JP2001502689A - オルガノボランアミン錯体開始剤系とそれによって作製された重合性組成物 - Google Patents
オルガノボランアミン錯体開始剤系とそれによって作製された重合性組成物Info
- Publication number
- JP2001502689A JP2001502689A JP10519319A JP51931998A JP2001502689A JP 2001502689 A JP2001502689 A JP 2001502689A JP 10519319 A JP10519319 A JP 10519319A JP 51931998 A JP51931998 A JP 51931998A JP 2001502689 A JP2001502689 A JP 2001502689A
- Authority
- JP
- Japan
- Prior art keywords
- aziridine
- amine
- complex
- group
- polyamine
- 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.)
- Ceased
Links
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- 239000003999 initiator Substances 0.000 title description 8
- 239000000178 monomer Substances 0.000 claims abstract description 81
- 150000001412 amines Chemical class 0.000 claims abstract description 75
- 239000000463 material Substances 0.000 claims abstract description 60
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- 150000001875 compounds Chemical class 0.000 claims abstract description 58
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims abstract description 35
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 27
- 239000003505 polymerization initiator Substances 0.000 claims abstract description 16
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- 229920000768 polyamine Polymers 0.000 claims description 36
- 239000000758 substrate Substances 0.000 claims description 33
- 125000004432 carbon atom Chemical group C* 0.000 claims description 28
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 27
- 229920002873 Polyethylenimine Polymers 0.000 claims description 24
- 239000002253 acid Substances 0.000 claims description 19
- 125000004069 aziridinyl group Chemical group 0.000 claims description 17
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- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 14
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- DVDMSISHJUNIAQ-UHFFFAOYSA-N 1,2,2-trimethylaziridine Chemical compound CN1CC1(C)C DVDMSISHJUNIAQ-UHFFFAOYSA-N 0.000 claims description 10
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 claims description 10
- 239000007788 liquid Substances 0.000 claims description 10
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- 150000002734 metacrylic acid derivatives Chemical class 0.000 claims description 8
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- 239000004810 polytetrafluoroethylene Substances 0.000 claims description 8
- 150000001299 aldehydes Chemical class 0.000 claims description 7
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
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- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 3
- 239000000376 reactant Substances 0.000 claims description 2
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- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 claims 8
- 239000002131 composite material Substances 0.000 claims 8
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- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 22
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- 125000003118 aryl group Chemical group 0.000 description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 11
- 238000012360 testing method Methods 0.000 description 11
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 10
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 10
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 8
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
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- 229910052782 aluminium Inorganic materials 0.000 description 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 7
- 125000004386 diacrylate group Chemical group 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 6
- 239000003292 glue Substances 0.000 description 6
- 150000002431 hydrogen Chemical class 0.000 description 6
- 238000011065 in-situ storage Methods 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 5
