CN105085567B - Cyclosiloxane that polyfunctional group substitutes altogether, ring siloxane mixture and its preparation method and application - Google Patents
Cyclosiloxane that polyfunctional group substitutes altogether, ring siloxane mixture and its preparation method and application Download PDFInfo
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- CN105085567B CN105085567B CN201510527421.4A CN201510527421A CN105085567B CN 105085567 B CN105085567 B CN 105085567B CN 201510527421 A CN201510527421 A CN 201510527421A CN 105085567 B CN105085567 B CN 105085567B
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- dichlorosilane
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- 239000000203 mixture Substances 0.000 title claims abstract description 26
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 title claims abstract description 19
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- 238000006243 chemical reaction Methods 0.000 claims abstract description 28
- -1 methyl dialkyl silane Chemical class 0.000 claims abstract description 22
- LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 claims abstract description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000003921 oil Substances 0.000 claims description 16
- MROCJMGDEKINLD-UHFFFAOYSA-N dichlorosilane Chemical compound Cl[SiH2]Cl MROCJMGDEKINLD-UHFFFAOYSA-N 0.000 claims description 15
- 239000012044 organic layer Substances 0.000 claims description 12
- 239000010410 layer Substances 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 10
- 238000010992 reflux Methods 0.000 claims description 10
- 239000005046 Chlorosilane Substances 0.000 claims description 8
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical compound Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 claims description 8
- 238000003760 magnetic stirring Methods 0.000 claims description 8
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical class COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 claims description 8
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 7
- 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 claims description 7
- 239000006228 supernatant Substances 0.000 claims description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 6
- 239000000725 suspension Substances 0.000 claims description 6
- 230000006837 decompression Effects 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- LSRCHZDRCYIPPT-UHFFFAOYSA-N C(CCCCCCCCCCC)[Si](F)C1=CC=CC=C1 Chemical compound C(CCCCCCCCCCC)[Si](F)C1=CC=CC=C1 LSRCHZDRCYIPPT-UHFFFAOYSA-N 0.000 claims description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 4
- 239000005457 ice water Substances 0.000 claims description 4
- 230000007935 neutral effect Effects 0.000 claims description 4
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 claims description 4
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical class [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 claims description 3
- 229910021502 aluminium hydroxide Inorganic materials 0.000 claims description 3
- OHABWQNEJUUFAV-UHFFFAOYSA-N dichloro-methyl-(3,3,3-trifluoropropyl)silane Chemical class C[Si](Cl)(Cl)CCC(F)(F)F OHABWQNEJUUFAV-UHFFFAOYSA-N 0.000 claims description 3
- 238000004821 distillation Methods 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- YQGOWXYZDLJBFL-UHFFFAOYSA-N dimethoxysilane Chemical compound CO[SiH2]OC YQGOWXYZDLJBFL-UHFFFAOYSA-N 0.000 claims description 2
- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 239000011787 zinc oxide Substances 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
- QABCGOSYZHCPGN-UHFFFAOYSA-N chloro(dimethyl)silicon Chemical compound C[Si](C)Cl QABCGOSYZHCPGN-UHFFFAOYSA-N 0.000 claims 1
- QLNWYPZFNHLJGO-UHFFFAOYSA-N dichloromethyl(phenyl)silane Chemical class ClC(Cl)[SiH2]C1=CC=CC=C1 QLNWYPZFNHLJGO-UHFFFAOYSA-N 0.000 claims 1
- 150000005172 methylbenzenes Chemical class 0.000 claims 1
- 229920002545 silicone oil Polymers 0.000 abstract description 11
- 239000003960 organic solvent Substances 0.000 abstract description 4
- 125000000524 functional group Chemical group 0.000 abstract description 3
- 238000006467 substitution reaction Methods 0.000 abstract description 3
- 239000011261 inert gas Substances 0.000 abstract description 2
- 238000012545 processing Methods 0.000 abstract description 2
- 230000009257 reactivity Effects 0.000 abstract description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 14
- 229910052731 fluorine Inorganic materials 0.000 description 11
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 10
- 239000011737 fluorine Substances 0.000 description 10
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 8
- 229920001296 polysiloxane Polymers 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- ZHPNWZCWUUJAJC-UHFFFAOYSA-N fluorosilicon Chemical compound [Si]F ZHPNWZCWUUJAJC-UHFFFAOYSA-N 0.000 description 6
- 238000002156 mixing Methods 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- GNEPOXWQWFSSOU-UHFFFAOYSA-N dichloro-methyl-phenylsilane Chemical compound C[Si](Cl)(Cl)C1=CC=CC=C1 GNEPOXWQWFSSOU-UHFFFAOYSA-N 0.000 description 4
- 239000004205 dimethyl polysiloxane Substances 0.000 description 4
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 4
- 125000003709 fluoroalkyl group Chemical group 0.000 description 4
