ZA200501170B - Products with selected quaternary amino functionalsilicone elastomers - Google Patents
Products with selected quaternary amino functionalsilicone elastomers Download PDFInfo
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- ZA200501170B ZA200501170B ZA200501170A ZA200501170A ZA200501170B ZA 200501170 B ZA200501170 B ZA 200501170B ZA 200501170 A ZA200501170 A ZA 200501170A ZA 200501170 A ZA200501170 A ZA 200501170A ZA 200501170 B ZA200501170 B ZA 200501170B
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- ZA
- South Africa
- Prior art keywords
- formula
- personal care
- care product
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- Prior art date
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 title claims description 21
- 229920001971 elastomer Polymers 0.000 title description 23
- 239000000806 elastomer Substances 0.000 title description 23
- 229920001296 polysiloxane Polymers 0.000 claims description 54
- -1 siloxane chain Chemical group 0.000 claims description 34
- 230000001166 anti-perspirative effect Effects 0.000 claims description 30
- 239000003213 antiperspirant Substances 0.000 claims description 30
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
- 229920002379 silicone rubber Polymers 0.000 claims description 22
- 229930195733 hydrocarbon Natural products 0.000 claims description 21
- 239000004215 Carbon black (E152) Substances 0.000 claims description 18
- 239000002781 deodorant agent Substances 0.000 claims description 9
- 239000004205 dimethyl polysiloxane Substances 0.000 claims description 8
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 claims description 8
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Inorganic materials [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 229910018557 Si O Inorganic materials 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 238000004132 cross linking Methods 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000002453 shampoo Substances 0.000 claims description 3
- 239000000344 soap Substances 0.000 claims description 3
- 241000195940 Bryophyta Species 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 235000011929 mousse Nutrition 0.000 claims description 2
- 239000000203 mixture Substances 0.000 description 25
- 239000000463 material Substances 0.000 description 18
- 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 11
- 229940086555 cyclomethicone Drugs 0.000 description 10
- 239000012530 fluid Substances 0.000 description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 8
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 7
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 7
- 239000000499 gel Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 125000003342 alkenyl group Chemical group 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 229940008099 dimethicone Drugs 0.000 description 6
- 239000004971 Cross linker Substances 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- WYANSMZYIOPJFV-UHFFFAOYSA-L aluminum;2-aminoacetic acid;zirconium(4+);chloride;hydroxide;hydrate Chemical compound O.[OH-].[Al+3].[Cl-].[Zr+4].NCC(O)=O WYANSMZYIOPJFV-UHFFFAOYSA-L 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- ZGUQGPFMMTZGBQ-UHFFFAOYSA-N [Al].[Al].[Zr] Chemical compound [Al].[Al].[Zr] ZGUQGPFMMTZGBQ-UHFFFAOYSA-N 0.000 description 4
- 239000011149 active material Substances 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 229920013822 aminosilicone Polymers 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 125000001891 dimethoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- 230000001804 emulsifying effect Effects 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 4
- 150000004756 silanes Chemical class 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001350 alkyl halides Chemical class 0.000 description 3
- 230000003750 conditioning effect Effects 0.000 description 3
- 239000002537 cosmetic Substances 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 239000003205 fragrance Substances 0.000 description 3
- 239000003349 gelling agent Substances 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 239000007762 w/o emulsion Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- RXGUIWHIADMCFC-UHFFFAOYSA-N 2-Methylpropyl 2-methylpropionate Chemical compound CC(C)COC(=O)C(C)C RXGUIWHIADMCFC-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- 239000004471 Glycine Substances 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- 239000004909 Moisturizer Substances 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N ethylene glycol monomethyl ether acetate Natural products COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 238000006459 hydrosilylation reaction Methods 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 230000001333 moisturizer Effects 0.000 description 2
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 2
- SJWFXCIHNDVPSH-UHFFFAOYSA-N octan-2-ol Chemical compound CCCCCCC(C)O SJWFXCIHNDVPSH-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229920006136 organohydrogenpolysiloxane Polymers 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 238000010008 shearing Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 239000003981 vehicle Substances 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- IBLKWZIFZMJLFL-UHFFFAOYSA-N 1-phenoxypropan-2-ol Chemical compound CC(O)COC1=CC=CC=C1 IBLKWZIFZMJLFL-UHFFFAOYSA-N 0.000 description 1
- RMFFCSRJWUBPBJ-UHFFFAOYSA-N 15-hydroxypentadecyl benzoate Chemical compound OCCCCCCCCCCCCCCCOC(=O)C1=CC=CC=C1 RMFFCSRJWUBPBJ-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 1
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 1
- XXBAQTDVRLRXEV-UHFFFAOYSA-N 3-tetradecoxypropan-1-ol Chemical compound CCCCCCCCCCCCCCOCCCO XXBAQTDVRLRXEV-UHFFFAOYSA-N 0.000 description 1
