CN116355552A - Room-temperature-curing organopolysiloxane composition and preparation method thereof - Google Patents
Room-temperature-curing organopolysiloxane composition and preparation method thereof Download PDFInfo
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- CN116355552A CN116355552A CN202310158202.8A CN202310158202A CN116355552A CN 116355552 A CN116355552 A CN 116355552A CN 202310158202 A CN202310158202 A CN 202310158202A CN 116355552 A CN116355552 A CN 116355552A
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- room temperature
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- silicone rubber
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- 239000000203 mixture Substances 0.000 title claims abstract description 46
- 229920001296 polysiloxane Polymers 0.000 title claims abstract description 10
- 238000002360 preparation method Methods 0.000 title description 10
- 239000000178 monomer Substances 0.000 claims abstract description 44
- 229920002379 silicone rubber Polymers 0.000 claims abstract description 44
- 239000004945 silicone rubber Substances 0.000 claims abstract description 41
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 26
- 238000006243 chemical reaction Methods 0.000 claims abstract description 23
- 239000003054 catalyst Substances 0.000 claims abstract description 17
- 229920005989 resin Polymers 0.000 claims abstract description 17
- 239000011347 resin Substances 0.000 claims abstract description 17
- 239000000945 filler Substances 0.000 claims abstract description 14
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 6
- IVHXEBVFCNBWED-UHFFFAOYSA-N prop-1-en-2-yloxysilane Chemical compound CC(=C)O[SiH3] IVHXEBVFCNBWED-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229920005645 diorganopolysiloxane polymer Polymers 0.000 claims abstract description 4
- 239000002318 adhesion promoter Substances 0.000 claims abstract 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 39
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 37
- -1 acryloyloxy group Chemical group 0.000 claims description 37
- 238000007789 sealing Methods 0.000 claims description 21
- 229910021485 fumed silica Inorganic materials 0.000 claims description 15
- 238000003756 stirring Methods 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 10
- 239000000377 silicon dioxide Substances 0.000 claims description 8
- 238000001816 cooling Methods 0.000 claims description 7
- 238000005406 washing Methods 0.000 claims description 7
- 238000006386 neutralization reaction Methods 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 238000009833 condensation Methods 0.000 claims description 5
- 230000005494 condensation Effects 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 5
- 230000003301 hydrolyzing effect Effects 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 125000003700 epoxy group Chemical group 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 230000003472 neutralizing effect Effects 0.000 claims description 3
- 239000003153 chemical reaction reagent Substances 0.000 claims description 2
- 125000004185 ester group Chemical group 0.000 claims description 2
- 239000004973 liquid crystal related substance Substances 0.000 claims description 2
- 238000004806 packaging method and process Methods 0.000 claims description 2
- 238000012856 packing Methods 0.000 claims description 2
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims 1
- 230000032683 aging Effects 0.000 abstract description 25
- 238000009835 boiling Methods 0.000 abstract description 14
- 238000012360 testing method Methods 0.000 description 39
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical group [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 12
- 238000004821 distillation Methods 0.000 description 10
- GBFVZTUQONJGSL-UHFFFAOYSA-N ethenyl-tris(prop-1-en-2-yloxy)silane Chemical compound CC(=C)O[Si](OC(C)=C)(OC(C)=C)C=C GBFVZTUQONJGSL-UHFFFAOYSA-N 0.000 description 10
- 229910052710 silicon Inorganic materials 0.000 description 10
- 239000010703 silicon Substances 0.000 description 10
- 230000002209 hydrophobic effect Effects 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 230000001070 adhesive effect Effects 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 8
- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical group C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 description 8
- 239000000853 adhesive Substances 0.000 description 7
- 229920002050 silicone resin Polymers 0.000 description 7
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
- 235000017557 sodium bicarbonate Nutrition 0.000 description 7
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 102000004190 Enzymes Human genes 0.000 description 6
- 108090000790 Enzymes Proteins 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000011056 performance test Methods 0.000 description 6
- 238000004321 preservation Methods 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 5
- 239000004810 polytetrafluoroethylene Substances 0.000 description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- OTARVPUIYXHRRB-UHFFFAOYSA-N diethoxy-methyl-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](C)(OCC)CCCOCC1CO1 OTARVPUIYXHRRB-UHFFFAOYSA-N 0.000 description 4
- KBJFYLLAMSZSOG-UHFFFAOYSA-N n-(3-trimethoxysilylpropyl)aniline Chemical compound CO[Si](OC)(OC)CCCNC1=CC=CC=C1 KBJFYLLAMSZSOG-UHFFFAOYSA-N 0.000 description 4
- 229910000077 silane Inorganic materials 0.000 description 4
- 238000004381 surface treatment Methods 0.000 description 4
- 238000010998 test method Methods 0.000 description 4
- 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 3
- TZZGHGKTHXIOMN-UHFFFAOYSA-N 3-trimethoxysilyl-n-(3-trimethoxysilylpropyl)propan-1-amine Chemical compound CO[Si](OC)(OC)CCCNCCC[Si](OC)(OC)OC TZZGHGKTHXIOMN-UHFFFAOYSA-N 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 3
- 239000006087 Silane Coupling Agent Substances 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 239000002981 blocking agent Substances 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000006229 carbon black Substances 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 239000007822 coupling agent Substances 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 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 3
- 238000011049 filling Methods 0.000 description 3
- DRRZZMBHJXLZRS-UHFFFAOYSA-N n-[3-[dimethoxy(methyl)silyl]propyl]cyclohexanamine Chemical compound CO[Si](C)(OC)CCCNC1CCCCC1 DRRZZMBHJXLZRS-UHFFFAOYSA-N 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229920001709 polysilazane Polymers 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 238000010025 steaming Methods 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-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
- 239000002253 acid Substances 0.000 description 2
- 230000002238 attenuated effect Effects 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 239000000084 colloidal system Substances 0.000 description 2
- 238000010411 cooking Methods 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
- 238000001035 drying Methods 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 239000008236 heating water 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
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 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
- 239000012046 mixed solvent Substances 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 125000004344 phenylpropyl group Chemical group 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 229920002631 room-temperature vulcanizate silicone Polymers 0.000 description 2
- 238000010008 shearing Methods 0.000 description 2
- 239000012756 surface treatment agent Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 2
