JPH04178428A - Non-reactive silicone resin, production thereof and polishing agent - Google Patents
Non-reactive silicone resin, production thereof and polishing agentInfo
- Publication number
- JPH04178428A JPH04178428A JP30541490A JP30541490A JPH04178428A JP H04178428 A JPH04178428 A JP H04178428A JP 30541490 A JP30541490 A JP 30541490A JP 30541490 A JP30541490 A JP 30541490A JP H04178428 A JPH04178428 A JP H04178428A
- Authority
- JP
- Japan
- Prior art keywords
- group
- mol
- formula
- silicone resin
- reactive silicone
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000005498 polishing Methods 0.000 title claims abstract description 14
- 229920002050 silicone resin Polymers 0.000 title claims description 27
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 15
- 150000001282 organosilanes Chemical class 0.000 claims abstract 3
- 125000005372 silanol group Chemical group 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 30
- 229920005989 resin Polymers 0.000 abstract description 10
- 239000011347 resin Substances 0.000 abstract description 10
- 239000007787 solid Substances 0.000 abstract description 10
- 239000007788 liquid Substances 0.000 abstract description 8
- 150000002430 hydrocarbons Chemical class 0.000 abstract description 7
- 239000005871 repellent Substances 0.000 abstract description 6
- 150000003961 organosilicon compounds Chemical class 0.000 abstract description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract description 4
- 230000002940 repellent Effects 0.000 abstract description 4
- 239000004215 Carbon black (E152) Substances 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract description 2
- 229930195733 hydrocarbon Natural products 0.000 abstract description 2
- 229910052681 coesite Inorganic materials 0.000 abstract 1
- 229910052906 cristobalite Inorganic materials 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 abstract 1
- 239000000377 silicon dioxide Substances 0.000 abstract 1
- 235000012239 silicon dioxide Nutrition 0.000 abstract 1
- 229910052682 stishovite Inorganic materials 0.000 abstract 1
- 229910052905 tridymite Inorganic materials 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 72
- -1 siloxane units Chemical group 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- 239000001993 wax Substances 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 239000004205 dimethyl polysiloxane Substances 0.000 description 8
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 8
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 8
- 229920001296 polysiloxane Polymers 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- 230000003254 anti-foaming effect Effects 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000004033 plastic Substances 0.000 description 5
- 229920003023 plastic Polymers 0.000 description 5
- 238000006884 silylation reaction Methods 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- 239000011259 mixed solution Substances 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000005054 phenyltrichlorosilane Substances 0.000 description 3
- 150000004756 silanes Chemical class 0.000 description 3
- 229920001187 thermosetting polymer Polymers 0.000 description 3
- ORVMIVQULIKXCP-UHFFFAOYSA-N trichloro(phenyl)silane Chemical compound Cl[Si](Cl)(Cl)C1=CC=CC=C1 ORVMIVQULIKXCP-UHFFFAOYSA-N 0.000 description 3
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- QIVUCLWGARAQIO-OLIXTKCUSA-N (3s)-n-[(3s,5s,6r)-6-methyl-2-oxo-1-(2,2,2-trifluoroethyl)-5-(2,3,6-trifluorophenyl)piperidin-3-yl]-2-oxospiro[1h-pyrrolo[2,3-b]pyridine-3,6'-5,7-dihydrocyclopenta[b]pyridine]-3'-carboxamide Chemical compound C1([C@H]2[C@H](N(C(=O)[C@@H](NC(=O)C=3C=C4C[C@]5(CC4=NC=3)C3=CC=CN=C3NC5=O)C2)CC(F)(F)F)C)=C(F)C=CC(F)=C1F QIVUCLWGARAQIO-OLIXTKCUSA-N 0.000 description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000003082 abrasive agent Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000000740 bleeding effect Effects 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- YGZSVWMBUCGDCV-UHFFFAOYSA-N chloro(methyl)silane Chemical compound C[SiH2]Cl YGZSVWMBUCGDCV-UHFFFAOYSA-N 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- AHUXYBVKTIBBJW-UHFFFAOYSA-N dimethoxy(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](OC)(OC)C1=CC=CC=C1 AHUXYBVKTIBBJW-UHFFFAOYSA-N 0.000 description 2
- LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 description 2
- 229920005645 diorganopolysiloxane polymer Polymers 0.000 description 2
- 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 2
- 230000000694 effects Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 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 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- HLXDKGBELJJMHR-UHFFFAOYSA-N methyl-tri(propan-2-yloxy)silane Chemical compound CC(C)O[Si](C)(OC(C)C)OC(C)C HLXDKGBELJJMHR-UHFFFAOYSA-N 0.000 description 2
- 239000006082 mold release agent Substances 0.000 description 2
- 125000001400 nonyl 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])[H] 0.000 description 2
- 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 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 235000019271 petrolatum Nutrition 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910000077 silane Inorganic materials 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 2
- 239000005051 trimethylchlorosilane Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- JLPULHDHAOZNQI-ZTIMHPMXSA-N 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC JLPULHDHAOZNQI-ZTIMHPMXSA-N 0.000 description 1
- 239000005046 Chlorosilane Substances 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 239000004166 Lanolin Substances 0.000 description 1
- 239000004264 Petrolatum Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000004163 Spermaceti wax Substances 0.000 description 1
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 1
- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000012164 animal wax Substances 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 235000013871 bee wax Nutrition 0.000 description 1
- 239000012166 beeswax Substances 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical class NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 1
- 239000000378 calcium silicate Substances 0.000 description 1
- 229910052918 calcium silicate Inorganic materials 0.000 description 1
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
- 239000004203 carnauba wax Substances 0.000 description 1
