JP7045329B2 - 組成物 - Google Patents
組成物 Download PDFInfo
- Publication number
- JP7045329B2 JP7045329B2 JP2018556764A JP2018556764A JP7045329B2 JP 7045329 B2 JP7045329 B2 JP 7045329B2 JP 2018556764 A JP2018556764 A JP 2018556764A JP 2018556764 A JP2018556764 A JP 2018556764A JP 7045329 B2 JP7045329 B2 JP 7045329B2
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- Prior art keywords
- acrylate
- meth
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- composition
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000000203 mixture Substances 0.000 title claims description 54
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 81
- 239000003795 chemical substances by application Substances 0.000 claims description 30
- -1 Phosphate ester Chemical class 0.000 claims description 28
- 239000000853 adhesive Substances 0.000 claims description 20
- 230000001070 adhesive effect Effects 0.000 claims description 20
- 150000003014 phosphoric acid esters Chemical class 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 16
- 229920000098 polyolefin Polymers 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 150000004292 cyclic ethers Chemical group 0.000 claims description 12
- 229910019142 PO4 Inorganic materials 0.000 claims description 9
- 239000010452 phosphate Substances 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- LRIOGIBXOOAGMT-UHFFFAOYSA-N n'-(2-aminoethyl)ethane-1,2-diamine;triethylborane Chemical compound CCB(CC)CC.NCCNCCN LRIOGIBXOOAGMT-UHFFFAOYSA-N 0.000 claims description 6
- 229920002430 Fibre-reinforced plastic Polymers 0.000 claims description 4
- 239000011151 fibre-reinforced plastic Substances 0.000 claims description 4
- SJKKMGRHBRUPIG-UHFFFAOYSA-N 3-methoxypropan-1-amine;tributylborane Chemical compound COCCCN.CCCCB(CCCC)CCCC SJKKMGRHBRUPIG-UHFFFAOYSA-N 0.000 claims description 3
- 239000004793 Polystyrene Substances 0.000 claims description 3
- 150000001925 cycloalkenes Chemical class 0.000 claims description 3
- 229920002223 polystyrene Polymers 0.000 claims description 3
- IJUCBZFJEAVADL-UHFFFAOYSA-N propane-1,3-diamine;triethylborane Chemical compound NCCCN.CCB(CC)CC IJUCBZFJEAVADL-UHFFFAOYSA-N 0.000 claims description 3
- 239000011342 resin composition Substances 0.000 claims description 3
- 239000000463 material Substances 0.000 description 17
- 239000004743 Polypropylene Substances 0.000 description 16
- 239000002253 acid Substances 0.000 description 14
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 8
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 7
- 229920001155 polypropylene Polymers 0.000 description 7
- 239000013065 commercial product Substances 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- LJKDOMVGKKPJBH-UHFFFAOYSA-N 2-ethylhexyl dihydrogen phosphate Chemical compound CCCCC(CC)COP(O)(O)=O LJKDOMVGKKPJBH-UHFFFAOYSA-N 0.000 description 4
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 4
- 230000006378 damage Effects 0.000 description 4
- 229920000049 Carbon (fiber) Polymers 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- 239000004917 carbon fiber Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 239000003522 acrylic cement Substances 0.000 description 2
- 230000001464 adherent effect Effects 0.000 description 2