- 241000252203 Clupea harengus Species 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- RGMZNZABJYWAEC-UHFFFAOYSA-N Methyltris(trimethylsiloxy)silane Chemical compound C[Si](C)(C)O[Si](C)(O[Si](C)(C)C)O[Si](C)(C)C RGMZNZABJYWAEC-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000004264 Petrolatum Substances 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 235000019484 Rapeseed oil Nutrition 0.000 description 1
- 241001125046 Sardina pilchardus Species 0.000 description 1
- 229910008051 Si-OH Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910006358 Si—OH Inorganic materials 0.000 description 1
- 101150078557 Slc36a2 gene Proteins 0.000 description 1
- ADANNTOYRVPQLJ-UHFFFAOYSA-N [dimethyl(trimethylsilyloxy)silyl]oxy-[[dimethyl(trimethylsilyloxy)silyl]oxy-dimethylsilyl]oxy-dimethylsilane Chemical compound C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C ADANNTOYRVPQLJ-UHFFFAOYSA-N 0.000 description 1
- YFCGDEUVHLPRCZ-UHFFFAOYSA-N [dimethyl(trimethylsilyloxy)silyl]oxy-dimethyl-trimethylsilyloxysilane Chemical compound C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C YFCGDEUVHLPRCZ-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- YCLAMANSVUJYPT-UHFFFAOYSA-L aluminum chloride hydroxide hydrate Chemical compound O.[OH-].[Al+3].[Cl-] YCLAMANSVUJYPT-UHFFFAOYSA-L 0.000 description 1
- 229940053431 aluminum sesquichlorohydrate Drugs 0.000 description 1
- 229940048496 aluminum zirconium pentachlorohydrex gly Drugs 0.000 description 1
- 229940048506 aluminum zirconium tetrachlorohydrex gly Drugs 0.000 description 1
- 229940072028 aluminum zirconium trichlorohydrex gly Drugs 0.000 description 1
- YXZZLAMCXFHTTE-UHFFFAOYSA-N aluminum;propane-1,2-diol;trihypochlorite;hydrate Chemical compound O.[Al+3].Cl[O-].Cl[O-].Cl[O-].CC(O)CO YXZZLAMCXFHTTE-UHFFFAOYSA-N 0.000 description 1
- 229940072049 amyl acetate Drugs 0.000 description 1
- PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229940007550 benzyl acetate Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- DSVRVHYFPPQFTI-UHFFFAOYSA-N bis(ethenyl)-methyl-trimethylsilyloxysilane;platinum Chemical compound [Pt].C[Si](C)(C)O[Si](C)(C=C)C=C DSVRVHYFPPQFTI-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000008278 cosmetic cream Substances 0.000 description 1
- 239000008341 cosmetic lotion Substances 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- LVYZJEPLMYTTGH-UHFFFAOYSA-H dialuminum chloride pentahydroxide dihydrate Chemical compound [Cl-].[Al+3].[OH-].[OH-].[Al+3].[OH-].[OH-].[OH-].O.O LVYZJEPLMYTTGH-UHFFFAOYSA-H 0.000 description 1
- KNXDJTLIRRQLBE-UHFFFAOYSA-H dialuminum;propane-1,2-diol;chloride;pentahydroxide;hydrate Chemical compound O.[OH-].[OH-].[OH-].[OH-].[OH-].[Al+3].[Al+3].[Cl-].CC(O)CO KNXDJTLIRRQLBE-UHFFFAOYSA-H 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 229940028356 diethylene glycol monobutyl ether Drugs 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- FBZANXDWQAVSTQ-UHFFFAOYSA-N dodecamethylpentasiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C FBZANXDWQAVSTQ-UHFFFAOYSA-N 0.000 description 1
- 229940087203 dodecamethylpentasiloxane Drugs 0.000 description 1
- DLAHAXOYRFRPFQ-UHFFFAOYSA-N dodecyl benzoate Chemical compound CCCCCCCCCCCCOC(=O)C1=CC=CC=C1 DLAHAXOYRFRPFQ-UHFFFAOYSA-N 0.000 description 1
- 239000003974 emollient agent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229940093499 ethyl acetate Drugs 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 229940093858 ethyl acetoacetate Drugs 0.000 description 1
- 239000010685 fatty oil Substances 0.000 description 1
- 239000000295 fuel oil Substances 0.000 description 1
- 229910021485 fumed silica Inorganic materials 0.000 description 1
- 235000014198 functional gum Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 1
- 235000019514 herring Nutrition 0.000 description 1
- NFVSFLUJRHRSJG-UHFFFAOYSA-N hexadecamethylheptasiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C NFVSFLUJRHRSJG-UHFFFAOYSA-N 0.000 description 1
- HTDJPCNNEPUOOQ-UHFFFAOYSA-N hexamethylcyclotrisiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O1 HTDJPCNNEPUOOQ-UHFFFAOYSA-N 0.000 description 1
- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical class ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 229910001867 inorganic solvent Inorganic materials 0.000 description 1
- 239000003049 inorganic solvent Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-M isovalerate Chemical compound CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- HMMGMWAXVFQUOA-UHFFFAOYSA-N octamethylcyclotetrasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 HMMGMWAXVFQUOA-UHFFFAOYSA-N 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
- ADGFKRMKSIAMAI-UHFFFAOYSA-L oxygen(2-);zirconium(4+);chloride;hydroxide Chemical compound [OH-].[O-2].[Cl-].[Zr+4] ADGFKRMKSIAMAI-UHFFFAOYSA-L 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 238000010951 particle size reduction Methods 0.000 description 1
- 229940032051 peg-8 distearate Drugs 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 229940116987 ppg-3 myristyl ether Drugs 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 235000019512 sardine Nutrition 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000004945 silicone rubber Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229940008424 tetradecamethylhexasiloxane Drugs 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- OTOIBUHBRMYFLY-UHFFFAOYSA-N trimethyl-[(2,4,4,6,6-pentamethyl-1,3,5,2,4,6-trioxatrisilinan-2-yl)oxy]silane Chemical compound C[Si](C)(C)O[Si]1(C)O[Si](C)(C)O[Si](C)(C)O1 OTOIBUHBRMYFLY-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 239000010698 whale oil Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Description
PRODUCTS WITH SELECTED QUATERNARY
AMINO FUNCTIONAL SILICONE ELASTOMERS
Field of the Invention - 5
This invention relates to personal care products made with a new type of elastomer.
