CA1255690A - Organosiloxanes utilises comme cosmetique et ecran solaire - Google Patents

Organosiloxanes utilises comme cosmetique et ecran solaire

Info

Publication number: CA1255690A
Authority: CA; Canada
Prior art keywords: group; general formula; organosiloxane; organosiloxanes; carbon
Prior art date: 1985-03-06
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA000475816A

Other languages

English (en)

Inventor

Michael P.L. Hill

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

Dow Silicones Corp

Original Assignee

Dow Corning Corp

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1985-03-06

Filing date

1985-03-06

Publication date

1989-06-13

1985-03-06 Application filed by Dow Corning Corp filed Critical Dow Corning Corp

1985-03-06 Priority to CA000475816A priority Critical patent/CA1255690A/fr

1989-06-13 Application granted granted Critical

1989-06-13 Publication of CA1255690A publication Critical patent/CA1255690A/fr

Status Expired legal-status Critical Current

Links

125000005375 organosiloxane group Chemical group 0.000 title claims abstract description 32
239000000516 sunscreening agent Substances 0.000 title claims abstract description 8
239000002537 cosmetic Substances 0.000 title description 5
238000000034 method Methods 0.000 claims abstract description 21
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 9
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 9
229910052799 carbon Inorganic materials 0.000 claims abstract description 9
239000001301 oxygen Substances 0.000 claims abstract description 9
229910052760 oxygen Inorganic materials 0.000 claims abstract description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 8
239000001257 hydrogen Substances 0.000 claims abstract description 8
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
238000002360 preparation method Methods 0.000 claims abstract description 8
125000003118 aryl group Chemical group 0.000 claims abstract description 6
125000001931 aliphatic group Chemical group 0.000 claims abstract description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 5
125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
239000000203 mixture Substances 0.000 claims description 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
238000006243 chemical reaction Methods 0.000 claims description 10
125000004432 carbon atom Chemical group C* 0.000 claims description 6
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
230000000475 sunscreen effect Effects 0.000 claims description 4
230000001476 alcoholic effect Effects 0.000 claims description 3
150000001875 compounds Chemical class 0.000 claims description 3
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 2
125000001183 hydrocarbyl group Chemical group 0.000 claims 1
239000003444 phase transfer catalyst Substances 0.000 claims 1
-1 siloxanes Chemical class 0.000 abstract description 14
230000005855 radiation Effects 0.000 abstract description 5
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract description 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
238000004519 manufacturing process Methods 0.000 abstract 1
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
239000000047 product Substances 0.000 description 11
239000000376 reactant Substances 0.000 description 11
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
230000008033 biological extinction Effects 0.000 description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
CGOJOQBYEAVATL-UHFFFAOYSA-N 3-(4-methoxyphenyl)prop-2-enoyl chloride Chemical compound COC1=CC=C(C=CC(Cl)=O)C=C1 CGOJOQBYEAVATL-UHFFFAOYSA-N 0.000 description 5
238000007792 addition Methods 0.000 description 5
229920001577 copolymer Polymers 0.000 description 5
KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 5
239000007788 liquid Substances 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
239000000243 solution Substances 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
238000010992 reflux Methods 0.000 description 4
WOGITNXCNOTRLK-VOTSOKGWSA-N (e)-3-phenylprop-2-enoyl chloride Chemical compound ClC(=O)\C=C\C1=CC=CC=C1 WOGITNXCNOTRLK-VOTSOKGWSA-N 0.000 description 3
HNVRRHSXBLFLIG-UHFFFAOYSA-N 3-hydroxy-3-methylbut-1-ene Chemical compound CC(C)(O)C=C HNVRRHSXBLFLIG-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
150000002430 hydrocarbons Chemical group 0.000 description 3
150000002500 ions Chemical class 0.000 description 3
239000000463 material Substances 0.000 description 3
239000003921 oil Substances 0.000 description 3
229910052697 platinum Inorganic materials 0.000 description 3
239000002904 solvent Substances 0.000 description 3
BYDRTKVGBRTTIT-UHFFFAOYSA-N 2-methylprop-2-en-1-ol Chemical compound CC(=C)CO BYDRTKVGBRTTIT-UHFFFAOYSA-N 0.000 description 2
KCMITHMNVLRGJU-CMDGGOBGSA-N Allyl cinnamate Chemical compound C=CCOC(=O)\C=C\C1=CC=CC=C1 KCMITHMNVLRGJU-CMDGGOBGSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
206010042496 Sunburn Diseases 0.000 description 2
ACIAHEMYLLBZOI-ZZXKWVIFSA-N Unsaturated alcohol Chemical compound CC\C(CO)=C/C ACIAHEMYLLBZOI-ZZXKWVIFSA-N 0.000 description 2
239000000370 acceptor Substances 0.000 description 2
XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
235000011187 glycerol Nutrition 0.000 description 2
150000008282 halocarbons Chemical group 0.000 description 2
BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
229920001519 homopolymer Polymers 0.000 description 2
CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 2
125000005358 mercaptoalkyl group Chemical group 0.000 description 2
150000003961 organosilicon compounds Chemical class 0.000 description 2
239000012071 phase Substances 0.000 description 2
229920000642 polymer Polymers 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
239000000126 substance Substances 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
239000000758 substrate Substances 0.000 description 2
238000005406 washing Methods 0.000 description 2
LZDXRPVSAKWYDH-UHFFFAOYSA-N 2-ethyl-2-(prop-2-enoxymethyl)propane-1,3-diol Chemical compound CCC(CO)(CO)COCC=C LZDXRPVSAKWYDH-UHFFFAOYSA-N 0.000 description 1
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
AOOGNPSUQVRFMF-UHFFFAOYSA-N 3,5-dimethylhex-1-en-3-ol Chemical compound CC(C)CC(C)(O)C=C AOOGNPSUQVRFMF-UHFFFAOYSA-N 0.000 description 1
JTWOSPUWOVJQHH-UHFFFAOYSA-N 3-prop-2-enoxypropan-1-ol Chemical compound OCCCOCC=C JTWOSPUWOVJQHH-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
FUGYGGDSWSUORM-UHFFFAOYSA-N 4-hydroxystyrene Chemical compound OC1=CC=C(C=C)C=C1 FUGYGGDSWSUORM-UHFFFAOYSA-N 0.000 description 1
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
239000002253 acid Substances 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
230000002730 additional effect Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000003342 alkenyl group Chemical group 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
125000004103 aminoalkyl group Chemical group 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
238000003287 bathing Methods 0.000 description 1
235000013871 bee wax Nutrition 0.000 description 1
239000012166 beeswax Substances 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 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
150000001728 carbonyl compounds Chemical class 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
229960000541 cetyl alcohol Drugs 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
WBYWAXJHAXSJNI-UHFFFAOYSA-N cinnamic acid Chemical class OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
239000008199 coating composition Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
239000006071 cream Substances 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
239000004205 dimethyl polysiloxane Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
235000019441 ethanol Nutrition 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
125000003709 fluoroalkyl group Chemical group 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000005259 measurement Methods 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
229940105132 myristate Drugs 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000002304 perfume Substances 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
229920000151 polyglycol Polymers 0.000 description 1
239000010695 polyglycol Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
230000003449 preventive effect Effects 0.000 description 1
235000013772 propylene glycol Nutrition 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
230000036647 reaction Effects 0.000 description 1
238000006462 rearrangement reaction Methods 0.000 description 1
238000009877 rendering Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910000077 silane Inorganic materials 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
TUNFSRHWOTWDNC-UHFFFAOYSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
239000002023 wood Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Landscapes