- 235000013869 carnauba wax Nutrition 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 239000012185 ceresin wax Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- QABCGOSYZHCPGN-UHFFFAOYSA-N chloro(dimethyl)silicon Chemical compound C[Si](C)Cl QABCGOSYZHCPGN-UHFFFAOYSA-N 0.000 description 1
- YCITZMJNBYYMJO-UHFFFAOYSA-N chloro(diphenyl)silicon Chemical compound C=1C=CC=CC=1[Si](Cl)C1=CC=CC=C1 YCITZMJNBYYMJO-UHFFFAOYSA-N 0.000 description 1
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical compound Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000005443 coulometric titration Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- JJQZDUKDJDQPMQ-UHFFFAOYSA-N dimethoxy(dimethyl)silane Chemical compound CO[Si](C)(C)OC JJQZDUKDJDQPMQ-UHFFFAOYSA-N 0.000 description 1
- CVQVSVBUMVSJES-UHFFFAOYSA-N dimethoxy-methyl-phenylsilane Chemical compound CO[Si](C)(OC)C1=CC=CC=C1 CVQVSVBUMVSJES-UHFFFAOYSA-N 0.000 description 1
- LRCFXGAMWKDGLA-UHFFFAOYSA-N dioxosilane;hydrate Chemical compound O.O=[Si]=O LRCFXGAMWKDGLA-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000010292 electrical insulation Methods 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- RSIHJDGMBDPTIM-UHFFFAOYSA-N ethoxy(trimethyl)silane Chemical compound CCO[Si](C)(C)C RSIHJDGMBDPTIM-UHFFFAOYSA-N 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- POPACFLNWGUDSR-UHFFFAOYSA-N methoxy(trimethyl)silane Chemical compound CO[Si](C)(C)C POPACFLNWGUDSR-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000005055 methyl trichlorosilane Substances 0.000 description 1
- GDXRFKZYPFDPSC-UHFFFAOYSA-N methyl(propan-2-yloxy)silane Chemical compound C[SiH2]OC(C)C GDXRFKZYPFDPSC-UHFFFAOYSA-N 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- JLUFWMXJHAVVNN-UHFFFAOYSA-N methyltrichlorosilane Chemical compound C[Si](Cl)(Cl)Cl JLUFWMXJHAVVNN-UHFFFAOYSA-N 0.000 description 1
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000012184 mineral wax Substances 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 239000012170 montan wax Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 235000019809 paraffin wax Nutrition 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 235000021110 pickles Nutrition 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- FDNAPBUWERUEDA-UHFFFAOYSA-N silicon tetrachloride Chemical compound Cl[Si](Cl)(Cl)Cl FDNAPBUWERUEDA-UHFFFAOYSA-N 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 229940083466 soybean lecithin Drugs 0.000 description 1
- 235000019385 spermaceti wax Nutrition 0.000 description 1
- 235000015096 spirit Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 1
- ZUEKXCXHTXJYAR-UHFFFAOYSA-N tetrapropan-2-yl silicate Chemical compound CC(C)O[Si](OC(C)C)(OC(C)C)OC(C)C ZUEKXCXHTXJYAR-UHFFFAOYSA-N 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
- JCVQKRGIASEUKR-UHFFFAOYSA-N triethoxy(phenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CC=C1 JCVQKRGIASEUKR-UHFFFAOYSA-N 0.000 description 1
- JLGNHOJUQFHYEZ-UHFFFAOYSA-N trimethoxy(3,3,3-trifluoropropyl)silane Chemical compound CO[Si](OC)(OC)CCC(F)(F)F JLGNHOJUQFHYEZ-UHFFFAOYSA-N 0.000 description 1
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 1
- PQDJYEQOELDLCP-UHFFFAOYSA-N trimethylsilane Chemical compound C[SiH](C)C PQDJYEQOELDLCP-UHFFFAOYSA-N 0.000 description 1
- AAPLIUHOKVUFCC-UHFFFAOYSA-N trimethylsilanol Chemical compound C[Si](C)(C)O AAPLIUHOKVUFCC-UHFFFAOYSA-N 0.000 description 1
- 239000012178 vegetable wax Substances 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Paints Or Removers (AREA)
- Silicon Polymers (AREA)
Abstract
Description
【発明の詳細な説明】
〔発明の技術分野〕
本発明は非反応性シリコーン樹脂に関し、詳しくは、撥
水性、消泡性、耐熱性、離型性の付与に優れた液体状か
ら固体状の非反応性シリコーン樹脂およびそれを有効成
分とする艶出し剤に関する。[Detailed Description of the Invention] [Technical Field of the Invention] The present invention relates to non-reactive silicone resins, and more specifically, non-reactive silicone resins, in particular liquid to solid silicone resins that have excellent water repellency, antifoaming properties, heat resistance, and mold release properties. This invention relates to a non-reactive silicone resin and a polishing agent containing the same as an active ingredient.
非反応性シリコーンとしてジオルガノポリシロキサンは
従来から良く知られており、撥水剤、消泡剤、耐熱剤、
離型剤、艶出し剤あるいはプラスチック成型体の改質用
の添加剤などに用いられている。またジオルガノポリシ
ロキサンは液状のものから半固体状のものまであり、用
途に応じて液状あるいは半固体(生ゴム)状の物が使い
分けられているのが現状である。しかしながら用途によ
っては、撥水性、消泡性、耐熱性、離型性、艶出し性等
が十分でないか、或いは今まで以上の性能が要求される
ようになってきている。Diorganopolysiloxane has long been well known as a non-reactive silicone, and is used as a water repellent, antifoaming agent, heat resistant agent,
It is used as a mold release agent, polishing agent, and additive for modifying plastic molded bodies. Furthermore, diorganopolysiloxanes range from liquid to semi-solid, and at present, either liquid or semi-solid (raw rubber) is used depending on the purpose. However, depending on the application, water repellency, antifoaming properties, heat resistance, mold releasability, polishing properties, etc. may not be sufficient, or more performance than ever before is required.
撥水性が要求されるカーワックスなど、撥水剤としては
、いわゆるシリコーンオイルと称するジメチルポリオル
ガノシロキサンをワックスの材料として使われているの
は良く知られている。しかしながら液状のジメチルポリ
シロキサンでは撥水性に耐久性がなく、撥水性を維持す
るためにワックス処理の頻度を多くする必要があった。It is well known that dimethylpolyorganosiloxane, also known as silicone oil, is used as a water repellent material for car waxes and other products that require water repellency. However, liquid dimethylpolysiloxane does not have durable water repellency and requires frequent wax treatment to maintain water repellency.
また耐久性を向上させる目的で半固体(生ゴム)状の高
分子ジメチルポリシロキサンを用いる場合もあるが撥水
表面が汚れやすく、更には高分子であるがため粘度が高
く取扱い難く、また乳化が難しいなどの問題もあった。In addition, semi-solid (raw rubber) polymeric dimethylpolysiloxane is sometimes used to improve durability, but the water-repellent surface is easily stained, and since it is a polymer, it has a high viscosity and is difficult to handle, and it is difficult to emulsify. There were also some problems, such as difficulty.
またジメチルポリシロキサンのプラスチック成型物の改
質にあたり、一般に改質剤としてのジメチルポリオルガ
ノシロキサンはプラスチック成型物の耐湿性を向上させ
る目的で使われている。しかしながら低分子のジメチル
ポリシロキサンではプラスチック成型物からのブリード
、高分子のジメチルポリシロキサンではプラスチック成
型物での分散不良あるいはブリードによる金型の汚染に
問題があった。In addition, when modifying plastic molded products using dimethylpolysiloxane, dimethylpolyorganosiloxane as a modifier is generally used for the purpose of improving the moisture resistance of the plastic molded product. However, low-molecular dimethylpolysiloxane has problems with bleeding from plastic molded products, and high-molecular dimethylpolysiloxane has problems with poor dispersion in plastic molded products or mold contamination due to bleeding.