There is a substantial body of literature describing various types of elastomers and their uses in cosmetic products such as face creams, make-up and antiperspirants/deodorants.
U. S. Patent 4,980,167 to Dow Corning Toray Silicone Company, Ltd.
Describes a cosmetic composition with excellent lubricity made with silicone rubber powder containing 0.50-80 wt % of silicone oil. A smooth and moist texture is obtained.
U. S. Patent 5,599,533 to Estee Lauder Inc. describes a stable water-in-oil emulsion system formed of an organopolysiloxane elastomer, a vehicle in which the elastomer is dispersed or dispersible, a stabilizing agent, a surfactant and an aqueous component and a process for forming the stable water-in-oil emulsion. The stabilized water-in-oil emulsion is useful in personal care products.
U. S. Patent 5,760,116 to General Electric Co. describes elastomer gels : containing volatile, low molecular weight silicones and comprising the hydrosilylation addition product of a linear alkenyl functionalized polyorganosiloxane and an M” Q resin and a low molecular weight silicone when subjected to shearing provides for components in personal care formulations that have improved spreadability and substance.
U. S. Patent 5,833,973 to Chesebrough Pond's USA teaches a skin treatment ‘ composition is provided which includes a crosslinked non-emulsifying siloxane elastomer, a volatile siloxane and at least 50% by weight of water. Inclusion of the ' elastomer provides a unique liquid/powdery feel when rubbed into the skin. \
® WO 2004010967 PCT/US2003/023807 : U.S. Patent 5,849,314 to Chesebrough-Pond's USA teaches a skin treatment composition comprising a crosslinked non-emulsifying siloxane elastomer, a skin conditioning agent, a volatile siloxane and no more than 5% water. Hydrocarbons such as petrolatum and polyols such as glycerin are the preferred skin conditioning agents.
Inclusion of the elastomer provides a non-traditional smooth/silky feel to the skin upon application with a non-draggy rub in.
U. S. Patent 5.929,162 to General Electric Co. teaches a composition comprising the hydrosilylation addition product of a linear alkenyl functionalized polyorganosiloxane and an MHQ resin and a low molecular weight silicone subjected to anew particle size reduction process that includes flow induced shearing and provides for components in personal care formulations that have improved spreadability and substance as a consequence of a unique particle size distribution.
U. S. Patent 5,922,308 to Chesebrough-Pond's USA describes an underarm treatment composition including a deodorant and/or antiperspirant active, a crosslinked non-emulsifying siloxane elastomer and a volatile siloxane. The compositions were found not to undergo syneresis. They also have improved efficacy, faster absorption, anti-whitening and other properties.
U.S. Patent 5,942,215 to Helene Curtis Inc describes an antiperspirant stick composition suitable for topical application to human skin, comprising: an effective amount of an antiperspirant astringent; a volatile silicone; a structurant; and a cross- linked or partially cross-linked non-emulsifying siloxane elastomer. - U.S. Patent 6,060,546 to General Electric Co. describes a non-aqueous silicone emulsion containing a silicone phase and an organic phase which is useful as a component in various personal care compositions. The silicone phase contains a crosslinked silicone elastomer and a low molecular weight silicone fluid and the organic phase contains an organic liquid.
It is an object of the present invention to provide a variety of cosmetic applications including, but not limited to, hair care products, underarm products, and cosmetic creams and lotions made with a new type of elastomer which provides better skin feel. The improvement to such products by the use of these elastomers is to provide improved skin substantivity for silicones which improves moisturization and/or conditioning. :
®
Brief Summary of the Invention oo
This invention comprises personal care products such as antiperspirants and/or ! deodorants; hair care products such as shampoos, hair conditioners, 2-in-1 shampoo/conditioner products, hair styling aids (sprays, gels, mousses); body lotions; ’ 5 make-up compositions (moisturizers, foundations, face creams); liquid soaps; bars; and shower gels. Such personal care products may be improved or restructured by the use of certain quaternary silicone elastomers as described herein.
