US20030207948A1 - Emulsions containing crosslinked and non-crosslinked silicone polyethers - Google Patents
Emulsions containing crosslinked and non-crosslinked silicone polyethers Download PDFInfo
- Publication number
- US20030207948A1 US20030207948A1 US10/408,480 US40848003A US2003207948A1 US 20030207948 A1 US20030207948 A1 US 20030207948A1 US 40848003 A US40848003 A US 40848003A US 2003207948 A1 US2003207948 A1 US 2003207948A1
- Authority
- US
- United States
- Prior art keywords
- sio
- crosslinked silicone
- percent
- weight
- glycol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 229920001296 polysiloxane Polymers 0.000 title claims abstract description 45
- 229920000570 polyether Polymers 0.000 title claims abstract description 38
- 239000000839 emulsion Substances 0.000 title claims abstract description 19
- -1 polysiloxane Polymers 0.000 claims abstract description 53
- 239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 25
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims abstract description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000003054 catalyst Substances 0.000 claims abstract description 16
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 16
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 13
- 239000004064 cosurfactant Substances 0.000 claims abstract description 13
- 229920002545 silicone oil Polymers 0.000 claims abstract description 10
- 229910052697 platinum Inorganic materials 0.000 claims abstract description 9
- 150000002009 diols Chemical class 0.000 claims abstract description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 19
- 125000005702 oxyalkylene group Chemical group 0.000 claims description 17
- 229920002379 silicone rubber Polymers 0.000 claims description 12
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 7
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 6
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 6
- BPIUIOXAFBGMNB-UHFFFAOYSA-N 1-hexoxyhexane Chemical compound CCCCCCOCCCCCC BPIUIOXAFBGMNB-UHFFFAOYSA-N 0.000 claims description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 4
- 239000005977 Ethylene Substances 0.000 claims description 4
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims description 4
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 claims description 4
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 claims description 4
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims description 4
- 238000010008 shearing Methods 0.000 claims description 3
- 239000005968 1-Decanol Substances 0.000 claims description 2
- 229960000541 cetyl alcohol Drugs 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 150000001298 alcohols Chemical class 0.000 claims 1
- 150000004072 triols Chemical class 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 9
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 abstract description 4
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 abstract description 4
- 238000010438 heat treatment Methods 0.000 abstract description 2
- 230000000379 polymerizing effect Effects 0.000 abstract description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 27
- 238000009835 boiling Methods 0.000 description 13
- 150000001875 compounds Chemical class 0.000 description 12
- 229910020447 SiO2/2 Inorganic materials 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 229910000510 noble metal Inorganic materials 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 125000006353 oxyethylene group Chemical group 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- PRBHEGAFLDMLAL-UHFFFAOYSA-N 1,5-Hexadiene Natural products CC=CCC=C PRBHEGAFLDMLAL-UHFFFAOYSA-N 0.000 description 3
- 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 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical group CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 3
- 229910020388 SiO1/2 Inorganic materials 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000004205 dimethyl polysiloxane Substances 0.000 description 3
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical compound C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- XWJBRBSPAODJER-UHFFFAOYSA-N 1,7-octadiene Chemical compound C=CCCCCC=C XWJBRBSPAODJER-UHFFFAOYSA-N 0.000 description 2
- 239000004322 Butylated hydroxytoluene Substances 0.000 description 2
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 2
- 229940095259 butylated hydroxytoluene Drugs 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 2
- 238000007720 emulsion polymerization reaction Methods 0.000 description 2
- 230000001815 facial effect Effects 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- YFIBSNDOVCWPBL-UHFFFAOYSA-N hexa-1,5-diyne Chemical compound C#CCCC#C YFIBSNDOVCWPBL-UHFFFAOYSA-N 0.000 description 2
- 150000002431 hydrogen Chemical group 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- AWJFCAXSGQLCKK-UHFFFAOYSA-N icosa-1,19-diene Chemical compound C=CCCCCCCCCCCCCCCCCC=C AWJFCAXSGQLCKK-UHFFFAOYSA-N 0.000 description 2
- 239000006210 lotion Substances 0.000 description 2
- 239000004530 micro-emulsion Substances 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- VJHGSLHHMIELQD-UHFFFAOYSA-N nona-1,8-diene Chemical compound C=CCCCCCC=C VJHGSLHHMIELQD-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000002304 perfume Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
- 229940058015 1,3-butylene glycol Drugs 0.000 description 1
- 208000002874 Acne Vulgaris Diseases 0.000 description 1
- 241000195940 Bryophyta Species 0.000 description 1
- FFLOMSPVGCTWLM-UHFFFAOYSA-N C[Si](C)(C)O[SiH2]O[SiH2]O[SiH3] Chemical compound C[Si](C)(C)O[SiH2]O[SiH2]O[SiH3] FFLOMSPVGCTWLM-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- IUMSDRXLFWAGNT-UHFFFAOYSA-N Dodecamethylcyclohexasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 IUMSDRXLFWAGNT-UHFFFAOYSA-N 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- FPVVYTCTZKCSOJ-UHFFFAOYSA-N Ethylene glycol distearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCOC(=O)CCCCCCCCCCCCCCCCC FPVVYTCTZKCSOJ-UHFFFAOYSA-N 0.000 description 1
- DBVJJBKOTRCVKF-UHFFFAOYSA-N Etidronic acid Chemical compound OP(=O)(O)C(O)(C)P(O)(O)=O DBVJJBKOTRCVKF-UHFFFAOYSA-N 0.000 description 1
- 229920002907 Guar gum Polymers 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- 244000062730 Melissa officinalis Species 0.000 description 1
- 235000010654 Melissa officinalis Nutrition 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
- 239000004909 Moisturizer Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 229910007161 Si(CH3)3 Inorganic materials 0.000 description 1
- 229910020487 SiO3/2 Inorganic materials 0.000 description 1
- 229910020485 SiO4/2 Inorganic materials 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 229910002808 Si–O–Si Inorganic materials 0.000 description 1
- 229920002125 Sokalan® Polymers 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
- 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
- 239000006096 absorbing agent Substances 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 206010000496 acne Diseases 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000002528 anti-freeze Effects 0.000 description 1
- 230000001166 anti-perspirative effect Effects 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 239000003213 antiperspirant Substances 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- 150000001565 benzotriazoles Chemical class 0.000 description 1
- 239000003139 biocide Substances 0.000 description 1
- DSVRVHYFPPQFTI-UHFFFAOYSA-N bis(ethenyl)-methyl-trimethylsilyloxysilane;platinum Chemical group [Pt].C[Si](C)(C)O[Si](C)(C=C)C=C DSVRVHYFPPQFTI-UHFFFAOYSA-N 0.000 description 1
- LLCSWKVOHICRDD-UHFFFAOYSA-N buta-1,3-diyne Chemical compound C#CC#C LLCSWKVOHICRDD-UHFFFAOYSA-N 0.000 description 1
- 235000019437 butane-1,3-diol Nutrition 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
- 235000019282 butylated hydroxyanisole Nutrition 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 229940105329 carboxymethylcellulose Drugs 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001851 cinnamic acid derivatives Chemical class 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- NLDGJRWPPOSWLC-UHFFFAOYSA-N deca-1,9-diene Chemical compound C=CCCCCCCC=C NLDGJRWPPOSWLC-UHFFFAOYSA-N 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
- 239000002781 deodorant agent Substances 0.000 description 1
- 230000002951 depilatory effect Effects 0.000 description 1
- IYPLTVKTLDQUGG-UHFFFAOYSA-N dodeca-1,11-diene Chemical compound C=CCCCCCCCCC=C IYPLTVKTLDQUGG-UHFFFAOYSA-N 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
- MCPKSFINULVDNX-UHFFFAOYSA-N drometrizole Chemical compound CC1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 MCPKSFINULVDNX-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 229960001484 edetic acid Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 229940100608 glycol distearate Drugs 0.000 description 1
- 239000007952 growth promoter Substances 0.000 description 1
