JP2020533433A - ウレタンアクリレートハイブリッド構造接着剤 - Google Patents
ウレタンアクリレートハイブリッド構造接着剤 Download PDFInfo
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- JP2020533433A JP2020533433A JP2020512495A JP2020512495A JP2020533433A JP 2020533433 A JP2020533433 A JP 2020533433A JP 2020512495 A JP2020512495 A JP 2020512495A JP 2020512495 A JP2020512495 A JP 2020512495A JP 2020533433 A JP2020533433 A JP 2020533433A
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- Japan
- Prior art keywords
- adhesive composition
- polymerizable adhesive
- composition according
- diisocyanate
- group
- 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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- 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
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
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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
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/06—Polymers provided for in subclass C08G
- C08F290/067—Polyurethanes; Polyureas
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/088—Removal of water or carbon dioxide from the reaction mixture or reaction components
- C08G18/0885—Removal of water or carbon dioxide from the reaction mixture or reaction components using additives, e.g. absorbing agents
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
- C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/16—Catalysts
- C08G18/161—Catalysts containing two or more components to be covered by at least two of the groups C08G18/166, C08G18/18 or C08G18/22
- C08G18/163—Catalysts containing two or more components to be covered by at least two of the groups C08G18/166, C08G18/18 or C08G18/22 covered by C08G18/18 and C08G18/22
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- C—CHEMISTRY; METALLURGY
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- C—CHEMISTRY; METALLURGY
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08G18/242—Catalysts containing metal compounds of tin organometallic compounds containing tin-carbon bonds
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