Silicon Polymers (AREA)

CA000475816A 1985-03-06 1985-03-06 Organosiloxanes utilises comme cosmetique et ecran solaire Expired CA1255690A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000475816A CA1255690A (fr)	1985-03-06	1985-03-06	Organosiloxanes utilises comme cosmetique et ecran solaire

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000475816A CA1255690A (fr)	1985-03-06	1985-03-06	Organosiloxanes utilises comme cosmetique et ecran solaire

Publications (1)

Publication Number	Publication Date
CA1255690A true CA1255690A (fr)	1989-06-13

Family

ID=4129962

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000475816A Expired CA1255690A (fr)	1985-03-06	1985-03-06	Organosiloxanes utilises comme cosmetique et ecran solaire

Country Status (1)

Country	Link
CA (1)	CA1255690A (fr)

1985
- 1985-03-06 CA CA000475816A patent/CA1255690A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2006-06-13	MKEX	Expiry

Publication	Publication Date	Title
EP0138321B1 (fr)	1989-06-14	Composés organosiliciques, leur préparation et utilisation
EP0538431B1 (fr)	1996-02-28	Organosiloxanes utilises comme agents de protection solaire
US4545980A (en)	1985-10-08	Organosiloxanes and preparation thereof
US4562278A (en)	1985-12-31	Organosilicon compounds and preparation and use thereof
US5596061A (en)	1997-01-21	Organosilicone having a carboxyl functional group thereon
US5093511A (en)	1992-03-03	Silicone type cinnamic acid derivative, preparation method thereof, uv-ray absorber, and external skin treatment agent
US5374759A (en)	1994-12-20	Silicone esters of hydroxy acid
EP0138590B1 (fr)	1987-05-06	Composés organosiliciques, leur préparation et leur emploi
US5246703A (en)	1993-09-21	Siloxy-functional cyclopolysiloxanes
US5077422A (en)	1991-12-31	Organosilicon compounds their preparation and use
US5061479A (en)	1991-10-29	Use of diorganopolysiloxanes containing a 3-benzylidene camphor functional group in cosmetics and new cosmetic compositions containing these compounds, intended for protecting the skin and hair
US3068152A (en)	1962-12-11	Sunburn preventive compositions
CA1255690A (fr)	1989-06-13	Organosiloxanes utilises comme cosmetique et ecran solaire
JP4076236B2 (ja)	2008-04-16	高純度枝分かれアルキルシルセスキオキサン液体
US5679822A (en)	1997-10-21	High purity branched phenylsiloxane fluids
US5315022A (en)	1994-05-24	Silicone type cinnamic acid derivative, preparation method thereof, UV-ray absorber, and external skin treatment agent
US4661616A (en)	1987-04-28	Benzoic and benzacrylic acid esters
US4912241A (en)	1990-03-27	Organosilicon compounds
JP3425508B2 (ja)	2003-07-14	新規な有機ケイ素化合物及びそれを配合してなる化粧料
GB2026511A (en)	1980-02-06	Siloxanes