JP2016511317A - シアノアクリレート組成物 - Google Patents
シアノアクリレート組成物 Download PDFInfo
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- JP2016511317A JP2016511317A JP2015562372A JP2015562372A JP2016511317A JP 2016511317 A JP2016511317 A JP 2016511317A JP 2015562372 A JP2015562372 A JP 2015562372A JP 2015562372 A JP2015562372 A JP 2015562372A JP 2016511317 A JP2016511317 A JP 2016511317A
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- Prior art keywords
- crown
- cyanoacrylate
- composition
- dibenzo
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- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 66
- MWCLLHOVUTZFKS-UHFFFAOYSA-N Methyl cyanoacrylate Chemical compound COC(=O)C(=C)C#N MWCLLHOVUTZFKS-UHFFFAOYSA-N 0.000 title claims description 23
- 229920001651 Cyanoacrylate Polymers 0.000 title claims description 22
- ITCZEZQMUWEPQP-UHFFFAOYSA-N prop-2-enyl 2-cyanoprop-2-enoate Chemical compound C=CCOC(=O)C(=C)C#N ITCZEZQMUWEPQP-UHFFFAOYSA-N 0.000 claims abstract description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 10
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000000758 substrate Substances 0.000 claims description 20
- FGBJXOREULPLGL-UHFFFAOYSA-N ethyl cyanoacrylate Chemical compound CCOC(=O)C(=C)C#N FGBJXOREULPLGL-UHFFFAOYSA-N 0.000 claims description 18
- 239000000853 adhesive Substances 0.000 claims description 15
- 230000001070 adhesive effect Effects 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 14
- 239000004830 Super Glue Substances 0.000 claims description 13
- 150000008065 acid anhydrides Chemical class 0.000 claims description 12
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims description 10
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical group CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 150000003983 crown ethers Chemical class 0.000 claims description 7
- -1 hydrogenated aromatic anhydride Chemical class 0.000 claims description 7
- 229920000858 Cyclodextrin Polymers 0.000 claims description 6
- 239000000463 material Substances 0.000 claims description 6
- VTJUKNSKBAOEHE-UHFFFAOYSA-N calixarene Chemical compound 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 5
- 239000003381 stabilizer Substances 0.000 claims description 5
- 229920001223 polyethylene glycol Polymers 0.000 claims description 4
- 229910000831 Steel Inorganic materials 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 239000000178 monomer Substances 0.000 claims description 3
- 239000010959 steel Substances 0.000 claims description 3
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- 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 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- YSSSPARMOAYJTE-UHFFFAOYSA-N dibenzo-18-crown-6 Chemical compound O1CCOCCOC2=CC=CC=C2OCCOCCOC2=CC=CC=C21 YSSSPARMOAYJTE-UHFFFAOYSA-N 0.000 claims description 2
- MXCSCGGRLMRZMF-UHFFFAOYSA-N dibenzo-30-crown-10 Chemical compound O1CCOCCOCCOCCOC2=CC=CC=C2OCCOCCOCCOCCOC2=CC=CC=C21 MXCSCGGRLMRZMF-UHFFFAOYSA-N 0.000 claims description 2
- BBGKDYHZQOSNMU-UHFFFAOYSA-N dicyclohexano-18-crown-6 Chemical compound O1CCOCCOC2CCCCC2OCCOCCOC2CCCCC21 BBGKDYHZQOSNMU-UHFFFAOYSA-N 0.000 claims description 2
- QMLGNDFKJAFKGZ-UHFFFAOYSA-N dicyclohexano-24-crown-8 Chemical compound O1CCOCCOCCOC2CCCCC2OCCOCCOCCOC2CCCCC21 QMLGNDFKJAFKGZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 150000002440 hydroxy compounds Chemical class 0.000 claims description 2
- 150000003254 radicals Chemical class 0.000 claims description 2
- 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 claims description 2
- 150000003985 15-crown-5 derivatives Chemical group 0.000 claims 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims 1
- 239000000470 constituent Substances 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- 230000000087 stabilizing effect Effects 0.000 claims 1
