DE60112255T2 - Polymerisationsinitiator-systeme und haftzusammensetzungen, die vinylaromatische verbindungen enthalten - Google Patents
Polymerisationsinitiator-systeme und haftzusammensetzungen, die vinylaromatische verbindungen enthalten Download PDFInfo
- Publication number
- DE60112255T2 DE60112255T2 DE60112255T DE60112255T DE60112255T2 DE 60112255 T2 DE60112255 T2 DE 60112255T2 DE 60112255 T DE60112255 T DE 60112255T DE 60112255 T DE60112255 T DE 60112255T DE 60112255 T2 DE60112255 T2 DE 60112255T2
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- Germany
- Prior art keywords
- adhesive composition
- group
- vinyl aromatic
- aromatic compound
- formula
- 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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- 239000000203 mixture Substances 0.000 title claims abstract description 251
- 239000003505 polymerization initiator Substances 0.000 title claims abstract description 13
- 150000001875 compounds Chemical class 0.000 title claims description 23
- 239000000853 adhesive Substances 0.000 claims abstract description 203
- 230000001070 adhesive effect Effects 0.000 claims abstract description 203
- -1 vinyl aromatic compound Chemical class 0.000 claims abstract description 111
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 71
- 239000000178 monomer Substances 0.000 claims abstract description 61
- 239000000758 substrate Substances 0.000 claims abstract description 36
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 36
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- 229910052736 halogen Inorganic materials 0.000 claims description 16
- 150000002367 halogens Chemical class 0.000 claims description 16
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 15
- MNLAVFKVRUQAKW-UHFFFAOYSA-N VR nerve agent Chemical compound CCN(CC)CCSP(C)(=O)OCC(C)C MNLAVFKVRUQAKW-UHFFFAOYSA-N 0.000 claims description 15
- RWRIWBAIICGTTQ-UHFFFAOYSA-N difluoromethane Chemical compound FCF RWRIWBAIICGTTQ-UHFFFAOYSA-N 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
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- WTFAGPBUAGFMQX-UHFFFAOYSA-N 1-[2-[2-(2-aminopropoxy)propoxy]propoxy]propan-2-amine Chemical compound CC(N)COCC(C)OCC(C)OCC(C)N WTFAGPBUAGFMQX-UHFFFAOYSA-N 0.000 description 8
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- 230000000052 comparative effect Effects 0.000 description 7
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 238000004566 IR spectroscopy Methods 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 239000003522 acrylic cement Substances 0.000 description 4
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 4
- 238000004026 adhesive bonding Methods 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 150000008064 anhydrides Chemical class 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 150000001555 benzenes Chemical group 0.000 description 4
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
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- 239000012975 dibutyltin dilaurate Substances 0.000 description 4
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- 229910052760 oxygen Inorganic materials 0.000 description 4
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- 238000002360 preparation method Methods 0.000 description 4
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- 239000003381 stabilizer Substances 0.000 description 4
- ZVEMLYIXBCTVOF-UHFFFAOYSA-N 1-(2-isocyanatopropan-2-yl)-3-prop-1-en-2-ylbenzene Chemical compound CC(=C)C1=CC=CC(C(C)(C)N=C=O)=C1 ZVEMLYIXBCTVOF-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
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- LCXXNKZQVOXMEH-UHFFFAOYSA-N Tetrahydrofurfuryl methacrylate Chemical compound CC(=C)C(=O)OCC1CCCO1 LCXXNKZQVOXMEH-UHFFFAOYSA-N 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
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- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 3
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- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 2
