JP2022517175A - 遅延添加剤を含む接着剤組成物 - Google Patents
遅延添加剤を含む接着剤組成物 Download PDFInfo
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- JP2022517175A JP2022517175A JP2021535725A JP2021535725A JP2022517175A JP 2022517175 A JP2022517175 A JP 2022517175A JP 2021535725 A JP2021535725 A JP 2021535725A JP 2021535725 A JP2021535725 A JP 2021535725A JP 2022517175 A JP2022517175 A JP 2022517175A
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- adhesive composition
- secondary amine
- methacrylate
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- 239000000203 mixture Substances 0.000 title claims abstract description 51
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 44
- 239000000853 adhesive Substances 0.000 title claims abstract description 41
- 239000000654 additive Substances 0.000 title claims abstract description 18
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- 230000003197 catalytic effect Effects 0.000 claims abstract description 7
- 150000003335 secondary amines Chemical class 0.000 claims description 13
- ZNRLMGFXSPUZNR-UHFFFAOYSA-N 2,2,4-trimethyl-1h-quinoline Chemical compound C1=CC=C2C(C)=CC(C)(C)NC2=C1 ZNRLMGFXSPUZNR-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 150000004982 aromatic amines Chemical group 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
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- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
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- COCLLEMEIJQBAG-UHFFFAOYSA-N 8-methylnonyl 2-methylprop-2-enoate Chemical compound CC(C)CCCCCCCOC(=O)C(C)=C COCLLEMEIJQBAG-UHFFFAOYSA-N 0.000 description 2
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- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
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- IAXXETNIOYFMLW-COPLHBTASA-N [(1s,3s,4s)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl] 2-methylprop-2-enoate Chemical compound C1C[C@]2(C)[C@@H](OC(=O)C(=C)C)C[C@H]1C2(C)C IAXXETNIOYFMLW-COPLHBTASA-N 0.000 description 2
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- XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 description 2
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 2
- 229920001400 block copolymer Polymers 0.000 description 2
- 239000004918 carbon fiber reinforced polymer Substances 0.000 description 2
- OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 0.000 description 2
- KBLWLMPSVYBVDK-UHFFFAOYSA-N cyclohexyl prop-2-enoate Chemical compound C=CC(=O)OC1CCCCC1 KBLWLMPSVYBVDK-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
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- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
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- 238000006116 polymerization reaction Methods 0.000 description 2
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- CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 description 2
- QEQBMZQFDDDTPN-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy benzenecarboperoxoate Chemical compound CC(C)(C)OOOC(=O)C1=CC=CC=C1 QEQBMZQFDDDTPN-UHFFFAOYSA-N 0.000 description 1
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- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- OIALIKXMLIAOSN-UHFFFAOYSA-N 2-Propylpyridine Chemical compound CCCC1=CC=CC=N1 OIALIKXMLIAOSN-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
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- 239000002841 Lewis acid Substances 0.000 description 1
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- 125000005396 acrylic acid ester group Chemical group 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
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- 125000003158 alcohol group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
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- 150000001412 amines Chemical class 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- QUZSUMLPWDHKCJ-UHFFFAOYSA-N bisphenol A dimethacrylate Chemical class C1=CC(OC(=O)C(=C)C)=CC=C1C(C)(C)C1=CC=C(OC(=O)C(C)=C)C=C1 QUZSUMLPWDHKCJ-UHFFFAOYSA-N 0.000 description 1
- VZIBAPMSKYQDFH-UHFFFAOYSA-N buta-1,3-diene;2-methylprop-2-enoic acid;prop-2-enenitrile;styrene Chemical compound C=CC=C.C=CC#N.CC(=C)C(O)=O.C=CC1=CC=CC=C1 VZIBAPMSKYQDFH-UHFFFAOYSA-N 0.000 description 1
