CN113557275A - 两部分可固化组合物 - Google Patents
两部分可固化组合物 Download PDFInfo
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- CN113557275A CN113557275A CN202080022293.7A CN202080022293A CN113557275A CN 113557275 A CN113557275 A CN 113557275A CN 202080022293 A CN202080022293 A CN 202080022293A CN 113557275 A CN113557275 A CN 113557275A
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- 229910052723 transition metal Inorganic materials 0.000 claims abstract description 23
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- 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 claims 1
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- YSSSPARMOAYJTE-UHFFFAOYSA-N dibenzo-18-crown-6 Chemical compound O1CCOCCOC2=CC=CC=C2OCCOCCOC2=CC=CC=C21 YSSSPARMOAYJTE-UHFFFAOYSA-N 0.000 description 2
- 239000005038 ethylene vinyl acetate Substances 0.000 description 2
- ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 description 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
- RKVIEVIJBJXOFV-UHFFFAOYSA-N hexan-2-yl 2-cyanoprop-2-enoate Chemical compound CCCCC(C)OC(=O)C(=C)C#N RKVIEVIJBJXOFV-UHFFFAOYSA-N 0.000 description 2
- XDZLHTBOHLGGCJ-UHFFFAOYSA-N hexyl 2-cyanoprop-2-enoate Chemical compound CCCCCCOC(=O)C(=C)C#N XDZLHTBOHLGGCJ-UHFFFAOYSA-N 0.000 description 2
- 229910002011 hydrophilic fumed silica Inorganic materials 0.000 description 2
- 229920002681 hypalon Polymers 0.000 description 2
- QRWOVIRDHQJFDB-UHFFFAOYSA-N isobutyl cyanoacrylate Chemical compound CC(C)COC(=O)C(=C)C#N QRWOVIRDHQJFDB-UHFFFAOYSA-N 0.000 description 2
- 235000014655 lactic acid Nutrition 0.000 description 2
- 239000004310 lactic acid Substances 0.000 description 2
- 150000007517 lewis acids Chemical class 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
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- 229920003052 natural elastomer Polymers 0.000 description 2
- 229920001194 natural rubber Polymers 0.000 description 2
- FZUGPQWGEGAKET-UHFFFAOYSA-N parbenate Chemical compound CCOC(=O)C1=CC=C(N(C)C)C=C1 FZUGPQWGEGAKET-UHFFFAOYSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- SBPXGLQYUALAQV-UHFFFAOYSA-N pentan-2-yl 2-cyanoprop-2-enoate Chemical compound CCCC(C)OC(=O)C(=C)C#N SBPXGLQYUALAQV-UHFFFAOYSA-N 0.000 description 2
- CMYFXTNUSQPQNH-UHFFFAOYSA-N pentan-3-yl 2-cyanoprop-2-enoate Chemical compound CCC(CC)OC(=O)C(=C)C#N CMYFXTNUSQPQNH-UHFFFAOYSA-N 0.000 description 2
- SXRFXXNXVPFXDU-UHFFFAOYSA-N pentyl 2-cyanoprop-2-enoate Chemical compound CCCCCOC(=O)C(=C)C#N SXRFXXNXVPFXDU-UHFFFAOYSA-N 0.000 description 2
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 2
- 229920000058 polyacrylate Polymers 0.000 description 2
- 229920002239 polyacrylonitrile Polymers 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 229920001610 polycaprolactone Polymers 0.000 description 2
- 239000004632 polycaprolactone Substances 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 229920001195 polyisoprene Polymers 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 238000003825 pressing Methods 0.000 description 2
- ZTYMNUBYYQNBFP-UHFFFAOYSA-N propyl 2-cyanoprop-2-enoate Chemical compound CCCOC(=O)C(=C)C#N ZTYMNUBYYQNBFP-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229920003051 synthetic elastomer Polymers 0.000 description 2
- 239000005061 synthetic rubber Substances 0.000 description 2
- QOZPAYSTKGZHHF-UHFFFAOYSA-N tert-butyl 2-cyanoprop-2-enoate Chemical compound CC(C)(C)OC(=O)C(=C)C#N QOZPAYSTKGZHHF-UHFFFAOYSA-N 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 2
