DE69821265T2 - Geruchsarme polymerisierbare zusammensetzungen zum binden von substraten mit niedriger oberflächenenergie - Google Patents
Geruchsarme polymerisierbare zusammensetzungen zum binden von substraten mit niedriger oberflächenenergie Download PDFInfo
- Publication number
- DE69821265T2 DE69821265T2 DE69821265T DE69821265T DE69821265T2 DE 69821265 T2 DE69821265 T2 DE 69821265T2 DE 69821265 T DE69821265 T DE 69821265T DE 69821265 T DE69821265 T DE 69821265T DE 69821265 T2 DE69821265 T2 DE 69821265T2
- Authority
- DE
- Germany
- Prior art keywords
- methacrylate
- kit according
- monomer
- surface energy
- acrylate
- 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.)
- Expired - Lifetime
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- 239000000758 substrate Substances 0.000 title claims description 62
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- 238000009739 binding Methods 0.000 title claims description 44
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- 239000003999 initiator Substances 0.000 claims description 61
- 229920000642 polymer Polymers 0.000 claims description 24
- 238000009835 boiling Methods 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 18
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- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 claims description 12
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 claims description 9
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 claims description 9
- NUXLDNTZFXDNBA-UHFFFAOYSA-N 6-bromo-2-methyl-4h-1,4-benzoxazin-3-one Chemical compound C1=C(Br)C=C2NC(=O)C(C)OC2=C1 NUXLDNTZFXDNBA-UHFFFAOYSA-N 0.000 claims description 9
- DXPPIEDUBFUSEZ-UHFFFAOYSA-N 6-methylheptyl prop-2-enoate Chemical compound CC(C)CCCCCOC(=O)C=C DXPPIEDUBFUSEZ-UHFFFAOYSA-N 0.000 claims description 9
- COCLLEMEIJQBAG-UHFFFAOYSA-N 8-methylnonyl 2-methylprop-2-enoate Chemical compound CC(C)CCCCCCCOC(=O)C(C)=C COCLLEMEIJQBAG-UHFFFAOYSA-N 0.000 claims description 9
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 9
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- IAXXETNIOYFMLW-COPLHBTASA-N [(1s,3s,4s)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl] 2-methylprop-2-enoate Chemical compound C1C[C@]2(C)[C@@H](OC(=O)C(=C)C)C[C@H]1C2(C)C IAXXETNIOYFMLW-COPLHBTASA-N 0.000 claims description 9
- 229940119545 isobornyl methacrylate Drugs 0.000 claims description 9
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 7
- OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 0.000 claims description 7
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 claims description 6
- LNCPIMCVTKXXOY-UHFFFAOYSA-N hexyl 2-methylprop-2-enoate Chemical compound CCCCCCOC(=O)C(C)=C LNCPIMCVTKXXOY-UHFFFAOYSA-N 0.000 claims description 6
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- RUMACXVDVNRZJZ-UHFFFAOYSA-N 2-methylpropyl 2-methylprop-2-enoate Chemical compound CC(C)COC(=O)C(C)=C RUMACXVDVNRZJZ-UHFFFAOYSA-N 0.000 claims description 3
- 238000000576 coating method Methods 0.000 claims description 3
- KBLWLMPSVYBVDK-UHFFFAOYSA-N cyclohexyl prop-2-enoate Chemical compound C=CC(=O)OC1CCCCC1 KBLWLMPSVYBVDK-UHFFFAOYSA-N 0.000 claims description 3
- LNMQRPPRQDGUDR-UHFFFAOYSA-N hexyl prop-2-enoate Chemical compound CCCCCCOC(=O)C=C LNMQRPPRQDGUDR-UHFFFAOYSA-N 0.000 claims description 3
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- ROZDMUUELHCVQC-ARJAWSKDSA-N (z)-4-oxo-4-(2-prop-2-enoyloxyethoxy)but-2-enoic acid Chemical compound OC(=O)\C=C/C(=O)OCCOC(=O)C=C ROZDMUUELHCVQC-ARJAWSKDSA-N 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 3
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- ZPCKHGXAHBBJJH-UHFFFAOYSA-N hexane-1,6-diamine;triethylborane Chemical compound CCB(CC)CC.NCCCCCCN ZPCKHGXAHBBJJH-UHFFFAOYSA-N 0.000 description 3
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
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- RUEKTOVLVIXOHT-UHFFFAOYSA-N 2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluorooctyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F RUEKTOVLVIXOHT-UHFFFAOYSA-N 0.000 description 2
