CN115627120B - Single-component solvent-free addition type organosilicon three-proofing coating - Google Patents
Single-component solvent-free addition type organosilicon three-proofing coating Download PDFInfo
- Publication number
- CN115627120B CN115627120B CN202211319809.1A CN202211319809A CN115627120B CN 115627120 B CN115627120 B CN 115627120B CN 202211319809 A CN202211319809 A CN 202211319809A CN 115627120 B CN115627120 B CN 115627120B
- Authority
- CN
- China
- Prior art keywords
- platinum catalyst
- vinyl
- addition type
- delayed
- solvent
- 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.)
- Active
Links
- 239000011248 coating agent Substances 0.000 title claims abstract description 28
- 238000000576 coating method Methods 0.000 title claims abstract description 28
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims abstract description 85
- 239000003054 catalyst Substances 0.000 claims abstract description 43
- 229910052697 platinum Inorganic materials 0.000 claims abstract description 40
- 230000003111 delayed effect Effects 0.000 claims abstract description 22
- 229920005989 resin Polymers 0.000 claims abstract description 13
- 239000011347 resin Substances 0.000 claims abstract description 13
- 239000004970 Chain extender Substances 0.000 claims abstract description 12
- 239000003112 inhibitor Substances 0.000 claims abstract description 12
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 10
- 238000002156 mixing Methods 0.000 claims abstract description 7
- 239000012752 auxiliary agent Substances 0.000 claims abstract description 4
- -1 polysiloxane Polymers 0.000 claims description 30
- 239000001257 hydrogen Substances 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 27
- 229920001296 polysiloxane Polymers 0.000 claims description 27
- 229920002554 vinyl polymer Polymers 0.000 claims description 21
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
- 239000000654 additive Substances 0.000 claims description 9
- 230000000996 additive effect Effects 0.000 claims description 9
- 230000000694 effects Effects 0.000 claims description 9
- 239000007788 liquid Substances 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 238000003756 stirring Methods 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 239000008096 xylene Substances 0.000 claims description 6
- QYLFHLNFIHBCPR-UHFFFAOYSA-N 1-ethynylcyclohexan-1-ol Chemical compound C#CC1(O)CCCCC1 QYLFHLNFIHBCPR-UHFFFAOYSA-N 0.000 claims description 5
- 238000004821 distillation Methods 0.000 claims description 5
- 238000001035 drying Methods 0.000 claims description 5
- 238000005406 washing Methods 0.000 claims description 5
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 claims description 4
- 238000000605 extraction Methods 0.000 claims description 4
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 3
- FMGBDYLOANULLW-UHFFFAOYSA-N 3-isocyanatopropyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCCN=C=O FMGBDYLOANULLW-UHFFFAOYSA-N 0.000 claims description 3
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 3
- 229920001843 polymethylhydrosiloxane Polymers 0.000 claims description 3
- CEBKHWWANWSNTI-UHFFFAOYSA-N 2-methylbut-3-yn-2-ol Chemical compound CC(C)(O)C#C CEBKHWWANWSNTI-UHFFFAOYSA-N 0.000 claims description 2
- KSLSOBUAIFEGLT-UHFFFAOYSA-N 2-phenylbut-3-yn-2-ol Chemical compound C#CC(O)(C)C1=CC=CC=C1 KSLSOBUAIFEGLT-UHFFFAOYSA-N 0.000 claims description 2
- DTGUZRPEDLHAAO-UHFFFAOYSA-N 3-methylhex-1-yn-3-ol Chemical compound CCCC(C)(O)C#C DTGUZRPEDLHAAO-UHFFFAOYSA-N 0.000 claims description 2
- PDHZEDLZPIMDSR-UHFFFAOYSA-N 3-methylundec-1-yn-3-ol Chemical compound CCCCCCCCC(C)(O)C#C PDHZEDLZPIMDSR-UHFFFAOYSA-N 0.000 claims description 2
- 239000004971 Cross linker Substances 0.000 claims description 2
- 229920002050 silicone resin Polymers 0.000 claims 2
- 238000003860 storage Methods 0.000 abstract description 6
- 150000007514 bases Chemical class 0.000 abstract description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000000034 method Methods 0.000 description 8
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 7
- 229910052710 silicon Inorganic materials 0.000 description 7
- 239000010703 silicon Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 239000000853 adhesive Substances 0.000 description 5
- 230000001070 adhesive effect Effects 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000011056 performance test Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000002318 adhesion promoter Substances 0.000 description 3
- 238000013461 design Methods 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 230000004224 protection Effects 0.000 description 3
- 229920002379 silicone rubber Polymers 0.000 description 3
- 150000003384 small molecules Chemical class 0.000 description 3
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 2
