JP2018522967A - Uv硬化性エポキシ/アクリレート接着剤組成物 - Google Patents
Uv硬化性エポキシ/アクリレート接着剤組成物 Download PDFInfo
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- JP2018522967A JP2018522967A JP2017562737A JP2017562737A JP2018522967A JP 2018522967 A JP2018522967 A JP 2018522967A JP 2017562737 A JP2017562737 A JP 2017562737A JP 2017562737 A JP2017562737 A JP 2017562737A JP 2018522967 A JP2018522967 A JP 2018522967A
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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
- 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
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- C—CHEMISTRY; METALLURGY
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
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- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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- 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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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
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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
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
- C08L71/02—Polyalkylene oxides
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- C—CHEMISTRY; METALLURGY
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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- C08L71/08—Polyethers derived from hydroxy compounds or from their metallic derivatives
- C08L71/10—Polyethers derived from hydroxy compounds or from their metallic derivatives from phenols
- C08L71/12—Polyphenylene oxides
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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
- 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
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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
- C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
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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
- C09J5/00—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers
- C09J5/06—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers involving heating of the applied adhesive
-
- 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
- C09J7/00—Adhesives in the form of films or foils
- C09J7/20—Adhesives in the form of films or foils characterised by their carriers
-
- 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
- C09J7/00—Adhesives in the form of films or foils
- C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
-
- 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
- C09J7/00—Adhesives in the form of films or foils
- C09J7/40—Adhesives in the form of films or foils characterised by release liners
-
- 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
- C08G2650/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G2650/28—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type
- C08G2650/56—Polyhydroxyethers, e.g. phenoxy resins
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
- C08L2205/025—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group containing two or more polymers of the same hierarchy C08L, and differing only in parameters such as density, comonomer content, molecular weight, structure
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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
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- C08L2205/03—Polymer mixtures characterised by other features containing three or more polymers in a blend
- C08L2205/035—Polymer mixtures characterised by other features containing three or more polymers in a blend containing four or more polymers in a blend
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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
- C09J131/00—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 an acyloxy radical of a saturated carboxylic acid, of carbonic acid, or of a haloformic acid; Adhesives based on derivatives of such polymers
- C09J131/02—Homopolymers or copolymers of esters of monocarboxylic acids
- C09J131/04—Homopolymers or copolymers of vinyl acetate
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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
- C09J137/00—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 heterocyclic ring containing oxygen; Adhesives based on derivatives of such polymers
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Abstract
【選択図】なし
Description
本発明は、構造用及び半構造用結合接着剤、接着剤物品、並びに該接着剤及び物品の調製方法に関する。本発明は更に、構造用結合接着剤と共に結合する1種以上の構成成分を含有する製造物品に関する。
構造用結合テープは、1つ以上の基材を互いに結合させるのに有用である。多くの構造用結合テープは、2つの群、すなわち(1)熱硬化性構造用結合テープ、及び(2)紫外線(UV)光活性構造用結合テープのいずれかに属する。分類名が示すように、熱硬化性構造用結合テープは、テープの接着剤組成物を硬化するために、加熱を必要とする。UVi構造用結合テープは、紫外線で露光すると硬化が開始するが、硬化させるのに加熱は必要としない接着剤組成物を含有する。UVi構造用結合テープの硬化を加速するために加熱をしてもよい。