- 125000005023 xylyl group Chemical group 0.000 description 2
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- GGZBCIDSFGUWRA-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]-n-methylpropan-1-amine Chemical compound CNCCC[Si](C)(OC)OC GGZBCIDSFGUWRA-UHFFFAOYSA-N 0.000 description 1
- LZMNXXQIQIHFGC-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]propyl 2-methylprop-2-enoate Chemical compound CO[Si](C)(OC)CCCOC(=O)C(C)=C LZMNXXQIQIHFGC-UHFFFAOYSA-N 0.000 description 1
- RWLDCNACDPTRMY-UHFFFAOYSA-N 3-triethoxysilyl-n-(3-triethoxysilylpropyl)propan-1-amine Chemical compound CCO[Si](OCC)(OCC)CCCNCCC[Si](OCC)(OCC)OCC RWLDCNACDPTRMY-UHFFFAOYSA-N 0.000 description 1
- 229910000838 Al alloy Inorganic materials 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- PHEXXGCUKSJMBJ-UHFFFAOYSA-N [O].[SiH4] Chemical compound [O].[SiH4] PHEXXGCUKSJMBJ-UHFFFAOYSA-N 0.000 description 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000011231 conductive filler Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- ZXPDYFSTVHQQOI-UHFFFAOYSA-N diethoxysilane Chemical compound CCO[SiH2]OCC ZXPDYFSTVHQQOI-UHFFFAOYSA-N 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005485 electric heating Methods 0.000 description 1
- 238000010292 electrical insulation Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000012767 functional filler Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- ZWXYOPPJTRVTST-UHFFFAOYSA-N methyl-tris(prop-1-en-2-yloxy)silane Chemical compound CC(=C)O[Si](C)(OC(C)=C)OC(C)=C ZWXYOPPJTRVTST-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- AQCUFNBUPUPBOI-UHFFFAOYSA-N n-[1-[diethoxy(methyl)silyl]oxyethyl]cyclohexanamine Chemical compound CCO[Si](C)(OCC)OC(C)NC1CCCCC1 AQCUFNBUPUPBOI-UHFFFAOYSA-N 0.000 description 1
- DTPZJXALAREFEY-UHFFFAOYSA-N n-methyl-3-triethoxysilylpropan-1-amine Chemical compound CCO[Si](OCC)(OCC)CCCNC DTPZJXALAREFEY-UHFFFAOYSA-N 0.000 description 1
- DVYVMJLSUSGYMH-UHFFFAOYSA-N n-methyl-3-trimethoxysilylpropan-1-amine Chemical compound CNCCC[Si](OC)(OC)OC DVYVMJLSUSGYMH-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- XGIZTLFJCDBRDD-UHFFFAOYSA-N phenyl-tris(prop-1-en-2-yloxy)silane Chemical compound CC(=C)O[Si](OC(C)=C)(OC(C)=C)C1=CC=CC=C1 XGIZTLFJCDBRDD-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000005464 sample preparation method Methods 0.000 description 1
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- XNDVYJMKIJRDPF-UHFFFAOYSA-N tetrakis(prop-1-en-2-yl) silicate Chemical compound CC(=C)O[Si](OC(C)=C)(OC(C)=C)OC(C)=C XNDVYJMKIJRDPF-UHFFFAOYSA-N 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 239000012974 tin catalyst Substances 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical group OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J183/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Adhesives based on derivatives of such polymers
- C09J183/04—Polysiloxanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
- C08G77/26—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen nitrogen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/04—Non-macromolecular additives inorganic
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/08—Macromolecular additives
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J183/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Adhesives based on derivatives of such polymers
- C09J183/04—Polysiloxanes
- C09J183/06—Polysiloxanes containing silicon bound to oxygen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K2201/00—Specific properties of additives
- C08K2201/014—Additives containing two or more different additives of the same subgroup in C08K
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
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Abstract
The invention discloses a room temperature curing organopolysiloxane composition, which comprises the following components: (A) A diorganopolysiloxane terminated at the end by hydroxyl or alkoxy groups; (B) an isopropenyloxy silane crosslinking agent; (C) a filler; (D) a modified adhesion promoter; (E) a catalyst and (F) an alkoxysilane resin; (D) The modified tackifier is prepared by the reaction of monomers containing-NH-groups. The silicone rubber prepared from the room-temperature-curing organopolysiloxane composition has excellent resistance to damp and heat, boiling and steam aging, and reliability, and the appearance is not deteriorated.
Description
Technical Field
The invention relates to an organic silica gel adhesive which has excellent damp-heat resistance and boiling resistance and excellent reliability.
Technical Field
Room temperature vulcanized silicone rubber is widely used in the fields of construction, electronics, and the like because of its excellent high and low temperature resistance, electrical insulation, and weather resistance. The development of the household appliance industry is rapid, the application requirements on the adhesive are higher and higher, the requirements on the high temperature resistance, the high temperature humidity resistance, the acid and alkali resistance and other performances of the adhesive are provided, but the organic silica gel adhesive produced in the current market is often obviously reduced in mechanical properties after being subjected to wet heat aging (double '85'), the adhesive properties are seriously reduced after the initial adhesion of the base material and the wet heat aging test, and the requirements on the application conditions of more severe long-time high-temperature steam cooking and high-temperature water cooking are difficult to meet, so that the problem of the room-temperature vulcanized silicone rubber in special application occasions such as household appliance steaming and baking appliances is urgently solved.
CN104031389a discloses a moisture-heat resistant room temperature vulcanized silicone rubber composition, which is prepared by reacting an amino-containing silane coupling agent and an epoxy-containing silane coupling agent under a certain condition, so that the influence of the amino-containing silane coupling agent on the moisture-heat resistance of RTV silicone rubber is improved, and meanwhile, the bonding strength of the RTV silicone rubber is not obviously reduced, but the adhesive is not boiled after being cured, and meanwhile, the used organotin catalyst is not environment-friendly; CN102424742B discloses a moisture and heat aging resistant dual-component condensation type room temperature curing silicone rubber, the component a comprises an organic compound with epoxy groups, the organic compound can react with aminosilane in the component B at room temperature to improve the moisture and heat resistance of the silicone rubber, but the adhesive is not water boiling resistant after curing, meanwhile, the dual-component condensation type room temperature curing silicone rubber and a preparation method thereof are disclosed in CN115073750a, POSS organic polysilazane is designed, the moisture and heat aging of the silicone rubber can be effectively prevented after the POSS organic polysilazane is added into the silicone rubber, the heat resistance and mechanical properties of the silicone rubber can be improved, but the POSS organic polysilazane has complex synthesis process and high cost, the adhesive is not water boiling resistant after curing, and meanwhile, the used organic tin catalyst is not environment-friendly.
Disclosure of Invention
In order to solve the problems of the prior art, the invention aims to disclose a room temperature curing organopolysiloxane composition and a preparation method thereof, wherein the composition is a de-acetone curing system, and the composition is improved to have excellent resistance to damp heat, boiling and steam aging, and reliability, and the appearance is not deteriorated.