- ZKKBIZXAEDFPNL-HWKANZROSA-N (e)-3-(dimethylamino)prop-2-enenitrile Chemical compound CN(C)\C=C\C#N ZKKBIZXAEDFPNL-HWKANZROSA-N 0.000 description 2
- VMELXYJYSXXORF-ZZXKWVIFSA-N (e)-3-cyclopentylprop-2-enenitrile Chemical compound N#C\C=C\C1CCCC1 VMELXYJYSXXORF-ZZXKWVIFSA-N 0.000 description 2
- NNTRMVRTACZZIO-UHFFFAOYSA-N 3-isocyanatopropyl-dimethoxy-methylsilane Chemical compound CO[Si](C)(OC)CCCN=C=O NNTRMVRTACZZIO-UHFFFAOYSA-N 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- 229950005499 carbon tetrachloride Drugs 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- FGBJXOREULPLGL-UHFFFAOYSA-N ethyl cyanoacrylate Chemical compound CCOC(=O)C(=C)C#N FGBJXOREULPLGL-UHFFFAOYSA-N 0.000 description 2
- 229940053009 ethyl cyanoacrylate Drugs 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- QEQBMZQFDDDTPN-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy benzenecarboperoxoate Chemical compound CC(C)(C)OOOC(=O)C1=CC=CC=C1 QEQBMZQFDDDTPN-UHFFFAOYSA-N 0.000 description 1
- YSLYJMRRAPPURP-OWOJBTEDSA-N (e)-3-(4-aminophenyl)prop-2-enenitrile Chemical compound NC1=CC=C(\C=C\C#N)C=C1 YSLYJMRRAPPURP-OWOJBTEDSA-N 0.000 description 1
- GQCABHQDRZQIOP-ARJAWSKDSA-N (z)-3-(1h-indol-3-yl)prop-2-enenitrile Chemical compound C1=CC=C2C(\C=C/C#N)=CNC2=C1 GQCABHQDRZQIOP-ARJAWSKDSA-N 0.000 description 1
- QWOVEJBDMKHZQK-UHFFFAOYSA-N 1,3,5-tris(3-trimethoxysilylpropyl)-1,3,5-triazinane-2,4,6-trione Chemical compound CO[Si](OC)(OC)CCCN1C(=O)N(CCC[Si](OC)(OC)OC)C(=O)N(CCC[Si](OC)(OC)OC)C1=O QWOVEJBDMKHZQK-UHFFFAOYSA-N 0.000 description 1
- OYUNTGBISCIYPW-UHFFFAOYSA-N 2-chloroprop-2-enenitrile Chemical compound ClC(=C)C#N OYUNTGBISCIYPW-UHFFFAOYSA-N 0.000 description 1
- VYULCLGNLSTLFX-UHFFFAOYSA-N 3-(benzenesulfonyl)prop-2-enenitrile Chemical compound N#CC=CS(=O)(=O)C1=CC=CC=C1 VYULCLGNLSTLFX-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
- 230000006750 UV protection Effects 0.000 description 1
- 150000008360 acrylonitriles Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- VXTQKJXIZHSXBY-UHFFFAOYSA-N butan-2-yl 2-methylprop-2-enoate Chemical compound CCC(C)OC(=O)C(C)=C VXTQKJXIZHSXBY-UHFFFAOYSA-N 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052681 coesite Inorganic materials 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229910052906 cristobalite Inorganic materials 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000013467 fragmentation Methods 0.000 description 1
- 238000006062 fragmentation reaction Methods 0.000 description 1
- 238000006459 hydrosilylation reaction Methods 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000007712 rapid solidification Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 229910052682 stishovite Inorganic materials 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
- FRGPKMWIYVTFIQ-UHFFFAOYSA-N triethoxy(3-isocyanatopropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCN=C=O FRGPKMWIYVTFIQ-UHFFFAOYSA-N 0.000 description 1
- NBXZNTLFQLUFES-UHFFFAOYSA-N triethoxy(propyl)silane Chemical compound CCC[Si](OCC)(OCC)OCC NBXZNTLFQLUFES-UHFFFAOYSA-N 0.000 description 1
- 238000007039 two-step reaction Methods 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D183/00—Coating compositions 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; Coating compositions based on derivatives of such polymers
- C09D183/04—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
- C08G77/38—Polysiloxanes modified by chemical after-treatment
-
- 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
- C08G77/38—Polysiloxanes modified by chemical after-treatment
- C08G77/382—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon
- C08G77/388—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon containing nitrogen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/14—Paints containing biocides, e.g. fungicides, insecticides or pesticides
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/65—Additives macromolecular
-
- 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
- C08G2150/00—Compositions for coatings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/08—Stabilised against heat, light or radiation or oxydation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Plant Pathology (AREA)
- Paints Or Removers (AREA)
Abstract
The invention relates to the technical field of organosilicon three-proofing coating, in particular to a single-component solvent-free addition type organosilicon three-proofing coating, which comprises the following components: the single-component solvent-free organosilicon three-proofing coating is prepared by physically mixing the basic compound, the cross-linking agent, the chain extender, the toughening resin, the tackifying auxiliary agent, the delayed platinum catalyst, the inhibitor and the like, and realizes the storage stability of high-temperature rapid curing and normal-temperature non-curing.