- 239000000665 guar gum Substances 0.000 description 1
- 235000010417 guar gum Nutrition 0.000 description 1
- 229960002154 guar gum Drugs 0.000 description 1
- 239000008266 hair spray Substances 0.000 description 1
- GEAWFZNTIFJMHR-UHFFFAOYSA-N hepta-1,6-diene Chemical compound C=CCCCC=C GEAWFZNTIFJMHR-UHFFFAOYSA-N 0.000 description 1
- 239000004009 herbicide Substances 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
- 239000005556 hormone Substances 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 125000000400 lauroyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000865 liniment Substances 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000001333 moisturizer Effects 0.000 description 1
- 235000011929 mousse Nutrition 0.000 description 1
- 125000001419 myristoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 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
- CXQXSVUQTKDNFP-UHFFFAOYSA-N octamethyltrisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C CXQXSVUQTKDNFP-UHFFFAOYSA-N 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 150000003961 organosilicon compounds Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- DXGLGDHPHMLXJC-UHFFFAOYSA-N oxybenzone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1 DXGLGDHPHMLXJC-UHFFFAOYSA-N 0.000 description 1
- QYZLKGVUSQXAMU-UHFFFAOYSA-N penta-1,4-diene Chemical compound C=CCC=C QYZLKGVUSQXAMU-UHFFFAOYSA-N 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920001921 poly-methyl-phenyl-siloxane Polymers 0.000 description 1
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229940068984 polyvinyl alcohol Drugs 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 125000005372 silanol group Chemical group 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 229920005573 silicon-containing polymer Polymers 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 239000002884 skin cream Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 125000003696 stearoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000000475 sunscreen effect Effects 0.000 description 1
- 239000000516 sunscreening agent Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- XMRSTLBCBDIKFI-UHFFFAOYSA-N tetradeca-1,13-diene Chemical compound C=CCCCCCCCCCCC=C XMRSTLBCBDIKFI-UHFFFAOYSA-N 0.000 description 1
- 229940008424 tetradecamethylhexasiloxane Drugs 0.000 description 1
- 235000015961 tonic Nutrition 0.000 description 1
- 230000001256 tonic effect Effects 0.000 description 1
- 229960000716 tonics Drugs 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- ICUTUKXCWQYESQ-UHFFFAOYSA-N triclocarban Chemical compound C1=CC(Cl)=CC=C1NC(=O)NC1=CC=C(Cl)C(Cl)=C1 ICUTUKXCWQYESQ-UHFFFAOYSA-N 0.000 description 1
- 229960001325 triclocarban Drugs 0.000 description 1
- 229960003500 triclosan Drugs 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
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 230000037303 wrinkles Effects 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
- C08J3/03—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in aqueous media
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2383/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen, or carbon only; Derivatives of such polymers
- C08J2383/04—Polysiloxanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/10—Block- or graft-copolymers containing polysiloxane sequences
- C08L83/12—Block- or graft-copolymers containing polysiloxane sequences containing polyether sequences
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/14—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
Definitions
- This invention is related to emulsions and preparing emulsions using non-crosslinked silicone polyethers and crosslinked silicone polyethers.
- emulsions containing non-crosslinked silicone polyethers and crosslinked silicone polyethers are prepared by emulsion polymerization.
- emulsions containing non-crosslinked silicone polyethers and crosslinked silicone elastomers containing no oxyalkylene units are prepared mechanically.
- the '417 patent does not teach preparing mechanical emulsions with a non-crosslinked silicone polyether in combination with a crosslinked silicone elastomer containing no oxyalkylene units, a second embodiment of the invention. Further, and in this regard, the '417 patent does not teach preparing emulsions with a non-crosslinked silicone polyether in combination with a crosslinked silicone elastomer containing no oxyalkylene units, without application of any mechanical shearing force.
- the invention is directed to a method of preparing emulsions by heating and polymerizing a mixture containing (i) a non-crosslinked silicone polyether; (ii) optionally, a cosurfactant which can be a monohydroxy alcohol, diol, triol, or glycol ether; (iii) an ⁇ Si—H containing polysiloxane; (iv) a mono-alkenyl polyether; (v) an ⁇ , ⁇ -diene, ⁇ , ⁇ -diyne, or ⁇ , ⁇ )-ene-yne; (vi) optionally, a silicone oil such as (a) a low molecular weight linear or cyclic volatile methyl siloxane, or (b) a low molecular weight linear or cyclic volatile or non-volatile alkyl or aryl siloxane; (vii) a platinum catalyst; and (viii) water.
- a cosurfactant which can be a monohydroxy alcohol, diol,
- the crosslinked silicone polyether is obtained as a result of polymerization of components (iii), (iv), and (v).
- the invention is directed to a method of making oil-in-water emulsions by mixing (i) a non-crosslinked silicone polyether; (ii) a cosurfactant such as a monohydroxy alcohol, diol, triol, or glycol ether; and (iii) water; with (iv) a crosslinked silicone elastomer containing no oxyalkylene units prepared by reacting (a) an ⁇ Si—H containing polysiloxane; (b) an ⁇ , ⁇ -diene, ⁇ , ⁇ -diyne, or ⁇ , ⁇ -ene-yne; (c) a silicone oil such as (I) a low molecular weight linear or cyclic volatile methyl siloxanes, or (II) a low molecular weight linear or cyclic volatile or non-volatile alkyl or aryl siloxane; and (d) a platinum catalyst.
- a non-crosslinked silicone polyether e.g., a co
- the invention is also directed to emulsions prepared according to the methods of each of these embodiments.
- the non-crosslinked silicone polyether is generally water soluble or water dispersible. It can have a rake type structure wherein the polyoxyethylene or polyoxyethylene-polyoxypropylene copolymeric units are grafted onto the siloxane backbone, or the SPE can have an ABA block copolymeric structure wherein A represents the polyether portion and B the siloxane portion of an ABA structure.
- Non-crosslinked silicone polyethers suitable for use herein have the formula MD 0-1,000 D′ 1-100 M, most preferably the formula MD 0-500 D′ 1-50 M, where M represents monofunctional unit R 3 SiO 1/2 , D represents difunctional unit R 2 SiO 2/2 , and D′ represents difunctional unit RR′SiO 2/2 .
- R is an alkyl group containing 1-6 carbon atoms or an aryl group, and R′ is an oxyalkylene containing moiety.
- the R′ groups may contain only oxyethylene (EO) units; a combination of oxyethylene (EO) and oxypropylene (PO) units; or a combination of oxyethylene (EO) units, oxypropylene (PO) units, and oxybutylene (BO) units.
- Preferred R′ groups include oxyalkylene units in the approximate ratio of EO 3-100 PO 0-100 , most preferably in the ratio EO 3-30 PO 1-30 .
- R′ moieties typically includes a divalent radical such as —C m H 2m — where m is 2-8 for connecting the oxyalkylene portion of R′ to the siloxane backbone.
- Such moieties also contain a terminating radical for the oxyalkylene portion of R′ such as hydrogen, hydroxyl, or an alkyl, aryl, alkoxy, or acetoxy group.
- Non-crosslinked silicone polyethers useful herein can also be of a type having the formula M′D 10-1,000 D′ 0-100 M′, most preferably the formula M′D 10-500 D′ 0-50 M′, wherein M′ represents monofunctional unit R 2 R′SiO 1/2 , D represents difunctional unit R 2 SiO 2/2 , and D′ represents difunctional unit RR′SiO 2/2 .
- R can be an alkyl group containing 1-6 carbon atoms or an aryl group, and again R′ represents an oxyalkylene containing moiety.
- R′ groups typically contain only oxyethylene (EO) units or combinations of oxyethylene (EO) and oxypropylene (PO) units. Such R′ groups include these oxyalkylene units in the ratio EO 3-100 PO 0-100 , most preferably EO 3-30 PO 1-30 .
- R′ moieties typically include a divalent radical —C m H 2m — where m is 2-8 for connecting the oxyalkylene portions of R′ to the siloxane backbone.
- R′ contains a terminating radical for oxyalkylene portions of R′ such as hydrogen, hydroxyl, an alkyl, aryl, alkoxy, or acetoxy group.
- non-crosslinked silicone polyethers useful herein can having the formula MD 0-1,000 D′ 0-100 D′′ 1-1,00 M wherein D′′ represents difunctional unit RR′′SiO 2/2 , and R′′ is an alkyl group containing 1-40 carbon atoms. M, D, D′, and R, are the same as defined above.
- Table I shows some representative non-crosslinked silicone polyethers conforming to these formulas which can be used in preparing emulsions according to the invention.