また、オルガノシルセスキオキサン単位を主体にしたシ
ラノール基を含有する熱硬化性のシリコーン樹脂は、電
気絶縁用の耐熱フェスとして、耐熱・耐候性塗料用のビ
ヒクルとして、或いは撥水、離型用としてなど、広く利
用されている。この熱硬化性のシリコーン樹脂は多くは
固体状であるが、半固体状の高分子ジメチルポリシロキ
サンに比べ低分子であり、その溶液粘度は低く取扱い易
い、更に耐汚染性或いは耐久性に優れるものである。し
かし、この様な熱硬化性のシリコーン樹脂は、シラノー
ル基に起因する脱水縮合反応が徐々に進行して安定性に
大きな問題があった。In addition, thermosetting silicone resins containing silanol groups mainly composed of organosilsesquioxane units can be used as heat-resistant panels for electrical insulation, as vehicles for heat-resistant and weather-resistant paints, or as water-repellent and mold-release materials. It is widely used as. Most of this thermosetting silicone resin is solid, but it has a lower molecular weight than the semi-solid polymer dimethylpolysiloxane, has a low solution viscosity, is easy to handle, and has excellent stain resistance and durability. It is. However, such thermosetting silicone resins have a major problem in stability because the dehydration condensation reaction due to silanol groups progresses gradually.
上記オルガノシルセスキオキサン単位を含有するシリコ
ーン樹脂としては、例えば特開昭53−43171号公
報の特許請求の範囲(A)(ロ)のオルガノポリシロキ
サン、特開昭60−106890号公報の特許請求の範
囲第3項の一般式、
(R’3StOo、 s)w(R’zSiO)x(R’
SiO,、、)v(SiO,)2で示されるもの等が知
られている。Examples of silicone resins containing organosilsesquioxane units include the organopolysiloxanes described in claims (A) and (b) of JP-A-53-43171, and the patent of JP-A-60-106890. The general formula in claim 3, (R'3StOo, s)w(R'zSiO)x(R'
Those represented by SiO, , )v(SiO,)2 are known.
しかし、これらの方法によるシリコーン樹脂は、相当す
る加水分解性シラン化合物を共加水分解縮合することに
より得られるため、樹脂中にシラノール基が残存する。However, since silicone resins produced by these methods are obtained by cohydrolytic condensation of corresponding hydrolyzable silane compounds, silanol groups remain in the resins.
更に、l官能性シロキサン単位を含む場合には、共加水
分解縮合時、低分子品が生成しやすい、高分子量化しに
くい、また均一な高分子量体を得ることが困難であるい
った問題があった。Furthermore, when l-functional siloxane units are included, there are problems such as easy formation of low-molecular products, difficulty in increasing the molecular weight, and difficulty in obtaining a uniform high-molecular weight product during cohydrolytic condensation. Ta.
本発明の目的は、上記問題点を解消する、撥水性、消泡
性、耐熱性、離型性を付与する液体状から固体状の非反
応性シリコーン樹脂、更にこの非反応性シリコーン樹脂
を含んでなる艶出し剤を提供することにある。The object of the present invention is to solve the above-mentioned problems by providing a liquid to solid non-reactive silicone resin that imparts water repellency, antifoaming properties, heat resistance, and mold release properties, and furthermore, a non-reactive silicone resin containing this non-reactive silicone resin. Our objective is to provide a polishing agent consisting of:
即ち、本発明は
R31O:L単位 30〜99モル%R,SiO
単位 0〜80モル%R35iO□単位
1〜20モル%および5i02単位 0〜50モル
%(式中、Rは非置換の1価の炭化水素基および/また
はポリフルオロアルキル基を表す)
より構成され、平均分子量が500以上であり且つシラ
ノール基が0.5%以下であることを特徴とする非反応
性シリコーン樹脂、およびこれを有効成分とする艶出し
剤である。That is, the present invention provides R31O:L units 30 to 99 mol% R, SiO
Unit: 0 to 80 mol% R35iO□ unit
1 to 20 mol% and 5i02 units 0 to 50 mol% (wherein R represents an unsubstituted monovalent hydrocarbon group and/or polyfluoroalkyl group), and has an average molecular weight of 500 or more, and A non-reactive silicone resin characterized by a silanol group content of 0.5% or less, and a polishing agent containing this as an active ingredient.
本発明のシリコーン樹脂は、まず第一段階として一般式
R,5iYn−(−=0. 1. 2) ”??表され
るシラン化合物〔化合物(1)〜(3)〕を加水分解、
縮合することを行う。The silicone resin of the present invention is produced by hydrolyzing a silane compound [compounds (1) to (3)] represented by the general formula R, 5iYn-(-=0.1.2)" as a first step.
Perform condensation.
(1)一般式 5iY40〜50モル%(2)一般式
R51Ys 、 30〜100 モル%(3)一般
弐 RzSiYz 0〜80モル%(式中、Rは非置
換の1価炭化水素基および/またはポリフルオロアルキ
ル基
を表し、Yは加水分解性基を表す)
かかる(A)成分の式R,SiY、、において、Rの非
置換の1゛価炭化水素基としては、メチル基、エチル基
、プロピル基、ブチル基、ペンチル基、ヘキシル基、ヘ
プチル基、オクチル基、ノニル基、デシル基、ドデシル
基のようなアルキル基;シクロペンチル基、シクロヘキ
シル基のようなシクロアルキル基;2−フェニルエチル
基、2−フェニルプロピル基のようなアラルキル基;フ
ェニル基、トリル基のようなアリール基;などを例示す
ることができるが、合成の容易さ、あるいは入手の容易
さから炭素数1〜4のアルキル基もしくはフェニル基が
好ましい。(1) General formula 5iY40-50 mol% (2) General formula
R51Ys, 30 to 100 mol% (3) General 2 RzSiYz 0 to 80 mol% (wherein R represents an unsubstituted monovalent hydrocarbon group and/or polyfluoroalkyl group, and Y represents a hydrolyzable group ) In the formula R, SiY, of component (A), the unsubstituted monovalent hydrocarbon group of R is a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, Alkyl groups such as octyl, nonyl, decyl, and dodecyl; cycloalkyl groups such as cyclopentyl and cyclohexyl; aralkyl groups such as 2-phenylethyl and 2-phenylpropyl; phenyl, tolyl Examples thereof include aryl groups such as C1-C4 alkyl groups or phenyl groups from the viewpoint of ease of synthesis or availability.