Description
Technical Field
The invention belongs to the field of organic silicon three-proofing coating, and particularly relates to a single-component solvent-free addition type organic silicon three-proofing coating.
Background
The organic silicon rubber has excellent weather resistance, high and low temperature resistance, high insulation, good hydrophobicity and other performance advantages, so that the organic silicon rubber is widely applied to the protection of electronic circuit boards; however, most of the current organic silicon rubber applied to the field of three proofing belongs to a condensation organic silicon system, a solvent is generally added in the use process, small molecules are released in the curing process, pollution is caused to the environment, and the small molecules have obvious corrosion to a circuit board in the long-term use process, so that the reliability of an electronic product is reduced, and the service life of the electronic product is further threatened.
The addition type organosilicon mainly depends on a hydrosilylation curing mechanism, has no small molecule release, has the performance characteristics of environmental protection and no corrosion, but is not effectively applied to the field of electronic three prevention, because on one hand, the addition type organosilicon curing agent has larger reactivity with a catalyst, and can not realize single-component storage, and on the other hand, the addition type organosilicon has larger inertia of molecular groups, has poorer adhesive force with each substrate, and can not play a role in protection.
Disclosure of Invention
The invention aims to solve the technical problems of overcoming the defects and the shortcomings in the background art, providing a preparation method and application of a single-component solvent-free addition type organosilicon three-proofing coating, and mainly solving the technical problems of single-component storage and high adhesive force.
In order to solve the technical problems, the technical scheme provided by the invention is as follows:
the single-component solvent-free addition type organosilicon three-proofing coating is characterized by being prepared from basic compounds, cross-linking agents, chain extenders, toughening resins, tackifying assistants, delayed platinum catalysts, inhibitors and other compounds through physical mixing, and comprises the following main components:
base Compounds 10-100
0.1 to 10 portions of cross-linking agent
Chain extender 0.1-10
10 to 50 portions of toughening resin
1-10 parts of tackifying assistant
Delayed platinum catalyst 0.01-1
Inhibitor 0.01-1
Preferably, the base compound is one or more compositions of vinyl terminated linear methyl vinyl polysiloxanes having the following structural formula;
Vi-Si(CH 3 ) 2 —O—(Si(CH 3 ) 2 —O)n—Si(CH 3 ) 2 —Vi
wherein n is 2-100, the vinyl content is preferably 0.2% -10% (mass ratio), and the viscosity is 100-10000 mPa.s.
Preferably, the crosslinker is one or more compositions of pendant hydrogen polymethylhydrosiloxanes having the following structural formula;
Si(CH 3 ) 3 —O-(SiHCH 3 —O)n—Si(CH 3 ) 3
wherein n is 1-100, and the preferred H content is 0.1% -1% (mass ratio).
Preferably, the chain extender is one or more compositions of double-ended hydrosiloxanes having the structural formula;
H-Si(CH 3 ) 2 —O-(Si(CH 3 ) 2 —O)n—Si(CH 3 ) 2 -H
wherein n is 2-100, and the preferable H content is 0.01% -0.2% (mass ratio).