- 239000004519 grease Substances 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000000395 magnesium oxide Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 229910044991 metal oxide Inorganic materials 0.000 description 4
- 150000004706 metal oxides Chemical class 0.000 description 4
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 230000002940 repellent Effects 0.000 description 4
- 239000005871 repellent Substances 0.000 description 4
- 229910000077 silane Inorganic materials 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 125000000725 trifluoropropyl group Chemical group [H]C([H])(*)C([H])([H])C(F)(F)F 0.000 description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 3
- 238000005299 abrasion Methods 0.000 description 3
- 229940008099 dimethicone Drugs 0.000 description 3
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 3
- 238000012423 maintenance Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 231100000241 scar Toxicity 0.000 description 3
- 150000004756 silanes Chemical class 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical group [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical group [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 125000001891 dimethoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- SZVJSHCCFOBDDC-UHFFFAOYSA-N ferrosoferric oxide Chemical compound O=[Fe]O[Fe]O[Fe]=O SZVJSHCCFOBDDC-UHFFFAOYSA-N 0.000 description 2
- 239000010687 lubricating oil Substances 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- LCPVQAHEFVXVKT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)pyridin-3-amine Chemical compound NC1=CC=CN=C1OC1=CC=C(F)C=C1F LCPVQAHEFVXVKT-UHFFFAOYSA-N 0.000 description 1
- XYIWPKKMXFMQDN-UHFFFAOYSA-N 3-[dichloro(methyl)silyl]propan-1-ol Chemical compound C[Si](Cl)(Cl)CCCO XYIWPKKMXFMQDN-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 241000790917 Dioxys <bee> Species 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000005466 alkylenyl group Chemical group 0.000 description 1
- 229960005363 aluminium oxide Drugs 0.000 description 1
- 239000000908 ammonium hydroxide Substances 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
- GBAJYMPPJATTKV-UHFFFAOYSA-N butyl(trifluoro)silane Chemical compound CCCC[Si](F)(F)F GBAJYMPPJATTKV-UHFFFAOYSA-N 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000019628 coolness Nutrition 0.000 description 1
- AEJIMXVJZFYIHN-UHFFFAOYSA-N copper;dihydrate Chemical compound O.O.[Cu] AEJIMXVJZFYIHN-UHFFFAOYSA-N 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 229960004643 cupric oxide Drugs 0.000 description 1
- JJRDHFIVAPVZJN-UHFFFAOYSA-N cyclotrisiloxane Chemical compound O1[SiH2]O[SiH2]O[SiH2]1 JJRDHFIVAPVZJN-UHFFFAOYSA-N 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- BUMGIEFFCMBQDG-UHFFFAOYSA-N dichlorosilicon Chemical compound Cl[Si]Cl BUMGIEFFCMBQDG-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000011067 equilibration Methods 0.000 description 1
- 229960005191 ferric oxide Drugs 0.000 description 1
- 229940056319 ferrosoferric oxide Drugs 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 229920005560 fluorosilicone rubber Polymers 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
- NEXSMEBSBIABKL-UHFFFAOYSA-N hexamethyldisilane Chemical compound C[Si](C)(C)[Si](C)(C)C NEXSMEBSBIABKL-UHFFFAOYSA-N 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000000413 hydrolysate Substances 0.000 description 1
- 235000014413 iron hydroxide Nutrition 0.000 description 1
- NCNCGGDMXMBVIA-UHFFFAOYSA-L iron(ii) hydroxide Chemical compound [OH-].[OH-].[Fe+2] NCNCGGDMXMBVIA-UHFFFAOYSA-L 0.000 description 1
- 229910000464 lead oxide Inorganic materials 0.000 description 1
- 238000005461 lubrication Methods 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical group [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- YEXPOXQUZXUXJW-UHFFFAOYSA-N oxolead Chemical compound [Pb]=O YEXPOXQUZXUXJW-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229910021420 polycrystalline silicon Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000009991 scouring Methods 0.000 description 1
- 150000003376 silicon Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 229910001923 silver oxide Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- AAPLIUHOKVUFCC-UHFFFAOYSA-N trimethylsilanol Chemical compound C[Si](C)(C)O AAPLIUHOKVUFCC-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 description 1
- 229910021511 zinc hydroxide Inorganic materials 0.000 description 1
- 229940007718 zinc hydroxide Drugs 0.000 description 1
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- Silicon Polymers (AREA)
Abstract
A kind of substitute altogether the invention discloses polyfunctional group cyclosiloxane, ring siloxane mixture and its preparation method and application, which includes：Under the protection of inert gas, using dimethyl dichlorosilane (DMCS) or methyl dialkyl silane, reaction forms ring body mixture in the system that water and organic solvent form.The cyclosiloxane mixed methylcyclosiloxane of polyfunctional group substitution provided by the invention is not being simply mixed for simple function group substitution cyclosiloxane ring body, wherein there is the ring body containing whole functional groups.Meanwhile the of a relatively high Si H groups of reactivity are introduced in ring body, be conducive to the further modified processing for mixed methylcyclosiloxane or follow-up silicone oil product.