For purposes of this invention, the quaternary amino functional silicone elastomer (especially in paste form) useful in this invention is of the type prepared by a crosslinking reaction among (1) a partially reduced organohydrogen polysiloxane copolymer of Formula III, below; and one or both of (2) an alkenyl functional silicone gum of Formula IV, below; and (3) an alkeny] terminated polysiloxane of Formula V, . below, all in the presence of a volatile and/or non-volatile silicone fluid and a platinum catalyst. Some of these reactions may be found in the art. This initial reaction is followed by a reaction with an alkoxy terminated quaternary amino polysiloxane of
Formula VII. The cross-linked silicone gel is swollen in volatile and/or non-volatile silicone fluid. It can be further subjected to high shear force in order to obtain a silicone paste. Since the quaternized silicone elastomer is made in some type of vehicle, it may be prepared containing 50 - 98 weight % (particularly 70-98%) of volatile and/or non- volatile silicone fluid to give a product with a wide range of viscosities such as in the range of 10,000-500,000 (for example, 50,000 — 500,000) centipoise (“cps”) as measured by using Brookfield viscometer, LV or RV models. This elastomer paste can be further diluted to a concentration of 2-25 weight % in an emulsion or suspension as ~~ desired for use in specific formulations. Personal care products can be formulated by combining the emulsified silicone elastomers of this invention with other ingredients.
In formulating products that are emulsions, an aqueous solution may be added to the material of Formula I in combination with cyclomethicone, hydrocarbons and . surfactants. A stable emulsion of silicone elastomer can thus be obtained with a wide range of viscosities such as in the range of 50,000 - 500,000 cps (for example, 50,000- : 30 200,000). Personal care products can be formulated by the addition of different ingredients in either the aqueous phase or the organic phase.
In formulating products that are suspensions, the material of Formula I may be used as a thickening agent to prevent precipitation of solid particles. :
This invention comprises personal care products made with this new type of silicone elastomer. The new elastomer is comprised of multiple units which may be the same or different for which each unit is a quaternary amino functional silicone elastomer of Formula I:
R? R® R° R® to | . i.
R2-Si-O-[(R*);Si-0-1,-[Si-O-)»-[Si-0-1-5i -R rR? R QY R® (0) :
R rR? | Qr RS | PE
R2-8i-0-[(R"):Si-0-L:~[Si-O-]p-[Si-O-] -Si-R : 1, TLL Le : Formula I where:
R!, R% R3, R* R’ RS R7 and RS may be the same or different and are each independently selected from the group consisting of C1-C10 monovalent hydrocarbon radicals (preferably from the group consisting of methyl, ethyl, propyl, isopropyl, and n- butyl; and most preferably methyl);
R is a divalent hydrocarbon radical of formula ~(CHz); - where s is a number in the range of 2-10 (particularly 2-8) and R is preferably -CH»-CHa-; a = is an average value and is a number in the range of 0-500 (particularly 10-150); b = is an average value and is a number in the range of 1-150 (particularly 1-15); ¢ =is an average value and is a number in the range of 1-50 (particularly 1-5); provided that b+ c is a number in the range of 2-200 (particularly 2-30);
o
Q is a siloxane chain selected from the group consisting of Q!* as shown in Formula
VA and Q'® as shown in Formula VB; and ' QV is a quaternary amino polysiloxane pendent group having quaternary nitrogen , groups and represented by Formula VIII.
The units of Formula I are crosslinked at structure Q to create an elastomer of the selected molecular weight. In particular, the average molecular weight of the material of Formula I should be in the range of 50,000- 650,000, preferably 70,000 — 200,000, and especially 100,000 daltons. One source of quaternized elastomers of
Formula I is Reliance Silicones (India) Limited. | One way of describing the elastomer is describing a particular method of making compounds of Formula I (also referred to herein as quaternized silicone elastomers). The starting material is an organohydrogen polysiloxane copolymer of
Formula II (which may be obtained from a supplier such as either from Reliance : Silicones (India) Limited or Petrarch Systems Silanes & Silicones (a subsidiary of
United Chemical Technologies, Sugarland, TX) and also referred to herein as a methyl hydrogen polysiloxane copolymer ("MHPS copolymer”).
R! H R®
RUAN NS pv
R2-Si-O-[(RM)2810-]4-[Si-0-14-Si-R 0 lL
Formula II where:
RR? R3, RY, RS, RR? and R® may be the same or different and are each independently selected from the group consisting of C1-C10 monovalent hydrocarbon radicals (particularly selected from the group consisting of methyl, ethyl, propyl, and isopropyl, and most preferably selected to be methyl groups); d is a number equal to b + ¢ (which is a number in the range of 2-200); a, previously defined as a number in the range of 0-500.
More particular examples of copolymers of Formula II are those in which a and d are selected so that the material of Formula II has an average molecular weight in the range of 1,000-50,000.
@
The material of Formula II is partially reduced by using platinum - divinyl tetramethyldisiloxane complex in cyclomethicone (such as D4 or Ds) er dimethicone (such as a 350 centistoke material) to partially convert the Si-H groups of Formula I material to Si-OEL This gives a material of Formula IIL.
