JP2018520215A - アクリルポリマーに基づくuv硬化性接着剤 - Google Patents
アクリルポリマーに基づくuv硬化性接着剤 Download PDFInfo
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- JP2018520215A JP2018520215A JP2017557174A JP2017557174A JP2018520215A JP 2018520215 A JP2018520215 A JP 2018520215A JP 2017557174 A JP2017557174 A JP 2017557174A JP 2017557174 A JP2017557174 A JP 2017557174A JP 2018520215 A JP2018520215 A JP 2018520215A
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- hot melt
- adhesive
- pressure sensitive
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Classifications
-
- 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
- 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
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
-
- 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
-
- 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
- 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
-
- 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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- 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
- C09J4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00
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- C—CHEMISTRY; METALLURGY
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- 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
-
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- 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
- C09J2203/00—Applications of adhesives in processes or use of adhesives in the form of films or foils
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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
- C09J2301/00—Additional features of adhesives in the form of films or foils
- C09J2301/30—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier
- C09J2301/302—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier the adhesive being pressure-sensitive, i.e. tacky at temperatures inferior to 30°C
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- C09J2301/00—Additional features of adhesives in the form of films or foils
- C09J2301/30—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier
- C09J2301/304—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier the adhesive being heat-activatable, i.e. not tacky at temperatures inferior to 30°C
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- C09J2301/40—Additional features of adhesives in the form of films or foils characterized by the presence of essential components
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Abstract
Description
a)少なくとも1つの共有結合型UV−反応性基を含むUV硬化性アクリルポリマー、ここで、前記少なくとも1つの共有結合型UV−反応性基はベンゾフェノンである、および、