- 229910001209 Low-carbon steel Inorganic materials 0.000 description 10
- 229940053009 ethyl cyanoacrylate Drugs 0.000 description 8
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- JJJFUHOGVZWXNQ-UHFFFAOYSA-N enbucrilate Chemical compound CCCCOC(=O)C(=C)C#N JJJFUHOGVZWXNQ-UHFFFAOYSA-N 0.000 description 3
- 229950010048 enbucrilate Drugs 0.000 description 3
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 3
- 239000004926 polymethyl methacrylate Substances 0.000 description 3
- IJVRPNIWWODHHA-UHFFFAOYSA-N 2-cyanoprop-2-enoic acid Chemical compound OC(=O)C(=C)C#N IJVRPNIWWODHHA-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 229920002565 Polyethylene Glycol 400 Polymers 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 230000000712 assembly Effects 0.000 description 2
- 238000000429 assembly Methods 0.000 description 2
- 229940097362 cyclodextrins Drugs 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 238000012423 maintenance Methods 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- 239000003106 tissue adhesive Substances 0.000 description 2
- 229940075469 tissue adhesives Drugs 0.000 description 2
- VFTFKUDGYRBSAL-UHFFFAOYSA-N 15-crown-5 Chemical compound C1COCCOCCOCCOCCO1 VFTFKUDGYRBSAL-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 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 1
- 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 1
- JYTXVMYBYRTJTI-UHFFFAOYSA-N 2-methoxyethyl 2-cyanoprop-2-enoate Chemical compound COCCOC(=O)C(=C)C#N JYTXVMYBYRTJTI-UHFFFAOYSA-N 0.000 description 1
- HMMBJOWWRLZEMI-UHFFFAOYSA-N 4,5,6,7-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1CCCC2=C1C(=O)OC2=O HMMBJOWWRLZEMI-UHFFFAOYSA-N 0.000 description 1
- 229920001450 Alpha-Cyclodextrin Polymers 0.000 description 1
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 1
- 229920000604 Polyethylene Glycol 200 Polymers 0.000 description 1
- 229920002582 Polyethylene Glycol 600 Polymers 0.000 description 1
- 229920002593 Polyethylene Glycol 800 Polymers 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 229940043377 alpha-cyclodextrin Drugs 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 159000000032 aromatic acids Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 description 1
- 229960004853 betadex Drugs 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- GDSRMADSINPKSL-HSEONFRVSA-N gamma-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO GDSRMADSINPKSL-HSEONFRVSA-N 0.000 description 1
- 229940080345 gamma-cyclodextrin Drugs 0.000 description 1
- 239000003349 gelling agent Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M methacrylate group Chemical group C(C(=C)C)(=O)[O-] CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- RPQUGMLCZLGZTG-UHFFFAOYSA-N octyl cyanoacrylate Chemical compound CCCCCCCCOC(=O)C(=C)C#N RPQUGMLCZLGZTG-UHFFFAOYSA-N 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
- 239000005060 rubber Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 125000005415 substituted alkoxy group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- 230000009974 thixotropic effect Effects 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
- C08F222/00—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 a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/30—Nitriles
- C08F222/32—Alpha-cyano-acrylic acid; Esters thereof
- C08F222/322—Alpha-cyano-acrylic acid ethyl ester, e.g. ethyl-2-cyanoacrylate
-
- 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
- C09J167/00—Adhesives based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Adhesives based on derivatives of such polymers
- C09J167/06—Unsaturated polyesters having carbon-to-carbon unsaturation
-
- 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
- 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
