JP7394755B2 - 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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- JP7394755B2 JP7394755B2 JP2020523363A JP2020523363A JP7394755B2 JP 7394755 B2 JP7394755 B2 JP 7394755B2 JP 2020523363 A JP2020523363 A JP 2020523363A JP 2020523363 A JP2020523363 A JP 2020523363A JP 7394755 B2 JP7394755 B2 JP 7394755B2
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- Prior art keywords
- crown
- cyanoacrylate
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- 229920001651 Cyanoacrylate Polymers 0.000 title claims description 65
- 239000000203 mixture Substances 0.000 title claims description 60
- MWCLLHOVUTZFKS-UHFFFAOYSA-N Methyl cyanoacrylate Chemical compound COC(=O)C(=C)C#N MWCLLHOVUTZFKS-UHFFFAOYSA-N 0.000 title claims description 45
- 239000000758 substrate Substances 0.000 claims description 15
- 229920001971 elastomer Polymers 0.000 claims description 13
- -1 polyethylene Polymers 0.000 claims description 13
- 230000003014 reinforcing effect Effects 0.000 claims description 13
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 12
- 239000007795 chemical reaction product Substances 0.000 claims description 12
- 239000000178 monomer Substances 0.000 claims description 11
- JJJFUHOGVZWXNQ-UHFFFAOYSA-N enbucrilate Chemical compound CCCCOC(=O)C(=C)C#N JJJFUHOGVZWXNQ-UHFFFAOYSA-N 0.000 claims description 10
- 229950010048 enbucrilate Drugs 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- RPQUGMLCZLGZTG-UHFFFAOYSA-N octyl cyanoacrylate Chemical compound CCCCCCCCOC(=O)C(=C)C#N RPQUGMLCZLGZTG-UHFFFAOYSA-N 0.000 claims description 10
- 239000002245 particle Substances 0.000 claims description 9
- 239000002318 adhesion promoter Substances 0.000 claims description 8
- 229920001577 copolymer Polymers 0.000 claims description 8
- 230000004048 modification Effects 0.000 claims description 7
- 238000012986 modification Methods 0.000 claims description 7
- 229920001223 polyethylene glycol Polymers 0.000 claims description 7
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 6
- 239000005977 Ethylene Substances 0.000 claims description 6
- VTJUKNSKBAOEHE-UHFFFAOYSA-N calixarene Chemical group 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 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid group Chemical group C(CC(O)(C(=O)O)CC(=O)O)(=O)O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 6
- 239000003381 stabilizer Substances 0.000 claims description 6
- JYTXVMYBYRTJTI-UHFFFAOYSA-N 2-methoxyethyl 2-cyanoprop-2-enoate Chemical group COCCOC(=O)C(=C)C#N JYTXVMYBYRTJTI-UHFFFAOYSA-N 0.000 claims description 4
- 229920000858 Cyclodextrin Polymers 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
- 150000003983 crown ethers Chemical class 0.000 claims description 4
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 claims description 3
- 150000003254 radicals Chemical class 0.000 claims description 3
- VFTFKUDGYRBSAL-UHFFFAOYSA-N 15-crown-5 Chemical compound C1COCCOCCOCCOCCO1 VFTFKUDGYRBSAL-UHFFFAOYSA-N 0.000 claims description 2
- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-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
- 239000004698 Polyethylene Substances 0.000 claims description 2
- 239000002202 Polyethylene glycol Substances 0.000 claims description 2
- 235000021355 Stearic acid Nutrition 0.000 claims description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- 239000003963 antioxidant agent Substances 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
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 2
- 239000003349 gelling agent Substances 0.000 claims description 2
- 239000006082 mold release agent Substances 0.000 claims description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 2
- 230000003647 oxidation Effects 0.000 claims description 2
- 238000007254 oxidation reaction Methods 0.000 claims description 2
- 229920000573 polyethylene Polymers 0.000 claims description 2
