 description 29
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 239000003921 oil Substances 0.000 description 15
- 238000003756 stirring Methods 0.000 description 13
- 235000019198 oils Nutrition 0.000 description 12
- 239000002562 thickening agent Substances 0.000 description 12
- 239000000839 emulsion Substances 0.000 description 11
- 230000002441 reversible effect Effects 0.000 description 10
- 239000003431 cross linking reagent Substances 0.000 description 9
- 239000007921 spray Substances 0.000 description 9
- 230000002209 hydrophobic effect Effects 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 239000002480 mineral oil Substances 0.000 description 7
- 235000010446 mineral oil Nutrition 0.000 description 7
- PRAKJMSDJKAYCZ-UHFFFAOYSA-N squalane Chemical compound CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 239000012190 activator Substances 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 239000003995 emulsifying agent Substances 0.000 description 6
- -1 ethylhexyl Chemical group 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 5
- 229940048053 acrylate Drugs 0.000 description 5
- 239000003974 emollient agent Substances 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 229920001477 hydrophilic polymer Polymers 0.000 description 5
- 210000004080 milk Anatomy 0.000 description 5
- 235000013336 milk Nutrition 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 229920002125 Sokalan® Polymers 0.000 description 4
- 238000002479 acid--base titration Methods 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000007720 emulsion polymerization reaction Methods 0.000 description 4
- 239000012051 hydrophobic carrier Substances 0.000 description 4
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 4
- 229920001296 polysiloxane Polymers 0.000 description 4
- 229940115476 ppg-1 trideceth-6 Drugs 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 239000000344 soap Substances 0.000 description 4
- CNPVJWYWYZMPDS-UHFFFAOYSA-N 2-methyldecane Chemical group CCCCCCCCC(C)C CNPVJWYWYZMPDS-UHFFFAOYSA-N 0.000 description 3
- 244000068988 Glycine max Species 0.000 description 3
- 235000010469 Glycine max Nutrition 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000013019 agitation Methods 0.000 description 3
- 150000003863 ammonium salts Chemical class 0.000 description 3
- 125000002091 cationic group Chemical group 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 230000002951 depilatory effect Effects 0.000 description 3
- 239000004205 dimethyl polysiloxane Substances 0.000 description 3
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 230000001815 facial effect Effects 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- JXTPJDDICSTXJX-UHFFFAOYSA-N n-Triacontane Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCC JXTPJDDICSTXJX-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 229920000058 polyacrylate Polymers 0.000 description 3
- MLGWTHRHHANFCC-UHFFFAOYSA-N prop-2-en-1-amine;hydrochloride Chemical compound Cl.NCC=C MLGWTHRHHANFCC-UHFFFAOYSA-N 0.000 description 3
- 241000894007 species Species 0.000 description 3
- 229940032094 squalane Drugs 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 239000000516 sunscreening agent Substances 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- XWJBRBSPAODJER-UHFFFAOYSA-N 1,7-octadiene Chemical compound C=CCCCCC=C XWJBRBSPAODJER-UHFFFAOYSA-N 0.000 description 2
- PQUXFUBNSYCQAL-UHFFFAOYSA-N 1-(2,3-difluorophenyl)ethanone Chemical compound CC(=O)C1=CC=CC(F)=C1F PQUXFUBNSYCQAL-UHFFFAOYSA-N 0.000 description 2
- LVKKFNORSNCNPP-UHFFFAOYSA-N 2,2-bis(prop-2-enoylamino)acetic acid Chemical compound C=CC(=O)NC(C(=O)O)NC(=O)C=C LVKKFNORSNCNPP-UHFFFAOYSA-N 0.000 description 2
- XIEWGQFCESQNBK-UHFFFAOYSA-N 2-hexanoyloxyethyl hexanoate Chemical compound CCCCCC(=O)OCCOC(=O)CCCCC XIEWGQFCESQNBK-UHFFFAOYSA-N 0.000 description 2
- BANXPJUEBPWEOT-UHFFFAOYSA-N 2-methyl-Pentadecane Chemical compound CCCCCCCCCCCCCC(C)C BANXPJUEBPWEOT-UHFFFAOYSA-N 0.000 description 2
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- XMSXQFUHVRWGNA-UHFFFAOYSA-N Decamethylcyclopentasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 XMSXQFUHVRWGNA-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- 244000062730 Melissa officinalis Species 0.000 description 2
- 235000010654 Melissa officinalis Nutrition 0.000 description 2
- 239000004909 Moisturizer Substances 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- POJWUDADGALRAB-UHFFFAOYSA-N allantoin Chemical compound NC(=O)NC1NC(=O)NC1=O POJWUDADGALRAB-UHFFFAOYSA-N 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229940071160 cocoate Drugs 0.000 description 2
- 230000003750 conditioning effect Effects 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 229940086555 cyclomethicone Drugs 0.000 description 2
- SASYSVUEVMOWPL-NXVVXOECSA-N decyl oleate Chemical compound CCCCCCCCCCOC(=O)CCCCCCC\C=C/CCCCCCCC SASYSVUEVMOWPL-NXVVXOECSA-N 0.000 description 2
- 229940008099 dimethicone Drugs 0.000 description 2
- 239000003792 electrolyte Substances 0.000 description 2
- 238000004945 emulsification Methods 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000000865 liniment Substances 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
- 239000008267 milk Substances 0.000 description 2
- 230000001333 moisturizer Effects 0.000 description 2
- 239000007764 o/w emulsion Substances 0.000 description 2
- 230000003204 osmotic effect Effects 0.000 description 2
- 239000003505 polymerization initiator Substances 0.000 description 2
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 210000004761 scalp Anatomy 0.000 description 2
- 239000002453 shampoo Substances 0.000 description 2
- 229940047670 sodium acrylate Drugs 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000000475 sunscreen effect Effects 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 230000008961 swelling Effects 0.000 description 2
- 230000000699 topical effect Effects 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 239000007762 w/o emulsion Substances 0.000 description 2
- WTVHAMTYZJGJLJ-UHFFFAOYSA-N (+)-(4S,8R)-8-epi-beta-bisabolol Natural products CC(C)=CCCC(C)C1(O)CCC(C)=CC1 WTVHAMTYZJGJLJ-UHFFFAOYSA-N 0.000 description 1
- RGZSQWQPBWRIAQ-CABCVRRESA-N (-)-alpha-Bisabolol Chemical compound CC(C)=CCC[C@](C)(O)[C@H]1CCC(C)=CC1 RGZSQWQPBWRIAQ-CABCVRRESA-N 0.000 description 1
- CRDAMVZIKSXKFV-FBXUGWQNSA-N (2-cis,6-cis)-farnesol Chemical compound CC(C)=CCC\C(C)=C/CC\C(C)=C/CO CRDAMVZIKSXKFV-FBXUGWQNSA-N 0.000 description 1
- 239000000260 (2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol Substances 0.000 description 1
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical class OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- YYGNTYWPHWGJRM-UHFFFAOYSA-N (6E,10E,14E,18E)-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene Chemical compound CC(C)=CCCC(C)=CCCC(C)=CCCC=C(C)CCC=C(C)CCC=C(C)C YYGNTYWPHWGJRM-UHFFFAOYSA-N 0.000 description 1
- 229940043268 2,2,4,4,6,8,8-heptamethylnonane Drugs 0.000 description 1
- JNAYPSWVMNJOPQ-UHFFFAOYSA-N 2,3-bis(16-methylheptadecanoyloxy)propyl 16-methylheptadecanoate Chemical compound CC(C)CCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCC(C)C)COC(=O)CCCCCCCCCCCCCCC(C)C JNAYPSWVMNJOPQ-UHFFFAOYSA-N 0.000 description 1
- AVTLBBWTUPQRAY-UHFFFAOYSA-N 2-(2-cyanobutan-2-yldiazenyl)-2-methylbutanenitrile Chemical compound CCC(C)(C#N)N=NC(C)(CC)C#N AVTLBBWTUPQRAY-UHFFFAOYSA-N 0.000 description 1
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 1
- LVDXDNDMOQYDMZ-UHFFFAOYSA-N 2-[2-(2-phenylmethoxypropoxy)propoxy]propyl tetradecanoate Chemical compound CCCCCCCCCCCCCC(=O)OCC(C)OCC(C)OCC(C)OCc1ccccc1 LVDXDNDMOQYDMZ-UHFFFAOYSA-N 0.000 description 1
- NBTXFNJPFOORGI-UHFFFAOYSA-N 2-ethenoxyethyl prop-2-enoate Chemical compound C=COCCOC(=O)C=C NBTXFNJPFOORGI-UHFFFAOYSA-N 0.000 description 1
- ZACVGCNKGYYQHA-UHFFFAOYSA-N 2-ethylhexoxycarbonyloxy 2-ethylhexyl carbonate Chemical compound CCCCC(CC)COC(=O)OOC(=O)OCC(CC)CCCC ZACVGCNKGYYQHA-UHFFFAOYSA-N 0.000 description 1