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- 150000003623 transition metal compounds Chemical class 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- YUPAWYWJNZDARM-UHFFFAOYSA-N tri(butan-2-yl)borane Chemical compound CCC(C)B(C(C)CC)C(C)CC YUPAWYWJNZDARM-UHFFFAOYSA-N 0.000 description 1
- ZTKBVWUYLHTIBB-UHFFFAOYSA-N tri(propan-2-yl)borane Chemical compound CC(C)B(C(C)C)C(C)C ZTKBVWUYLHTIBB-UHFFFAOYSA-N 0.000 description 1
- CMHHITPYCHHOGT-UHFFFAOYSA-N tributylborane Chemical compound CCCCB(CCCC)CCCC CMHHITPYCHHOGT-UHFFFAOYSA-N 0.000 description 1
- WXRGABKACDFXMG-UHFFFAOYSA-N trimethylborane Chemical compound CB(C)C WXRGABKACDFXMG-UHFFFAOYSA-N 0.000 description 1
- ZMPKTELQGVLZTD-UHFFFAOYSA-N tripropylborane Chemical compound CCCB(CCC)CCC ZMPKTELQGVLZTD-UHFFFAOYSA-N 0.000 description 1
- XDSSGQHOYWGIKC-UHFFFAOYSA-N tris(2-methylpropyl)borane Chemical compound CC(C)CB(CC(C)C)CC(C)C XDSSGQHOYWGIKC-UHFFFAOYSA-N 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
- C08F220/281—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing only one oxygen, e.g. furfuryl (meth)acrylate or 2-methoxyethyl (meth)acrylate
-
- 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
- C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/04—Homopolymers or copolymers of esters
- C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09J133/062—Copolymers with monomers not covered by C09J133/06
-
- 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
- C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/04—Homopolymers or copolymers of esters
- C09J133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
-
- 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
-
- 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
- C09J5/00—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers
-
- 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
- C09J7/00—Adhesives in the form of films or foils
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Polymerization Catalysts (AREA)
- Paints Or Removers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/US1998/012260 WO1999064528A1 (en) | 1998-06-12 | 1998-06-12 | Low odor polymerizable compositions useful for bonding low surface energy substrates |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69821265D1 DE69821265D1 (de) | 2004-02-26 |
| DE69821265T2 true DE69821265T2 (de) | 2004-11-04 |
Family
ID=22267304
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69821265T Expired - Lifetime DE69821265T2 (de) | 1998-06-12 | 1998-06-12 | Geruchsarme polymerisierbare zusammensetzungen zum binden von substraten mit niedriger oberflächenenergie |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP1098943B1 (enExample) |
| JP (1) | JP4373007B2 (enExample) |
| KR (1) | KR100629832B1 (enExample) |
| CN (1) | CN1216955C (enExample) |
| AU (1) | AU7838298A (enExample) |
| BR (1) | BR9815905A (enExample) |
| DE (1) | DE69821265T2 (enExample) |
| WO (1) | WO1999064528A1 (enExample) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6383655B1 (en) | 1998-06-12 | 2002-05-07 | 3M Innovative Properties Company | Low odor polymerizable compositions useful for bonding low surface energy substrates |
| US6812308B2 (en) | 2000-11-21 | 2004-11-02 | 3M Innovative Properties Company | Initiator systems and adhesive compositions made therewith |
| US6252023B1 (en) | 1999-03-19 | 2001-06-26 | 3M Innovative Properties Company | Organoborane amine complex inatator systems and polymerizable compositions made therewith |
| US6486090B1 (en) | 1999-11-04 | 2002-11-26 | 3M Innovative Properties Company | Initiator/hydroxide and initiator/alkoxide complexes, systems comprising the complexes, and polymerized compositions made therewith |
| US6410667B1 (en) | 1999-11-04 | 2002-06-25 | 3M Innovative Properties Company | Initiator/amidine complexes, systems comprising the complexes, and polymerized compositions made therewith |
| US6479602B1 (en) * | 2000-03-15 | 2002-11-12 | 3M Innovative Properties | Polymerization initiator systems and bonding compositions comprising vinyl aromatic compounds |
| EP1201722A1 (en) | 2000-10-23 | 2002-05-02 | Loctite (R & D) Limited | Polymerisation initiators, polymerisable compositions, and uses thereof |