(1)(2)および(3)の単位に相当するシランとし
ては、(1)として、テトラクロロシラン、テトラメト
キシシラン、テトラエトキシシラン、テトライソプロポ
キシシランなどが例示でき、(2)としては、メチルク
ロロシラン、フェニルトリクロロシラン、メチルトリメ
トキシシラン、メチルトリエトキシシラン、メチルトリ
イソプロコキシシラン、フェニルトリメトキシシラン、
フェニルトリエトキシシラン、3,3.3−トリフルオ
ロプロピルトリメトキシシランなどが例示でき、(3)
としては、ジメチルクロロシラン、ジフェニルクロロシ
ラン、メチルクロロシラン、ジメチルジメトキシシラン
、ジメチルジェトキシシラン、ジフェニルジメトキシシ
ラン、ジフェニルジメトキシシラン、メチルフエニルジ
メトキシシランなどが例示できる。Examples of silanes corresponding to the units of (1), (2), and (3) include tetrachlorosilane, tetramethoxysilane, tetraethoxysilane, and tetraisopropoxysilane, and (2), Methylchlorosilane, phenyltrichlorosilane, methyltrimethoxysilane, methyltriethoxysilane, methyltriisoprokoxysilane, phenyltrimethoxysilane,
Examples include phenyltriethoxysilane, 3,3,3-trifluoropropyltrimethoxysilane, etc. (3)
Examples include dimethylchlorosilane, diphenylchlorosilane, methylchlorosilane, dimethyldimethoxysilane, dimethyljethoxysilane, diphenyldimethoxysilane, diphenyldimethoxysilane, and methylphenyldimethoxysilane.
(102)および(3)より生じる部分縮合物は、各々
相当するシランを、従来公知の方法、たとえば特公昭5
B −27808号で示される方法により共加水分解縮
合して任意の分子量の縮合物を得ることができるが、こ
の縮合物に水酸基以外の加水分解性基が残存した場合で
も、本発明の範晴を越えるものではない。The partial condensates produced from (102) and (3) can be prepared using conventional methods such as Japanese Patent Publication No. 5
Although a condensate of any molecular weight can be obtained by cohydrolytic condensation using the method shown in No. B-27808, even if a hydrolyzable group other than a hydroxyl group remains in this condensate, it is still within the scope of the present invention. It does not exceed.
ここで、シランのモル比としては、(2)が30〜10
0モル%、さらに撥水剤、離型剤としての効果を考慮す
ると50〜100モル%である。また(3)が50モル
%を越えると撥水性、離型性、消泡性などが劣るため好
ましくない。Here, as the molar ratio of silane, (2) is 30 to 10
The content is 0 mol %, and 50 to 100 mol % when considering the effects as a water repellent and a mold release agent. Moreover, if (3) exceeds 50 mol%, water repellency, mold release properties, antifoaming properties, etc. will be poor, which is not preferable.
これにより得られる樹脂組成物は基本的には請求項1記
載の組成から成る公知のシリコーン樹脂であり、例えば
特公昭63−40471号のグリース等に用いられる樹
脂であるが、この方法のままでは樹脂にシラノール基が
多量に残り、前述の問題点を有する0本願の非反応性シ
リコーン樹脂は、上記部分縮合物(A)を(B)の有機
化合物で表面処理することによって、シラノール基を著
しく減少させることが特徴である。The resin composition obtained by this method is basically a known silicone resin having the composition described in claim 1, and is, for example, a resin used in the grease of Japanese Patent Publication No. 63-40471. The non-reactive silicone resin of the present invention, which has the above-mentioned problem in that a large amount of silanol groups remain in the resin, is produced by surface-treating the above partial condensate (A) with the organic compound (B) to significantly remove the silanol groups. It is characterized by decreasing
(B)有機ケイ素化合物中のRの非置換の1価炭化水素
基は前記と同様であり、メチル基、エチル基、プロピル
基、ブチル基、ペンチル基、ヘキシル基、ヘプチル基、
オクチル基、ノニル基、デシル基、ドデシル基のような
アルキル基;シクロペンチル基、シクロヘキシル基のよ
うなシクロアルキル基;2−フェニルエチル基、2−フ
ェニルプロピル基のようなアラルキル基;フェニル基、
トリル基のようなアリール基;などを例示することがで
きるが、合成の容易さ、あるいは入手の容易さから炭素
数1〜4のアルキル基もしくはフェニル基が好ましい。(B) The unsubstituted monovalent hydrocarbon group of R in the organosilicon compound is the same as above, and includes a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group,
Alkyl groups such as octyl group, nonyl group, decyl group, dodecyl group; cycloalkyl group such as cyclopentyl group, cyclohexyl group; aralkyl group such as 2-phenylethyl group, 2-phenylpropyl group; phenyl group,
Examples include aryl groups such as tolyl groups; however, alkyl groups having 1 to 4 carbon atoms or phenyl groups are preferred from the viewpoint of ease of synthesis or availability.
また、ポリフルオロアルキル基は、非置換の1価炭化水
素基の少なくとも1部の水素原子をフッ素原子に置き換
えたものである。このようなポリフルオロアルキル基と
しては、前記一般式で示される有機ケイ素化合物の合成
のし易さ、および撥水性の付与効果が優れていることか
ら、式P”Q−(式中、R”は炭素数1〜20のパーフ
ルオロアルキル基を表し、Qは炭素数2〜6の2価の非
置換のアルキレン基を表す)で示されるものであること
が望ましい。Further, a polyfluoroalkyl group is an unsubstituted monovalent hydrocarbon group in which at least a portion of the hydrogen atoms are replaced with fluorine atoms. Such a polyfluoroalkyl group has the formula P"Q- (wherein, R" represents a perfluoroalkyl group having 1 to 20 carbon atoms, and Q represents a divalent unsubstituted alkylene group having 2 to 6 carbon atoms.
斯かる(B)成分の有機ケイ素化合物としては、トリメ
チルシラン、トリエチルシラン、トリメチルクロロシラ
ン、トリメチルシラノール、トリメチルメトキシシラン
、トリメチルエトキシシラン、ヘキサメチルジシラザン
、
(CL)ssiNHcHs 、(CH3)5siNH(
CHs)t。Examples of the organosilicon compound of component (B) include trimethylsilane, triethylsilane, trimethylchlorosilane, trimethylsilanol, trimethylmethoxysilane, trimethylethoxysilane, hexamethyldisilazane, (CL)ssiNHcHs, (CH3)5siNH(
CHs)t.
(CH3) 5siN (CzHs)ア、(CHI)3
SiON(CtHs)z 5(CH3)ssiOcOc
Hz、
CH。(CH3) 5siN (CzHs)a, (CHI)3
SiON(CtHs)z 5(CH3)ssiOcOc
Hz, CH.
CF3 (CF、) z(CHz) t−Si −0C
H3CH。CF3 (CF,) z (CHz) t-Si -0C
H3CH.
C8゜
CFx (CFz) 4 (CJ) z−Si−OCH
:1CH。C8゜CFx (CFz) 4 (CJ) z-Si-OCH
:1CH.
CH3 CFs(Ch)?(CHz)z−Si−OCH3■ CH。CH3 CFs (Ch)? (CHz)z-Si-OCH3■ CH.