The technical scheme provided by the invention is as follows:
a modified tackifier prepared by the reaction of monomers comprising:
R 1 Si(OR 6 ) 3 the method comprises the steps of (1),
R 1 R 2 Si(OR 7 ) 2 the method comprises the steps of (2),
R 3 Si(OR 8 ) 3 the number of the components in the liquid crystal display is 3,
R 3 R 4 Si(OR 9 ) 2 the method comprises the steps of (1) setting a first time period (4),
(OR 10 ) 3 SiR 5 Si(OR 10 ) 3 the number of the components is 5,
in the formulas 1 and 2, R 1 Is a group containing an epoxy group, an ester group or an acryloyloxy group, R in the formulas 3 and 4 3 For groups containing-NH-, R in formula 5 5 Is a divalent group containing-NH-, R in the formulas 2 and 4 2 、R 4 Represents identical or different monovalent hydrocarbon radicals, R in the formulae 1 to 5 6 、R 7 、R 8 、R 9 、R 10 Represents identical or different alkyl radicals.
The molar amounts of the monomer shown in formula 1, the monomer shown in formula 2, the monomer shown in formula 3, the monomer shown in formula 4 and the monomer shown in formula 5 are a, b, c, d, e respectively, preferably, a >0, b >0, c >0, d >0, e >0, c+d+e not equal to 0, (a+b): (c+d+e) =1: (1-3).
More preferably, 0.ltoreq.b/a <0.6.
More preferably, 0.ltoreq.d/(c+d+e) <0.25.
In the formulas 1 and 2, R 1 Is an epoxy, ester or acryloxy-containing group, preferably R 1 Is that
R 0 The alkyl group having 1 to 5 carbon atoms may be a saturated alkyl group such as methyl, ethyl, propyl, or t-butyl, and more preferably a methyl group, and m, n, and r are integers of 3 or more and zero. R in formula 1 and formula 2 1 May be the same or different.
In the formulas 3 and 4, R is 3 For groups containing-NH-, preferably, the R 3 Is of the structure of
x represents an integer greater than zero and less than or equal to 3, R 11 Represents a monovalent hydrocarbon group, and methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, or similar alkyl groups may be mentioned; cyclopentyl, cyclohexyl, or similar cycloalkyl groups; phenyl, tolyl, xylyl, or similar aryl groups; benzyl, phenethyl, phenylpropyl, or similar aralkyl groups; most preferred above are alkyl and cycloalkyl groups, especially methyl and cyclohexyl groups. R in formula 3 and formula 4 3 May be the same or different.
In formula 5, R 5 For divalent groups comprising-NH-, preferably, the R 5 Is of the structure of
s and y represent integers greater than zero and less than or equal to 3.
In the formulas 2 and 4, R 2 、R 4 Represents identical or different monovalent hydrocarbon radicals, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl or similar alkyl radicals; cyclopentyl, cyclohexyl, or similar cycloalkyl groups; phenyl, tolyl, xylyl, or similar aryl groups; benzyl, phenethyl, phenylpropyl, or similar aralkyl groups; 3, 3-trifluoropropyl, 3-chloropropyl or similar haloalkyl; most preferred above are alkyl and aryl groups, especially methyl and phenyl groups.
In the formulas 1 to 5, OR 6 、OR 7 、OR 8 、OR 9 、OR 10 Is a group which can undergo hydrolytic polycondensation, R 6 、R 7 、R 8 、R 9 、R 10 Represents the same or different alkyl groups, and specifically may be a saturated alkyl group such as methyl, ethyl, propyl, tert-butyl, etc., more preferably methyl.
Further preferably, the monomer shown in the formula 1 is one or more of gamma-glycidoxypropyl trimethoxysilane, 3-glycidoxypropyl triethoxysilane, gamma- (methacryloyloxy) propyl trimethoxysilane or beta- (3, 4-epoxycyclohexylethyl) trimethoxysilane.
Further preferably, the monomer shown in the formula 2 is one or more of 3-glycidoxypropyl methyl diethoxy silane, 3-methacryloxypropyl methyl dimethoxy silane or beta- (3, 4-epoxycyclohexylethyl) methyl dimethoxy silane.
Further preferably, the monomer represented by formula 3 is N- (N-butyl) -gamma-aminopropyl triethoxysilane, N- (N-butyl) -gamma-aminopropyl trimethoxysilane, N-phenyl-3-aminopropyl trimethoxysilane, N-methyl-3-aminopropyl triethoxysilane, cyclohexylamino methyl triethoxysilane
One or more of them.
Further preferably, the monomer represented by formula 4 is N-methylaminopropyl methyl dimethoxy silane, N-cyclohexyl-gamma-aminopropyl methyl dimethoxy silane, cyclohexylamino groupMethyl diethoxy silane
Or aniline methyl dimethoxy silane
Further preferably, the monomer shown in the formula 5 is one or more of di (3-trimethoxysilylpropyl) amine, bis [ (3- (triethoxysilylpropyl) ] ethylenediamine or di (3-triethoxysilylpropyl) amine.
Preferably, the dynamic viscosity value of the modified tackifier is 10 to 120 mPas at 25 ℃.
Preferably, the preparation method of the modified tackifier at least comprises the following steps:
A. mixing a monomer shown in a formula 1, a monomer shown in a formula 2, a monomer shown in a formula 3, a monomer shown in a formula 4, a monomer shown in a formula 5, a solvent and a hydrolytic condensation catalyst, stirring at a temperature of 40-60 ℃ and dropwise adding water for reaction, and heating to 70-80 ℃ after dropwise adding, and continuing to react for 1-3 hours;
B. cooling to room temperature, adding a neutralizing reagent for neutralization, washing with water to neutrality, and then distilling under reduced pressure to remove water and solvent;
C. cooling to room temperature, adding end capping agent and alkaline catalyst, heating to 80-100 ℃ for reaction for 1-3 hours, breaking medium, and distilling under reduced pressure to remove low molecules to obtain the modified tackifier.
Preferably, in the step a, the hydrolytic condensation catalyst is trifluoromethanesulfonic acid, hydrochloric acid, phosphoric acid, acetic acid or a strongly acidic cationic resin, and the amount thereof is not particularly limited. Preferably, in the step a, the mass of the water is 25% -40% of the total mass of the monomer shown in formula 1, the monomer shown in formula 2, the monomer shown in formula 3, the monomer shown in formula 4 and the monomer shown in formula 5.
Preferably, in the step a, the solvent is ethanol or methanol, or a mixed solvent of methanol and toluene, or a mixed solvent of ethanol and toluene, and the mass of the solvent is 1-3 times of the total mass of the monomer shown in formula 1, the monomer shown in formula 2, the monomer shown in formula 3, the monomer shown in formula 4 and the monomer shown in formula 5.
Preferably, in step B, the neutralizing agent is preferably sodium carbonate or sodium bicarbonate, and the amount thereof is not particularly limited.
Preferably, in the step B, the temperature of the reduced pressure distillation is 80-100 ℃, and the substances removed in the step also comprise reaction products such as small molecular alcohols and the like.
In the step C, the blocking agent is preferably hexamethyldisiloxane, and the mass of the blocking agent is 0.2 to 0.6% of the total mass of the monomer represented by formula 1, the monomer represented by formula 2, the monomer represented by formula 3, the monomer represented by formula 4, and the monomer represented by formula 5.