R! H OH R®
RS ORIOL {0-1 S10-1c - SR ek kk
Formula III
More cyclomethicone (particularly if an underarm product is being made later) or dimethicone (particularly if a hair care, skin cleanser or skin moisturizer is being made later) is added with at least one crosslinker selected from the group consisting of (a) an alkenyl functional gum of Formula IV:
R® RY RY '
R'. SOIR, SIO [- 510-1, SLR 1, Ly La ~~ Formula IV where, m and p are selected so that the molecular weight of the material of Formula IV is in the range of 100,000-900,000, particularly 300,000 - 600,000;
R'%,R" and R'® may be the same or different and are each independently selected from the group consisting of C2-C10 monovalent hydrocarbon radicals having an unsaturation at the terminal carbon (that is, an allyl or vinyl group, preferably vinyl);
R%, RY, R'?, R™ R' and RY may be the same or different and are each independently selected from the group consisting of C1 to C10 monovalent hydrocarbon radicals (preferably, methyl, ethyl, propyl, isopropyl; most preferably methyl). Note that for R!3 in Formula IV, additional crosslinking may take place at this reactive alkenyl site so that a three dimensional structure is created via the reaction of the terminal unsaturated bond of R*® , however, the sites where R'® and R'® are located will react first.
Materials of Formula IV may also be obtained from Petrarch Systems Silanes &
Silicones.
® (b) an alkenyl terminated polysiloxane of Formula V: ‘ RS rR
RY - SL OLR, 5i-0-) dr 2 Re
Formula V where: r is an average number selected to give the material of Formula V an average viscosity in the range of 1,000-100,000 centistokes;
R', R% may be the same or different and are each independently selected from the group consisting of C2-C10 monovalent unsaturated hydrocarbon radicals having 2 to 10 carbon atoms with an unsaturation at the terminal carbon (that is an allyl or vinyl group, preferably vinyl); and
R!® R2 R? R? and R* may be the same or different and are each independently selected from the group consisting of C1 to C10 monovalent hydrocarbon radicals (preferably selected from the group consisting of methyl, ethyl, propyl, isopropyl, and most preferably selected to be methyl) (Materials of Formula V may also be obtained from Petrarch Systems Silanes & Silicones or Reliance Silicones.); and (c) mixtures of (a) and (b), particularly where the ratio of (a): (b) is in the range of 1:20-1:50, and more particularly with a ratio of 1:30. ) In these definitions the use of a cross linker of Formula IV will give Q' the following structure:
Rr RM RY
I
— Si~O[(RY),Si0-}n-[-Si-0-1,-Si-—- he bs fos ' Formula VA and the use of a crosslinker of Formula V will give Q'® the following structure:
RS RA n : — Si-O[(R"");-8i-0-]; -Si—
R R*
Formula VB
The vinyl-terminated polysiloxane of Formula V can be obtained from Reliance
Silicones (India) Limited or Petrarch Systems Silanes & Silicones.
The mixture of the material of Formula III with the crosslinker (one or more crosslinkers) is homogenized with heating under conventional conditions in the presence of cyclomethicone (or dimethicone) and a platinum catalyst, until the mixture gels. This gelled material, in general, may be represented by Formula VL
R! I R® R® [
R2-Si-0-[(R*)2Si-0-1s-[Si-O-1,-[Si-0-1-Si -R’ [
R R OH R
Q
R
R' | OH R® | . I
R*-Si-O-[(R*),8i-0-1,-[Si-O-}y-[Si-O-]¢ -Si-R 1, LoL 1
Formula VI with preferred values for R!, R% R?, R%, R®, R®, R7and R® being methyl; and values for
R and Q being the same as described in Formula L
To make the quaternary product more cyclomethicone (or dimethicone) is added with homogenization and further reaction is carried out with a reactive quaternary silicone such as a dialkoxy (preferably dimethoxy or diethoxy) terminated quaternary
® amino silicone of Formula VII:
R*0 - OR*
RE en ==(Q") J
J > | - 30
R*0O OR :
Formula VII where:
R¥, R®, R?, R%, R? and R* may be the same or different and are each independently selected from the group consisting of C1-C10 monovalent hydrocarbon radicals (preferably from the group consisting of methyl, ethyl, propyl, isopropyl; most preferably methyl);
Q' is a quaternary amino functional polydimethylsiloxane such as
R32 ~[(OSiR*)2);~(O -Si-)s-0-]"~
A nx’? where:
A = adi-cation of formula -(CH2)sNR>"),*CH,CH,N®R*®);*! or 2 mono-cation of formula ~(CHz)sN(R®);s* !; X'! is selected from the group consisting of CH;COO™; (SOs; (SO); CI’; T; and F? (particularly CH;COO™; I and CI); ) © R and R*? may be the same or different and are each selected from the group consisting of C1-C10 monovalent hydrocarbon radicals (preferably selected from the group consisting of methyl, ethyl, propyl, and isopropyl; and most preferably selected to be methyl); R® ,R® and R*® may be alike or different and are each independently selected from the group consisting of hydrogen, C1-C10 monovalent hydrocarbon radicals (preferably selected from the group consisting of methyl, ethyl, propyl and isopropyl; and most preferably methyl); . y is an average value and is a number in the range of 1-750; and zis an average value and is a number in the range of 1-200.
@
The dimethoxy terminated quaternary silicones of Formula VII can be made by quaternizing dimethoxy terminated amino silicone (such as dimethoxy terminated polydimethyl aminoethyl aminopropyl methylsiloxane from Shin-Etsu Silicones of
America, Akron, OH) using acetic acid, HI, HCI or an alkyl halide.
The material of Formula VII reacts at its alkoxy sites (for example, methoxy sites) with the Si-OH groups of Formula VI to give the material of Formula L. In the process of doing this, a pendent group of Formula VII is formed: 28 oO OR
Ri SEP
R70 - br?