本開示は、希な接着特性を有すると共に、コールドフロー特性が改善された、新規の構造用又は半構造用接着剤の発見により、上述した困難及び課題のいくつかに対処する。構造用結合接着剤は、望ましい強度及び接着特性を有する。接着剤は光活性化(すなわち、光源にさらされると硬化が開始する)し、硬化に加熱を必要としない。構造用結合接着剤は、多数の用途、特に、1つ以上の基材を共に結合するための接着剤に用いてもよい。
接着剤組成物は、テトラヒドロフルフリル(メタ)アクリレートコポリマー成分を部分的に含む。特に規定がない限り、THFアクリレート及びTHFメタクリレートは、THFAと略する。より詳細には、接着剤組成物は、テトラヒドロフルフリル(メタ)アクリレート、C1〜C8(メタ)アクリレートエステル、及び任意のカチオン反応性の官能性(メタ)アクリレートを含む。
εα−ω[(アルカノールの物質量)×(アルカノールの炭素原子数)]/αからωのアルカノールの物質量数
a)40〜60重量%、好ましくは50重量%超60重量%以下(> 50 to 60 wt.%)のテトラヒドロフルフリル(メタ)アクリレート、
b)40〜60重量%、好ましくは40〜50重量%のC1〜C8、好ましくはC3〜C6のアルキル(メタ)アクリレートエステルモノマー、
c)0〜10重量%、好ましくは1〜5重量%のカチオン反応性の官能性モノマー、
なお、a)〜c)の合計は100重量%である。
a.15〜50部のTHFA(メタ)アクリレートコポリマー、
b.25〜50部のエポキシ樹脂成分、
c.5〜15部のポリエーテルポリオール、
d.10〜25部のヒドロキシ官能性フィルム形成ポリマー
a)〜d)の合計は、100重量部)及び、
e.a)〜d)100部に対して、0.01〜1部のカチオン性光開始剤を含む。
A−CO−(Y)b−B
を有し、式中、YはCO又はCR11R12であり、R11及びR12は同一でも異なっていてもよく、かつ水素、アルキル、アルカリル、又はアラルキルであり得、bは1又は0である。更にA及びBは同じか若しくは異なり得、かつ置換(1つ以上の非干渉置換基を有する)若しくは非置換のアリール基、アルキル基、アルカリル基若しくはアラルキル基であり得、又はA及びBが一緒になって環状構造を形成し得て、これは置換若しくは非置換の脂環式環、芳香環、芳香族複素環若しくは縮合芳香環であり得る。
[(L1)(L2)Mm]+eX−
を有し、式中、Mmは周期族IVB、VB、VIB、VIIB、及びVIIIの元素から選択された金属原子を表し、好ましくはCr、Mo、W、Mn、Re、Fe、及びCoであり、
L1は、0、1、又は2個のπ電子供与配位子を表し、該配位子は同一でも異なっていてもよく、各配位子は、置換及び非置換の脂環式及び環式の不飽和化合物、並びに置換及び非置換の炭素環式芳香族化合物及び複素環式芳香族化合物からなる群から選択されてよく、該配位子の各々は2〜12個のπ電子を金属原子Mの価電子殻へ供与可能である。
eは1又は2の値を有する整数で、錯体カチオンの残留電荷であり、
Xは、前述したように、ハロゲン含有錯体アニオンである。
動的重なり剪断力
E−コーティングされたスチール(「stl」)への接着性を、結合した試験片の重なり剪断強度を測定することによって決定した。複数の25mm×50.8mmの基材片をイソプロピルアルコール及び水の1:1(v:v)溶液で拭き、風乾させた。12.7mm×25mm部分の接着剤組成物の片側から剥離ライナーを除去し、該組成物を1つの片へと貼り付けた。第2の剥離ライナーを除去し、UVICURE Plus積算放射計(EIT,Inc.(Sterling,VA))で測定しながら、該組成物をマイクロ波源(0.9〜1.2J/cm2、UVA,Hバルブ,Heraeus Noblelight America(Gaithersburg,MD))で露光した。第2の片を照射した試料へと貼り付け、こうして結合させた。6kgの静荷重を試験片に30〜60秒加えることによって、積層物をウエットアウトさせた。試験に先だって、試験片を周囲温度及び湿度にて24時間硬化させた。
プラスチックのガラスに対する接着性を、結合した試験片のへき開強度を測定することによって決定した。22mm×28mm×4mmのCRASTIN製のプラスチックテストピース、及び127mm×50mm×4mm強化ガラスプラークを、イソプロピルアルコール及び水の1:1(v:v)溶液で拭き、風乾させた。22mm×28mm部分の接着剤組成物から剥離ライナーを除去し、この部分をプラスチックのテストピースへと貼り付けた。1〜3kgの重量をテストピースに30秒間加えることによってウエットアウトさせた。第2の剥離ライナーを除去し、UVICURE Plus積算放射計(EIT,Inc.(Sterling,VA))で測定しながら、接着剤部分をマイクロ波源(0.9〜1.2J/cm2、UVA,Hバルブ,Heraeus Noblelight America(Gaithersburg,MD))で露光した。照射した試料を、強化ガラスプラークへと貼り付け、6kgの重量を、結合した積層物へ30〜60秒間加えることによってウエットアウトさせた。試験に先だって、積層物を周囲条件下にて24時間硬化させた。
MCT/A検出器及びSMART OMNI一回反射型ゲルマニウム(GE)減衰全反射(ATR)アクセサリを伴う、NICOLET NEXUS 670 IR分光計(Thermo Fisher Scientific Inc.(Waltham,MA))で、ATR測定を実施した。スペクトルは、4000〜650cm−1の範囲にわたる分解能が4(データ間隔=2cm−1)で、32回の積算からなる。