Preferably, in the step C, the basic catalyst is tetramethylammonium hydroxide, the mass of the basic catalyst is 0.003-0.006% of the total mass of the monomer shown in formula 1, the monomer shown in formula 2, the monomer shown in formula 3, the monomer shown in formula 4 and the monomer shown in formula 5, the basic catalyst can be removed by thermal decomposition, and the low-molecular-weight removal in the step C is removal of low-molecular-weight substances such as unreacted blocking agents.
A room temperature curing organopolysiloxane composition comprising the following components:
(A) Diorganopolysiloxanes terminated terminally by hydroxyl groups or alkoxy groups
(B) Isopropenyloxy silane crosslinking agent
(C) Packing material
(D) Modified tackifier
(E) A catalyst and (F) an alkoxysilane resin;
the (D) modified tackifier is the modified tackifier as described above.
Preferably, the alkoxy in the (F) alkoxy silicone resin is C1-C3 alkoxy, and the content of the alkoxy is 4-12%.
In the present invention, (F) the alkoxy group content of the alkoxy silicone resin is the mass percent of the alkoxy group, and the test method is referred to as CN105424642A.
Preferably, the (F) alkoxy silicone resin has an M/Q value of 0.7-1 and a weight average molecular weight of 2000-7000, and can be used as a commercially available silicone resin product. Preferably, the (F) alkoxysilane resin is 5 to 20 parts by weight per 100 parts by weight of component (A). The alkoxy silicone resin disclosed by the invention is favorable for improving the mechanical property of the cured silicone rubber, the alkoxy is favorable for improving the wet heat resistance and the boiling resistance of the silicone rubber, the resin is easier to crosslink with the component (A) and the crosslinking agent after being subjected to alkoxylation, when the dosage of the alkoxy silicone resin is too low, the mechanical property of the cured silicone rubber is attenuated after wet heat aging, and the appearance of the aged colloid is deteriorated, including the glossiness is reduced.
The average composition formula of the (A) terminated by hydroxyl or alkoxy is R' SiO (4-g)/2 Wherein R' is a substituted or unsubstituted monovalent hydrocarbon group, preferably a monovalent hydrocarbon group of 1 to 10 carbon atoms, which may be an alkyl group such as methyl, ethyl, propyl and butyl, an aralkyl group such as benzyl and 2-phenylethyl, and a substituted hydrocarbon group in which part or all of the hydrogen atoms in the above groups are substituted with halogen atoms or the like, such as chloromethyl and 3, 3-trifluoropropyl. Preferably, the g is 1.8-2.1. Preferably, the alkoxy group is selected from the group consisting of C1-C3 alkoxy groups.
Preferably, the dynamic viscosity number of (A) at 25℃is 500-80000mPa.s. More preferably, the dynamic viscosity number of (A) at 25℃is from 5000 to 30000mPa.s.
The (B) isopropenyloxy silane crosslinking agent is preferably one or a mixture of any of methyl triisopropenyloxy silane, vinyl triisopropenyloxy silane, phenyl triisopropenyloxy silane or tetra (isopropenyloxy) silane. Preferably, the amount of the (B) isopropenyloxy silane crosslinking agent is 4 to 8 parts by weight per 100 parts by weight of (A).
Preferably, the filler (C) comprises fumed silica or precipitated silica, the fumed silica or precipitated silica having a specific surface area of 100 to 400m 2 And/g. Preferably, the filler (C) is a filler subjected to surface treatment, and the surface treatment agent used in the surface treatment comprises one or more of hexamethyldisilazane, dimethyldichlorosilane and hydroxy silicone oil. In application, the (C) filler may also comprise other kinds of functional fillers, such as thermally conductive fillersThe specific kind of the material, flame retardant filler, conductive filler, pigment filler, etc. is not particularly limited.
Preferably, the filler (C) is a surface-treated filler, and the surface treatment method is not particularly limited, and may be performed with reference to an existing method, preferably a wet surface modification treatment, comprising the steps of: dispersing the filler in an organic solvent, adding a surface treatment agent under the condition of introducing inert gas, stirring and dispersing, isolating air at 80-100 ℃ for stirring and reacting for 12-24 hours, cooling to room temperature, separating, washing and drying to obtain the filler subjected to surface treatment.
Preferably, the filler (C) is fumed silica or precipitated silica, the amount of fumed silica or precipitated silica is 8 to 15 parts by weight per 100 parts by weight of the component (A), the fumed silica or precipitated silica has an effect on the wet heat aging resistance of the silica gel composition, the amount is too small, the appearance and glossiness of the gel are affected after the wet heat aging, and the processability of the composition is poor when the amount is too large.
Preferably, the filler (C) further comprises a fine silica powder, and the fine silica powder is used in an amount of 0 to 15 parts per 100 parts by weight of the component (A).
Preferably, the amount of the (D) modified tackifier is 1 to 5 parts by weight per 100 parts by weight of the component (A).
The catalyst (E) is preferably an organic guanidine catalyst, and can be one or more of tetramethyl guanidine propyl methyl dimethoxy silane, tetramethyl guanidine propyl methyl diethoxy silane, tetramethyl guanidine propyl dimethyl vinyl silane, tetramethyl guanidine butyl trimethoxy silane, tetramethyl guanidine butyl triethoxy silane, tetramethyl guanidine butyl methyl dimethoxy silane, tetramethyl guanidine butyl methyl diethoxy silane, 1, 3-tetramethyl guanidine propyl trimethoxy silane or 1, 3-tetramethyl guanidine propyl triethoxy silane and tetramethyl guanidine butyl dimethyl vinyl silane, preferably 1, 3-tetramethylguanidinopropyltrimethoxysilane. The mass of the catalyst (E) is 0.3-0.5% of the mass of diorganopolysiloxane with the end blocked by hydroxyl or alkoxy, so that the catalyst (E) has proper surface drying and curing time, and the ageing resistance of the silicone rubber is affected by excessive use of the catalyst (E) and the ageing resistance is attenuated.
Room temperature vulcanized silicone rubber prepared from the room temperature cured organopolysiloxane composition, and the preparation method comprises the following steps: and (3) mixing the components (A), (B), (C), (D), (E) and (F) under the vacuumizing condition, and sealing and packaging to obtain the room temperature vulcanized silicone rubber.
Compared with the prior art, the invention has the advantages that:
according to the invention, through the combination of the white carbon black, the modified tackifier and the alkoxy silicon resin, the technical problems of wet heat resistance, boiling resistance, steam aging resistance and the like of the cured room temperature vulcanized silicone rubber are solved, and the single-component acetone-free room temperature vulcanized silicone rubber with excellent wet heat resistance and boiling aging resistance is obtained.
Detailed Description
The invention is further illustrated by the following specific examples.