- 125000002877 alkyl aryl group Chemical group 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- 230000001588 bifunctional effect Effects 0.000 description 5
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- 229920001971 elastomer Polymers 0.000 description 5
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
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- 238000003860 storage Methods 0.000 description 5
- 238000004381 surface treatment Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- XFCMNSHQOZQILR-UHFFFAOYSA-N 2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOC(=O)C(C)=C XFCMNSHQOZQILR-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- 230000002411 adverse Effects 0.000 description 4
- 150000001541 aziridines Chemical class 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
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- 150000004985 diamines Chemical class 0.000 description 4
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- 238000002360 preparation method Methods 0.000 description 4
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- 238000007142 ring opening reaction Methods 0.000 description 4
- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical compound CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 description 4
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- NVGBPTNZLWRQSY-UWVGGRQHSA-N Lys-Lys Chemical compound NCCCC[C@H](N)C(=O)N[C@H](C(O)=O)CCCCN NVGBPTNZLWRQSY-UWVGGRQHSA-N 0.000 description 3
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- KAPCRJOPWXUMSQ-UHFFFAOYSA-N [2,2-bis[3-(aziridin-1-yl)propanoyloxymethyl]-3-hydroxypropyl] 3-(aziridin-1-yl)propanoate Chemical compound C1CN1CCC(=O)OCC(COC(=O)CCN1CC1)(CO)COC(=O)CCN1CC1 KAPCRJOPWXUMSQ-UHFFFAOYSA-N 0.000 description 3
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- 108010054155 lysyllysine Proteins 0.000 description 3
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
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- JWHOQZUREKYPBY-UHFFFAOYSA-N rubonic acid Natural products CC1(C)CCC2(CCC3(C)C(=CCC4C5(C)CCC(=O)C(C)(C)C5CC(=O)C34C)C2C1)C(=O)O JWHOQZUREKYPBY-UHFFFAOYSA-N 0.000 description 1
- 238000009938 salting Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 150000003335 secondary amines Chemical group 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 238000000992 sputter etching Methods 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-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
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical compound FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- IUCJMVBFZDHPDX-UHFFFAOYSA-N tretamine Chemical compound C1CN1C1=NC(N2CC2)=NC(N2CC2)=N1 IUCJMVBFZDHPDX-UHFFFAOYSA-N 0.000 description 1
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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
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/52—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides selected from boron, aluminium, gallium, indium, thallium or rare earths
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/28—Web or sheet containing structurally defined element or component and having an adhesive outermost layer
- Y10T428/2852—Adhesive compositions
- Y10T428/2878—Adhesive compositions including addition polymer from unsaturated monomer
- Y10T428/2891—Adhesive compositions including addition polymer from unsaturated monomer including addition polymer from alpha-beta unsaturated carboxylic acid [e.g., acrylic acid, methacrylic acid, etc.] Or derivative thereof
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/3154—Of fluorinated addition polymer from unsaturated monomers
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/3154—Of fluorinated addition polymer from unsaturated monomers
- Y10T428/31544—Addition polymer is perhalogenated
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31855—Of addition polymer from unsaturated monomers
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31855—Of addition polymer from unsaturated monomers
