WO2016133946A1 - Micro-capsules à catalyseurs encapsulés - Google Patents
Micro-capsules à catalyseurs encapsulés Download PDFInfo
- Publication number
- WO2016133946A1 WO2016133946A1 PCT/US2016/018147 US2016018147W WO2016133946A1 WO 2016133946 A1 WO2016133946 A1 WO 2016133946A1 US 2016018147 W US2016018147 W US 2016018147W WO 2016133946 A1 WO2016133946 A1 WO 2016133946A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- microcapsules
- catalyst
- platinum
- process according
- water
- Prior art date
Links
- 239000003094 microcapsule Substances 0.000 title claims abstract description 165
- 239000003054 catalyst Substances 0.000 title claims abstract description 139
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 84
- 238000000034 method Methods 0.000 claims abstract description 72
- 239000000839 emulsion Substances 0.000 claims abstract description 65
- 239000000203 mixture Substances 0.000 claims abstract description 60
- 230000008569 process Effects 0.000 claims abstract description 57
- 150000003377 silicon compounds Chemical class 0.000 claims abstract description 51
- 239000002245 particle Substances 0.000 claims abstract description 44
- 229920001187 thermosetting polymer Polymers 0.000 claims abstract description 32
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims abstract description 31
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 31
- 239000010703 silicon Substances 0.000 claims abstract description 31
- 238000006459 hydrosilylation reaction Methods 0.000 claims abstract description 24
- 239000012736 aqueous medium Substances 0.000 claims abstract description 16
- 239000003112 inhibitor Substances 0.000 claims abstract description 9
- 230000000379 polymerizing effect Effects 0.000 claims abstract description 7
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 76
- -1 hexafluorophosphate Chemical compound 0.000 claims description 39
- 229910052697 platinum Inorganic materials 0.000 claims description 35
- 239000002904 solvent Substances 0.000 claims description 18
- 239000003093 cationic surfactant Substances 0.000 claims description 17
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 15
- 239000004094 surface-active agent Substances 0.000 claims description 15
- 238000002156 mixing Methods 0.000 claims description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 238000006116 polymerization reaction Methods 0.000 claims description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 8
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 claims description 8
- 125000003963 dichloro group Chemical group Cl* 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 239000000654 additive Substances 0.000 claims description 7
- 230000000996 additive effect Effects 0.000 claims description 7
- 229910052703 rhodium Inorganic materials 0.000 claims description 7
- 239000010948 rhodium Substances 0.000 claims description 7
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 7
- 229910052707 ruthenium Inorganic materials 0.000 claims description 7
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 claims description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 6
- 238000009833 condensation Methods 0.000 claims description 6
- 230000005494 condensation Effects 0.000 claims description 6
- 239000004912 1,5-cyclooctadiene Substances 0.000 claims description 5
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- 239000000377 silicon dioxide Substances 0.000 claims description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- LJSQFQKUNVCTIA-UHFFFAOYSA-N diethyl sulfide Chemical compound CCSCC LJSQFQKUNVCTIA-UHFFFAOYSA-N 0.000 claims description 4
- RCNRJBWHLARWRP-UHFFFAOYSA-N ethenyl-[ethenyl(dimethyl)silyl]oxy-dimethylsilane;platinum Chemical compound [Pt].C=C[Si](C)(C)O[Si](C)(C)C=C RCNRJBWHLARWRP-UHFFFAOYSA-N 0.000 claims description 4
- SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 claims description 4
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 claims description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 4
- VYXHVRARDIDEHS-UHFFFAOYSA-N 1,5-cyclooctadiene Chemical compound C1CC=CCCC=C1 VYXHVRARDIDEHS-UHFFFAOYSA-N 0.000 claims description 3
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 3
- 238000005119 centrifugation Methods 0.000 claims description 3
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical group OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 claims description 3
- 150000004687 hexahydrates Chemical class 0.000 claims description 3
- 229910052741 iridium Inorganic materials 0.000 claims description 3
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052762 osmium Inorganic materials 0.000 claims description 3
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims description 3
- 229910052763 palladium Inorganic materials 0.000 claims description 3
- 239000002562 thickening agent Substances 0.000 claims description 3
- 150000003606 tin compounds Chemical class 0.000 claims description 3
- UUERTZXRKZEANK-UHFFFAOYSA-L (2-azanidylcyclohexyl)azanide;dichloroplatinum(2+) Chemical compound C1CCCC2N[Pt](Cl)(Cl)NC21 UUERTZXRKZEANK-UHFFFAOYSA-L 0.000 claims description 2
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 claims description 2
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
- 229910002651 NO3 Inorganic materials 0.000 claims description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 229910000929 Ru alloy Inorganic materials 0.000 claims description 2
- 239000007983 Tris buffer Substances 0.000 claims description 2
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims description 2
- CLBRCZAHAHECKY-UHFFFAOYSA-N [Co].[Pt] Chemical compound [Co].[Pt] CLBRCZAHAHECKY-UHFFFAOYSA-N 0.000 claims description 2
- YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 claims description 2
- NDWWOISDNSYBCH-UHFFFAOYSA-L benzene;dichlororuthenium Chemical class Cl[Ru]Cl.C1=CC=CC=C1 NDWWOISDNSYBCH-UHFFFAOYSA-L 0.000 claims description 2
- PNPBGYBHLCEVMK-UHFFFAOYSA-L benzylidene(dichloro)ruthenium;tricyclohexylphosphane Chemical compound Cl[Ru](Cl)=CC1=CC=CC=C1.C1CCCCC1P(C1CCCCC1)C1CCCCC1.C1CCCCC1P(C1CCCCC1)C1CCCCC1 PNPBGYBHLCEVMK-UHFFFAOYSA-L 0.000 claims description 2
- PNPBGYBHLCEVMK-UHFFFAOYSA-N benzylidene(dichloro)ruthenium;tricyclohexylphosphanium Chemical compound Cl[Ru](Cl)=CC1=CC=CC=C1.C1CCCCC1[PH+](C1CCCCC1)C1CCCCC1.C1CCCCC1[PH+](C1CCCCC1)C1CCCCC1 PNPBGYBHLCEVMK-UHFFFAOYSA-N 0.000 claims description 2
- FSKLOGLSYZIRMP-UHFFFAOYSA-N carbanide 2-methylcyclopenta-1,3-diene platinum(4+) Chemical compound [CH3-].[CH3-].[CH3-].[Pt+4].CC=1C=C[CH-]C=1 FSKLOGLSYZIRMP-UHFFFAOYSA-N 0.000 claims description 2
- 229920006317 cationic polymer Polymers 0.000 claims description 2
- 150000001805 chlorine compounds Chemical class 0.000 claims description 2
- HOXDXGRSZJEEKN-UHFFFAOYSA-N cycloocta-1,5-diene;rhodium Chemical compound [Rh].C1CC=CCCC=C1 HOXDXGRSZJEEKN-UHFFFAOYSA-N 0.000 claims description 2
- VVAOPCKKNIUEEU-PHFPKPIQSA-L dichloro(cycloocta-1,5-diene)platinum(ii) Chemical compound Cl[Pt]Cl.C\1C\C=C/CC\C=C/1 VVAOPCKKNIUEEU-PHFPKPIQSA-L 0.000 claims description 2
- SPGAMGILENUIOF-UHFFFAOYSA-N dioxoplatinum;hydrate Chemical compound O.O=[Pt]=O SPGAMGILENUIOF-UHFFFAOYSA-N 0.000 claims description 2
- LDMNYTKHBHFXNG-UHFFFAOYSA-H disodium;platinum(4+);hexahydroxide Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Na+].[Na+].[Pt+4] LDMNYTKHBHFXNG-UHFFFAOYSA-H 0.000 claims description 2
- RZUASTIKPBCXPU-UHFFFAOYSA-N ethene;platinum;triphenylphosphane Chemical compound [Pt].C=C.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RZUASTIKPBCXPU-UHFFFAOYSA-N 0.000 claims description 2
- 239000000945 filler Substances 0.000 claims description 2
- JEGUKCSWCFPDGT-UHFFFAOYSA-N h2o hydrate Chemical compound O.O JEGUKCSWCFPDGT-UHFFFAOYSA-N 0.000 claims description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- HVOYZOQVDYHUPF-UHFFFAOYSA-N n,n',n'-trimethylethane-1,2-diamine Chemical compound CNCCN(C)C HVOYZOQVDYHUPF-UHFFFAOYSA-N 0.000 claims description 2
- 150000002978 peroxides Chemical class 0.000 claims description 2
- CLSUSRZJUQMOHH-UHFFFAOYSA-L platinum dichloride Chemical compound Cl[Pt]Cl CLSUSRZJUQMOHH-UHFFFAOYSA-L 0.000 claims description 2
- CFQCIHVMOFOCGH-UHFFFAOYSA-N platinum ruthenium Chemical compound [Ru].[Pt] CFQCIHVMOFOCGH-UHFFFAOYSA-N 0.000 claims description 2