- LKAVYBZHOYOUSX-UHFFFAOYSA-N buta-1,3-diene;2-methylprop-2-enoic acid;styrene Chemical compound C=CC=C.CC(=C)C(O)=O.C=CC1=CC=CC=C1 LKAVYBZHOYOUSX-UHFFFAOYSA-N 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
- 229940095259 butylated hydroxytoluene Drugs 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
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- 239000001530 fumaric acid Substances 0.000 description 1
- 229910021485 fumed silica Inorganic materials 0.000 description 1
- LNMQRPPRQDGUDR-UHFFFAOYSA-N hexyl prop-2-enoate Chemical compound CCCCCCOC(=O)C=C LNMQRPPRQDGUDR-UHFFFAOYSA-N 0.000 description 1
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- NWVVVBRKAWDGAB-UHFFFAOYSA-N hydroquinone methyl ether Natural products COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical class CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 description 1
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- CSVRUJBOWHSVMA-UHFFFAOYSA-N oxolan-2-yl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCO1 CSVRUJBOWHSVMA-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
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- 229910052710 silicon Inorganic materials 0.000 description 1
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- 235000015096 spirit Nutrition 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
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- 239000013008 thixotropic agent Substances 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 150000003751 zinc Chemical class 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
-
- 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
- C08F2/00—Processes of polymerisation
- C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
-
- 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
- C08F220/04—Acids; Metal salts or ammonium salts thereof
- C08F220/06—Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
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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
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
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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
- 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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- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1808—C8-(meth)acrylate, e.g. isooctyl (meth)acrylate or 2-ethylhexyl (meth)acrylate
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- C—CHEMISTRY; METALLURGY
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- 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
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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
- 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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- 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
- 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
- C08F230/04—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 a metal
- C08F230/08—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 a metal containing silicon
- C08F230/085—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 a metal containing silicon the monomer being a polymerisable silane, e.g. (meth)acryloyloxy trialkoxy silanes or vinyl trialkoxysilanes
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- 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
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/17—Amines; Quaternary ammonium compounds
- C08K5/18—Amines; Quaternary ammonium compounds with aromatically bound amino groups
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- 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
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3432—Six-membered rings
- C08K5/3437—Six-membered rings condensed with carbocyclic rings
-
- 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
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
-
- 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
- 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
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/17—Amines; Quaternary ammonium compounds
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- 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)
Abstract
Description
本明細書で別段の定めがない限り、本開示と関連して使用される技術用語は、当業者により通常理解されている意味を有するものである。さらに文脈から別の解釈が必要とされ
ない限り、単数形は複数を含み、そして複数形は単数を含むものとする。
式(1)
式(2)