Preferably, the tackifying additive is vinyl MQ silicon resin, the vinyl content is 1-20%, and the tackifying additive has the following structural formula;
(MeSiO0.5)a(ViMeSiO0.5)b(SiO2)c
preferably, the tackifying additive is a self-made compound and is mainly prepared from acrylic ester monomers, hydrogen-containing polysiloxane and isocyanate compounds through a two-step reaction;
the main synthesis method comprises the following steps:
firstly, accurately adding 1-20g of hydrogen-containing polysiloxane and 1-30 g acrylate monomer compound into a three-neck flask according to a set molar ratio, dissolving the mixture in a solvent, dropwise adding 0.1-1 g high-activity platinum catalyst solution, controlling the temperature to be 40-120 ℃, and reacting for 2-8 hours to obtain transparent uniform liquid;
and secondly, adding 1-20g of isocyanate compound according to the proportion, controlling the temperature to be 40-120 ℃ for reaction for 2-8 hours, and distilling the transparent uniform liquid under reduced pressure to remove the solvent, thus obtaining the tackifying additive.
Preferably, the hydrogen-containing polysiloxane is terminal hydrogen-containing polysiloxane, and the hydrogen-containing mass ratio is 0.05-0.5 wt%; the acrylic ester monomer is one or a plurality of compositions of acrylic acid, methyl acrylate, ethyl acrylate, butyl acrylate, 2-methyl methacrylate, 2-ethyl methacrylate, 2-butyl methacrylate, tert-butyl acrylate, hydroxyethyl methacrylate, homologues and derivatives thereof;
the solvent is one or more of ethyl acetate, butyl acetate, toluene, xylene, cyclohexane, cyclohexanol, n-butanol, chloroform, tetrachloromethane and dichloromethane;
the isocyanate compound is one or more of isocyanatopropyl triethoxysilane, 3-isocyanatopropyl trimethoxysilane, 3-isocyanatopropyl methyl dimethoxysilane, 1,3, 5-tris (trimethoxysilylpropyl) isocyanurate, and homologs and derivatives thereof; the platinum catalyst is a high-activity platinum catalyst, and the Pt content is 3000-6000ppm.
Preferably, the delayed platinum catalyst is a self-made compound, and is mainly prepared from a high-activity platinum catalyst and a nitrile compound through a polymerization reaction of a free radical reversible addition-fragmentation transfer (RAFT) method, and the main synthesis method comprises the following steps:
firstly, adding 10-100 g platinum catalyst and 200-500 g solvent into a flask, and mixing by a mechanical stirrer;
secondly, stirring the mixture at 50-80 ℃ for 1-5h, then sequentially adding 1-20 acrylonitrile compounds, and mixing and stirring for 1-5 h;
and thirdly, dropwise adding 0-2g of catalyst, reacting for 8-10h at 50-180 ℃, extracting, distilling under reduced pressure, washing and drying to obtain the target compound delayed platinum catalyst.
Preferably, the solvent is one or more of ethyl acetate, butyl acetate, toluene, xylene, cyclohexane, cyclohexanol, n-butanol, chloroform, tetrachloromethane and dichloromethane;
the platinum catalyst is a high-activity platinum catalyst, and the Pt content is 5000-8000ppm. The nitrile compounds acrylonitrile compounds include, but are not limited to, acrylonitrile, methacrylonitrile, ethyl cyanoacrylate, 2-chloroacrylonitrile, 2-bromoacrylonitrile 3-phenylacrylonitrile, 3-cyclopentylacrylonitrile, 3-diphenylacrylonitrile, 3- (dimethylamino) acrylonitrile, 3- (benzenesulfonyl) acrylonitrile, (E) -3- (4-aminophenyl) acrylonitrile, (Z) -3- (1H-indol-3-yl) acrylonitrile, trans-3- (dimethylamino) acrylonitrile;
the catalyst is a free radical polymerization initiator including, but not limited to, one or more of azobisisobutyronitrile, azobisisoheptonitrile, dibenzoyl peroxide, t-butyl peroxybenzoate, t-butyl hydroperoxide, lauroyl peroxide.
Preferably, the inhibitor is an alkynyl-and polyvinyl-containing compound including, but not limited to, one or more of 1-ethynyl cyclohexanol, 3-methyl-1-butyn-3-ol, 3-phenyl-1-butyn-3-ol, 3-propyl-1-butyn-3-ol, 3-octyl-1-butyn-3-ol.
Compared with the prior art, the invention has the beneficial effects that:
the main innovation of the invention is embodied in the three aspects, namely, the delayed platinum catalyst is obtained through autonomous design synthesis; secondly, obtaining a tackifying auxiliary agent through autonomous design synthesis, wherein the tackifying auxiliary agent introduces active groups on the molecules of the polymethyl hydrosiloxane through a platinum catalyst by a two-step method; thirdly, through formulation design and addition of toughening resin; in addition, the storage stability of the single-component addition type organic silicon coating is excellent in adhesive force between the addition type organic silicon coating and a PCB circuit board, so that the single-component solvent-free organic silicon three-proofing coating prepared by the invention realizes the storage stability of high-temperature rapid solidification and normal-temperature non-solidification.
