JP2006522206A - シロキサン重合性成分を含むアミン有機ボラン錯体開始重合性組成物 - Google Patents
シロキサン重合性成分を含むアミン有機ボラン錯体開始重合性組成物 Download PDFInfo
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- JP2006522206A JP2006522206A JP2006508864A JP2006508864A JP2006522206A JP 2006522206 A JP2006522206 A JP 2006522206A JP 2006508864 A JP2006508864 A JP 2006508864A JP 2006508864 A JP2006508864 A JP 2006508864A JP 2006522206 A JP2006522206 A JP 2006522206A
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- composition
- siloxane
- polymerizable
- oligomers
- compounds
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- 239000000203 mixture Substances 0.000 title claims abstract description 199
- 150000001412 amines Chemical class 0.000 title claims abstract description 95
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 title claims description 104
- -1 siloxane backbone Chemical group 0.000 claims abstract description 113
- 150000001875 compounds Chemical class 0.000 claims abstract description 103
- 229920000642 polymer Polymers 0.000 claims abstract description 66
- 239000003054 catalyst Substances 0.000 claims abstract description 61
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 43
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 33
- 239000000178 monomer Substances 0.000 claims abstract description 32
- 238000010526 radical polymerization reaction Methods 0.000 claims abstract description 20
- 239000007788 liquid Substances 0.000 claims abstract description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 10
- 239000003446 ligand Substances 0.000 claims abstract description 4
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- 239000000758 substrate Substances 0.000 claims description 78
- 239000001257 hydrogen Substances 0.000 claims description 61
- 229910052739 hydrogen Inorganic materials 0.000 claims description 61
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 claims description 28
- 150000002431 hydrogen Chemical class 0.000 claims description 26
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 22
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- 229910000085 borane Inorganic materials 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 18
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- 239000004925 Acrylic resin Substances 0.000 claims description 14
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 claims description 14
- 150000004678 hydrides Chemical group 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 238000009833 condensation Methods 0.000 claims description 10
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- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 8
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- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 230000000379 polymerizing effect Effects 0.000 claims description 6
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- 125000002877 alkyl aryl group Chemical group 0.000 claims description 5
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- 238000010494 dissociation reaction Methods 0.000 claims description 3
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- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims description 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 2
- 229910052796 boron Inorganic materials 0.000 claims description 2
- 239000002685 polymerization catalyst Substances 0.000 claims description 2
- 125000005373 siloxane group Chemical group [SiH2](O*)* 0.000 claims description 2
- 230000009257 reactivity Effects 0.000 abstract description 2
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- 238000006243 chemical reaction Methods 0.000 description 26
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- 238000012360 testing method Methods 0.000 description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
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- 239000004205 dimethyl polysiloxane Substances 0.000 description 16
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
- 239000003795 chemical substances by application Substances 0.000 description 15
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 15
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 14
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- 239000005058 Isophorone diisocyanate Substances 0.000 description 13
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 13
- 239000000654 additive Substances 0.000 description 12
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
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- 239000005020 polyethylene terephthalate Substances 0.000 description 12
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- CMHHITPYCHHOGT-UHFFFAOYSA-N tributylborane Chemical compound CCCCB(CCCC)CCCC CMHHITPYCHHOGT-UHFFFAOYSA-N 0.000 description 12
- 238000004987 plasma desorption mass spectroscopy Methods 0.000 description 11