Description
Technical field
The present invention relates to silicone industry technical field, more particularly to a kind of trifluoro propyl, phenyl, dodecyl,
The preparation method and its usage of hydrogeneous hybrid silicone ring body.The mixed methylcyclosiloxane can be used for the special poly- silicon for synthesizing different performance
Oxygen alkane long-chain, meets corresponding industrial requirement.
Background technology
With the fast development of the industry such as machinery, electric, medicine, both at home and abroad to the demand cumulative year after year of silicone oil.Exploitation
The silicone oil production new technique that target product yield is high, cost is low, environmental-friendly is very necessary.
In the production process of dimethicone, industrially generally using the diformazan basic ring silica by low molar mass
The dimethyl polysiloxane for the low molar mass that alkane is blocked with trimethylsiloxy group is produced through equilibration reaction.Other methods are also
There are dimethyldichlorosilane and trim,ethylchlorosilane cohydrolysis, further polycondensation；The hydrolysate of dimethyldichlorosilane with
Being balanced of hexamethyldisilane is reacted and polydimethylsiloxanediols diols and trimethyl silanol or low mole by low mole
The dimethicone of quality carry out condensation reaction (dimethicone production status and progress, scientific and technological information, Zhang Chao,
2010)。
It is well known that fluorine has most strong electronegativity in all elements, often and the strong combination of other atoms
Bonding and the electronics for attracting bonding, the fluorine atom particularly in C-F, shows strong electron-withdrawing as substituent.If
To substitute part methyl containing fluoroalkyl, then it is expected to that the fluorine silicon grease under high and low temperature and high pressure is made.In fluorine silicon grease
In, it is optimal with the comprehensive performance of trifluoro propyl methyl-silicone oil, there is solvent resistance, chemical stability and the excellent lubrication of height
Performance.
The Chinese patent application of 1456564 A of Publication No. CN discloses a kind of fluorine-containing hybrid ring siloxane and its preparation
Method and purposes, the structure of the fluorine-containing hybrid ring siloxane are as follows：
Wherein, R1=C1~4Alkyl, phenyl；R2=methyl, phenyl；M=0,1 or 2；The integer of n=3~10；X=2 or 3；
The integer of Y=0~11.The compound can be used for synthesizing fluorinated polysiloxane, such as prepare fluorine silicon grease or fluorine silicone rubber.It is public
The Chinese patent that the number of opening is 1304540 C of CN prepares fluorine containing silicone oil by Material synthesis of the fluorine-containing mixed methylcyclosiloxane, but uses and be somebody's turn to do
Fluorine silicon grease heat resistance, lipophile and greasy property made from compound are simultaneously not ideal enough, there is the space of very big lifting.
The content of the invention
Cyclosiloxane, ring siloxane mixture and its preparation substituted altogether the object of the present invention is to provide a kind of polyfunctional group
Methods and applications, the lubricating oil obtained by the cyclosiloxane not only have good heat resistance, and improve lipophile and
Lubricity.