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- C08G18/30—Low-molecular-weight compounds
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- C08G18/3246—Polyamines heterocyclic, the heteroatom being oxygen or nitrogen in the form of an amino group
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/667—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38
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Abstract
Description
式中、Rは、ヒドロキシル、ウレタン、エポキシ、またはフェノールオリゴマーなどの他の官能基の有無にかかわらず、アルキル、シクロアルキル、またはビシクロアルキルであり得;R’は、水素またはメチル基のいずれかであり得る。
ジ(2−エチルヘキシル)スズオキシド、ジブチルスズジメルカプチド、ジブチルスズジイソオクチルマレエート、ジブチルスズジイソオクチルメルカプトアセテート、ジメチルスズジメルカプチド、ジブチルスズジラウリルメルカプチド、ジメチルスズジラウリルメルカプチド、ジメチルスズジイソオクチルメルカプトアセテート、ジメチルジ(n−ブチル)スズビス(イソオクチルメルカプトアセテート)、ジブチルスズビスイソオクチルマレエート、ジブチルスズジ−2−エチルヘキソエート、ジラウリルスズジアセテート、ジオクチルスズジアセテート、トリアルキルスズヒドロキシド、ジアルキルスズオキシド、ジブチルスズスルフィド、ジ(イソオクチル)スズビス(イソオクチル−メルカプトアセテート)、ネオデカン酸亜鉛、およびアセチルアセトナト鉄、ならびにオクトエート、ネオデカノエート、ピバレート、2−エチルヘキサノエート、ナフタネート、鉄ペンタンジオン、ニッケルアセチルアセトネートなどのビスマス化合物およびそれらの組み合わせが挙げられる。
34.8グラムのPluracol(登録商標)P2010、14.0グラムの乾燥タルク、1.7グラムのヒュームドシリカ、19.8グラムのRubinate(登録商標)1680、10.6グラムのLupranate(登録商標)M20(BASFから市販のポリマーMDI)を混合して混合物を形成した。次に、混合物を約65℃〜70℃に加熱し、その温度で約60分間維持した。5グラムのRubinate1680、5.3グラムのモレキュラーシーブタイプ5A、および8.4グラムのテトラヒドロフルフリルメタクリレートをその混合物に添加して、約8パーセントのNCO含有量を有するプレポリマーA1を形成した。
41.3グラムのAcclaim(登録商標)4220N、5.8グラムのAdmex(商標)525、19.6グラムのPriplast(商標)3238、22.8グラムの乾燥タルク、1.5グラムのヒュームドシリカ、5.1グラムの1,4−ブタンジオール、1.3グラムのピペラジン、0.045グラムのジブチルスズジイソオクチルマレエート、0.12グラムのジブチルスズジスルフィド、0.02グラムのジメチルビス[(1−オキソネオデシル)オキシ]スタンナン、および2.0グラムのトリ−n−ブチルボラン−3−メトキシ−1−プロピルアミン(TnBB MOPA)を混合して、硬化剤B1を形成した。
35.0グラムのPluracol(登録商標)P2010、14.1グラムの乾燥タルク、19.9グラムのRubinate(登録商標)1680、および10.7グラムのLupranate(登録商標)M20を混合して、混合物を形成した。次に、混合物を約65℃〜70℃に加熱し、温度を約60分間維持した。5グラムのRubinate(登録商標)1680、5.3グラムのモレキュラーシーブタイプ5A、6.6グラムのアクリレート末端ウレタン/アクリレートオリゴマー(Ebecryl(登録商標)4827)および3.0グラムのテトラヒドロフルフリルメタクリレートをその混合物に添加して、約8パーセントのNCO含有量を有するプレポリマーA2を形成した。
41.7グラムのAcclaim(登録商標)4220N、5.88グラムのAdmex(商標)525、19.4グラムのGX−9201、23.0グラムの乾燥タルク、2.2グラムのヒュームドシリカ、4.4グラムの1,4−ブタンジオール、1.3グラムのピペラジン、0.02グラムのジブチルスズジイソオクチルマレエート、0.06グラムのジブチルスズジスルフィド、0.01グラムのジメチルビス[(1−オキソネオデシル)オキシ]スタンナン、および2.0グラムのTnBB MOPAを添加して、硬化剤B2を形成した。
