CN107793500A - 硅烷改性的共聚物、制备方法和粘合性改进剂 - Google Patents
硅烷改性的共聚物、制备方法和粘合性改进剂 Download PDFInfo
- Publication number
- CN107793500A CN107793500A CN201710799302.3A CN201710799302A CN107793500A CN 107793500 A CN107793500 A CN 107793500A CN 201710799302 A CN201710799302 A CN 201710799302A CN 107793500 A CN107793500 A CN 107793500A
- Authority
- CN
- China
- Prior art keywords
- silane
- modified copolymer
- component units
- formula
- copolymer
- 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.)
- Pending
Links
- 229920001577 copolymer Polymers 0.000 title claims abstract description 54
- 239000003607 modifier Substances 0.000 title claims abstract description 9
- 238000002360 preparation method Methods 0.000 title abstract description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 41
- 229910052697 platinum Inorganic materials 0.000 claims description 20
- 150000003961 organosilicon compounds Chemical class 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 15
- 239000003054 catalyst Substances 0.000 claims description 8
- 238000006459 hydrosilylation reaction Methods 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 4
- 150000008064 anhydrides Chemical group 0.000 abstract description 12
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 abstract description 9
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 abstract description 7
- 239000000376 reactant Substances 0.000 abstract description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 239000000203 mixture Substances 0.000 description 19
- -1 amino, acryloyl group Chemical group 0.000 description 11
- 229920002857 polybutadiene Polymers 0.000 description 11
- 239000005062 Polybutadiene Substances 0.000 description 10
- 239000003822 epoxy resin Substances 0.000 description 7
- 229920000647 polyepoxide Polymers 0.000 description 7
- 239000000126 substance Substances 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 4
- 238000005227 gel permeation chromatography Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 229910000077 silane Inorganic materials 0.000 description 4
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 150000008065 acid anhydrides Chemical class 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 125000003963 dichloro group Chemical group Cl* 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical class C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229920001721 polyimide Polymers 0.000 description 2
- 239000009719 polyimide resin Substances 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 2
- YLXAHVVGOSHZPA-UHFFFAOYSA-N 1,2-dichlorocycloocta-1,3-diene Chemical compound ClC1=C(Cl)C=CCCCC1 YLXAHVVGOSHZPA-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 1
