JPH0332591B2 - - Google Patents
Info
- Publication number
- JPH0332591B2 JPH0332591B2 JP57076438A JP7643882A JPH0332591B2 JP H0332591 B2 JPH0332591 B2 JP H0332591B2 JP 57076438 A JP57076438 A JP 57076438A JP 7643882 A JP7643882 A JP 7643882A JP H0332591 B2 JPH0332591 B2 JP H0332591B2
- Authority
- JP
- Japan
- Prior art keywords
- weight
- composition
- adhesive
- adhesive composition
- composition according
- 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
Links
- 239000000203 mixture Substances 0.000 claims description 81
- 239000000853 adhesive Substances 0.000 claims description 27
- 230000001070 adhesive effect Effects 0.000 claims description 27
- 239000000178 monomer Substances 0.000 claims description 17
- -1 acrylate ester Chemical class 0.000 claims description 13
- 239000000654 additive Substances 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 229920001651 Cyanoacrylate Polymers 0.000 claims description 11
- MWCLLHOVUTZFKS-UHFFFAOYSA-N Methyl cyanoacrylate Chemical compound COC(=O)C(=C)C#N MWCLLHOVUTZFKS-UHFFFAOYSA-N 0.000 claims description 10
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 10
- 239000003112 inhibitor Substances 0.000 claims description 10
- 230000000996 additive effect Effects 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 6
- FGBJXOREULPLGL-UHFFFAOYSA-N ethyl cyanoacrylate Chemical group CCOC(=O)C(=C)C#N FGBJXOREULPLGL-UHFFFAOYSA-N 0.000 claims description 6
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N 1,4-Benzenediol Natural products OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 5
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 5
- 238000010539 anionic addition polymerization reaction Methods 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 238000010526 radical polymerization reaction Methods 0.000 claims description 5
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Chemical compound CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 3
- 125000005336 allyloxy group Chemical group 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 229940053009 ethyl cyanoacrylate Drugs 0.000 claims description 3
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 3
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 claims description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 2
- HWSSEYVMGDIFMH-UHFFFAOYSA-N 2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOC(=O)C(C)=C HWSSEYVMGDIFMH-UHFFFAOYSA-N 0.000 claims description 2
- LTHJXDSHSVNJKG-UHFFFAOYSA-N 2-[2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOCCOC(=O)C(C)=C LTHJXDSHSVNJKG-UHFFFAOYSA-N 0.000 claims description 2
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical group CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 claims description 2
- YYVYAPXYZVYDHN-UHFFFAOYSA-N 9,10-phenanthroquinone Chemical compound C1=CC=C2C(=O)C(=O)C3=CC=CC=C3C2=C1 YYVYAPXYZVYDHN-UHFFFAOYSA-N 0.000 claims description 2
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 2
- 229930192627 Naphthoquinone Natural products 0.000 claims description 2
- LCXXNKZQVOXMEH-UHFFFAOYSA-N Tetrahydrofurfuryl methacrylate Chemical compound CC(=C)C(=O)OCC1CCCO1 LCXXNKZQVOXMEH-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 claims description 2
- 150000004056 anthraquinones Chemical class 0.000 claims description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 229940119545 isobornyl methacrylate Drugs 0.000 claims description 2
- 150000002791 naphthoquinones Chemical class 0.000 claims description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 3
- CLHYKAZPWIRRRD-UHFFFAOYSA-N 1-hydroxypropane-1-sulfonic acid Chemical compound CCC(O)S(O)(=O)=O CLHYKAZPWIRRRD-UHFFFAOYSA-N 0.000 claims 1
- 239000004698 Polyethylene Substances 0.000 claims 1
- 125000005399 allylmethacrylate group Chemical group 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- 125000000687 hydroquinonyl group Chemical group C1(O)=C(C=C(O)C=C1)* 0.000 claims 1
- 229920000573 polyethylene Polymers 0.000 claims 1
- 150000003512 tertiary amines Chemical class 0.000 claims 1
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 4
- 229910000831 Steel Inorganic materials 0.000 description 4
- 239000004830 Super Glue Substances 0.000 description 4
- 230000032683 aging Effects 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 239000010959 steel Substances 0.000 description 4
- 230000004580 weight loss Effects 0.000 description 4
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 3
- 239000013466 adhesive and sealant Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 150000003923 2,5-pyrrolediones Chemical class 0.000 description 2
- 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 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 239000012790 adhesive layer Substances 0.000 description 2
- NLCKLZIHJQEMCU-UHFFFAOYSA-N cyano prop-2-enoate Chemical class C=CC(=O)OC#N NLCKLZIHJQEMCU-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- FBCQUCJYYPMKRO-UHFFFAOYSA-N prop-2-enyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC=C FBCQUCJYYPMKRO-UHFFFAOYSA-N 0.000 description 2