- TABLE I Non-Crosslinked Nominal Structure of Non-Crosslinked Silicone Polyether Silicone Polyethers A MD 8.6 D′ 3.6 M where R is —CH 3 and R′ is —(CH 2 ) 3 (EO) 12 OH B MD 108 D′ 10 M where R is —CH 3 and R′ is —(CH 2 ) 3 (EO) 10 (PO) 4 OH C M′D′ 75 M′ where R is —CH 3 and R′ is —(CH 2 ) 3 (EO) 18 (PO) 18 OAc D M′D′ 50 M′ where R is —CH 3 and R′is —(CH 2 ) 3 (EO) 18 (PO) 18 OH E M′D′ 13 M′ where R is —CH 3 and R′ is —(CH 2 ) 3 (EO) 12 OH F MD 22 D′ 2 M
- Emulsions prepared according to the invention may contain a cosurfactant.
- the cosurfactant can be a compound such as a monohydroxy alcohol, a diol, a triol, or it can be a glycol ether.
- Some representative cosurfactants which can be used include 1-butanol, 1-pentanol, 1-decanol, 1-hexadecanol, ethylene glycol, propylene glycol, trimethylene glycol, glycerol, and di(ethylene) glycol hexyl ether.
- Most preferred are glycol ethers, which are available commercially from The Dow Chemical Company, Midland, Mich., under their trademark DOWANOL®.
- the ⁇ Si—H polysiloxane is represented by compounds of the formula R 3 SiO(R′ 2 SiO) a (R′′HSiO) b SiR 3 , compounds of the formula HR 2 SiO(R′ 2 SiO) c SiR 2 H, or compounds of the formula HR 2 SiO(R′2SiO) a (R′′HSiO) b SiR 2 H, and mixtures thereof.
- R, R′, and R′′ are alkyl groups with 1-6 carbon atoms; a is 0-250; b is 1-250; and c is 0-250.
- the ⁇ Si—H containing polysiloxane can also comprise an alkylhydrogen cyclosiloxane or an alkylhydrogen-dialkyl cyclosiloxane copolymer, represented in general by the formula (R′ 2 SiO) a (R′′HSiO) b where R′, R′′, a, and b, are as defined above.
- R′, R′′, a, and b are as defined above.
- a is 0-7; and b is 3-10.
- Some representative compounds are (OSiMeH) 4 , (OSiMeH) 3 (OSiMeC 6 H 13 ), (OSiMeH) 2 (OSiMeC 6 H 13 ) 2 , and (OSiMeH)(OSiMeC 6 H 13 ) 3 , where Me is
- the mono-alkenyl polyether is a compound of the formula CH 2 ⁇ CH(CH 2 ) f O(CH 2 CH 2 O) g (CH 2 CH 3 CHO) h T, or a compound of the formula CH 2 ⁇ CH-Q-O(CH 2 CH 2 O) g (CH 2 CH 3 CHO) h T.
- T represents an end group, which can be hydrogen; a C1-C10 alkyl group such as methyl, ethyl, propyl, butyl, and decyl; an aryl group such as phenyl; or a C1-C20 acyl group such as acetyl, propionyl, butyryl, lauroyl, myristoyl, and stearoyl.
- Q is a divalent linking group containing unsaturation such as phenylene —C 6 H 4 —.
- the value of f is 1-6; g has a value of 4-30; and h can be zero or have a value of 1-100.
- Unsaturated hydrocarbons which can be used include ⁇ , ⁇ )-dienes of the formula CH 2 ⁇ CH(CH 2 ) d CH ⁇ CH 2 where d is 1-20. Some representative ⁇ , ⁇ )-dienes are 1,4-pentadiene;
- Other unsaturated hydrocarbons which can be used include ⁇ , ⁇ -diynes of the formula CH ⁇ C(CH 2 ) e C ⁇ CH; or ⁇ , ⁇ -ene-ynes of the formula CH 2 ⁇ CH(CH 2 ) e C ⁇ CH where e is 0-20.
- Some representative ⁇ , ⁇ -diynes are 1,3-butadiyne HC ⁇ C—C ⁇ CH and 1,5-hexadiyne (dipropargyl) HC ⁇ C—CH 2 CH 2 —C ⁇ CH.
- ⁇ , ⁇ -ene-yne is hexene-5-yne-1 CH 2 ⁇ CHCH 2 CH 2 C ⁇ CH.
- silicone oil as used herein is intended to include compounds containing a silicon atom such as (i) low molecular weight linear and cyclic volatile methyl siloxanes, and (ii) low molecular weight linear and cyclic volatile and non-volatile alkyl and aryl siloxanes. Most preferred, however, are low molecular weight linear and cyclic volatile methyl siloxanes (VMS).
- VMS low molecular weight linear and cyclic volatile methyl siloxanes
- VMS compounds correspond to the average unit formula (CH 3 ) j SiO (4-j)/2 in which j has an average value of two to three.
- the compounds contain siloxane units joined by ⁇ Si—O—Si ⁇ bonds.
- Representative units are monofunctional “M” units (CH 3 ) 3 SiO 1/2 and difunctional “D” units (CH 3 ) 2 SiO 2/2 .
- Linear VMS have the formula (CH 3 ) 3 SiO ⁇ (CH 3 ) 2 SiO ⁇ k Si(CH 3 ) 3 .
- the value of k is 0-5.
- Cyclic VMS have the formula ⁇ (CH 3 ) 2 SiO ⁇ m .
- the value of m is 3-9.
- these volatile methyl siloxane have a boiling point less than about 250° C. and viscosity of about 0.65 to about 5.0 mm 2 /s.
- Representative linear volatile methyl siloxanes are hexamethyldisiloxane (MM) with a boiling point of 100° C., viscosity of 0.65 mm 2 /s, and formula Me 3 SiOSiMe 3 ; octamethyltrisiloxane (MDM) with a boiling point of 152° C., viscosity of 1.04 mm 2 /s, and formula Me 3 SiOMe 2 SiOSiMe 3 ; decamethyltetrasiloxane (MD 2 M) with a boiling point of 194° C., viscosity of 1.53 mm 2 /s, and formula Me 3 SiO(Me 2 SiO) 2 SiMe 3 ; dodecamethylpentasiloxane (MD 3 M) with a boiling point of 229° C., viscosity of 2.06 mm 2 /s, and formula Me 3 SiO(Me 2 SiO) 3 SiMe 3 ; tetradecamethylhex
- Representative cyclic volatile methyl siloxanes are hexamethylcyclotrisiloxane (D 3 ) a solid with a boiling point of 134° C. and formula ⁇ (Me 2 )SiO ⁇ 3 ; octamethylcyclotetrasiloxane (D 4 ) with a boiling point of 176° C., viscosity of 2.3 mm 2 /s, and formula ⁇ (Me 2 )SiO ⁇ 4 ; decamethylcyclopentasiloxane (D 5 ) with a boiling point of 210° C., viscosity of 3.87 mm 2 /s, and formula ⁇ (Me 2 )SiO ⁇ 5 ; and dodecamethylcyclohexasiloxane (D 6 ) with a boiling point of 245° C., viscosity of 6.62 mm 2 /s, and formula ⁇ (Me 2 )SiO ⁇ 6 .
- Representative branched volatile methyl siloxanes are heptamethyl-3- ⁇ (trimethylsilyl)oxy ⁇ trisiloxane (M 3 T) with a boiling point of 192° C., viscosity of 1.57 mm 2 /s, and formula C 10 H 30 O 3 Si 4 ; hexamethyl-3,3,bis ⁇ (trimethylsilyl)oxy ⁇ trisiloxane (M 4 Q) with a boiling point of 222° C., viscosity of 2.86 mm 2 /s, and formula C 12 H 36 O 4 Si 5 ; and pentamethyl ⁇ (trimethylsilyl)oxy ⁇ cyclotrisiloxane (MD 3 ) with the formula C 8 H 24 O 4 Si 4 .
- the invention also includes using low molecular weight linear and cyclic volatile and non-volatile alkyl and aryl siloxanes represented respectively by formulas R 3 SiO(R 2 SiO) n SiR 3 and (R 2 SiO) p .
- R can be alkyl groups with 2-20 carbon atoms or aryl groups such as phenyl.
- n is 0-80, preferably 5-20.
- p is 3-9, preferably 4-6.
- These polysiloxanes have a viscosity generally in the range of about 1-100 mm 2 /s.
- Polysiloxanes can also be used where n has a value sufficient to provide siloxane polymers with a viscosity in the range of about 100-1,000 mm 2 /sec. Typically, n can be about 80-375. Illustrative of such polysiloxanes are polydimethylsiloxane, polydiethylsiloxane, polymethylethylsiloxane, polymethylphenylsiloxane, and polydiphenylsiloxane.