- Y10T428/31909—Next to second addition polymer from unsaturated monomers
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31855—Of addition polymer from unsaturated monomers
- Y10T428/31909—Next to second addition polymer from unsaturated monomers
- Y10T428/31913—Monoolefin polymer
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31855—Of addition polymer from unsaturated monomers
- Y10T428/31909—Next to second addition polymer from unsaturated monomers
- Y10T428/31928—Ester, halide or nitrile of addition polymer
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31855—Of addition polymer from unsaturated monomers
- Y10T428/31935—Ester, halide or nitrile of addition polymer
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Laminated Bodies (AREA)
- Polymerization Catalysts (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/735,765 US5935711A (en) | 1996-10-23 | 1996-10-23 | Organoborane amine complex initiator systems and polymerizable compositions made therewith |
| US08/735,765 | 1996-10-23 | ||
| PCT/US1997/002766 WO1998017694A1 (en) | 1996-10-23 | 1997-02-25 | Organoborane amine complex initiator systems and polymerizable compositions made therewith |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2001502689A true JP2001502689A (ja) | 2001-02-27 |
| JP2001502689A5 JP2001502689A5 (enExample) | 2004-11-25 |
Family
ID=24957092
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10519319A Ceased JP2001502689A (ja) | 1996-10-23 | 1997-02-25 | オルガノボランアミン錯体開始剤系とそれによって作製された重合性組成物 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US5935711A (enExample) |
| EP (1) | EP0934344B1 (enExample) |
| JP (1) | JP2001502689A (enExample) |
| CN (1) | CN1264867C (enExample) |
| AU (1) | AU1968497A (enExample) |
| BR (1) | BR9712554A (enExample) |
| DE (1) | DE69716630T2 (enExample) |
| WO (1) | WO1998017694A1 (enExample) |
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| JP2002540228A (ja) * | 1999-03-19 | 2002-11-26 | スリーエム イノベイティブ プロパティズ カンパニー | オルガノボランアミン錯体開始剤システムおよびこれを用いて製造される重合性組成物 |
| JP2007510788A (ja) * | 2003-11-11 | 2007-04-26 | ハンツマン・アドヴァンスト・マテリアルズ・(スイッツランド)・ゲーエムベーハー | 重合可能な組成物のための開始剤系 |
| JP2008502742A (ja) * | 2004-06-09 | 2008-01-31 | ダウ グローバル テクノロジーズ インコーポレイティド | 安定化有機ボラン重合開始剤及び重合性組成物 |
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| KR20200027997A (ko) * | 2017-07-12 | 2020-03-13 | 아르끄마 프랑스 | (메트)아크릴 접착제 조성물, 이의 제조 방법 및 이의 용도 |
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Family Cites Families (59)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA664459A (en) * | 1963-06-04 | Jennes Gert | Process for the polymerisation of unsaturated compounds | |
| US2985633A (en) * | 1958-10-30 | 1961-05-23 | Union Carbide Corp | Polymerization of ethylene with organoboron compounds treated with oxygen |
| US3340193A (en) * | 1960-12-30 | 1967-09-05 | Monsanto Co | Mineral oil containing alkyl polymethacrylate antifoamant |
| US3275611A (en) * | 1960-12-30 | 1966-09-27 | Monsanto Co | Process for polymerizing unsaturated monomers with a catalyst comprising an organoboron compound, a peroxygen compound and an amine |
| US3141862A (en) * | 1961-03-01 | 1964-07-21 | Exxon Research Engineering Co | Graft copolymerization using boron alkyls in the presence of oxygen as catalysts |
| BE602558A (enExample) * | 1961-03-14 | |||
| US3257360A (en) * | 1961-07-27 | 1966-06-21 | Monsanto Co | Terpolymers and processes for making same |
| US3306809A (en) * | 1961-08-21 | 1967-02-28 | Union Carbide Corp | Curable polyepoxide and glycol polyamine compositions |
| GB1113723A (en) * | 1964-05-21 | 1968-05-15 | Minnesota Mining & Mfg | Dental filling material |
| BE674405A (enExample) * | 1965-01-06 | 1966-06-28 | ||
| US3425988A (en) * | 1965-01-27 | 1969-02-04 | Loctite Corp | Polyurethane polyacrylate sealant compositions |
| JPS4214318Y1 (enExample) * | 1965-02-26 | 1967-08-15 | ||
| BE524840A (enExample) * | 1965-12-17 | |||
| US3418260A (en) * | 1966-01-20 | 1968-12-24 | Du Pont | Imidazole-borane polymers |
| JPS4529195Y1 (enExample) * | 1967-04-13 | 1970-11-10 | ||