- WUMMIJWEUDHZCL-UHFFFAOYSA-N 3-prop-2-enyloxolane-2,5-dione Chemical compound C=CCC1CC(=O)OC1=O WUMMIJWEUDHZCL-UHFFFAOYSA-N 0.000 description 1
- JIUWLLYCZJHZCZ-UHFFFAOYSA-N 3-propyloxolane-2,5-dione Chemical compound CCCC1CC(=O)OC1=O JIUWLLYCZJHZCZ-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- FUDZWZRQTOJFRW-UHFFFAOYSA-N C1(CCC(=O)O1)=O.C(C)O[Si](CCCSSSSCCC[Si](OCC)(OCC)OCC)(OCC)OCC Chemical class C1(CCC(=O)O1)=O.C(C)O[Si](CCCSSSSCCC[Si](OCC)(OCC)OCC)(OCC)OCC FUDZWZRQTOJFRW-UHFFFAOYSA-N 0.000 description 1
- 125000000041 C6-C10 aryl group Chemical group 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- 229910003978 SiClx Inorganic materials 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000010426 asphalt Substances 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 150000008359 benzonitriles Chemical class 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 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 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- NBBQQQJUOYRZCA-UHFFFAOYSA-N diethoxymethylsilane Chemical compound CCOC([SiH3])OCC NBBQQQJUOYRZCA-UHFFFAOYSA-N 0.000 description 1
- 125000001891 dimethoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- RCNRJBWHLARWRP-UHFFFAOYSA-N ethenyl-[ethenyl(dimethyl)silyl]oxy-dimethylsilane;platinum Chemical compound [Pt].C=C[Si](C)(C)O[Si](C)(C)C=C RCNRJBWHLARWRP-UHFFFAOYSA-N 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 125000003136 n-heptyl 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])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- UHUUYVZLXJHWDV-UHFFFAOYSA-N trimethyl(methylsilyloxy)silane Chemical compound C[SiH2]O[Si](C)(C)C UHUUYVZLXJHWDV-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/42—Introducing metal atoms or metal-containing groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C08C19/00—Chemical modification of rubber
- C08C19/25—Incorporating silicon atoms into the molecule
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C08C19/00—Chemical modification of rubber
- C08C19/28—Reaction with compounds containing carbon-to-carbon unsaturated bonds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C08C19/00—Chemical modification of rubber
- C08C19/30—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule
- C08C19/34—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule reacting with oxygen or oxygen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/04—Anhydrides, e.g. cyclic anhydrides
- C08F222/06—Maleic anhydride
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F230/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
- C08F230/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal
- C08F230/08—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon
- C08F230/085—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon the monomer being a polymerisable silane, e.g. (meth)acryloyloxy trialkoxy silanes or vinyl trialkoxysilanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F236/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F236/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F236/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
- C08F236/06—Butadiene
-
- 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
- C09J109/00—Adhesives based on homopolymers or copolymers of conjugated diene hydrocarbons
-
- 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
-
- 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
- C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
Abstract
本发明为硅烷改性的共聚物、制备方法和粘合性改进剂。包含丁二烯构成单元、具有水解性甲硅烷基的构成单元和具有酸酐官能度的构成单元的硅烷改性的共聚物因为其分子量而是低挥发性的。其可以从相对廉价的反应物合成。
Description
相关申请的交叉引用
本非临时申请在美国法典第35卷第119节(a)款下要求2016年9月7日于日本提交的第2016-174727号专利申请的优先权，所述专利申请的全部内容通过引用并入本文。
技术领域
本发明涉及硅烷改性的共聚物、用于制备所述共聚物的方法和粘合性改进剂。更具体地，其涉及具有酸酐官能团和水解性甲硅烷基的聚丁二烯骨架的共聚物，用于制备所述共聚物的方法，和包括所述共聚物的粘合性改进剂。
背景技术
具有与有机物质呈反应性的官能团(以环氧基、氨基、丙烯酰基、甲基丙烯酰基、巯基或异氰酸酯基团或酸酐残基为典型)和与无机物质呈反应性的官能团(如水解性甲硅烷基)二者的有机硅化合物通常被称为硅烷偶联剂。经常将它们用作能够形成在无机物质和有机物质之间的键(否则难以键合)的介质。由于这些特性，将硅烷偶联剂广泛地用作无机物质和有机物质的改性剂，结合它们的粘合性助剂和各种添加剂。
其中，作为具有酸酐残基和水解性甲硅烷基的有机硅化合物，3-三甲氧基甲硅烷基丙基琥珀酸酐和3-三乙氧基甲硅烷基丙基琥珀酸酐是商购可得的。它们被用作压敏粘合剂组合物中的增粘剂(专利文献1)，环氧树脂基可固化组合物中的交联剂(专利文献2)和在粘合剂组合物中的添加剂(专利文献3和4)。还将它们用于各个领域如聚酰亚胺树脂改性剂。
已证明有机硅化合物有效地作为各种应用中的硅烷偶联剂。然而，有机硅化合物仍然面对若干问题，包括因其为单体造成的高挥发性，并且因为它们从昂贵的反应物制备而是昂贵的。
引用列表
专利文献1：JP-A H10-140122
专利文献2：JP-A 2006-022158
专利文献3：JP-A 2006-282741
专利文献4：JP-A 2014-515775(WO 2012/139965)
发明内容
本发明的目的在于提供具有酸酐官能度的硅烷改性的共聚物，其完全粘合至无机基材并且是低挥发性的，并且可以从相对廉价的反应物合成。
本发明人已发现，具有酸酐官能团和水解性甲硅烷基的聚丁二烯骨架的共聚物是低挥发性的并且完全粘合至无机基材。
在一个方面，本发明提供了硅烷改性的共聚物，其包含具有式(1)、(2)和(3)的构成单元。
其中，＊表示到邻接单元的键，R1各自独立地为C1-C10烷基或C6-C10芳基，R2各自独立地为C1-C10烷基或C6-C10芳基，和m为1至3的整数，条件是构成单元的排布是任意的。
优选地，所述硅烷改性的共聚物具有至少1,000的数均分子量。
在另一方面，本发明提供了用于制备如上文定义的硅烷改性的共聚物的方法，包括在含铂化合物的催化剂存在下进行包含具有式(1)、(3)和(4)的构成单元的共聚物与具有式(5)的有机硅化合物的氢化硅烷化反应的步骤：
其中，＊具有与上文相同的含义，
其中，R1、R2和m如上文所定义。
本文中还考虑包含所述硅烷改性的共聚物的粘合性改进剂。
在本说明书全文中，化学式中的星号(＊)表示到邻接单元的键。
发明的有益效果
具有聚丁二烯骨架、酸酐官能团和水解性甲硅烷基的硅烷改性的共聚物因为其分子量而是低挥发性的，并且在配混在粘合剂组合物中时开发紧密的粘合性。
优选实施方案的描述
本发明的一个实施方案为包含具有式(1)、(2)和(3)的构成单元的硅烷改性的共聚物。在所述共聚物中，式(1)的构成单元为丁二烯构成单元、式(2)的构成单元为具有水解性甲硅烷基的构成单元和式(3)的构成单元为具有酸酐官能度的构成单元。构成单元的排布是任意的。
其中，R1各自独立地为C1-C10烷基或C6-C10芳基，R2各自独立地为C1-C10烷基或C6-C10芳基，和m为1至3的整数。
合适的C1-C10烷基可以为直链、支链或环状的并且可以包括甲基、乙基、正丙基、异丙基、正丁基、仲丁基、叔丁基、正戊基、正己基、正庚基、正辛基、正壬基、正癸基、环丙基、环丁基、环戊基、环己基、环庚基和环辛基。合适的C6-C10芳基包括苯基、α-萘基和β-萘基。其中，R1优选为直链烷基，更优选甲基或乙基。另外，R2优选为直链烷基，更优选甲基或乙基。
所述硅烷改性的共聚物应当优选具有至少1,000，更优选至少2,000的数均分子量(Mn)，尽管所述Mn没有特别限制。要注意，Mn通过凝胶渗透色谱法(GPC)相对于聚苯乙烯标样测量。
在所述硅烷改性的共聚物中，优选以共聚物全部单元的至少30mol％，更优选至少50mol％的总量包括具有式(1)至(3)的构成单元。
为了增强硅烷改性的共聚物的增粘效果，优选以至少2mol％，更优选至少4mol％的量包括具有式(2)的含水解性甲硅烷基的构成单元和优选以至少1mol％，更优选至少2mol％的量包括具有式(3)的含酸酐的构成单元，基于共聚物的全部单元计。