組成物のクリープ性能及び寸法安定性を、MCR302レオメータ(Anton Paar GmbH(Graz,Austria))を使用して決定した。各組成物の0.6mm厚試料を25mmの平行板の間に載せ、1Nの垂直力(FN)を加えた。1000Paの一定応力を300秒間加え、次に、0Paの一定応力を600秒間加えた。組成物のクリープ特性(「コールドフロー」)を決定するために300秒の間のひずみ(γ300s)を記録し、%ひずみで得た。
アクリルコポリマーのガラス転移温度Tgを、MCR302レオメータ(Anton Paar GmbH(Graz,Austria))を、振動モードで使用して、決定した。試料を8mmの平行板に載せ、0.1Nの垂直力を加えた。最初に試料を、30℃から−50℃へと、10℃/分で冷却した。ひずみ(γ)は、1%から0.01%まで減少し、垂直力(FN)は、0.1Nから0.5Nへと増加した。次に、−50℃から150℃へと10℃/分で加熱しながら試料を分析した。γは0.01%から5%へと増加し、FNは0.5Nから0.05Nへと減少した。全実験において、振動周波数(F)は1Hzであった。tan(δ)の主たるピークと一致する温度を、Tgとして記録し、単位℃で得た。
方法1
アクリルコポリマー混合物をKarim(米国特許第5721289号)の方法によって調製した。各組成物について、全アクリルモノマー及び0.04部のIRGACURE 651光開始剤をガラスジャー内で混合した。F1のみ、29部のEPON828、及び10部のEPON1001Fを、追加で、添加した。溶液を窒素でパージし、攪拌しながら、混合物の粘度が塗布に好適になるまで(500〜5000cP)UVA光で露光した。100部の上記シロップ、0.2部のIRGACURE 651、及び任意の残っている構成成分(エポキシ及び/又はアルコール)の混合物を作製した。混合物を、0.050mmのシリコーンコートされたポリ(エチレンテレフタレート)剥離ライナー2つの間に、0.75mm厚でコーティングした。UVIRAD低エネルギーUV積算放射計(EIT,Inc.(Sterling,VA))で測定しながら、この両面ライナー構造を、各側から、350BL蛍光性バルブからの1200mJ/cm2のUVAで照射した。その後の合成に先立って、剥離ライナーを除去した。
アクリルコポリマーをHamer(米国特許第5804610号)の方法によって調製した。アクリルモノマー、ラジカル光開始剤(IRGACURE 651)、及び連鎖移動剤(IOTG)を、アンバーガラスジャー内で混ぜ合わせ、手動でかき混ぜる(swirling by hand to mix)ことにより溶液を調製した。溶液を、熱融着したエチレンビニルアセテート系フィルムのコンパートメント内に、25gのアリコートとして分配し、16℃のウォーターバスに浸し、UV光(UVA=4.7mWcm−2、8分/片面)を使用して重合させた。
組成物を、50又は250g対応の加熱混合ヘッド及び混練機素を装着したBRABENDERミキサー(C.W.Brabender(Hackensack,NJ))を使用して調製した。ミキサーを望ましい混合温度、120〜150℃で稼動させ、混練機素を100rpmで動作させた。最初にアクリルコポリマーを添加し、数分間混合した。固体エポキシ樹脂及びヒドロキシ官能性フィルム形成ポリマーを添加し、混合物全体が均一な分布となるまで混合した。液体エポキシ樹脂、ポリオール、及びシラン材料を、均一な分布となるまで、徐々に添加した。得られた混合物を数分間攪拌し、次に光酸発生剤を滴加した。混合物を数分間攪拌し、次に、アルミニウムパンへ移し、冷却した。材料の塊を2つの剥離ライナーの間に置き、液圧プレス(Carver Inc.(Wabash,IN))を使用して、95℃まで加熱しながら押圧し0.6mm厚のフィルムにした。
a米国特許第5721289号実施例10
b米国特許第5721289号実施例4
c米国特許出願公開第2002/0182955(A1)号:明細書の[0073];合成の際、組成物はマクロ相分離を示し、それ以上評価できなかった。
d米国特許出願公開第2002/0182955(A1)号:実施例AE−1;組成物は、コーティングの際剥離ライナーに浸透し、フィルム形成特性の乏しさを示した。
eATRは、指定の硬化プロファイル後の、硬化の均一性を評価した。各表面に関して、エポキシ変換を、硬化(C)、部分的な硬化(P)、又は未硬化(U)として記録した。
Claims (24)
- a.15〜50部のテトラヒドロフルフリル(メタ)アクリレートコポリマー、
b.25〜50部のエポキシ樹脂成分、
c.5〜15部の液体ポリエーテルポリオール、及び
d.10〜25部のヒドロキシ官能性フィルム形成ポリマーを含み、
a)〜d)の合計は、100重量部であり、
e.a)〜d)100部に対して、0.1〜1部のカチオン性光開始剤を更に含む、硬化性組成物。 - 前記テトラヒドロフルフリル(メタ)アクリレートコポリマーが、
a)40〜60重量%、好ましくは50重量%超60重量%以下のテトラヒドロフルフリル(メタ)アクリレートモノマー、
b)40〜60重量%、好ましくは40重量%以上50重量%未満のC1〜C8アルキル(メタ)アクリレートエステルモノマー、
c)0〜10重量%のカチオン反応性の官能性(メタ)アクリレートエステルモノマーを含み、
a)〜c)の合計は100重量%である、請求項1に記載の硬化性組成物。 - エポキシ樹脂のアクリレートポリマーに対する重量比が、1.1:1〜5:1である、請求項1又は2に記載の硬化性組成物。
- 前記エポキシ樹脂が、カチオン反応性(メタ)アクリレートエステル官能性モノマーを0.1〜5重量%の量で含む、請求項1〜3のいずれか一項に記載の硬化性組成物。