13.93グラムのPluracol(登録商標)P2010、1.96グラムのPluracol(登録商標)TP−440、7.40グラムの乾燥タルク、2.92グラムのヒュームドシリカ、28.21グラムのRubinate(登録商標)1680を混合して、混合物を形成した。次に、混合物を約65℃〜70℃に加熱し、この温度で約60分間維持した。38.16グラムのRubinate(登録商標)1680および7.35グラムのモレキュラーシーブタイプ5Aを混合物に加えて、約18.0パーセントのNCO含有量を有するプレポリマーA3を形成した。
ヒドロキシル末端ウレタン変性架橋付加物ポリマー1は、52.2グラムのPluracol TP-440ポリオール、10.20グラムのMDI(Mondur(登録商標)MLQ、Covestroから市販)、4.25グラムのRubinate 1680をブレンドして混合物を形成することによって調製した。次に、その混合物を約82℃に加熱し、約60分間混合し続けた。33.35グラムのAcclaim4220Nをその混合物に加えて、約29パーセントの付加物含有量を有するポリマー1を形成した。
38.70グラムの例6で調製したポリマー1、23.08グラムのAcclaim4220N、21.30グラムの乾燥タルク、3.90グラムのヒュームドシリカ、10.0グラムの1,4-ブタンジオール、1.26グラムのピペラジン、0.01グラムのジブチルスズジイソオクチルマレエート、0.025グラムのジブチルスズジスルフィドおよび1.00グラムのモレキュラーシーブタイプAを添加して、硬化剤B3を形成した。
23グラムのPluracol(登録商標)P2010、12グラムのPriplast 3238、14グラムの乾燥タルク、1.5グラムのヒュームドシリカ、37グラムのRubinate(登録商標)1680を混合して、混合物を形成した。次に、混合物を約65℃〜70℃に加熱し、この温度で約60分間維持した。5グラムのモレキュラーシーブタイプ5A、1グラムのヒドロキシプロピルメタクリレートおよび6グラムのテトラヒドロフルフリルメタクリレートを混合物に添加して、約9パーセントのNCO含有量を有するプレポリマーA4を形成した。
49グラムのAcclaim 4220N、7.5グラムのEmerox 14001、5グラムのCapa(商標)8025E(カプロラクトンモノマーに由来し、ヒドロキシル基で終端されている分岐コポリエステルトリオール、Perstorp Groupから市販)、30グラムの乾燥タルク、1.1グラムのヒュームドシリカ、5.4グラムの1,4−ブタンジオール、1.3グラムのピペラジン、0.05グラムのジブチルスズジイソオクチルマレエート、0.03グラムのジメチルビス[(1−オキソネオデシル)オキシ]スタンナン、および1グラムのTnBB MOPAを添加して、硬化剤B4を形成した。
表1に示す例10〜15では、例1〜5および7〜9で調製したプレポリマーおよび硬化剤を、市販のプレポリマーおよび硬化剤と共に別々に並べたカートリッジに装填し、静的混合管を通してポンプで送り、完全な混合を実現した。その混合した重合性接着剤組成物を、静的混合管から試験基板の片側に直接塗布した。得られたハイブリッド接着剤のバルク物理特性について評価した。接着剤結合の重ねせん断強度を測定するために重ねせん断試験を行った。
*Betaseal(商標)X2500 Plus構造用接着剤は、The Dow Chemical Companyから市販されている。
RT=20〜25℃
IPA=イソプロピルアルコール
E−coat:ミズーリ州モバリーのMack Hils,Inc.から市販
Plasan Carbon Fiber:ミシガン州ウォーカーのPlasan Carbon Compositesから市販
Magna Carbon Fiber:Magna International Inc.から市販
Claims (33)
- 有機ボラン錯体、二量体脂肪ポリオールとポリエーテルポリオールとを含む遊離ポリオール、少なくとも1つのフリーラジカル重合性成分、イソシアネート末端ウレタンプレポリマー、遊離イソシアネート、および低分子量鎖延長化合物を含む、重合性接着剤組成物。
- 前記二量体脂肪ポリオールが、二量体脂肪酸とジオールから、または二量体脂肪ジオールと二酸から誘導されている、請求項1に記載の重合性接着剤組成物。
- 前記ジオールが、エチレングリコール、プロパンジオール、ブタンジオール、ヘキサンジオール、およびそれらの組み合わせからなる群より選択される、請求項2に記載の重合性接着剤組成物。
- 前記二酸が、アジピン酸、グルタル酸、コハク酸、ピメリン酸、スベリン酸、アゼライン酸、セバシン酸、ヘプタンジカルボン酸、オクタンジカルボン酸、ノナンジカルボン酸、デカンジカルボン酸、ウンデカンジカルボン酸、ドデカンジカルボン酸、およびそれらの組み合わせからなる群より選択される、請求項2に記載の重合性接着剤組成物。