- 229920002689 polyvinyl acetate Polymers 0.000 claims description 2
- 239000011118 polyvinyl acetate Substances 0.000 claims description 2
- 239000008117 stearic acid Substances 0.000 claims description 2
- 239000002562 thickening agent Substances 0.000 claims description 2
- 239000013008 thixotropic agent Substances 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- IQDPHMACOQAPBQ-UHFFFAOYSA-N 2-ethoxyethyl 2-cyanoprop-2-enoate Chemical compound CCOCCOC(=O)C(=C)C#N IQDPHMACOQAPBQ-UHFFFAOYSA-N 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- 239000000463 material Substances 0.000 claims 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 claims 1
- 230000000087 stabilizing effect Effects 0.000 claims 1
- 239000001993 wax Substances 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 description 8
- 235000019645 odor Nutrition 0.000 description 8
- 239000000047 product Substances 0.000 description 6
- 229910001209 Low-carbon steel Inorganic materials 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- FGBJXOREULPLGL-UHFFFAOYSA-N ethyl cyanoacrylate Chemical compound CCOC(=O)C(=C)C#N FGBJXOREULPLGL-UHFFFAOYSA-N 0.000 description 5
- 239000000654 additive Substances 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- FTWUCRJPVZMPMC-UHFFFAOYSA-N 2-cyano-5-methoxypent-2-enoic acid Chemical compound COCCC=C(C#N)C(O)=O FTWUCRJPVZMPMC-UHFFFAOYSA-N 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 229940097362 cyclodextrins Drugs 0.000 description 3
- 229940053009 ethyl cyanoacrylate Drugs 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 101710185544 Maltose-binding periplasmic protein Proteins 0.000 description 2
- 101710175625 Maltose/maltodextrin-binding periplasmic protein Proteins 0.000 description 2
- 101710144262 Maltotriose-binding protein Proteins 0.000 description 2
- 229920002565 Polyethylene Glycol 400 Polymers 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 238000012423 maintenance Methods 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
- 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
- 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
- PZDAQXOVRYIDIP-UHFFFAOYSA-N 2-cyano-4-ethoxybut-2-enoic acid Chemical compound CCOCC=C(C#N)C(O)=O PZDAQXOVRYIDIP-UHFFFAOYSA-N 0.000 description 1
- DIJIUOOEUMDTPT-UHFFFAOYSA-N 2-cyano-5-ethoxypent-2-enoic acid Chemical compound CCOCCC=C(C#N)C(O)=O DIJIUOOEUMDTPT-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
- 239000004830 Super Glue Substances 0.000 description 1
- 239000004699 Ultra-high molecular weight polyethylene Substances 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 229920000800 acrylic rubber Polymers 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- DQXBYHZEEUGOBF-UHFFFAOYSA-N but-3-enoic acid;ethene Chemical compound C=C.OC(=O)CC=C DQXBYHZEEUGOBF-UHFFFAOYSA-N 0.000 description 1
- 150000007942 carboxylates Chemical group 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 229920001198 elastomeric copolymer Polymers 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- VKLYZBPBDRELST-UHFFFAOYSA-N ethene;methyl 2-methylprop-2-enoate Chemical compound C=C.COC(=O)C(C)=C VKLYZBPBDRELST-UHFFFAOYSA-N 0.000 description 1
- 239000005038 ethylene vinyl acetate Substances 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000013011 mating Effects 0.000 description 1
- 239000011159 matrix material 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
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 239000002052 molecular layer Substances 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920006112 polar polymer Polymers 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 239000000843 powder Substances 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
- ZTYMNUBYYQNBFP-UHFFFAOYSA-N propyl 2-cyanoprop-2-enoate Chemical compound CCCOC(=O)C(=C)C#N ZTYMNUBYYQNBFP-UHFFFAOYSA-N 0.000 description 1