などを例示することができる。For example,
なお、シリル化反応後に未反応物の除去が容易であるこ
とから、上記の中でも、シラザン類もしくはクロロシラ
ン類が好ましく、単独で用いるはか併用して用いても良
い。Note that, among the above, silazane or chlorosilane are preferable because unreacted substances can be easily removed after the silylation reaction, and they may be used alone or in combination.
(A)成分の(B)成分によるシリル化反応は、混合あ
るいは混合加熱するだけで容易に進行するので操作的に
特に問題は無い、(A)成分と(B)成分の混合比は、
理論的には(B)中のRと(A)中の水酸基とが等しく
なるようにすれば良いわけであるが、(A)の部分縮合
物の架橋程度により、シリル化反応の進行が遅くなる場
合があることのほかに、シリル化後の(B)成分の除去
を容易に行うため、(A)中の水酸基に対しくB)中の
Rは1−10倍モル量が好ましい。The silylation reaction of component (A) with component (B) proceeds easily by simply mixing or mixing and heating, so there is no particular operational problem.The mixing ratio of component (A) and component (B) is:
Theoretically, it is sufficient to make R in (B) equal to the hydroxyl group in (A), but the progress of the silylation reaction may be slow depending on the degree of crosslinking of the partial condensate of (A). In addition, in order to facilitate the removal of component (B) after silylation, R in B) is preferably used in a molar amount of 1 to 10 times that of the hydroxyl group in (A).
また、この反応は無溶剤系でも良いが、シリル化反応中
に(A)成分同士の縮合反応等の副反応を抑えるため、
溶媒中で行わせてもよく、この溶剤としてはトルエン、
キシレン、ヘキサンのような炭化水素系溶剤;テトラヒ
ドロフラン、ジオキサン、などのエーテル系溶剤;ジク
ロロメタン、ジクロロエタンなどの塩素化炭化水素系溶
剤などがあげられる。この反応温度には、特に制限はな
いが、(B)の有機ケイ素化合物の種類によってその反
応性が変化するので、この温度範囲については、室温か
ら200°Cの範囲において有機ケイ素化合物の種類に
応じて定めればよい。In addition, although this reaction may be carried out in a solvent-free system, in order to suppress side reactions such as condensation reactions between the components (A) during the silylation reaction,
It may be carried out in a solvent, such as toluene,
Hydrocarbon solvents such as xylene and hexane; ether solvents such as tetrahydrofuran and dioxane; and chlorinated hydrocarbon solvents such as dichloromethane and dichloroethane. There is no particular restriction on this reaction temperature, but since the reactivity changes depending on the type of organosilicon compound (B), the temperature range is from room temperature to 200°C depending on the type of organosilicon compound. You can decide accordingly.
次に、このようにして得られた非反応性シリコーン樹脂
は、分子量が500以上でシラノール基含有量が0.5
%以下である液状から固体状の、安定性および撥水性に
優れるシリコーン樹脂であり、本発明はこの非反応性シ
リコーン樹脂を有効成分とする艶出し剤をも提供するも
のである。Next, the non-reactive silicone resin thus obtained has a molecular weight of 500 or more and a silanol group content of 0.5.
It is a liquid to solid silicone resin with excellent stability and water repellency, and the present invention also provides a polishing agent containing this non-reactive silicone resin as an active ingredient.
本願請求項3記載の艶出し剤は、上記非反応性シリコー
ン樹脂を含有することを特徴とするものであるが、配合
される他の成分としては、ワックス、溶剤、界面活性剤
、濃稠剤、研磨剤、着色剤、芳香剤、洗剤抵抗剤、その
他艶出し剤に通常配合される添加剤、から選択される従
来公知のすべてのものが対象とされる。The polishing agent according to claim 3 of the present application is characterized in that it contains the above-mentioned non-reactive silicone resin, and other components that are blended include wax, a solvent, a surfactant, and a thickening agent. , abrasives, colorants, fragrances, detergent-resistant agents, and other additives commonly incorporated into polishes.
上記したワックスとしては、例えばミツロウ、羊毛ロウ
、鯨ロウ等の動物ロウ、カルナウバロウ、綿ロウ等の植
物ロウ、モンタンロウ、セライトロウ、セレシンロウ、
パラフィンロウ、ペトロラタム等の鉱物ロウ、硬化ひま
し油、ポリエチレンロウ等の合成ロウ等が、溶剤として
はトルエン、ケロシン、ナフサ、ミネラルスピリット等
が、濃稠剤としては大豆レシチン、メチルセルロース等
が、研磨剤としてはケイ酸アルミニウム、ケイソウ土、
ベントナイト、シリカ、水和ケイ酸カルシウム、酸化マ
グネシウム、酸化鉄、酸化スズ等が、界面活性剤として
はアルキルサルフェート、アルキルスルホネート、ポリ
オキシエチレンアルキルフェニルエーテル硫酸ナトリウ
ム、ポリオキシエチレンアルキルフェニルエーテル、ポ
リオキシエチレンアルキルエーテル、ソルビタンモノエ
ステル、ベンジルアンモニウム塩等が、洗剤抵抗剤とし
ては分子中に−MHzや−(CHz)−NHz等のアミ
ノ基を有するシランあるいはシロキサン等を挙げること
ができる。Examples of the above-mentioned waxes include animal waxes such as beeswax, wool wax, spermaceti wax, vegetable waxes such as carnauba wax and cotton wax, montan wax, celite wax, ceresin wax,
Mineral waxes such as paraffin wax and petrolatum, synthetic waxes such as hydrogenated castor oil and polyethylene wax, etc. are used as solvents, toluene, kerosene, naphtha, mineral spirits, etc. are used as thickeners, soybean lecithin, methylcellulose, etc. are used as abrasive agents. is aluminum silicate, diatomaceous earth,
Bentonite, silica, hydrated calcium silicate, magnesium oxide, iron oxide, tin oxide, etc., and surfactants include alkyl sulfate, alkyl sulfonate, polyoxyethylene alkylphenyl ether sodium sulfate, polyoxyethylene alkylphenyl ether, polyoxy Ethylene alkyl ether, sorbitan monoester, benzyl ammonium salt, etc., and examples of detergent resistance agents include silanes or siloxanes having an amino group such as -MHz or -(CHz)-NHZ in the molecule.
本発明の艶出し剤は、溶剤ベース、水ベース、ペースト
状をはじめとし、あらゆる形態に適用できる。The polishing agent of the present invention can be applied in any form including solvent-based, water-based, and pasty.
更に本発明の艶出し剤には、−1γ2
(ただし、Rtは前述と同じ、−は3.4、または5)
で示される環状シロキサンやシロキサン−オキシアルキ
レン共重合体を必要に応じて配合することができる。Furthermore, the polishing agent of the present invention has -1γ2 (where Rt is the same as above, - is 3.4 or 5).
A cyclic siloxane or a siloxane-oxyalkylene copolymer represented by the above may be blended as necessary.