Example 1
200g of ethanol, 50g of gamma-glycidoxypropyl trimethoxysilane, 150g of bis (3-trimethoxysilylpropyl) amine and 0.1g of hydrochloric acid with the mass fraction of about 37% are weighed and added into a flask, the temperature is raised to 50 ℃ and water is added dropwise under stirring to react, the water is 60g, the mixture is heated to 70 ℃ after being added dropwise, the reaction is continued for 2 hours, the mixture is cooled to room temperature, 2g of sodium bicarbonate is added to neutralize and water is washed to be neutral, the temperature is raised to 100 ℃ and distilled under reduced pressure to remove water and ethanol, then 1g of hexamethyldisiloxane and 0.01g of tetramethyl ammonium hydroxide are added at room temperature and reacted for 2 hours at the temperature of 90 ℃, enzyme breaking is carried out, and low molecular substances are removed under reduced pressure and distilled to obtain the modified tackifier 1, and the dynamic viscosity value at 25 ℃ is 80 mPa.s.
100g of alpha, omega-dihydroxypolydimethylsiloxane (dynamic viscosity value at 25 ℃ is 5000 Pa.s) is added into a planetary stirrer, 8g of hydrophobic fumed silica (the manufacturer is Yingchangshui, the model is R202), 20g of alkoxy silicon resin (the manufacturer is Hubei Jiheng Sihai New Material Co., ltd., the model is SH-3021S, the weight average molecular weight is 2500, the mass percent of alkoxy is 12%) is heated to 100 ℃, vacuumizing and stirring are carried out for 1h, then cooling is carried out to normal temperature, 8g of vinyl triisopropenyloxy silane and 5g of modified tackifier 1 are added, 0.4g of 1, 3-tetramethyl guanidyl propyl trimethoxy silane are added, and the materials of all the components are uniformly mixed under the vacuumizing condition and then are filled into a sealing tube for sealing and preservation, thus obtaining the room temperature vulcanized silicone rubber.
Example 2
215g of ethanol, 70g of gamma-glycidoxypropyl trimethoxysilane, 15g of 3-glycidoxypropyl methyl diethoxysilane, 130g of bis (3-trimethoxysilylpropyl) amine and 0.1g of hydrochloric acid with the mass fraction of about 37% are weighed and added into a flask, water is dropwise added to react under stirring when the temperature is raised to 50 ℃, the water content is 64.5g, the mixture is heated to 80 ℃ after the dropwise addition, the mixture is heated to 80 ℃ for continuous reaction for 3 hours, 2g of sodium bicarbonate is added to neutralize and wash the mixture to neutrality, the mixture is heated to 100 ℃ for reduced pressure distillation to remove water and ethanol, then the mixture is cooled to 100 ℃ for reaction for 3 hours, then hexamethyldisiloxane is added to the mixture, tetramethyl ammonium hydroxide is 0.01g, enzyme breaking is carried out after the reaction at 100 ℃, and low molecular substances are removed through reduced pressure distillation, so that the modified tackifier 2 is obtained, and the dynamic viscosity value at 25 ℃ is 100 mPa.s.
100g of alpha, omega-dihydroxypolydimethylsiloxane (dynamic viscosity value at 25 ℃ is 20000 MPa.s) is added into a planetary stirrer, 10g of hydrophobic fumed silica (the manufacturer is cabot, the model is TS 530), 10g of alkoxy silicon resin (the manufacturer is SH-5201, the model is 6500, the mass percent of alkoxy is 4 percent) is heated to 100 ℃ and vacuumized and stirred for 1h, then the temperature is reduced to normal temperature, 6g of vinyl triisopropenyloxy silane and 3g of modified tackifier 2 are added, 0.4g of 1, 3-tetramethyl guanidine propyl trimethoxy silane are added, and the components are uniformly mixed under the vacuumized condition and then are filled into a sealing tube for sealing and storage, so that the room-temperature vulcanized silicone rubber is obtained.
Example 3
350g of ethanol, 80g of gamma-glycidoxypropyl trimethoxysilane, 50g of 3-glycidoxypropyl methyl diethoxysilane, 120g of N-phenyl-3-aminopropyl trimethoxysilane, 100g of bis (3-triethoxysilylpropyl) amine and 0.175g of acetic acid are weighed and added into a flask, water is dropwise added with stirring to react under the condition of heating to 50 ℃ until the water is 105g, the mixture is heated to 70 ℃ after the dropwise addition, the reaction is continued for 1 hour, the mixture is cooled to room temperature, 0.2g of sodium bicarbonate is added to neutralize and washed to be neutral, the mixture is heated to 100 ℃ until the temperature is reduced to distill water and ethanol under reduced pressure, then 1.4g of hexamethyldisiloxane is added to the mixture again, the mixture is subjected to enzyme breaking after the reaction at 80 ℃ for 1 hour, and low molecular substances are removed under reduced pressure, and the modified tackifier 3 is obtained, and the dynamic viscosity value at 25 ℃ is 10 mPa.s.
100g of alpha, omega-dihydroxypolydimethylsiloxane (dynamic viscosity value at 25 ℃ is 10000 Pa.s) is added into a planetary stirrer, 15g of hydrophobic fumed silica (the manufacturer is cabot, the model is TS 622), 5g of alkoxy silicon resin (the manufacturer is SH-3021, the model is 5000 and the mass percent of alkoxy is 6 percent) is heated to 100 ℃ and vacuumized and stirred for 1h, then cooled to normal temperature, 4g of vinyl triisopropenyloxysilane, 1g of modified tackifier 3 and 0.4g of 1, 3-tetramethyl guanidine propyl trimethoxysilane are added, and the components are uniformly mixed under vacuumized condition and then sealed and stored in a sealing tube to obtain the room temperature vulcanized silicone rubber.
Example 4
200g of ethanol, 60g of gamma- (methacryloyloxy) propyl trimethoxysilane, 110g of N-methyl-3-aminopropyl trimethoxysilane, 30g of N-cyclohexyl-gamma-aminopropyl methyl dimethoxy silane and 0.1g of hydrochloric acid with the mass fraction of about 37% are weighed and added into a flask, water is dropwise added under stirring at the temperature of 50 ℃ for reaction, the water dropwise adding amount is 60g, the mixture is heated to 70 ℃ after the dropwise adding is finished, the mixture is heated to 70 ℃ for continuous reaction for 2 hours, the mixture is cooled to room temperature, 2g of sodium bicarbonate is added for neutralization and water washing is carried out until the mixture is neutral, the mixture is heated to 100 ℃ for reduced pressure distillation to remove water and alcohol, then the mixture is cooled to room temperature, 0.7g of hexamethyldisiloxane and 0.01g of tetramethyl ammonium hydroxide are added for reaction for 1 hour at the temperature of 90 ℃, and low molecular substances are removed through reduced pressure distillation, so that the modified tackifier 4 is obtained, and the dynamic viscosity value at 25 ℃ is 30 mPa.s.