- the silicone oil component can be omitted.
- ⁇ , ⁇ -ene-yne requires a catalyst to effect the reaction between the ⁇ SiH containing polysiloxane, the mono-alkenyl polyether, and the ⁇ , ⁇ -unsaturated hydrocarbon.
- Suitable catalysts are Group VIII transition metals, i.e., the noble metals. Such noble metal catalysts are described in U.S. Pat. No. 3,923,705, incorporated herein by reference. A particularly preferred catalyst is described in Karstedt's U.S. Pat. Nos. 3,715,334 and 3,814,730, incorporated herein by reference.
- Karstedt's catalyst is a platinum divinyl tetramethyl disiloxane complex, typically containing about one weight percent of platinum, carried in a polydimethylsiloxane fluid or in a solvent such as toluene.
- the particular catalysts used in Examples 1 and 2 appearing below were 20 ⁇ l and 200 ⁇ l portions, respectively, of Karstedt's catalyst, used as one weight percent of platinum carried in a 2.0 mm 2 /s polydimethylsiloxane fluid.
- Another preferred platinum catalyst is a reaction product of chloroplatinic acid and an organosilicon compound containing terminal aliphatic unsaturation. It is described in U.S. Pat. No. 3,419,593, incorporated herein by reference.
- the noble metal catalysts are used in amounts from 0.00001-0.5 parts of noble metal per 100 weight parts of ⁇ SiH containing polysiloxane, preferably 0.00001-0.02 parts of noble metal, most preferably 0.00001-0.002 parts of noble metal.
- compositions according to the first embodiment of the invention the following amounts of each of the components in percent by weight of the composition, can be employed:
- compositions according to the second embodiment of the invention the following amounts of each of the components in percent by weight of the composition, can be employed:
- compositions made according to the invention may contain other components, as required, for preparing the compositions for particular applications.
- additives for stabilizing the composition or adjusting its viscosity such as ethanol, or water soluble polymers such as xanthan gum, guar gum, carboxymethyl cellulose, polyvinyl alcohol, polyvinylpyrrolidone, carboxyvinyl polymers, hydroxyethyl cellulose, and polyoxyethylene glycol distearate;
- film forming agents such as polymers of radically polymerizable (meth)acrylic monomers, copolymers of silicone polymers with radically polymerizable (meth)acrylic monomers, poly(N-acylalkylene imines), poly(N-methylpyrrolidones), and silicone resins which contain fluorinated organic groups, amino groups, or silanol groups;
- oxidation inhibitors such as butylated hydroxyanisole (BHA), but
- compositions of the invention While mechanical equipment such as mixers, mills, homogenizers, and extruders, can be used in preparing compositions of the invention, it is most preferred to form them without application of any shearing force, as by simply handshaking the ingredients.
- the crosslinked silicone elastomer was swollen with about 86.5 percent by weight of volatile silicone oil decamethylcyclopentasiloxane.
- the D 5 swollen elastomer was prepared by reacting (i) ⁇ Si—H containing polysiloxane MD 8.7 D′ 3.7 M where M is (CH 3 ) 3 SiO—, D is (CH 3 ) 2 SiO ⁇ , and D′ is (CH 3 )(H)SiO ⁇ , with (ii) ⁇ , ⁇ -diene 1,5-hexadiene.
- the reaction was carried out in the presence of D 5 according to the method in U.S. Pat. No. 5,654,362 (Aug. 5, 1997).
- the crosslinked silicone elastomer having no oxyalkylene units in its molecule, used in Example 2, is a material typically referred to in the art, as a non-emulsifying silicone elastomer, meaning that polyoxyalkylene units are absent.
- compositions prepared according to the invention can be used in various over-the-counter (OTC) personal care products.
- OTC over-the-counter
- they can be used in antiperspirants, deodorants, skin creams, skin care lotions, moisturizers, facial treatments such as acne or wrinkle removers, personal and facial cleansers, bath oils, perfumes, colognes, sachets, sunscreens, pre-shave and after-shave lotions, liquid soaps, shaving soaps, shaving lathers, hair shampoos, hair conditioners, hair sprays, mousses, permanents, depilatories, cuticle coats, make-ups, color cosmetics, foundations, blushes, lipsticks, lip balms, eyeliners, mascaras, oil removers, color cosmetic removers, and powders.
- the compositions are also useful as carriers for pharmaceuticals, biocides, herbicides, pesticides, and to incorporate water and water-soluble substances into hydrophobic systems.
Landscapes
- Chemical & Material Sciences (AREA)
- Dispersion Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Silicon Polymers (AREA)
- Cosmetics (AREA)
- Colloid Chemistry (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
Abstract
Emulsions are prepared by heating and polymerizing a mixture containing (i) a non-crosslinked silicone polyether; (ii) optionally, a cosurfactant which can be a monohydroxy alcohol, diol, triol, or glycol ether; (iii) an ≡Si—H containing polysiloxane; (iv) a mono-alkenyl polyether; (v) an α,ω-diene, α,ω-diyne, or α,ω-ene-yne; (vi) optionally, a silicone oil such as (a) a low molecular weight linear or cyclic volatile methyl siloxane, or (b) a low molecular weight linear or cyclic volatile or non-volatile alkyl or aryl siloxane; (vii) a platinum catalyst; and (viii) water.
Description
- This is a division of co-pending U.S. patent application Ser. No. 09/866,995, filed May 29, 2001.
- This invention is related to emulsions and preparing emulsions using non-crosslinked silicone polyethers and crosslinked silicone polyethers. In a first embodiment, emulsions containing non-crosslinked silicone polyethers and crosslinked silicone polyethers are prepared by emulsion polymerization. In a second embodiment, emulsions containing non-crosslinked silicone polyethers and crosslinked silicone elastomers containing no oxyalkylene units are prepared mechanically.
- While U.S. Pat. No. 5,387,417 (Feb. 7, 1995) suggests using certain non-crosslinked silicone polyethers in combination with certain crosslinked silicone polyethers for preparing emulsions, the '417 patent does not teach preparing emulsions using emulsion polymerization, a first embodiment of the present invention.
- In addition, where emulsions in the '417 patent are prepared mechanically, the '417 patent does not teach preparing mechanical emulsions with a non-crosslinked silicone polyether in combination with a crosslinked silicone elastomer containing no oxyalkylene units, a second embodiment of the invention. Further, and in this regard, the '417 patent does not teach preparing emulsions with a non-crosslinked silicone polyether in combination with a crosslinked silicone elastomer containing no oxyalkylene units, without application of any mechanical shearing force.
- In a first embodiment, the invention is directed to a method of preparing emulsions by heating and polymerizing a mixture containing (i) a non-crosslinked silicone polyether; (ii) optionally, a cosurfactant which can be a monohydroxy alcohol, diol, triol, or glycol ether; (iii) an ≡Si—H containing polysiloxane; (iv) a mono-alkenyl polyether; (v) an α,ω-diene, α,ω-diyne, or α,ω)-ene-yne; (vi) optionally, a silicone oil such as (a) a low molecular weight linear or cyclic volatile methyl siloxane, or (b) a low molecular weight linear or cyclic volatile or non-volatile alkyl or aryl siloxane; (vii) a platinum catalyst; and (viii) water.
- The crosslinked silicone polyether is obtained as a result of polymerization of components (iii), (iv), and (v).
- In a second embodiment, the invention is directed to a method of making oil-in-water emulsions by mixing (i) a non-crosslinked silicone polyether; (ii) a cosurfactant such as a monohydroxy alcohol, diol, triol, or glycol ether; and (iii) water; with (iv) a crosslinked silicone elastomer containing no oxyalkylene units prepared by reacting (a) an ≡Si—H containing polysiloxane; (b) an α,ω-diene, α,ω-diyne, or α,ω-ene-yne; (c) a silicone oil such as (I) a low molecular weight linear or cyclic volatile methyl siloxanes, or (II) a low molecular weight linear or cyclic volatile or non-volatile alkyl or aryl siloxane; and (d) a platinum catalyst.
- The invention is also directed to emulsions prepared according to the methods of each of these embodiments.
- These and other features of the invention will become apparent from a consideration of the detailed description.