〔発明の効果]
本発明の非反応性シリコーン樹脂は、経時安定性、撥水
性、消泡性、耐熱性、離型性に優れた液状から固体状の
非反応性シリコーン樹脂である。この非反応性シリコー
ン樹脂は合成樹脂などに配合することによりその撥水性
を大きく向上させることができるほか、カーワックスな
どの艶出し剤に用いることで、優れた撥水性と耐久性を
有した艶出し剤を得ることができる。[Effects of the Invention] The non-reactive silicone resin of the present invention is a liquid to solid non-reactive silicone resin that has excellent stability over time, water repellency, antifoaming properties, heat resistance, and mold release properties. This non-reactive silicone resin can be added to synthetic resins to greatly improve its water repellency, and can also be used in polishing agents such as car wax to create a gloss with excellent water repellency and durability. You can get a pickle.
以下、本発明を実施例を掲げて説明する。なお、実施例
中の「部」はすべて「重量部」を表す。The present invention will be described below with reference to Examples. In addition, all "parts" in Examples represent "parts by weight."
ここで、シラノール基含有量は、シリコーン樹脂を30
0℃で2時間加熱時に発生した水分量を、三菱化成■製
、電量滴定式水分測定装置CA−06型を使用して測定
し、下記式より算出した。Here, the silanol group content is 30
The amount of moisture generated during heating at 0° C. for 2 hours was measured using a coulometric titration moisture measuring device model CA-06 manufactured by Mitsubishi Kasei ■, and calculated using the following formula.
シラノール基含有量(%)
又、熱軟化点は、環球式軟化点測定法(JISC210
4)に準じ測定した。Silanol group content (%) In addition, the thermal softening point is determined by the ring and ball softening point measurement method (JISC210
Measurement was performed according to 4).
参考例−1
メチルイソプロコキシシラン1モルとトルエン150部
との混合液をフラスコに計り取り、1%塩酸水溶液10
8部を上記混合物に20分で滴下してメチルトリイソプ
ロポキシシランを加水分解した0滴下40分後に攪拌を
止め、二層に分離した少量の塩酸を含んだ下層の水、イ
ソプロピルアルコールの混合液を減圧除去し、軟化点1
10〜120°Cのシラノール基含有量1.2%のメチ
ルポリシロキサン(s−1)を調製した。Reference Example-1 Weigh out a mixed solution of 1 mole of methylisoprokoxysilane and 150 parts of toluene into a flask, and add 10 parts of a 1% aqueous hydrochloric acid solution.
8 parts were added dropwise to the above mixture over 20 minutes to hydrolyze methyltriisopropoxysilane. After 40 minutes of addition, stirring was stopped and the mixture was separated into two layers, the lower layer containing water containing a small amount of hydrochloric acid and isopropyl alcohol. is removed under reduced pressure, and the softening point is 1.
A methylpolysiloxane (s-1) having a temperature of 10 to 120°C and a silanol group content of 1.2% was prepared.
実施例−1
参考例−1で調製したシラノール基含有メチルポリシロ
キサン100部、トルエン20011、トリメチルクロ
ロシラン1o部およびヘキサメチルジシラザン50部を
フラスコに計り取り、加熱攪拌を行った。トルエンなど
の還流下、2時間加熱攪拌を続けた後、2o閣Hgの減
圧下130 ’Cで加熱することによりトルエンなどを
除去し、軟化点80〜90℃のトリメチルシリル基含有
メチルポリシロキサン(S−1)を調製した。尚、S−
1のシラノール基含有量は0.3%であった。Example 1 100 parts of the silanol group-containing methylpolysiloxane prepared in Reference Example 1, 20011 toluene, 10 parts of trimethylchlorosilane, and 50 parts of hexamethyldisilazane were weighed into a flask and heated and stirred. After heating and stirring for 2 hours under reflux of toluene, etc., the toluene and the like were removed by heating at 130'C under a reduced pressure of 20° Hg, and trimethylsilyl group-containing methylpolysiloxane (S -1) was prepared. Furthermore, S-
The silanol group content of No. 1 was 0.3%.
参考例−2
メチルイソプロポキシシラン0.5モル、ジメチルジク
ロロシラン0.5モルとトルエン150部との混合液を
フラスコに計り取り、1%塩酸水溶液108部を上記混
合物に20分で滴下してメチルトリイソプロポキシシラ
ンを加水分解した。Reference Example-2 A mixed solution of 0.5 mol of methylisopropoxysilane, 0.5 mol of dimethyldichlorosilane, and 150 parts of toluene was weighed into a flask, and 108 parts of a 1% aqueous hydrochloric acid solution was added dropwise to the above mixture over 20 minutes. Methyltriisopropoxysilane was hydrolyzed.
滴下40分後に攪拌を止め、二層に分離した少量の塩酸
を含んだ下層の水、イソプロピルアルコールの混合液を
分液し、次に残ったトルエンの樹脂溶液の塩酸を水洗で
除去し、さらにトルエンを減圧除去し、25℃で粘度4
00cPのシラノール基含有量1.5%のメチルポリシ
ロキサン(S−2)を調製した。After 40 minutes of dropping, the stirring was stopped, and the mixture of water and isopropyl alcohol in the lower layer containing a small amount of hydrochloric acid was separated into two layers, and then the hydrochloric acid in the remaining toluene resin solution was removed by water washing, and then Toluene was removed under reduced pressure and the viscosity was 4 at 25°C.
A methylpolysiloxane (S-2) of 00 cP and a silanol group content of 1.5% was prepared.
実施例−2
トルエン200部とへキサメチルジシラザン100部を
フラスコに計り取り、加熱攪拌を行った。Example 2 200 parts of toluene and 100 parts of hexamethyldisilazane were weighed into a flask and heated and stirred.
トルエンの還流下、参考例−2で調製したシラノール基
含有メチルポリシロキサン(s−2)100部を滴下し
た。5時間還流攪拌を続けた後、20mHgの減圧下1
30 ’Cで加熱することによりトルエンなどを除去し
、25°Cで粘度50cPのトリメチルシリル基含有メ
チルポリシロキサン(S−2)を調製した。尚、S−2
のシラノール基含有量は0.1%であった。While toluene was refluxing, 100 parts of the silanol group-containing methylpolysiloxane (s-2) prepared in Reference Example-2 was added dropwise. After continuing to stir under reflux for 5 hours, under a reduced pressure of 20 mHg,
Toluene and the like were removed by heating at 30'C, and a trimethylsilyl group-containing methylpolysiloxane (S-2) having a viscosity of 50 cP was prepared at 25C. Furthermore, S-2
The silanol group content of was 0.1%.