- 239000012790 adhesive layer Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 238000004381 surface treatment Methods 0.000 description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- FSJSYDFBTIVUFD-SUKNRPLKSA-N (z)-4-hydroxypent-3-en-2-one;oxovanadium Chemical compound [V]=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O FSJSYDFBTIVUFD-SUKNRPLKSA-N 0.000 description 1
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- VHSHLMUCYSAUQU-UHFFFAOYSA-N 2-hydroxypropyl methacrylate Chemical compound CC(O)COC(=O)C(C)=C VHSHLMUCYSAUQU-UHFFFAOYSA-N 0.000 description 1
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 1
- DXPPIEDUBFUSEZ-UHFFFAOYSA-N 6-methylheptyl prop-2-enoate Chemical compound CC(C)CCCCCOC(=O)C=C DXPPIEDUBFUSEZ-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- JYFHYPJRHGVZDY-UHFFFAOYSA-N Dibutyl phosphate Chemical compound CCCCOP(O)(=O)OCCCC JYFHYPJRHGVZDY-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- LCXXNKZQVOXMEH-UHFFFAOYSA-N Tetrahydrofurfuryl methacrylate Chemical compound CC(=C)C(=O)OCC1CCCO1 LCXXNKZQVOXMEH-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 239000004566 building material Substances 0.000 description 1
- FJTUUPVRIANHEX-UHFFFAOYSA-N butan-1-ol;phosphoric acid Chemical compound CCCCO.OP(O)(O)=O FJTUUPVRIANHEX-UHFFFAOYSA-N 0.000 description 1
- 125000006226 butoxyethyl group Chemical group 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- YOQPKXIRWPWFIE-UHFFFAOYSA-N ctk4c8335 Chemical compound CC(=C)C(=O)OCCOP(=O)=O YOQPKXIRWPWFIE-UHFFFAOYSA-N 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 239000003479 dental cement Substances 0.000 description 1
- SEGLCEQVOFDUPX-UHFFFAOYSA-N di-(2-ethylhexyl)phosphoric acid Chemical compound CCCCC(CC)COP(O)(=O)OCC(CC)CCCC SEGLCEQVOFDUPX-UHFFFAOYSA-N 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002463 lignoceryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000012785 packaging film Substances 0.000 description 1
- 229920006280 packaging film Polymers 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000009832 plasma treatment Methods 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
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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
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- 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
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
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- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
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- C08F220/14—Methyl esters, e.g. methyl (meth)acrylate
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/521—Esters of phosphoric acids, e.g. of H3PO4
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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- C08K5/55—Boron-containing compounds
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- 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
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- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
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- 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
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- C09J133/062—Copolymers with monomers not covered by C09J133/06
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- 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