- QSNJNCHUFWULBZ-UHFFFAOYSA-N 2-ethylhexyl 16-methylheptadecanoate Chemical compound CCCCC(CC)COC(=O)CCCCCCCCCCCCCCC(C)C QSNJNCHUFWULBZ-UHFFFAOYSA-N 0.000 description 1
- OPJWPPVYCOPDCM-UHFFFAOYSA-N 2-ethylhexyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(CC)CCCC OPJWPPVYCOPDCM-UHFFFAOYSA-N 0.000 description 1
- HTNFLUQQANUSLR-UHFFFAOYSA-N 2-octanoyloxyethyl octanoate Chemical compound CCCCCCCC(=O)OCCOC(=O)CCCCCCC HTNFLUQQANUSLR-UHFFFAOYSA-N 0.000 description 1
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 1
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 1
- POJWUDADGALRAB-PVQJCKRUSA-N Allantoin Natural products NC(=O)N[C@@H]1NC(=O)NC1=O POJWUDADGALRAB-PVQJCKRUSA-N 0.000 description 1
- 244000144927 Aloe barbadensis Species 0.000 description 1
- 235000002961 Aloe barbadensis Nutrition 0.000 description 1
- 201000004384 Alopecia Diseases 0.000 description 1
- 241001237961 Amanita rubescens Species 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- VLGZEXHEDSZZIC-UHFFFAOYSA-N C(CCCCCCC)(=O)O.C(CCCCCCC)(=O)O.C(CCCCCCC)(=O)O.C(=O)=CC(C=C=O)=C=O Chemical compound C(CCCCCCC)(=O)O.C(CCCCCCC)(=O)O.C(CCCCCCC)(=O)O.C(=O)=CC(C=C=O)=C=O VLGZEXHEDSZZIC-UHFFFAOYSA-N 0.000 description 1
- 244000020518 Carthamus tinctorius Species 0.000 description 1
- 235000003255 Carthamus tinctorius Nutrition 0.000 description 1
- 244000303965 Cyamopsis psoralioides Species 0.000 description 1
- SNPLKNRPJHDVJA-ZETCQYMHSA-N D-panthenol Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCCO SNPLKNRPJHDVJA-ZETCQYMHSA-N 0.000 description 1
- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
- 235000003222 Helianthus annuus Nutrition 0.000 description 1
- 244000020551 Helianthus annuus Species 0.000 description 1
- 241000521257 Hydrops Species 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- 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 1
- 206010061218 Inflammation Diseases 0.000 description 1
- IJMWOMHMDSDKGK-UHFFFAOYSA-N Isopropyl propionate Chemical compound CCC(=O)OC(C)C IJMWOMHMDSDKGK-UHFFFAOYSA-N 0.000 description 1
- 239000004166 Lanolin Substances 0.000 description 1
- 235000019501 Lemon oil Nutrition 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- WTBIAPVQQBCLFP-UHFFFAOYSA-N N.N.N.CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O Chemical compound N.N.N.CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O WTBIAPVQQBCLFP-UHFFFAOYSA-N 0.000 description 1
- 239000006057 Non-nutritive feed additive Substances 0.000 description 1
- YBGZDTIWKVFICR-JLHYYAGUSA-N Octyl 4-methoxycinnamic acid Chemical compound CCCCC(CC)COC(=O)\C=C\C1=CC=C(OC)C=C1 YBGZDTIWKVFICR-JLHYYAGUSA-N 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- 240000008916 Oenothera biennis Species 0.000 description 1
- 235000004496 Oenothera biennis Nutrition 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- OQILCOQZDHPEAZ-UHFFFAOYSA-N Palmitinsaeure-octylester Natural products CCCCCCCCCCCCCCCC(=O)OCCCCCCCC OQILCOQZDHPEAZ-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 208000003251 Pruritus Diseases 0.000 description 1
- 235000004433 Simmondsia californica Nutrition 0.000 description 1
- 244000044822 Simmondsia californica Species 0.000 description 1
- PRXRUNOAOLTIEF-ADSICKODSA-N Sorbitan trioleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@H]1OC[C@H](O)[C@H]1OC(=O)CCCCCCC\C=C/CCCCCCCC PRXRUNOAOLTIEF-ADSICKODSA-N 0.000 description 1
- 239000004147 Sorbitan trioleate Substances 0.000 description 1
- 206010042496 Sunburn Diseases 0.000 description 1
- BHEOSNUKNHRBNM-UHFFFAOYSA-N Tetramethylsqualene Natural products CC(=C)C(C)CCC(=C)C(C)CCC(C)=CCCC=C(C)CCC(C)C(=C)CCC(C)C(C)=C BHEOSNUKNHRBNM-UHFFFAOYSA-N 0.000 description 1
- XEFQLINVKFYRCS-UHFFFAOYSA-N Triclosan Chemical compound OC1=CC(Cl)=CC=C1OC1=CC=C(Cl)C=C1Cl XEFQLINVKFYRCS-UHFFFAOYSA-N 0.000 description 1
- MXNODNKXIIQMMI-UHFFFAOYSA-N [3-decanoyloxy-2,2-bis(decanoyloxymethyl)propyl] decanoate Chemical compound CCCCCCCCCC(=O)OCC(COC(=O)CCCCCCCCC)(COC(=O)CCCCCCCCC)COC(=O)CCCCCCCCC MXNODNKXIIQMMI-UHFFFAOYSA-N 0.000 description 1
- CFRNDJFRRKMHTL-UHFFFAOYSA-N [3-octanoyloxy-2,2-bis(octanoyloxymethyl)propyl] octanoate Chemical compound CCCCCCCC(=O)OCC(COC(=O)CCCCCCC)(COC(=O)CCCCCCC)COC(=O)CCCCCCC CFRNDJFRRKMHTL-UHFFFAOYSA-N 0.000 description 1
- DHFCLYNGVLPKPK-UHFFFAOYSA-N acetamide;2-aminoethanol Chemical compound CC(N)=O.NCCO DHFCLYNGVLPKPK-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229960000458 allantoin Drugs 0.000 description 1
- 235000011399 aloe vera Nutrition 0.000 description 1
- 150000001280 alpha hydroxy acids Chemical class 0.000 description 1
- RGZSQWQPBWRIAQ-LSDHHAIUSA-N alpha-Bisabolol Natural products CC(C)=CCC[C@@](C)(O)[C@@H]1CCC(C)=CC1 RGZSQWQPBWRIAQ-LSDHHAIUSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 229920006318 anionic polymer Polymers 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 239000013011 aqueous formulation Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 150000001277 beta hydroxy acids Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229940036350 bisabolol Drugs 0.000 description 1
- HHGZABIIYIWLGA-UHFFFAOYSA-N bisabolol Natural products CC1CCC(C(C)(O)CCC=C(C)C)CC1 HHGZABIIYIWLGA-UHFFFAOYSA-N 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 239000007844 bleaching agent Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 229920003118 cationic copolymer Polymers 0.000 description 1
- 239000010627 cedar oil Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000010632 citronella oil Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000012505 colouration Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000008406 cosmetic ingredient Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 230000002354 daily effect Effects 0.000 description 1
- PWEOPMBMTXREGV-UHFFFAOYSA-N decanoic acid;octanoic acid;propane-1,2-diol Chemical compound CC(O)CO.CCCCCCCC(O)=O.CCCCCCCC(O)=O.CCCCCCCCCC(O)=O.CCCCCCCCCC(O)=O PWEOPMBMTXREGV-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 125000004386 diacrylate group Chemical group 0.000 description 1
- IOBZMMXOKDNXPQ-UHFFFAOYSA-N dodecanamide;2-(2-hydroxyethylamino)ethanol Chemical compound OCCNCCO.CCCCCCCCCCCC(N)=O IOBZMMXOKDNXPQ-UHFFFAOYSA-N 0.000 description 1
- SYELZBGXAIXKHU-UHFFFAOYSA-N dodecyldimethylamine N-oxide Chemical compound CCCCCCCCCCCC[N+](C)(C)[O-] SYELZBGXAIXKHU-UHFFFAOYSA-N 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
- 229940093471 ethyl oleate Drugs 0.000 description 1
- GJQLBGWSDGMZKM-UHFFFAOYSA-N ethylhexyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC(CC)CCCCC GJQLBGWSDGMZKM-UHFFFAOYSA-N 0.000 description 1
- 229940045761 evening primrose extract Drugs 0.000 description 1
- 235000008524 evening primrose extract Nutrition 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 229940043259 farnesol Drugs 0.000 description 1
- 229930002886 farnesol Natural products 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 230000009969 flowable effect Effects 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000000118 hair dye Substances 0.000 description 1
- 208000024963 hair loss Diseases 0.000 description 1
- 230000003676 hair loss Effects 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 239000003906 humectant Substances 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- ZCTXEAQXZGPWFG-UHFFFAOYSA-N imidurea Chemical compound O=C1NC(=O)N(CO)C1NC(=O)NCNC(=O)NC1C(=O)NC(=O)N1CO ZCTXEAQXZGPWFG-UHFFFAOYSA-N 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 239000000077 insect repellent Substances 0.000 description 1
- KUVMKLCGXIYSNH-UHFFFAOYSA-N isopentadecane Natural products CCCCCCCCCCCCC(C)C KUVMKLCGXIYSNH-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229940093629 isopropyl isostearate Drugs 0.000 description 1
- 229940074928 isopropyl myristate Drugs 0.000 description 1