- PIZSEPSUZMIOQF-UHFFFAOYSA-N platinum;2,4,6,8-tetrakis(ethenyl)-2,4,6,8-tetramethyl-1,3,5,7,2,4,6,8-tetraoxatetrasilocane Chemical compound [Pt].C=C[Si]1(C)O[Si](C)(C=C)O[Si](C)(C=C)O[Si](C)(C=C)O1 PIZSEPSUZMIOQF-UHFFFAOYSA-N 0.000 claims description 2
- ZPDKYCGMUSHWKZ-UHFFFAOYSA-N platinum;pyridine;dihydrochloride Chemical compound Cl.Cl.[Pt].C1=CC=NC=C1.C1=CC=NC=C1 ZPDKYCGMUSHWKZ-UHFFFAOYSA-N 0.000 claims description 2
- SYKXNRFLNZUGAJ-UHFFFAOYSA-N platinum;triphenylphosphane Chemical compound [Pt].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 SYKXNRFLNZUGAJ-UHFFFAOYSA-N 0.000 claims description 2
- RJQWVEJVXWLMRE-UHFFFAOYSA-N platinum;tritert-butylphosphane Chemical compound [Pt].CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C RJQWVEJVXWLMRE-UHFFFAOYSA-N 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- DCEGWIMEFFONKJ-UHFFFAOYSA-K potassium;ethene;trichloroplatinum(1-);hydrate Chemical compound O.[Cl-].[Cl-].[Cl-].[K+].[Pt+2].C=C DCEGWIMEFFONKJ-UHFFFAOYSA-K 0.000 claims description 2
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 claims description 2
- FBEIPJNQGITEBL-UHFFFAOYSA-J tetrachloroplatinum Chemical compound Cl[Pt](Cl)(Cl)Cl FBEIPJNQGITEBL-UHFFFAOYSA-J 0.000 claims description 2
- SLIOYUPLNYLSSR-UHFFFAOYSA-J tetrachloroplatinum;hydrate;dihydrochloride Chemical compound O.Cl.Cl.Cl[Pt](Cl)(Cl)Cl SLIOYUPLNYLSSR-UHFFFAOYSA-J 0.000 claims description 2
- 239000011995 wilkinson's catalyst Substances 0.000 claims description 2
- UTODFRQBVUVYOB-UHFFFAOYSA-P wilkinson's catalyst Chemical compound [Cl-].C1=CC=CC=C1P(C=1C=CC=CC=1)(C=1C=CC=CC=1)[Rh+](P(C=1C=CC=CC=1)(C=1C=CC=CC=1)C=1C=CC=CC=1)P(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 UTODFRQBVUVYOB-UHFFFAOYSA-P 0.000 claims description 2
- 239000012071 phase Substances 0.000 description 61
- 239000003921 oil Substances 0.000 description 50
- 239000011162 core material Substances 0.000 description 28
- 239000000725 suspension Substances 0.000 description 12
- 238000003756 stirring Methods 0.000 description 9
- 239000002280 amphoteric surfactant Substances 0.000 description 8
- 239000002736 nonionic surfactant Substances 0.000 description 8
- 239000002685 polymerization catalyst Substances 0.000 description 8
- 125000002091 cationic group Chemical group 0.000 description 7
- 229920001296 polysiloxane Polymers 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 6
- 230000008901 benefit Effects 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 235000014113 dietary fatty acids Nutrition 0.000 description 6
- 239000000194 fatty acid Substances 0.000 description 6
- 229930195729 fatty acid Natural products 0.000 description 6
- 229920001223 polyethylene glycol Polymers 0.000 description 6
- 239000002202 Polyethylene glycol Substances 0.000 description 5
- 150000001412 amines Chemical group 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 150000002430 hydrocarbons Chemical group 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000003125 aqueous solvent Substances 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 238000005538 encapsulation Methods 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 239000007764 o/w emulsion Substances 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- SGVYKUFIHHTIFL-UHFFFAOYSA-N 2-methylnonane Chemical compound CCCCCCCC(C)C SGVYKUFIHHTIFL-UHFFFAOYSA-N 0.000 description 3
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 3
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- 150000005215 alkyl ethers Chemical class 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- WOWHHFRSBJGXCM-UHFFFAOYSA-M cetyltrimethylammonium chloride Chemical group [Cl-].CCCCCCCCCCCCCCCC[N+](C)(C)C WOWHHFRSBJGXCM-UHFFFAOYSA-M 0.000 description 3
- 238000006482 condensation reaction Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 3
- 239000004205 dimethyl polysiloxane Substances 0.000 description 3
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 3
- 238000004945 emulsification Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 230000002209 hydrophobic effect Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000000600 sorbitol Substances 0.000 description 3
- CMCBDXRRFKYBDG-UHFFFAOYSA-N 1-dodecoxydodecane Chemical compound CCCCCCCCCCCCOCCCCCCCCCCCC CMCBDXRRFKYBDG-UHFFFAOYSA-N 0.000 description 2
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 2
- GXDHCNNESPLIKD-UHFFFAOYSA-N 2-methylhexane Natural products CCCCC(C)C GXDHCNNESPLIKD-UHFFFAOYSA-N 0.000 description 2
- MWRSABPHNREIIX-UHFFFAOYSA-N 9,9-dimethyldecan-1-ol Chemical class CC(C)(C)CCCCCCCCO MWRSABPHNREIIX-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 229920001214 Polysorbate 60 Polymers 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 229920001400 block copolymer Polymers 0.000 description 2
- 230000001186 cumulative effect Effects 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 238000007720 emulsion polymerization reaction Methods 0.000 description 2
- BITPLIXHRASDQB-UHFFFAOYSA-N ethenyl-[ethenyl(dimethyl)silyl]oxy-dimethylsilane Chemical class C=C[Si](C)(C)O[Si](C)(C)C=C BITPLIXHRASDQB-UHFFFAOYSA-N 0.000 description 2
- 238000011066 ex-situ storage Methods 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 125000003976 glyceryl group Chemical group [H]C([*])([H])C(O[H])([H])C(O[H])([H])[H] 0.000 description 2
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 238000002386 leaching Methods 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 description 2
- 150000003333 secondary alcohols Chemical class 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- BJAARRARQJZURR-UHFFFAOYSA-N trimethylazanium;hydroxide Chemical compound O.CN(C)C BJAARRARQJZURR-UHFFFAOYSA-N 0.000 description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical class C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- QNGQBCXQVIHJEM-UHFFFAOYSA-N 2-dodecyl-2-methyl-1,3,5,7,9,11-hexaoxa-2,4,6,8,10,12-hexasilacyclododecane Chemical compound CCCCCCCCCCCC[Si]1(C)O[SiH2]O[SiH2]O[SiH2]O[SiH2]O[SiH2]O1 QNGQBCXQVIHJEM-UHFFFAOYSA-N 0.000 description 1
- RFVNOJDQRGSOEL-UHFFFAOYSA-N 2-hydroxyethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCO RFVNOJDQRGSOEL-UHFFFAOYSA-N 0.000 description 1
- GTJOHISYCKPIMT-UHFFFAOYSA-N 2-methylundecane Chemical compound CCCCCCCCCC(C)C GTJOHISYCKPIMT-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical class CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 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 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 229910008051 Si-OH Inorganic materials 0.000 description 1
- 229910006358 Si—OH Inorganic materials 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 229910052770 Uranium Inorganic materials 0.000 description 1
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 1
- FGPCETMNRYMFJR-UHFFFAOYSA-L [7,7-dimethyloctanoyloxy(dimethyl)stannyl] 7,7-dimethyloctanoate Chemical compound CC(C)(C)CCCCCC(=O)O[Sn](C)(C)OC(=O)CCCCCC(C)(C)C FGPCETMNRYMFJR-UHFFFAOYSA-L 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 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
- 230000002378 acidificating effect Effects 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- UHWHEIKTDHONME-UHFFFAOYSA-M benzyl-decyl-dimethylazanium;hydroxide Chemical compound [OH-].CCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 UHWHEIKTDHONME-UHFFFAOYSA-M 0.000 description 1
- YDLDFMRKAOZXPN-UHFFFAOYSA-M benzyl-dimethyl-octylazanium;hydroxide Chemical compound [OH-].CCCCCCCC[N+](C)(C)CC1=CC=CC=C1 YDLDFMRKAOZXPN-UHFFFAOYSA-M 0.000 description 1
- 229960003237 betaine Drugs 0.000 description 1
- FSIJKGMIQTVTNP-UHFFFAOYSA-N bis(ethenyl)-methyl-trimethylsilyloxysilane Chemical compound C[Si](C)(C)O[Si](C)(C=C)C=C FSIJKGMIQTVTNP-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- MRUAUOIMASANKQ-UHFFFAOYSA-N cocamidopropyl betaine Chemical compound CCCCCCCCCCCC(=O)NCCC[N+](C)(C)CC([O-])=O MRUAUOIMASANKQ-UHFFFAOYSA-N 0.000 description 1
- 229940073507 cocamidopropyl betaine Drugs 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000013270 controlled release Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- WJTCGQSWYFHTAC-UHFFFAOYSA-N cyclooctane Chemical compound C1CCCCCCC1 WJTCGQSWYFHTAC-UHFFFAOYSA-N 0.000 description 1