100g of alpha, omega-dihydroxypolydimethylsiloxane (dynamic viscosity value at 25 ℃ is 20000 MPa.s) is added into a planetary stirrer, 15g of hydrophobic fumed silica (the manufacturer is cabot, the model is TS 530), 5g of alkoxy silicon resin (the manufacturer is SH-3021, the model is 5000 and the mass percent of alkoxy is 6 percent) is heated to 100 ℃ and vacuumized and stirred for 1h, then cooled to normal temperature, 4g of vinyl triisopropenyloxysilane, 1g of modified tackifier 4 and 0.4g of 1, 3-tetramethyl guanidine propyl trimethoxysilane are added, and the components are uniformly mixed under vacuumized condition and then are filled into a sealing tube for sealing and preservation, so that the room-temperature vulcanized silicone rubber is obtained.
Example 5
220g of ethanol, 60g of gamma- (methacryloyloxy) propyl trimethoxysilane, 40g of 3-glycidoxypropyl methyl diethoxysilane, 60g of N-phenyl-3-aminopropyl trimethoxysilane, 10g of N-cyclohexyl-gamma-aminopropyl methyl dimethoxysilane, 50g of bis (3-trimethoxysilylpropyl) amine and 0.11g of hydrochloric acid with the mass fraction of about 37% are weighed into a flask, the temperature is raised to 50 ℃, water is added dropwise with stirring for reaction, the water is added dropwise, the reaction is continued for 2 hours after the dropwise addition, the temperature is reduced to the room temperature, 2g of sodium bicarbonate is added for neutralization and water washing is carried out, the temperature is further raised to 100 ℃, the reduced pressure distillation is carried out to remove water and alcohol, then the temperature is reduced to the room temperature, 0.7g of hexamethyldisiloxane and 0.01g of tetramethylammonium hydroxide are added for reaction for 1 hour, the enzyme breaking is carried out under the reduced pressure distillation to remove low molecular substances, and the dynamic viscosity value of the modified tackifier is 20 mPa.s at 25 ℃.
100g of alpha, omega-dihydroxypolydimethylsiloxane (dynamic viscosity value at 25 ℃ is 20000 MPa.s) is added into a planetary stirrer, 15g of hydrophobic fumed silica (the manufacturer is cabot, the model is TS 530), 5g of alkoxy silicon resin (the manufacturer is SH-3021, the model is 5000 and the mass percent of alkoxy is 6 percent) is heated to 100 ℃ and vacuumized and stirred for 1h, then cooled to normal temperature, 4g of vinyl triisopropenyloxysilane, 1g of modified tackifier 5 and 0.4g of 1, 3-tetramethyl guanidine propyl trimethoxysilane are added, and the components are uniformly mixed under vacuumized condition and then are filled into a sealing tube for sealing and preservation, so that the room-temperature vulcanized silicone rubber is obtained.
Example 6
230g of ethanol, 70g of gamma-glycidoxypropyl trimethoxysilane, 160g of N-phenyl-3-aminopropyl trimethoxysilane and 0.11g of hydrochloric acid with the mass fraction of about 37% are weighed and added into a flask, the temperature is raised to 50 ℃ and water is added dropwise under stirring to react, the water is 67g, the mixture is heated to 80 ℃ after being added dropwise, the reaction is continued for 2 hours, the mixture is cooled to the room temperature, 2g of sodium bicarbonate is added for neutralization and water washing is carried out to neutrality, the mixture is heated to 100 ℃ and distilled under reduced pressure to remove water and alcohol, the mixture is cooled to the room temperature, 0.7g of hexamethyldisiloxane and 0.011g of tetramethyl ammonium hydroxide are added, the reaction is carried out for 2 hours at 100 ℃, enzyme breaking is carried out, and low molecular substances are removed through reduced pressure distillation, so that the modified tackifier 6 is obtained, and the dynamic viscosity value at 25 ℃ is 60 mPa.s.
100g of alpha, omega-dihydroxypolydimethylsiloxane (dynamic viscosity value at 25 ℃ is 20000 MPa.s) is added into a planetary stirrer, 15g of hydrophobic fumed silica (the manufacturer is cabot, the model is TS 530), 5g of alkoxy silicon resin (the manufacturer is SH-3021, the model is 5000 and the mass percent of alkoxy is 6 percent) is heated to 100 ℃ and vacuumized and stirred for 1h, then cooled to normal temperature, 4g of vinyl triisopropenyloxysilane, 1g of modified tackifier 6 and 0.4g of 1, 3-tetramethyl guanidine propyl trimethoxysilane are added, and the components are uniformly mixed under vacuumized condition and then are filled into a sealing tube for sealing and preservation, so that the room-temperature vulcanized silicone rubber is obtained.
Comparative example 1
In a planetary stirrer, 100g of alpha, omega-dihydroxypolydimethylsiloxane (dynamic viscosity value at 25 ℃ is 5000 mPa.s), 8g of hydrophobic fumed silica (manufacturing manufacturer is Yingchangshan solid, model R202), 20g of alkoxy silicon resin (manufacturing manufacturer is Hubei Qinghai new material Co., ltd., model SH-3021S, weight average molecular weight is 2500, and weight percentage of alkoxy is 12%) are added, the temperature is raised to 100 ℃, vacuumizing and stirring are carried out for 1h, then the temperature is reduced to normal temperature, 8g of vinyl triisopropenyloxy silane, 1.25g of gamma-glycidyloxypropyl trimethoxysilane, 3.75g of di (3-trimethoxysilylpropyl) amine and 0.4g of 1, 3-tetramethyl guanidine propyl trimethoxysilane are added, and after the components are uniformly mixed under the vacuumizing condition, the mixture is filled into a sealing tube for sealing and preservation, so as to obtain the room temperature vulcanized silicone rubber.
Comparative example 2
100g of alpha, omega-dihydroxypolydimethylsiloxane (dynamic viscosity value at 25 ℃ is 20000 MPa.s) is added into a planetary stirrer, 15g of hydrophobic fumed silica (the manufacturer is cabot, model TS 530) is added, the temperature is raised to 100 ℃, the mixture is vacuumized and stirred for 1h, then the mixture is cooled to normal temperature, 4g of vinyl triisopropenyloxysilane, 1g of modified tackifier 4 and 0.4g of 1, 3-tetramethylguanylpropyl trimethoxysilane are added, and the components are uniformly mixed under the vacuuming condition and then are filled into a sealing tube for sealing and storage, so that the room-temperature vulcanized silicone rubber is obtained.