- YOIZTLBZAMFVPK-UHFFFAOYSA-N 2-(3-ethoxy-4-hydroxyphenyl)-2-hydroxyacetic acid Chemical compound CCOC1=CC(C(O)C(O)=O)=CC=C1O YOIZTLBZAMFVPK-UHFFFAOYSA-N 0.000 description 2
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- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical group CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
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- KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 description 1
- SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 description 1
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- IQLBCEYWTAOHRS-UHFFFAOYSA-N 2-(2-hydroxyethoxy)ethanol;n-propylpropan-1-amine Chemical compound CCCNCCC.OCCOCCO IQLBCEYWTAOHRS-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 1
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- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
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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 description 1
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- MRVWKSCQNHUHLZ-UHFFFAOYSA-N n-[2-(2-aminoethylamino)ethyl]prop-2-enamide Chemical compound NCCNCCNC(=O)C=C MRVWKSCQNHUHLZ-UHFFFAOYSA-N 0.000 description 1
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- FXLOVSHXALFLKQ-UHFFFAOYSA-N p-tolualdehyde Chemical compound CC1=CC=C(C=O)C=C1 FXLOVSHXALFLKQ-UHFFFAOYSA-N 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
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- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
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- 238000011417 postcuring Methods 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
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- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920001897 terpolymer Polymers 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
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical compound FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer 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
- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical compound CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-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
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerization Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US525368 | 2000-03-15 | ||
| US09/525,368 US6479602B1 (en) | 2000-03-15 | 2000-03-15 | Polymerization initiator systems and bonding compositions comprising vinyl aromatic compounds |
| PCT/US2001/004752 WO2001068783A2 (en) | 2000-03-15 | 2001-02-14 | Polymerization initiator systems and bonding compositions comprising vinyl aromatic compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60112255D1 DE60112255D1 (de) | 2005-09-01 |
| DE60112255T2 true DE60112255T2 (de) | 2006-05-24 |
Family
ID=24092956
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60112255T Expired - Lifetime DE60112255T2 (de) | 2000-03-15 | 2001-02-14 | Polymerisationsinitiator-systeme und haftzusammensetzungen, die vinylaromatische verbindungen enthalten |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US6479602B1 (enExample) |
| EP (1) | EP1263907B1 (enExample) |
| JP (2) | JP5073906B2 (enExample) |
| CN (1) | CN1253477C (enExample) |
| AT (1) | ATE300589T1 (enExample) |
| BR (1) | BR0109243A (enExample) |
| DE (1) | DE60112255T2 (enExample) |
| WO (1) | WO2001068783A2 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102019200736A1 (de) * | 2019-01-22 | 2020-07-23 | Tesa Se | Reaktives 2-Komponentenklebesystem in Filmform auf Basis von geruchsneutralen Acrylmonomeren |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6812308B2 (en) * | 2000-11-21 | 2004-11-02 | 3M Innovative Properties Company | Initiator systems and adhesive compositions made therewith |
| MY123559A (en) * | 2000-05-18 | 2006-05-31 | Nat Starch & Chemical Investment Holding Corp | Curable electron donor compounds |
| EP1373327B1 (en) | 2001-02-21 | 2007-10-10 | 3M Innovative Properties Company | Polymerizable system with a long work-life |