- 239000004914 cyclooctane Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- KZOIWQKIVZDOGH-UHFFFAOYSA-M didodecyl(dimethyl)azanium;hydroxide Chemical compound [OH-].CCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCC KZOIWQKIVZDOGH-UHFFFAOYSA-M 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 229940008099 dimethicone Drugs 0.000 description 1
- VBVQYGNPGUXBIS-UHFFFAOYSA-M dimethyl(dioctadecyl)azanium;hydroxide Chemical compound [OH-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC VBVQYGNPGUXBIS-UHFFFAOYSA-M 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical class CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- JVQOASIPRRGMOS-UHFFFAOYSA-M dodecyl(trimethyl)azanium;hydroxide Chemical compound [OH-].CCCCCCCCCCCC[N+](C)(C)C JVQOASIPRRGMOS-UHFFFAOYSA-M 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 150000002332 glycine derivatives Chemical class 0.000 description 1
- 229930182470 glycoside Natural products 0.000 description 1
- 150000002338 glycosides Chemical class 0.000 description 1
- 238000003988 headspace gas chromatography Methods 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- WJLUBOLDZCQZEV-UHFFFAOYSA-M hexadecyl(trimethyl)azanium;hydroxide Chemical compound [OH-].CCCCCCCCCCCCCCCC[N+](C)(C)C WJLUBOLDZCQZEV-UHFFFAOYSA-M 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
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000002462 imidazolines Chemical class 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- VKPSKYDESGTTFR-UHFFFAOYSA-N isododecane Natural products CC(C)(C)CC(C)CC(C)(C)C VKPSKYDESGTTFR-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- HMMGMWAXVFQUOA-UHFFFAOYSA-N octamethylcyclotetrasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 HMMGMWAXVFQUOA-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-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
- 229940049964 oleate Drugs 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 150000003961 organosilicon compounds Chemical class 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005003 perfluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 150000003057 platinum Chemical class 0.000 description 1
- 229920001983 poloxamer Polymers 0.000 description 1
- 229920001987 poloxamine Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920000259 polyoxyethylene lauryl ether Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 1
- 239000002210 silicon-based material Substances 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003445 sucroses Chemical class 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- STYCVOUVPXOARC-UHFFFAOYSA-M trimethyl(octyl)azanium;hydroxide Chemical compound [OH-].CCCCCCCC[N+](C)(C)C STYCVOUVPXOARC-UHFFFAOYSA-M 0.000 description 1
- 239000007762 w/o emulsion Substances 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical class [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
- B01J13/02—Making microcapsules or microballoons
- B01J13/06—Making microcapsules or microballoons by phase separation
- B01J13/14—Polymerisation; cross-linking
- B01J13/18—In situ polymerisation with all reactants being present in the same phase
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J33/00—Protection of catalysts, e.g. by coating
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/02—Impregnation, coating or precipitation
- B01J37/0215—Coating
- B01J37/0219—Coating the coating containing organic compounds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/06—Halogens; Compounds thereof
- B01J27/128—Halogens; Compounds thereof with iron group metals or platinum group metals
- B01J27/13—Platinum group metals
-
- B01J35/40—
Definitions
- the present invention relates to encapsulated catalysts, processes for preparing the encapsulated catalysts and for curing a composition comprising the encapsulated catalyst, and one-part compositions comprising the encapsulated catalysts. More particularly, the present invention relates to microcapsules encapsulating catalysts in a shell of a silicon- based network polymer, processes for preparing the microcapsules and for curing a composition comprising the microcapsules, and one-part compositions comprising the microcapsules.
- Encapsulation techniques based on silicate shell having an organic core are known.
- International published application WO2003/066209 describes an encapsulation process by ex-situ emulsion polymerization from tetraalkoxysilanes.
- International published application WO2010/077774 describes microcapsules having a burst aid.
- the microcapsules In order to use encapsulated catalysts in systems that require catalysts, the microcapsules must be rigid enough to withstand processing and remain stable in order not to leak out or release the catalysts prematurely. The microcapsules must be compatible and miscible in the systems.
- microcapsules must be breakable in a controlled manner so that the catalysts can be released at the desirable time.
- Such release mechanisms are needed for certain applications such as in coatings or adhesives in electronic and health care applications. Therefore, there still remains a need for microcapsules encapsulating catalysts that are stable and rigid and easily made compatible, but at the same time able to release the catalysts in a controlled manner.
- the present invention provides microcapsules encapsulating catalysts in a shell of a silicon-based network polymer, processes for preparing the microcapsules and for curing a composition comprising the microcapsules, and one-part compositions comprising the microcapsules.
- the present invention provides processes for preparing microcapsules encapsulating a catalyst, the processes comprising: A. forming an aqueous emulsion comprising particles having the catalyst, an aqueous continuous phase, and an interface between the particles and the aqueous continuous phase;
- microcapsules comprising a core having the catalyst surrounded by a shell of a silicon-based network polymer and having from 0 to 1 % of water based on the weight of the microcapsules.
- the present invention provides processes for curing a composition, the processes comprising:
- microcapsules encapsulating catalysts, wherein the microcapsules comprise a core having a hydrosilylation catalyst surrounded by a shell of a silicon-based network polymer and the microcapsules have from 0 to 1 % water based on the weight of the microcapsules;
- the present invention provides encapsulated catalyst compositions, the compositions comprising microcapsules comprising a core having a catalyst surrounded by a shell of a silicon-based network polymer, wherein the
- microcapsules have a mean diameter size from 20 nm to 100 ⁇ and the microcapsules are impermeable to the catalyst so that the catalyst does not leak out of the microcapsules but is released upon rupturing of the microcapsules, and the compositions comprise from 0 to 1 % water based on the weight of the microcapsules.
- the present invention provides one-part compositions for making a hydrosilylation product, the one-part compositions comprising microcapsules encapsulating catalysts, alkenyl-functional polyorganosiloxane, and SiH-functional polyorganosiloxane, optionally an additive, wherein the one-part compositions are free of cure inhibitors.
- ranges includes the range itself and also anything subsumed therein, as well as endpoints.
- disclosure of a range of 2.0 to 4.0 includes not only the range of 2.0 to 4.0, but also 2.1 , 2.3, 3.4, 3.5, and 4.0 individually, as well as any other number subsumed in the range.
- disclosure of a range of, for example, 2.0 to 4.0 includes the subsets of, for example, 2.1 to 3.5, 2.3 to 3.4, 2.6 to 3.7, and 3.8 to 4.0, as well as any other subset subsumed in the range.
- the disclosure of Markush groups includes the entire group and also any individual members and subgroups subsumed therein.
- a hydrogen atom, an alkyl group, an aryl group, an aralkyl group, or an alkaryl group includes the member alkyl individually; the subgroup alkyl and aryl; and any other individual member and subgroup subsumed therein.
- substituted as used in relation to another group, for example, a hydrocarbon group, means, unless indicated otherwise, one or more hydrogen atoms in the hydrocarbon group has been replaced with another substituent.