| US3527737A (en) * | 1967-09-15 | 1970-09-08 | G C Kagaku Kogyo Kk | Adhesive compositions |
| JPS4616888Y1 (enExample) * | 1968-02-15 | 1971-06-12 | ||
| JPS4818928B1 (enExample) * | 1969-12-13 | 1973-06-09 | ||
| JPS5137092B2 (enExample) * | 1972-04-28 | 1976-10-13 | ||
| JPS53102394A (en) * | 1977-02-18 | 1978-09-06 | Hitachi Ltd | Two-pack type resin composition |
| US4167616A (en) * | 1977-08-22 | 1979-09-11 | Rohm And Haas Company | Polymerization with diborane adducts or oligomers of boron-containing monomers |
| DE3041904C2 (de) * | 1980-11-06 | 1984-11-22 | Henkel KGaA, 4000 Düsseldorf | Borverbindungen enthaltende lagerstabile Reaktionsklebstoffe |
| DE3207263A1 (de) * | 1982-03-01 | 1983-09-08 | Henkel KGaA, 4000 Düsseldorf | Organo-borverbindungen enthaltende stoffgemische, verfahren zu ihrer herstellung und ihre verwendung |
| DE3201780A1 (de) * | 1982-01-21 | 1983-08-25 | Henkel KGaA, 4000 Düsseldorf | Neue polymere organo-borverbindungen und ihre verwendung |
| DE3201731A1 (de) * | 1982-01-21 | 1983-07-28 | Henkel KGaA, 4000 Düsseldorf | "aerob haertende kunststoffmassen" |
| US4379728A (en) * | 1982-02-04 | 1983-04-12 | W. R. Grace & Co. | Cyanourea compounds or polymers thereof as epoxy resin curing agents |
| DE3207264A1 (de) * | 1982-03-01 | 1983-09-08 | Henkel KGaA, 4000 Düsseldorf | Neue boralkylverbindungen, verfahren zu ihrer herstellung und ihre verwendung |
| US4524181A (en) * | 1983-08-11 | 1985-06-18 | Minnesota Mining And Manufacturing Company | Curable epoxy compositions and cured resins obtained therefrom |
| US4485229A (en) * | 1984-02-15 | 1984-11-27 | Texaco Inc. | Epoxy resin containing a combination of high and low molecular weight polyoxyalkylene polyamine curing agents |
| US4731416A (en) * | 1984-10-01 | 1988-03-15 | The Dow Chemical Company | Polyurethane-type adhesives containing nonaqueous solutions of acrylate polymers |
| DE3518965A1 (de) * | 1985-05-25 | 1986-11-27 | Henkel KGaA, 40589 Düsseldorf | Schmelzbare und dabei aerob aushaertende kunststoffmassen und verfahren zu ihrer herstellung |
| US4874814A (en) * | 1985-07-02 | 1989-10-17 | Monsanto Company | Cross-linked polyvinyl butyral |
| US4656229A (en) * | 1985-12-02 | 1987-04-07 | National Starch And Chemical Corporation | Anaerobic adhesive compositions |
| US4684538A (en) * | 1986-02-21 | 1987-08-04 | Loctite Corporation | Polysiloxane urethane compounds and adhesive compositions, and method of making and using the same |
| US5021507A (en) * | 1986-05-05 | 1991-06-04 | National Starch And Chemical Investment Holding Corporation | Arcylic modified reactive urethane hot melt adhesive compositions |
| JP2528098B2 (ja) * | 1986-06-06 | 1996-08-28 | 三井石油化学工業株式会社 | セラミックス用接着剤 |
| US4904360A (en) * | 1986-09-12 | 1990-02-27 | Minnesota Mining And Manufacturing Company | Water-compatible coating composition |
| CA1292591C (en) * | 1986-10-30 | 1991-11-26 | Takeshi Sakashita | Curable composition |
| US4721751A (en) * | 1987-03-26 | 1988-01-26 | Ppg Industries, Inc. | Polyurea-polyurethane acrylate dispersions |
| JPH075680B2 (ja) * | 1987-07-03 | 1995-01-25 | 三井石油化学工業株式会社 | 硬化性組成物 |
| US4775734A (en) * | 1987-08-12 | 1988-10-04 | Ashland Oil, Inc. | Non-nucleophilic acid salts of amines as cure accelerators |
| JP2719582B2 (ja) * | 1989-08-14 | 1998-02-25 | 三井石油化学工業株式会社 | 塗料用樹脂組成物 |
| JP2811839B2 (ja) * | 1989-12-06 | 1998-10-15 | 三井化学株式会社 | 歯科用チタンまたはその合金用硬化性接着剤組成物 |
| JPH03229777A (ja) * | 1990-02-02 | 1991-10-11 | Toyo Ink Mfg Co Ltd | 嫌気硬化性粘着剤組成物 |
| JP2812527B2 (ja) * | 1990-03-15 | 1998-10-22 | 三井化学株式会社 | 歯科接着剤用触媒ペースト状組成物 |
| US5143884A (en) * | 1991-04-29 | 1992-09-01 | National Starch And Chemical Investment Holding Corporation | Acrylic adhesive composition and organoboron initiator system |
| US5106928A (en) * | 1991-04-29 | 1992-04-21 | National Starch And Chemical Investment Holding Corporation | Acrylic adhesive composition and organoboron initiator system |
| JPH05235089A (ja) * | 1992-02-26 | 1993-09-10 | Fujitsu Ltd | フェイスダウン実装用半導体チップ |