| US6849569B2 (en) * | 2001-12-31 | 2005-02-01 | 3M Innovative Properties Company | Initiator systems comprising β-ketone compounds |
| US6734268B2 (en) * | 2001-12-31 | 2004-05-11 | 3M Innovative Properties Company | Metal salt modifiers for bonding compositions |
| GB0311121D0 (en) | 2003-05-15 | 2003-06-18 | Avecia Ltd | Polyurethane dispersants |
| US20040229990A1 (en) * | 2003-05-16 | 2004-11-18 | Lord Corporation | Acrylic structural adhesive having improved T-peel strength |
| US7220807B2 (en) * | 2004-02-17 | 2007-05-22 | Penn State Research Foundation | Process of preparing functional fluoropolymers |
| US6911509B1 (en) * | 2004-02-17 | 2005-06-28 | The Penn State Research Foundation | Functional fluoropolymers and process therefor |
| DE102005049681B4 (de) * | 2005-10-14 | 2011-03-10 | Henkel Ag & Co. Kgaa | Hülsenförmige Etiketten |
| US8742050B2 (en) | 2008-03-28 | 2014-06-03 | Henkel US IP LLC | Two part hybrid adhesive |
| KR101867786B1 (ko) * | 2009-06-26 | 2018-06-15 | 바스프 코팅스 게엠베하 | 페인트 코팅계 및 다층 페인트 코팅의 제조 방법 |
| GB2497300A (en) * | 2011-12-06 | 2013-06-12 | Tyco Electronics Ltd Uk | Method of repairing or encapsulating a cable |
| CN105377918B (zh) * | 2013-07-12 | 2017-07-11 | 3M创新有限公司 | 粘结组合物及其组分以及其使用方法 |
| 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 |
| EP3183311A1 (en) | 2014-08-18 | 2017-06-28 | LORD Corporation | Method for low temperature bonding of elastomers |
| JP6404645B2 (ja) * | 2014-08-28 | 2018-10-10 | 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 |
| JP6258563B1 (ja) | 2014-11-14 | 2018-01-10 | 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 |
| JP6672759B2 (ja) * | 2015-12-10 | 2020-03-25 | 日立化成株式会社 | 樹脂組成物、及び接着剤 |
| JP6676946B2 (ja) * | 2015-12-10 | 2020-04-08 | 日立化成株式会社 | 樹脂組成物 |
| EP3541629A4 (en) * | 2016-11-17 | 2020-05-27 | 3M Innovative Properties Company | COMPOSITIONS COMPRISING A POLYMER AND HOLLOW CERAMIC MICROSPHERES AND METHOD OF MANUFACTURING A THREE-DIMENSIONAL ARTICLE |
| FR3098815B1 (fr) * | 2019-07-18 | 2021-06-25 | Bostik Sa | Procédé de polymérisation avec un complexe de borane-amine |
| CN113403017A (zh) * | 2020-09-30 | 2021-09-17 | 丁建利 | 一种金属与塑料粘结用胶粘剂 |
| US20240271021A1 (en) | 2021-06-02 | 2024-08-15 | 3M Innovative Properties Company | Composition including cyclic imide-containing monomer and organoborane complex and related articles and methods |
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-
2000
- 2000-03-15 US US09/525,368 patent/US6479602B1/en not_active Expired - Lifetime
-
2001
- 2001-02-14 EP EP01910679A patent/EP1263907B1/en not_active Expired - Lifetime
- 2001-02-14 DE DE60112255T patent/DE60112255T2/de not_active Expired - Lifetime
- 2001-02-14 WO PCT/US2001/004752 patent/WO2001068783A2/en not_active Ceased
- 2001-02-14 JP JP2001567270A patent/JP5073906B2/ja not_active Expired - Fee Related
- 2001-02-14 CN CNB018065767A patent/CN1253477C/zh not_active Expired - Fee Related
- 2001-02-14 AT AT01910679T patent/ATE300589T1/de not_active IP Right Cessation
- 2001-02-14 BR BR0109243-0A patent/BR0109243A/pt not_active Application Discontinuation
-
2012
- 2012-05-10 JP JP2012108523A patent/JP5443538B2/ja not_active Expired - Fee Related
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102019200736A1 (de) * | 2019-01-22 | 2020-07-23 | Tesa Se | Reaktives 2-Komponentenklebesystem in Filmform auf Basis von geruchsneutralen Acrylmonomeren |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2003526729A (ja) | 2003-09-09 |
| ATE300589T1 (de) | 2005-08-15 |
| WO2001068783A2 (en) | 2001-09-20 |
| EP1263907B1 (en) | 2005-07-27 |
| JP5073906B2 (ja) | 2012-11-14 |
| EP1263907A2 (en) | 2002-12-11 |
| JP5443538B2 (ja) | 2014-03-19 |
| BR0109243A (pt) | 2002-12-24 |
| JP2012158767A (ja) | 2012-08-23 |
| WO2001068783A3 (en) | 2002-02-21 |
| DE60112255D1 (de) | 2005-09-01 |
| CN1253477C (zh) | 2006-04-26 |
| HK1052525A1 (en) | 2003-09-19 |
| CN1418246A (zh) | 2003-05-14 |
| US6479602B1 (en) | 2002-11-12 |
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