- substituents include, for example, halogen atoms such as chlorine, fluorine, bromine, and iodine; halogen atom containing groups such as chloromethyl, perfluorobutyl, trifluoroethyl, and nonafluorohexyl; oxygen atoms; oxygen atom containing groups such as (meth)acrylic and carboxyl; nitrogen atoms; nitrogen atom containing groups such as amines, amino- functional groups, amido-functional groups, and cyano-functional groups; sulphur atoms; and sulphur atom containing groups such as mercapto groups.
- the present invention provides processes for preparing microcapsules encapsulating a catalyst, the processes comprising:
- microcapsules comprising a core having the catalyst surrounded by a shell of a silicon-based network polymer and having from 0 to 1 % of water based on the weight of the microcapsules.
- the catalyst in the aqueous emulsion may be one type of catalyst or more than one type of catalyst.
- the catalyst in the aqueous emulsion may be from 0.001 to 20.0 %, alternatively from 0.001 to 15.0 %, alternatively from 0.001 to 10.0 %, alternatively from 0.001 to 8.0 %, alternatively from 0.001 to 5.0 %, alternatively from 0.001 to 3.0 %, or alternatively from 0.001 to 1 .0 % based on the weight of the emulsion.
- the catalyst may be emulsified in an aqueous medium in the presence of a surfactant to form the aqueous emulsion.
- the surfactant may be a cationic surfactant so that the aqueous emulsion has a positive zeta-potential.
- the water reactive silicon compound comprises at least one silicon-bonded hydrolyzable group per molecule.
- the water reactive silicon compound comprises an average of more than 2 silicon-bonded hydrolyzable groups per molecule.
- the hydrolyzable group on the water reactive silicon compound may be an alkoxy group.
- the water reactive silicon compound comprises monoalkoxysilane, dialkoxysilane, alkyltrialkoxysilane wherein the alkyl group is substituted or unsubstituted, tetraalkoxylsilane, or any combination thereof.
- the water reactive silicon compound comprises tetraethyl orthosilicate.
- the silicon- based network polymer is silica or an organo-modified silica, such as, but not limited to, organo-modified silsesquioxane, alkylsilsesquioxane or aminosilsequioxane.
- a catalyst for the polymerization of the water reactive silicon compound is added to the emulsion before, during or after the addition of the water-reactive silicon compound.
- the catalyst maybe an organic tin compound.
- the aqueous emulsion may be passed through a high shear mixer before addition of the water-reactive silicon compound.
- a thickener may be added to the aqueous emulsion before addition of the tetraalkoxysilane.
- the microcapsules have a mean diameter size from 20 nm to 100 ⁇ , alternatively 1 ⁇ to 50 ⁇ , alternatively 1 ⁇ to 25 ⁇ , alternatively 1 ⁇ to 10 ⁇ , or alternatively 1 ⁇ to 5 ⁇ , or alternatively 0.5 ⁇ to 50 ⁇ , alternatively 0.5 ⁇ to 25 ⁇ , alternatively 0.5 ⁇ to 10 ⁇ , or alternatively 0.5 ⁇ to 5 ⁇ .
- the microcapsules may be post-treated with cationic polymer.
- the microcapsules in the aqueous medium may further be processed by concentrating the microcapsules; mixing the concentrated microcapsules with a solvent; and separating the microcapsules from the solvent to obtain microcapsules comprising a core having the catalyst surrounded by a shell of a silicon-based network polymer and having from 0 to 1 % of water based on the weight of the microcapsules.
- the mixing of the concentrated microcapsules with the solvent, and separating the microcapsules from the solvent may be carried out at least one time or at least two times.
- the solvent is one that is miscible in water and in polyorganosiloxane, such as, dipropylene glycol and glycerol.
- microcapsules comprising from 0 to 1 % by weight of water may be mixed with a polyorganosiloxane, functionalized polyorganosiloxane and/or an additive.
- the functionalized polyorganosiloxane may be vinyl-functional polyorganosiloxane or SiH- functional polyorganosiloxane.
- the additive includes, but is not limited to, a filler, such as, silica, silicone resins or calcium carbonate, diluents, preservatives, freeze thaw stabilizers, or inorganic salts to buffer pH.
- the microcapsules may have a payload load capacity from 1 to 99.99% by volume of the microcapsule.
- the payload capacity may be from 90 to 99%, or alternatively 95 to 98% by volume of the microcapsule.
- the microcapsules are impermeable to the catalyst so that the catalyst does not leak out of the microcapsules.
- the catalyst can be released upon rupturing of the microcapsules.
- the catalyst may be a hydrosilylation catalyst, a condensation catalyst or a peroxide catalyst.
- the hydrosilylation catalyst is selected from the group consisting of platinium, ruthenium, rhodium, palladium , osmium, iridium, complexes thereof, and any combinations thereof.
- the present invention provides processes for curing compositions, the processes comprising:
- microcapsules encapsulating catalysts, wherein the microcapsules comprise a core having a hydrosilylation catalyst surrounded by a shell of a silicon-based network polymer and the microcapsules have from 0 to 1 % water based on the weight of the microcapsules;
- the present invention provides encapsulated catalyst compositions, the compositions comprising microcapsules comprising a core having a catalyst surrounded by a shell of a silicon-based network polymer, wherein the
- microcapsules have a mean diameter size from 20 nm to 100 ⁇ and the microcapsules are impermeable to the catalyst so that the catalyst does not leak out of the microcapsules but is released upon rupturing of the microcapsules, and the composition have from 0 to 1 % water based on the weight of the microcapsules.
- the present invention provides one-part compositions for making a hydrosilylation product, the one-part compositions comprising the microcapsules encapsulating catalysts, alkenyl-functional polyorganosiloxane, and SiH-functional polyorganosiloxane, optionally an additive, wherein the one-part composition is free of a cure inhibitor or comprises a cure inhibitor.
- the present invention provides processes for preparing microcapsules encapsulating a catalyst, the processes comprising a step of forming an aqueous emulsion comprising particles having the catalyst, an aqueous continuous phase, and an interface between the particles and the aqueous continuous phase; adding a water reactive silicon compound to the aqueous continuous phase; polymerizing the water reactive silicon compound at the interface of the particles and the continuous phase to obtain microcapsules comprising a core having the catalyst surrounded by a shell of a silicon-based network polymer in an aqueous medium.
- the core of the microcapsules that is, the material surrounded by the shell comprising a silicon-based network polymer, is also referred to as the "oil phase.”
- the oil phase encompasses the catalyst and any other compound, or mixture of compounds that is hydrophobic.
- the oil phase is liquid when forming the oil in water emulsions.
- the oil phase may contain any organic, silicone, or fluorocarbon based oil, or any combination thereof.
- the oil phase may also contain any solvent or diluent, which may be added for the purpose of solubilizing a solid hydrophobic compounds and/or the catalyst to create the liquid oil phase during formation of the aqueous emulsion.
- the catalyst in the microcapsules may be released upon rupturing of the
- a burst aid may be added to the oil phase so that upon formation of the microcapsules the burst aid is trapped in the core.
- the burst aid encompasses any compound, or mixture of compounds added to the oil phase.
- the burst aids may be selected from volatile hydrophobic organic or siloxane compounds.
- the burst aid may be a volatile linear hydrocarbons, including but not limited to, pentane, hexane, heptane, octane, nonane; volatile cyclic hydrocarbons such as cyclopentane, cyclohexane, cycloheptane, cyclooctane; volatile branched hydrocarbons such as isohexane, isoheptane, isooctane, isodecane, isododecane; volatile linear siloxanes, including but not limited to, hexamethyldisiloxane, decamethyltetrasiloxane; and volatile cyclic siloxanes such as octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, dodecylmethylcyclohexasiloxane.
- volatile linear hydrocarbons including but not limited to, pentane, hexane, h
- the trigger temperature may be from 40 S C to - ⁇ 50 °C, alternatively from 40 °C to 130 °C, alternatively from 40 °C to ' ⁇ 20 °C, alternatively from 40 °C to 1 10 °C, alternatively from 40 °C to - ⁇ 00 °C , alternatively from 40 °C to 100 °C, alternatively form 40 °C to 90 °C, alternatively from 40 °C to 80 °C, alternatively from 40 °C to 70 °C, alternatively from 40 °C to 60 °C, alternatively from 40°C to 50 °C, alternatively from 50 °C to 70 °C, alternatively from 55°C to 60 °C, alternatively form 60 °C to 95 °C, alternatively from 60 °C to 90 °C, alternatively from 40 S C to - ⁇ 50 °C, alternatively from 40 °C to 130 °C, alternatively from 40 °C to ' ⁇ 20 °C, alternative
- Heating causes an increase in the vapor pressure of the burst aid, which
- the amount of burst aid added to the oil phase, present in the microcapsules as a percentage of the oil phase weight prior to encapsulation is from 0.1 to 50%, alternatively from 0.1 to 40%, alternatively from 0.1 to 30%, alternatively from 0.1 to 20%, alternatively from 0.1 to 10%, alternatively from 0.2 to 40%, alternatively from 0.2 to 30%, alternatively from 0.2 to 20%, or alternatively from 0.2 to 10%.