除了式(1)至(3)的构成单元以外，硅烷改性的共聚物还可以包括具有式(4)的构成单元和/或具有式(7)的构成单元。构成单元的排布也是任意的。
包含式(1)至(3)的构成单元的硅烷改性的共聚物可以通过在含铂化合物的催化剂存在下进行包括具有式(1)、(3)和(4)的构成单元的共聚物与具有式(5)的有机硅化合物的氢化硅烷化反应。
其中，＊具有与上文相同的含义，和R1、R2和m如上文所定义。
包括具有式(1)、(3)和(4)的构成单元的共聚物，即酸酐改性的聚丁二烯是商购可得的。例如，聚丁二烯以商品名Ricon130 MA8、Ricon130 MA13、Ricon130 MA20、Ricon131MA5、Ricon131 MA10、Ricon131 MA17、Ricon131 MA20、Ricon184 MA6和Ricon156 MA17从Cray Valley可得。
这些酸酐改性的聚丁二烯与用作现有技术的含酸酐的有机硅化合物的起始反应物的烯丙基琥珀酸酐相比，可以非常低的成本得到。因此，与现有技术的含酸酐的有机硅化合物相比，可以低成本从这些聚丁二烯合成所述硅烷改性的共聚物。
具有式(5)的有机硅化合物的实例包括三甲氧基硅烷、三乙氧基硅烷、二甲氧基甲基硅烷和二乙氧基甲基硅烷。
用于氢化硅烷化反应的含铂化合物的催化剂没有特别限制。合适的催化剂包括氯铂酸、氯铂酸的醇溶液、铂-1，3-二乙烯基-1，1，3，3-四甲基二硅氧烷络合物的甲苯和二甲苯溶液、四(三苯基膦)合铂、二氯双(三苯基膦)合铂、二氯双乙腈合铂、二氯双苄腈合铂和二氯环辛二烯合铂，以及负载的催化剂如炭载铂、氧化铝载铂和二氧化硅载铂。考虑到在氢化硅烷化时的选择性，零价的铂络合物是优选的，更优选的是铂-1，3-二乙烯基-1，1，3，3-四甲基二硅氧烷络合物的甲苯和二甲苯溶液。
所使用的含铂化合物的催化剂的量没有特别限制。考虑到反应性和生产率，优选以相对于每摩尔具有式(5)的有机硅化合物提供1×10-8至1×10-2摩尔，更优选1×10-7至1×10-3摩尔铂原子的量使用催化剂。
尽管反应在无溶剂体系中进行，但可以使用溶剂。合适的溶剂包括烃熔剂如戊烷、己烷、环己烷、庚烷、异辛烷、苯、甲苯和二甲苯，醚溶剂如乙醚、四氢呋喃和二氧六环，酯溶剂如乙酸乙酯和乙酸丁酯，非质子极性溶剂如N，N-二甲基甲酰胺和氯化的烃溶剂如二氯甲烷和氯仿，其可以单独或混合使用。
尽管氢化硅烷化反应的温度没有特别限制，但是其优选为0℃至升高的温度，更优选0至200℃。升高的温度对于获得适当的反应速率是优选的。在该意义上，反应温度优选为40至110℃，更优选40至90℃。尽管反应时间没有特别限制，但是其优选为1至约60小时，更优选1至30小时，且甚至更优选1至20小时。
通常，含酸酐官能度的有机硅化合物可键合至无机基材如玻璃和金属。本发明的硅烷改性的共聚物还可用作对于无机基材如玻璃和金属的粘合性改进剂。硅烷改性的共聚物为具有多个水解性甲硅烷基和酸酐基团的高分子量化合物。当以0.1至20重量％的量配混在环氧树脂、聚氨酯树脂、丙烯酸系树脂、聚酰亚胺树脂、有机硅树脂或改性的有机硅树脂中时，所述硅烷改性的共聚物有助于赋予比现有技术的含酸酐的有机硅化合物更高的粘合性。
实施例
下文以阐释的方式并且不是以限制的方式给出本发明的实施例。所有份为以重量计(pbw)。Mn为如通过凝胶渗透色谱法(GPC)相对于聚苯乙烯标样测量的数均分子量。通过旋转粘度计在25℃测量粘度。
1)制备硅烷改性的共聚物
实施例1-1
向配备搅拌器、回流冷凝器、滴液漏斗和温度计的1-L可拆卸烧瓶装入207g聚丁二烯Ricon130 MA(Mn＝2,700，由单元(1)、(3)和(4)以67/5/28摩尔比组成，由Cray Vally制备)和一定量(1×10-5mol铂原子)的铂-1，3-二乙烯基-1，1，3，3-四甲基二硅氧烷络合物的甲苯溶液。在75-85℃的内部温度在1小时内将122g三甲氧基硅烷滴加至混合物，将其在80℃熟化3小时。在熟化结束时，将反应混合物在降低的压力下浓缩并且过滤，获得具有6,000mPa·s的粘度和4,300的Mn的棕色浑浊液体。所述Mn数据表明硅烷改性的共聚物由具有式(1)、(3)和(6)的构成单元以67/5/28的(1)/(3)/(6)摩尔比组成。将这命名为硅烷改性的共聚物A。
实施例1-2
向与实施例1-1中相同的烧瓶装入207g聚丁二烯Ricon130 MA(Mn＝2,700，由单元(1)、(3)和(4)以67/5/28摩尔比组成，Cray Vally)和一定量(0.5×10-5mol铂原子)的铂-1，3-二乙烯基-1，1，3，3-四甲基二硅氧烷络合物的甲苯溶液。在75-85℃的内部温度在1小时内将61g三甲氧基硅烷滴加至混合物，将其在80℃熟化3小时。在熟化结束时，将反应混合物在降低的压力下浓缩并且过滤，获得具有5,700mPa·s的粘度和3,500的Mn的棕色浑浊液体。所述Mn数据表明硅烷改性的共聚物由具有式(1)、(3)、(4)和(6)的构成单元以67/5/14/14的(1)/(3)/(4)/(6)摩尔比组成。将这命名为硅烷改性的共聚物B。
实施例1-3
向与实施例1-1中相同的烧瓶装入207g聚丁二烯Ricon130 MA(Mn＝2,700，由单元(1)、(3)和(4)以67/5/28摩尔比组成，由Cray Vally制备)和一定量(0.5×10-5mol铂原子)的铂-1，3-二乙烯基-1，1，3，3-四甲基二硅氧烷络合物的甲苯溶液。在75-85℃的内部温度在1小时内将82g三乙氧基硅烷滴加至混合物，将其在80℃熟化3小时。在熟化结束时，将反应混合物在降低的压力下浓缩并且过滤，获得具有5,200mPa·s的粘度和3,800的Mn的棕色浑浊液体。所述Mn数据表明硅烷改性的共聚物由具有式(1)、(3)、(4)和(8)的构成单元以67/5/14/14的(1)/(3)/(4)/(8)摩尔比组成。将这命名为硅烷改性的共聚物C。
实施例1-4
向与实施例1-1中相同的烧瓶装入223g聚丁二烯Ricon130 MA13(Mn＝2,900，由单元(1)、(3)和(4)以63/9/28摩尔比组成，由Cray Vally制备)和一定量(0.5×10-5mol铂原子)的铂-1，3-二乙烯基-1，1，3，3-四甲基二硅氧烷络合物的甲苯溶液。在75-85℃的内部温度在1小时内将61g三甲氧基硅烷滴加至混合物，将其在80℃熟化3小时。在熟化结束时，将反应混合物在降低的压力下浓缩并且过滤，获得具有16,000mPa·s的粘度和3,700的Mn的棕色浑浊液体。所述Mn数据表明硅烷改性的共聚物由具有式(1)、(3)、(4)和(6)的构成单元以67/5/14/14的(1)/(3)/(4)/(6)摩尔比组成。将这命名为硅烷改性的共聚物D。
