JP2008518073A - 耐衝撃性シアノアクリレート組成物 - Google Patents
耐衝撃性シアノアクリレート組成物 Download PDFInfo
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- JP2008518073A JP2008518073A JP2007538604A JP2007538604A JP2008518073A JP 2008518073 A JP2008518073 A JP 2008518073A JP 2007538604 A JP2007538604 A JP 2007538604A JP 2007538604 A JP2007538604 A JP 2007538604A JP 2008518073 A JP2008518073 A JP 2008518073A
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- Prior art keywords
- acid
- cyanoacrylate
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- 239000000203 mixture Substances 0.000 title claims abstract description 115
- 229920001651 Cyanoacrylate Polymers 0.000 title claims abstract description 62
- MWCLLHOVUTZFKS-UHFFFAOYSA-N Methyl cyanoacrylate Chemical compound COC(=O)C(=C)C#N MWCLLHOVUTZFKS-UHFFFAOYSA-N 0.000 title claims abstract description 59
- 239000000853 adhesive Substances 0.000 claims abstract description 33
- 230000001070 adhesive effect Effects 0.000 claims abstract description 33
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 14
- 239000000758 substrate Substances 0.000 claims description 39
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 36
- 239000002253 acid Substances 0.000 claims description 34
- 238000000034 method Methods 0.000 claims description 29
- FGBJXOREULPLGL-UHFFFAOYSA-N ethyl cyanoacrylate Chemical compound CCOC(=O)C(=C)C#N FGBJXOREULPLGL-UHFFFAOYSA-N 0.000 claims description 27
- VTJUKNSKBAOEHE-UHFFFAOYSA-N calixarene Chemical class COC(=O)COC1=C(CC=2C(=C(CC=3C(=C(C4)C=C(C=3)C(C)(C)C)OCC(=O)OC)C=C(C=2)C(C)(C)C)OCC(=O)OC)C=C(C(C)(C)C)C=C1CC1=C(OCC(=O)OC)C4=CC(C(C)(C)C)=C1 VTJUKNSKBAOEHE-UHFFFAOYSA-N 0.000 claims description 18
- 229910001209 Low-carbon steel Inorganic materials 0.000 claims description 16
- 229910052782 aluminium Inorganic materials 0.000 claims description 16
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 16
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 claims description 14
- 239000000654 additive Substances 0.000 claims description 12
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 claims description 12
- KQTIIICEAUMSDG-UHFFFAOYSA-N tricarballylic acid Chemical compound OC(=O)CC(C(O)=O)CC(O)=O KQTIIICEAUMSDG-UHFFFAOYSA-N 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 239000000463 material Substances 0.000 claims description 10
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- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 claims description 8
- 150000002148 esters Chemical group 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 6
- UJMDYLWCYJJYMO-UHFFFAOYSA-N benzene-1,2,3-tricarboxylic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1C(O)=O UJMDYLWCYJJYMO-UHFFFAOYSA-N 0.000 claims description 6
- QMKYBPDZANOJGF-UHFFFAOYSA-N benzene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-N 0.000 claims description 6
- 150000003983 crown ethers Chemical class 0.000 claims description 6
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 6
- 230000000996 additive effect Effects 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- 229920001223 polyethylene glycol Polymers 0.000 claims description 5
- RLHGFJMGWQXPBW-UHFFFAOYSA-N 2-hydroxy-3-(1h-imidazol-5-ylmethyl)benzamide Chemical compound NC(=O)C1=CC=CC(CC=2NC=NC=2)=C1O RLHGFJMGWQXPBW-UHFFFAOYSA-N 0.000 claims description 4
- 229910000831 Steel Inorganic materials 0.000 claims description 4
- XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
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- 125000001188 haloalkyl group Chemical group 0.000 claims description 4
- 239000004014 plasticizer Substances 0.000 claims description 4
- 229940107700 pyruvic acid Drugs 0.000 claims description 4
- 239000003381 stabilizer Substances 0.000 claims description 4
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- 239000001124 (E)-prop-1-ene-1,2,3-tricarboxylic acid Substances 0.000 claims description 3