The cyclosiloxane that a kind of polyfunctional group substitutes altogether, the general expression of its component can use (I) to represent：
In formula (I), Rf=contain fluoroalkyl；RPh=contain phenyl group；RC=C8-18Alkyl；RH=H；R1=RfOr methyl；
R2=RPhOr methyl；R3=RCOr methyl；A, b, c, d, the integer of e=0~10；The integer of a+b+c+d+e=2~10.
In the present invention, by introducing C in cyclosiloxane structure8-18Alkyl and phenyl, be subsequently used for preparing lubricating oil
When, not only with good heat resistance, but also lipophile and greasy property are also substantially lifted.
In the present invention, the of a relatively high Si -- H of reactivity is introduced in cyclosiloxane, is conducive to for mixing ring
The further modified processing of body or follow-up silicone oil product.
Preferably, described contains fluoroalkyl independently selected from trifluoro propyl or 1H, 1H, 2H, 2H- perfluoro capryl；
Described is phenyl or alkyl-substituted phenyl containing phenyl group；3,5-dimethylphenyl between more preferably.
Present invention also offers a kind of ring siloxane mixture, substitutes altogether comprising the polyfunctional group described in one or more
Cyclosiloxane.
In the ring siloxane mixture of the present invention, two yuan of rings, three-membered ring and four-membered ring occupy main part, and single ring body can
Can only containing a kind of either functional group or be dimethyl ring body, but as a complete unit at least containing in above functional group
Two kinds, mixed methylcyclosiloxane be not only simple function group substitution siloxanes physical mixed but polyfunctional group be modified altogether ring body mixing
Thing.
Present invention also offers a kind of preparation method of the ring siloxane mixture, comprise the following steps：
(1) under inert gas shielding, water is with the mixed system of organic solvent composition, adding weak base or metal oxide
Or metal carbonate, maintenance system temperature is at 0~80 DEG C, and using mixed silanes as reaction raw materials, reaction 0.1~10 obtains anti-when small
Answer liquid；
The mixed silanes include functionality dimethyl dichlorosilane (DMCS) or dialkoxy silicane；
(2) reaction solution of gained in step (1) is washed to neutrality, removes lower aqueous layer and organic layer, take upper solution,
Vacuum distillation removes solvent and obtains the ring siloxane mixture.
In step (1), preferably, the water and the molar ratio of mixed chlorosilane are 1~30:1, preferably 10~
15：1.
In step (1), preferably, the organic solvent is toluene, dimethylbenzene, methyl formate, Ethyl formate, oil
Ether, dichloromethane, n-hexane, one or several kinds of mixing in hexamethylene.
In step (1), preferably, the weak base is magnesium hydroxide, aluminium hydroxide, zinc hydroxide, iron hydroxide, hydrogen
Ferrous oxide or Kocide SD；
The metal oxide is cupric oxide, iron oxide, ferroso-ferric oxide, aluminium oxide, magnesia, silver oxide, dioxy
Change the one or several kinds in manganese, brown lead oxide etc.；
The metal carbonate is sodium carbonate, sodium acid carbonate, potassium carbonate；
The weak base or the molar ratio of metal oxide or metal carbonate and silane are 2~1:1.
The weak base or metal oxide or metal carbonate, are added when reaction raw materials are dichlorosilane, and reaction is former
Expect need not then to be added during alkoxy silane.
In step (1), preferably, reaction temperature is 0~80 DEG C, more preferably 20~50 DEG C；Reaction time is
0.1~10 it is small when, more preferably 4~6 it is small when.
In step (1), preferably, the mixed silanes are dichlorosilane or dimethoxy (ethyoxyl) silane；
Wherein, the structural formula of dichlorosilane is R (CH3)SiCl2, the structural formula of dimethoxy (ethyoxyl) silane is R
(CH3)Si(OCH3), R=Rf、RPh、RCOr RH；Described in R texts as defined above.
Present invention also offers a kind of ring siloxane mixture into the application in polyfunctional group modified silicon oil, lead to
The component for changing ring siloxane mixture is crossed, can be applied to corresponding environmental requirement.
In step (2), the water scouring water is preferably saturated salt solution.After washing, it is divided into three layers, upper strata is ring body
With organic solvent, intermediate layer is water layer, and lower floor is linear body siloxanes.
Compared with prior art, the hybrid silicone ring body simple synthetic method of this method synthesis, reaction condition is gentle,
It is easily controllable, it has been successfully introduced into and has contained fluoroalkyl, phenyl, hydrogen, chain alkyl, and has can be used for the excellent feature of synthesis performance
Silicone oil and silicon rubber.