- the catalyst in the microcapsules may be released upon rupturing of the microcapsules after exposure to shear, such as, but not limited to, a shear rate of 1000/sec or higher.
- the core of the microcapsule comprises a hydrosilylation catalyst.
- the hydrosilylation catalyst may be present together with the burst aid in the core.
- the hydrosilylation catalyst may be selected from any platinum group metal-containing catalysts.
- platinum group it is meant ruthenium, rhodium, palladium, osmium, iridium and platinum and complexes thereof.
- Platinum group metal-containing catalysts are the platinum complexes prepared as described by Willing et al., U.S. Pat. No. 3,419,593, and Brown et al, U.S. Pat. No. 5,175,325, each of which is hereby incorporated by reference to show such complexes and their preparation.
- platinum-containing catalysts include chloroplatinic acid, either in hexahydrate form or anhydrous form, and/or a platinum-containing catalyst which is obtained by a method comprising reacting chloroplatinic acid with an aliphatically unsaturated organosilicon compound such as divinyltetramethyldisiloxane, or alkene- platinum-silyl complexes, such as (COD)Pt(SiMeCl2)2. where COD is 1 ,5-cyclooctadiene and Me is methyl.
- organosilicon compound such as divinyltetramethyldisiloxane
- alkene- platinum-silyl complexes such as (COD)Pt(SiMeCl2)2.
- the hydrosilylation catalyst is of the following:
- the oil phase is mixed with an aqueous solution of a surfactant.
- the surfactant may vary, but typically is chosen from those surfactants that enhance the formation of the aqueous emulsion.
- the surfactant in the aqueous emulsion may be present from 0.01 to 10.0 %, alternatively 0.01 to 8.0 %, alternatively 0.01 to 5.0 %, alternatively 0.01 to 3.0 %, alternatively 0.01 to 1 .0 %, alternatively 0.01 to 0.5 %, alternatively 0.1 to 0.5 % by weight of the emulsion.
- a cationic surfactant is used to form the aqueous emulsion, wherein the aqueous emulsion comprises a positive zeta-potential.
- the cationic surfactant in the aqueous emulsion may be present from 0.01 to 10.0 %, alternatively 0.01 to 8.0 %, alternatively 0.01 to 5.0 %, alternatively 0.01 to 3.0 %, alternatively 0.01 to 1 .0 %, alternatively 0.01 to 0.5 %, alternatively 0.1 to 0.5 % by weight of the aqueous emulsion.
- Cationic surfactants useful in the present invention include, but are not limited to, alkylamine salts, quaternary ammonium salts, sulphonium salts, phosphonium salts, quaternary ammonium hydroxides such as octyl trimethyl ammonium hydroxide, dodecyl trimethyl ammonium hydroxide, hexadecyl trimethyl ammonium hydroxide, octyl dimethyl benzyl ammonium hydroxide, decyl dimethyl benzyl ammonium hydroxide, didodecyl dimethyl ammonium hydroxide, dioctadecyl dimethyl ammonium hydroxide, tallow trimethyl ammonium hydroxide and coco trimethyl ammonium hydroxide as well as corresponding salts of these materials; fatty amines and fatty acid amides and their derivatives; basic pyridinium compounds; quaternary ammonium bases of benzimidazolines;
- a preferred cationic surfactant is cetyl trimethyl ammonium chloride.
- cationic surfactant examples include, but are not limited to, an amphoteric surfactant such as cocamidopropyl betaine, cocamidopropyl hydroxysulfate, cocobetaine, sodium cocoamidoacetate, cocodimethyl betaine, N-coco-3-aminobutyric acid, imidazolinium carboxyl compounds, imidazoline compounds, alkylaminoacid salts, betaines, N- alkylamidobetaines and derivatives thereof, proteins and derivatives thereof, glycine derivatives, sultaines, alkyl polyaminocarboxylates and alkylamphoacetates, and mixtures thereof.
- an amphoteric surfactant such as cocamidopropyl betaine, cocamidopropyl hydroxysulfate, cocobetaine, sodium cocoamidoacetate, cocodimethyl betaine, N-coco-3-aminobutyric acid, imidazolinium carboxyl compounds, imid
- the above surfactants may be used individually or in combination.
- the cationic or amphoteric surfactant is dissolved in water and the resulting aqueous solution used as a component in aqueous or continuous phase of the aqueous emulsion.
- a cationic or amphoteric surfactant promotes condensation and polymerisation of the tetraalkoxysilane at the interface of the emulsified droplets comprising the catalyst, leading to non-diffusive microcapsules.
- the tetraalkoxysilane hydrolyzes and condenses upon reacting in the emulsion.
- the anionically charged hydrolysis product is attracted to the cationic or amphoteric surfactant at the interface where it forms the silicon based polymer shell.
- the concentration of the cationic surfactant during the formation of the aqueous emulsion may be between 0.1 % and 0.3% by weight of the oil phase.
- the use of cationic or amphoteric surfactant during emulsification of the oil phase to provide a positive charge and/or the hydrolysis reaction of the water reactive silicon compound comprising a alkoxysilane and/or incorporation into the shell leads to microcapsules which are more resistant to diffusion or leaching of the oil phase from the microcapsules.
- the aqueous solution of the cationic or amphoteric surfactant may contain additional and/or optional components, providing they are water soluble.
- additional and/or optional components providing they are water soluble.
- a water-miscible organic solvent such as an alcohol or lactam may be added.
- Such components include, but is not limited to, surfactants, thickeners, preservatives, and antimicrobials.
- Additional surfactants include, but are not limited to, nonionic surfactants.
- Nonionic surfactants includes, but are not limited to, polyoxyalkylene alkyl ethers such as polyethylene glycol long chain (12-14 carbon atoms) alkyl ether, polyoxyalkylene sorbitan ethers, polyoxyalkylene alkoxylate esters, polyoxyalkylene alkylphenol ethers, ethylene glycol propylene glycol copolymers, polyvinyl alcohol and alkylpolysaccharides.
- polyoxyalkylene alkyl ethers such as polyethylene glycol long chain (12-14 carbon atoms) alkyl ether, polyoxyalkylene sorbitan ethers, polyoxyalkylene alkoxylate esters, polyoxyalkylene alkylphenol ethers, ethylene glycol propylene glycol copolymers, polyvinyl alcohol and alkylpolysaccharides.
- alkylpolysaccharides may have the formula R 1 -0-(R 2 0) m -(G) n wherein R 1 represents a linear or branched alkyl group, a linear or branched alkenyl group or an alkylphenyl group,
- R 2 represent an alkylene group
- G represents a reduced sugar
- m denotes 0 or a positive integer
- n represent a positive integer.
- alkylpolysaccharides are described in U.S. Patent No. 5,035,832.
- nonionic surfactants include, but are not limited to, condensates of ethylene oxide with long chain fatty alcohols or fatty acids such as a C12-16 alcohol, condensates of ethylene oxide with an amine or an amide, condensation products of ethylene and propylene oxide, esters of glycerol, sucrose, sorbitol, fatty acid alkylol amides, sucrose esters, fluoro-surfactants, fatty amine oxides, and mixtures thereof.
- nonionic surfactants include polyoxyethylene fatty alcohols such as
- polyoxyethylene sorbitan alkyl esters polyethylene glycol, polypropylene glycol, diethylene glycol, ethoxylated trimethylnonanols, polyoxyalkylene-substituted silicones (rake or ABn types), silicone alkanolamides, silicone esters, silicone glycosides, dimethicone copolyols, fatty acid esters of polyols, for instance sorbitol or glyceryl mono-, di-, tri- or sesquioleates or stearates, glyceryl or polyethylene glycol laurates; fatty acid esters of polyethylene glycol (polyethylene glycol monostearate or monolaurate); polyoxyethylenated fatty acid esters (stearate or oleate) of sorbitol; polyoxyethylenated alkyl (lauryl, cetyl, stearyl or octyl)ethers, and mixtures thereof.