- 前記フィルム形成ポリマーが、フェノキシ樹脂、エチレン/ビニルアセテート(EVA)コポリマー、ポリカプロラクトンポリオール、ポリエステルポリオール、及びポリビニルアセタール樹脂から選択される、請求項1〜4のいずれか一項に記載の硬化性組成物。
- 前記カチオン性光開始剤が、スルホニウム塩又はヨードニウム塩である、請求項1〜5のいずれか一項に記載の硬化性組成物。
- 前記エポキシ樹脂が、2種以上のエポキシ樹脂を含み、少なくとも1種のエポキシ樹脂は、エポキシ当量が約300〜約500であり、少なくとも1種のエポキシ樹脂は、エポキシ当量が約1000〜約1200である、請求項1〜6のいずれか一項に記載の硬化性組成物。
- 前記テトラヒドロフルフリル(メタ)アクリレートコポリマーが、酸官能性モノマー単位を有しない、請求項1〜7のいずれか一項に記載の硬化性組成物。
- 前記C1〜C8アルキル(メタ)アクリレートエステルのモル平均炭素数が、3〜6である、請求項1〜8のいずれか一項に記載の硬化性組成物。
- 前記テトラヒドロフルフリル(メタ)アクリレートコポリマーが、テトラヒドロフルフリル/ブチルアクリレートコポリマーである、請求項1〜9のいずれか一項に記載の硬化性組成物。
- a.25〜35部のテトラヒドロフルフリル(メタ)アクリレートコポリマー、
b.35〜45部のエポキシ樹脂成分、
c.5〜15部のポリエーテルポリオール、及び
d.10〜25部のヒドロキシ官能性フィルム形成ポリマーを含み、
a)〜d)の合計は、100重量部であり、
e.a)〜d)100部に対して、0.1〜1部のカチオン性光開始剤を更に含む、請求項1〜10のいずれか一項に記載の硬化性組成物。 - 前記ヒドロキシ官能性フィルム形成ポリマーが、フェノキシ樹脂、エチレン/ビニルアセテート(EVA)コポリマー(25℃において固体)、ポリカプロラクトンポリオール、ポリエステルポリオール、及び25℃において固体であるポリビニルアセタール樹脂から選択される、請求項1〜11のいずれか一項に記載の硬化性組成物。
- 前記ヒドロキシル官能性フィルム形成ポリマーのヒドロキシル価が少なくとも0.01である、請求項12に記載の硬化性組成物。
- 請求項1〜13のいずれか一項に記載の接着剤の調製方法であって、
a)少なくとも部分的に(複数種類のモノマー)のモノマー混合物を重合させ、テトラヒドロフルフリル(メタ)アクリレートコポリマーを生成する工程と、
b)前記コポリマーを、エポキシ樹脂、ポリエーテルポリオール、前記ヒドロキシ官能性フィルム形成ポリマー、カチオン性光開始剤、及び任意で追加のフリーラジカル光開始剤と組み合わせる工程と、
c)任意で、前記混合物をコーティングする工程と、
d)光重合させる工程と、を含む方法。 - 工程a)の前記モノマー混合物が部分的に重合されて、溶媒モノマー中の溶質テトラヒドロフルフリル(メタ)アクリレートコポリマーを含む、シロップコポリマー組成物となる、請求項14に記載の方法。
- 工程a)の前記モノマー混合物が完全に重合されて、THAコポリマーとなる、請求項14に記載の方法。
- 前記組み合わせる工程b)がメルトブレンドする工程である、請求項14又は15に記載の方法。
- 前記メルトブレンドする工程が押出成形機内で行われる、請求項17に記載の方法。
- 基材と、該基材の表面上にある、請求項1〜13のいずれか一項に記載の硬化性組成物の層とを含む、接着剤物品。
- 前記組成物が部分的に硬化している、請求項19に記載の接着剤物品。
- 剥離ライナーを更に備える、請求項19に記載の接着剤物品。
- 請求項1〜13のいずれか一項に記載の硬化性組成物の層をその表面上に有する基材を提供する工程と、前記硬化性接着剤層を化学線で露光して硬化を開始させる工程と、第1の前記基材を第2の基材へと貼り付ける工程と、任意で結合した前記基材を加熱する工程と、を含む結合方法。
- 増感剤を更に含む、請求項1〜13のいずれか一項に記載の硬化性組成物。
- 前記増感剤が、ケトン、クマリン染料、キサンテン染料、アクリジン染料、チアゾール染料、チアジン染料、オキサジン染料、アジン染料、アミノケトン染料、ポルフィリン、芳香族多環式炭化水素、p−置換アミノスチリルケトン化合物、アミノトリアリールメタン、メロシアニン、スクアリリウム染料、及びピリジニウム染料から選択される、請求項23に記載の硬化性組成物。
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EP (2) | EP3320053B1 (ja) |
JP (2) | JP6837443B2 (ja) |
KR (1) | KR20180015215A (ja) |
CN (2) | CN111500227B (ja) |
TW (1) | TWI713529B (ja) |
WO (1) | WO2016195970A1 (ja) |
Families Citing this family (30)
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US10676655B2 (en) * | 2015-06-04 | 2020-06-09 | 3M Innovative Properties Company | UV curable epoxy/acrylate adhesive composition |
KR20180015717A (ko) | 2015-06-04 | 2018-02-13 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 차량 유리에 기계설비를 접합하는 방법 |