b)カチオン性光開始剤
を含んでなるUV硬化性接着剤組成物に関する。
−前記組成物を基材上にコーティングすること;および、
−コーティングされた組成物を、200〜600nm、より好ましくは360〜410nmの範囲の波長を有する紫外線に暴露すること
を含む方法に関する。
本明細書中で使用される場合、用語「含む(comprising)」、「含む(comprises)」および「含む(comprised of)」は、「含む(including)」、「含む(includes)」または「含む(containing)」、「含む(contains)」などと同義語であり、これらは包括的でありまたは制限がなく、付加的な、列挙されていない構成、要素または他の工程を排除しない。
数値の端点の記載には、それぞれの範囲内に包含される全ての数および少数並びに記載された端点が含まれる。
a)少なくとも1つの共有結合型UV−反応性基を含むUV硬化性アクリルポリマー、および、
b)カチオン性光開始剤
を含んでなるUV硬化性接着剤組成物を提供する。
−前記組成物を基材上にコーティングすること;および、
−コーティングされた組成物を、200〜600nm、より好ましくは360〜410nmの範囲の波長を有する紫外線に暴露すること
を含む方法に関する。
典型的なHMPSA組成物を、以下のようにして、約100gのスケールで調製した。アクリルポリマーを溶融するまでオーブン中で130℃に加熱した。完全に混合した後、光開始剤をアクリルポリマーと混合した。次いで、増感剤を添加した。上記を完全に混合した後、不飽和オリゴマーを加えて混合した。混合工程で試料に大量の空気が混入した場合、真空デシケータに入れて封じ込められた空気を除去した。次いで、試料をシリコーン紙上に50gsm(グラム/平方メートル)の膜としてコーティングし、その後前記フィルムをポリエチレンテレフタレート(PET)の裏地紙〔Mylar(登録商標)、DuPont〕に積層した。他に定義されていない限り、試料はPhoseon UV−LED Firefly air(395nmの波長を有する8W出力により冷却され、power Puk deviceにより測定した際のUVA線量は1J/cm2である)を用いて硬化した。試料をLED源の放射窓から3cmの距離に置き、3秒間硬化させた。
実施例における剥離接着力は、テープの幅25mm当たりのニュートンで表した。用いた装置は、標準FINAT 2Kgゴム被覆ローラーと標準Instron引張試験機を備えていた。以下の手順を用いた:標準FINAT法に従い、ステンレス鋼パネル(Rocholl GmbH製)を洗浄した。ステンレス鋼パネルを使用する前に、水がステンレス鋼パネル上を滑らかに流れるまで、タップの下、試験パネルの長さに沿って400gritの防水性乾湿研磨紙を用いて研磨した。その後、水ですすぎ、乾燥させ、酢酸エチルで洗浄し、気候室内で少なくとも1時間調整した。
各試験片から裏地紙を除去し、接着剤側を下にして、清浄した試験プレート上に軽い指圧で置いた後、標準2Kg FINAT試験ローラーを毎秒約10mmの速度で各方向に2回転がした。試験片を2分間に1個の割合で試験プレートに適用した後、第1試験片が20分または24時間経過するまで試験片放置した。
AF:接着不良またはきれいな剥離:試験片が、残留物を残すことなく試験プレートから分離される。
CF:凝集破壊:接着フィルムは凝集して分離し、試験片および試験プレート上に残留物が残る。
AT:接着剤転写:接着フィルムが試験プレート上に残り、PETフィルムからきれいに除去される。
A−204、acResin A204、結合型PI基を有するアクリルポリマー、BASF製
A−260、acResin A260、結合型PI基を有するアクリルポリマー、BASF製
SR−355:不飽和オリゴマー、Sartomer製
SR−399:不飽和オリゴマー、Sartomer製
Irgacure 819:従来のフリーラジカル光開始剤、BASF製
Irgacure 250:ジアリールヨードニウム塩、従来のカチオン性光開始剤、BASF製
IHT 436:トリアリールスルホニウム塩、従来のカチオン性光開始剤、IHT製
Uvicure 2257:従来のカチオン光開始剤、Ney York Fine Chemicals製
SC−ITX:Speedcure ITX、増感剤、Lamsbon製
SC−DETX:Speedcure DETX、増感剤、Lamsbon製
比較例C−2により示されるように、結合型PI基を有するアクリルポリマーへの不飽和オリゴマーの添加は、架橋を実質的に改善しなかった。
比較例C−3により示されるように、HMPSA C−2への従来のフリーラジカル光開始剤の添加は、架橋を改善したが有意ではなかった。
比較例C−4は、従来のフリーラジカル光開始剤に増感剤を添加しても架橋が改善されないことを示している。
SAFTおよびSHEARに関する最良の接着性能は、従来のフリーラジカル光開始剤の代わりに従来のカチオン性光開始剤を増感剤と共に添加して使用した実施例I5により達成された。
Claims (13)
- a)少なくとも1つの共有結合型UV−反応性基を含むUV硬化性アクリルポリマー、ここで、前記少なくとも1つの共有結合型UV−反応性基はベンゾフェノンである、および、
b)カチオン性光開始剤
を含んでなるUV硬化性接着剤組成物。 - 前記UV硬化性アクリルポリマーが、脂環式エポキシドおよびオキセタンから選択される共有結合型反応性官能基を本質的に含まない、請求項1に記載の組成物。
- 組成物の総重量に対して0.01〜5重量%、好ましくは0.01〜1重量%、より好ましくは0.4〜0.7重量%のカチオン性光開始剤を含む、請求項1または2に記載の組成物。
- カチオン光開始剤が、ジアリールヨードニウム塩、トリアリールスルホニウム塩、ジアルキルフェニルスルホニウム塩、ジアルキル(ヒドロキシジアルキルフェニル)スルホニウム塩およびフェロセニウム塩からなる群から選択される、請求項1〜3のいずれかに記載の組成物。