硅烷改性的共聚物的挥发性
通过以下测试评价实施例1-1至1-4的硅烷改性的共聚物A至D和比较例1-1的有机硅化合物E的挥发性。要注意的是所述有机硅化合物E为3-三甲氧基甲硅烷基丙基琥珀酸酐(X-12-967，由Shin-Etsu Chemical Co.，Ltd.制备)。
通过将1g化合物(样品)滴加至铝盘，将所述盘在恒温室中在150℃开放地保持3小时，并且称量作为非挥发物的残余物进行测试。较高的非挥发物值表明化合物挥发性低。测试结果示于表1中。
表1
| 化合物 | 非挥发物(％) | |
| 实施例1-1 | 硅烷改性的共聚物A | 99 |
| 实施例1-2 | 硅烷改性的共聚物B | 99 |
| 实施例1-3 | 硅烷改性的共聚物C | 99 |
| 实施例1-4 | 硅烷改性的共聚物D | 99 |
| 比较例1-1 | 有机硅化合物E | 10 |
如从表1看出，实施例1-1至1-4的硅烷改性的共聚物A至D挥发性低。
因为本发明的硅烷改性的共聚物在高温涂覆期间几乎不挥发，所以其可以在以必要的最小量使用时产生必要的性质，提供经济上的益处。其对周围设备不产生或很少产生污染。生产率方面的改进也是可预期的。
2)粘合性改进剂
实施例2-1至2-4和比较例2-1至2-3
通过将实施例1-1至1-4的硅烷改性的共聚物A至D或有机硅化合物E添加至环氧树脂制备环氧树脂组合物。要注意，比较例2-3并不包含任何有机硅化合物。评价环氧树脂组合物的粘合性。具体而言，借助于棒式涂布机将所述环氧树脂组合物涂覆至玻璃板上至10μm的厚度，将涂料在150℃固化1小时，并且通过根据JIS K 5400的交叉划格粘合性测试来测试固化的涂层。将结果表示为每100个分区的未剥离分区的数量。
表2
环氧树脂：YDPN638，Nippon Steel&Sumitomo Metal Corp.
催化剂：2-甲基咪唑
从表2看出，本发明的硅烷改性的共聚物即使以非常小的量添加时也有效改进环氧树脂组合物对玻璃的粘合性。
通过引用将日本专利申请第2016-174727号并入本文中。
尽管已对一些优选的实施方案进行了描述，但根据上述教导可对其进行许多变形和改变。因此可理解，在不脱离所附权利要求的范围的情况下可在具体描述以外实施本发明。
Claims (4)
1.硅烷改性的共聚物，其包含具有式(1)、(2)和(3)的构成单元：
其中，*表示到邻接单元的键，R1各自独立地为C1-C10烷基或C6-C10芳基，R2各自独立地为C1-C10烷基或C6-C10芳基，和m为1至3的整数，条件是构成单元的排布是任意的。
2.权利要求1所述的硅烷改性的共聚物，其具有至少1,000的数均分子量。
3.用于制备权利要求1的硅烷改性的共聚物的方法，包括在含铂化合物的催化剂的存在下、进行包含具有式(1)、(3)和(4)的构成单元的共聚物与具有式(5)的有机硅化合物的氢化硅烷化反应的步骤：
其中，*具有与上文相同的含义，
其中，R1、R2和m如上文所定义。
4.粘合性改进剂，其包含权利要求1所述的硅烷改性的共聚物。
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2016-174727 | 2016-09-07 | ||
| JP2016174727A JP6424868B2 (ja) | 2016-09-07 | 2016-09-07 | シラン変性共重合体、その製造方法および密着向上剤 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN107793500A true CN107793500A (zh) | 2018-03-13 |
Family
ID=59968891
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201710799302.3A Pending CN107793500A (zh) | 2016-09-07 | 2017-09-07 | 硅烷改性的共聚物、制备方法和粘合性改进剂 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US20180066093A1 (zh) |
| EP (1) | EP3293217B8 (zh) |
| JP (1) | JP6424868B2 (zh) |
| KR (1) | KR102341041B1 (zh) |
| CN (1) | CN107793500A (zh) |
| TW (1) | TWI724232B (zh) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP7006542B2 (ja) * | 2018-09-04 | 2022-01-24 | 信越化学工業株式会社 | シラン変性共重合体の製造方法およびそれを含む組成物 |
| JP2024516676A (ja) | 2021-04-28 | 2024-04-16 | ケメタル ゲゼルシャフト ミット ベシュレンクテル ハフツング | シーラント及びプライマー組成物における接着促進剤としてのイソシアネート官能化オルガノシラン |
Citations (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4183844A (en) * | 1976-08-07 | 1980-01-15 | Chemische Werke Huls Aktiengesellschaft | Polymeric adhesion promoters for vulcanizable mixtures of elastomers and mineral fillers |
| US4230815A (en) * | 1975-12-23 | 1980-10-28 | Shin-Etsu Chemical Co., Ltd. | Silicon-containing polybutadiene derivatives and method for the preparation thereof |