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- C08F220/12—Esters of monohydric alcohols or phenols
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- 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
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- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
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- 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
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- C08F220/20—Esters of polyhydric alcohols or phenols, e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(meth)acrylate
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
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- 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
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- 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
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- 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
- C08F220/32—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals
- C08F220/325—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals containing glycidyl radical, e.g. glycidyl (meth)acrylate
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- 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
- C08F230/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
- C08F230/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing phosphorus
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- 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
- C09J133/062—Copolymers with monomers not covered by C09J133/06
- C09J133/066—Copolymers with monomers not covered by C09J133/06 containing -OH groups
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- 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
- C09J133/062—Copolymers with monomers not covered by C09J133/06
- C09J133/068—Copolymers with monomers not covered by C09J133/06 containing glycidyl groups
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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
- C09J133/04—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
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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
- C09J133/04—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
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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
- C09J143/00—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 containing boron, silicon, phosphorus, selenium, tellurium, or a metal; Adhesives based on derivatives of such polymers
- C09J143/02—Homopolymers or copolymers of monomers containing phosphorus
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Description
<1>下記(1)~(2)を含有する組成物であり、(1-1)、(1-2)、(1-3)の含有割合が、(1)(メタ)アクリレート100質量部中、質量比で、(1-1):(1-2):(1-3)=10~90:5~80:5~80である組成物。
(1)下記(1-1)~(1-3)を含有する(メタ)アクリレート
(1-1)ヒドロキシル基を有する(メタ)アクリレート、
(1-2)アルキル(メタ)アクリレート、
(1-3)環状エーテル骨格を有する(メタ)アクリレート、
(2)有機ホウ素化合物
<2>更に、(3)リン酸エステルを含有する<1>記載の組成物。
<3>前記(3)リン酸エステルが、一般式(A)で示されるリン酸エステルである<2>記載の組成物。
<5>前記アルキルボラン-アミン錯体が、トリエチルボラン-1,3-ジアミノプロパン錯体、トリエチルボラン-ジエチレントリアミン錯体、トリブチルボラン-3-メトキシ-1-プロピルアミン錯体からなる群のうちの1種以上である<4>記載の組成物。
<6>前記(2)有機ホウ素化合物の使用量が、前記(1)(メタ)アクリレート100質量部に対して、0.01~10質量部である<1>~<5>のいずれか1項記載の組成物。
<7>前記(3)リン酸エステルの使用量が、前記(1)(メタ)アクリレート100質量部に対して、1~20質量部である<2>又は<3>記載の組成物。