- Non-Crosslinked Silicone Polyether (SPE) Surfactant
- The non-crosslinked silicone polyether is generally water soluble or water dispersible. It can have a rake type structure wherein the polyoxyethylene or polyoxyethylene-polyoxypropylene copolymeric units are grafted onto the siloxane backbone, or the SPE can have an ABA block copolymeric structure wherein A represents the polyether portion and B the siloxane portion of an ABA structure.
- Non-crosslinked silicone polyethers suitable for use herein have the formula MD 0-1,000D′1-100M, most preferably the formula MD0-500D′1-50M, where M represents monofunctional unit R3SiO1/2, D represents difunctional unit R2SiO2/2, and D′ represents difunctional unit RR′SiO2/2. In these formulas, R is an alkyl group containing 1-6 carbon atoms or an aryl group, and R′ is an oxyalkylene containing moiety. The R′ groups may contain only oxyethylene (EO) units; a combination of oxyethylene (EO) and oxypropylene (PO) units; or a combination of oxyethylene (EO) units, oxypropylene (PO) units, and oxybutylene (BO) units. Preferred R′ groups include oxyalkylene units in the approximate ratio of EO3-100PO0-100, most preferably in the ratio EO3-30PO1-30.
- R′ moieties typically includes a divalent radical such as —C mH2m— where m is 2-8 for connecting the oxyalkylene portion of R′ to the siloxane backbone. Such moieties also contain a terminating radical for the oxyalkylene portion of R′ such as hydrogen, hydroxyl, or an alkyl, aryl, alkoxy, or acetoxy group.
- Non-crosslinked silicone polyethers useful herein can also be of a type having the formula M′D 10-1,000D′0-100M′, most preferably the formula M′D10-500D′0-50M′, wherein M′ represents monofunctional unit R2R′SiO1/2, D represents difunctional unit R2SiO2/2, and D′ represents difunctional unit RR′SiO2/2. In these formulas, R can be an alkyl group containing 1-6 carbon atoms or an aryl group, and again R′ represents an oxyalkylene containing moiety. As noted previously, R′ groups typically contain only oxyethylene (EO) units or combinations of oxyethylene (EO) and oxypropylene (PO) units. Such R′ groups include these oxyalkylene units in the ratio EO3-100PO0-100, most preferably EO3-30PO1-30.
- As also noted previously, R′ moieties typically include a divalent radical —C mH2m— where m is 2-8 for connecting the oxyalkylene portions of R′ to the siloxane backbone. In addition, the moiety R′ contains a terminating radical for oxyalkylene portions of R′ such as hydrogen, hydroxyl, an alkyl, aryl, alkoxy, or acetoxy group.
- In addition, non-crosslinked silicone polyethers useful herein can having the formula MD 0-1,000D′0-100D″1-1,00M wherein D″ represents difunctional unit RR″SiO2/2, and R″ is an alkyl group containing 1-40 carbon atoms. M, D, D′, and R, are the same as defined above.
- Table I shows some representative non-crosslinked silicone polyethers conforming to these formulas which can be used in preparing emulsions according to the invention.
TABLE I Non-Crosslinked Nominal Structure of Non-Crosslinked Silicone Polyether Silicone Polyethers A MD8.6D′3.6M where R is —CH3 and R′ is —(CH2)3(EO)12OH B MD108D′10M where R is —CH3 and R′ is —(CH2)3(EO)10(PO)4OH C M′D′75M′ where R is —CH3 and R′ is —(CH2)3(EO)18(PO)18OAc D M′D′50M′ where R is —CH3 and R′is —(CH2)3(EO)18(PO)18OH E M′D′13M′ where R is —CH3 and R′ is —(CH2)3(EO)12OH F MD22D′2M where R is —CH3 and R′ is —(CH2)3(EO)12(PO)12OH - Cosurfactant
- Emulsions prepared according to the invention may contain a cosurfactant. The cosurfactant can be a compound such as a monohydroxy alcohol, a diol, a triol, or it can be a glycol ether. Some representative cosurfactants which can be used include 1-butanol, 1-pentanol, 1-decanol, 1-hexadecanol, ethylene glycol, propylene glycol, trimethylene glycol, glycerol, and di(ethylene) glycol hexyl ether. Most preferred are glycol ethers, which are available commercially from The Dow Chemical Company, Midland, Mich., under their trademark DOWANOL®.
- ≡Si—H Containing Polysiloxane
- The ≡Si—H polysiloxane is represented by compounds of the formula R 3SiO(R′2SiO)a(R″HSiO)bSiR3, compounds of the formula HR2SiO(R′2SiO)cSiR2H, or compounds of the formula HR2SiO(R′2SiO)a(R″HSiO)bSiR2H, and mixtures thereof. In the three formulas, R, R′, and R″, are alkyl groups with 1-6 carbon atoms; a is 0-250; b is 1-250; and c is 0-250.
- The ≡Si—H containing polysiloxane can also comprise an alkylhydrogen cyclosiloxane or an alkylhydrogen-dialkyl cyclosiloxane copolymer, represented in general by the formula (R′ 2SiO)a(R″HSiO)b where R′, R″, a, and b, are as defined above. Preferably, a is 0-7; and b is 3-10. Some representative compounds are (OSiMeH)4, (OSiMeH)3(OSiMeC6H13), (OSiMeH)2(OSiMeC6H13)2, and (OSiMeH)(OSiMeC6H13)3, where Me is
- —CH 3.
- Mono-Alkenyl Polyether
- The mono-alkenyl polyether is a compound of the formula CH 2═CH(CH2)fO(CH2CH2O)g(CH2CH3CHO)hT, or a compound of the formula CH2═CH-Q-O(CH2CH2O)g(CH2CH3CHO)hT. In the formulas, T represents an end group, which can be hydrogen; a C1-C10 alkyl group such as methyl, ethyl, propyl, butyl, and decyl; an aryl group such as phenyl; or a C1-C20 acyl group such as acetyl, propionyl, butyryl, lauroyl, myristoyl, and stearoyl. Q is a divalent linking group containing unsaturation such as phenylene —C6H4—. The value of f is 1-6; g has a value of 4-30; and h can be zero or have a value of 1-100.
- α,ω-Diene, α,ω-Diyne, or α,ω-Ene-Yne
- Unsaturated hydrocarbons which can be used include α,ω)-dienes of the formula CH 2═CH(CH2)dCH═CH2 where d is 1-20. Some representative α,ω)-dienes are 1,4-pentadiene;
- 1,5-hexadiene; 1,6-heptadiene; 1,7-octadiene; 1,8-nonadiene; 1,9-decadiene; 1,11-dodecadiene; 1,13-tetradecadiene; and
- 1,19-eicosadiene.
- Other unsaturated hydrocarbons which can be used include α,ω-diynes of the formula CH≡C(CH 2)eC≡CH; or α,ω-ene-ynes of the formula CH2═CH(CH2)eC≡CH where e is 0-20. Some representative ═,ω-diynes are 1,3-butadiyne HC≡C—C≡CH and 1,5-hexadiyne (dipropargyl) HC≡C—CH2CH2—C≡CH. An example of a suitable
- α,ω-ene-yne is hexene-5-yne-1 CH 2═CHCH2CH2C≡CH.
- Silicone Oil
- The term silicone oil as used herein is intended to include compounds containing a silicon atom such as (i) low molecular weight linear and cyclic volatile methyl siloxanes, and (ii) low molecular weight linear and cyclic volatile and non-volatile alkyl and aryl siloxanes. Most preferred, however, are low molecular weight linear and cyclic volatile methyl siloxanes (VMS).
- VMS compounds correspond to the average unit formula (CH 3)jSiO(4-j)/2 in which j has an average value of two to three. The compounds contain siloxane units joined by ≡Si—O—Si≡ bonds. Representative units are monofunctional “M” units (CH3)3SiO1/2 and difunctional “D” units (CH3)2SiO2/2.
- The presence of trifunctional “T” units CH 3SiO3/2 results in the formation of branched linear or cyclic volatile methyl siloxanes. The presence of tetrafunctional “Q” units SiO4/2 results in the formation of branched linear or cyclic volatile methyl siloxanes.
- Linear VMS have the formula (CH 3)3SiO{(CH3)2SiO}kSi(CH3)3. The value of k is 0-5. Cyclic VMS have the formula {(CH3)2SiO}m. The value of m is 3-9. Preferably, these volatile methyl siloxane have a boiling point less than about 250° C. and viscosity of about 0.65 to about 5.0 mm2/s.