- C08F220/62—Monocarboxylic acids having ten or more carbon atoms; Derivatives thereof
- C08F220/66—Anhydrides
-
- 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
- C08F222/00—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 a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/04—Anhydrides, e.g. cyclic anhydrides
- C08F222/06—Maleic anhydride
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Description
Claims (11)
- (a)アリル−2−シアノアクリレートと、
(b)芳香族酸無水物成分と、
を含む、シアノアクリレート接着剤組成物。 - 安定化する量の酸性安定剤及びフリーラジカル抑制剤を更に含む、請求項1に記載の組成物。
- H2C=C(CN)−COOR(式中、Rは、C1〜15アルキル、アルコキシアルキル、シクロアルキル、アルケニル、アラルキル、アリール及びハロアルキル基、並びにビスシアノアクリレートから選択される)の構造の範囲内の物質から選択されるシアノアクリレートモノマーを更に含む、請求項1に記載の組成物。
- カリックスアレーン、オキサカリックスアレーン、シラクラウン、シクロデキストリン、クラウンエーテル、ポリ(エチレングリコール)ジ(メタ)アクリレート、エトキシル化ヒドロキシ化合物、及びこれらの組合せからなる群から選択される促進剤成分を更に含む、請求項1に記載の組成物。
- 前記クラウンエーテルが、15−クラウン−5、18−クラウン−6、ジベンゾ−18−クラウン−6、ベンゾ−15−クラウン−5−ジベンゾ−24−クラウン−8、ジベンゾ−30−クラウン−10、トリベンゾ−18−クラウン−6、asym−ジベンゾ−22−クラウン−6、ジベンゾ−14−クラウン−4、ジシクロヘキシル−18−クラウン−6、ジシクロヘキシル−24−クラウン−8、シクロヘキシル−12−クラウン−4、1,2−デカリル−15−クラウン−5、1,2−ナフト−15−クラウン−5、3,4,5−ナフチル−16−クラウン−5、1,2−メチル−ベンゾ−18−クラウン−6、1,2−メチルベンゾ−5、6−メチルベンゾ−18−クラウン−6、1,2−t−ブチル−18−クラウン−6、1,2−ビニルベンゾ−15−クラウン−5、1,2−ビニルベンゾ−18−クラウン−6、1,2−t−ブチル−シクロヘキシル−18−クラウン−6、asym−ジベンゾ−22−クラウン−6、及び1,2−ベンゾ−1,4−ベンゾ−5−オキシゲン−20−クラウン−7、並びにこれらの組合せからなる群内の構成物質から選択される、請求項4に記載の組成物。
- 前記芳香族酸無水物成分が無水フタル酸である、請求項1に記載の組成物。
- 水素化した芳香族酸無水物成分を更に含む、請求項1に記載の組成物。
- 請求項1に記載の組成物の反応生成物。
- 二つの基材を接合する方法であって、
基材の少なくとも一つに、請求項1に記載のシアノアクリレート接着剤組成物を塗布するステップと、
接着剤を硬化させるのに十分な時間、基材を一体にするステップと、
を含む方法。 - 請求項1に記載のシアノアクリレート接着剤組成物を調製する方法であって、
アリル−2−シアノアクリレートを用意するステップと、
混合によりアリル−2−シアノアクリレートと酸無水物成分とを組み合わせるステップと、
を含む方法。 - 鋼から構成される少なくとも一つの基材を有する接着体において硬化したシアノアクリレート組成物の耐水性を向上する方法であって、
基材の少なくとも一つに、請求項1に記載のシアノアクリレート接着剤組成物を塗布するステップであって、一体にする基材の少なくとも一つが鋼から構成されるステップと、
接着剤を硬化させるのに十分な時間、基材を一体にするステップと、
を含む方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US13/838,303 US9783714B2 (en) | 2013-03-15 | 2013-03-15 | Cyanoacrylate compositions |
US13/838,303 | 2013-03-15 | ||
PCT/IB2014/000732 WO2014140798A2 (en) | 2013-03-15 | 2014-02-21 | Cyanoacrylate compositions |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2016511317A true JP2016511317A (ja) | 2016-04-14 |
JP6656927B2 JP6656927B2 (ja) | 2020-03-04 |
Family
ID=51014567
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2015562372A Active JP6656927B2 (ja) | 2013-03-15 | 2014-02-21 | シアノアクリレート組成物 |
Country Status (7)
Country | Link |
---|---|
US (1) | US9783714B2 (ja) |
EP (1) | EP2970719B1 (ja) |
JP (1) | JP6656927B2 (ja) |
KR (1) | KR102230974B1 (ja) |
CN (1) | CN105121571B (ja) |
ES (1) | ES2845623T3 (ja) |
WO (1) | WO2014140798A2 (ja) |
Cited By (2)
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JP2019501235A (ja) * | 2015-11-06 | 2019-01-17 | ヘンケル アイピー アンド ホールディング ゲゼルシャフト ミット ベシュレンクテル ハフツング | シアノアクリレート組成物 |
WO2024062865A1 (ja) * | 2022-09-20 | 2024-03-28 | 田岡化学工業株式会社 | 2-シアノアクリレート系接着剤組成物 |
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TWI672349B (zh) * | 2015-02-18 | 2019-09-21 | 日商東亞合成股份有限公司 | 2-氰基丙烯酸酯(鹽)類黏著劑組成物(三) |
GB2544272B (en) * | 2015-11-06 | 2020-02-19 | Henkel IP & Holding GmbH | Cyanoacrylate compositions |
WO2020191510A1 (en) * | 2019-03-22 | 2020-10-01 | Henkel Ag & Co. Kgaa | Cyanoacrylate adhesive composition |
CN112795318B (zh) * | 2020-12-31 | 2022-11-04 | 杭州电子科技大学 | 一种光学玻璃抛光用胶粘剂及其制备方法 |
EP4194523A1 (en) * | 2021-12-07 | 2023-06-14 | Cuantum Medical Cosmetics, S.L. | Cyanoacrylate adhesive composition |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS4922433A (ja) * | 1972-06-21 | 1974-02-27 | ||
JPS5048039A (ja) * | 1973-06-16 | 1975-04-28 | ||
JPS57501529A (ja) * | 1980-08-28 | 1982-08-26 | ||
JP2009500517A (ja) * | 2005-07-11 | 2009-01-08 | ヘンケル コーポレイション | 強靭化シアノアクリレート組成物 |
Family Cites Families (22)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IE34874B1 (en) | 1971-01-13 | 1975-09-03 | Intercontinental Chem Co Ltd | Cyanoacrylate adhesive compositions |