| US4396751A (en) * | 1980-06-19 | 1983-08-02 | Chemische Werke Huels Aktiengesellschaft | Homo- and copolymers of 1,3-dienes containing reactive silyl groups, and their preparation and use |
| US4857596A (en) * | 1987-08-12 | 1989-08-15 | Pennwalt Corporation | Polymer bound antioxidant stabilizers |
| CN1041771A (zh) * | 1988-10-13 | 1990-05-02 | 库尔脱沃兹涂料有限公司 | 涂料组合物 |
| CN1074695A (zh) * | 1992-01-23 | 1993-07-28 | 巴斯福拉克和法本股份公司 | 制备多层罩面漆、非水涂料和可自动交联的聚丙烯酸酯树脂的方法 |
| CN1131959A (zh) * | 1993-09-27 | 1996-09-25 | 三洋化成工业株式会社 | 聚合物组合物的水分散液 |
| JP2001131464A (ja) * | 1999-11-05 | 2001-05-15 | Kanegafuchi Chem Ind Co Ltd | 塗料用硬化性樹脂組成物およびそれを塗布してなる塗装物 |
| EP1170346A2 (en) * | 2000-07-07 | 2002-01-09 | National Starch and Chemical Investment Holding Corporation | Die attach adhesives with epoxy resin having allyl or vinyl groups |
| US6664318B1 (en) * | 1999-12-20 | 2003-12-16 | 3M Innovative Properties Company | Encapsulant compositions with thermal shock resistance |
| US20040101689A1 (en) * | 2002-11-26 | 2004-05-27 | Ludovic Valette | Hardener composition for epoxy resins |
| CN1643095A (zh) * | 2002-02-28 | 2005-07-20 | 亨凯尔公司 | 含有机间隔剂的粘合剂组合物及其应用方法 |
| CN1950408A (zh) * | 2004-03-10 | 2007-04-18 | 克雷·瓦利有限公司 | 用于隔离涂料的聚合物含水分散体 |
| CN101472977A (zh) * | 2006-06-20 | 2009-07-01 | 瓦克化学股份公司 | 高分子量有机聚硅氧烷的制备方法 |
| CN101842456A (zh) * | 2007-06-13 | 2010-09-22 | 莫门蒂夫性能材料股份有限公司 | 可湿气固化的接枝改性树脂组合物、其制备方法和采用该树脂组合物粘结基材的方法 |
| US20140121316A1 (en) * | 2012-11-01 | 2014-05-01 | Cray Valley Usa, Llc | Silane functionalized oligomer and rubber compound comprising the same |
| CN104169368A (zh) * | 2012-11-09 | 2014-11-26 | 住友精化株式会社 | 有机硅树脂组合物、有机硅树脂固化物和光学半导体元件封装体 |
| US20150126674A1 (en) * | 2012-07-05 | 2015-05-07 | Sumitomo Rubber Industries, Ltd. | Rubber composition and pneumatic tire |
| WO2015086039A1 (en) * | 2013-12-09 | 2015-06-18 | Trinseo Europe Gmbh | Silane modified elastomeric polymers |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH09263607A (ja) * | 1996-03-28 | 1997-10-07 | Daicel Chem Ind Ltd | ポリエン、その製造方法及びそれを含有する硬化性組成物 |
| JPH10140122A (ja) | 1996-11-14 | 1998-05-26 | Nippon Synthetic Chem Ind Co Ltd:The | 粘着剤組成物 |
| JP4921627B2 (ja) * | 1999-10-14 | 2012-04-25 | 住友ゴム工業株式会社 | 変性ブタジエンゴム組成物 |
| JP4666737B2 (ja) * | 2000-03-08 | 2011-04-06 | 株式会社カネカ | プライマー組成物および接着方法 |
| JP2006022158A (ja) | 2004-07-06 | 2006-01-26 | Yokohama Rubber Co Ltd:The | 硬化性樹脂組成物 |
| JP4788175B2 (ja) | 2005-03-31 | 2011-10-05 | 横浜ゴム株式会社 | 硬化性樹脂組成物 |
| DE102008041279A1 (de) * | 2008-08-15 | 2010-02-18 | Evonik Degussa Gmbh | Silanmodifizierte Polyolefine mit hohem Funktionalisierungsgrad |
| JP2010168528A (ja) * | 2008-10-09 | 2010-08-05 | Ube Ind Ltd | 共役ジエン重合体変性物及びその製造方法、その共役ジエン重合体変性物が含まれたゴム補強剤配合ゴム組成物及びその製造方法、並びにそのゴム補強剤配合ゴム組成物が含まれたタイヤ |