<8>請求項<2>又は<3>記載の組成物を第一剤と第二剤に分け、第一剤が少なくとも(2)有機ホウ素化合物を含有し、第二剤が少なくとも(3)リン酸エステルを含有する二剤型の組成物。
<9><1>~<8>のいずれか1項記載の組成物を含む硬化性樹脂組成物。
<10><1>~<8>のいずれか1項記載の組成物を含む接着剤組成物。
<11>ポリオレフィン、シクロオレフィン、ポリスチレン、繊維強化プラスチックからなる群のうちの1種以上からなる被着体の接着に使用する<10>記載の接着剤組成物。
<12><10>又は<11>記載の接着剤組成物により接合された接合体。
ヒドロキシル基を有する(メタ)アクリレートとしては、一般式(B)で示される(メタ)アクリル系モノマーが好ましい。
アルキル(メタ)アクリレートとしては、一般式(C)で示される(メタ)アクリレートが好ましい。
環状エーテル骨格を有する(メタ)アクリレートとしては、グリシジル(メタ)アクリレート、フルフリル(メタ)アクリレート、テトラヒドロフルフリル(メタ)アクリレート、3-エチル-3-オキセタニルメチル(メタ)アクリレート、(2-メチル-エチル-1,3-ジオキソラン-4-イル)メチル(メタ)アクリレート、環状トリメチロールプロパンホルマール(メタ)アクリレート、γ-ブチロラクトン(メタ)アクリレート、ジオキソラン(メタ)アクリレート、ジオキサングリコールジ(メタ)アクリレート、オキセタン(メタ)アクリレート等が挙げられる。これらの1種以上が使用できる。環状エーテル骨格の中では、5~6員環が好ましい。環状エーテル骨格は、酸素数1を有することが好ましい。環状エーテル骨格は、炭素数2~5を有することが好ましい。環状エーテル骨格を有する(メタ)アクリレートの中では、テトラヒドロフルフリル(メタ)アクリレートが好ましい。
表1の組成にて各使用材料を混合して、第一剤と第二剤からなる接着剤組成物を調製した。結果を表1に示す。
2-ヒドロキシプロピルメタクリレート:市販品
テトラヒドロフルフリルメタアクリレート:市販品
イソオクチルアクリレート:市販品
アルキルボラン-アミン錯体:商品名「TEB-DETA」(BASF社製トリエチルボラン-ジエチレントリアミン錯体)
アルキルボラン-アミン錯体:商品名「TEB-DAP」(BASF社製トリエチルボラン-ジアミノプロパン錯体)
リン酸エステル:市販品、アシッドホスホオキシエチルメタクリレート、一般式(A)において、t=1
リン酸エステル:市販品、2-エチルヘキシルアシッドホスフェート、一般式(A)において、t=1~2
PP:ポリプロピレン試験片、市販品
CFR-PP:炭素繊維を含有するポリプロピレン試験片、市販品
JIS K-6856に従い、試験片(25mm×25mm×0.7mmt、PP)の片側に第一剤と第二剤を等量混合したものを塗布し、その後、直ちにもう1枚の試験片(25mm×25mm×2mmt、PP)を重ね合わせて貼り合わせた。その後、室温で24時間養生したものを試料とした。試料の引張せん断強度(単位:MPa)は、温度23℃、湿度50%RH環境下において、引張速度10mm/分で測定した。接着された複合材料の破壊状態として、基材と接着剤の界面での破壊を「界面破壊」とし、接着層内部の破壊を「凝集破壊」とし、基材の破壊又は破断又は降伏点を示す値を「材料破壊」とした。PPについては、4MPaで降伏点を示し、基材が伸びる状態を「材料破壊」とした。試験片と接着剤の界面の接着性が大きい点で、「材料破壊」が好ましい。
JIS K-6856に従い、試験片(25mm×25mm×0.7mmt、PP)の片側に第一剤と第二剤を等量混合したものを塗布し、その後、直ちにもう1枚の試験片(25mm×25mm×2mmt、CFR-PP)を重ね合わせて貼り合わせた。その後、室温で24時間養生したものを試料とした。試料の引張せん断強度(単位:MPa)は、温度23℃、湿度50%RH環境下において、引張速度10mm/分で測定した。接着された複合材料の破壊状態として、基材と接着剤の界面での破壊を「界面破壊」とし、接着層内部の破壊を「凝集破壊」とし、基材の破壊又は破断又は降伏点を示す値を「材料破壊」とした。試験片と接着剤の界面の接着性が大きい点で、「材料破壊」が好ましい。
表2の組成にしたこと以外は実施例1と同様にして接着剤組成物を作製し、評価を行った。結果を表2に示す。
クメンハイドロパーオキサイド:市販品
バナジルアセチルアセトネート:市販品
Claims (10)
- 下記(1)~(3)を含有する組成物であり、(1-1)、(1-2)、(1-3)の含有割合が、(1)(メタ)アクリレート100質量部中、質量比で、(1-1):(1-2):(1-3)=20~60:10~50:10~50であり、
(3)成分の含有量が、(1)成分100質量部に対して、1~20質量部である組成物。
(1)下記(1-1)~(1-3)を含有する(メタ)アクリレート
(1-1)ヒドロキシル基を有する(メタ)アクリレート、
(1-2)アルキル(メタ)アクリレート、
(1-3)環状エーテル骨格を有する(メタ)アクリレート、
(2)アルキルボラン-アミン錯体である有機ホウ素化合物
(3)リン酸エステル - 前記アルキルボラン-アミン錯体が、トリエチルボラン-1,3-ジアミノプロパン錯体、トリエチルボラン-ジエチレントリアミン錯体、トリブチルボラン-3-メトキシ-1-プロピルアミン錯体からなる群のうちの1種以上である請求項1又は2記載の組成物。
- 前記(2)有機ホウ素化合物の使用量が、前記(1)(メタ)アクリレート100質量部に対して、0.01~10質量部である請求項1~3のいずれか1項記載の組成物。
- 請求項1~4のいずれか1項記載の組成物を第一剤と第二剤に分け、前記第一剤が少なくとも前記(2)有機ホウ素化合物を含有し、前記第二剤が少なくとも前記(3)リン酸エステルを含有する二剤型の組成物。
- 請求項1~5のいずれか1項記載の組成物を含む硬化性樹脂組成物。
- 請求項1~5のいずれか1項記載の組成物を含む接着剤組成物。
- ポリオレフィン、シクロオレフィン、ポリスチレン、繊維強化プラスチックからなる群のうちの1種以上からなる被着体の接着に使用する請求項7記載の接着剤組成物。
- 請求項7又は8記載の接着剤組成物により接合された接合体。
- (1)(メタ)アクリレート100質量部中、質量比で、(1-1):(1-2):(1-3)=30~50:20~40:20~40である請求項1~5のいずれか1項記載の組成物。
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US20210261700A1 (en) * | 2018-06-15 | 2021-08-26 | Denka Company Limited | Composition |
JP7133395B2 (ja) * | 2018-08-27 | 2022-09-08 | デンカ株式会社 | 硬化性組成物 |
WO2021033628A1 (ja) * | 2019-08-22 | 2021-02-25 | デンカ株式会社 | 組成物 |
WO2022106722A1 (en) * | 2020-11-23 | 2022-05-27 | Zephyros, Inc. | Acrylate structural adhesive free of mma |
WO2023175033A1 (en) | 2022-03-17 | 2023-09-21 | Zephyros, Inc. | Autonomously curable and foamable two-component acrylic adhesive |
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