- 前記ポリエーテルポリオールが、置換または非置換のポリアルキレンエーテルグリコール、ポリヒドロキシポリアルキレンエーテル、ポリオールのエチレンまたはプロピレンオキシド付加物、グリセロールの一置換エステル、およびそれらの組み合わせからなる群より選択される、請求項1〜4のいずれか一項に記載の重合性接着剤組成物。
- 前記ポリエーテルポリオールが、プロピレンオキシドのポリマーまたはエチレンとプロピレンオキシドとのコポリマーを含む、請求項5に記載の重合性接着剤組成物。
- 前記少なくとも1つのフリーラジカル重合性成分が、アルキルおよびシクロアルキルアクリレート、アルキルメタクリレート、ヒドロキシルアルキルアクリレートおよびメタクリレート、ならびにそれらの組み合わせからなる群より選択されるモノマーである、請求項1〜6のいずれか一項に記載の重合性接着剤組成物。
- 前記アルキルおよびシクロアルキルアクリレートが、メチルアクリレート、エチルアクリレート、イソボルニルアクリレート、ブチルアクリレート、n−オクチルアクリレート、2−エチルヘキシルアクリレート、シクロヘキシルアクリレート、グリシジルアクリレート、テトラヒドロフルフリルアクリレート、プロピルアクリレート、およびそれらの組み合わせからなる群より選択される、請求項7に記載の重合性接着剤組成物。
- 前記アルキルメタクリレートが、メチルメタクリレート、エチルメタクリレート、ブチルメタクリレート、2−エチルヘキシルメタクリレート、イソボルニルメタクリレート、デシルメタクリレート、ドデシルメタクリレート、グリシジルメタクリレート、テトラヒドロフルフリルメタクリレート、プロピルメタクリレート、およびそれらの組み合わせからなる群より選択される、請求項7に記載の重合性接着剤組成物。
- 前記ヒドロキシルアルキルアクリレートおよびメタクリレートが、ヒドロキシプロピルアクリレート、ヒドロキシルメチルメタクリレート、ヒドロキシルエチルメタクリレート、ヒドロキシプロピルメタクリレートからなる群より選択される、請求項7に記載の重合性接着剤組成物。
- 前記低分子量鎖延長化合物が、エチレングリコール、ジエチレングリコール、1,2−プロピレングリコール、1,3−プロピレングリコール、ジプロピレングリコール、1,4−ブタンジオール、1,4−ブチレングリコール、1,6−ヘキシレングリコール、ネオペンチルグリコール、3−メチルペンタングリコール、1,4−ビス(ヒドロキシメチル)シクロヘキサン、1,4−シクロヘキサン−ジメタノール、およびそれらの組み合わせからなる群より選択される、請求項1〜10のいずれか一項に記載の重合性接着剤組成物。
- 前記低分子量鎖延長化合物が、1,4−ブタンジオールである、請求項11に記載の重合性接着剤組成物。
- 前記有機ボラン錯体が、窒素含有化合物を有するトリアルキルボランを含む、請求項1〜12のいずれか一項に記載の重合性接着剤組成物。
- 前記窒素含有化合物が、第一級および第三級アミンからなる群より選択される置換または置換アミンである、請求項13に記載の重合性接着剤組成物。
- 前記アミンが、ジアミン、ピリジン、ピロールまたはカルバゾールである、請求項14に記載の重合性接着剤組成物。
- 前記有機ボラン錯体が、トリエチルボランジメチルアミノプロピルアミン錯体、トリブチルボランジメチルアミノプロピルアミン錯体、トリエチルボランピロリジン錯体、トリ−t−ブチルボランピロリジン錯体、トリエチルボランピリジン錯体、トリ−t−ブチルピリジン錯体、トリエチルボランメトキシプロピルアミン錯体、およびトリブチルボランメトキシプロピルアミン錯体からなる群より選択される、請求項1〜15のいずれか一項に記載の重合性接着剤組成物。
- 前記有機ボラン錯体が、トリブチルボランメトキシプロピルアミン錯体である、請求項16に記載の重合性接着剤組成物。
- 前記イソシアネート末端ウレタンプレポリマーが、過剰のイソシアネートとポリオールとの重合から調製されている、請求項1〜17のいずれか一項に記載の重合性接着剤組成物。
- 前記イソシアネートが、芳香族ジイソシアネート、および脂肪族および脂環式ジイソシアネートからなる群より選択される、請求項18に記載の重合性接着剤組成物。
- 前記芳香族ジイソシアネートが、2,4−または2,6−トリレンジイソシアネート(TDI);ジフェニル−メチレンジイソシアネート;ナフタレン−1,5−ジイソシアネート;メチレンジイソシアネート;m−またはp−フェニレンジイソシアネート;カルボジイミド基、ウレタン基、アロファネート基、イソシアヌレート基、尿素基、ビウレット、またはウレトンイミン基を含む変性芳香族ジイソシアネート;およびそれらの組み合わせからなる群より選択される、請求項19に記載の重合性接着剤組成物。