- 230000008719 thickening Effects 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 2
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 2
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- MLIREBYILWEBDM-UHFFFAOYSA-M 2-cyanoacetate Chemical group [O-]C(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-M 0.000 description 1
- IQDPHMACOQAPBQ-UHFFFAOYSA-N 2-ethoxyethyl 2-cyanoprop-2-enoate Chemical compound CCOCCOC(=O)C(=C)C#N IQDPHMACOQAPBQ-UHFFFAOYSA-N 0.000 description 1
- FWWXYLGCHHIKNY-UHFFFAOYSA-N 2-ethoxyethyl prop-2-enoate Chemical compound CCOCCOC(=O)C=C FWWXYLGCHHIKNY-UHFFFAOYSA-N 0.000 description 1
- 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
- 239000004819 Drying adhesive Substances 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 238000006957 Michael reaction Methods 0.000 description 1
- 239000004825 One-part adhesive Substances 0.000 description 1
- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical group CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 description 1
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- BYBIRLURVZSVME-UHFFFAOYSA-M benzene;copper(1+);trifluoromethanesulfonate Chemical compound [Cu+].C1=CC=CC=C1.[O-]S(=O)(=O)C(F)(F)F BYBIRLURVZSVME-UHFFFAOYSA-M 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- YGNHVMNLOAYHEK-UHFFFAOYSA-M copper(1+);toluene;trifluoromethanesulfonate Chemical compound [Cu+].CC1=CC=CC=C1.[O-]S(=O)(=O)C(F)(F)F YGNHVMNLOAYHEK-UHFFFAOYSA-M 0.000 description 1
- SBTSVTLGWRLWOD-UHFFFAOYSA-L copper(ii) triflate Chemical compound [Cu+2].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F SBTSVTLGWRLWOD-UHFFFAOYSA-L 0.000 description 1
- ILRMPAUJTPZAIQ-UHFFFAOYSA-N cyclohexyl 2-cyanoprop-2-enoate Chemical compound N#CC(=C)C(=O)OC1CCCCC1 ILRMPAUJTPZAIQ-UHFFFAOYSA-N 0.000 description 1
- KWKVJEUILVQMRR-UHFFFAOYSA-N decyl 2-cyanoprop-2-enoate Chemical compound CCCCCCCCCCOC(=O)C(=C)C#N KWKVJEUILVQMRR-UHFFFAOYSA-N 0.000 description 1
- LFJLAWZRNOKTDN-UHFFFAOYSA-N dodecyl 2-cyanoprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(=C)C#N LFJLAWZRNOKTDN-UHFFFAOYSA-N 0.000 description 1
- 230000005670 electromagnetic radiation Effects 0.000 description 1
- 229940053009 ethyl cyanoacrylate Drugs 0.000 description 1
- 229920002313 fluoropolymer Polymers 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- RLCWYHSDGLVOBG-UHFFFAOYSA-N heptan-2-yl 2-cyanoprop-2-enoate Chemical compound CCCCCC(C)OC(=O)C(=C)C#N RLCWYHSDGLVOBG-UHFFFAOYSA-N 0.000 description 1
- WVXQYJXDTJWWEA-UHFFFAOYSA-N heptyl 2-cyanoprop-2-enoate Chemical compound CCCCCCCOC(=O)C(=C)C#N WVXQYJXDTJWWEA-UHFFFAOYSA-N 0.000 description 1
- 150000004687 hexahydrates Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- WRIRWRKPLXCTFD-UHFFFAOYSA-N malonamide Chemical compound NC(=O)CC(N)=O WRIRWRKPLXCTFD-UHFFFAOYSA-N 0.000 description 1
- 230000013011 mating Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- GQCBFHBKISYEQQ-UHFFFAOYSA-N nonyl 2-cyanoprop-2-enoate Chemical compound CCCCCCCCCOC(=O)C(=C)C#N GQCBFHBKISYEQQ-UHFFFAOYSA-N 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- NLYHUEGZLIXVQU-UHFFFAOYSA-N octan-4-yl 2-cyanoprop-2-enoate Chemical compound CCCCC(CCC)OC(=O)C(=C)C#N NLYHUEGZLIXVQU-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000003878 thermal aging Methods 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- GCSWIIQKEVHVMJ-UHFFFAOYSA-N undecyl 2-cyanoprop-2-enoate Chemical compound CCCCCCCCCCCOC(=O)C(=C)C#N GCSWIIQKEVHVMJ-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 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