- 239000012758 reinforcing additive Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000005415 substituted alkoxy group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 230000009974 thixotropic effect Effects 0.000 description 1
- 229920000785 ultra high molecular weight polyethylene Polymers 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
- C09J4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C65/00—Joining or sealing of preformed parts, e.g. welding of plastics materials; Apparatus therefor
- B29C65/48—Joining or sealing of preformed parts, e.g. welding of plastics materials; Apparatus therefor using adhesives, i.e. using supplementary joining material; solvent bonding
- B29C65/4805—Joining or sealing of preformed parts, e.g. welding of plastics materials; Apparatus therefor using adhesives, i.e. using supplementary joining material; solvent bonding characterised by the type of adhesives
- B29C65/483—Reactive adhesives, e.g. chemically curing adhesives
- B29C65/484—Moisture curing adhesives
-
- 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
- C08F22/00—Homopolymers and 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
- C08F22/30—Nitriles
- C08F22/32—Alpha-cyano-acrylic acid; Esters thereof
-
- 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
- C08F222/327—Alpha-cyano-acrylic acid alkoxy ester
-
- 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
- C08F255/00—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00
- C08F255/02—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00 on to polymers of olefins having two or three carbon atoms
-
- 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
- C08F291/00—Macromolecular compounds obtained by polymerising monomers on to macromolecular compounds according to more than one of the groups C08F251/00 - C08F289/00
- C08F291/02—Macromolecular compounds obtained by polymerising monomers on to macromolecular compounds according to more than one of the groups C08F251/00 - C08F289/00 on to elastomers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or 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 of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/18—Homopolymers or copolymers of nitriles
- C08L33/22—Homopolymers or copolymers of nitriles containing four or more carbon atoms
-
- 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
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/08—Macromolecular additives
-
- 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
- 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
- C09J133/18—Homopolymers or copolymers of nitriles
- C09J133/22—Homopolymers or copolymers of nitriles containing four or more carbon atoms
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- 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
- C09J135/00—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 a carboxyl radical, and containing at least another carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J135/04—Homopolymers or copolymers of nitriles
-
- 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
- C08F222/324—Alpha-cyano-acrylic acid butyl ester
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or 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 of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
- C08L33/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or 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 of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/18—Homopolymers or copolymers of nitriles
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- 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
- C09J133/18—Homopolymers or copolymers of nitriles
Description
シアノアクリレート接着剤組成物は周知であり、多種多様な用途をもつ、短時間で硬化する瞬間接着剤として広範に使用される。H.V.Coover、D.W.Dreifus及びJ.T.O’Connor、「Cyanoacrylate Adhesives」Handbook of Adhesives中、27、463~77、I.Skeist編、Van Nostrand Reinhold、New York、第3版(1990)を参照のこと。G.H.Millet、「Cyanoacrylate Adhesives」Structural Adhesives:Chemistry and Technology中、S.R.Hartshorn編、Plenun Press、New York、249~307ページ(1986)も参照のこと。