- 150000003254 radicals Chemical class 0.000 description 11
- 229920000178 Acrylic resin Polymers 0.000 description 10
- 125000003277 amino group Chemical group 0.000 description 10
- CXQXSVUQTKDNFP-UHFFFAOYSA-N octamethyltrisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C CXQXSVUQTKDNFP-UHFFFAOYSA-N 0.000 description 10
- 229920000768 polyamine Polymers 0.000 description 10
- 150000003141 primary amines Chemical class 0.000 description 10
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- 238000002156 mixing Methods 0.000 description 9
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- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 239000012790 adhesive layer Substances 0.000 description 8
- 150000001336 alkenes Chemical class 0.000 description 8
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 8
- 239000003999 initiator Substances 0.000 description 8
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- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 8
- 229920001296 polysiloxane Polymers 0.000 description 8
- 239000004971 Cross linker Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 238000001723 curing Methods 0.000 description 7
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- 229920005989 resin Polymers 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 6
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- 150000001334 alicyclic compounds Chemical class 0.000 description 6
- 125000002947 alkylene group Chemical group 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- 150000007517 lewis acids Chemical class 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- 229920001155 polypropylene Polymers 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000004593 Epoxy Substances 0.000 description 5
- 239000004677 Nylon Substances 0.000 description 5
- 229920010524 Syndiotactic polystyrene Polymers 0.000 description 5
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 5
- 150000001409 amidines Chemical group 0.000 description 5
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- 239000003431 cross linking reagent Substances 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 125000000524 functional group Chemical group 0.000 description 5
- 229920001778 nylon Polymers 0.000 description 5
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 5
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- 239000000047 product Substances 0.000 description 5
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- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
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- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 4
- 125000004423 acyloxy group Chemical group 0.000 description 4
- 125000003302 alkenyloxy group Chemical group 0.000 description 4
- 125000003368 amide group Chemical group 0.000 description 4
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- 239000011324 bead Substances 0.000 description 4
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 description 4
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 4
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- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 4
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- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 3
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 3
- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 description 3
- ZHLSOSXEBSWGDW-UHFFFAOYSA-N 3-aminopropyl triethyl silicate Chemical compound CCO[Si](OCC)(OCC)OCCCN ZHLSOSXEBSWGDW-UHFFFAOYSA-N 0.000 description 3
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 3
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- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 3
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Classifications
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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
-
- 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
-
- 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
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of 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; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
-
- 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
- C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
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- 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
- C08G77/045—Polysiloxanes containing less than 25 silicon atoms
-
- 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
- C08G77/12—Polysiloxanes containing silicon bound to hydrogen
-
- 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
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
- C08G77/16—Polysiloxanes containing silicon bound to oxygen-containing groups to hydroxyl groups