Drawings
FIG. 1 is a table 1 of performance test results of the three-proofing coating adhesive prepared in each example of the present invention;
FIG. 2 is a diagram of the tackifier synthesis mechanism of the present invention;
FIG. 3 is a diagram showing the mechanism of synthesis of a delayed platinum catalyst according to the present invention.
Detailed Description
The following description of the embodiments of the present invention will be made clearly and completely with reference to the accompanying drawings, in which it is apparent that the embodiments described are only some embodiments of the present invention, but not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
Example 1:
a single-component solvent-free addition type organosilicon three-proofing coating comprises the following components in parts by mass:
base Compound 100
Toughening resin 20
Delayed platinum catalyst 0.5
Inhibitor 0.1
In this example, the above base compound was vinyl polysiloxane with a vinyl mass ratio of 0.32% by weight, the crosslinking agent was side hydrogen polysiloxane with a hydrogen mass ratio of 0.32% by weight, the chain extender was terminal hydrogen polysiloxane with a hydrogen mass ratio of 0.12%, the toughening resin was vinyl MQ silicone with a vinyl mass ratio of 4.5% by weight, the inhibitor was 1-ethynyl cyclohexanol, and the adhesion promoter and the delayed platinum catalyst were self-made in the laboratory.
The preparation method of the tackifying additive comprises the following steps:
firstly, accurately adding 20g of terminal hydrogen-containing polysiloxane with the hydrogen mass ratio of 0.12% and 22g of hydroxyethyl acrylate into a three-neck flask according to a set molar ratio, dissolving the mixture into ethyl acetate, dropwise adding 0.5 g high-activity platinum catalyst (Pt mass content is 5000 ppm) solution, controlling the temperature to 100 ℃, and reacting for 8 hours to obtain transparent uniform liquid;
and secondly, adding 8g of 3-isocyanatopropyl trimethoxy silane according to the proportion, controlling the temperature to 120 ℃, reacting for 6 hours, and distilling the transparent uniform liquid under reduced pressure to remove the solvent to obtain the tackifying assistant.
The preparation method of the delayed platinum catalyst comprises the following steps:
first, 20g platinum catalyst (pt content 6000 ppm) and 400 g xylene solvent were added to a flask and mixed by a mechanical stirrer;
secondly, stirring the mixture at 80 ℃ for 4 hours, then adding 15g of acrylonitrile, and mixing and stirring 5. 5 h;
thirdly, 1g of azodiisobutyronitrile is added dropwise, and the reaction is carried out for 10 hours at 120 ℃, and the delayed platinum catalyst is obtained through extraction, reduced pressure distillation, washing and drying;
the single-component solvent-free addition type organosilicon three-proofing coating prepared by the method is subjected to performance test and comparison, and the results are shown in Table 1.
Example 2:
a single-component solvent-free addition type organosilicon three-proofing coating comprises the following components in parts by mass:
base Compound 80
Crosslinking agent 1.5
Chain extender 8
Toughening resin 20
Tackifying auxiliary 15
Delayed platinum catalyst 0.3
Inhibitor 0.1
In this example, the above base compound was vinyl polysiloxane with a vinyl mass ratio of 0.42% by weight, the crosslinking agent was side hydrogen polysiloxane with a hydrogen mass ratio of 0.28% by weight, the chain extender was terminal hydrogen polysiloxane with a hydrogen mass ratio of 0.12%, the toughening resin was vinyl MQ silicone with a vinyl mass ratio of 4.5% by weight, the inhibitor was 1-ethynyl cyclohexanol, and the adhesion promoter and the delayed platinum catalyst were self-made in the laboratory.
The preparation method of the tackifying additive comprises the following steps:
firstly, accurately adding 15g of terminal hydrogen-containing polysiloxane with the hydrogen mass ratio of 0.18% and 32g of hydroxyethyl methacrylate into a three-neck flask according to a set molar ratio, dissolving the mixture into toluene, dropwise adding 0.5 g high-activity platinum catalyst (4000 ppm of Pt mass content) solution, controlling the temperature to 80 ℃, and reacting for 8 hours to obtain transparent uniform liquid;
and secondly, adding 8g of isocyanic propyl triethoxysilane according to the proportion, controlling the temperature to 120 ℃ for reaction for 6 hours, and distilling the transparent uniform liquid under reduced pressure to remove the solvent to obtain the tackifying assistant.