- one nonionic surfactant may have a low Hydrophile-Lipophile Balance (HLB) and the other nonionic surfactant(s) may have a high HLB, such that the nonionic surfactants have a combined HLB of 1 1 -15, alternatively a combined HLB of 12.5-14.5.
- HLB Hydrophile-Lipophile Balance
- the oil phase and aqueous solution of the cationic or amphoteric surfactant are mixed together to form an aqueous emulsion (and oil-in-water emulsion). Mixing and emulsion formation may occur using any known techniques in the emulsion art. Typically, the oil phase and aqueous solution of the cationic or amphoteric surfactant are combined using simple stirring techniques to form an emulsion. Particle size of the aqueous emulsion may be reduced before addition of the water reactive silicon compound.
- emulsification devices in this invention include, but are not limited to, homogenizer, sonolator, rotor-stator turbines, colloid mill, microfluidizer, blades, helix and combination thereof.
- the particle size may be reduced to a range from 0.2 to 100 micrometers, or a range from 0.02 micrometers to 100 micrometers.
- the weight ratio of oil phase to aqueous phase in the emulsion can generally be between 40:1 and 1 :50, although the higher proportions of aqueous phase are economically disadvantageous particularly when forming a suspension of microcapsules.
- the weight ratio of oil phase to aqueous phase is between 2:1 and 1 :3.
- a phase inversion process can be used in which the oil phase is mixed with surfactant and a small amount of water, for example 2.5 to 10% by weight based on the oil phase, forming a water-in-oil emulsion which inverts to an oil-in-water emulsion as it is sheared. Further water can then be added to dilute the emulsion to the required concentration.
- microcapsules encapsulating catalysts involves adding a water reactive silicon compound to the aqueous emulsion, and polymerizing the water reactive silicon compound at the oil/water interface of the emulsion to obtain microcapsules comprising a core having the catalyst surrounded by a shell of a silicon-based network polymer.
- the third step involves an "ex-situ emulsion polymerization" by which the water reactive silicon compound hydrolyzes and condenses at the oil/water interface via a phase transfer of the water reactive silicon compound precursors leading to the formation of microcapsules having a core surrounded by a shell.
- the water reactive silicon compound comprises at least one silicon-bonded hydrolyzable group per molecule, or an average of more than 2 silicon-bonded hydrolyzable groups per molecule.
- the hydrolyzable groups on the water reactive silicon compound is any group capable of hydrolyzing and condensing to form a silicon-based network polymer.
- the hydrolyzable groups comprises alkoxy groups, acyloxy, or hydroxy groups, or any combination thereof.
- the water reactive silicon compound comprises monoalkoxysilane, dialkoxysilane, alkyltrialkoxysilane wherein the alkyl group has from 1 to 12 carbon atoms and is substituted or unsubstituted, tetraalkoxylsilane, or any combination thereof.
- the water reactive silicon compound comprises tetraethyl orthosilicate (tetraethoxysilane or TEOS).
- the tetraalkoxysilanes such as tetraethoxysilane, may be used in monomeric form or as a liquid partial condensate.
- the tetraalkoxysilane can be used in conjunction with one or more other water reactive silicon compound having at least two, preferably at least three, hydrolyzable groups bonded to silicon, for example, silanol Si-OH groups, an
- alkyltrialkoxysilane such as methyltrimethoxysilane or a liquid condensate of an
- the water reactive silicon compound may comprise 75-100% by weight tetraalkoxysilane and 0-25% trialkoxysilane.
- the alkyl moiety of the alkoxy groups in the tetraalkoxysilanes or other silanes contain 1 to 4 carbon atoms, most preferably 1 or 2 carbon atoms.
- the tetraalkoxysilane, and other water reactive silicon compound hydrolyzes and condenses to form a network polymer, that is, a three-dimensional network of silicon- based material around the emulsified droplets having the catalyst.
- the water reactive silicon compound preferably consists of at least 10%, and most preferably 90-100% tetraalkoxysilane. The inventors have found that use of
- tetraalkoxysilane such as tetraethoxysilane, forms impermeable microcapsules, forming a three-dimensional network consisting of S1O4/2 units.
- the tetraalkoxysilane, and other water reactive silicon compounds can be added to the aqueous emulsion as an undiluted liquid or as a solution in an organic solvent or in an emulsion form.
- the tetraalkoxysilane and aqueous emulsion are mixed, and subsequently polymerization of the tetraalkoxysilane forms the silicon-based network polymer shell on the surface of the emulsified droplets, encapsulating the catalyst.
- Mixing is typically effected with any stirring techniques. Common stirring techniques are typically sufficient to maintain the particle size of the starting aqueous emulsion while allowing the tetraalkoxysilane to polymerize and condense at the oil/water interface in the aqueous emulsion.
- the amount of tetraalkoxysilane added for the polymerization step typically ranges from 6:1 to 1 :13, alternatively from 1 .2:1 to 1 :7.3, alternatively from 1 .3 to 1 :6.1 based on the weight amount of oil phase present in the aqueous emulsion.
- the polymerization of the tetraalkoxysilane at the oil/water interface typically is a condensation reaction which may be conducted at acidic, neutral or basic pH.
- the condensation reaction is generally carried out at ambient temperature and pressure, but can be carried out at increased temperature, for example up to 95 °C, and increased or decreased pressure, for example under vacuum to strip the volatile alcohol produced during the condensation reaction.
- Any catalyst known to promote the polymerization of the water reactive silicon compound may be used to form the shell of the microcapsule.
- the catalyst may be a polymerization catalyst that promotes polymerization of tetraalkoxysilanes.
- polymerization catalyst may alternatively be added to the aqueous emulsion just before the addition of the water reactive silicon compound, or simultaneously with the water reactive silicon compound, or after the addition of the water reactive silicon compound, in which case the catalyst helps to harden and make more impervious the shell of silicon-based network polymer. Encapsulation can however be achieved without a polymerization catalyst.
- the polymerization catalyst includes, but is not limited to, an oil soluble organic metal compound, for example an organic tin compound, particularly an organotin compound such as a diorganotin diester, for example dimethyl tin di(neodecanoate), dibutyl tin dilaurate or dibutyl tin diacetate, or alternatively a tin carboxylate such as stannous octoate, or an organic titanium compound such as tetrabutyl titanate.
- An organotin catalyst can for example be used at 0.05 to 2% by weight based on the water reactive silicon compound.
- the polymerization catalyst may typically be present at 1 to 200 parts per million based on the combined weight of the aqueous emulsion.
- An organotin catalyst has the advantage of promoting catalysis at neutral pH.
- the polymerization catalyst is typically mixed with the oil phase components before emulsification to form the aqueous emulsion, as this promotes condensation of the water reactive silicon compound at the surface of the emulsified oil phase droplets.
- the polymerization catalyst when used, may be added undiluted, or as a solution in an organic solvent such as a hydrocarbon, alcohol or ketone, or as a mutiphasic system such as an emulsion or suspension.
- the polymerization catalyst may comprise an acid as a hydrolysis catalyst or a base as a condensation catalyst for the polymerization of the water reactive silicon compound.
- the polymerization of the water reactive silicon compound is allowed to proceed so as to form the shell of a microcapsule that is at least 18 nanometers thick, alternatively the shell has a thickness in the range of 18 to 150 nanometers, alternatively from 18 to 100 nanometers.
- Shell Thickness (nm) [(PS/2)-[(PS/2) * (Payload/100) 1 /3 ]] 000 where PS is the particle size (Dv 0.5) expressed in micrometers;
- This equation is based on the spherically shaped microcapsules having an average diameter as determined by their average particle size (Dv 0.5).
- the shell thickness is the difference between the radius of the microcapsule and the radius of the core material in the microcapsule.
- Shell thickness ( microcapsule - r core
- Payload represents the percentage of the microcapsule occupied by the core material, as determined by the amount of oil phase present in the aqueous emulsion.
- Payload is calculated by the relationship:
- Payload volume of the oil phase*100/(volume of the oil phase + volume of the shell)
- the volume of the oil phase is the mass of the oil phase divided by the density of the oil phase.
- the mass of the oil phase is the same as the amount added for making the aqueous emulsion.
- the volume of the shell is the mass of the shell divided by the density of silica.