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 2
- XOJWAAUYNWGQAU-UHFFFAOYSA-N 4-(2-methylprop-2-enoyloxy)butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCOC(=O)C(C)=C XOJWAAUYNWGQAU-UHFFFAOYSA-N 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000005396 acrylic acid ester group Chemical group 0.000 description 1
- 229920006222 acrylic ester polymer Polymers 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000013043 chemical agent Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- YDKNBNOOCSNPNS-UHFFFAOYSA-N methyl 1,3-benzoxazole-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OC)=NC2=C1 YDKNBNOOCSNPNS-UHFFFAOYSA-N 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 150000003009 phosphonic acids Chemical class 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- ITCZEZQMUWEPQP-UHFFFAOYSA-N prop-2-enyl 2-cyanoprop-2-enoate Chemical compound C=CCOC(=O)C(=C)C#N ITCZEZQMUWEPQP-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000001757 thermogravimetry curve Methods 0.000 description 1
- 239000012815 thermoplastic material Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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)
- Sealing Material Composition (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US24656081A | 1981-06-01 | 1981-06-01 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57207664A JPS57207664A (en) | 1982-12-20 |
| JPH0332591B2 true JPH0332591B2 (ru) | 1991-05-13 |
Family
ID=22931200
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57076438A Granted JPS57207664A (en) | 1981-06-01 | 1982-05-07 | Liquid adhesive and sealant composition |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS57207664A (ru) |
| AU (2) | AU8433682A (ru) |
| BE (1) | BE893260A (ru) |
| BR (1) | BR8203122A (ru) |
| CA (1) | CA1212199A (ru) |
| DE (1) | DE3220591A1 (ru) |
| FR (1) | FR2506777A1 (ru) |
| GB (1) | GB2100273B (ru) |
| IE (1) | IE53977B1 (ru) |
| IT (1) | IT1197429B (ru) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5739205A (en) * | 1994-06-08 | 1998-04-14 | Taoka Chemical Company, Limited | α-cyanoacrylate adhesive composition |
| DE69503844T2 (de) * | 1994-06-08 | 1999-04-22 | Taoka Chemical Co Ltd | Klebemittelzusammensetzung auf Alphacyanoacrylat Basis |
| WO2007008971A1 (en) * | 2005-07-11 | 2007-01-18 | Henkel Corporation | Toughened cyanoacrylate compositions |
| JP4976575B1 (ja) * | 2011-07-07 | 2012-07-18 | ナミックス株式会社 | 樹脂組成物 |
| KR101840906B1 (ko) * | 2012-01-25 | 2018-03-21 | 헨켈 아이피 앤드 홀딩 게엠베하 | 시아노아크릴레이트 조성물 |
| WO2024062930A1 (ja) * | 2022-09-22 | 2024-03-28 | 株式会社クラレ | 接着剤、硬化物及び部材 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4922433A (ru) * | 1972-06-21 | 1974-02-27 | ||
| JPS49133430A (ru) * | 1973-04-24 | 1974-12-21 | ||
| JPS565873A (en) * | 1979-06-29 | 1981-01-21 | Taoka Chem Co Ltd | Adhesive composition |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2816093A (en) * | 1954-06-02 | 1957-12-10 | Eastman Kodak Co | Mixed adhesive compositions including alpha-cyanoacrylate esters |
| US3692752A (en) * | 1968-10-31 | 1972-09-19 | Matsumoto Seiyaku Kogyo Kk | Adhesive composition containing {60 -cyanoacrylate as its main ingredient |
| US3928286A (en) * | 1973-04-24 | 1975-12-23 | Tokyo Shibaura Electric Co | Heat-resistant adhesive composition from a bis-maleimide, an alpha-cyanoacrylate and optionally a diamine |
| GB1415102A (en) * | 1973-11-07 | 1975-11-26 | Trofimov N N Etlis V S | Adhesives |
-
1982
- 1982-04-28 CA CA000401860A patent/CA1212199A/en not_active Expired
- 1982-05-06 IE IE1083/82A patent/IE53977B1/en not_active IP Right Cessation
- 1982-05-07 JP JP57076438A patent/JPS57207664A/ja active Granted
- 1982-05-18 IT IT48441/82A patent/IT1197429B/it active
- 1982-05-21 BE BE0/208152A patent/BE893260A/fr not_active IP Right Cessation
- 1982-05-26 GB GB8215392A patent/GB2100273B/en not_active Expired
- 1982-05-28 FR FR8209346A patent/FR2506777A1/fr not_active Withdrawn
- 1982-05-28 BR BR8203122A patent/BR8203122A/pt unknown
- 1982-05-31 AU AU84336/82A patent/AU8433682A/en not_active Abandoned
- 1982-06-01 DE DE19823220591 patent/DE3220591A1/de not_active Ceased
-
1988
- 1988-03-17 AU AU13239/88A patent/AU1323988A/en not_active Abandoned
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4922433A (ru) * | 1972-06-21 | 1974-02-27 | ||
| JPS49133430A (ru) * | 1973-04-24 | 1974-12-21 | ||
| JPS565873A (en) * | 1979-06-29 | 1981-01-21 | Taoka Chem Co Ltd | Adhesive composition |
Also Published As
| Publication number | Publication date |
|---|---|
| AU8433682A (en) | 1982-12-09 |
| BE893260A (fr) | 1982-11-22 |
| GB2100273B (en) | 1985-07-03 |
| IE821083L (en) | 1982-12-01 |
| AU1323988A (en) | 1988-06-09 |
| IE53977B1 (en) | 1989-05-10 |
| IT1197429B (it) | 1988-11-30 |
| IT8248441A0 (it) | 1982-05-18 |
| JPS57207664A (en) | 1982-12-20 |
| BR8203122A (pt) | 1983-05-10 |
| FR2506777A1 (fr) | 1982-12-03 |
| DE3220591A1 (de) | 1983-01-05 |
| CA1212199A (en) | 1986-09-30 |
| GB2100273A (en) | 1982-12-22 |
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