Formula VIII which leads to the formation of the quaternary amino functional silicone elastomer of *-
Formula I described above. (Formula VIII is the same as QM). The elastomer is insoluble in volatile silicone, organic and inorganic solvents.
The amino polysiloxanes are quaternized using protonic acids (such as HCI, HI, acetic acid) or alkyl halides give quaternary amino polysiloxanes. For each of these example amines the counter ion X~ ! may be selected from the group consisting of CHs coo’, tor Crt. :
Other options for quaternary functional silicones include, (1) trialkoxy functional quaternary amino silicone (preferably trimethoxy or triethoxy); and (2) monoalkoxy functional quaternary amino silicone (preferably monomethoxy or monoethoxy). Also mono, di and tri alkoxy functional amino functional silicones may be used separately or along with quaternary functional silicones. Alkoxy or amino functionality may be present at terminal and/or within the polysiloxane chain. All these above functional silicones may be linear and or branched.
Suitable catalysts for the partial reduction step include Group VIII transition metals, preferably platinum metal, rhodium metal or their respective complexes. Such catalysts can be used separately or in a mixture.
®
Silicone fluids used in the preparation of the quaternized elastomer paste include low molecular weight linear and/or cyclic volatile silicone fluids; and branched chain volatile and non-volatile silicone fluids. In more specific terms, (a) linear volatile silicone fluids such as hexamethyldisiloxane (MM), “© 5 octamethylisiloxane, decamethyltetrasiloxane, dodecamethylpentasiloxane, tetradecamethylhexasiloxane, hexadecamethylheptasiloxane, etc. (b) cyclic volatile silicones of the general formula ((R3%);Si0); (where i < 8) (particularly hexamethylcyclotrisiloxane (Ds), octamethylcyclotetrasiloxane (Da), decamethylcyclopentasiloxane (Ds), dodecamethyicyclohexasiloxane (D)) (c) branched volatile methyl siloxanes heptamethyl-3-{ (trimethylsilyl)oxy }trisiloxane (M;5T); hexamethyl-3,3,bis{ (trimethylsilyl)oxy} trisiloxane (M4Q), pentamethyl { (trimethylsilyl)oxy }cyclotrisiloxane (MDs). (d) cyclic non-volatile silicones of the general formula ((R*),S10)j (where j 2 8). (e) linear non volatile polysiloxanes of the formula (R**)3SiO((R*)2Si0)a SiR*); having viscosity in the range of 5 - 2000 cps, where R® R* R and R* may be the same or different and are each selected from the group consisting of C1-C10 monovalent hydrocarbon radicals (preferably selected from the group consisting of methyl, ethyl, propyl, and isopropyl; and most preferably selected to be methyl) or aryl; and h defined as a number in the range of 2-500, preferably in the range of 10 — 250; more preferably 10 — 100.
Other than silicone fluids, organic compounds (mainly solvents) can also be - used to prepare the elastomer paste either separately or in the mixture form (along with silicone fluids). These include organic solvents such as alcohols (for example methanol, ethanol, 1-propanol, cyclohexanol, benzyl alcohol, 2-octanol, ethylene glycol, propylene glycol, and glycerol); aromatic hydrocarbons (for example benzene, toluene, ethylbenzene, and xylene); aliphatic hydrocarbons (for example cyclohexane," heptane); aldehydes, (for example acetaldehyde, benzaldehyde); ketones (for example : acetone, methyl ethyl ketone, cyclohexanone, diacetone alcohol, methyl amyl ketone, and diisobutyl ketone); amines (for example isopropylamine, cyclohexylamine, ethanolamine, and diethanolamine); esters (for example ethyl acetate, isopropyl acetate, ethyl acetoacetate, amyl acetate, isobutyl isobutyrate, and benzyl acetate); ethers (for example ethyl ether, n-butyl ether, tetrahydrofuran, and 1,4-dioxane; glycol ethers);
: C glycol ethers (for example ethylene glycol monomethyl ether, ethylene glycol monomethyl ether acetate, diethylene glycol monobutyl ether, and propylene glycol monophenyl ether); alkyl halides (for example chloroform, carbon tetrachloride, chlorobenzene); petroleum hydrocarbons (for example mineral oil, kerosene); gas oil, heavy oil, crude oil, lubricating oil; naturally occurring fatty oil (for example com oil, soybean oil, olive oil, rape seed oil, cotton seed oil, sardine oil, herring oil, and whale oil).
The invention includes products such as antiperspirants and/or deodorants having a formula made with at least 10 weight % of a volatile silicone. For example, if astick is desired, a gellant such as a minimum of 10 weight % stearyl alcohol or a minimum of at least 5 weight % siliconized polyamide as described in U.S. Patents
Numbers 5,919,441 and 6,051,216 (incorporated herein by reference as to their description of gelling agents) may be used. If a gel is desired, a surfactant in the range of 0.1-3 weight % is added. ,
If a gelling agent is used such such agents also include those described in U.S.
Patents Numbers 5,833,964; 5,730,963; 5,635,164; and 5,462,736, all of which are incorporated herein by reference as to their description of solidifying agents.