| MX2011010442A (es) * | 2009-04-06 | 2012-01-19 | Cray Valley Technology Usa Llc | Formulaciones de adhesivos de fusion en caliente removibles con sosa caustica. |
| JP2012107141A (ja) * | 2010-11-18 | 2012-06-07 | Sumitomo Rubber Ind Ltd | 空気入りタイヤ |
| ES2443163T3 (es) | 2011-04-12 | 2014-02-18 | Henkel Ireland Ltd. | Adhesivo de cianoacrilato con resistencia al agua mejorada |
| US20160185883A1 (en) * | 2014-12-29 | 2016-06-30 | Empire Technology Development Llc | Organo-silane modified polymers and methods for their preparation and use |
| JP2016174727A (ja) | 2015-03-20 | 2016-10-06 | ブラザー工業株式会社 | ミシン |
| JP6128247B2 (ja) * | 2016-03-10 | 2017-05-17 | 信越化学工業株式会社 | 有機ケイ素化合物、並びにそれを用いたゴム用配合剤およびゴム組成物 |
-
2016
- 2016-09-07 JP JP2016174727A patent/JP6424868B2/ja active Active
-
2017
- 2017-08-30 US US15/691,252 patent/US20180066093A1/en not_active Abandoned
- 2017-09-04 KR KR1020170112682A patent/KR102341041B1/ko active IP Right Grant
- 2017-09-05 EP EP17189330.8A patent/EP3293217B8/en active Active
- 2017-09-06 TW TW106130367A patent/TWI724232B/zh active
- 2017-09-07 CN CN201710799302.3A patent/CN107793500A/zh active Pending
Patent Citations (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4230815A (en) * | 1975-12-23 | 1980-10-28 | Shin-Etsu Chemical Co., Ltd. | Silicon-containing polybutadiene derivatives and method for the preparation thereof |
| US4183844A (en) * | 1976-08-07 | 1980-01-15 | Chemische Werke Huls Aktiengesellschaft | Polymeric adhesion promoters for vulcanizable mixtures of elastomers and mineral fillers |
| US4396751A (en) * | 1980-06-19 | 1983-08-02 | Chemische Werke Huels Aktiengesellschaft | Homo- and copolymers of 1,3-dienes containing reactive silyl groups, and their preparation and use |
| US4857596A (en) * | 1987-08-12 | 1989-08-15 | Pennwalt Corporation | Polymer bound antioxidant stabilizers |
| CN1041771A (zh) * | 1988-10-13 | 1990-05-02 | 库尔脱沃兹涂料有限公司 | 涂料组合物 |
| CN1074695A (zh) * | 1992-01-23 | 1993-07-28 | 巴斯福拉克和法本股份公司 | 制备多层罩面漆、非水涂料和可自动交联的聚丙烯酸酯树脂的方法 |
| CN1131959A (zh) * | 1993-09-27 | 1996-09-25 | 三洋化成工业株式会社 | 聚合物组合物的水分散液 |
| JP2001131464A (ja) * | 1999-11-05 | 2001-05-15 | Kanegafuchi Chem Ind Co Ltd | 塗料用硬化性樹脂組成物およびそれを塗布してなる塗装物 |
| US6664318B1 (en) * | 1999-12-20 | 2003-12-16 | 3M Innovative Properties Company | Encapsulant compositions with thermal shock resistance |
| EP1170346A2 (en) * | 2000-07-07 | 2002-01-09 | National Starch and Chemical Investment Holding Corporation | Die attach adhesives with epoxy resin having allyl or vinyl groups |
| CN1643095A (zh) * | 2002-02-28 | 2005-07-20 | 亨凯尔公司 | 含有机间隔剂的粘合剂组合物及其应用方法 |
| US20040101689A1 (en) * | 2002-11-26 | 2004-05-27 | Ludovic Valette | Hardener composition for epoxy resins |
| CN1950408A (zh) * | 2004-03-10 | 2007-04-18 | 克雷·瓦利有限公司 | 用于隔离涂料的聚合物含水分散体 |