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 claims description 3
- TYEYBOSBBBHJIV-UHFFFAOYSA-N 2-oxobutanoic acid Chemical compound CCC(=O)C(O)=O TYEYBOSBBBHJIV-UHFFFAOYSA-N 0.000 claims description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 3
- 239000005977 Ethylene Substances 0.000 claims description 3
- 240000002871 Tectona grandis Species 0.000 claims description 3
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- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims description 3
- DYDNZUYNRZENMU-UHFFFAOYSA-N benzene-1,2,3-tricarboxylic acid;hydrate Chemical compound O.OC(=O)C1=CC=CC(C(O)=O)=C1C(O)=O DYDNZUYNRZENMU-UHFFFAOYSA-N 0.000 claims description 3
- GTZCVFVGUGFEME-IWQZZHSRSA-N cis-aconitic acid Chemical compound OC(=O)C\C(C(O)=O)=C\C(O)=O GTZCVFVGUGFEME-IWQZZHSRSA-N 0.000 claims description 3
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims description 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 3
- 150000004682 monohydrates Chemical class 0.000 claims description 3
- 125000006410 propenylene group Chemical group 0.000 claims description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
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- GTZCVFVGUGFEME-UHFFFAOYSA-N trans-aconitic acid Natural products OC(=O)CC(C(O)=O)=CC(O)=O GTZCVFVGUGFEME-UHFFFAOYSA-N 0.000 claims description 3
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 claims description 3
- 229940005605 valeric acid Drugs 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical group OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical group OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical group OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 2
- 150000001338 aliphatic hydrocarbons Chemical group 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000005012 alkyl thioether group Chemical group 0.000 claims description 2
- 125000000129 anionic group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical group O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 claims description 2
- 150000003254 radicals Chemical class 0.000 claims description 2
- BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical group OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052717 sulfur Chemical group 0.000 claims description 2
- 239000011593 sulfur Chemical group 0.000 claims description 2
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical group C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 claims description 2
- 239000013008 thixotropic agent Substances 0.000 claims description 2
- 230000015556 catabolic process Effects 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- 238000006731 degradation reaction Methods 0.000 claims 1
- 229920003048 styrene butadiene rubber Polymers 0.000 claims 1
- 239000012745 toughening agent Substances 0.000 claims 1
- 150000003628 tricarboxylic acids Chemical class 0.000 claims 1
- 150000001735 carboxylic acids Chemical class 0.000 abstract description 5
- 238000009472 formulation Methods 0.000 description 44
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
- 229940053009 ethyl cyanoacrylate Drugs 0.000 description 15
- 239000004830 Super Glue Substances 0.000 description 11
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 11
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- 150000007513 acids Chemical class 0.000 description 9
- 229910021485 fumed silica Inorganic materials 0.000 description 8
- 238000012360 testing method Methods 0.000 description 7
- -1 alkyl cyanoacrylate Chemical compound 0.000 description 6
- 230000000712 assembly Effects 0.000 description 6
- 238000000429 assembly Methods 0.000 description 6
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
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- 239000000178 monomer Substances 0.000 description 3