- Representative linear volatile methyl siloxanes are hexamethyldisiloxane (MM) with a boiling point of 100° C., viscosity of 0.65 mm 2/s, and formula Me3SiOSiMe3; octamethyltrisiloxane (MDM) with a boiling point of 152° C., viscosity of 1.04 mm2/s, and formula Me3SiOMe2SiOSiMe3; decamethyltetrasiloxane (MD2M) with a boiling point of 194° C., viscosity of 1.53 mm2/s, and formula Me3SiO(Me2SiO)2SiMe3; dodecamethylpentasiloxane (MD3M) with a boiling point of 229° C., viscosity of 2.06 mm2/s, and formula Me3SiO(Me2SiO)3SiMe3; tetradecamethylhexasiloxane (MD4M) with a boiling point of 245° C., viscosity of 2.63 mm2/s, and formula Me3SiO(Me2SiO)4SiMe3; and hexadecamethylheptasiloxane (MD5M) with a boiling point of 270° C., viscosity of 3.24 mm2/s, and formula Me3SiO(Me2SiO)5SiMe3.
- Representative cyclic volatile methyl siloxanes are hexamethylcyclotrisiloxane (D 3) a solid with a boiling point of 134° C. and formula {(Me2)SiO}3; octamethylcyclotetrasiloxane (D4) with a boiling point of 176° C., viscosity of 2.3 mm2/s, and formula {(Me2)SiO}4; decamethylcyclopentasiloxane (D5) with a boiling point of 210° C., viscosity of 3.87 mm2/s, and formula {(Me2)SiO}5; and dodecamethylcyclohexasiloxane (D6) with a boiling point of 245° C., viscosity of 6.62 mm2/s, and formula {(Me2)SiO}6.
- Representative branched volatile methyl siloxanes are heptamethyl-3-{(trimethylsilyl)oxy}trisiloxane (M 3T) with a boiling point of 192° C., viscosity of 1.57 mm2/s, and formula C10H30O3Si4; hexamethyl-3,3,bis {(trimethylsilyl)oxy} trisiloxane (M4Q) with a boiling point of 222° C., viscosity of 2.86 mm2/s, and formula C12H36O4Si5; and pentamethyl {(trimethylsilyl)oxy} cyclotrisiloxane (MD3) with the formula C8H24O4Si4.
- The invention also includes using low molecular weight linear and cyclic volatile and non-volatile alkyl and aryl siloxanes represented respectively by formulas R 3SiO(R2SiO)nSiR3 and (R2SiO)p. R can be alkyl groups with 2-20 carbon atoms or aryl groups such as phenyl. The value of n is 0-80, preferably 5-20. The value of p is 3-9, preferably 4-6. These polysiloxanes have a viscosity generally in the range of about 1-100 mm2/s.
- Polysiloxanes can also be used where n has a value sufficient to provide siloxane polymers with a viscosity in the range of about 100-1,000 mm 2/sec. Typically, n can be about 80-375. Illustrative of such polysiloxanes are polydimethylsiloxane, polydiethylsiloxane, polymethylethylsiloxane, polymethylphenylsiloxane, and polydiphenylsiloxane.
- If desired, the silicone oil component can be omitted.
- CATALYST
- Polymerization of the ≡Si—H containing polysiloxane, the mono-alkenyl polyether, and the α,ω-diene, α,ω-diyne, or
- α,ω-ene-yne, requires a catalyst to effect the reaction between the ≡SiH containing polysiloxane, the mono-alkenyl polyether, and the α,ω-unsaturated hydrocarbon. Suitable catalysts are Group VIII transition metals, i.e., the noble metals. Such noble metal catalysts are described in U.S. Pat. No. 3,923,705, incorporated herein by reference. A particularly preferred catalyst is described in Karstedt's U.S. Pat. Nos. 3,715,334 and 3,814,730, incorporated herein by reference. Karstedt's catalyst is a platinum divinyl tetramethyl disiloxane complex, typically containing about one weight percent of platinum, carried in a polydimethylsiloxane fluid or in a solvent such as toluene.
- The particular catalysts used in Examples 1 and 2 appearing below were 20 μl and 200 μl portions, respectively, of Karstedt's catalyst, used as one weight percent of platinum carried in a 2.0 mm 2/s polydimethylsiloxane fluid. Another preferred platinum catalyst is a reaction product of chloroplatinic acid and an organosilicon compound containing terminal aliphatic unsaturation. It is described in U.S. Pat. No. 3,419,593, incorporated herein by reference. The noble metal catalysts are used in amounts from 0.00001-0.5 parts of noble metal per 100 weight parts of ≡SiH containing polysiloxane, preferably 0.00001-0.02 parts of noble metal, most preferably 0.00001-0.002 parts of noble metal.
- In preparing compositions according to the first embodiment of the invention, the following amounts of each of the components in percent by weight of the composition, can be employed:
- (i) 5-60 percent by weight of the non-crosslinked silicone polyether;
- (ii) optionally, 5-60 percent by weight of the cosurfactant;
- (iii) 5-50 percent by weight of the ≡Si—H containing polysiloxane;
- (iv) 5-50 percent by weight of the mono-alkenyl polyether;
- (v) 1-10 percent by weight of the α,ω-diene, α,ω-diyne, or α,ω)-ene-yne;
- (vi) optionally, 5-60 percent by weight of the silicone oil;
- (vii) 1-100 parts per million of platinum catalyst; and
- (viii) 10-60 percent by weight of water.
- In preparing compositions according to the second embodiment of the invention, the following amounts of each of the components in percent by weight of the composition, can be employed:
- (i) 1-50 percent by weight of the non-crosslinked silicone polyether;
- (ii) 1-50 percent by weight of the cosurfactant;
- (iii) 0.1-73.0 percent by weight of the crosslinked silicone elastomer containing no oxyalkylene units; and
- (iv) 25-97.9 percent by weight of water.
- Compositions made according to the invention may contain other components, as required, for preparing the compositions for particular applications. Representative of such components are, for example, (i) additives for stabilizing the composition or adjusting its viscosity such as ethanol, or water soluble polymers such as xanthan gum, guar gum, carboxymethyl cellulose, polyvinyl alcohol, polyvinylpyrrolidone, carboxyvinyl polymers, hydroxyethyl cellulose, and polyoxyethylene glycol distearate; (ii) film forming agents such as polymers of radically polymerizable (meth)acrylic monomers, copolymers of silicone polymers with radically polymerizable (meth)acrylic monomers, poly(N-acylalkylene imines), poly(N-methylpyrrolidones), and silicone resins which contain fluorinated organic groups, amino groups, or silanol groups; (iii) oxidation inhibitors such as butylated hydroxyanisole (BHA), butylated hydroxy toluene (BHT), and orizanol; (iv) antifreezes such as ethanol, isopropyl alcohol, 1,3-butylene glycol, ethylene glycol, propylene glycol, and glycerol; (v) antimicrobials and preservatives such as TRICLOSAN and TRICLOCARBAN; (vi) pearlescent agents; (vii) chelating agents such as ethylene diamine tetraacetic acid, citric acid, and ethane-1-hydroxy-1,1-diphosphonic acid; (viii) UV absorbers including benzophenone derivatives such as 2-hydroxy-4-methoxy benzophenone, benzotriazole derivatives such as 2-(2′-hydroxy-5′-methylphenyl) benzotriazole, and cinnamic acid esters; (ix) colorants such as chromatogens, dyes, and pigments; (x) aerosol spray enabling agents; (xi) vitamins; (xii) hair tonics; (xiii) growth promoters; (xiv) hormones; (xv) fragrances; and (xvi) perfumes.
- While mechanical equipment such as mixers, mills, homogenizers, and extruders, can be used in preparing compositions of the invention, it is most preferred to form them without application of any shearing force, as by simply handshaking the ingredients.
- The following examples are set forth in order to illustrate the invention in more detail.