Brief description of the drawings
Fig. 1 be in embodiment 1 polyfunctional group substitute mixed methylcyclosiloxane nuclear magnetic spectrogram (1H NMR)。
Fig. 2 is that polyfunctional group substitutes mixed methylcyclosiloxane gas phase figure (GC) in embodiment 4.
Fig. 3 and Fig. 4 is the mass spectrogram (MS) that polyfunctional group substitutes mixed methylcyclosiloxane main component in embodiment 4.
Fig. 5 is that dodecylphenyl fluorosilicon oil and notification number are (contrast in 1456564 A of Publication No. CN in embodiment 1
Example 1) ring body synthesis fluorosilicon oil heat endurance contrast (TG).
Embodiment
With reference to specific embodiment, the present invention is described further, but the invention is not restricted to following embodiments.
Embodiment 1
In N2Under protection, done to a 250ml equipped with reflux condensate device, thermometer, charging hopper, magnetic stirring apparatus
50ml n-hexanes are added in dry four-hole boiling flask, 50ml water, 24.3g (0.3mol) zinc oxide, under the conditions of ice-water bath, stirs system
Into suspension, uniformly mixed mixed chlorosilane [42.2g (0.2mol) trifluoro propyls methyl two is slowly added dropwise into system
Chlorosilane, 19.1g (0.1mol) dichloromethyl phenylsilane, 2.74g (0.01mol) dodecyl methyls dimethoxysilane],
3 drip off when small, add after dichlorosilane mixture that the reaction was continued 3 it is small when, take supernatant liquor to wash 3~4 times extremely after reaction
System is neutral, casts out lower floor's aqueous layer and organic layer, takes the superiors' organic layer, filters, subtract after being dried with anhydrous sodium sulfate
Pressure steams n-hexane and obtains mixed methylcyclosiloxane 30.60g, linear body siloxanes 10.34g, yield (in terms of siloxanes quality)
74.74%.Oil repellent is 25.49 (wt) %, and phenyl content is 18.05 (wt) %.GC-MS measurement results show wherein ring body master
It is bis- trifluoro propyl -5- phenyl trimethicones cyclotrisiloxane of 1,3- and two trifluoro propyl diformazan basic ring disiloxane to want component.
In N2Under protection, to one equipped with reflux condensate device, thermometer, magnetic stirring apparatus 100ml dry three mouthfuls
The above-mentioned mixed methylcyclosiloxane 30g produced, octamethylcy-clotetrasiloxane 30g, hexamethyldisiloxane 0.32g, tetramethyl are added in flask
Base ammonium hydroxide 0.012g, when reaction 12 is small at 70 DEG C, is heated to 170 DEG C and maintains 30 minutes, decompose after reaction
Tetramethylammonium hydroxide, is -0.096Mpa in vacuum, and wherein unreacting material is removed when distillation 2 is small at 200 DEG C of system temperature
And low-boiling-point substance, you can obtain dodecylphenyl fluorosilicon oil.The silicone oil be clear liquid, molecular weight 35000g/
Mol, viscosity during 40 DEG C of the product is 220cp, and 10% thermal degradation temperature is 472.56 DEG C, with the dodecylphenyl fluorosilicon oil
Carrying out abrasion resistance test as oil body, (according to SH/T0189-1992 standard testings, obtained wear scar diameter is 0.562mm.With
Mineral oil is not stratified after dissolving each other.Abrasion resistance test is carried out to mineral oil and this silicone oil mixed liquor, obtained wear scar diameter is
0.642mm。
Embodiment 2
In N2Under protection, done to a 250ml equipped with reflux condensate device, thermometer, charging hopper, magnetic stirring apparatus
60ml toluene is added in dry four-hole boiling flask, 60ml water, 18g (0.45mol) magnesia, maintenance system temperature is at 40 DEG C, stirring body
Suspension is tied to form, uniformly mixed mixed chlorosilane [42.2g (0.2mol) trifluoro propyl methyl is slowly added dropwise into system
Dichlorosilane, 12.9g (0.1mol) dimethyldichlorosilane, 9.55g (0.05mol) dichloromethyl phenylsilane, 11.5g
(0.1mol) dimethyl dichlorosilane (DMCS)], 4 drip off when small, add after dichlorosilane mixture that the reaction was continued 2 it is small when, after reaction
Take supernatant liquor to wash 3~4 times to system neutrality, cast out lower floor's aqueous layer and organic layer, the superiors' organic layer is taken, with nothing
To be filtered after aqueous sodium persulfate drying, decompression steams toluene and obtains mixed methylcyclosiloxane 30.84g, linear body siloxanes 11.56g, yield (with
Siloxanes quality meter) 72.74%.Oil repellent is 22.17 (wt) %, and phenyl content is 6.91 (wt) %, hydrogen content in si-h bond
For 0.19 (wt) %.