- the silicon-based network polymer comprising the shell is expected to have an average chemical composition with the empirical formula SiC ⁇ -
- the density of the shell is estimated to be 2 g/mL, which approximates the density of silica (Si02).
- the mass of the shell is calculated from the amount of tetraalkoxysilane added. More specifically, the mass of the shell is based on the expected stoichiometric yield of silicon-based network polymer of empirical formula S1O2 given the type and amount of the tetraalkoxysilane used in the process.
- the tetraalkoxysilane is tetraethoxysilane having a density of 0.934 g/mL. In this embodiment, assuming complete hydrolysis and condensation, 1 g of tetraethoxysilane produces 0.288 g of S1O2 polymer network.
- the microcapsules After preparation of microcapsules encapsulating catalysts comprising a core having the catalyst surrounded by a shell of a silicon-based network polymer, the microcapsules are in an aqueous medium.
- the aqueous medium constitutes the aqueous continuous phase of the aqueous emulsion.
- the aqueous medium may be removed to produce microcapsules having reduced water content.
- the water content may be reduced to 1 % or less by weight.
- the microcapsules having reduced water content may be made by spray or freeze drying or any other methods for removing water, including, but not limited to, a solvent exchange procedure wherein water is replaced with a non-aqueous solvent.
- the microcapsules having reduced water content after removal of the aqueous medium, may be suspended in a solvent, for example, in a non-aqueous solvent.
- non-aqueous solvents include, but are not limited to, organic solvents or polyorganosiloxanes.
- the processes for preparing the microcapsules encapsulating catalysts further comprises concentrating the microcapsules, mixing the concentrated microcapsules with a solvent; and separating the microcapsules from the solvent to obtain microcapsules comprising a core having the catalyst surrounded by a shell of a silicon-based network polymer and having from 0 to 1 % of water based on the weight of the
- the concentrating and separating steps may be carried out by centrifugation or filtration.
- the solvent is any non-aqueous solvent that is miscible with water and polyorganosiloxanes.
- the solvent includes, but is not limited to, dipropylene glycol, glycerol, alcohols, polyethylene glycols, or acetones.
- Mastersizer S from Malvern Instruments Ltd., UK, and further information on the measuring particle sizes can be, for example, found in "Basic principles of particle size analytics", Dr. Alan Rawle, Malvern Instruments Limited, WR14 1 XZ, UK and the “Manual of Malvern Mastersizer S particle size analyzer". All particle sizes indicated in the present application are mean average volume particle size according to D(v, 0.5) and are measured with a Malvern Mastersizer S, if nothing else is stated or obvious.
- the particle size is obtained from a particle size distribution (PSD).
- PSD particle size distribution
- the PSD can be determined on a volume, surface, length basis.
- the volume particle size is equal to the diameter of the sphere that has the same volume as a given particle.
- Dv represents the average volume particle size of the dispersed particles.
- Dv90 is the particle size measured in volume corresponding to 90% of the cumulative particle population.
- the microcapsules according to the present invention are stable and inhibit diffusion or leaching of the catalysts from the microcapsules.
- the catalyst may be released from the microcapsules in a controlled rate of release.
- Suspension stabilization is determined by the amount of separation as measured as a percentage of the total suspension height over a six months timeframe.
- the active triggered release temperature for controlled release of the catalyst is determined by a headspace GC/MS analysis of the suspension tracking the presence of burst aid with increasing temperature.
- the microcapsules encapsulating catalysts prepared by the processes of the present invention exhibit advantages. One advantage is in hydrosilylation applications where a one- pot system can be used.
- microcapsules encapsulating catalysts of the present invention can avoid the use of cure inhibitors, or at least allow for using cheaper and weaker cure inhibitors.
- the microcapsules encapsulating catalysts of the present invention allows for simpler manufacturing processes, easier molding and casting products, improved adhesion, and consuming less energy.
- the microcapsules encapsulating catalysts of the present invention provide advantages for dual or multiply curing systems because microcapsules encapsulating different catalysts can be used in a curing system. Furthermore, the microcapsules encapsulating catalysts of the present invention are robust and withstand further processing and remain stable in a variety of silicone formulations.
- Example 1 Formulation of a microcapsule suspension.
- the oil phase was prepared by mixing 150 g of vinyterminated polydimethyl siloxane and 50 g of a composition such that the oil phase contained 0.35% of 1 ,3-Diethenyl-1 ,1 ,3,3 -Tetramethyldisiloxane Complexes (Platinum).
- a composition such that the oil phase contained 0.35% of 1 ,3-Diethenyl-1 ,1 ,3,3 -Tetramethyldisiloxane Complexes (Platinum).
- Platinum 1 ,3-Diethenyl-1 ,1 ,3,3 -Tetramethyldisiloxane Complexes
- Example 2 Formulation of a microcapsule suspension.
- the oil phase was prepared by mixing 150 g of vinyterminated polydimethyl siloxane and 50 g of a composition such that the oil phase contained 0.35% of 1 ,3-Diethenyl-1 ,1 ,3,3 -Tetramethyldisiloxane Complexes (Platinum).
- a composition such that the oil phase contained 0.35% of 1 ,3-Diethenyl-1 ,1 ,3,3 -Tetramethyldisiloxane Complexes (Platinum).
- 3.2 g of Arquad® 16-29 from AKZO-Nobel was mixed with 622 g of water until complete dissolution.
- the oil phase was added to that Arquad® 16-29 solution under stirring to form a coarse oil-in-water emulsion.
- the stable coarse emulsion was passed twice through an homogenizer to get a fine emulsion having a mean average particle size Dv0.5 of 3.8 ⁇ and a Dv0.9 of 10.4 ⁇
Abstract
La présente invention concerne des procédés pour préparer des micro-capsules encapsulant un catalyseur, le processus comprenant la formation d'une émulsion aqueuse comportant les particules ayant le catalyseur, une phase aqueuse continue et une interface entre les particules et la phase aqueuse continue ; l'ajout d'un composé de silicium réagissant avec l'eau à la phase aqueuse continue ; la polymérisation du composé de silicium réagissant avec l'eau au niveau de l'interface des particules et de la phase continue pour obtenir des micro-capsules comprenant un noyau ayant le catalyseur entouré par une enveloppe en polymère réticulé à base de silicium dans un milieu aqueux ; l'élimination du milieu aqueux pour obtenir des micro-capsules comportant un noyau ayant le catalyseur entouré par une enveloppe en polymère réticulé à base de silicium et ayant de 0 à 1 % d'eau sur la base du poids des micro-capsules. La présente invention concerne également des procédés de durcissement d'une composition, les processus comprenant des micro-capsules encapsulant des catalyseurs, des compositions de catalyseurs encapsulés comportant les micro-capsules encapsulant des catalyseurs et des compositions simples permettant la fabrication de produits d'hydrosilylation exempts d'inhibiteurs de durcissement.