The preparation method of the delayed platinum catalyst comprises the following steps:
in the first step, 18 g platinum catalyst (pt content 6000 ppm) was added to the flask with 400 g xylene solvent and mixed by mechanical stirrer. In the second step, the mixture was stirred at 80℃for 4h, then 20g ethyl cyanoacrylate was added and mixed with stirring 5 h. Thirdly, 1g of benzoyl peroxide is added dropwise, the mixture is reacted for 10 hours at 120 ℃, and the delayed platinum catalyst is obtained through extraction, reduced pressure distillation, washing and drying.
The single-component solvent-free addition type organosilicon three-proofing coating prepared by the method is subjected to performance test and comparison, and the results are shown in Table 1.
Example 3:
a single-component solvent-free addition type organosilicon three-proofing coating comprises the following components in parts by mass:
base Compound 100
Crosslinking agent 4
Toughening resin 20
Tackifying auxiliary 20
Delayed platinum catalyst 0.2
Inhibitor 0.1
In this example, the above base compound was vinyl polysiloxane with a vinyl mass ratio of 0.32% by weight, the crosslinking agent was side hydrogen polysiloxane with a hydrogen mass ratio of 0.50% by weight, the chain extender was terminal hydrogen polysiloxane with a hydrogen mass ratio of 0.10%, the toughening resin was vinyl MQ silicone with a vinyl mass ratio of 6.4% by weight, the inhibitor was 1-ethynyl cyclohexanol, and the adhesion promoter and the delayed platinum catalyst were self-made in the laboratory.
The preparation method of the tackifying additive comprises the following steps:
firstly, accurately adding 20g of terminal hydrogen-containing polysiloxane with the hydrogen mass ratio of 0.10% and 22g of hydroxyethyl acrylate into a three-neck flask according to a set molar ratio, dissolving in dimethylbenzene, dropwise adding 0.5 g high-activity platinum catalyst (4000 ppm of Pt mass content) solution, controlling the temperature to 80 ℃, and reacting for 6h to obtain transparent uniform liquid;
and secondly, adding 8g of 3-isocyanatopropyl methyl dimethoxy silane according to the proportion, controlling the temperature to 120 ℃, reacting for 6 hours, and distilling under reduced pressure to remove the solvent, thus obtaining the tackifying additive.
The preparation method of the delayed platinum catalyst comprises the following steps:
first, 18 g platinum catalyst (pt content 6000 ppm) and 400 g xylene solvent were added to a flask and mixed by a mechanical stirrer;
second, the mixture was stirred at 80 ℃ for 4h, then 25 g of 3-cyclopentylacrylonitrile was added, and mixed and stirred for 5 h;
thirdly, 1g of azodiisoheptonitrile is added dropwise, and the reaction is carried out at 120 ℃ for 9 h, and the delayed platinum catalyst is obtained through extraction, reduced pressure distillation, washing and drying.
The single-component solvent-free addition type organosilicon three-proofing coating prepared by the method is subjected to performance test and comparison, and the results are shown in Table 1.
The performances of the single-component solvent-free addition type organosilicon three-proofing coating and similar products at home and abroad in the embodiment are tested, and the results are shown in Table 1.
As shown in experimental data in Table 1, the single-component solvent-free addition type organosilicon three-proofing coating prepared by the invention has extremely low viscosity, so that the operation manufacturability is better, compared with foreign similar products, the adhesive force and the mildew resistance are higher, the oil resistance, the solvent resistance, the ultraviolet resistance and the smoke resistance can all reach the same level, and meanwhile, the single-component solvent-free addition type organosilicon three-proofing coating prepared by the invention belongs to addition type silica gel, has no byproduct generation, is safe and environment-friendly, and has the storage temperature.
It will be evident to those skilled in the art that the invention is not limited to the details of the foregoing illustrative embodiments, and that the present invention may be embodied in other specific forms without departing from the spirit or essential characteristics thereof. The present embodiments are, therefore, to be considered in all respects as illustrative and not restrictive, the scope of the invention being indicated by the appended claims rather than by the foregoing description, and all changes which come within the meaning and range of equivalency of the claims are therefore intended to be embraced therein. Any reference sign in a claim should not be construed as limiting the claim concerned.