- 前記変性芳香族ジイソシアネートが、2,4−または2,6−トリレンジイソシアネート;または、4,4’−または2,4’−ジフェニルメタンジイソシアネートから誘導されている、請求項20に記載の重合性接着剤組成物。
- 前記変性芳香族ジイソシアネートが、ウレトンイミン変性4,4’−ジフェニルメタンジイソシアネートである、請求項21に記載の重合性接着剤組成物。
- 前記脂肪族および脂環式ジイソシアネートが、1,4−テトラメチレンジイソシアネート、1,6−ヘキサメチレンジイソシアネート、2,2,4−トリメチル−1,6−ヘキサメチレンジイソシアネート、1,12−ドデカメチレンジイソシアネート、シクロヘキサン−1,3−または−1,4−ジイソシアネート、1−イソシアナト−2−イソシアナトメチルシクロペンタン、1−イソシアナト−3−イソシアナト−メチル−3,5,5−トリメチルシクロヘキサン(イソホロンジイソシアネートまたはIPDI)、ビス−(4−イソシアナトシクロヘキシル)−メタン、2,4’−ジシクロヘキシルメタンジイソシアネート、1,3−または1,4−ビス−(イソシアナトメチル)−シクロヘキサン、ビス−(4−イソシアナト−3−メチルシクロヘキシル)−メタン、α’、α’、α’、α’−テトラメチル−1,3−および/または−1,4−キシリレンジイソシアネート、1−イソシアナト−1−メチル−4(3)−イソシアナトメチルシクロヘキサン、2,4−または2,6−ヘキサヒドロトリレンジイソシアネート、およびそれらの組み合わせからなる群より選択される、請求項19に記載の重合性接着剤組成物。
- 前記遊離ポリオールが、カルダノールベースのポリエステルポリオール、またはポリ−ε−カプロラクトンポリオールをさらに含む、請求項1に記載の重合性接着剤組成物。
- タルク、マイカ、カオリン、ベントンクレー、酸化アルミニウム、酸化チタン、酸化鉄、硫酸バリウム、ホーンブレンド、角閃石、クリソタイル、カーボンブラック、炭素繊維、ヒュームドシリカ、モレキュラーシーブおよびそれらの組み合わせからなる群より選択される充填剤をさらに含む、請求項1〜24のいずれか一項に記載の重合性接着剤組成物。
- トリエチルアミン、ベンジルジメチルアミン、トリエチレンジアミン、テトラメチルブタンジアミン、ジアゾビシクロウンデセン、酢酸第一スズ、オクタン酸第一スズ、ラウリン酸第一スズ、オレイン酸第一スズ、ジブチルスズジアセテート、ジブチルスズジラウレート、ジブチルスズマレエート、ジブチルスズジ−2−エチルヘキソエート、ジラウリルスズジアセテート、ジオクチルスズジアセテートなどのカルボン酸のジアルキルスズ塩、トリアルキルスズヒドロキシド、ジアルキルスズオキシド、ジブチルスズジスルフィド、ジブチルスズジイソオクチルマレエート、ジブチルスズジラウリルメルカプチド、ジブチルスズジ(イソオクチルメルカプトアセテート)、ネオデカン酸亜鉛、鉄アセチルアセトネート、およびそれらの組み合わせからなる群より選択される触媒をさらに含む、請求項1〜25のいずれか一項に記載の重合性接着剤組成物。
- それぞれが少なくとも1つの表面を有する少なくとも2つの基板および請求項1〜26のいずれか一項に記載の重合性接着剤組成物を含む、物質の組成物。
- 前記基板が、不飽和ポリエステル樹脂、ビニルエステル樹脂、エポキシ樹脂、金属、ポリプロピレン、熱可塑性オレフィン、ナイロン、アクリロニトリルブタジエンスチレンおよびそれらの組み合わせを含む、請求項27に記載の物質の組成物。
- 請求項27または28に記載の物質の組成物を含む、物品。
- (a)少なくとも1つの表面を有する第1の基板を準備すること、
(b)少なくとも1つの表面を有する第2の基板を準備すること、
(c)請求項1〜26のいずれか一項に記載の重合性接着剤組成物を準備すること、
(d)前記第1の基板、前記第2の基板、または前記第1および第2の基板の両方、の前記少なくとも1つの表面に前記重合性接着剤組成物を塗布すること、
前記重合性接着剤組成物を有する前記基板の1つの表面を並置して他の基板の表面と接触するように、前記第1の基板および第二の基板を位置合わせすること、および、
前記重合性接着剤組成物を硬化させること、
を含む、少なくとも2つの基板を結合する方法。 - 前記基板が、不飽和ポリエステル樹脂、ビニルエステル樹脂、エポキシ樹脂、金属、ポリプロピレン、熱可塑性オレフィン、ナイロン、アクリロニトリルブタジエンスチレンおよびそれらの組み合わせを含む、請求項30に記載の方法。
- 前記重合性接着剤組成物を、静的または動的ミキサーで塗布する、請求項30または31に記載の方法。
- 前記表面を、前記重合性接着剤組成物の塗布前に処理する、請求項30〜32のいずれか一項に記載の方法。
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