US4196271A (en) | 1975-12-24 | 1980-04-01 | Toagosei Chemical Industry Co., Ltd. | Adhesive composition |
US4196270A (en) | 1977-12-27 | 1980-04-01 | Ford Motor Company | High solids coating composition adapted for use as automotive topcoat-#5 |
US4490515A (en) | 1981-06-01 | 1984-12-25 | Loctite Corporation | Hot strength cyanoacrylate adhesive composition |
JPS59147067A (ja) | 1983-02-09 | 1984-08-23 | Alpha Giken:Kk | α−シアノアクリレ−ト系耐熱性瞬間接着剤組成物 |
US4906317A (en) | 1983-11-10 | 1990-03-06 | Loctite Corporation | Instant adhesive composition and bonding method employing same |
US4622414A (en) | 1984-01-27 | 1986-11-11 | Loctite Limited | Novel calixarene compounds |
US4718966A (en) | 1984-01-30 | 1988-01-12 | Loctite (Ireland) Ltd. | Bonding method utilizing cyanoacrylate adhesive having calixarene accelerator |
US4556700A (en) | 1984-01-30 | 1985-12-03 | Loctite Limited | Instant adhesive composition utilizing calixarene accelerators |
US4636539A (en) | 1984-01-30 | 1987-01-13 | Loctite (Ireland) Limited | Instant adhesive composition utilizing calixarene accelerators |
US4695615A (en) | 1984-11-21 | 1987-09-22 | Loctite (Ireland) Limited | Instant adhesive composition utilizing mixed functionality calixarenes as accelerators |
IE59509B1 (en) | 1987-01-21 | 1994-03-09 | Loctite Ireland Ltd | Functionalised oxacalixarenes, their preparation and use in instant adhesive compositions |
US4837260A (en) * | 1986-05-23 | 1989-06-06 | Toagosei Chemical Industry Co., Ltd. | Cyanoacrylate compositions |
US5135598A (en) * | 1987-08-13 | 1992-08-04 | Minnesota Mining And Manufacturing Company | Priming polymeric surfaces for cyanoacrylate adhesives |
DE4009621A1 (de) | 1990-03-26 | 1991-10-02 | Henkel Kgaa | (alpha) -cyanacrylatklebstoffzusammensetzungen |
TW359683B (en) * | 1993-12-23 | 1999-06-01 | Loctite Ireland Ltd | Sterilized cyanoacrylate adhesive composition, and a method of making such composition |
US6607632B1 (en) | 1996-08-16 | 2003-08-19 | Loctite (R&D) Limited | Cyanoacrylate adhesive compositions for bonding glass |
US7446136B2 (en) * | 2005-04-05 | 2008-11-04 | Momentive Performance Materials Inc. | Method for producing cure system, adhesive system, and electronic device |
KR101262771B1 (ko) * | 2005-05-30 | 2013-05-09 | 도아고세이가부시키가이샤 | 2-시아노아크릴레이트계 조성물 |
CN1995252B (zh) * | 2006-12-21 | 2010-05-12 | 大连轻工业学院 | 一种光固化氰基丙烯酸酯粘合剂 |
EP2511355B1 (en) * | 2011-04-12 | 2013-10-23 | Henkel Ireland Ltd. | Cyanoacrylate adhesive with improved water resistance |
CN104284955B (zh) | 2011-07-15 | 2016-10-12 | 汉高知识产权控股有限责任公司 | 氰基丙烯酸酯组合物 |
-
2013
- 2013-03-15 US US13/838,303 patent/US9783714B2/en active Active
-
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- 2014-02-21 JP JP2015562372A patent/JP6656927B2/ja active Active
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Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS4922433A (ja) * | 1972-06-21 | 1974-02-27 | ||
JPS5048039A (ja) * | 1973-06-16 | 1975-04-28 | ||
JPS57501529A (ja) * | 1980-08-28 | 1982-08-26 | ||
JP2009500517A (ja) * | 2005-07-11 | 2009-01-08 | ヘンケル コーポレイション | 強靭化シアノアクリレート組成物 |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2019501235A (ja) * | 2015-11-06 | 2019-01-17 | ヘンケル アイピー アンド ホールディング ゲゼルシャフト ミット ベシュレンクテル ハフツング | シアノアクリレート組成物 |
WO2024062865A1 (ja) * | 2022-09-20 | 2024-03-28 | 田岡化学工業株式会社 | 2-シアノアクリレート系接着剤組成物 |
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WO2014140798A3 (en) | 2014-12-11 |
KR20150129705A (ko) | 2015-11-20 |
JP6656927B2 (ja) | 2020-03-04 |
US9783714B2 (en) | 2017-10-10 |
EP2970719B1 (en) | 2020-12-09 |
CN105121571B (zh) | 2018-07-10 |
KR102230974B1 (ko) | 2021-03-24 |
CN105121571A (zh) | 2015-12-02 |
WO2014140798A2 (en) | 2014-09-18 |
ES2845623T3 (es) | 2021-07-27 |
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