Claims (6)
1. The single-component solvent-free addition type organosilicon three-proofing coating is characterized by comprising the following components in parts by weight:
base Compounds 10-100
0.1 to 10 portions of cross-linking agent
Chain extender 0.1-10
10 to 50 portions of toughening resin
1-10 parts of tackifying assistant
Delayed platinum catalyst 0.01-1
0.01-1 parts of inhibitor;
the preparation method of the tackifying additive comprises the following steps:
firstly, accurately adding 20g of terminal hydrogen-containing polysiloxane with the hydrogen mass ratio of 0.12% and 22g of hydroxyethyl acrylate into a three-neck flask according to a set molar ratio, dissolving the mixture into ethyl acetate, dropwise adding 0.5 g high-activity platinum catalyst solution, controlling the temperature to 100 ℃, and reacting for 8 hours to obtain transparent uniform liquid, wherein the mass content of the high-activity platinum catalyst is 5000ppm;
secondly, 8g of 3-isocyanatopropyl trimethoxy silane is added according to the proportion, the temperature is controlled at 120 ℃, the reaction is carried out for 6 hours, transparent uniform liquid is obtained, and the solvent is removed by reduced pressure distillation, thus obtaining the tackifying auxiliary agent;
the preparation method of the delayed platinum catalyst comprises the following steps:
the first step, adding 20g platinum catalyst and 400 g xylene solvent into a flask, and mixing by a mechanical stirrer, wherein the mass content of the platinum catalyst is 6000ppm;
secondly, stirring the mixture at 80 ℃ for 4 hours, then adding 15g of acrylonitrile, and mixing and stirring 5. 5 h;
thirdly, 1g of azodiisobutyronitrile is added dropwise, and the reaction is carried out for 10 hours at 120 ℃, and the delayed platinum catalyst is obtained through extraction, reduced pressure distillation, washing and drying.
2. The one-part solventless addition type silicone three-way coating according to claim 1, wherein the base compound is one or more compositions of vinyl-terminated linear methyl vinyl polysiloxane;
the structural formula is as follows: vi-Si (CH) 3 ) 2 —O—(Si(CH 3 ) 2 —O) n —Si(CH 3 ) 2 —Vi,
n is 2-100, vinyl content is 0.2-10 wt% and viscosity is 100-10000 mPa.s.
3. The one-part solventless addition type silicone tri-proof coating of claim 1 wherein the crosslinker is one or more compositions of pendant hydrogen polymethylhydrosiloxanes;
the structural formula is as follows: si (CH) 3 ) 3 —O-(SiHCH 3 —O)n—Si(CH 3 ) 3 ,
Wherein n is 1-100 and H content is 0.1-1 wt%.
4. The one-part solventless addition type silicone tri-proof coating of claim 1, wherein the chain extender is one or more compositions of double-ended hydrosiloxanes;
the structural formula is as follows: H-Si (CH) 3 ) 2 —O-(Si(CH 3 ) 2 —O)n—Si(CH 3 ) 2 -H
Wherein n is 2-100 and H is 0.01-0.2 wt%.
5. The one-component solventless, addition-type silicone tri-proof coating of claim 1, wherein the toughening resin is a vinyl MQ silicone resin, wherein the vinyl MQ silicone resin has a vinyl content of 1% wt-20% wt.