Comparative example 3
100g of alpha, omega-dihydroxypolydimethylsiloxane (dynamic viscosity value of 25 ℃ C. Is 5000 Pa.s) is added into a planetary stirrer, 20g of alkoxy silicone resin (model SH-3021S, weight average molecular weight 2500 and mass percent of alkoxy is 12%) is added into the planetary stirrer, the temperature is raised to 100 ℃ C. And is vacuumized and stirred for 1h, then the temperature is reduced to normal temperature, 8g of vinyl triisopropenyloxy silane, 5g of modified tackifier 1 and 0.4g of 1, 3-tetramethylguanylpropyl trimethoxy silane are added into the planetary stirrer, and the components are uniformly mixed under the vacuumized condition and then are filled into a sealing tube for sealing and storage, thus obtaining the room temperature vulcanized silicone rubber.
Comparative example 4
200g of ethanol, 50g of gamma-glycidoxypropyl trimethoxysilane, 150g of aminopropyl triethoxysilane and 0.1g of strong acid cationic resin are weighed and added into a flask, the temperature is raised to 50 ℃, water is added dropwise under stirring for reaction, the water is 60g, the mixture is heated to 70 ℃ after the dripping is finished, the reaction is continued for 2 hours, the mixture is cooled to room temperature, 2g of sodium bicarbonate is added for neutralization and water washing to neutrality, the mixture is heated to 100 ℃ for reduced pressure distillation to remove water and alcohol, then cooled to room temperature, 1g of hexamethyldisiloxane is added, 0.01g of tetramethyl ammonium hydroxide is reacted for 2 hours at 90 ℃, enzyme is broken, finally low molecular substances are removed through reduced pressure distillation, and the comparative modified tackifier is obtained, wherein the dynamic viscosity value at 25 ℃ is 60 mPa.s.
100g of alpha, omega-dihydroxypolydimethylsiloxane (dynamic viscosity value at 25 ℃ is 5000 Pa.s) is added into a planetary stirrer, 8g of hydrophobic fumed silica (the manufacturer is Yingchangshui, the model is R202), 20g of alkoxy silicon resin (the manufacturer is Hubei Jiheng Sihai New Material Co., ltd., the model is SH-3021S, the weight average molecular weight is 2500, the mass percent of alkoxy is 12%) is heated to 100 ℃, vacuumizing and stirring are carried out for 1h, then cooling is carried out to normal temperature, 8g of vinyl triisopropylene oxygen silane, 5g of contrast modified tackifier and 0.4g of 1, 3-tetramethyl guanidine propyl trimethoxy silane are added, and the components are uniformly mixed under the vacuumizing condition and then are filled into a sealing tube for sealing and preservation, thus obtaining the room temperature vulcanized silicone rubber.
Test examples
The room temperature vulcanized silicone rubbers of examples 1 to 6 and comparative examples 1 to 4 were subjected to performance tests, and the specific test methods are as follows:
tensile strength: according to GB/T528-2009 test
Elongation at break: according to GB/T528-2009 test
Hardness: according to GB/T531.1-2008 test
Shear strength: according to GB/T7124-2008 test
Gloss level: according to GB/T9754 test
The preparation method of the tensile strength and elongation at break test sample comprises the following steps: and uniformly filling the prepared room temperature vulcanized silicone rubber into a polytetrafluoroethylene container with a wedge-shaped groove with a depth of 2mm, a length of 25cm and a width of 20cm, then placing the container at a temperature of 23+/-2 ℃ and a relative humidity of 55% for curing for 7 days, taking out, cutting to obtain a test sample, and then performing performance test.
The preparation method of the hardness test sample comprises the following steps: and uniformly filling the prepared room temperature vulcanized silicone rubber into a polytetrafluoroethylene container with a wedge-shaped groove with a depth of 6mm, a length of 5cm and a width of 5cm, then placing the container at a temperature of 23+/-2 ℃ and a relative humidity of 55% for curing for 7 days, taking out the container, and obtaining a test sample piece, thus carrying out hardness test.
The preparation method of the shear strength test sample wafer comprises the following steps: according to GB/T7124-2008 sample preparation method: and (3) coating room temperature vulcanized silicone rubber on the surface of a 6-series aluminum alloy test sample piece, then overlapping the test sample piece, wherein the size of the test sample piece is 100 mm+/-0.25 mm, the size of the test sample piece is 25 mm+/-0.25 mm, the thickness of the test sample piece is 2 mm+/-0.1 mm, the bonding area is 12.5 mm+/-25 mm, the thickness of overlap joint glue is 0.2mm, and curing the overlapped test sample piece at the temperature (23+/-2) ℃ and the relative humidity of 55% for 7 days to perform a shear strength test.
The preparation method of the glossiness test sample piece comprises the following steps: and uniformly filling the prepared room temperature vulcanized silicone rubber into a polytetrafluoroethylene container with a wedge-shaped groove with a depth of 2mm, a length of 10cm and a width of 5cm, then placing the polytetrafluoroethylene container at a temperature of 23+/-2 ℃ and a relative humidity of 55% for curing for 7 days, taking out the polytetrafluoroethylene container, and obtaining a test sample piece, wherein the glossiness test can be carried out, and the glossiness test instrument is a YG60 DEG glossiness meter.
An aging performance test comprising the following:
the wet heat resistance testing method comprises the following steps: the test pieces (including hardness, tensile strength, elongation at break, shear strength and glossiness) after 7 days of room temperature curing are placed in a constant temperature and constant humidity test box, placed for 168 hours at 85 ℃ and 85% humidity, taken out and placed for 2 hours at normal temperature, and then appearance changes are observed, and hardness, tensile strength, elongation at break, shear strength and glossiness are tested respectively.
The water vapor resistance test method comprises the following steps: putting the steaming drawer into an electric heating pot, heating water to boil to continuously emit steam, putting a test sample piece (comprising hardness, tensile strength, elongation at break, shearing strength and glossiness test sample pieces) solidified at room temperature for 7 days on the steaming drawer, starting timing, putting the test sample piece under the water steam condition for 24 hours, taking out, putting at normal temperature for 2 hours, observing appearance change, and respectively testing the hardness, the tensile strength, the elongation at break, the shearing strength and the glossiness.
The boiling resistance test method comprises the following steps: heating water to boiling, immersing a test sample sheet (comprising hardness, tensile strength, elongation at break, shear strength and glossiness) cured at room temperature for 7 days into the boiling water, starting timing, taking out the test sample sheet after being boiled for 24 hours, standing at the room temperature for 2 hours, observing appearance change, and respectively testing the hardness, the tensile strength, the elongation at break, the shear strength and the glossiness.
Table 1 shows the performance test data of room temperature vulcanized silicone rubber before aging.
Table 1 table of performance test data
Table 2 shows the performance test data of the room temperature vulcanized silicone rubber after being subjected to wet heat aging.
TABLE 2 data sheet for testing humidity and heat aging resistance
Table 3 shows the data of the steam aging resistance test performed on room temperature vulcanized silicone rubber.
Table 3 data sheet for steam aging resistance test
Table 4 shows the data of the test of the resistance to aging by boiling for room temperature vulcanized silicone rubber.