- 230000007803 itching Effects 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 229940039717 lanolin Drugs 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 229940048866 lauramine oxide Drugs 0.000 description 1
- 239000010501 lemon oil Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000001525 mentha piperita l. herb oil Substances 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 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
- 229940078555 myristyl propionate Drugs 0.000 description 1
- ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 description 1
- 229920001206 natural gum Polymers 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 238000006902 nitrogenation reaction Methods 0.000 description 1
- FEZFGASTIQVZSC-UHFFFAOYSA-N nonanoyl nonaneperoxoate Chemical compound CCCCCCCCC(=O)OOC(=O)CCCCCCCC FEZFGASTIQVZSC-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
- SRSFOMHQIATOFV-UHFFFAOYSA-N octanoyl octaneperoxoate Chemical compound CCCCCCCC(=O)OOC(=O)CCCCCCC SRSFOMHQIATOFV-UHFFFAOYSA-N 0.000 description 1
- 229960001679 octinoxate Drugs 0.000 description 1
- 229960003921 octisalate Drugs 0.000 description 1
- WCJLCOAEJIHPCW-UHFFFAOYSA-N octyl 2-hydroxybenzoate Chemical compound CCCCCCCCOC(=O)C1=CC=CC=C1O WCJLCOAEJIHPCW-UHFFFAOYSA-N 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000001139 pH measurement Methods 0.000 description 1
- 229940101267 panthenol Drugs 0.000 description 1
- 235000020957 pantothenol Nutrition 0.000 description 1
- 239000011619 pantothenol Substances 0.000 description 1
- 235000019477 peppermint oil Nutrition 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000001738 pogostemon cablin oil Substances 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229940095106 ppg-3 benzyl ether myristate Drugs 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- NEOZOXKVMDBOSG-UHFFFAOYSA-N propan-2-yl 16-methylheptadecanoate Chemical compound CC(C)CCCCCCCCCCCCCCC(=O)OC(C)C NEOZOXKVMDBOSG-UHFFFAOYSA-N 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- 229960003415 propylparaben Drugs 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000012966 redox initiator Substances 0.000 description 1
- 239000006254 rheological additive Substances 0.000 description 1
- 239000010668 rosemary oil Substances 0.000 description 1
- 229940058206 rosemary oil Drugs 0.000 description 1
- 239000010671 sandalwood oil Substances 0.000 description 1
- 229920005573 silicon-containing polymer Polymers 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 239000004296 sodium metabisulphite Substances 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- GNBVPFITFYNRCN-UHFFFAOYSA-M sodium thioglycolate Chemical compound [Na+].[O-]C(=O)CS GNBVPFITFYNRCN-UHFFFAOYSA-M 0.000 description 1
- SPDUKHLMYVCLOA-UHFFFAOYSA-M sodium;ethaneperoxoate Chemical compound [Na+].CC(=O)O[O-] SPDUKHLMYVCLOA-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 229960000391 sorbitan trioleate Drugs 0.000 description 1
- 235000019337 sorbitan trioleate Nutrition 0.000 description 1
- 229940031439 squalene Drugs 0.000 description 1
- TUHBEKDERLKLEC-UHFFFAOYSA-N squalene Natural products CC(=CCCC(=CCCC(=CCCC=C(/C)CCC=C(/C)CC=C(C)C)C)C)C TUHBEKDERLKLEC-UHFFFAOYSA-N 0.000 description 1
- 230000037072 sun protection Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000010677 tea tree oil Substances 0.000 description 1
- 229940111630 tea tree oil Drugs 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- YRZGMTHQPGNLEK-UHFFFAOYSA-N tetradecyl propionate Chemical compound CCCCCCCCCCCCCCOC(=O)CC YRZGMTHQPGNLEK-UHFFFAOYSA-N 0.000 description 1
- CRDAMVZIKSXKFV-UHFFFAOYSA-N trans-Farnesol Natural products CC(C)=CCCC(C)=CCCC(C)=CCO CRDAMVZIKSXKFV-UHFFFAOYSA-N 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 229960003500 triclosan Drugs 0.000 description 1
- 229940098385 triisostearin Drugs 0.000 description 1
- VLPFTAMPNXLGLX-UHFFFAOYSA-N trioctanoin Chemical compound CCCCCCCC(=O)OCC(OC(=O)CCCCCCC)COC(=O)CCCCCCC VLPFTAMPNXLGLX-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- A61K8/8147—Homopolymers or copolymers of acids; Metal or ammonium salts thereof, e.g. crotonic acid, (meth)acrylic acid; Compositions of derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L101/00—Compositions of unspecified macromolecular compounds
- C08L101/12—Compositions of unspecified macromolecular compounds characterised by physical features, e.g. anisotropy, viscosity or electrical conductivity
- C08L101/14—Compositions of unspecified macromolecular compounds characterised by physical features, e.g. anisotropy, viscosity or electrical conductivity the macromolecular compounds being water soluble or water swellable, e.g. aqueous gels
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- A61K8/8158—Homopolymers or copolymers of amides or imides, e.g. (meth) acrylamide; Compositions of derivatives of such polymers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/0241—Containing particulates characterized by their shape and/or structure
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/04—Dispersions; Emulsions
-
- 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
- A61Q19/00—Preparations for care of the skin
- A61Q19/004—Aftersun preparations
-
- 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
- A61Q19/007—Preparations for dry 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
- A61Q5/12—Preparations containing hair conditioners
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q9/00—Preparations for removing hair or for aiding hair removal
- A61Q9/04—Depilatories
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/32—Polymerisation in water-in-oil emulsions
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/44—Preparation of metal salts or ammonium salts
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L101/00—Compositions of unspecified macromolecular compounds
Definitions
- Liquid dispersion polymer compositions their preparation and their use
- the present invention relates to liquid dispersion polymer compositions that comprise a dispersed polymer phase, a continuous carrier phase and a surfactant, their preparation and the use of these liquid dispersion polymer compositions to prepare microparticulate 5 thickening systems, which thicken aqueous, or aqueous/organic compositions. More particularly it relates to liquid dispersion polymer compositions which comprise microparticles of a hydrophilic, water soluble or swellable polymer with a level of neutralization of from about 25 to about 100 %, which is dispersed in a non-aqueous fluid carrier phase, preferably an oil or emollient ester, and an oil-in-water surfactant, their preparation and the use of these
- I0 liquid dispersion polymer compositions to prepare microparticulate thickening systems to thicken aqueous or aqueous/organic compositions, particularly for use in personal care and pharmaceutical formulations.
- Thickeners are used extensively in personal care formulations such as cosmetic and
- Polymeric thickeners have been used for this purpose for many years.
- the types of polymeric thickeners that have been used range from natural gums such as guar, through modified natural materials such as hydroxyethyl cellulose, to synthetic thickeners such as the Carbomers ® based on polyacrylic acids.
- the Salcare ® and Tinovis ® ranges of liquid dispersion polymers, available through Ciba Specialty Chemicals, are ranges of microparticulate acrylic-based polymeric thickeners in a hydrophobic carrier medium.
- Salcare ® SC91 is an anionic thickening agent based on a sodium acrylate polymer and mineral oil carrier with PPG-1 trideceth-6 as the activator 5 surfactant.
- Salcare ® SC92 is a cationic copolymer thickener and conditioner comprising polyquatemium 32 and mineral oil.
- Salcare ® SC95 and Salcare ® SC96 are cationic homopolymer thickeners and conditioners.
- Salcare ® SC95 comprises polyquatemium 37 in mineral oil with PPG-1 trideceth-6.
- Salcare ® SC96 comprises polyquatemium 37 in propylene glycol dicaprylate dicaprate with PPG-1 trideceth-6.