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- 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
- C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic 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
- C08K5/00—Use of organic ingredients
- C08K5/55—Boron-containing compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Silicon Polymers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
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| PCT/US2004/005828 WO2004078871A1 (en) | 2003-02-28 | 2004-02-20 | Amine organoborane complex initiated polymerizable compositions containing siloxane polymerizable components |
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| JP2006522206A true JP2006522206A (ja) | 2006-09-28 |
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| JP (1) | JP2006522206A (enExample) |
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| CN (2) | CN1931904B (enExample) |
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| MX (1) | MXPA05009154A (enExample) |
| RU (1) | RU2335517C2 (enExample) |
| WO (1) | WO2004078871A1 (enExample) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008527105A (ja) * | 2005-01-04 | 2008-07-24 | ダウ・コーニング・コーポレイション | 有機硅素官能基硼素アミン触媒錯体およびこれから調製された硬化可能な組成物 |
| JP2008527077A (ja) * | 2005-01-04 | 2008-07-24 | ダウ・コーニング・コーポレイション | オルガノボランアミン錯体によって硬化されたシロキサンおよびシラン |
| JP2009538367A (ja) * | 2006-05-23 | 2009-11-05 | ダウ・コーニング・コーポレイション | アミド官能性ポリマーとのボラン触媒錯体、およびその錯体から作られる硬化性組成物 |
| JP2012530827A (ja) * | 2009-06-26 | 2012-12-06 | ビーエーエスエフ ソシエタス・ヨーロピア | ラジカル重合可能な化合物および有機ボラン−アミン錯体を含む被覆組成物の硬化方法 |
| JP2012530833A (ja) * | 2009-06-26 | 2012-12-06 | ビーエーエスエフ ソシエタス・ヨーロピア | 自動車部品上に硬化塗膜組成物を形成する方法 |
| JP2014500393A (ja) * | 2010-12-27 | 2014-01-09 | ダウ コーニング コーポレーション | 硬化性ケイ酸塩−シロキサン混合マトリックス膜組成物 |
| JP2017508852A (ja) * | 2014-03-25 | 2017-03-30 | ダウ コーニング コーポレーションＤｏｗ Ｃｏｒｎｉｎｇ Ｃｏｒｐｏｒａｔｉｏｎ | 改質されたエラストマー表面 |
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| JP2022535083A (ja) * | 2019-06-04 | 2022-08-04 | ダウ シリコーンズ コーポレーション | Ｓｉ－Ｈとアルファ－ベータ不飽和エステルとの反応のための熱トリガとしての架橋型フラストレイテッドルイスペア |
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| US6777512B1 (en) * | 2003-02-28 | 2004-08-17 | Dow Global Technologies Inc. | Amine organoborane complex initiated polymerizable compositions containing siloxane polymerizable components |
| EP1648944A1 (en) * | 2003-06-09 | 2006-04-26 | The Dow Global Technologies Inc. | Stabilized organoborane polymerization initiators and polymerizable compositions |
| CN1835992B (zh) * | 2003-08-13 | 2010-10-06 | 陶氏环球技术公司 | 使基材与物体接合的方法 |
| WO2005017005A1 (en) * | 2003-08-13 | 2005-02-24 | Dow Global Technologies Inc. | Method for joining substrates and objects |
| GB0326286D0 (en) | 2003-11-11 | 2003-12-17 | Vantico Gmbh | Initiator systems for polymerisable compositions |
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| US8501886B2 (en) * | 2003-12-22 | 2013-08-06 | Dow Global Technologies Llc | Accelerated organoborane amine complex initiated polymerizable compositions |
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| JP2012530827A (ja) * | 2009-06-26 | 2012-12-06 | ビーエーエスエフ ソシエタス・ヨーロピア | ラジカル重合可能な化合物および有機ボラン−アミン錯体を含む被覆組成物の硬化方法 |
| JP2012530833A (ja) * | 2009-06-26 | 2012-12-06 | ビーエーエスエフ ソシエタス・ヨーロピア | 自動車部品上に硬化塗膜組成物を形成する方法 |
| JP2014500393A (ja) * | 2010-12-27 | 2014-01-09 | ダウ コーニング コーポレーション | 硬化性ケイ酸塩−シロキサン混合マトリックス膜組成物 |
| JP2017508852A (ja) * | 2014-03-25 | 2017-03-30 | ダウ コーニング コーポレーションＤｏｗ Ｃｏｒｎｉｎｇ Ｃｏｒｐｏｒａｔｉｏｎ | 改質されたエラストマー表面 |
| JP2018502939A (ja) * | 2014-11-14 | 2018-02-01 | スリーエム イノベイティブ プロパティズ カンパニー | ２液型接着剤組成物及び接着剤組成物の製造方法 |
| US10221337B2 (en) | 2014-11-14 | 2019-03-05 | 3M Innovative Properties Company | Two-part adhesive composition and method of making an adhesive composition |
| JP2019527268A (ja) * | 2016-09-09 | 2019-09-26 | エルジー・ケム・リミテッド | フォルダブルディスプレイ用粘着剤組成物 |
| JP2022535083A (ja) * | 2019-06-04 | 2022-08-04 | ダウ シリコーンズ コーポレーション | Ｓｉ－Ｈとアルファ－ベータ不飽和エステルとの反応のための熱トリガとしての架橋型フラストレイテッドルイスペア |
| JP7560489B2 (ja) | 2019-06-04 | 2024-10-02 | ダウ シリコーンズ コーポレーション | Ｓｉ－Ｈとアルファ－ベータ不飽和エステルとの反応のための熱トリガとしての架橋型フラストレイテッドルイスペア |
Also Published As
| Publication number | Publication date |
|---|---|
| ATE535585T1 (de) | 2011-12-15 |
| WO2004078871A1 (en) | 2004-09-16 |
| RU2005130177A (ru) | 2006-03-20 |
| CN1931904B (zh) | 2011-04-06 |
| US20040210015A1 (en) | 2004-10-21 |
| CN1931904A (zh) | 2007-03-21 |
| CN1756821A (zh) | 2006-04-05 |
| CA2517364A1 (en) | 2004-09-16 |
| US20040242812A1 (en) | 2004-12-02 |
| MXPA05009154A (es) | 2005-10-20 |
| US6825298B2 (en) | 2004-11-30 |
| RU2335517C2 (ru) | 2008-10-10 |
| US6949603B2 (en) | 2005-09-27 |
| EP1599559B1 (en) | 2011-11-30 |
| US20040220363A1 (en) | 2004-11-04 |
| EP1599559A1 (en) | 2005-11-30 |
| BRPI0407666A (pt) | 2006-03-01 |
| US6777512B1 (en) | 2004-08-17 |
| KR20050107466A (ko) | 2005-11-11 |
| US7157399B2 (en) | 2007-01-02 |
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