- An oil-in-water microemulsion containing an in situ prepared crosslinked silicone polyether was formed by combing and handshaking the following ingredients in a sealed vial:
- a. 2.4983 gram of a non-crosslinked silicone polyether having the formula MD 22D′2M where M is (CH3)3SiO—, D is (CH3)2SiO═, and D′ is (CH3)(EO12PO12)SiO═;
- b. 2.5224 gram of the cosurfactant di(ethylene)glycol hexyl ether of the formula CH 3(CH2)5OCH2CH2OCH2CH2OH;
- c. 2.5633 gram of deionized water;
- d. 0.2767 of the ≡Si—H containing polysiloxane of the formula MD 8.7D′3.7M where M is (CH3)3SiO—, D is (CH3)2SiO═, and D′ is (CH3)(H)SiO≡;
- e. 2.0010 gram of the volatile silicone oil D 5, i.e., decamethylcyclopentasiloxane;
- f. 0.1967 gram of the mono-alkenyl polyether of the formula CH 2═CHCH2O(CH2CH2O)12H;
- g. 0.0270 gram of platinum catalyst;
- h. 0.065 gram of the α,ω-diene compound 1,5-hexadiene, i.e., CH 2═CH(CH2)2CH═CH2.
- The sealed vial and its contents were placed in an oven for one hour at 90° C. to initiate the polymerization reaction, forming a suspension of cured particles of a crosslinked silicone polyether in water.
- An oil-in-water microemulsion containing cured particles of a crosslinked silicone elastomer having no oxyalkylene units in its molecule, was formed by adding the following ingredients to a vial:
- a. 4.9891 gram of a crosslinked silicone elastomer having no oxyalkylene units in its molecule. The crosslinked silicone elastomer was swollen with about 86.5 percent by weight of volatile silicone oil decamethylcyclopentasiloxane. The D 5 swollen elastomer was prepared by reacting (i) ≡Si—H containing polysiloxane MD8.7D′3.7M where M is (CH3)3SiO—, D is (CH3)2SiO═, and D′ is (CH3)(H)SiO═, with (ii) α,ω-diene 1,5-hexadiene. The reaction was carried out in the presence of D5 according to the method in U.S. Pat. No. 5,654,362 (Aug. 5, 1997).
- b. 5.0145 gram of non-crosslinked silicone polyether MD 22D′2M where M is (CH3)3SiO—, D is (CH3)2SiO═, and D′ is (CH3)(EO12PO12)SiO═;
- c. 2.5532 gram of cosurfactant di(ethylene)glycol hexyl ether; and
- d. 5.0613 gram of deionized water.
- The vial and its contents were handshaken for one minute, in order to disperse the cured particles of crosslinked silicone elastomer, in water.
- The crosslinked silicone elastomer having no oxyalkylene units in its molecule, used in Example 2, is a material typically referred to in the art, as a non-emulsifying silicone elastomer, meaning that polyoxyalkylene units are absent.
- Compositions prepared according to the invention can be used in various over-the-counter (OTC) personal care products. Thus, they can be used in antiperspirants, deodorants, skin creams, skin care lotions, moisturizers, facial treatments such as acne or wrinkle removers, personal and facial cleansers, bath oils, perfumes, colognes, sachets, sunscreens, pre-shave and after-shave lotions, liquid soaps, shaving soaps, shaving lathers, hair shampoos, hair conditioners, hair sprays, mousses, permanents, depilatories, cuticle coats, make-ups, color cosmetics, foundations, blushes, lipsticks, lip balms, eyeliners, mascaras, oil removers, color cosmetic removers, and powders. The compositions are also useful as carriers for pharmaceuticals, biocides, herbicides, pesticides, and to incorporate water and water-soluble substances into hydrophobic systems.
- Other variations may be made in compounds, compositions, and methods described herein without departing from the essential features of the invention. The embodiments of the invention specifically illustrated herein are exemplary only and not intended as limitations on their scope except as defined in the appended claims.
Claims (4)
1. A method of making oil-in-water emulsions comprising mixing (i) 1-50 percent by weight of a non-crosslinked silicone polyether; (ii) 1-50 percent by weight of a cosurfactant selected from the group consisting of monohydroxy alcohols, diols, triols, and glycol ethers; and (iii) 25-97.9 percent by weight of water; with (iv) 0.1-73.0 percent by weight of a crosslinked silicone elastomer containing no oxyalkylene units prepared by reacting (a) an ≡Si—H containing polysiloxane; (b) an α,ω-diene, α,ω-diyne, or α,ω-ene-yne; (c) a silicone oil selected from the group consisting of (I) low molecular weight linear and cyclic volatile methyl siloxanes, and (II) low molecular weight linear and cyclic volatile and non-volatile alkyl and aryl siloxanes; and (d) a platinum catalyst.
2. A method according to claim 1 in which the cosurfactant is selected from the group consisting of 1-butanol, 1-pentanol, 1-decanol, 1-hexadecanol, ethylene glycol, propylene glycol, trimethylene glycol, glycerol, and di(ethylene) glycol hexyl ether.
3. A method according to claim 1 in which the emulsion is prepared without application of any mechanical shearing force.
4. An emulsion prepared according to the method defined in claim 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/408,480 US20030207948A1 (en) | 2001-05-29 | 2003-04-07 | Emulsions containing crosslinked and non-crosslinked silicone polyethers |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/866,995 US6593422B2 (en) | 2001-05-29 | 2001-05-29 | Emulsions containing crosslinked and non-crosslinked silicone polyethers |
| US10/408,480 US20030207948A1 (en) | 2001-05-29 | 2003-04-07 | Emulsions containing crosslinked and non-crosslinked silicone polyethers |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US09/866,995 Division US6593422B2 (en) | 2001-05-29 | 2001-05-29 | Emulsions containing crosslinked and non-crosslinked silicone polyethers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US20030207948A1 true US20030207948A1 (en) | 2003-11-06 |
Family
ID=25348871
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US09/866,995 Expired - Fee Related US6593422B2 (en) | 2001-05-29 | 2001-05-29 | Emulsions containing crosslinked and non-crosslinked silicone polyethers |
| US10/408,480 Abandoned US20030207948A1 (en) | 2001-05-29 | 2003-04-07 | Emulsions containing crosslinked and non-crosslinked silicone polyethers |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US09/866,995 Expired - Fee Related US6593422B2 (en) | 2001-05-29 | 2001-05-29 | Emulsions containing crosslinked and non-crosslinked silicone polyethers |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US6593422B2 (en) |
| EP (1) | EP1390426A1 (en) |
| JP (1) | JP2004530753A (en) |
| KR (1) | KR100845417B1 (en) |
| CN (1) | CN1513017A (en) |
| BR (1) | BR0209771A (en) |
| WO (1) | WO2002096980A1 (en) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6593422B2 (en) * | 2001-05-29 | 2003-07-15 | Dow Corning Corporation | Emulsions containing crosslinked and non-crosslinked silicone polyethers |
| US6887934B2 (en) * | 2002-08-26 | 2005-05-03 | Dow Corning Corporation | Resin modified elastomers |
| US6770708B2 (en) * | 2002-08-27 | 2004-08-03 | Dow Corning Corporation | Silicone elastomers compositions |
| US20040235683A1 (en) * | 2003-05-23 | 2004-11-25 | Moffett Robert Harvey | Mold release composition and process therewith |
| ATE420149T1 (en) * | 2005-08-17 | 2009-01-15 | Dow Corning | LYOTROPIC LIQUID CRYSTALS AND VESICLES |
| DE102005039398A1 (en) * | 2005-08-20 | 2007-02-22 | Goldschmidt Gmbh | Process for the preparation of addition products of compounds containing SiH groups to olefin-containing reactants in aqueous media |
| US8067350B2 (en) * | 2005-12-15 | 2011-11-29 | Kimberly-Clark Worldwide, Inc. | Color changing cleansing composition |
| ES2543209T3 (en) * | 2009-09-24 | 2015-08-17 | Evonik Degussa Gmbh | Cross-linked polysiloxanes, process for preparing and using cross-linked polysiloxanes in emulsifying systems for water-in-oil emulsions |
| CN103113824A (en) * | 2013-01-18 | 2013-05-22 | 中科院广州化学有限公司 | Film-forming polysiloxane emulsion and preparation method thereof |