- Salcare ® AST is an anionic 0 thickening agent based on a sodium acrylate polymer in soya bean oil with PPG-1 trideceth- 6.
- the tiny, spherical microparticles of the above hydrophilic acrylic polymers, whether anionic or cationic in charge, have a typical particle size in the range of 0.1 - 2 microns, with an average particle size in the range of 0.5 - 1.0 microns.
- the polymer microparticles are preferably manufactured by methods in which water-soluble vinyl addition monomers are polymerized utilizing a water-in-oil polymerization route.
- the activator surfactant converts the hydrophobic carrier into an oil-in-water e mulsion.
- activator surfactant is meant a surfactant that activates the conversion of the hydrophobic carrier into an oil-in-water emulsion.
- the hydrophilic polymer expands on exposure to water but does not dissolve, resulting in a smooth and rapid viscosity increase.
- the polymer particles swell to give a microparticulate thickening system comprising polymer particles having a typical particle size in the range of 2.5 - 5 microns in diameter.
- microparticulate thickening systems have a pseudoplastic rheological profile which gives good stability and suspension characteristics at low shear rates (such as those experienced by the product on standing), and low apparent viscosities at high shear rates, which corresponds to excellent rub-in characteristics.
- the level of neutralization is defined as
- the level of neutralization goes from 0%, wherein no neutralizable site of the polymer is neutralized up to 100%, wherein all neutralizable sites of the polymer ares neutralized.
- the level of neutralization is measured by conventional acid-base titration to determine the % converted neutralisable sites.
- the present invention provides a liquid dispersion polymer composition
- a liquid dispersion polymer composition comprising a hydrophilic, water soluble or swellable polymer with a neutralization level of from about 25% to about 100 %, preferably from about 30% to about 50 %, more preferred from about 30% to about 45%, especially from about 30% to about 40%, a non-aqueous carrier phase and an oil-in-water surfactant.
- the hydrophilic, water soluble or swellable polymer is used in the form of microparticles having an average particle size in the range of about 0.1 to about 2 microns
- the liquid dispersion polymer composition comprises a) from 35% to 65% by weight of the polymer with a neutralization level of from about 25% to about 50 %, preferably from about 30% to about 50 %, more preferred from about 30% to about 45%, especially from about 30% to about 40%, b) from 20% to 50% by weight of a non-aqueous carrier and c) from 5% to 25% by weight of a surfactant or a surfactant mixture, each based on the total weight of the composition.
- the hydrophilic polymer a) is water swellable, i.e. it is sufficiently cross-linked to swell but not dissolve in water.
- it is acrylic-based.
- it is preferably anionic.
- non-aqueous carrier fluids mentioned in b) are well known to the cosmetic industry and have been used for many years in hair and skin formulations. They include silicone polymers, mineral oil, hydrogenated polydecene, isohexadecane, esters such as trimethyloylpropane tricaprylate/tricaprylate, C ⁇ 2 -C ⁇ 5 alkyl benzoate, ethylhexyl stearate, caprylic capric triglycerides, squalane, ethylhexyl cocoate, decyl oleate, decyl cocoate, ethyl oleate, isopropyl myristate, ethylhexyl perlagonate, pentaerythrityl tetracaprylate/tetracaprate, PPG-3 benzyl ether myristate, propyiene glycol dicaprylate / dicaprate, ethylhexyl isostearate
- the surfactant mixture c) comprises both surfactants useful in the manufacture of the microparticles of swellable polymer a), and at least one surfactant which serves as the activator for the subsequent oil-in-water microparticulate thickening emulsions.
- This activator surfactant for the oil-in-water thickening emulsions comprises from 1.0% to 10.0% by weight of the composition, preferably from 2.0% to 8.0% by weight of the composition.
- the activator surfactant is a nonionic oil-in-water emulsifier having a HLB generally above 7. Suitable emulsifiers of this type are well known to those skilled in the art. Ethoxyla-ted alcohols are preferred.
- composition may contain minor amounts of other components which do not affect its essential characteristics.
- these other components may include up to about 3% by weight each of water and volatile organic solvents as well as small amounts of other components which are left over from the preparation of the water soluble or swellable polymers.
- composition (A) comprises a) from 40% to 60% by weight of the polymer with a neutralization level of from about 25% to about 50 %, preferably from about 30% to about 50 %, more preferred from about 30% to about 45%, especially from about 30% to about 40%, wherein the polymer is anionic and is water swellable, b) from 25% to 45% by weight of a non-aqueous carrier fluid, and c) from 8% to 20% by weight of a surfactant or a surfactant mixture, each based on the total weight of the composition.
- a particularly preferred composition (B) comprises a) from 45% to 58% by weight of the polymer with a neutralization level of from about 25% to about 50 %, preferably from about 30% to about 50 %, more preferred from about 30% to about 45%, especially from about 30% to about 40%, wherein the polymer is anionic and is water swellable, b) from 30% to 40% by weight of a non-aqueous carrier fluid and c) from 10% to 18% by weight of a mixture of surfactants, each based on the total weight of the composition.
- a very particularly preferred composition (C) comprises a) from 45% to 58% by weight of the water swellable polymer with a neutral izatio ⁇ level of from about 25% to about 50 %, preferably from about 30% to about 50 %, more preferred from about 30% to about 45%, especially from about 30% to about 40%, wherein the polymer is anionic, b) from 32% to 38% by weight of a non-aqueous carrier fluid c) from 12% to 18% by weight of a mixture of surfactants, each based on the total weight of the composition.
- compositions (D) in particular personal care formulations, which comprise a) 0.1 % to 8% by weight, preferably 1 % to 6% by weight of a liquid dispersion pol ymer composition (A), (B) or (C) as described above, b) 0.1 % to 70%, preferably 2% to 35% by weight of additional ingredients, for example personal care ingredients such as cosmetic or pharmaceutical excipients and/or active ingredients and c) 45% to 99% of water or a mixture of water and a water-miscible organic solvent such as a lower alcohol, each based on the total weight of the composition.
- D thickened aqueous or water- containing compositions
- Such lower alcohols include ethanol, isopropyl alcohol, propyiene glycol, di-isopropyl alcohol and other known lower alcohols.
- Still another aspect of the present invention is the provision of non-aqueous liquid or solid compositions, such as colour cosmetics or soaps, where the polymer of the present invention provides some additional benefit, such as improved wear properties.
- compositions may be in the form of lotions, creams, salves, gels, milks, sprays, foams or ointments.
- the additional components can be any ingredient that may form part of a thickened -aqueous emulsion of the oil-in-water type.
- cosmetic ingredients incl ude antimicrobials (such as triclosan or farnesol); skin conditioning agents and emollients such as lanolin and derivatives thereof; esters such as iso-propyl propanoate, decyl oleate, isopropyl isostearate, trioctanoin, triisostearin.
- myristyl propionate fatty alochols; squalene; silicones such as cyclomethicone, dimethicone, dimethicone copolyol; acetamide monoethanolamine; dimethyl polysiloxane; moisturizers such as aloe vera, barrier creams, emollients, alpha and beta hydroxy acids such as lactic acid and glycolic acid; anti-inflammatory actives like allantoin and bisabolol; UV sun screening agents such as para aminobenzoic acid, octyl salicylate, and octyl methoxycinnamate, "sunless” tanning agents, whitening agents, insect repellents, essential oils such as patchouli oil, peppermint oil, rosemary oil, citronella oil, tea tree oil, orange or lemon oils, cedarwood oil and sandalwood oil, vitamins, colours and pigments; hair conditioners such as amodimethicone, cyclomethicone, panthenol, lauramide
- Still another aspect of the present invention is the provision of a method for the preparation of a therapeutic lotion, cream, salve, gel or ointment which comprises mixing 0.1% to 8% by weight, preferably 1% to 6% by weight of a liquid dispersion polymer as described above into an aqueous or aqueous/organic composition which contains from 0.1% to 70% by weight of at least one therapeutic agent and/or excipient.
- Still another aspect of the present invention is the provision of a method for the topical treatment of the skin or hair, which comprises applying a composition as defined above to the skin, face, hair or scalp of a human being or other mammal in need of such treatment.
- a composition as defined above to the skin, face, hair or scalp of a human being or other mammal in need of such treatment.
- the type of treatment will depend on the active ingredient(s) dissolved or suspended in the composition.
- the composition may comprise facial creams such as barrier cream, a moisturizer cream, lotion or milk, a cleanser or toner, a hand and body milk or lotion, a body spray, creams, lotions or milks containing sun-screens against UV-A and UV-B radiation, a "sunless" tanning cream, lotion or spray, a skin bleaching cream, lotion or spray, a depilatory cream, a hair conditioning cream, lotion or shampoo, a hair dyeing cream or lotion, a pre- or aftershave cream, lotion, gel or balm, a disinfectant cream, lotion, ointment or gel, a soothing cream, lotion or spray as an after sun application for sunburn, etc.
- facial creams such as barrier cream, a moisturizer cream, lotion or milk, a cleanser or toner, a hand and body milk or lotion, a body spray, creams, lotions or milks containing sun-screens against UV-A and UV-B radiation
- a "sunless" tanning cream, lotion or spray a
- the hydrophilic, water swellable acrylic-based liquid dispersion polymer compositions employed in the present invention are overall anionic in character.
- Said polymers with a neutralization level of from about 25% to about 50 % may be homopolymers or copolymers. They are formed from one or more mo ⁇ oethylenically unsaturated monomers that are either water soluble anionic monomers or from a predominantly anionic blend of monomers that may consist of a mixture of anionic monomers and a minor amount of nonionic monomers.
- the polymers with a neutralization level of from about 25% to about 50 % may conveniently be obtained in the form of microparticles having an average particle size in the range of 0.1 - 2 microns by reverse phase emulsion polymerization of suitable monomers in a hydrophobic liquid, i.e. a liquid which has sufficiently low miscibility with water that it can be used as the non-aqueous phase in a reverse phase polymerization.
- a hydrophobic liquid i.e. a liquid which has sufficiently low miscibility with water that it can be used as the non-aqueous phase in a reverse phase polymerization.
- the liquid must have substantially no solvating effect for the polymer, or for the monomers from which it is formed, throughout the range of temperatures at which the polymer is likely to be synthesized (for instance from 15 to 100°C), since a solvating medium would be unsatisfactory for reverse phase emulsion polymerization.
- the monomer or monomer blend must be water soluble to enable reverse phase poly
- Suitable anionic monomers include acrylic acid, methacrylic acid and their alkali metal and ammonium salts, 2-acrylamido-2-methyl-propanesulfonic acid and its salts, sodium styrene sulfonate and the like.
- Acrylic acid is the most preferred anionic monomer.
- the carboxylic acid groups are between 20 and 80%, advantageously 30-45% in the form of an alkali metal salt or ammonium salt, especially the sodium salt.
- Suitable nonionic monomers include acrylamide, methacrylamide, N.N,-dialkylacrylamides, N-vinyl pyrrolidone and water soluble hydroxy-substituted acrylic or methacrylic esters.
- the amount of anionic monomer is preferably more than 60% by weight of the blend, and usually it is at least 80% by weight of the blend.
- the preferred anionic polymers are formed wholly from anionic monomers.
- the liquid dispersion polymer compositions are advantageously crosslinked by incorporating a small amount of a suitable crosslinking agent such as a polyfunctional vinyl addition monomer into the polymerization mixture.
- a water-soluble crosslinking agent is used.
- any of the conventional ethylenically unsaturated cross linking agents or poly ethylenically unsaturated cross linking agents which are soluble in the monomer or monomer blend can be used, including materials which are di-, tri- or tetraethylenically unsaturated.
- Preferred are diethylenically unsaturated compounds such as methylene bis acrylamide.
- cross-linking agents are tetra allyl ammonium chloride; allyl-acrylamides and allyl-methacrylamides; bisacrylamidoacetic acid and N.N'-methylene-bisacrylamide.
- cross-linking agents are tetra allyl ammonium chloride and N .
- N'- methylene-bisacrylamide are the most preferred cross-linking agents.
- the amount of cross linking agent is generally in the range from 100 to 10,000 parts by weight of cross linking agent per million parts (by dry weight) of monomer. Most preferably it is around 500 to 2000 ppm, especially 500 to 900 ppm for either cationic or anionic monomers. Optimum amounts can be determined by routine experimentation.
- the hydrophilic polymers are prepared by reverse phase emulsion polymerization of hydrophilic monomers, preferably one or more acrylate and/or methacrylate monomers, in a hydrophobic liquid phase.
- Reverse phase emulsion polymerization is a well known technique which is described for example in U.S. Patent 4,628,078, the disclosure of which is incorporated by reference in its entirety.
- the continuous phase for the preparation of the instant liquid dispersion polymer compositions is provided at least in part by a non-aqueous carrier fluid.
- non-aqueous carrier fluids which are cosmetically and/or pharmaceutically acceptable and which are sufficiently hydrophobic to be useful as the continuous phase in a reverse phase polymerization are preferably used as the continuous phase.
- non-aqueous carrier fluids include mineral oil, hydrogenated polydecene, natural oils including soya bean oil, Squalane, emollient esters including propyiene glycol Dicaprate caprylate.
- the preferred non-aqueous carrier fluid is mineral oil.
- the amount of the hydrophobic liquid phase used in the polymerization is dictated primarily by the need to provide a satisfactory reverse phase emulsion medium. This would generally be at least about 0.5 parts by weight of the non-aqueous carrier fluid per part by weight of the hydrophilic polymer (dry weight).
- a volatile inert hydrophobic solvent Suitable inert hydrophobic solvents include hydrocarbons and halogenated hydrocarbons.
- One particularly preferred hydrocarbon mixture is Isopar G ® (Trademark of Exxon Mobil Corporation). Conveniently 1 to 2 parts, preferably 1.3 to 1.9 parts of the volatile inert hydrophobic solvent per part of the hydrop>hilic polymer on a dry weight basis is employed.
- the polymer is prepared by conventional reverse phase emulsion procedures, namely by adding 1 part by weight (dry weight) of at least one aqueous ethyle nically unsaturated monomer, optionally including a sequesterant and a crosslinking ethylenically unsaturated monomer, into about 1 to 3 parts by weight of a hydrophobic liquid comprising at least in part a non-aqueous carrier fluid and containing about 0.1 to 0.2 parts of at least one conventional water-in-oil emulsifier having a HLB value below 9.0 and optionally 0.5 to 10.0 parts of a polymeric stabilizer surfactant, with intensive agitation so as to form a substantially stable emulsion of the required fine particle size.
- a hydrophobic liquid comprising at least in part a non-aqueous carrier fluid and containing about 0.1 to 0.2 parts of at least one conventional water-in-oil emulsifier having a HLB value below 9.0 and optionally 0.5 to 10.0 parts of
- Suitable water-in-oil e ⁇ nulsifiers are well known to those skilled in the art. Sorbitan esters are preferred. Diethylenetr ⁇ amine pentaacetic acid, sodium salt is a suitable sequesterant. The ethylenically unsaturated monomer may be diethylenically or polyethylenically unsaturated.
- the reaction mixture is purged with nitrogen and polymerization is initiated by addition of a conventional source of free radicals.
- Suitable polymerization initiators are well known to those skilled in the art.
- Typical free radical-forming catalysts include peroxygen compounds such as sodium, potassium and ammonium persulfates, caprylyl peroxide, benzoyl peroxide, hydrogen peroxide, pelargonyl peroxide, cumene hydroperoxide, tertiary butyl diperphthalate, tertiary butyl perbenzoate, sodium peracetate, di(2-ethylhexyl)peroxydicarbonate, and the like, as well as azo catalysts such as azodiisobutyronitrile.
- Other useful catalysts are the heavy metal-activated catalyst systems.
- a preferred type of polymerization initiator is a redox initiation pair. After initiation appropriate temperature and agitation conditions are maintained until the conversion of the monomer to polymer is substantially complete. Appropriate conditions are well known to those of ordinary skill in the art.
- the water and any volatile solvent are then removed from the reverse phase emulsion, for example by distillation under reduced pressure, so as to produce a substantially anhydrous stable dispersion of polymer particles less than 2 microns in size dispersed in the non- aqueous continuous phase.
- a nonionic oil-in-water emulsifier having a HLB generally above 7 is added after distillation is complete.
- Suitable emulsifiers of this type are well known to those skilled in the art. Ethoxylated alcohols are preferred.
- the level of neutralization is adjusted by maintaining the monomer phase temperature below 30°C and adding a metal alkali, including but not limited to sodium hydroxide, lithium hydroxide, potassium hydroxide, or nitrogen containing bases, including and not limited to ammonium hydroxide or simple amines, to the monomer phase in order to neutralize the required molar ratio of carboxylic sites measured by conventional acid-base titration or by known pH measurement systems.
- a metal alkali including but not limited to sodium hydroxide, lithium hydroxide, potassium hydroxide, or nitrogen containing bases, including and not limited to ammonium hydroxide or simple amines
- a suitable polymeric stabiliser surfactant is employed as a processing aid to maintain emulsion integrity through the distillation process and to provide for the final liquid polymer dispersion to be a free flowing liquid, even when it contains high levels of microparticles of the water soluble or swellable dispersed polymer.
- 0.5 to 10.0 parts, preferably 1.0 to 6.0 parts, of this polymeric surfactant is employed per part by weight (dry weight) of the ethylenically unsaturated monomer.
- a preferred polymeric surfactant is a copolymer of an alkyl (meth)acrylate monomer and an amino functional monomer, which may be prepared as follows:
- Alkyl (meth)acrylate, amino functional monomer and a suitable oil soluble thermal initiator for example 2,2'-Azobis(2-methylbutyronitrile)
- an inert solvent for example an aliphatic or aromatic hydrocarbon solvent such as Isopar G.
- This mixture is fed into a vessel containing further solvent and thermal initiator over a period of 2 to 6 hours at reaction temperatures of 80 to 90°C. The reaction is maintained at this temperature for a further two hours before being cooled and run off.
- the alkyl group of the Alkyl (meth)acrylate may be any suitable alkyl group, however C 8 to C 2 2 grou ps are preferred .
- the amino functional monomer is of the general formula (1):
- R is hydrogen or CrC 4 alkyl
- X is -O- or-NH-.
- B is CrC 4 alkylene
- R 1 is hydrogen or C C ⁇ oalkyl
- R 2 is CrCtoalkyl
- the alkyl (meth)acrylate : amino functional monomer ratio may be between 0.5 to 8.0 : 1 on a molar basis. Preferably between 0.75 to 6.0 : 1, and most preferably between 1.0 to 4.0 : 1 on a molar basis.
- the molecular weight may be determined by conventional chromatography techniques well known to those skilled in the art. Typical molecular weights may be in the range of 10,000 to 60,000, most typically in the range of 15,000 to 40,000.
- the non-ionic surfactant Upon stirring the liquid dispersion into an aqueous system, the non-ionic surfactant converts the hydrophobic carrier into an oil-in-water emulsion.
- the hydropr-iilic polymer expands on exposure to water resulting in a smooth and rapid viscosity increase.
- the polymer particles swell to give a microparticulate thickening system comprising polymer particles having a typical particle size in the range of 2.5 to 5.0 microns.
- inventive liquid dispersion compositions provide microparticulate thickening systems which give effective thickening to aqueous or aqueous/organic formulations at concentrations of 0.1 to 8.0 %. Preferably 1% to 6% by weight. In addition however they combines the thickening effect of the liquid dispersion polymer with emolliency and sensorial effects delivered by the skilled selection of a suitable non-aqueous carrier fluid.
- liquid dispersion polymer compositions are compatible with a wide variety of personal care active ingredients and auxiliaries.
- Typical formulation examples where the polymers may be used include:
- Skin Care formulations including all kind of face and body emulsions like creams, I otions, milks and sprays for caring, cleansing, deodorisation and depiliation, colour cosmetics such as; liquid foundations, liquid eyeshadows, liquid blushers, lipsticks and aqueous irt ascaras; facial masks, lip balms, skin care formulations like body washes, all kind of shaving products; hand soaps, soap bars and soap liquids.
- Hair Care formulations which include; hair conditioners, hair colourations (permanent, semi- permanent and temporary), styling gels, lotions and creams, shampoos, hair relaxers, hair perms and hair masks.
- Sun Tan formulations such as: sun tan creams, lotions and sprays, sun blocks, tan accelerators, after sun creams, lotions and sprays and sunless tanning lotions or creams.
- aqueous phase of water soluble components is prepared by admixing together the following components:
- An “oil phase” is prepared by mixing together the following components:
- the two phases are mixed together in a ratio of 0.751 parts oil phase to 1.0 parts aqueous phase under high shear to form a water-in-oil emulsion
- the resulting water-in-oil emulsion is transferred to a reactor equipped with nitrogen sparge tube, stirrer and thermometer.
- the emulsion is purged with nitrogen to remove oxygen
- Polymerisation is effected by addition of a redox couple of sodium metabisulphite and tertiary butyl Hydroperoxide.
- the level of neutralization is adjusted to a value between 30 and 40%.
- Example 2 Comparison of thickening efficiency at different levels of neutralization
- the thickening efficiency of polymers of the present invention prepared at a range of levels of neutralization has been compared in aqueous solutions and in a dilute ionic solution.
- Example 3 Depilatory Cream This formulation allows the formulation of depilatory creams based on sodium thioglycollate. Adjusting the amount of thickener used can change the product from a roll-on lotion to a viscous cream.
- sodium hydroxide is added to adjust the OH-value in the range of 12 - 13.
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Dermatology (AREA)
- Medicinal Chemistry (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Dispersion Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- General Chemical & Material Sciences (AREA)
- Cosmetics (AREA)
- Medicinal Preparation (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
Abstract
Description
Claims
Priority Applications (8)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2007506767A JP4989458B2 (en) | 2004-04-06 | 2005-03-30 | Polymer dispersion composition, its preparation and its use |
EP05743005A EP1756168B1 (en) | 2004-04-06 | 2005-03-30 | Liquid dispersion polymer compositions, their preparation and their use |
KR1020067020606A KR101239147B1 (en) | 2004-04-06 | 2005-03-30 | Liquid Dispersion Polymer Compositions, their preparation and their use |
AT05743005T ATE437896T1 (en) | 2004-04-06 | 2005-03-30 | LIQUID DISPERSION POLYMER COMPOSITIONS, THEIR PREPARATION AND THEIR USE |
BRPI0509659A BRPI0509659B8 (en) | 2004-04-06 | 2005-03-30 | process for preparing an aqueous dispersion polymer composition |
DE602005015704T DE602005015704D1 (en) | 2004-04-06 | 2005-03-30 | Liquid dispersions, their preparation and their use |
US11/547,214 US20080275138A1 (en) | 2004-04-06 | 2005-03-30 | Liquid Dispersion Polymer Compositions, Their Preparation And Their Use |
US15/256,471 US20160367466A1 (en) | 2004-04-06 | 2016-09-02 | Liquid Dispersion Polymer Compositions, Their Preparation And Their Use |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP04101419 | 2004-04-06 | ||
EP04101419.2 | 2004-04-06 |
Related Child Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US11/547,214 A-371-Of-International US20080275138A1 (en) | 2004-04-06 | 2005-03-30 | Liquid Dispersion Polymer Compositions, Their Preparation And Their Use |
US15/256,471 Continuation US20160367466A1 (en) | 2004-04-06 | 2016-09-02 | Liquid Dispersion Polymer Compositions, Their Preparation And Their Use |
Publications (2)
Publication Number | Publication Date |
---|---|
WO2005097834A2 true WO2005097834A2 (en) | 2005-10-20 |
WO2005097834A3 WO2005097834A3 (en) | 2006-03-02 |
Family
ID=34928938
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2005/051429 WO2005097834A2 (en) | 2004-04-06 | 2005-03-30 | Liquid dispersion polymer compositions, their preparation and their use |
Country Status (10)
Country | Link |
---|---|
US (2) | US20080275138A1 (en) |
EP (1) | EP1756168B1 (en) |
JP (2) | JP4989458B2 (en) |
KR (1) | KR101239147B1 (en) |
CN (2) | CN1964993A (en) |
AT (1) | ATE437896T1 (en) |
BR (1) | BRPI0509659B8 (en) |
DE (1) | DE602005015704D1 (en) |
ES (1) | ES2329488T3 (en) |
WO (1) | WO2005097834A2 (en) |
Cited By (27)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2010054495A2 (en) * | 2008-11-14 | 2010-05-20 | Profimed S.R.O. | Non-aqueous colloidal formulation |
WO2013068392A1 (en) | 2011-11-11 | 2013-05-16 | Basf Se | Thickener containing at least one polymer based on associative monomers |
WO2013068388A1 (en) | 2011-11-11 | 2013-05-16 | Basf Se | Thickener containing at least one polymer based on associative monomers and which can be obtained by inverse emulsion polymerization |
WO2013068394A1 (en) | 2011-11-11 | 2013-05-16 | Basf Se | Thickener containing at least one cationic polymer |
WO2013068387A1 (en) | 2011-11-11 | 2013-05-16 | Basf Se | Thickener containing at least one cationic polymer which can be obtained by inverse emulsion poylmerisation |
EP2666789A1 (en) | 2012-05-21 | 2013-11-27 | Basf Se | Inverse dispersion comprising an anionic or a nonionic polymer and a stabilizing agent |
WO2013174622A1 (en) | 2012-05-21 | 2013-11-28 | Basf Se | Inverse dispersion comprising a cationic polymer and a stabilizing agent |
FR3002229A1 (en) * | 2013-02-21 | 2014-08-22 | Snf Sas | PROCESS FOR LOW CONCENTRATION REVERSE EMULSION POLYMERIZATION OF LOWLY NEUTRALIZED POLYMERS AND INVERSE EMULSIONS OBTAINED |
WO2015052426A1 (en) | 2013-10-07 | 2015-04-16 | S.P.C.M. Sa | Use in cosmetics of polymers obtained by low-concentration, inverse emulsion polymerisation with a low level of neutralised monomers |
US9102900B2 (en) | 2012-05-21 | 2015-08-11 | Basf Se | Inverse dispersion comprising a cationic polymer and a stabilizing agent |
US9200242B2 (en) | 2011-11-11 | 2015-12-01 | Basf Se | Thickener comprising at least one cationic polymer |
US9862853B2 (en) | 2007-03-12 | 2018-01-09 | Croda Singapore Pte Limited | Dispersion, gel and emulsification system |
WO2019016334A1 (en) | 2017-07-21 | 2019-01-24 | Basf Se | A process for obtaining a polymer based on anionic or nonionic monomers with an at least bimodal molecular weight distribution |
WO2019016336A1 (en) | 2017-07-21 | 2019-01-24 | Basf Se | Polymer based on anionic or nonionic monomers with an at least bimodal molecular weight distribution |
US10266792B2 (en) | 2014-07-23 | 2019-04-23 | The Procter & Gamble Company | Treatment compositions |
US10357410B2 (en) | 2014-11-06 | 2019-07-23 | The Procter & Gamble Company | Pre-strained laminates and methods for making the same |
US10407649B2 (en) | 2014-08-06 | 2019-09-10 | S.P.C.P. Sa | Use in detergent compositions of polymers obtained by low-concentration reverse emulsion polymerization with a low content of neutralized monomers |
US10519402B2 (en) | 2014-07-23 | 2019-12-31 | The Procter & Gamble Company | Treatment compositions |
US10538719B2 (en) | 2014-07-23 | 2020-01-21 | The Procter & Gamble Company | Treatment compositions |
US10626351B2 (en) | 2014-07-23 | 2020-04-21 | The Procter & Gamble Company | Treatment compositions |
US10676693B2 (en) | 2014-07-23 | 2020-06-09 | The Procter & Gamble Company | Treatment compositions |
US10689600B2 (en) | 2016-01-25 | 2020-06-23 | The Procter & Gamble Company | Treatment compositions |
US10723975B2 (en) | 2014-07-23 | 2020-07-28 | The Procter & Gamble Company | Treatment compositions |
US10844321B2 (en) | 2014-07-23 | 2020-11-24 | The Procter & Gamble Company | Treatment compositions |
US11136534B2 (en) | 2011-11-11 | 2021-10-05 | Basf Se | Thickener comprising at least one cationic polymer preparable by inverse emulsion polymerization |
US11213436B2 (en) | 2017-02-16 | 2022-01-04 | The Procter & Gamble Company | Substrates having repeating patterns of apertures for absorbent articles |
US11261402B2 (en) | 2016-01-25 | 2022-03-01 | The Procter & Gamble Company | Treatment compositions |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8053004B2 (en) * | 2007-10-08 | 2011-11-08 | Starmaker Products, Llc | Ointment for topical treatment of hot flashes and method of use |
GB0922624D0 (en) * | 2009-12-24 | 2010-02-10 | Croda Int Plc | Inverse emulsions |
US9205037B2 (en) * | 2011-07-20 | 2015-12-08 | Church & Dwight Co., Inc. | Single phase depilatory composition |
US20130045257A1 (en) * | 2011-08-16 | 2013-02-21 | Ali Alwattari | Aerosol shave composition comprising a hydrophobical agent forming at least one microdroplet and an anti-irritation agent |
BR112015010706B1 (en) * | 2012-11-14 | 2022-05-17 | Basf Se | Process for the production of mineral oil |
EP2784038A1 (en) * | 2013-03-26 | 2014-10-01 | Basf Se | Flow agent on additives |
WO2022049370A1 (en) | 2020-09-03 | 2022-03-10 | Independence Oilfield Chemicals Llc | Hydraulic fracturing |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4677152A (en) * | 1984-08-15 | 1987-06-30 | Allied Colloids Limited | Polymeric compositions |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP3119900B2 (en) * | 1991-07-11 | 2000-12-25 | 三菱化学株式会社 | Method for producing superabsorbent polymer |
JP3625893B2 (en) * | 1995-05-25 | 2005-03-02 | 大阪有機化学工業株式会社 | Hairdressing fee |
JP3655720B2 (en) * | 1996-12-04 | 2005-06-02 | 株式会社ファンケル | Emulsified composition |
JP4113614B2 (en) | 1998-03-30 | 2008-07-09 | 株式会社ダイゾー | Gel-like product manufacturing method |
AU770521B2 (en) * | 1999-04-07 | 2004-02-26 | Ciba Specialty Chemicals Holding Inc. | Liquid dispersion polymer compositions, their preparation and their use |
US6635702B1 (en) * | 2000-04-11 | 2003-10-21 | Noveon Ip Holdings Corp. | Stable aqueous surfactant compositions |
GB0029198D0 (en) * | 2000-11-30 | 2001-01-17 | Ciba Sc Holding Ag | Liquid dispersion polymer compositions their preparation and their use |
KR101100623B1 (en) * | 2002-07-16 | 2012-01-03 | 가부시키가이샤 시세이도 | Oil-in-water emulsion composition containing particles |
-
2005
- 2005-03-30 JP JP2007506767A patent/JP4989458B2/en active Active
- 2005-03-30 CN CNA2005800185238A patent/CN1964993A/en active Pending
- 2005-03-30 DE DE602005015704T patent/DE602005015704D1/en active Active
- 2005-03-30 ES ES05743005T patent/ES2329488T3/en active Active
- 2005-03-30 AT AT05743005T patent/ATE437896T1/en not_active IP Right Cessation
- 2005-03-30 WO PCT/EP2005/051429 patent/WO2005097834A2/en active Application Filing
- 2005-03-30 CN CN200910158675.8A patent/CN101671407B/en active Active
- 2005-03-30 KR KR1020067020606A patent/KR101239147B1/en active IP Right Grant
- 2005-03-30 BR BRPI0509659A patent/BRPI0509659B8/en active IP Right Grant
- 2005-03-30 EP EP05743005A patent/EP1756168B1/en active Active
- 2005-03-30 US US11/547,214 patent/US20080275138A1/en not_active Abandoned
-
2012
- 2012-02-13 JP JP2012028895A patent/JP2012102339A/en active Pending
-
2016
- 2016-09-02 US US15/256,471 patent/US20160367466A1/en not_active Abandoned
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4677152A (en) * | 1984-08-15 | 1987-06-30 | Allied Colloids Limited | Polymeric compositions |
Cited By (42)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9862853B2 (en) | 2007-03-12 | 2018-01-09 | Croda Singapore Pte Limited | Dispersion, gel and emulsification system |
WO2010054495A3 (en) * | 2008-11-14 | 2011-01-06 | Profimed S.R.O. | Non-aqueous colloidal formulation |
WO2010054495A2 (en) * | 2008-11-14 | 2010-05-20 | Profimed S.R.O. | Non-aqueous colloidal formulation |
US9200242B2 (en) | 2011-11-11 | 2015-12-01 | Basf Se | Thickener comprising at least one cationic polymer |
WO2013068392A1 (en) | 2011-11-11 | 2013-05-16 | Basf Se | Thickener containing at least one polymer based on associative monomers |
WO2013068388A1 (en) | 2011-11-11 | 2013-05-16 | Basf Se | Thickener containing at least one polymer based on associative monomers and which can be obtained by inverse emulsion polymerization |
WO2013068394A1 (en) | 2011-11-11 | 2013-05-16 | Basf Se | Thickener containing at least one cationic polymer |
WO2013068387A1 (en) | 2011-11-11 | 2013-05-16 | Basf Se | Thickener containing at least one cationic polymer which can be obtained by inverse emulsion poylmerisation |
US11136534B2 (en) | 2011-11-11 | 2021-10-05 | Basf Se | Thickener comprising at least one cationic polymer preparable by inverse emulsion polymerization |
WO2013174622A1 (en) | 2012-05-21 | 2013-11-28 | Basf Se | Inverse dispersion comprising a cationic polymer and a stabilizing agent |
US9102900B2 (en) | 2012-05-21 | 2015-08-11 | Basf Se | Inverse dispersion comprising a cationic polymer and a stabilizing agent |
WO2013174621A1 (en) | 2012-05-21 | 2013-11-28 | Basf Se | Inverse dispersion comprising an anionic or a nonionic polymer and a stabilizing agent |
EP2666789A1 (en) | 2012-05-21 | 2013-11-27 | Basf Se | Inverse dispersion comprising an anionic or a nonionic polymer and a stabilizing agent |
WO2014128400A1 (en) | 2013-02-21 | 2014-08-28 | S.P.C.M. Sa | Process for low-concentration, inverse emulsion polymerization of weakly neutralized polymers and inverse emulsions obtained |
FR3002229A1 (en) * | 2013-02-21 | 2014-08-22 | Snf Sas | PROCESS FOR LOW CONCENTRATION REVERSE EMULSION POLYMERIZATION OF LOWLY NEUTRALIZED POLYMERS AND INVERSE EMULSIONS OBTAINED |
US9290588B2 (en) | 2013-02-21 | 2016-03-22 | S.P.C.M. Sa | Process for low-concentration, inverse emulsion polymerization of weakly neutralized polymers |
US9963532B2 (en) | 2013-02-21 | 2018-05-08 | S.P.C.M. Sa | Low-concentration, inverse emulsion obtained by polymerization of weakly neutralized polymers |
WO2015052426A1 (en) | 2013-10-07 | 2015-04-16 | S.P.C.M. Sa | Use in cosmetics of polymers obtained by low-concentration, inverse emulsion polymerisation with a low level of neutralised monomers |
US10561597B2 (en) | 2013-10-07 | 2020-02-18 | S.P.C.M. Sa | Use in cosmetics of polymers obtained by low-concentration, inverse emulsion polymerisation with a low level of neutralised monomers |
US10844321B2 (en) | 2014-07-23 | 2020-11-24 | The Procter & Gamble Company | Treatment compositions |
US11306275B2 (en) | 2014-07-23 | 2022-04-19 | The Procter & Gamble Company | Treatment compositions |
US10407646B2 (en) | 2014-07-23 | 2019-09-10 | The Procter & Gamble Company | Treatment compositions |
US11643618B2 (en) | 2014-07-23 | 2023-05-09 | The Procter & Gamble Company | Treatment compositions |
US10519402B2 (en) | 2014-07-23 | 2019-12-31 | The Procter & Gamble Company | Treatment compositions |
US10538719B2 (en) | 2014-07-23 | 2020-01-21 | The Procter & Gamble Company | Treatment compositions |
US10266792B2 (en) | 2014-07-23 | 2019-04-23 | The Procter & Gamble Company | Treatment compositions |
US10626351B2 (en) | 2014-07-23 | 2020-04-21 | The Procter & Gamble Company | Treatment compositions |
US10676693B2 (en) | 2014-07-23 | 2020-06-09 | The Procter & Gamble Company | Treatment compositions |
US10723975B2 (en) | 2014-07-23 | 2020-07-28 | The Procter & Gamble Company | Treatment compositions |
US10407649B2 (en) | 2014-08-06 | 2019-09-10 | S.P.C.P. Sa | Use in detergent compositions of polymers obtained by low-concentration reverse emulsion polymerization with a low content of neutralized monomers |
US11135103B2 (en) | 2014-11-06 | 2021-10-05 | The Procter & Gamble Company | Apertured webs and methods for making the same |
US10357410B2 (en) | 2014-11-06 | 2019-07-23 | The Procter & Gamble Company | Pre-strained laminates and methods for making the same |
US11324645B2 (en) | 2014-11-06 | 2022-05-10 | The Procter & Gamble Company | Garment-facing laminates and methods for making the same |
US11633311B2 (en) | 2014-11-06 | 2023-04-25 | The Procter & Gamble Company | Patterned apertured webs |
US11766367B2 (en) | 2014-11-06 | 2023-09-26 | The Procter & Gamble Company | Patterned apertured webs |
US11813150B2 (en) | 2014-11-06 | 2023-11-14 | The Procter & Gamble Company | Patterned apertured webs |
US11998431B2 (en) | 2014-11-06 | 2024-06-04 | The Procter & Gamble Company | Patterned apertured webs |
US10689600B2 (en) | 2016-01-25 | 2020-06-23 | The Procter & Gamble Company | Treatment compositions |
US11261402B2 (en) | 2016-01-25 | 2022-03-01 | The Procter & Gamble Company | Treatment compositions |
US11213436B2 (en) | 2017-02-16 | 2022-01-04 | The Procter & Gamble Company | Substrates having repeating patterns of apertures for absorbent articles |
WO2019016334A1 (en) | 2017-07-21 | 2019-01-24 | Basf Se | A process for obtaining a polymer based on anionic or nonionic monomers with an at least bimodal molecular weight distribution |
WO2019016336A1 (en) | 2017-07-21 | 2019-01-24 | Basf Se | Polymer based on anionic or nonionic monomers with an at least bimodal molecular weight distribution |
Also Published As
Publication number | Publication date |
---|---|
BRPI0509659B8 (en) | 2021-05-25 |
US20160367466A1 (en) | 2016-12-22 |
JP2012102339A (en) | 2012-05-31 |
KR20070004813A (en) | 2007-01-09 |
KR101239147B1 (en) | 2013-03-07 |
JP4989458B2 (en) | 2012-08-01 |
JP2007531811A (en) | 2007-11-08 |
BRPI0509659B1 (en) | 2019-01-29 |
WO2005097834A3 (en) | 2006-03-02 |
BRPI0509659A (en) | 2007-10-09 |
CN101671407A (en) | 2010-03-17 |
US20080275138A1 (en) | 2008-11-06 |
BRPI0509659A8 (en) | 2018-02-06 |
CN101671407B (en) | 2014-04-30 |
DE602005015704D1 (en) | 2009-09-10 |
EP1756168A2 (en) | 2007-02-28 |
ES2329488T3 (en) | 2009-11-26 |
EP1756168B1 (en) | 2009-07-29 |
ATE437896T1 (en) | 2009-08-15 |
CN1964993A (en) | 2007-05-16 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP1756168B1 (en) | Liquid dispersion polymer compositions, their preparation and their use | |
AU770521B2 (en) | Liquid dispersion polymer compositions, their preparation and their use | |
US6833406B1 (en) | Liquid dispersion polymer compositions, their preparation and their use | |
JP5323954B2 (en) | NOVEL POWDER POLYMER, METHOD FOR PREPARING THE SAME, AND METHOD OF USE AS A THINKING AGENT | |
JP2011051990A (en) | Novel concentrated inverse latex, production method and use thereof in industry | |
US6099829A (en) | Using W/O emulsions as thickeners in cosmetic and pharmaceutical formulations | |
US20190209453A1 (en) | Use in cosmetics of polymers obtained by low-concentration, inverse emulsion polymerisation with a low level of neutralised monomers | |
JP4763229B2 (en) | Self-reversible reversed-phase microlatex composition and cosmetics | |
MXPA06011126A (en) | Liquid dispersion polymer compositions, their preparation and their use | |
MXPA01010045A (en) | Liquid dispersion polymer compositions, their preparation and their use | |
KR20140009213A (en) | Novel cationic thickeners usable over a wide ph range, method for the preparation thereof, and composition containing same |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AK | Designated states |
Kind code of ref document: A2 Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BW BY BZ CA CH CN CO CR CU CZ DE DK DM DZ EC EE EG ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NA NI NO NZ OM PG PH PL PT RO RU SC SD SE SG SK SL SM SY TJ TM TN TR TT TZ UA UG US UZ VC VN YU ZA ZM ZW |
|
AL | Designated countries for regional patents |
Kind code of ref document: A2 Designated state(s): BW GH GM KE LS MW MZ NA SD SL SZ TZ UG ZM ZW AM AZ BY KG KZ MD RU TJ TM AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IS IT LT LU MC NL PL PT RO SE SI SK TR BF BJ CF CG CI CM GA GN GQ GW ML MR NE SN TD TG |
|
121 | Ep: the epo has been informed by wipo that ep was designated in this application | ||
WWE | Wipo information: entry into national phase |
Ref document number: 2005743005 Country of ref document: EP |
|
WWE | Wipo information: entry into national phase |
Ref document number: PA/a/2006/011126 Country of ref document: MX |
|
WWE | Wipo information: entry into national phase |
Ref document number: 11547214 Country of ref document: US |
|
WWE | Wipo information: entry into national phase |
Ref document number: 1020067020606 Country of ref document: KR |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2007506767 Country of ref document: JP Ref document number: 3699/CHENP/2006 Country of ref document: IN |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
WWW | Wipo information: withdrawn in national office |
Ref document number: DE |
|
WWE | Wipo information: entry into national phase |
Ref document number: 200580018523.8 Country of ref document: CN |
|
WWP | Wipo information: published in national office |
Ref document number: 1020067020606 Country of ref document: KR |
|
WWP | Wipo information: published in national office |
Ref document number: 2005743005 Country of ref document: EP |
|
ENP | Entry into the national phase |
Ref document number: PI0509659 Country of ref document: BR |