- VYPNMUSYTNBGQH-UHFFFAOYSA-N 2,2-dimethyl-1,3,6,9,12,15-hexaoxa-2-silacycloheptadecane Chemical compound C[Si]1(C)OCCOCCOCCOCCOCCO1 VYPNMUSYTNBGQH-UHFFFAOYSA-N 0.000 description 2
- JIOBGPYSBDFDAB-UHFFFAOYSA-N 2,2-dimethyl-1,3,6,9,12-pentaoxa-2-silacyclotetradecane Chemical compound C[Si]1(C)OCCOCCOCCOCCO1 JIOBGPYSBDFDAB-UHFFFAOYSA-N 0.000 description 2
- UXWKDYXFUUBISW-UHFFFAOYSA-N 2,2-dimethyl-1,3,6,9-tetraoxa-2-silacycloundecane Chemical compound C[Si]1(C)OCCOCCOCCO1 UXWKDYXFUUBISW-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
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- 229910020175 SiOH Inorganic materials 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 238000000576 coating method Methods 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
- 230000000694 effects Effects 0.000 description 2
- JJJFUHOGVZWXNQ-UHFFFAOYSA-N enbucrilate Chemical compound CCCCOC(=O)C(=C)C#N JJJFUHOGVZWXNQ-UHFFFAOYSA-N 0.000 description 2
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- AGJSNMGHAVDLRQ-HUUJSLGLSA-N methyl (2s)-2-[[(2r)-2-[[(2s)-2-[[(2r)-2-amino-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,3-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoate Chemical compound SC[C@H](N)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(=O)N[C@@H](CCSC)C(=O)OC)CC1=CC=C(O)C(C)=C1C AGJSNMGHAVDLRQ-HUUJSLGLSA-N 0.000 description 2
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- AXWCVSOBRFLCJG-UHFFFAOYSA-N 2,5,12,15,22,25-hexaoxatetracyclo[24.4.0.06,11.016,21]triaconta-1(30),6,8,10,16,18,20,26,28-nonaene Chemical compound O1CCOC2=CC=CC=C2OCCOC2=CC=CC=C2OCCOC2=CC=CC=C21 AXWCVSOBRFLCJG-UHFFFAOYSA-N 0.000 description 1
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- SVJYFWHFQPBIOY-UHFFFAOYSA-N 7,8,16,17-tetrahydro-6h,15h-dibenzo[b,i][1,4,8,11]tetraoxacyclotetradecine Chemical compound O1CCCOC2=CC=CC=C2OCCCOC2=CC=CC=C21 SVJYFWHFQPBIOY-UHFFFAOYSA-N 0.000 description 1
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- 239000004033 plastic Substances 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229940068918 polyethylene glycol 400 Drugs 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- ZTYMNUBYYQNBFP-UHFFFAOYSA-N propyl 2-cyanoprop-2-enoate Chemical compound CCCOC(=O)C(=C)C#N ZTYMNUBYYQNBFP-UHFFFAOYSA-N 0.000 description 1
- 229940076788 pyruvate Drugs 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 125000005415 substituted alkoxy group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
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- 239000002023 wood Substances 0.000 description 1
Images
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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
-
- 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
- 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
- C09J133/08—Homopolymers or copolymers of acrylic acid esters
-
- 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
- C09J133/10—Homopolymers or copolymers of methacrylic acid esters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerisation Methods In General (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US62390604P | 2004-11-01 | 2004-11-01 | |
| US11/119,703 US20060094833A1 (en) | 2004-11-01 | 2005-05-03 | Shock resistant cyanoacrylate compositions |
| PCT/IE2005/000108 WO2006048851A1 (en) | 2004-11-01 | 2005-09-27 | Shock resistant cyanoacrylate compositions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008518073A true JP2008518073A (ja) | 2008-05-29 |
| JP2008518073A5 JP2008518073A5 (enExample) | 2011-11-24 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007538604A Pending JP2008518073A (ja) | 2004-11-01 | 2005-09-27 | 耐衝撃性シアノアクリレート組成物 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US20060094833A1 (enExample) |
| EP (1) | EP1807476B1 (enExample) |
| JP (1) | JP2008518073A (enExample) |
| KR (1) | KR101107405B1 (enExample) |
| CN (1) | CN101052692B (enExample) |
| AT (1) | ATE557073T1 (enExample) |