参考例−3
フラスコに水1000部、アセトン50部を計り取り、
その混合溶液中に、メチルトリクロロシラン0.3モル
、ジメチルジクロロシラン0.3モル、フェニルトリク
ロロシラン0.4モルをトルエン200部に溶解したも
のを滴下、滴下40分後に攪拌を止め、二層に分離した
下層の塩酸水を除去し、更に上層のオルガノポリシロキ
サンのトルエン溶液に残存している水、および塩酸を過
剰のトルエンと共に減圧除去し、軟化点50〜60°C
のシラノール基含有量3.5%のオルガノポリシロキサ
ン(s−3)を調製した。Reference example-3 Weigh out 1000 parts of water and 50 parts of acetone in a flask,
A solution of 0.3 mol of methyltrichlorosilane, 0.3 mol of dimethyldichlorosilane, and 0.4 mol of phenyltrichlorosilane dissolved in 200 parts of toluene was added dropwise to the mixed solution. 40 minutes after the addition, stirring was stopped and two layers were added. The hydrochloric acid water in the lower layer separated is removed, and the water remaining in the toluene solution of organopolysiloxane in the upper layer and the hydrochloric acid are removed under reduced pressure together with excess toluene, and the softening point is 50 to 60°C.
An organopolysiloxane (s-3) having a silanol group content of 3.5% was prepared.
実施例−3
トルエン200部とへキサメチレンジシラザン100部
をフラスコに計り取り、加熱攪拌を行った。トルエンの
還流下、参考例−3で調製したシラノール基含有オルガ
ノポリシロキサン(S−3) 100部を滴下した。5
時間還流攪拌を続けた後、20mHgの減圧下130°
Cで加熱することによりトルエンなどを除去し、25°
Cで粘度cPのトリメチルシリル基含有メチルポリシロ
キサン(S−3)を調製した。尚、S−3のシラノール
基含有量は0.1%であった。Example 3 200 parts of toluene and 100 parts of hexamethylene disilazane were weighed into a flask and heated and stirred. While toluene was refluxing, 100 parts of the silanol group-containing organopolysiloxane (S-3) prepared in Reference Example-3 was added dropwise. 5
After continuing to reflux and stir for an hour, 130° under a reduced pressure of 20 mHg.
Remove toluene etc. by heating at 25°C.
A trimethylsilyl group-containing methylpolysiloxane (S-3) with a viscosity of cP was prepared. Incidentally, the silanol group content of S-3 was 0.1%.
参考例−4
フラスコに水1000部、アセトン50部を計り取り、
その混合溶液中に、フェニルトリクロロシラン1モルを
トルエン200部に溶解したものを滴下、滴下40分後
に攪拌を止め、二層に分離した下層の塩酸水を除去し、
更に上層のオルガノポリシロキサンのトルエン溶液に残
存している水、および塩酸を過剰のトルエンと共に減圧
除去し、軟化点150〜160℃のシラノール基含有量
3.0%のオルガノポリシロキサン(s−4)を調製し
た。Reference example-4 Weigh out 1000 parts of water and 50 parts of acetone in a flask,
A solution of 1 mole of phenyltrichlorosilane dissolved in 200 parts of toluene was added dropwise to the mixed solution, and 40 minutes after the addition, stirring was stopped, and the lower layer of hydrochloric acid water separated into two layers was removed.
Furthermore, water and hydrochloric acid remaining in the toluene solution of the organopolysiloxane in the upper layer were removed together with excess toluene under reduced pressure, and organopolysiloxane (S-4) with a softening point of 150 to 160°C and a silanol group content of 3.0% was prepared. ) was prepared.
実施例−4
トルエン200部とへキサメチレンジシラザン100部
をフラスコに計り取り、加熱攪拌を行った。トルエンの
還流下、参考例−4で調製したシラノール基含有オルガ
ノポリシロキサン(S−4) 100部を滴下した。5
時間還流攪拌を続けた後、20■ttgの減圧下130
℃で加熱することによりトルエンなどを除去し、軟化点
120〜130℃の非反応性シリコーン樹脂(S−4)
を調製した。尚、S−4のシラノール基含有量は0.4
%であった。Example 4 200 parts of toluene and 100 parts of hexamethylene disilazane were weighed into a flask and heated and stirred. While toluene was refluxing, 100 parts of the silanol group-containing organopolysiloxane (S-4) prepared in Reference Example-4 was added dropwise. 5
After continuing to stir under reflux for an hour, under a reduced pressure of 20 ttg,
Non-reactive silicone resin (S-4) with a softening point of 120-130°C by removing toluene etc. by heating at ℃
was prepared. In addition, the silanol group content of S-4 is 0.4
%Met.
宏1まし」1伍
本発明のシロキサン樹脂の経時安定性を観る目的で、上
記シロキサン樹脂(S−1、S−2、S−3、S−4,
5−Ls−2、s−3,5−4)の2部をクロロホルム
10部に溶解し、これをアルミシャーレに計り取り15
0℃で10時間放置した。この後、アルミシャーレを取
り出し、各々に再度クロロホルム10部を加え、溶解す
るか否かを観察した。結果を第1表に示す。Hiroshi 1 Mashi'' 1.5 For the purpose of observing the stability over time of the siloxane resin of the present invention, the siloxane resins (S-1, S-2, S-3, S-4,
Dissolve 2 parts of 5-Ls-2, s-3, 5-4) in 10 parts of chloroform, weigh this into an aluminum petri dish, and add 15
It was left at 0°C for 10 hours. After that, the aluminum Petri dishes were taken out, 10 parts of chloroform was added to each one again, and it was observed whether or not it dissolved. The results are shown in Table 1.
尚、安定性はクロロホルムに再溶解した場合を合格(O
)、クロロホルムに再溶解しない場合を不合格(×)と
した。In addition, stability is passed when redissolved in chloroform (O
), and cases where the sample was not redissolved in chloroform were judged as failed (x).
第1表
上記シロキサン樹脂(S−1、S−2、S−3、S−4
、s−1、s−2、s−3,5−4)、粘度100cS
tのポリジメチルシロキサンまたは粘度100万cS
tのポリジメチルシロキサンの10部とキシレン90部
を均一に混合して、それぞれ溶剤タイプの艶出し剤を調
製した(P−1,P−2、P−3、P−4、p−1、p
−2、P−3、P−4、p−s、p−6)。Table 1 The above siloxane resins (S-1, S-2, S-3, S-4
, s-1, s-2, s-3, 5-4), viscosity 100cS
t polydimethylsiloxane or viscosity 1 million cS
10 parts of polydimethylsiloxane of t and 90 parts of xylene were uniformly mixed to prepare solvent type polishing agents (P-1, P-2, P-3, P-4, p-1, p
-2, P-3, P-4, p-s, p-6).
これらの艶出し剤に綿布を浸漬した後、綿布を取り出し
て軽く絞り、これを用いてアルミパネルを軽く拭いた。After soaking a cotton cloth in these polishes, the cotton cloth was taken out and lightly wrung, and was used to lightly wipe the aluminum panel.