- 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
- 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
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
- C08F220/281—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing only one oxygen, e.g. furfuryl (meth)acrylate or 2-methoxyethyl (meth)acrylate
-
- 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
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K13/00—Use of mixtures of ingredients not covered by one single of the preceding main groups, each of these compounds being essential
- C08K13/02—Organic and inorganic ingredients
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerisation Methods In General (AREA)
Abstract
Description
实施例 | 零间隙MS拉伸剪切(MPa) | 在150℃下3天后的零间隙MS拉伸剪切(MPa) |
组合物1 | 7 | 7 |
组合物2 | 7 | 12 |
组合物3 | 13 | 9 |
Claims (19)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP19305335.2 | 2019-03-19 | ||
EP19305335 | 2019-03-19 | ||
PCT/EP2020/057385 WO2020187964A1 (en) | 2019-03-19 | 2020-03-18 | Two-part curable composition |
Publications (2)
Publication Number | Publication Date |
---|---|
CN113557275A true CN113557275A (zh) | 2021-10-26 |
CN113557275B CN113557275B (zh) | 2024-04-02 |
Family
ID=66102589
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN202080022293.7A Active CN113557275B (zh) | 2019-03-19 | 2020-03-18 | 两部分可固化组合物 |
Country Status (6)
Country | Link |
---|---|
US (1) | US11939493B2 (zh) |
EP (1) | EP3941988A1 (zh) |
JP (1) | JP7496370B2 (zh) |
CN (1) | CN113557275B (zh) |
MX (1) | MX2021010878A (zh) |
WO (1) | WO2020187964A1 (zh) |
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JPH06145606A (ja) * | 1992-11-11 | 1994-05-27 | Toagosei Chem Ind Co Ltd | シアノアクリレート系接着剤組成物 |
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US20030134973A1 (en) * | 2002-01-15 | 2003-07-17 | Chen Robert Gow-Sheng | Waterborne latexes for anti-corrosive and solvent-resistant coating compositions |
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- 2020-03-18 WO PCT/EP2020/057385 patent/WO2020187964A1/en unknown
- 2020-03-18 JP JP2021556282A patent/JP7496370B2/ja active Active
- 2020-03-18 EP EP20711180.8A patent/EP3941988A1/en active Pending
- 2020-03-18 MX MX2021010878A patent/MX2021010878A/es unknown
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US20120157610A1 (en) * | 2010-12-15 | 2012-06-21 | Eastman Chemical Company | Acetoacetate-functional monomers and their uses in coating compositions |
CN104520396A (zh) * | 2012-01-23 | 2015-04-15 | 汉高知识产权控股有限责任公司 | 双组分氰基丙烯酸酯/可自由基固化粘合剂体系 |
CN104927680A (zh) * | 2014-03-17 | 2015-09-23 | 宁波百仕高联合工业有限公司 | 一种快固瞬间胶及其制备方法 |
WO2017202698A1 (en) * | 2016-05-23 | 2017-11-30 | Henkel IP & Holding GmbH | Two-part cyanoacrylate curable adhesive system |
CN109476874A (zh) * | 2016-05-23 | 2019-03-15 | 汉高知识产权控股有限责任公司 | 双组分氰基丙烯酸酯可固化粘合剂体系 |
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CN113557275B (zh) | 2024-04-02 |
WO2020187964A1 (en) | 2020-09-24 |
JP7496370B2 (ja) | 2024-06-06 |
MX2021010878A (es) | 2022-01-19 |
US11939493B2 (en) | 2024-03-26 |
JP2022525641A (ja) | 2022-05-18 |
US20220177747A1 (en) | 2022-06-09 |
EP3941988A1 (en) | 2022-01-26 |
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