C6アルキル基から選択される、または
式(3)
を有する化合物から選択される。
2,2,4-トリメチル-1,2-ジヒドロキノリンポリマーから選択される。
THFMA:サートマー(Sartomer)から市販されているSartomer(商標)SR203Hとして得たテトラヒドロフルフリルメタクリレート
EHMA:エヴォニック(Evonik)から市販されているVISIOMER(商標)EHMAとして得たエチルヘキシルメタクリレート
MAA:シグマアルドリッチ(Sigma Aldrich)から入手したメタクリル酸Silquest A174:モメンティブ(Momentive)から得たビニル シラン
マレイン酸:DSMから得た
VULKANOX(商標)BHT:ランクセス(Lanxess)から得られるブチル化ヒドロキシトルエン
PARALOID TMS2670J:ダウ(DOW)から得たMBSコア シェル衝撃改質剤
PARALOID EXL 2300G:ダウ(DOW)から得たAIMコア シェル
Sartomer(商標)SR348C:サートマーから得たエトキシル化ビスフェノールA ジメタクリレート
CAB-O-SIL(商標)TS720:カボット(Cabot)から得た処理済フュームドシリカ
Trigonox(商標)C:アクゾノベル(AkzoNobel)から得たt-ブチルペルオキシベンゾエート
ソリジェン銅(Soligen copper):ボルチャーズ(Borchers)から得た
VULKANOX(商標)HS LG:ランクセスから得た2,2,4-トリメチル-1,2-ジヒドロキノリンポリマー
KGL097:レイク ケミカルズ(Lake Chemicals)から得た3,5-ジエチル-1,2-ジヒドロ-1-フェニル-2-プロピルピリジン
表2に示す量は、重量%である。
最初にマレイン酸をTHFMAに室温(約25℃)で溶解した。表2の樹脂用の全ての成分を一緒に加え、そしてスピードミキサー(遠心ミキサー)を使用して、均一な生成物が得られるまで混合した。
200ppmのソリジェン銅(EHMA中)を調製した。表2の硬化剤用の全ての成分を一緒に加え、そしてスピードミキサー(遠心ミキサー)を使用して、均一な生成物が得られるまで混合した。VULKANOX(商標)HS LGを挽いた後に加え、そして次にマトリックスに添加後に溶解した。
7gの樹脂+7gの硬化剤をカップ内で混合し、次いでシリコン型に移し、そして
発熱反応は熱電対を用いて経時的に追跡する。
CFRP(炭素繊維強化ポリマー)およびABS(アクリロニトリルブタジエンスチレン)基材はイソプロパノールで拭いて、そして摩耗させることにより脱脂した。アルミニウム基材はサンドブラストし、そしてアセトンですすいだ。接着剤組成物を基材対の表面に分配した。2つの面を合わせ、そして互いにコンプレッサー型のチューブクランプで保持した。重なった面積は25.0mm × 12.5mmであった。結合した連結部は23℃で24時間、硬化させておいた。次いでクランプを取り外し、そして結合した連結部を引張剪断強度(TSS)について、ISO4587に従い10mm/分のクロスヘッド速度で試験した。TSS値はメガパスカル(MPa)で記録した。3回試験した連結部の平均値を記録する。
2mm厚の板を圧の下に調製し、そして室温(約25℃)で1週間硬化した後、ISO527に従い試験した。
同じ板からのサンプルをねじりについてISO6721に従い-100から+150℃で試験してガラス転移温度を測定した。
Claims (9)
- 1もしくは複数の(メタ)アクリレートエステルモノマー、触媒系および遅延添加剤を含んでなり、遅延添加剤が二級アミンである接着剤組成物。
- 二級アミンが1より多くの二級アミン基を含んでなる二級アミンである請求項1に記載の接着剤組成物。
- 二級アミンが二級アリールアミンである請求項2に記載の接着剤組成物。
- 遅延添加剤が環式二級アミンから選択される請求項1に記載の接着剤組成物。
- 環式二級アミンが、2,2,4-トリメチル-1,2-ジヒドロキノリンポリマーである請求項5記載の接着剤組成物。
- 遅延添加剤が、接着剤組成物の総重量に基づき1重量%から5重量%の量で含まれる前記請求項のいずれかに記載の接着剤組成物。
- 1もしくは複数のメタクリレートエステルモノマーが、接着剤組成物の総重量に基づき10重量%から90重量%の量で含まれる前記請求項のいずれかに記載の接着剤組成物。
- メタクリレートモノマーを含んでなる接着剤組成物用の遅延添加剤としての二級アミンまたは二級アミンの混合物の使用。
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EP18214799.1 | 2018-12-20 | ||
EP18214799 | 2018-12-20 | ||
PCT/EP2019/084878 WO2020126818A1 (en) | 2018-12-20 | 2019-12-12 | Adhesive composition with retarding additive |
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US (1) | US20220049127A1 (ja) |
EP (1) | EP3898814A1 (ja) |
JP (2) | JP2022517175A (ja) |
KR (1) | KR20210106522A (ja) |
CN (1) | CN113166481A (ja) |
AU (1) | AU2019411691A1 (ja) |
BR (1) | BR112021010976A2 (ja) |
CA (1) | CA3121794A1 (ja) |
MX (1) | MX2021007430A (ja) |
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2019
- 2019-12-12 US US17/312,422 patent/US20220049127A1/en active Pending
- 2019-12-12 CN CN201980082285.9A patent/CN113166481A/zh active Pending
- 2019-12-12 SG SG11202105589QA patent/SG11202105589QA/en unknown
- 2019-12-12 AU AU2019411691A patent/AU2019411691A1/en active Pending
- 2019-12-12 BR BR112021010976-5A patent/BR112021010976A2/pt unknown
- 2019-12-12 KR KR1020217022873A patent/KR20210106522A/ko not_active Application Discontinuation
- 2019-12-12 WO PCT/EP2019/084878 patent/WO2020126818A1/en unknown
- 2019-12-12 JP JP2021535725A patent/JP2022517175A/ja active Pending
- 2019-12-12 CA CA3121794A patent/CA3121794A1/en active Pending
- 2019-12-12 EP EP19816363.6A patent/EP3898814A1/en active Pending
- 2019-12-12 MX MX2021007430A patent/MX2021007430A/es unknown
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2024
- 2024-02-02 JP JP2024014568A patent/JP2024054183A/ja active Pending
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JPS5046743A (ja) * | 1973-08-21 | 1975-04-25 | ||
JPS51119050A (en) * | 1975-04-11 | 1976-10-19 | Okura Ind Co Ltd | Quick-curing, anaerobic adhesive |
JPS51142492A (en) * | 1975-06-04 | 1976-12-08 | Toagosei Chem Ind Co Ltd | Hardening accelerator |
JPS5529588A (en) * | 1978-08-16 | 1980-03-01 | Ciba Geigy Ag | Adhesive agent and use thereof to adhere two surfaces |
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SG11202105589QA (en) | 2021-06-29 |
AU2019411691A1 (en) | 2021-06-17 |
CN113166481A (zh) | 2021-07-23 |
CA3121794A1 (en) | 2020-06-25 |
US20220049127A1 (en) | 2022-02-17 |
BR112021010976A2 (pt) | 2021-09-08 |
MX2021007430A (es) | 2021-08-05 |
WO2020126818A1 (en) | 2020-06-25 |
EP3898814A1 (en) | 2021-10-27 |
KR20210106522A (ko) | 2021-08-30 |
JP2024054183A (ja) | 2024-04-16 |
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