1時間放置した各アルミパネルの水の接触角および撥水
性を評価した。The water contact angle and water repellency of each aluminum panel after being left for 1 hour were evaluated.
撥水性の試験は、各アルミパネル上に、ピペットを用い
て水を1滴滴下し、これを10°/1w1nの速度で角
度をつけ、水が流れ落ちた角度で判定した。In the water repellency test, one drop of water was dropped onto each aluminum panel using a pipette, the water was angled at a speed of 10°/1w1n, and the water was judged based on the angle at which the water fell.
結果を第2表に示す。The results are shown in Table 2.
Claims (1)
SiO単位0〜80モル% R_3SiO_1_/_2単位1〜20モル%およびS
iO_2単位0〜50モル% (式中、Rは非置換の1価の炭化水素基および/または
ポリフルオロアルキル基を表す)より構成され、平均分
子量が500以上であり且つシラノール基が0.5%以
下であることを特徴とする非反応性シリコーン樹脂。 2 (A)下記(1)〜(3)で表されるオルガノシラ
ンの1種もしくは2種以上の部分縮合体を (1)一般式SiY_40〜50モル% (2)一般式RSiY_330〜100モル% (3)一般式R_2SiY_20〜80モル%(式中、
Rは非置換の1価炭化水素基および/またはポリフルオ
ロアルキル基を表し、Yは加水分解性基を表す) (B)一般式: (R_3Si)_aZ (式中、Rは非置換の1価炭化水素基および/またはポ
リフルオロアルキル基を表し、aは1または2を表し、 Zはaが1のとき水素原子、ハロゲン原子、水酸基、−
OR′、−NR′X、−ONR′_2または−OCOR
′を表し、 aが2のとき −O−、−N(X)−または−S−を表す。ただし、こ
こでR′は炭素数1〜4個のアルキル基を表し、Xは水
素原子または炭素数1〜4個のアルキル基を表す) で示される有機ケイ素化合物でシリル化することを特徴
とする請求項1記載の非反応性シリコーン樹脂の製造方
法。 3 請求項1記載の非反応性シリコーン樹脂を含んで成
ることを特徴とする艶出し剤。[Claims] 1 RSiO_3_/_2 units 30 to 99 mol% R_2
SiO units 0-80 mol% R_3SiO_1_/_2 units 1-20 mol% and S
It is composed of 0 to 50 mol% of iO_2 units (in the formula, R represents an unsubstituted monovalent hydrocarbon group and/or a polyfluoroalkyl group), has an average molecular weight of 500 or more, and has a silanol group of 0.5 % or less. 2 (A) One or more partial condensates of organosilanes represented by the following (1) to (3) (1) General formula SiY_40 to 50 mol% (2) General formula RSiY_330 to 100 mol% (3) General formula R_2SiY_20-80 mol% (in the formula,
(R represents an unsubstituted monovalent hydrocarbon group and/or a polyfluoroalkyl group, and Y represents a hydrolyzable group) (B) General formula: (R_3Si)_aZ (wherein, R represents an unsubstituted monovalent represents a hydrocarbon group and/or a polyfluoroalkyl group, a represents 1 or 2, and Z represents a hydrogen atom, a halogen atom, a hydroxyl group, -
OR', -NR'X, -ONR'_2 or -OCOR
', and when a is 2, it represents -O-, -N(X)- or -S-. However, R' represents an alkyl group having 1 to 4 carbon atoms, and X represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. The method for producing a non-reactive silicone resin according to claim 1. 3. A polishing agent comprising the non-reactive silicone resin according to claim 1.
Priority Applications (1)
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JP2305414A JP2604498B2 (en) | 1990-11-09 | 1990-11-09 | Non-reactive silicone resin and polishing agent |
Applications Claiming Priority (1)
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---|---|---|---|
JP2305414A JP2604498B2 (en) | 1990-11-09 | 1990-11-09 | Non-reactive silicone resin and polishing agent |
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JP2604498B2 JP2604498B2 (en) | 1997-04-30 |
Family
ID=17944851
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WO1997007164A1 (en) * | 1995-08-15 | 1997-02-27 | Dow Corning Asia Limited | Curable polymethylsilsesquioxane composition |
JP2002532595A (en) * | 1998-12-11 | 2002-10-02 | ワツカー−ケミー ゲゼルシヤフト ミツト ベシユレンクテル ハフツング | Organopolysiloxane resin |
JP2007008967A (en) * | 2001-02-09 | 2007-01-18 | Dow Corning Toray Co Ltd | Silicone resin composition for water-repelling coating |
JP2008280534A (en) * | 2007-04-10 | 2008-11-20 | Shin Etsu Chem Co Ltd | Resin composition for sealing optic-related device, its cured product, and sealing method of semiconductor element |
US9139737B1 (en) | 2011-11-21 | 2015-09-22 | Nanophase Technologies Corporation | Multifunctional coated powders and high solids dispersions |
US10555892B1 (en) | 2017-03-09 | 2020-02-11 | Nanophase Technologies Corporation | Functionalized siloxane or polysiloxane coated particles with enhanced light filtering properties |
US10590278B2 (en) | 2017-04-10 | 2020-03-17 | Nanophase Technologies Corporation | Coated powders having high photostability |
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JPS6054392A (en) * | 1983-09-05 | 1985-03-28 | Shin Etsu Chem Co Ltd | Silylation of organosilicon compounds |
JPS60166836A (en) * | 1984-02-09 | 1985-08-30 | Fuji Electric Corp Res & Dev Ltd | Pressure converter |
JPS633028A (en) * | 1986-06-19 | 1988-01-08 | ワツカ−−ケミ−・ゲゼルシヤフト・ミツト・ベシユレンクテル・ハフツング | Stabilization of organopolysiloxane oil having triorganosiloxy-group in terminal group unit |
JPH0259753A (en) * | 1988-08-26 | 1990-02-28 | Fujitsu Ltd | Resist composition |
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WO1997007156A1 (en) * | 1995-08-15 | 1997-02-27 | Dow Corning Asia Limited | Curable polymethylsilsesquioxane, method for curing the same and products of curing thereof |
WO1997007164A1 (en) * | 1995-08-15 | 1997-02-27 | Dow Corning Asia Limited | Curable polymethylsilsesquioxane composition |
AU706248B2 (en) * | 1995-08-15 | 1999-06-10 | Dow Corning Asia Limited | Curable polymethylsilsesquioxane, method for curing the same and products of curing thereof |
JP2002532595A (en) * | 1998-12-11 | 2002-10-02 | ワツカー−ケミー ゲゼルシヤフト ミツト ベシユレンクテル ハフツング | Organopolysiloxane resin |
JP2007008967A (en) * | 2001-02-09 | 2007-01-18 | Dow Corning Toray Co Ltd | Silicone resin composition for water-repelling coating |
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