US10758456B2 (en) | 2015-11-06 | 2020-09-01 | 3M Innovative Properties Company | Redox polymerizable composition with photolabile transition metal complexes |
EP3370681A1 (en) | 2015-11-06 | 2018-09-12 | 3M Innovative Properties Company | Redox polymerizable dental composition with photolabile transition metal complexes |
WO2017095704A1 (en) | 2015-12-03 | 2017-06-08 | 3M Innovative Properties Company | Redox polymerizable composition with photolabile reducing agents |
CN108430699B (zh) | 2015-12-30 | 2023-06-23 | 3M创新有限公司 | 磨料制品和相关方法 |
WO2017117356A1 (en) | 2015-12-30 | 2017-07-06 | 3M Innovative Properties Company | Abrasive article |
CN108473822B (zh) | 2015-12-30 | 2021-11-12 | 3M创新有限公司 | 双阶段结构粘结粘合剂 |
JP7099791B2 (ja) | 2016-12-02 | 2022-07-12 | スリーエム イノベイティブ プロパティズ カンパニー | 多層接着剤物品 |
WO2018106587A1 (en) | 2016-12-07 | 2018-06-14 | 3M Innovative Properties Company | Flexible abrasive article |
CN106832103B (zh) * | 2017-01-05 | 2019-02-19 | 无锡海特新材料研究院有限公司 | 一种强力粘接pc基材的丙烯酸酯压敏胶及其制备方法 |
US11370940B2 (en) | 2017-05-24 | 2022-06-28 | 3M Innovative Properties Company | Adhesive article and methods of making and using the same |
WO2019003138A1 (en) * | 2017-06-30 | 2019-01-03 | 3M Innovative Properties Company | PRINTABLE CURABLE MIXTURES AND CURED COMPOSITIONS |
CN111448031B (zh) | 2017-12-08 | 2022-04-26 | 3M创新有限公司 | 磨料制品 |
JP7466464B2 (ja) * | 2018-06-01 | 2024-04-12 | スリーエム イノベイティブ プロパティズ カンパニー | アクリル-エポキシ接着剤組成物 |
CN108690355B (zh) * | 2018-06-26 | 2021-05-14 | 浙江三元电子科技有限公司 | 一种柔性热传导片及其制备方法 |
CN110643286B (zh) * | 2018-06-27 | 2021-11-19 | 3M创新有限公司 | Uv固化组合物及包含该组合物的胶膜、胶带和粘结构件 |
KR102050273B1 (ko) | 2019-02-20 | 2019-12-02 | (주)삼명테크 | 2-액형 에폭시 접착제 조성물 |
CN111394028A (zh) * | 2019-05-08 | 2020-07-10 | 枚林优交(上海)新材料开发有限公司 | 光激活延迟热固化胶黏剂及其制备方法 |
DE102019004662A1 (de) * | 2019-07-05 | 2021-01-07 | Lohmann Gmbh & Co. Kg | Komprimierbarer, UV- oder thermisch aktivierbarer (semi-) struktureller Klebefilm mit Farbumschlag jeweils nach Aktivierung und Aushärtung |
EP4010446A4 (en) * | 2019-08-07 | 2023-08-09 | 3M Innovative Properties Company | UV-CURRABLE ADHESIVE COMPOSITION AND ADHESIVE FILM, ADHESIVE TAPE AND CONNECTING COMPONENT THERETO |
CN114746988A (zh) | 2019-12-04 | 2022-07-12 | 3M创新有限公司 | 包括微图案并使用部分固化以粘附管芯的电路 |
EP3916065A1 (en) | 2020-05-25 | 2021-12-01 | 3M Innovative Properties Company | Curable precursor of a structural adhesive composition |
CN112029458B (zh) * | 2020-08-17 | 2022-04-15 | 南京施瓦乐新材料科技有限公司 | 一种温控变色玻璃用粘合剂及其制备方法 |
EP4050048A1 (en) | 2021-02-25 | 2022-08-31 | 3M Innovative Properties Company | Preparation of a structural tape-from-paste (tfp) adhesive with blue light (visible) initiated b-stage cure |
WO2023105327A1 (en) | 2021-12-06 | 2023-06-15 | 3M Innovative Properties Company | Adhesives comprising cyclic imide addition-fragmentation and adhesion agents |
WO2023111715A1 (en) | 2021-12-16 | 2023-06-22 | 3M Innovative Properties Company | Compositions comprising cleavable crosslinkers |
WO2024003637A1 (en) * | 2022-06-29 | 2024-01-04 | 3M Innovative Properties Company | Curable adhesive and articles for bonding pavement and concrete |
WO2024074908A1 (en) | 2022-10-03 | 2024-04-11 | 3M Innovative Properties Company | Adhesive composition comprising polar (meth)acrylate monomer and epoxy resin, articles and methods |
EP4361229A1 (en) | 2022-10-31 | 2024-05-01 | 3M Innovative Properties Company | Multilayer pre-crosslinked structural adhesive tape |
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CN103087640A (zh) * | 2011-11-08 | 2013-05-08 | 汉高股份有限公司 | 双固化粘合剂组合物及其用途以及粘合基底的方法 |
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CN108473822B (zh) | 2015-12-30 | 2021-11-12 | 3M创新有限公司 | 双阶段结构粘结粘合剂 |
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2016
- 2016-05-13 US US15/574,877 patent/US10676655B2/en active Active
- 2016-05-13 KR KR1020187000037A patent/KR20180015215A/ko unknown
- 2016-05-13 CN CN202010364933.4A patent/CN111500227B/zh active Active
- 2016-05-13 CN CN201680032350.3A patent/CN107709497B/zh active Active
- 2016-05-13 EP EP16736644.2A patent/EP3320053B1/en active Active
- 2016-05-13 WO PCT/US2016/032419 patent/WO2016195970A1/en active Application Filing
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CN111500227A (zh) | 2020-08-07 |
TW201708373A (zh) | 2017-03-01 |
JP7012794B2 (ja) | 2022-01-28 |
US20180127625A1 (en) | 2018-05-10 |
WO2016195970A1 (en) | 2016-12-08 |
US11370944B2 (en) | 2022-06-28 |
EP3320053B1 (en) | 2020-06-17 |
EP3733808A1 (en) | 2020-11-04 |
CN111500227B (zh) | 2022-04-22 |
JP6837443B2 (ja) | 2021-03-03 |
KR20180015215A (ko) | 2018-02-12 |
CN107709497B (zh) | 2020-07-17 |
EP3320053A1 (en) | 2018-05-16 |
CN107709497A (zh) | 2018-02-16 |
TWI713529B (zh) | 2020-12-21 |
US10676655B2 (en) | 2020-06-09 |
JP2020200473A (ja) | 2020-12-17 |
US20200270492A1 (en) | 2020-08-27 |
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