Embodiment 3
In N2Under protection, done to a 500ml equipped with reflux condensate device, thermometer, charging hopper, magnetic stirring apparatus
Addition 100ml methyl formates in dry four-hole boiling flask, 100ml water, 28.08g (0.36mol) aluminium hydroxide, under the conditions of ice-water bath,
Stirring body is tied to form suspension, and uniformly mixed mixed chlorosilane (38.12g (0.18mol) trifluoro is slowly added dropwise into system
Hydroxypropyl methyl dichlorosilane, 20.70g (0.18mol) dimethyl dichlorosilane (DMCS), 16.65g (0.09mol) dichloromethyl phenylsilane,
12.735g (0.045mol) dodecyl methyls dichlorosilane), 3 drip off when small, add after dichlorosilane mixture that the reaction was continued
2 it is small when, take after reaction supernatant liquor wash 3~4 times it is neutral to system, cast out lower floor's aqueous layer and organic layer, take most
Upper organic phase layer, is filtered after being dried with anhydrous sodium sulfate, and decompression steams methyl formate and obtains mixed methylcyclosiloxane 42.53g, linear body
Siloxanes 11.37g, both are clear liquid, mixed methylcyclosiloxane yield (in terms of siloxanes quality) 78.90%.Product1H
NMR, trifluoro propyl (δ 1.78ppm, δ 3.78ppm), phenyl (δ 7.25ppm, δ 7.52ppm), dodecyl (δ 0.40ppm, δ
0.81ppm, δ 1.21ppm), si-h bond (δ 4.70ppm), Oil repellent is 12.74 (wt) %, and phenyl content is 8.25 (wt) %,
Dodecyl content is 7.65 (wt) %, and the hydrogen content in si-h bond is 0.31 (wt) %.
Embodiment 4
In N2Under protection, done to a 250ml equipped with reflux condensate device, thermometer, charging hopper, magnetic stirring apparatus
60ml toluene is added in dry four-hole boiling flask, 60ml water, 10g (0.25mol) magnesia, maintenance system temperature is at 40 DEG C, stirring body
Suspension is tied to form, uniformly mixed mixed chlorosilane [42.2g (0.2mol) trifluoro propyl methyl is slowly added dropwise into system
Dichlorosilane, 9.55g (0.05mol) dichloromethyl phenylsilane], 4 drip off when small, continue instead after adding dichlorosilane mixture
Answer 2 it is small when, take after reaction supernatant liquor wash 3~4 times it is neutral to system, cast out lower floor's aqueous layer and organic layer, take
The superiors' organic layer, is filtered after being dried with anhydrous sodium sulfate, and decompression steams toluene and obtains mixed methylcyclosiloxane 28.56g, linear body silicon
Oxygen alkane 11.56g, yield (in terms of siloxanes quality) 75.15%.Oil repellent is 28.17 (wt) %, phenyl content 15.26
(wt) %.
Comparative example 1
Fluorine-containing hybrid silicone ring is synthesized according to synthetic method disclosed in the Chinese patent of 1456564 A of Publication No. CN
Body, and fluorine containing silicone oil is prepared by mixed methylcyclosiloxane.
Three neck reaction bulbs are equipped with electromagnetic agitation, reflux condensation mode, thermometer and charging hopper, by magnesia 0.35mol and
Suspension is stirred into 150ml ethyl acetate addition reaction bulb, and the 0.15mol being pre-mixed is added dropwise under 20 DEG C of water-bath coolings
Trifluoropropylmethyldichlorosilane and 0.2mol dimethyldichlorosilane mixtures, add after dichlorosilane mixture that the reaction was continued
1h, filters off insoluble magnesium salts, and filtrate washing is washed 100ml × 2 time with distillation again behind 100ml × 2 time, dried with anhydrous sodium sulfate
After filter, ethyl acetate is evaporated off and obtains fluorine-containing hybrid silicone.