Table 4 table for test of aging performance against boiling
As can be seen from the data in tables 1, 2, 3 and 4, in comparative example 1, a conventional coupling agent is used as a tackifier, in comparative example 3, white carbon black is not added, in comparative example 4, an epoxy coupling agent is used to react with a primary amino coupling agent to prepare a tackifier, and compared with example 1, the mechanical properties of the silicone rubber of comparative example 1 are remarkably reduced after aging, while the mechanical properties of the silicone rubbers of comparative example 3 and comparative example 4 are remarkably reduced after aging, and meanwhile, the appearance change and the glossiness of the colloid per se are also reduced; compared with the silicon rubber of the embodiment 4, the mechanical property of the silicon rubber of the embodiment 2 is obviously reduced after aging, and the appearance is deteriorated and the glossiness is reduced, namely, the invention effectively improves the damp and heat resistance, boiling resistance and steam aging resistance of the silicon rubber by combining the white carbon black, the modified tackifier and the alkoxy silicon resin.
The foregoing is a further detailed description of the invention in connection with the preferred embodiments, and it is not intended that the invention be limited to the specific embodiments described. It will be apparent to those skilled in the art that several simple deductions or substitutions may be made without departing from the spirit of the invention, and these should be considered to be within the scope of the invention.
Claims (10)
1. A modified adhesion promoter prepared by the reaction of monomers comprising:
R 1 Si(OR 6 ) 3 the method comprises the steps of (1),
R 1 R 2 Si(OR 7 ) 2 the method comprises the steps of (2),
R 3 Si(OR 8 ) 3 the number of the components in the liquid crystal display is 3,
R 3 R 4 Si(OR 9 ) 2 the method comprises the steps of (1) setting a first time period (4),
(OR 10 ) 3 SiR 5 Si(OR 10 ) 3 the number of the components is 5,
in the formulas 1 and 2, R 1 Is a group containing an epoxy group, an ester group or an acryloyloxy group, R in the formulas 3 and 4 3 For groups containing-NH-, R in formula 5 5 Is a divalent group containing-NH-, R in the formulas 2 and 4 2 、R 4 Represents identical or different monovalent hydrocarbon radicals, R in the formulae 1 to 5 6 、R 7 、R 8 、R 9 、R 10 Represents identical or different alkyl radicals.
2. The modified adhesion promoter of claim 1 wherein the monomers of formula 1, formula 2, formula 3, formula 4, and formula 5 are used in amounts of a, b, c, d, e, a >0, b >0, c >0, d >0, e >0, c+d+e noteq 0, respectively: (c+d+e) =1: (1-3).
3. The modified adhesion promoter of claim 2, wherein 0.ltoreq.d/(c+d+e) <0.25.
4. The modified adhesion promoter of claim 1 wherein R in formulas 1 and 2 1 Is that
R 0 And represents C1-C5 alkyl, m, n and r are integers of greater than zero and less than or equal to 3.
5. The modified adhesion promoter of claim 1 wherein in formulas 3 and 4, said R 3 Is of the structure of
x represents an integer greater than zero and less than or equal to 3, R 11 Represents a monovalent hydrocarbon group.
6. The modified adhesion promoter of claim 1 wherein in formula 5, said R 5 Is of the structure of
s and y represent integers greater than zero and less than or equal to 3.
7. The method for producing a modified tackifier according to any one of claims 1 to 6, comprising at least the steps of:
A. mixing a monomer shown in a formula 1, a monomer shown in a formula 2, a monomer shown in a formula 3, a monomer shown in a formula 4, a monomer shown in a formula 5, a solvent and a hydrolytic condensation catalyst, stirring at a temperature of 40-60 ℃ and dropwise adding water for reaction, and heating to 70-80 ℃ after dropwise adding, and continuing to react for 1-3 hours;
B. cooling to room temperature, adding a neutralizing reagent for neutralization, washing with water to neutrality, and then distilling under reduced pressure to remove water and solvent;
C. cooling to room temperature, adding end capping agent and alkaline catalyst, heating to 80-100 ℃ for reaction for 1-3 hours, breaking medium, and distilling under reduced pressure to remove low molecules to obtain the modified tackifier.
8. A room temperature curing organopolysiloxane composition characterized by comprising the following components:
(A) Diorganopolysiloxanes terminated terminally by hydroxyl groups or alkoxy groups
(B) Isopropenyloxy silane crosslinking agent
(C) Packing material
(D) Modified tackifier
(E) A catalyst and (F) an alkoxysilane resin;
the (D) modified tackifier is a modified tackifier according to any one of claims 1 to 6.
9. The room temperature curing organopolysiloxane composition according to claim 8, wherein the (C) filler comprises fumed silica or precipitated silica in an amount of 8 to 15 parts by weight per 100 parts by weight of component (a).
10. Room temperature vulcanized silicone rubber prepared from the room temperature curable organopolysiloxane composition according to claim 8 or 9, prepared by the method of: and (3) mixing the components (A), (B), (C), (D), (E) and (F) under the vacuumizing condition, and sealing and packaging to obtain the room temperature vulcanized silicone rubber.
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| CN116987278A (en) * | 2023-08-04 | 2023-11-03 | 浙江永通新材料股份有限公司 | Low-temperature self-healing polysiloxane supermolecular elastomer and preparation method thereof |
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| JP2010084101A (en) * | 2008-10-02 | 2010-04-15 | Shin-Etsu Chemical Co Ltd | Room-temperature-curing organopolysiloxane composition and control equipment for automobile sealed with the composition |
| CN103755963A (en) * | 2013-12-27 | 2014-04-30 | 深圳市安品有机硅材料有限公司 | Polysiloxane thickening agent and preparation method thereof |
| WO2015158257A1 (en) * | 2014-04-18 | 2015-10-22 | 苏州天山新材料技术有限公司 | High-adhesive one-component deoximation type room-temperature vulcanized silicone rubber sealant and preparation method therefor |
| CN114231245A (en) * | 2021-12-28 | 2022-03-25 | 深圳市安品有机硅材料有限公司 | Room temperature curing organopolysiloxane composition |
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| JP2010084101A (en) * | 2008-10-02 | 2010-04-15 | Shin-Etsu Chemical Co Ltd | Room-temperature-curing organopolysiloxane composition and control equipment for automobile sealed with the composition |
| CN103755963A (en) * | 2013-12-27 | 2014-04-30 | 深圳市安品有机硅材料有限公司 | Polysiloxane thickening agent and preparation method thereof |
| WO2015158257A1 (en) * | 2014-04-18 | 2015-10-22 | 苏州天山新材料技术有限公司 | High-adhesive one-component deoximation type room-temperature vulcanized silicone rubber sealant and preparation method therefor |
| CN114231245A (en) * | 2021-12-28 | 2022-03-25 | 深圳市安品有机硅材料有限公司 | Room temperature curing organopolysiloxane composition |
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