| IE20020293A1 (en) | 2002-04-23 | 2003-10-29 | Loctite R & D Ltd | Initiator systems, polymerisable compositions, and uses thereof for bonding low surface energy substrates |
| US6740716B2 (en) * | 2001-10-30 | 2004-05-25 | Dow Global Technologies Inc. | Organoborane amine complex polymerization initiators and polymerizable compositions |
| US6632908B1 (en) | 2002-03-12 | 2003-10-14 | Henkel Loctite Corporation | Bonding system having adherence to low energy surfaces |
| WO2003089536A2 (en) | 2002-04-19 | 2003-10-30 | Loctite (R & D) Limited | Polymerisation initiators based on ammonium tetraalkyl boranes, polymerisable compositions, and uses thereof for bonding low surface energy substrates |
| US6867271B1 (en) | 2002-06-24 | 2005-03-15 | Henkel Corporation | Non-flammable and non-combustible adhesive bonding systems having adherence to low energy surfaces |
| US7098279B2 (en) | 2002-10-22 | 2006-08-29 | Loctite (R&D) Limited | Non-flammable and non-combustible adhesive bonding systems having adherence to low energy surfaces |
| GB0326286D0 (en) | 2003-11-11 | 2003-12-17 | Vantico Gmbh | Initiator systems for polymerisable compositions |
| US8202932B2 (en) | 2004-12-03 | 2012-06-19 | Loctite (R&D) Limited | Adhesive bonding systems having adherence to low energy surfaces |
| US7408012B1 (en) | 2005-04-18 | 2008-08-05 | Loctite (R&D) Limited | Adhesive bonding systems having adherence to low energy surfaces |
| KR101665534B1 (ko) * | 2008-07-28 | 2016-10-13 | 다우 코닝 코포레이션 | 복합 물품 |
| JP6297857B2 (ja) * | 2014-02-21 | 2018-03-20 | スリーエム イノベイティブ プロパティズ カンパニー | ２液型接着剤及びそれを含む構造体 |
| JP6849303B2 (ja) * | 2015-08-12 | 2021-03-24 | スリーエム イノベイティブ プロパティズ カンパニー | ２液型接着剤及びその硬化物を含む構造体 |
| KR102526801B1 (ko) * | 2016-03-11 | 2023-05-02 | 이노텍 모션 게엠베하 | 시트 새시에 고정하기 위한 발판 새시 |
| WO2018098302A1 (en) | 2016-11-22 | 2018-05-31 | Valspar Sourcing, Inc. | Low odor water-based coating composition |
| JP7045329B2 (ja) * | 2016-12-16 | 2022-03-31 | デンカ株式会社 | 組成物 |
| US12258495B2 (en) | 2018-12-28 | 2025-03-25 | Saint-Gobain Performance Plastics Corporation | Adhesive composition and methods of forming the same |
| CN110358455A (zh) * | 2019-08-01 | 2019-10-22 | 烟台艾格路电子科技有限公司 | 一种低气味快速固化的丙烯酸胶黏剂 |
| CN111253905A (zh) * | 2020-03-24 | 2020-06-09 | 烟台德邦科技有限公司 | 一种聚氨酯-丙烯酸酯结构胶及其制备方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1231085A (en) * | 1984-05-29 | 1988-01-05 | Denis J. Zalucha | Structural adhesive formulations |
| US5106928A (en) * | 1991-04-29 | 1992-04-21 | National Starch And Chemical Investment Holding Corporation | Acrylic adhesive composition and organoboron initiator system |
| US5453450A (en) * | 1993-06-16 | 1995-09-26 | Minnesota Mining And Manufacturing Company | Stabilized curable adhesives |
| CA2136882A1 (en) * | 1993-12-20 | 1995-06-21 | William J. Catena | Structural acrylic adhesives |
| JP3535167B2 (ja) * | 1994-02-22 | 2004-06-07 | ミネソタ マイニング アンド マニュファクチャリング カンパニー | 有機ホウ素アミン錯体に基づく重合開始剤システムを用いて製造される重合性組成物 |
-
1998
- 1998-06-12 EP EP98926581A patent/EP1098943B1/en not_active Expired - Lifetime
- 1998-06-12 BR BR9815905-4A patent/BR9815905A/pt not_active Application Discontinuation
- 1998-06-12 KR KR1020007014030A patent/KR100629832B1/ko not_active Expired - Fee Related
- 1998-06-12 CN CN988141094A patent/CN1216955C/zh not_active Expired - Fee Related
- 1998-06-12 DE DE69821265T patent/DE69821265T2/de not_active Expired - Lifetime
- 1998-06-12 AU AU78382/98A patent/AU7838298A/en not_active Abandoned
- 1998-06-12 WO PCT/US1998/012260 patent/WO1999064528A1/en not_active Ceased
- 1998-06-12 JP JP2000553522A patent/JP4373007B2/ja not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| KR100629832B1 (ko) | 2006-09-29 |
| BR9815905A (pt) | 2001-02-20 |
| JP2002517594A (ja) | 2002-06-18 |
| JP4373007B2 (ja) | 2009-11-25 |
| EP1098943A1 (en) | 2001-05-16 |
| CN1307622A (zh) | 2001-08-08 |
| CN1216955C (zh) | 2005-08-31 |
| WO1999064528A1 (en) | 1999-12-16 |
| EP1098943B1 (en) | 2004-01-21 |
| DE69821265D1 (de) | 2004-02-26 |
| KR20010052744A (ko) | 2001-06-25 |
| AU7838298A (en) | 1999-12-30 |
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| 8364 | No opposition during term of opposition |