| US5286821A (en) * | 1992-03-17 | 1994-02-15 | National Starch And Chemical Investment Holding Corporation | Acrylic adhesive composition and organoboron initiator system |
| US5401805A (en) * | 1992-04-06 | 1995-03-28 | The Penn State Research Foundation | Olefin graft copolymers prepared using borane-containing olefin backbone polymers |
| US5310835A (en) * | 1993-09-30 | 1994-05-10 | National Starch And Chemical Investment Holding Corporation | Transparent two-part acrylic adhesive composition and the method of use thereof |
| JPH07138542A (ja) * | 1993-11-17 | 1995-05-30 | Sekisui Chem Co Ltd | 建築内装材固定用両面粘着テープ |
| JPH07138544A (ja) * | 1993-11-18 | 1995-05-30 | Sekisui Chem Co Ltd | アクリル系感圧性接着剤組成物 |
| BR9408536A (pt) * | 1994-02-22 | 1997-08-05 | Minnesota Mining & Mfg | Composição acrílica polimerizável compósito ligado processo para ligar entre si adesivamente dois substratos e para melhorar a adesão de um adesivo subsequentemente aplicado em um substrato de fluoroplástico |
| JPH08134408A (ja) * | 1994-11-09 | 1996-05-28 | Sekisui Chem Co Ltd | アクリル系粘着テープ |
| US5616796A (en) * | 1995-04-14 | 1997-04-01 | Minnesota Mining And Manufacturing Company | Organoborane polyamine complexes and adhesive composition made therewith |
| US5621143A (en) * | 1995-04-14 | 1997-04-15 | Minnesota Mining And Manufacturing Company | Organoborane polyoxyalkylenepolyamine complexes and adhesive compositions made therewith |
| US5686544A (en) * | 1995-08-11 | 1997-11-11 | Minnesota Mining And Manufacturing Company | Organoborane polyamine complex initiator systems and polymerizable compositions made therewith |
| US5712331A (en) * | 1995-08-15 | 1998-01-27 | Rockwell International Corporation | Curable epoxy compositions containing aziridine in supercritical fluid carbon dioxide |
-
1996
- 1996-10-23 US US08/735,765 patent/US5935711A/en not_active Expired - Lifetime
-
1997
- 1997-02-25 AU AU19684/97A patent/AU1968497A/en not_active Abandoned
- 1997-02-25 DE DE69716630T patent/DE69716630T2/de not_active Expired - Lifetime
- 1997-02-25 CN CN97198945.1A patent/CN1264867C/zh not_active Expired - Fee Related
- 1997-02-25 BR BR9712554-7A patent/BR9712554A/pt not_active IP Right Cessation
- 1997-02-25 WO PCT/US1997/002766 patent/WO1998017694A1/en not_active Ceased
- 1997-02-25 EP EP97907773A patent/EP0934344B1/en not_active Expired - Lifetime
- 1997-02-25 JP JP10519319A patent/JP2001502689A/ja not_active Ceased
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002540228A (ja) * | 1999-03-19 | 2002-11-26 | スリーエム イノベイティブ プロパティズ カンパニー | オルガノボランアミン錯体開始剤システムおよびこれを用いて製造される重合性組成物 |
| JP2007510788A (ja) * | 2003-11-11 | 2007-04-26 | ハンツマン・アドヴァンスト・マテリアルズ・(スイッツランド)・ゲーエムベーハー | 重合可能な組成物のための開始剤系 |
| JP2008502742A (ja) * | 2004-06-09 | 2008-01-31 | ダウ グローバル テクノロジーズ インコーポレイティド | 安定化有機ボラン重合開始剤及び重合性組成物 |
| JP2016525581A (ja) * | 2013-06-28 | 2016-08-25 | スリーエム イノベイティブ プロパティズ カンパニー | 酸改質ナノ粒子、二部分型重合性組成物、及び方法 |
| WO2017138567A1 (ja) * | 2016-02-09 | 2017-08-17 | サンメディカル株式会社 | 重合性組成物およびキット、ならびに重合開始剤 |
| US11130864B2 (en) | 2016-02-09 | 2021-09-28 | Sun Medical Co., Ltd. | Polymerizable composition and kit, and polymerization initiator |
| KR20200027997A (ko) * | 2017-07-12 | 2020-03-13 | 아르끄마 프랑스 | (메트)아크릴 접착제 조성물, 이의 제조 방법 및 이의 용도 |
| JP2020527621A (ja) * | 2017-07-12 | 2020-09-10 | アルケマ フランス | (メタ)アクリル接着剤組成物、その調製方法及びその使用 |
| KR102543292B1 (ko) * | 2017-07-12 | 2023-06-13 | 아르끄마 프랑스 | (메트)아크릴 접착제 조성물, 이의 제조 방법 및 이의 용도 |
| JP7463269B2 (ja) | 2017-07-12 | 2024-04-08 | アルケマ フランス | (メタ)アクリル接着剤組成物、その調製方法及びその使用 |
Also Published As
| Publication number | Publication date |
|---|---|
| BR9712554A (pt) | 1999-10-19 |
| DE69716630D1 (de) | 2002-11-28 |
| WO1998017694A1 (en) | 1998-04-30 |
| DE69716630T2 (de) | 2003-07-03 |
| CN1234041A (zh) | 1999-11-03 |
| AU1968497A (en) | 1998-05-15 |
| CN1264867C (zh) | 2006-07-19 |
| EP0934344B1 (en) | 2002-10-23 |
| EP0934344A1 (en) | 1999-08-11 |
| HK1022156A1 (en) | 2000-07-28 |
| US5935711A (en) | 1999-08-10 |
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