| BR (1) | BRPI0517952B1 (enExample) |
| CA (1) | CA2582543C (enExample) |
| ES (1) | ES2385338T3 (enExample) |
| WO (1) | WO2006048851A1 (enExample) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2014522899A (ja) * | 2011-07-15 | 2014-09-08 | ヘンケル アイルランド リミテッド | シアノアクリレート組成物 |
| JP2015510003A (ja) * | 2012-01-25 | 2015-04-02 | ヘンケル ユーエス アイピー エルエルシー | シアノアクリレート組成物 |
| JP2022101160A (ja) * | 2020-12-24 | 2022-07-06 | 東亞合成株式会社 | ２－シアノアクリレート系接着剤組成物 |
| JP2022101159A (ja) * | 2020-12-24 | 2022-07-06 | 東亞合成株式会社 | ２－シアノアクリレート系接着剤組成物 |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2601781T3 (es) | 2005-07-11 | 2017-02-16 | Henkel IP & Holding GmbH | Composiciones de cianoacrilato endurecido |
| US7659423B1 (en) | 2006-04-18 | 2010-02-09 | Loctite (R&D) Limited | Method of preparing electron deficient olefins in polar solvents |
| US7569719B1 (en) | 2006-10-25 | 2009-08-04 | Loctite (R&D) Limited | Method of preparing electron deficient olefins |
| US7718821B1 (en) | 2006-12-19 | 2010-05-18 | Loctite (R&D) Limited | Method of preparing electron deficient olefins |
| US7973119B1 (en) | 2007-10-24 | 2011-07-05 | Loctite (R&D) Limited | Adhesive systems using imines and salts thereof and precursurs to electron deficient olefins |
| US8686105B2 (en) | 2007-10-24 | 2014-04-01 | Henkel IP & Holding GmbH | Adhesive systems using imines and salts thereof, precursors to electron deficient olefins and coreactants therefor |
| CN102083784A (zh) * | 2007-10-24 | 2011-06-01 | 洛克泰特(R&D)有限公司 | 缺电子烯烃和由其制备的可固化组合物 |
| CA2703596A1 (en) * | 2007-10-24 | 2009-04-30 | Loctite (R&D) Limited | Activated methylene reagents and curable compositions prepared therefrom |
| US8053589B1 (en) | 2007-10-24 | 2011-11-08 | Henkel Ireland Limited | Imines and methods of preparing electron deficient olefins using such novel imines |
| US8207264B2 (en) * | 2008-07-11 | 2012-06-26 | Tyco Healthcare Group Lp | Functionalized inclusion complexes as crosslinkers |
| KR20150083127A (ko) * | 2008-09-26 | 2015-07-16 | 헨켈 아이피 앤드 홀딩 게엠베하 | 비유동성 형태의 시아노아크릴레이트 조성물 |
| US9457613B2 (en) * | 2008-09-26 | 2016-10-04 | Henkel IP & Holding GmbH | Cyanoacrylate compositions in non-flowable forms |
| US20100083790A1 (en) * | 2008-10-06 | 2010-04-08 | Graney Jon P | Flywheel device |
| US10196471B1 (en) | 2008-10-24 | 2019-02-05 | Henkel IP & Holding GmbH | Curable composition having an electron deficient olefin |
| US8399698B1 (en) | 2008-10-24 | 2013-03-19 | Henkel Ireland Limited | Substituted activated methylene reagents and methods of using such reagents to form electron deficient olefins |
| DE102009012187A1 (de) * | 2009-02-26 | 2010-09-02 | Aesculap Aktiengesellschaft | Medizinische Klebstoffzusammensetzung |
| WO2010125195A1 (en) | 2009-05-01 | 2010-11-04 | Loctite (R&D) Limited | Cyanoacrylate compositions |
| KR20130115254A (ko) | 2010-09-14 | 2013-10-21 | 파워 트리 코포레이션 | 복합재 플라이휠 |
| CN101967354B (zh) * | 2010-09-15 | 2013-07-31 | 北京天山新材料技术股份有限公司 | 低白化α-氰基丙烯酸酯胶粘剂 |
| CN105246872B (zh) * | 2013-05-21 | 2019-08-13 | 汉高知识产权控股有限责任公司 | 氰基丙烯酸酯组合物 |
| GB2567867B (en) * | 2017-10-27 | 2020-09-16 | Henkel IP & Holding GmbH | Toughened, low odor/low bloom cyanoacrylate compositions |
| GB2567869B (en) * | 2017-10-27 | 2021-08-11 | Henkel IP & Holding GmbH | Toughened humidity/thermal resistant cyanoacrylate compositions |
| CN110343470A (zh) * | 2019-07-18 | 2019-10-18 | 长江师范学院 | 一种墙纸粘合剂及其制作方法 |
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| JPS5277145A (en) * | 1975-12-24 | 1977-06-29 | Toagosei Chem Ind Co Ltd | Adhesive composition |
| JPS5290536A (en) * | 1976-01-23 | 1977-07-29 | Toagosei Chem Ind Co Ltd | Adhesive composition |
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| IE34874B1 (en) * | 1971-01-13 | 1975-09-03 | Intercontinental Chem Co Ltd | Cyanoacrylate adhesive compositions |
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| JPS5278933A (en) * | 1975-12-26 | 1977-07-02 | Toagosei Chem Ind Co Ltd | Adhesive composition |