Examples of antiperspirants and/or deodorants include:
Gel made with
Oil phase: 17.9-69.7 weight % cyclomethicone (preferably D5) 0.1-25 weight % quaternized silicone elastomer of Formula I 2-15 weight % silicone copolyol (DC 5225C from Dow Corning Corp.) 0-20 weight % emollient 0-5 weight % fragrance
Aqueous phase: 0.1-25 weight % antiperspirant active (such as Rezal 36 GP from Reheis Corp.
Berkeley Heights, NJ; or Zr 35BX from Westwood Chemical Corp., Middletown, NJ) 20-79.9 weight % water 0-10 weight % of one or more of ethanol, propylene glycol, dipropylene glycol or tripropylene glycol
® 0-10 weight % of an organic or inorganic salt (such as sodium chloride, zinc chloride or magnesium chloride) : Stick A made with
Part 1: 10-21 weight % cyclomethicone (such as DC 345 from Dow Coming Corp, Midland
MI) 0-6 weight % PPG-3 myristyl ether . 6-11 weight % C12-15 alkyl benzoate (such as Finsolv TN from Finetex Inc., Elmwood
Park, NJ) : 18-25 weight % stearyl alcohol (from Cognis, Ambler, PA) 0-10 weight % (especially 4 %) hydrogenated castor oil (such as MP 80 from Caschem,
Bayonne, NJ) 0-10 weight % (especially 4 %) ( PEG-8 distearate (from Stepan Chemicals, Northfield,
IL) up to 10.0 weight % quaternized elastomer of Formula I
Pat2 : 15-25 weight % (especially 20 %) cyclomethicone as above 0-15 weight % (especially 5 %) dimethicone copolyol (DC 5225C from Dow Corning, 10% active in cyclomethicone) 17-25 weight % antiperspirant active (such as Reach AZP 908 from Reheis Corp.) 0-5 weight % fragrance
Soft Solid 5-70 weight % quaternized silicone elastomer of Formula I 0.1-25 weight % antiperspirant active 0-20 weight % fumed silica 0-5 weight % fragrance 0-10 weight % dimethicone copolyol (DC 5225C) : : QS cyclomethicone
For antiperspirants and deodorants the ingredients can be chosen from the ‘ 30 following.
The antiperspirant active can be selected from the group consisting of any of the known antiperspirant active materials. These include, by way of example (and not of a
@ limiting nature), aluminum chlorohydrate, aluminum chloride, aluminum sesquichlorohydrate, zirconyl hydroxychloride, aluminum-zirconium glycine complex (for example, aluminum zirconium trichlorohydrex gly, aluminum zirconium pentachlorohydrex gly, aluminum zirconium tetrachlorohydrex gly and aluminum zirconium octochlorohydrex gly), aluminum chlorohydrex PG, aluminum chlorohydrex
PEG, aluminum dichlorohydrex PG, and aluminum dichlorohydrex PEG. The aluminum-containing materials can be commonly referred to as antiperspirant active aluminum salts. Generally, the foregoing metal antiperspirant active materials are : antiperspirant active metal salts. In the embodiments which are antiperspirant compositions according to the present invention, such compositions need not include aluminum-containing metal salts, and can include other antiperspirant active materials, including other antiperspirant active metal salts. Generally, Category I active antiperspirant ingredients listed in the Food and Drug Administration's Monograph on antiperspirant drugs for over-the-counter human use can be used. In addition, any new drug, not listed in the Monograph, such as aluminum nitratohydrate and its combination with zirconyl hydroxychlorides and nitrides, or aluminum-stannous chlorohydrates, can be incorporated as an antiperspirant active ingredient in antiperspirant compositions according to the present invention.
Particular types of antiperspirant actives include aluminum zirconium trichlorohydrex and aluminum zirconium tetrachlorohydrex either with or without glycine. A particular antiperspirant active is aluminum trichlorohydrex gly such as
AZZ-902 SUF (from Reheis Inc., Berkley Heights, NJ) which has 98% of the particles less than 10 microns in size. Antiperspirant actives can be incorporated into compositions according to the present invention in amounts in the range of 0.1 — 25% of the final composition, but the amount used will depend on the formulation of the composition. For example, at amounts in the lower end of the broader range (for example, 0.1 - 10% on an actives basis), a deodorant effect may be observed. At lower levels the antiperspirant active material will not substantially reduce the flow of perspiration, but will reduce malodor, for example, by acting as an antimicrobial material. At amounts of 10-25% (on an actives basis) such as 15 - 25%, by weight, of the total weight of the composition, an antiperspirant effect may be observed.