- 組成物の総重量に基づいて、好ましくは0.01〜5重量%、より好ましくは0.01〜1.5重量%、最も好ましくは0.2〜0.6重量%の少なくとも1種の光増感剤をさらに含む、請求項1〜4のいずれかに記載の組成物。
- 前記少なくとも1種の光増感剤が、2,4−ジエチル−9H−チオキサンテン−9−オン、2−イソプロピルチオキサントン、9,10−ジブトキシアントラセンおよびそれらの混合物からなる群から選択される、請求項1〜5のいずれかに記載の組成物。
- 組成物の総重量に基づいて、好ましくは0.01〜20重量%、より好ましくは5〜10重量%の少なくとも1つの不飽和オリゴマーをさらに含む、請求項1〜6のいずれかに記載の組成物。
- 前記少なくとも1つの不飽和オリゴマーが、ジペンタエリスリトールペンタアクリレート、ジトリメチロールプロパンテトラアクリレート、ペンタエリスリトールテトラアクリレートおよびそれらの混合物からなる群から好ましくは選択される、請求項1〜7のいずれかに記載の組成物。
- 組成物がホットメルト組成物である、請求項1〜8のいずれかに記載の組成物。
- 請求項1〜9のいずれかに記載の組成物を硬化させる方法であって、
−前記組成物を基材上にコーティングすること;および、
−コーティングされた組成物を、200〜600nm、より好ましくは360〜410nmの範囲の波長を有する紫外線に暴露すること
を含む方法。 - 請求項1〜9のいずれかに記載の組成物の硬化生成物を含むホットメルト感圧接着剤であって、前記組成物が基材上にコーティングされ、次いで200〜600nm、より好ましくは360〜410nmの範囲の波長の紫外線に暴露される、ホットメルト感圧接着剤。
- 接着剤が、少なくとも1種の可塑剤をさらに含む、請求項11に記載のホットメルト感圧接着剤。
- テープ、医療用テープ、ラベルまたは転写フィルムにおける、請求項11または12に記載のホットメルト感圧接着剤の使用。
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PCT/EP2016/060140 WO2016177861A1 (en) | 2015-05-07 | 2016-05-06 | Uv curable adhesives based on acrylic polymers |
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MX2018009967A (es) | 2016-02-19 | 2018-11-09 | Avery Dennison Corp | Metodos en dos etapas para procesar adhesivos y composiciones relacionadas. |
WO2018081268A1 (en) | 2016-10-25 | 2018-05-03 | Avery Dennison Corporation | Block polymers with photoinitiator groups in backbone and their use in adhesive compositions |
US11590739B2 (en) | 2017-11-29 | 2023-02-28 | Sika Technology Ag | Sealing tape with a functional layer |
EP3830153B1 (en) | 2018-08-03 | 2022-08-03 | Merck Patent GmbH | A composition |
CN109111878B (zh) * | 2018-08-21 | 2020-12-11 | 深圳市广业电子科技有限公司 | 一种无溶剂紫外光双重固化热熔压敏胶 |
US20210043997A1 (en) * | 2019-08-05 | 2021-02-11 | Agc Automotive Americas R&D, Inc. | Window assembly with solderless electrical connector |
CN114174458B (zh) * | 2019-08-07 | 2023-07-04 | 3M创新有限公司 | 可uv固化粘合剂组合物和粘合剂膜、粘合带及包含它们的粘结组件 |
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WO2023208833A1 (en) * | 2022-04-29 | 2023-11-02 | Henkel Ag & Co. Kgaa | Uv led curable hotmelt pressure sensitive adhesive composition |
EP4375308A1 (en) * | 2022-11-28 | 2024-05-29 | Henkel AG & Co. KGaA | Uv led curable hotmelt pressure sensitive adhesive composition |
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US20180051194A1 (en) | 2018-02-22 |
EP3091043B1 (en) | 2019-07-03 |
CN107532042A (zh) | 2018-01-02 |
JP6810054B2 (ja) | 2021-01-06 |
US10711166B2 (en) | 2020-07-14 |
WO2016177861A1 (en) | 2016-11-10 |
BR112017017827A2 (pt) | 2018-04-10 |
EP3091043A1 (en) | 2016-11-09 |
CN107532042B (zh) | 2021-06-01 |
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