Three neck reaction bulbs are equipped with electromagnetic agitation, reflux condenser, thermometer and water-bath, take the above-mentioned mixing produced fluorine-containing
Siloxanes 16g, end-capping reagent divinyl tetramethyl disiloxane 2.4g and 95% sulfuric acid 1.92g are sequentially added in reaction bulb, are stirred
30 DEG C are warming up to after mixing 30min, reaction 40h postcoolings to room temperature, add n-hexane 20ml, be washed to neutrality.It is evaporated off afterwards molten
Agent and low cut, obtain fluorinated polysiloxane.
Fluorine containing silicone oil prepared by this comparative example is the liquid of clear, and 10% thermal degradation temperature is 385.17 DEG C, with this
Fluorosilicon oil carries out abrasion resistance test, and (according to SH/T0189-1992 standard testings, obtained wear scar diameter is 0.823mm.With ore deposit
Thing oil is layered immediately after dissolving each other, can not compounding use.
Claims (6)
- A kind of 1. preparation method of ring siloxane mixture, it is characterised in thatIn N2Under protection, to a 250ml drying four equipped with reflux condensate device, thermometer, charging hopper, magnetic stirring apparatus 50ml n-hexanes are added in mouth flask, 50ml water, 24.3g zinc oxide, under the conditions of ice-water bath, stirring body is tied to form suspension State, uniformly mixed mixed chlorosilane [42.2g trifluoropropylmethyldichlorosilanes, 19.1g methylbenzenes are slowly added dropwise into system Base dichlorosilane, 2.74g dodecyl methyls dimethoxysilane], 3 drip off when small, continue after adding dichlorosilane mixture React 3 it is small when, take after reaction supernatant liquor wash 3~4 times it is neutral to system, cast out lower floor's aqueous layer and organic layer, The superiors' organic layer is taken, is filtered after being dried with anhydrous sodium sulfate, decompression steams n-hexane and obtains mixed methylcyclosiloxane 30.60g, linearly Body siloxanes 10.34g.
- 2. a kind of ring siloxane mixture, it is characterised in that be prepared as the method described in claim 1.
- A kind of 3. preparation method of ring siloxane mixture, it is characterised in thatIn N2Under protection, to a 500ml drying four equipped with reflux condensate device, thermometer, charging hopper, magnetic stirring apparatus 100ml methyl formates are added in mouth flask, 100ml water, 28.08g aluminium hydroxides, under the conditions of ice-water bath, stirring body is tied to form outstanding Supernatant liquid state, be slowly added dropwise into system uniformly mixed mixed chlorosilane [38.12g trifluoropropylmethyldichlorosilanes, 20.70g dimethyl dichlorosilane (DMCS)s, 16.65g dichloromethyl phenylsilanes, 12.735g dodecyl methyls dichlorosilane], 3 it is small when Drip off, add after dichlorosilane mixture that the reaction was continued 2 it is small when, take supernatant liquor to wash 3~4 times into system after reaction Property, cast out lower floor's aqueous layer and organic layer, take the superiors' organic layer, filtered after being dried with anhydrous sodium sulfate, decompression steams Methyl formate obtains mixed methylcyclosiloxane 42.53g, linear body siloxanes 11.37g.
- 4. a kind of ring siloxane mixture, it is characterised in that be prepared as the method described in claim 3.
- 5. a kind of ring siloxane mixture as claimed in claim 1 is into the application in polyfunctional group modified silicon oil.
- 6. ring siloxane mixture according to claim 5 exists into the application in polyfunctional group modified silicon oil, its feature In, including：In N2Under protection, in the three-necked flask dried to a 100ml equipped with reflux condensate device, thermometer, magnetic stirring apparatus Add the mixed methylcyclosiloxane 30g, octamethylcy-clotetrasiloxane 30g, hexamethyldisiloxane 0.32g, tetramethylammonium hydroxide 0.012g, when reaction 12 is small at 70 DEG C, is heated to 170 DEG C and maintains 30 minutes, decompose tetramethyl hydrogen-oxygen after reaction Change ammonium, be -0.096Mpa in vacuum, removing wherein unreacting material and low-boiling-point substance when distillation 2 is small at 200 DEG C of system temperature, It can obtain dodecylphenyl fluorosilicon oil.
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