Claims (15)
1. A personal care product selected from the group consisting of antiperspirants and/or deodorants, soaps, and hair care products and made with a quaternary amino functional silicone elastomer having a molecular weight in the range of 50,000 - 650,000 daltons and comprising units which may be the same or different wherein each unit is represented by Formula I: R! R® R® R* 0 | lo R*-Si-O-[(R*);Si-0-1,-[Si-O-1p-[Si-O-]-Si -R R} R QY R® @ R rR? | oN RS 1 lr, R*-Si-0-[(R):Si-0-1a-[Si-O-1,-[Si-O-]. -Si-R Re BORK Formula where: N R!, R% RS, RY, RP, R%, R” and R® may be the same or different and are each independently selected from the group consisting of C1-C10 monovalent hydrocarbon radicals; Ris a divalent hydrocarbon radical of formula -(CHy)s - where s is a number in the range of 2-10; a = is an average value and is a number in the range of 0-500; b = is an average value and is a number in the range of 1-150; c = is an average value and is a pumber in the range of 1-50; provided that b+ c is a number in the range of 2-200;
Q is a siloxane chain selected from the group consisting of QA of Formula VA: 1 R® RM RV c 5 - Si-O[(R?),Si0-]n-[-Si-O-1p-Si— La Lis Les Formula VA and Q" of Formula VB: RS R* : oo — Si-O[(R*")2-Si-O-]; -Si~—- rR? R® Formula VB where m is an average number with a value in the range of 2,000-10,000; pis an average number with a value in the range of 1-200; RS is selected from the group consisting of C2-C10 monovalent hydrocarbon radicals having an unsaturation at the terminal carbon which may be used as a crosslinking site at the unsaturation; . rR’, RY, RY? RY RY and R!” may be the same or different and are each independently selected from the group consisting of C1 to C10 monovalent hydrocarbon radicals; RE, R®, RY, RZ and R? may be the same or different and are each independently selected from the group consisting of C1 to C10 monovalent hydrocarbon radicals; and QV is a quaternary amino polysiloxane pendent group of Formula VIII: 0 OR*
R%.Si -reemn(Q")mn--——Si-R” R70 ORY Formula VIII
° WO 2004/010967 PCT/US2003/023807 where R?, RY. R® R? and R*® may be the same or different and are each independently selected from the group consisting of C1-C10 monovalent hydrocarbon radicals; and Q' is a quaternary amino functional polydimethylsiloxane of formula: R® ~[(OSiR*)2)y(0 -Si)-O-T"- i nx? a. where: A = a dication of formula -(CHz)sNR®”);*CH,CH;N®R*)s* or a mono-cation of formula -(CHz)sN®*®)2*; X'* is selected from the group consisting of CH,CO0™%;
(SO. (SOs); CI’; T; and F* (particularly CH,COO™; I! and CI); R>! and R3 may be the same or different and are each selected from the group consisting of C1-C10 monovalent hydrocarbon radicals; RY, R3 and R¥ may be. alike or different and are each independently selected from the group consisting of hydrogen, and C1-C10 monovalent hydrocarbon radicals.
2. A personal care product a claimed in Claim ‘1 wherein the quaternary amino functional silicone elastomer of has a molecular weight in the range of 70,000-200,000 daltons. :
3. A personal care product a claimed in Claim 1 wherein the quaternary amino functional silicone elastomer has each of R!,R* R% RY, R%, RS, R’ and R® as methyl.
4, A personal care product a claimed in Claim 1 wherein the quaternary amino functional silicone elastomer has each of R® RR? RM R' and RY’ as methyl.
5. A personal care product a claimed in Claim 1 wherein the quaternary amino functional silicone elastomer has each of R'®, R® R*, R®? and R? as methyl.
6. A personal care product a claimed in Claim 1 wherein the quaternary amino functional silicone elastomer has each of R*, R¥, RR” and R*® as methyl. Dy
7. A personal care product a claimed in Claim 1 wherein the quaternary amino ¢ 5 functional silicone elastomer has each of R*!, R¥, R¥ ,R*® and R® as methyl.
8. A personal care product a claimed in Claim 1 wherein the quaternary amino functional silicone elastomer has each of R!, R?, R3, R*, R%, RS, R7, R%,R® R', R%, R!4 R!S R!7 RIE R2 R2 RZ R% R26 RZ R%E Rp RP p31 R32 p37 RIF 4nd RY? as methyl.
9. A personal care product a claimed in Claim 1 which is an antiperspirant and/or deodorant comprising at least 10 weight % of a volatile silicone.
10. A personal care product a claimed in Claim 1 which is a hair care product.
11. A personal care product a claimed in Claim 1 which is a soap bar.
12. A personal care product a claimed in Claim 1 which is a shower gel.
13. A personal care product a claimed in Claim 1 which is a mousse.
14. A personal care product a claimed in Claim 1 which is a shampoo.
15. A personal care product as claimed in Claim 1 which is a hair conditioner.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US39984902P | 2002-07-31 | 2002-07-31 |
Publications (1)
Publication Number | Publication Date |
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ZA200501170B true ZA200501170B (en) | 2006-09-27 |
Family
ID=38917748
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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ZA200501170A ZA200501170B (en) | 2002-07-31 | 2005-02-09 | Products with selected quaternary amino functionalsilicone elastomers |
Country Status (3)
Country | Link |
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AR (1) | AR040754A1 (en) |
GT (1) | GT200300161A (en) |
ZA (1) | ZA200501170B (en) |
-
2003
- 2003-07-31 GT GT200300161A patent/GT200300161A/en unknown
- 2003-07-31 AR ARP030102762 patent/AR040754A1/en unknown
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2005
- 2005-02-09 ZA ZA200501170A patent/ZA200501170B/en unknown
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Publication number | Publication date |
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GT200300161A (en) | 2004-05-18 |
AR040754A1 (en) | 2005-04-20 |
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