上述のように、本発明は、(a)β-アルコキシアルキルシアノアクリレート成分、(b)ブチルシアノアクリレート、オクチルシアノアクリレートおよびそれらの組み合わせから選択されるシアノアクリレート成分、(c)ゴム強化成分、(d)表面修飾成分および(e)接着促進剤を含むシアノアクリレート組成物に関する。
表面エネルギー:55+ dynes/cm(水濡れ性)
比重:0.93~0.94
かさ密度:20~31lb./ft3(0.32~0.50g/cc)
分子量:3,000,000~5,000,000
たとえば、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-メチレンベンゾ-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および1,2-ベンゾ-1,4-ベンゾ-5-オキシジェン-20-クラウン-7のいずれかを用いることができる。米国特許第4,837,260号(Sato)を参照し、これにより、その開示が参照によって本明細書に明確に組み込まれる。
式中、
nは3より大きく、例えば3~12の範囲内であり、nは9であることが特に望ましい。 より具体的な例として、PEG 200 DMA(nは約4)、PEG 400 DMA(nは約9)、PEG 600 DMA(nは約14)、PEG 800 DMA(nは約19)が挙げられ、ここで、数値(例えば400)は、二つのメタクリレート基を除外した当該分子のグリコール部分の平均分子量を、グラム/モル(すなわち、400g/mol)で表記したものである。特に望ましいPEG DMAはPEG 400 DMAである。
式中、Cmは、直鎖または分枝アルキルまたはアルケニル鎖であることができ、mは1~30の整数であり、例えば5~20であり、nは2~30の整数であり、例えば5~15であり、RはHまたはアルキル、例えばC1-6アルキルであってもよい。
Claims (17)
- (a)β-アルコキシアルキルシアノアクリレート成分、
(b)ブチルシアノアクリレート、オクチルシアノアクリレートおよびそれらの組み合わせからなる群から選択されるシアノアクリレート成分、
(c)(i)エチレン、メチルアクリレートおよびカルボン酸硬化部位を有するモノマーの組み合わせの反応生成物、(ii)エチレンおよびメチルアクリレートのジポリマー、(iii)塩化ビニリデン-アクリロニトリルコポリマー、(iv)塩化ビニル/ビニルアセテートコポリマー、(v)ポリエチレンとポリビニルアセテートのコポリマー、およびそれらの組み合わせからなる群から選択されるゴム強化成分、
(d)表面修飾成分および
(e)接着促進剤を含み、
β-アルコキシアルキルシアノアクリレート成分(a)が、組成物の総重量に基づいて55重量%~85重量%の量で存在し、シアノアクリレート成分(b)が5~30重量%の量で存在するシアノアクリレート組成物。 - β-アルコキシアルキルシアノアクリレート成分(a)およびシアノアクリレート成分(b)が70:30の重量比で存在し、表面修飾成分(d)が、最表面の酸化により表面が修飾された、平均粒子径が500μm以下の粒子状のポリオレフィンであり、接着促進剤(e)は、リン酸または無水イタコン酸の少なくとも一方である、請求項1に記載の組成物。
- β-アルコキシアルキルシアノアクリレート成分が、β-メトキシエチルシアノアクリレート、β-エトキシエチルシアノアクリレート、およびそれらの組み合わせから選択される、請求項1または2に記載の組成物。
- ゴム強化成分が、エチレン、メチルアクリレートおよびカルボン酸硬化部位を有するモノマーの組み合わせの反応生成物であり、反応生成物が離型剤、酸化防止剤、ステアリン酸、ポリエチレングリコールエーテルワックスを含まない、請求項1~3のいずれか1項に記載の組成物。
- チキソトロープ剤、ゲル化剤、増粘剤、促進剤および耐衝撃性付与剤のうちの1以上をさらに含む、請求項1~4のいずれか1項に記載の組成物。
- 促進剤が、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、エトキシル化水酸基化合物、およびこれらの組み合わせからなる群から選択される、請求項5に記載の組成物。
- カリックスアレーンが、テトラブチルテトラ[2-エトキシ-2-オキソエトキシ]カリックス-4-アレーンである、請求項6に記載の組成物。
- 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、および1,2-ベンゾ-1,4-ベンゾ-5-オキシジェン-20-クラウン-7およびそれらの組み合わせからなる群内のメンバーから選択される、請求項6に記載の組成物。
- 耐衝撃性付与剤が、クエン酸である、請求項5に記載の組成物。
- β-アルコキシアルキルシアノアクリレート成分(a)およびシアノアクリレート成分(b)が、組成物中に55~75:20~30の範囲の重量比で存在する、請求項1~10のいずれか1項に記載の組成物。
- β-アルコキシアルキルシアノアクリレート成分(a)が、組成物の総重量に基づいて55重量%~80重量%の量で存在し、シアノアクリレート成分が7重量%~27重量%の量で存在する、請求項1~11のいずれか1項に記載の組成物。
- β-アルコキシアルキルシアノアクリレート成分(a)およびシアノアクリレート成分(b)が、組成物中に70:30の範囲の重量比で存在する、請求項1~12のいずれか1項に記載の組成物。
- 安定化量の酸性安定剤およびフリーラジカル阻害剤をさらに含む、請求項1~13のいずれか1項に記載の組成物。
- 請求項1~14のいずれか1項に記載の組成物の反応生成物。
- 請求項1~14のいずれか1項に記載のシアノアクリレート組成物を少なくとも1つの基材に塗布し、組成物を固定するのに十分な時間、基材を互いに合わせる工程を含む、2つの基材を結合する方法。
- ブチルシアノアクリレート、オクチルシアノアクリレートおよびそれらの組み合わせからなる群から選択されるシアノアクリレート成分に溶解したゴム強化成分を提供する工程と、β-アルコキシアルキルシアノアクリレート成分、表面修飾成分および接着促進剤を混合し、それらと混ぜ合わせる工程を含む、請求項1~14のいずれか1項に記載のシアノアクリレート組成物の調製方法。
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PCT/EP2018/079498 WO2019081762A1 (en) | 2017-10-27 | 2018-10-26 | CYANOACRYLATE COMPOSITIONS |
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JP2004522827A (ja) | 2001-01-08 | 2004-07-29 | ロックタイト (アール アンド ディー) リミテッド | 柔軟なポリマー材料に硬化可能なシアノアクリレート組成物 |
JP2006527782A (ja) | 2003-06-18 | 2006-12-07 | ロックタイト (アール アンド ディー) リミテッド | シアノアクリレート組成物 |
WO2010029134A1 (en) | 2008-09-10 | 2010-03-18 | Loctite (R&D) Limited | Toughened cyanoacrylate compositions |
JP2010150422A (ja) | 2008-12-25 | 2010-07-08 | Toagosei Co Ltd | 接着剤組成物 |
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US20200255706A1 (en) | 2020-08-13 |
GB2567868A (en) | 2019-05-01 |
EP3700951A1 (en) | 2020-09-02 |
US11299652B2 (en) | 2022-04-12 |
JP2021500453A (ja) | 2021-01-07 |
KR20200076680A (ko) | 2020-06-29 |
WO2019081762A1 (en) | 2019-05-02 |
GB201717708D0 (en) | 2017-12-13 |
GB2567868B (en) | 2020-05-06 |
CN111263778A (zh) | 2020-06-09 |
CN111263778B (zh) | 2022-08-30 |
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