| CN101472977A (zh) * | 2006-06-20 | 2009-07-01 | 瓦克化学股份公司 | 高分子量有机聚硅氧烷的制备方法 |
| CN101842456A (zh) * | 2007-06-13 | 2010-09-22 | 莫门蒂夫性能材料股份有限公司 | 可湿气固化的接枝改性树脂组合物、其制备方法和采用该树脂组合物粘结基材的方法 |
| US20150126674A1 (en) * | 2012-07-05 | 2015-05-07 | Sumitomo Rubber Industries, Ltd. | Rubber composition and pneumatic tire |
| US20140121316A1 (en) * | 2012-11-01 | 2014-05-01 | Cray Valley Usa, Llc | Silane functionalized oligomer and rubber compound comprising the same |
| CN104169368A (zh) * | 2012-11-09 | 2014-11-26 | 住友精化株式会社 | 有机硅树脂组合物、有机硅树脂固化物和光学半导体元件封装体 |
| WO2015086039A1 (en) * | 2013-12-09 | 2015-06-18 | Trinseo Europe Gmbh | Silane modified elastomeric polymers |
Also Published As
| Publication number | Publication date |
|---|---|
| KR102341041B1 (ko) | 2021-12-20 |
| TW201811845A (zh) | 2018-04-01 |
| EP3293217B1 (en) | 2019-02-13 |
| EP3293217B8 (en) | 2019-03-27 |
| EP3293217A1 (en) | 2018-03-14 |
| US20180066093A1 (en) | 2018-03-08 |
| TWI724232B (zh) | 2021-04-11 |
| JP2018039909A (ja) | 2018-03-15 |
| KR20180028030A (ko) | 2018-03-15 |
| JP6424868B2 (ja) | 2018-11-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN101291941B (zh) | 新的有机硅烷化合物 | |
| JP6930917B2 (ja) | 硬化性シロキサン組成物 | |
| EP3119847B1 (en) | Alkoxy group-containing silicones with reactive functional groups of defined reactivity | |
| KR20100095510A (ko) | 폴리실록산 및 그의 제조 방법 및 경화물의 제조 방법 | |
| EP0530496B1 (en) | Organosilicon compounds and method for preparing same | |
| CN111499877A (zh) | 一种有机硅改性的环氧树脂的制备方法 | |
| CN107793500A (zh) | 硅烷改性的共聚物、制备方法和粘合性改进剂 | |
| KR102138758B1 (ko) | 산 무수물기 함유 오르가노실록산 및 그의 제조 방법 | |
| WO2014099497A2 (en) | Alkoxy polysiloxanes and methods of making alkoxy silanes and siloxanes | |
| CN109863218A (zh) | 包含胍催化剂和增粘剂的可交联硅树脂混合物 | |
| CN111363103A (zh) | 一种加成型有机硅胶粘剂用增粘剂的制备方法 | |
| JP2546104B2 (ja) | シリコーン変性酸無水物及びその製造方法 | |
| EP3575358B1 (en) | Room temperature-vulcanizing silane-containing resin composition and mounting circuit substrate | |
| CN113968973B (zh) | 一种环氧基硅氧烷、环氧基聚硅氧烷-硅橡胶复合物、其制备方法及其用途 | |
| CN109796930A (zh) | 一种有机硅三防胶及其制备方法与应用 | |
| WO2007046646A1 (en) | Novel organic silane compound | |
| CN109851629A (zh) | 一种单组份硅橡胶用硅烷化炔基抑制剂的制备方法 | |
| JP7006542B2 (ja) | シラン変性共重合体の製造方法およびそれを含む組成物 | |
| WO2023199747A1 (ja) | シラン変性共重合体、その製造方法およびそれを含む組成物 | |
| JP6844384B2 (ja) | 液状ケイ素化合物及びその製造方法 | |
| CN116284792A (zh) | 一种改性聚硅氧烷聚合物及其制备方法和有机硅涂料 | |
| KR20150039687A (ko) | 유기 규소 화합물 및 그의 제조 방법, 접착성 조성물 및 물품 | |
| KR20090053719A (ko) | 유기 규소 화합물 및 그것을 포함하는 액정 소자용 감압 접착제 조성물 | |
| JP2002293991A (ja) | 室温硬化性混成シリコーン | |
| CN110372741A (zh) | 含甘脲环的有机硅化合物及制备方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20180313 |
|
| WD01 | Invention patent application deemed withdrawn after publication |