| US4196271A (en) * | 1975-12-24 | 1980-04-01 | Toagosei Chemical Industry Co., Ltd. | Adhesive composition |
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| JPS57164175A (en) * | 1981-04-03 | 1982-10-08 | Japan Synthetic Rubber Co Ltd | Impact-resistant instantaneous adhesive composition |
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| US4718966A (en) * | 1984-01-30 | 1988-01-12 | Loctite (Ireland) Ltd. | Bonding method utilizing cyanoacrylate adhesive having calixarene accelerator |
| US4695615A (en) * | 1984-11-21 | 1987-09-22 | Loctite (Ireland) Limited | Instant adhesive composition utilizing mixed functionality calixarenes as accelerators |
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| US4837260A (en) * | 1986-05-23 | 1989-06-06 | Toagosei Chemical Industry Co., Ltd. | Cyanoacrylate compositions |
| JPH0730292B2 (ja) * | 1986-06-24 | 1995-04-05 | 東亞合成株式会社 | 接着剤組成物 |
| US4950701A (en) * | 1986-07-02 | 1990-08-21 | Cemedine Company, Ltd. | Bonding method and adhesive useful for the method |
| DE4009621A1 (de) * | 1990-03-26 | 1991-10-02 | Henkel Kgaa | (alpha) -cyanacrylatklebstoffzusammensetzungen |
| US6323275B2 (en) * | 1992-05-28 | 2001-11-27 | Toagosei Co., Ltd. | Cyanoacrylate adhesive composition |
| DE19859638A1 (de) * | 1998-12-23 | 2000-07-20 | Henkel Kgaa | Aktivator für Cyanacrylat-Klebstoffe |
| EP1372130A4 (en) * | 2001-03-19 | 2008-03-12 | Fujitsu Ltd | VIDEO SIGNAL SWITCHING CONTROL, DISPLAY DEVICE AND COMPUTER |
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2005
- 2005-05-03 US US11/119,703 patent/US20060094833A1/en not_active Abandoned
- 2005-09-27 BR BRPI0517952-1A patent/BRPI0517952B1/pt not_active IP Right Cessation
- 2005-09-27 AT AT05786881T patent/ATE557073T1/de active
- 2005-09-27 WO PCT/IE2005/000108 patent/WO2006048851A1/en not_active Ceased
- 2005-09-27 JP JP2007538604A patent/JP2008518073A/ja active Pending
- 2005-09-27 ES ES05786881T patent/ES2385338T3/es active Active
- 2005-09-27 KR KR1020077009805A patent/KR101107405B1/ko not_active Expired - Fee Related
- 2005-09-27 EP EP05786881A patent/EP1807476B1/en not_active Expired - Lifetime
- 2005-09-27 CN CN200580037402.8A patent/CN101052692B/zh not_active Expired - Fee Related
- 2005-09-27 CA CA2582543A patent/CA2582543C/en not_active Expired - Fee Related
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| JPS5277145A (en) * | 1975-12-24 | 1977-06-29 | Toagosei Chem Ind Co Ltd | Adhesive composition |
| JPS5290536A (en) * | 1976-01-23 | 1977-07-29 | Toagosei Chem Ind Co Ltd | Adhesive composition |
| JPS588771A (ja) * | 1981-07-08 | 1983-01-18 | Taoka Chem Co Ltd | 接着剤組成物 |
| JPS6366276A (ja) * | 1986-07-02 | 1988-03-24 | Semedain Kk | 接着方法 |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2014522899A (ja) * | 2011-07-15 | 2014-09-08 | ヘンケル アイルランド リミテッド | シアノアクリレート組成物 |
| JP2015510003A (ja) * | 2012-01-25 | 2015-04-02 | ヘンケル ユーエス アイピー エルエルシー | シアノアクリレート組成物 |
| JP2022101160A (ja) * | 2020-12-24 | 2022-07-06 | 東亞合成株式会社 | ２－シアノアクリレート系接着剤組成物 |
| JP2022101159A (ja) * | 2020-12-24 | 2022-07-06 | 東亞合成株式会社 | ２－シアノアクリレート系接着剤組成物 |
| JP7647096B2 (ja) | 2020-12-24 | 2025-03-18 | 東亞合成株式会社 | ２－シアノアクリレート系接着剤組成物 |
| JP7647097B2 (ja) | 2020-12-24 | 2025-03-18 | 東亞合成株式会社 | ２－シアノアクリレート系接着剤組成物 |
Also Published As
| Publication number | Publication date |
|---|---|
| BRPI0517952A (pt) | 2008-10-21 |
| KR20070073840A (ko) | 2007-07-10 |
| WO2006048851A1 (en) | 2006-05-11 |
| US20060094833A1 (en) | 2006-05-04 |
| ATE557073T1 (de) | 2012-05-15 |
| BRPI0517952B1 (pt) | 2019-10-01 |
| CN101052692A (zh) | 2007-10-10 |
| EP1807476A1 (en) | 2007-07-18 |
| CA2582543A1 (en) | 2006-05-11 |
| ES2385338T3 (es) | 2012-07-23 |
| KR101107405B1 (ko) | 2012-01-19 |
| CN101052692B (zh) | 2015-03-11 |
| CA2582543C (en) | 2012-12-04 |
| EP1807476B1 (en) | 2012-05-09 |
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