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201562118481P | 2015-02-20 | 2015-02-20 | |
US62/118,481 | 2015-02-20 | ||
EP15305272 | 2015-02-20 | ||
EP15305272.5 | 2015-02-20 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2016133946A1 true WO2016133946A1 (fr) | 2016-08-25 |
Family
ID=52648960
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US2016/018147 WO2016133946A1 (fr) | 2015-02-20 | 2016-02-17 | Micro-capsules à catalyseurs encapsulés |
Country Status (1)
Country | Link |
---|---|
WO (1) | WO2016133946A1 (fr) |
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109082120A (zh) * | 2018-09-28 | 2018-12-25 | 华南协同创新研究院 | 一种弹性壳体微胶囊相变材料及其制备方法和应用 |
WO2019025002A1 (fr) | 2017-08-04 | 2019-02-07 | Wacker Chemie Ag | Stabilisation de catalyseurs à base de métal noble |
KR20190095222A (ko) * | 2019-08-05 | 2019-08-14 | 한국과학기술연구원 | 메탄올 또는 그 전구체 합성용 촉매, 이의 제조방법 및 이를 이용한 메탄올 또는 그 전구체의 제조방법 |
CN110291155A (zh) * | 2017-02-14 | 2019-09-27 | 信越化学工业株式会社 | 加成固化型有机硅组合物 |
CN110431189A (zh) * | 2017-03-27 | 2019-11-08 | 信越化学工业株式会社 | 加成固化型有机硅组合物 |
CN110903653A (zh) * | 2018-09-14 | 2020-03-24 | 浙江清华柔性电子技术研究院 | 硅橡胶组合物、硅橡胶及其制备方法 |
CN110903481A (zh) * | 2018-09-14 | 2020-03-24 | 浙江清华柔性电子技术研究院 | 微胶囊催化剂及其制备方法、应用 |
CN113416106A (zh) * | 2021-06-21 | 2021-09-21 | 山东农业大学 | 一种液化生物基包膜控释材料的制备方法 |
CN114058326A (zh) * | 2021-11-22 | 2022-02-18 | 烟台德邦科技股份有限公司 | 一种粘接及可靠性优异的有机聚硅氧烷组合物及其制备方法 |
CN114160204A (zh) * | 2021-12-08 | 2022-03-11 | 江西贝特利新材料有限公司 | 一种负载型铂催化剂及其制备方法 |
CN114292289A (zh) * | 2021-12-27 | 2022-04-08 | 江西贝特利新材料有限公司 | 一种1,3-双(3-氨基丙基)-1,1,3,3-四甲基二硅氧烷及其制备方法 |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20110236498A1 (en) * | 2008-12-17 | 2011-09-29 | Leon Andre Marteaux | Suspensions Of Silicate Shell Microcapsules For Temperature Controlled Release |
US8110284B2 (en) * | 2003-07-31 | 2012-02-07 | Sol-Gel Technologies Ltd. | Microcapsules loaded with active ingredients and a method for their preparation |
US20120101227A1 (en) * | 2009-07-01 | 2012-04-26 | Dow Corning Corporation | Microcapsules Containing Curable Siloxanes |
US20130210969A1 (en) * | 2010-06-02 | 2013-08-15 | MAX-PLANCK-Gesellschaft zur Förderung der Wissenschaften e.V. | Feedback active coatings with sensitive containers based on nano-, micro-, mini-, and macroemulsions of direct or reversed type |
US20140341956A1 (en) * | 2013-05-20 | 2014-11-20 | La Croix Co., Ltd. | Anti-uv composition for protecting scalp |
-
2016
- 2016-02-17 WO PCT/US2016/018147 patent/WO2016133946A1/fr active Application Filing
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8110284B2 (en) * | 2003-07-31 | 2012-02-07 | Sol-Gel Technologies Ltd. | Microcapsules loaded with active ingredients and a method for their preparation |
US20110236498A1 (en) * | 2008-12-17 | 2011-09-29 | Leon Andre Marteaux | Suspensions Of Silicate Shell Microcapsules For Temperature Controlled Release |
US20120101227A1 (en) * | 2009-07-01 | 2012-04-26 | Dow Corning Corporation | Microcapsules Containing Curable Siloxanes |
US20130210969A1 (en) * | 2010-06-02 | 2013-08-15 | MAX-PLANCK-Gesellschaft zur Förderung der Wissenschaften e.V. | Feedback active coatings with sensitive containers based on nano-, micro-, mini-, and macroemulsions of direct or reversed type |
US20140341956A1 (en) * | 2013-05-20 | 2014-11-20 | La Croix Co., Ltd. | Anti-uv composition for protecting scalp |
Cited By (22)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US11041064B2 (en) | 2017-02-14 | 2021-06-22 | Shin-Etsu Chemical Co., Ltd. | Addition-cure silicone composition |
TWI771370B (zh) * | 2017-02-14 | 2022-07-21 | 日商信越化學工業股份有限公司 | 加成硬化型聚矽氧組成物 |
CN110291155B (zh) * | 2017-02-14 | 2021-11-12 | 信越化学工业株式会社 | 加成固化型有机硅组合物 |
CN110291155A (zh) * | 2017-02-14 | 2019-09-27 | 信越化学工业株式会社 | 加成固化型有机硅组合物 |
US11028234B2 (en) * | 2017-03-27 | 2021-06-08 | Shin-Etsu Chemical Co., Ltd. | Addition-curable silicone composition |
CN110431189A (zh) * | 2017-03-27 | 2019-11-08 | 信越化学工业株式会社 | 加成固化型有机硅组合物 |
TWI737902B (zh) * | 2017-03-27 | 2021-09-01 | 日商信越化學工業股份有限公司 | 加成硬化型聚矽氧組成物 |
KR20190129115A (ko) * | 2017-03-27 | 2019-11-19 | 신에쓰 가가꾸 고교 가부시끼가이샤 | 부가 경화형 실리콘 조성물 |
KR102536773B1 (ko) * | 2017-03-27 | 2023-05-25 | 신에쓰 가가꾸 고교 가부시끼가이샤 | 부가 경화형 실리콘 조성물 |
CN110431189B (zh) * | 2017-03-27 | 2022-03-01 | 信越化学工业株式会社 | 加成固化型有机硅组合物 |
WO2019025002A1 (fr) | 2017-08-04 | 2019-02-07 | Wacker Chemie Ag | Stabilisation de catalyseurs à base de métal noble |
CN110903653A (zh) * | 2018-09-14 | 2020-03-24 | 浙江清华柔性电子技术研究院 | 硅橡胶组合物、硅橡胶及其制备方法 |
CN110903481A (zh) * | 2018-09-14 | 2020-03-24 | 浙江清华柔性电子技术研究院 | 微胶囊催化剂及其制备方法、应用 |
CN109082120B (zh) * | 2018-09-28 | 2021-06-01 | 华南协同创新研究院 | 一种弹性壳体微胶囊相变材料及其制备方法和应用 |
CN109082120A (zh) * | 2018-09-28 | 2018-12-25 | 华南协同创新研究院 | 一种弹性壳体微胶囊相变材料及其制备方法和应用 |
KR102137669B1 (ko) * | 2019-08-05 | 2020-07-27 | 한국과학기술연구원 | 메탄올 또는 그 전구체 합성용 촉매, 이의 제조방법 및 이를 이용한 메탄올 또는 그 전구체의 제조방법 |
KR20190095222A (ko) * | 2019-08-05 | 2019-08-14 | 한국과학기술연구원 | 메탄올 또는 그 전구체 합성용 촉매, 이의 제조방법 및 이를 이용한 메탄올 또는 그 전구체의 제조방법 |
CN113416106A (zh) * | 2021-06-21 | 2021-09-21 | 山东农业大学 | 一种液化生物基包膜控释材料的制备方法 |
CN113416106B (zh) * | 2021-06-21 | 2023-03-14 | 山东农业大学 | 一种液化生物基包膜控释材料的制备方法 |
CN114058326A (zh) * | 2021-11-22 | 2022-02-18 | 烟台德邦科技股份有限公司 | 一种粘接及可靠性优异的有机聚硅氧烷组合物及其制备方法 |
CN114160204A (zh) * | 2021-12-08 | 2022-03-11 | 江西贝特利新材料有限公司 | 一种负载型铂催化剂及其制备方法 |
CN114292289A (zh) * | 2021-12-27 | 2022-04-08 | 江西贝特利新材料有限公司 | 一种1,3-双(3-氨基丙基)-1,1,3,3-四甲基二硅氧烷及其制备方法 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
WO2016133946A1 (fr) | Micro-capsules à catalyseurs encapsulés | |
US8487020B2 (en) | Microcapsules containing curable siloxanes | |
KR101669634B1 (ko) | 온도 조절 방출을 위한 실리케이트 쉘 마이크로캡슐의 현탁액 | |
KR101683008B1 (ko) | 실리케이트 쉘 마이크로캡슐의 현탁액 | |
EP2268255B1 (fr) | Préparation de microémulsions de silicone | |
JP4280427B2 (ja) | 安定なオルガノポリシロキサンゲル、その製造法、前記ゲルおよび不相溶性の親水性液体を含有するエマルジョン、および前記エマルジョンを含有する化粧品 | |
KR101959842B1 (ko) | 이중모드 에멀젼 | |
GB2416524A (en) | Microcapsules with siloxane walls formed in situ | |
JP6178408B2 (ja) | 撥水性オルガノポリシロキサン材料 | |
EP3233049B1 (fr) | Composition de soins personnels comprenant un réseau de silicone | |
US20070244213A1 (en) | Silicone Emulsions and Their Preparation | |
EP2254932A1 (fr) | Dispersion de polymères siliconés et procédé de formation de celle-ci | |
JP5555702B2 (ja) | 分散体から形成される金属化粒子 | |
KR20140020889A (ko) | 이중모드 에멀젼 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 16752939 Country of ref document: EP Kind code of ref document: A1 |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
122 | Ep: pct application non-entry in european phase |
Ref document number: 16752939 Country of ref document: EP Kind code of ref document: A1 |