| US20150274970A1 (en) * | 2014-03-26 | 2015-10-01 | Wacker Chemical Corporation | Control of internal viscosity in in situ polymerized organopolysiloxane emulsions |
| CN112979436B (en) * | 2019-12-12 | 2022-05-17 | 中国科学院大连化学物理研究所 | A kind of method for preparing 2,5-hexanedione |
Citations (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4290897A (en) * | 1980-05-27 | 1981-09-22 | Dow Corning Corporation | Dewatering fine coal slurries using two types of organopolysiloxanes |
| US4526680A (en) * | 1984-05-30 | 1985-07-02 | Dow Corning Corporation | Silicone glycol collectors in the beneficiation of fine coal by froth flotation |
| US5300667A (en) * | 1992-08-10 | 1994-04-05 | Dow Corning Corporation | Water dispersible silicone composition |
| US5387417A (en) * | 1991-08-22 | 1995-02-07 | Dow Corning Corporation | Non-greasy petrolatum emulsion |
| US5389365A (en) * | 1994-02-07 | 1995-02-14 | Dow Corning Corporation | Silicone terpolymer containing water-in-oil emulsion derived from unsaturated ethylene oxides |
| US5654362A (en) * | 1996-03-20 | 1997-08-05 | Dow Corning Corporation | Silicone oils and solvents thickened by silicone elastomers |
| US5708057A (en) * | 1991-06-28 | 1998-01-13 | Dow Corning Toray Silicone Co., Ltd. | Silicone-modified water-based coating composition |
| US5811487A (en) * | 1996-12-16 | 1998-09-22 | Dow Corning Corporation | Thickening silicones with elastomeric silicone polyethers |
| US5871761A (en) * | 1996-09-13 | 1999-02-16 | Shin-Etsu Chemical Co., Ltd. | Method for the preparation of improved water-base toiletry composition |
| US5889108A (en) * | 1997-06-02 | 1999-03-30 | Dow Corning Corporation | Thickening solvents with elastomeric silicone polyethers |
| US5948855A (en) * | 1999-01-12 | 1999-09-07 | Dow Corning Corporation | Water-in-oil-in water emulsion |
| US6039935A (en) * | 1998-12-30 | 2000-03-21 | Elizabeth Arden Company, Division Of Conopco, Inc. | Sunscreen compositions |
| US6071975A (en) * | 1999-01-11 | 2000-06-06 | Dow Corning Corporation | Method of preparing silicone oil-in-water microemulsions |
| US6221979B1 (en) * | 1999-11-08 | 2001-04-24 | Dow Corning Corporation | Mixtures of silicone elastomers |
| US6476123B1 (en) * | 1999-08-03 | 2002-11-05 | Dow Corning Toray Silicone Co., Ltd. | Crosslinked organic particles, suspensions, and methods for preparing crosslinked organic particles and suspensions |
| US6531542B1 (en) * | 1999-08-03 | 2003-03-11 | Dow Corning Toray Silicone Company, Ltd. | Spherical crosslinked organic particles suspensions and methods of preparing spherical crosslinked organic particles and suspensions |
| US6593422B2 (en) * | 2001-05-29 | 2003-07-15 | Dow Corning Corporation | Emulsions containing crosslinked and non-crosslinked silicone polyethers |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6200581B1 (en) * | 1999-04-28 | 2001-03-13 | Dow Corning Corporation | Elastomeric silicone terpolymer |
| US6238657B1 (en) * | 1999-07-12 | 2001-05-29 | Dow Corning Corporation | Oil-in-oil and three-phase emulsions |
-
2001
- 2001-05-29 US US09/866,995 patent/US6593422B2/en not_active Expired - Fee Related
-
2002
- 2002-04-08 WO PCT/US2002/010975 patent/WO2002096980A1/en not_active Ceased
- 2002-04-08 KR KR1020037015534A patent/KR100845417B1/en not_active Expired - Fee Related
- 2002-04-08 CN CNA028108701A patent/CN1513017A/en active Pending
- 2002-04-08 JP JP2003500157A patent/JP2004530753A/en active Pending
- 2002-04-08 BR BR0209771-0A patent/BR0209771A/en not_active Application Discontinuation
- 2002-04-08 EP EP02774094A patent/EP1390426A1/en not_active Withdrawn
-
2003
- 2003-04-07 US US10/408,480 patent/US20030207948A1/en not_active Abandoned
Patent Citations (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4290897A (en) * | 1980-05-27 | 1981-09-22 | Dow Corning Corporation | Dewatering fine coal slurries using two types of organopolysiloxanes |
| US4526680A (en) * | 1984-05-30 | 1985-07-02 | Dow Corning Corporation | Silicone glycol collectors in the beneficiation of fine coal by froth flotation |
| US5708057A (en) * | 1991-06-28 | 1998-01-13 | Dow Corning Toray Silicone Co., Ltd. | Silicone-modified water-based coating composition |
| US5387417A (en) * | 1991-08-22 | 1995-02-07 | Dow Corning Corporation | Non-greasy petrolatum emulsion |
| US5300667A (en) * | 1992-08-10 | 1994-04-05 | Dow Corning Corporation | Water dispersible silicone composition |
| US5389365A (en) * | 1994-02-07 | 1995-02-14 | Dow Corning Corporation | Silicone terpolymer containing water-in-oil emulsion derived from unsaturated ethylene oxides |
| US5654362A (en) * | 1996-03-20 | 1997-08-05 | Dow Corning Corporation | Silicone oils and solvents thickened by silicone elastomers |
| US5871761A (en) * | 1996-09-13 | 1999-02-16 | Shin-Etsu Chemical Co., Ltd. | Method for the preparation of improved water-base toiletry composition |
| US5811487A (en) * | 1996-12-16 | 1998-09-22 | Dow Corning Corporation | Thickening silicones with elastomeric silicone polyethers |
| US5889108A (en) * | 1997-06-02 | 1999-03-30 | Dow Corning Corporation | Thickening solvents with elastomeric silicone polyethers |
| US6039935A (en) * | 1998-12-30 | 2000-03-21 | Elizabeth Arden Company, Division Of Conopco, Inc. | Sunscreen compositions |
| US6071975A (en) * | 1999-01-11 | 2000-06-06 | Dow Corning Corporation | Method of preparing silicone oil-in-water microemulsions |
| US5948855A (en) * | 1999-01-12 | 1999-09-07 | Dow Corning Corporation | Water-in-oil-in water emulsion |
| US6476123B1 (en) * | 1999-08-03 | 2002-11-05 | Dow Corning Toray Silicone Co., Ltd. | Crosslinked organic particles, suspensions, and methods for preparing crosslinked organic particles and suspensions |
| US6531542B1 (en) * | 1999-08-03 | 2003-03-11 | Dow Corning Toray Silicone Company, Ltd. | Spherical crosslinked organic particles suspensions and methods of preparing spherical crosslinked organic particles and suspensions |
| US6221979B1 (en) * | 1999-11-08 | 2001-04-24 | Dow Corning Corporation | Mixtures of silicone elastomers |
| US6593422B2 (en) * | 2001-05-29 | 2003-07-15 | Dow Corning Corporation | Emulsions containing crosslinked and non-crosslinked silicone polyethers |
Also Published As
| Publication number | Publication date |
|---|---|
| BR0209771A (en) | 2004-12-21 |
| US6593422B2 (en) | 2003-07-15 |
| CN1513017A (en) | 2004-07-14 |
| KR20040004665A (en) | 2004-01-13 |
| WO2002096980A1 (en) | 2002-12-05 |
| KR100845417B1 (en) | 2008-07-10 |
| EP1390426A1 (en) | 2004-02-25 |
| JP2004530753A (en) | 2004-10-07 |
| US20020193511A1 (en) | 2002-12-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0848029B1 (en) | Thickening silicones with elastomeric silicone polyethers | |
| US5889108A (en) | Thickening solvents with elastomeric silicone polyethers | |
| US5948855A (en) | Water-in-oil-in water emulsion | |
| EP0934959B1 (en) | Method of making (meth)acrylate polyether grafted and crosslinked silicone elastomers | |
| US6207717B1 (en) | Entrapment of vitamins with an elastomeric silicone polyether | |
| US5939478A (en) | Silicone polyether stabilized silicone latex solvent thickening | |
| US6168782B1 (en) | Elastomeric silicone containing an active ingredient | |
| US6200581B1 (en) | Elastomeric silicone terpolymer | |
| EP1390431B1 (en) | Polysiloxanes and gels and pastes containing them | |
| US5929164A (en) | Quenching post cure | |
| US6238657B1 (en) | Oil-in-oil and three-phase emulsions | |
| EP1551923B1 (en) | Silicone elastomers compositions | |
| US6593422B2 (en) | Emulsions containing crosslinked and non-crosslinked silicone polyethers | |
| EP1035154B1 (en) | Use of silicone polyethers with arylalkyl groups in personal care products |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| STCB | Information on status: application discontinuation |
Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION |