JP6359199B2 - 保護された光架橋剤由来のアクリル系接着剤組成物 - Google Patents
保護された光架橋剤由来のアクリル系接着剤組成物 Download PDFInfo
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- JP6359199B2 JP6359199B2 JP2017543777A JP2017543777A JP6359199B2 JP 6359199 B2 JP6359199 B2 JP 6359199B2 JP 2017543777 A JP2017543777 A JP 2017543777A JP 2017543777 A JP2017543777 A JP 2017543777A JP 6359199 B2 JP6359199 B2 JP 6359199B2
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Classifications
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- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
- C07C69/533—Monocarboxylic acid esters having only one carbon-to-carbon double bond
- C07C69/54—Acrylic acid esters; Methacrylic acid esters
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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
- C08F2/00—Processes of polymerisation
- 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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- 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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- 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
- C08F220/12—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
-
- 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
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- C08F220/1808—C8-(meth)acrylate, e.g. isooctyl (meth)acrylate or 2-ethylhexyl (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
- 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
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- C08F220/30—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety
- C08F220/302—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety and two or more oxygen atoms in the alcohol moiety
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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
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- C08K5/0025—Crosslinking or vulcanising agents; including accelerators
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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
- C08K5/04—Oxygen-containing compounds
- C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
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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
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- C08K5/16—Nitrogen-containing compounds
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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
Landscapes
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- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Adhesives Or Adhesive Processes (AREA)
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- Polymerisation Methods In General (AREA)
Description
感圧テープは、家庭及び職場の実質的には至る所に存在する。その最も簡単な構成において、感圧テープは接着剤及びバッキングを備え、その全体構造は使用温度で粘着性を有し、適度な圧力のみによって各種の基材に接着して結合を形成する。このようにして、感圧テープは、完全で自己完結型の接着系を構成する。
本開示は、モノマー混合物に加えることができ、生成するポリマー中に組み込まれる、新規の保護された光架橋剤を提供する。これらの保護された光架橋剤は、後に脱保護し、ポリマーを架橋することができる。
「(メタ)アクリレート」又は「アクリル」は、アクリレート、メタクリレート又はこれらの組み合わせを簡略に指し、「(メタ)アクリル」は、アクリル、メタクリル又はこれらの組み合わせを簡略に指し、「(メタ)アクリロイル」は、アクリロイル、メタクリロイル又はこれらの組み合わせを簡略に指すものである。
保護された光架橋剤は、式:
(式中、
R1はH又はCH3であり、
X1及びX2のそれぞれは−O−又は−NR1−であり、
R2は二価の(ヘテロ)ヒドロカルビル基であり、
下付き文字aは0又は1であり、
Zは、脱保護された際にノリッシュI型又はII型開裂を受け、かつアクリル系ポリマーを架橋する、カルボニルが保護された発色団である)のものである。
[式中、Arは、より低級の1〜6個の炭素原子を有するアルキル基によって置換され得る、5〜18個の炭素原子を有するアリーレン基であり、1〜3個のヘテロ原子を含んでもよく、Arは、好ましくは、フェニレン、ナフタレン及びビフェニレンから選択され、
Protは、ケタール等の、カルボニル上の保護基であり、
R4は、水素、C1〜C12アルキル基、C1〜C12アルコキシ基及びフェニル基からなる群から選択され、
R5、R6及びR8は、独立して、ヒドロキシル基、C1〜C12アルキル基、C1〜C12アルコキシ基、ジ(C1〜C12アルキル置換)アミノ基及びアリール基からなる群から選択され、ただし、R5、R6及びR8のうちの少なくとも1つは、ヒドロキシル基、C1〜C12アルコキシ基若しくはジC1〜C12アルキル置換アミノ基からなる群から選択される、又は、R5、R6及びR8のうちのいずれか2つは、共に、アルキレン基、−(CqH2q)−、若しくはアルキレン−ジオキシ基、−O−(CqH2q)−O−(式中、qは2又は3の値である整数である)とすることができ、これらの基が結合した炭素原子と共に5員環若しくは6員環を形成し、又は、R5、R6及びR8のうちのいずれか2つは、これらの基が結合した炭素原子と共にカルボニル基−CO−を形成することができ、ただし、残りのR5、R6及びR8は、ヒドロキシル基、C1〜C12アルコキシ基、ジC1〜C12アルキル置換アミノ基及びアリール基からなる群から選択される]を有する、保護された光活性(感放射線)基から選択される。
再描画
式中、X3は、HX1−によって置換され得る、ハライド又はアルコキシ等の脱離基であり、
X1及びX2は、独立して、−O−又は−NH−であり、
R2は、2〜10個の炭素原子の二価のアルキレン又は−(R3)2C(CH2)m(CO)OR9−(式中、mは0又は1であり、R3はH又はC1〜C4アルキル基であり、かつR9はC2〜C6アルキレンである)であり、
R1はH又はCH3であり、かつ
Zは光架橋基である。
ベンゾフェノン光架橋剤は、以下の式(式中、−X1−(R2−X2)a−結合は示さず):
(式中、各R1は、独立して、C1〜C12アルキル、C1〜C12アルキルオキシ、C1〜C12アルキルチオ、アリール、アリールオキシ、アリールチオ、ニトリル及びハライドから選択される)のものであり得る。
(式中、各R1は、独立して、C1〜C12アルキル、C1〜C12アルキルオキシ、C1〜C12アルキルチオ、アリール、アリールオキシ、アリールチオ、ニトリル及びハライドから選択され、かつnは0〜4である)のものである。
(式中、各R1は、独立して、C1〜C12アルキル、C1〜C12アルキルオキシ、C1〜C12アルキルチオ、アリール、アリールオキシ、アリールチオ、ニトリル及びハライドから選択され、かつnは0〜4である)のものである。
a)50〜99重量部の(メタ)アクリレートエステルモノマーと、
b)1〜50重量部の極性モノマー(酸官能性モノマーを含む)と、を含み得、
モノマーの合計は100重量部である。
a)50〜99重量部の(メタ)アクリレートエステルモノマーと、
b)1〜15重量部の酸官能性モノマーと、
c)0〜50重量部未満の極性モノマー(酸官能性モノマーを除く)と、を含み、
モノマーの合計は100重量部である。
−(Mester)b−(Macid)c−(Mpolar)d−(MPX*)e− → −(Mester)b−(Macid)c−(Mpolar)d−(MPX)e−
(式中、
Mesterは、(メタ)アクリレートモノマー由来の重合モノマー単位を表し、
Macidは、酸官能性モノマー由来の重合モノマー単位を表し、
Mpolarは、非酸官能性極性モノマー由来の重合モノマー単位を表し、
MPX*は、保護された光架橋剤モノマー由来の重合モノマー単位を表し、
MPXは、脱保護された光架橋剤モノマー由来の重合モノマー単位を表し、かつ
下付き文字b、c、d及びeは、前述のコポリマー中の各モノマーの重量部を表す。)
1)モノマー混合物を光重合し、ペンダントの、保護された光架橋基を有する溶質コポリマーを含むシロップポリマー組成物を提供する工程と、
2)シロップを熱重合し、コポリマー組成物を生成する工程であり、光架橋基が脱保護される、工程と、
3)任意に実施される工程であり、工程2)のコポリマー組成物をコーティングする工程と、
4)コポリマー組成物を光架橋する工程と、を含む、接着剤を調製する方法を提供する。
接着剤剪断強度の測定
剪断力試験は、実施例において調製された接着テープの12.7ミリメートル(mm)幅の試料を使用して実施した。ステンレス鋼パネルを、アセトンで拭き取ることによって洗浄し、空気乾燥させた。接着テープの試料を、各接着テープの25.4mm×25.4mm部分がパネルに密着し、各接着テープの1つの末端は解放されている(すなわち、パネルに付着されていない)ように、パネルに適用した。1000gの重りを接着テープ試料の解放末端に装着し、パネルが、伸長された解放末端及び重りと180°の角度を形成するように、パネルをラックに保持した。試験は約70℃で実施し、各接着テープが試験パネルから分離するまでの経過時間を分単位で、剪断強度として記録した。経過時間が10000分を超えた場合、経過時間は>10000分として記録した。2回の剪断力試験を各接着テープ試料について実施し、結果を平均化した。
剥離接着力は、実施例において調製された接着テープを使用して測定した。ステンレス鋼パネルを、アセトンで拭き取ることによって洗浄し、乾燥させた。幅12.7mm、長さ10〜12cmの大きさの接着テープを、2kgの硬質ゴムローラーで2回ローリングすることによって、パネルに接着した。接着テープの解放末端を、除去の角度が180°となり、接着試験スケール(SLIP/PEEL TESTER MODEL 3M90、Instrumentors Inc.(Strongsville,OH,USA)より入手)の水平アームに装着されるように、折り返した。ステンレス鋼プレートを、1分当たり12インチ(1分当たり30.5cm)の速度でスケールから遠ざかるプラットホームに装着した。剥離試験は、接着テープを試験パネルに適用した直後に開始した。試験中、スケールをオンス単位で、安定化された剥離力の平均として読み取った。続いて、数字を変換し、デシメーター当たりのニュートン(N/dm)として報告した。3回の剥離試験を各サンプルに対して実施し、平均値を求め、剥離力の報告値を得た。
ポリマーの試料(〜0.30g)を、あらかじめ重量を測定した矩形メッシュ(4インチ×2.5インチ(〜10cm×6.4cm))の中央に置いた。メッシュは、MCNICHOLS QUALITY WIRE MESH(平織り、ステンレス鋼304型、織布構成体、325mesh、0.0014インチ(〜36μm)のワイヤ、0.0017インチ(〜43μm)の開口部)であった。メッシュの突出部を内側に折り畳み、メッシュの内側にテープを包み込んで固定化した。ポリマーを包んで折り畳んだメッシュを、ガラス製広口瓶内のトルエン30mL中に24時間浸漬した。続いて接着剤を有するメッシュを広口瓶から取り出し、オーブン中で30分間、120℃で乾燥し、再度重量を測定し、試料の質量を算出した。ポリマーのゲル化した不溶性部分を、以下の式を使用し、ゲル重量パーセント(「ゲル重量%」)として算出した。
本明細書に報告した固有粘度(IV)は、当業者によって使用される、従来法によって得た。IVは、27℃に調整した水浴中でLauda粘度計を使用し、ポリマー溶液(酢酸エチル中のポリマー1デシリットル当たり0.3g)10mLの流速を測定して得た。準拠した試験手順及び使用した装置については、Textbook of Polymer Science,F.W.Billmeyer,Wiley−Interscience,Second Edition,1971、84及び85ページに詳述されている。
試験材料の試料(〜0.5〜2.0g)を小型のスズ製の開放容器にとり、対流オーブン中に約105℃で終夜保存した。蒸発したモノマーの重量減少の測定値により、ポリマーに変換されたモノマーの量を算出し、重量パーセント(重量%)として表示した。
25等量のMeOH、1.5等量のオルトギ酸トリメチル及び20mMのTFAとの反応によってAEBPをケタール化し、対応するジメチルケタール(「KAEBP」)を生成した。反応混合物を24時間還流した後、ロータリーエバポレーターで乾燥状態まで留去した。粗生成物の1H NMRは3.01ppmにメトキシ基のピークを示し、生成物における7.47ppmのピークに対する出発物質における7.85ppmの芳香族水素の組の比によって、ケトンからケタールへの93.9%の変換を示した。粗KAEBP生成物の一部をシリカゲルカラムで精製し、KAEBPを粘性の液体として得た。
表2に示した相対量を使用して、IOA、AA、IOTG及びIRG651を広口瓶中でブレンドすることにより、溶液を調製した。広口瓶中の混合物に、磁気撹拌子を加え、混合物を撹拌プレート上に定置して混合し、硬化性組成物を形成した。EVAフィルムを熱融着し、それぞれが18cm×5cmの大きさの、開放型の受け部を形成した。各受け部に、約26gの硬化性組成物を充填した。空気を開放端から押し出した後、J.J.Elemer Corp.(St.Louis,MO,USA)の「MIDWEST PACIFIC IMPULSE SEALER」を使用して、開放端を熱融着した。EVAフィルム内に包まれた硬化性組成物を、一定温度の17℃の水浴中に浸漬し、紫外線(365nm、4mW/cm2)で各面に対して8分間ずつ照射し、硬化性組成物を重合させた。
比較例2は、比較例2に使用した手順に従って作製した。ただし、材料の量は表2においてCE−2について示したとおりであり、0.25重量部のAEBPを含んだ。
実施例2は、比較例1に使用した手順に従って作製した。ただし、材料の量は表2においてEX−2について示したとおりであり、0.25重量部のKAEBPを含んだ。プロトンNMRは、3.01ppmのメトキシのシグナルが依然として存在していることを示した。
実施例3は、比較例1に使用した手順に従って作製した。ただし、材料の量は表2においてEX−3について示したとおりであり、0.35重量部のKAEBPを含んだ。
Claims (12)
- アクリル系接着剤組成物用の光架橋剤であって、
式:
(式中、
R1はH又はCH3であり、
X1及びX2のそれぞれは−O−又は−NR1−であり、
R2は二価の(ヘテロ)ヒドロカルビル基であり、
下付き文字aは0又は1であり、
Zは、アセトフェノン、ベンゾフェノン、アントラキノン、9−フルオレノン、アントロン、キサントン、チオキサントン、アクリドン、ジベンゾスベロン、ベンジル、クロモン、ベンゾイルシクロヘキサン、ベンゾイルピペリジン、ベンゾイルピペラジン、ベンゾイルモルホリン、ベンゾイルtert−アルキレン及びベンゾイル−tert−ヒドロキシアルキレン由来の、カルボニルが保護された基から選択される、カルボニルが保護された光架橋基である)の、保護された光架橋剤。 - Protが、環状若しくは非環状ケタール、ジチオケタール、O−置換シアノヒドリン、置換ヒドラゾン、オキサゾリジン、イミダゾリジン及びチアゾリジン保護基から選択される、請求項1に記載の保護された光架橋剤。
- アクリル系接着剤組成物用の重合性組成物であって、
少なくとも1種の(メタ)アクリレートモノマーと、光開始剤と、請求項1〜3のいずれか一項に記載の保護された光架橋剤を含む、重合性組成物。 - a)50〜99重量部の(メタ)アクリレートエステルモノマーと、
b)1〜50重量部の極性モノマー(酸官能性モノマーを含む)と、を含み、
前記モノマーの合計が100重量部である、請求項4に記載の重合性組成物。 - 前記(メタ)アクリレートモノマーが、
a)50〜99.9重量部の(メタ)アクリレートエステルモノマーと、
b)0.1〜15重量部の酸官能性モノマーと、
c)0〜50重量部未満の極性モノマー(酸官能性モノマーを除く)と、を含み、
前記モノマーの合計が100重量部である、請求項5に記載の重合性組成物。 - a)少なくとも1種の(メタ)アクリレートモノマーと、光開始剤と、請求項1〜3のいずれか一項に記載の保護された光開始剤と、のモノマー混合物を光重合する工程と、
b)前記保護された光架橋剤を脱保護する工程と、
c)得られたコポリマーを光架橋する工程と、を含む、アクリル系接着剤組成物を調製する方法。 - 第1の光重合工程の前記モノマー混合物が、非架橋コポリマーへと完全に変換される、請求項7に記載の方法。
- 第1の光重合工程の前記モノマー混合物が、非架橋コポリマーへと最大30%変換される、請求項7又は8に記載の方法。
- 工程a)の生成物が、ペンダントの、保護された光架橋基を有する(メタ)アクリレートコポリマーである、請求項7〜9のいずれか一項に記載の方法。
- 1)モノマー混合物を光重合し、ペンダントの、保護された光架橋基を有する溶質コポリマーを含むシロップポリマー組成物を提供する工程と、
2)前記シロップポリマー組成物を熱重合し、コポリマー組成物を生成する工程であり、前記光架橋基が脱保護される、工程と、
3)任意に実施される工程であり、工程2)の前記コポリマー組成物をコーティングする工程と、
4)前記コポリマー組成物を、紫外線への露出によって光架橋する工程と、を含む、請求項7〜10のいずれか一項に記載の方法。 - アクリル系接着剤組成物用のコポリマーであって、
式:
−(Mester)b−(Macid)c−(Mpolar)d−(MPX*)e−
(式中、
Mesterは、(メタ)アクリレートモノマー由来の重合モノマー単位を表し、
Macidは、酸官能性モノマー由来の重合モノマー単位を表し、
Mpolarは、非酸官能性極性モノマー由来の重合モノマー単位を表し、
MPX*は、請求項1〜3のいずれか一項に記載の保護された光架橋剤モノマー由来の重合モノマー単位を表し、かつ
下付き文字b、c、d及びeは、コポリマー中の各モノマーの重量部を表す)のコポリマーであり、
100重量部のモノマー混合物に対し、
a)50〜99.9重量部の(メタ)アクリレートエステルモノマーと、
b)0.1〜15重量部の酸官能性モノマーと、
c)0〜50重量部未満の極性モノマー(酸官能性モノマーを除く)と、
d)0.05〜0.5重量部の前記保護された光架橋剤と、
を含む、コポリマー。
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Family Cites Families (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4304705A (en) | 1980-01-02 | 1981-12-08 | Minnesota Mining And Manufacturing Company | Radiation-curable polymers containing pendant unsaturated peptide groups derived from azlactone polymers |
US4777276A (en) | 1981-10-29 | 1988-10-11 | Minnesota Mining And Manufacturing Company | Acrylamidoacylated oligomers |
US4619979A (en) | 1984-03-28 | 1986-10-28 | Minnesota Mining And Manufacturing Company | Continuous free radial polymerization in a wiped-surface reactor |
US4843134A (en) | 1984-03-28 | 1989-06-27 | Minnesota Mining And Manufacturing Company | Acrylate pressure-sensitive adhesives containing insolubles |
US4847137A (en) | 1986-05-19 | 1989-07-11 | Minnesota Mining And Manufacturing Company | Pressure-sensitive adhesive crosslinked by copolymerizable aromatic ketone monomers |
US4903545A (en) | 1989-03-03 | 1990-02-27 | Sundstrand-Sauer | Hydrostatic transmission center section |
US5804610A (en) | 1994-09-09 | 1998-09-08 | Minnesota Mining And Manufacturing Company | Methods of making packaged viscoelastic compositions |
DE69509537T2 (de) | 1994-09-09 | 1999-09-23 | Minnesota Mining & Mfg | Verfahren zur herstellung von verpacktem hei chmelzenden klebstoff |
US5877313A (en) | 1995-05-17 | 1999-03-02 | Bristol-Myers Squibb | Benzo-fused azepinone and piperidinone compounds useful in the inhibition of ACE and NEP |
US5637646A (en) | 1995-12-14 | 1997-06-10 | Minnesota Mining And Manufacturing Company | Bulk radical polymerization using a batch reactor |
US7968661B2 (en) | 2005-12-28 | 2011-06-28 | 3M Innovative Properties Company | Method of free radically polymerizing vinyl monomers |
US20120329898A1 (en) * | 2008-04-14 | 2012-12-27 | 3M Innovative Properties Company | 2-octyl (meth)acrylate adhesive composition |
US20100151241A1 (en) * | 2008-04-14 | 2010-06-17 | 3M Innovative Properties Company | 2-Octyl (Meth)acrylate Adhesive Composition |
US7838110B2 (en) | 2008-12-02 | 2010-11-23 | 3M Innovative Properties Company | Aziridine-functional photoactive crosslinking compounds |
WO2012091817A1 (en) * | 2010-12-29 | 2012-07-05 | 3M Innovative Properties Company | Pressure-sensitive adhesives with triazine-epoxy crosslinking system |
KR20140030206A (ko) * | 2011-04-26 | 2014-03-11 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 혼합 광가교결합 시스템을 갖는 감압 접착제 |
EP2733186A1 (en) * | 2012-11-19 | 2014-05-21 | 3M Innovative Properties Company | Highly tackified acrylate pressure sensitive adhesives |
JP6537118B2 (ja) * | 2013-08-07 | 2019-07-03 | 東洋合成工業株式会社 | 化学増幅フォトレジスト組成物及び装置の製造方法 |
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- 2016-01-28 WO PCT/US2016/015331 patent/WO2016133669A1/en active Application Filing
- 2016-01-28 CN CN201680010816.XA patent/CN107250310B/zh active Active
- 2016-01-28 US US15/550,830 patent/US10189771B2/en active Active
- 2016-01-28 JP JP2017543777A patent/JP6359199B2/ja active Active
- 2016-01-28 EP EP16706927.7A patent/EP3259290B1/en active Active
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US20180029970A1 (en) | 2018-02-01 |
CN107250310A (zh) | 2017-10-13 |
EP3259290A1 (en) | 2017-12-27 |
EP3259290B1 (en) | 2018-12-12 |
WO2016133669A1 (en) | 2016-08-25 |
JP2018507300A (ja) | 2018-03-15 |
KR20170110154A (ko) | 2017-10-10 |
US10189771B2 (en) | 2019-01-29 |
CN107250310B (zh) | 2019-05-28 |
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