6. The one-part solventless, addition-type silicone tri-proof coating of claim 1, wherein the inhibitor is one or more of 1-ethynyl cyclohexanol, 3-methyl-1-butyn-3-ol, 3-phenyl-1-butyn-3-ol, 3-propyl-1-butyn-3-ol, 3-octyl-1-butyn-3-ol.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202211319809.1A CN115627120B (en) | 2022-10-26 | 2022-10-26 | Single-component solvent-free addition type organosilicon three-proofing coating |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202211319809.1A CN115627120B (en) | 2022-10-26 | 2022-10-26 | Single-component solvent-free addition type organosilicon three-proofing coating |
Publications (2)
Publication Number | Publication Date |
---|---|
CN115627120A CN115627120A (en) | 2023-01-20 |
CN115627120B true CN115627120B (en) | 2023-06-16 |
Family
ID=84907065
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN202211319809.1A Active CN115627120B (en) | 2022-10-26 | 2022-10-26 | Single-component solvent-free addition type organosilicon three-proofing coating |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN115627120B (en) |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103210041A (en) * | 2010-11-10 | 2013-07-17 | 横滨橡胶株式会社 | Thermosetting silicone resin composition, and silicone resin-containing structure and optical semiconductor element encapsulant obtained using same |
CN104745142A (en) * | 2013-12-27 | 2015-07-01 | 蓝星有机硅(上海)有限公司 | Curable silicon rubber composition used for LED package |
CN106244093A (en) * | 2016-08-04 | 2016-12-21 | 深圳市安品有机硅材料有限公司 | Room temperature vulcanization addition type organic silicon pouring sealant composition |
CN110628326A (en) * | 2019-10-25 | 2019-12-31 | 广州玖盈化工材料有限公司 | Environment-friendly organic silicon three-proofing coating and preparation method thereof |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP5557438B2 (en) * | 2008-10-16 | 2014-07-23 | 日本カーバイド工業株式会社 | Adhesive composition and optical film |
JP6658428B2 (en) * | 2016-09-27 | 2020-03-04 | 信越化学工業株式会社 | Silicone gel composition, cured product thereof, and power module |
-
2022
- 2022-10-26 CN CN202211319809.1A patent/CN115627120B/en active Active
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103210041A (en) * | 2010-11-10 | 2013-07-17 | 横滨橡胶株式会社 | Thermosetting silicone resin composition, and silicone resin-containing structure and optical semiconductor element encapsulant obtained using same |
CN104745142A (en) * | 2013-12-27 | 2015-07-01 | 蓝星有机硅(上海)有限公司 | Curable silicon rubber composition used for LED package |
CN106244093A (en) * | 2016-08-04 | 2016-12-21 | 深圳市安品有机硅材料有限公司 | Room temperature vulcanization addition type organic silicon pouring sealant composition |
CN110628326A (en) * | 2019-10-25 | 2019-12-31 | 广州玖盈化工材料有限公司 | Environment-friendly organic silicon three-proofing coating and preparation method thereof |
Also Published As
Publication number | Publication date |
---|---|
CN115627120A (en) | 2023-01-20 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP4927856B2 (en) | Adhesive composition containing organosilane compound for adhesive for polarizing plate of liquid crystal display device | |
US5514730A (en) | Radiation-curable acrylate/silicone pressure-sensitive adhesive compositions | |
EP2954022B1 (en) | Clustered functional polyorganosiloxanes, processes for forming same and methods for their use | |
CN110643213A (en) | Light release regulator for silicon release agent and synthesis method and application thereof | |
CN110317558A (en) | A kind of poly-dopamine acrylic adhesive for polyurethane and preparation method thereof | |
JP2016121215A (en) | Isocyanate group-containing organopolysiloxane compound, method for producing the same, adhesive, tackiness agent, and coating agent | |
JPS63156805A (en) | Production of cold-setting resin | |
CN115627120B (en) | Single-component solvent-free addition type organosilicon three-proofing coating | |
TW201902988A (en) | Silicone-modified polyimide resin composition suitable for the use of primer that has excellent coatability | |
JP4298750B2 (en) | Novel silane coupling agent and method for producing the same | |
CN111187294B (en) | Unsaturated organosilicon compound containing epoxy group, heat-resistant high-toughness peelable adhesive, preparation method and application thereof | |
JPH0548269B2 (en) | ||
EP1937695B1 (en) | Novel organic silane compound | |
CN115521625B (en) | Low-temperature bonding boiling-resistant double-component addition type silicone rubber and preparation method thereof | |
CN115477723B (en) | Hyperbranched acrylic ester composition and photo-curing acrylic ester pressure-sensitive adhesive and preparation method thereof | |
WO2024176616A1 (en) | Fluorene skeleton-containing polymer | |
WO2024176617A1 (en) | Fluorene skeleton-containing (meth)acrylate compound, resin composition, and cured product | |
CN114085642B (en) | Preparation method of organic silicon pressure-sensitive adhesive | |
CN112358581B (en) | Functional assistant for liquid silicone rubber and preparation method and application thereof | |
JP2006193691A (en) | Photosensitive polyamic acid and photosensitive composition including the same | |
CN117186417B (en) | Low-climbing anti-aging anchoring agent, preparation method thereof and pressure-sensitive adhesive for protective film | |
KR101948942B1 (en) | Method of preparing silane compounds and acrylic adhesive composition | |
CN118755292B (en) | A UV/moisture dual-curing triple-proof adhesive and its preparation method and application | |
JP2005105246A (en) | Polysilsesquioxane graft polymer, process for producing the same, and pressure-sensitive adhesive | |
JPH01210461A (en) | Curable composition and its product of curing |
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 | ||
GR01 | Patent grant | ||
GR01 | Patent grant |