JP2019508522A - シリコーン系接着剤組成物及び接着剤物品 - Google Patents
シリコーン系接着剤組成物及び接着剤物品 Download PDFInfo
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- JP2019508522A JP2019508522A JP2018534628A JP2018534628A JP2019508522A JP 2019508522 A JP2019508522 A JP 2019508522A JP 2018534628 A JP2018534628 A JP 2018534628A JP 2018534628 A JP2018534628 A JP 2018534628A JP 2019508522 A JP2019508522 A JP 2019508522A
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Abstract
Description
A.ウレア系シリコーンコポリマー、オキサミド系シリコーンコポリマー、アミド系シリコーンコポリマー、ウレタン系シリコーンコポリマー、及びこれらの混合物からなる群から選択される、エラストマー性シリコーン系コポリマーと、
0重量%超かつ20重量%以下のMQ樹脂と、
を含む、接着剤組成物。
以下の式によって表されるブロックをn個、
式中、
各Rは、アルキル基、ビニル基、高級アルケニル基、シクロアルキル基、アリール基、及びフッ素含有基からなる群から選択される一価の基を独立して表し、
各Zは、アリーレン基、アルカリーレン基、アラルキレン基、アルキレン基、及びシクロアルキレン基、並びにこれらの組み合わせからなる群から選択される二価の基を独立して表し、
各Yは、アルキレン基、アルカリーレン基、アラルキレン基、アリーレン基、及びこれらの組み合わせからなる群から選択される二価の基を独立して表し、
各Dは、水素、1〜10個の炭素原子を有するアルキル基、フェニル、及びB又はYを含む環構造を完成させて複素環を形成する基からなる群から独立して選択され、
各Bは、アルキレン基、アルカリーレン基、アラルキレン基、シクロアルキレン基、アリーレン基、及びポリ(アルキレンオキシ)基、並びにこれらの組み合わせからなる群から選択される二価の基を独立して表し、
pは、少なくとも10である整数であり、
nは、少なくとも1である整数であり、かつ
mは、少なくとも1〜最大1,000以下の範囲内の整数であり、nのmに対する比は、約1:10〜約10:1の範囲内である、実施形態C〜Fのいずれか1つに記載の接着剤組成物。
各Yは独立して、アルキレン、アラルキレン、又はこれらの組み合わせであり、
Gは、式R3HN−G−NHR3のジアミンから2個の−NHR3基を引いたものに等しい二価残基であり、
R3は、水素又はアルキルであるか、あるいはR3は、G及びそれら両方が結合している窒素と一緒になって複素環式基を形成し、
nは独立して、0〜1500の整数であり、かつ
pは、1〜10の整数である、実施形態A又はBに記載の接着剤組成物。
第2の基材、及び
第1の基材と第2の基材との間に配置された感圧性接着剤
を含み、感圧性接着剤が、請求項1〜14のいずれか一項に記載の接着剤組成物を含む、接着剤アセンブリ。
本明細書において使用される場合、以下の通りであることが理解されるべきである。
各Rは、独立して、約1〜12個の炭素原子を有し、かつ例えばトリフルオロアルキル基若しくはビニル基、ビニルラジカル、若しくは式、R2(CH2)aCH=CH2(式中、R2は−(CH2)b−又は−(CH2)cCH=CH−であり、aは1、2又は3であり、bは0、3又は6であり、cは3、4又は5である)によって表される高級アルケニルラジカルで置換されていてもよいアルキル部分;約6〜12個の炭素原子を有し、かつアルキル基、フルオロアルキル基、及びビニル基で置換されていてもよいシクロアルキル部分;又は約6〜20個の炭素原子を有し、かつ例えばアルキル基、シクロアルキル基、フルオロアルキル基、及びビニル基で置換されていてもよいアリール部分である、部分であるか、あるいはRは、米国特許第5,028,679号に記載されているようなペルフルオロアルキル基、又は米国特許第5,236,997号に記載されているようなフッ素含有基、又は米国特許第4,900,474号及び同第5,118,775号に記載されているようなペルフルオロエーテル含有基であり;典型的には、R部分の少なくとも50%はメチルラジカルであり、残りは、1〜12個の炭素原子を有する一価のアルキル若しくは置換アルキルラジカル、アルケニルラジカル、フェニルラジカル、又は置換フェニルラジカルであり、
各Zは、約6〜20個の炭素原子を有するアリーレンラジカル又はアラルキレンラジカル、約6〜20個の炭素原子を有するアルキレンラジカル又はシクロアルキレンラジカルである、多価のラジカルであり、一部の実施形態では、Zは、2,6−トリレン、4,4’−メチレンジフェニレン、3,3’−ジメトキシ−4,4’− ビフェニレン、テトラメチル−m−キシリレン、4,4’−メチレンジシクロヘキシレン、3,5,5−トリメチル−3−メチレンシクロヘキシレン、1,6−ヘキサメチレン、1,4−シクロヘキシレン、2,2,4−トリメチルヘキシレン、及びこれらの混合物であり、
各Yは、独立して、1〜10個の炭素原子のアルキレンラジカル、6〜20個の炭素原子を有するアラルキレンラジカル又はアリーレンラジカルである、多価のラジカルであり、
各Dは、水素、1〜10個の炭素原子のアルキルラジカル、フェニル、及びB又はYを含む環構造を完成させて複素環を形成するラジカルからなる群から選択され、
ここで、Bは、アルキレン、アラルキレン、シクロアルキレン、フェニレン、ヘテロアルキレン、例えばポリエチレンオキシド、ポリプロピレンオキシド、ポリテトラメチレンオキシドなど、並びにこれらのコポリマー及び混合物からなる群から選択される、多価のラジカルであり、
mは、0〜約1000の数であり、
nは、少なくとも1である数であり、かつ
pは、少なくとも10、一部の実施形態では15〜約2000又は30〜1500である数である。]
特に断りの無い限り、実施例及び本明細書の残りの部分におけるすべての部、百分率、比などは、重量を基準とする。使用した溶媒及び他の試薬は、特に断りの無い限り、Sigma−Aldrich Chemical Company(Milwaukee,WI)から入手することができる。加えて、下の実施例において使用したすべての材料に関する略語及び供給元を表1に提供する。
以下の試験方法を使用して、本開示の実施例の一部について評価した。
180度(180°)剥離接着力試験を、ガラス基材(すなわち、窓ガラス)が試験に記載されているステンレス鋼基材を置換している点を除き、ASTM D 3330−90に従って実行した。
例証的接着剤物品の曇り度及び透過率は、ATM D1003−1995に従って、BYK Gardner分光光度計を用いて測定した。測定値は、タングステン電球の光の下における曇り度を表す、A2*値として報告した。
以下は、本開示によるシリコーン接着剤の調製において使用した様々なエラストマー溶液の調製例について例証するものである。
固形分20重量パーセント(重量%)の、エラストマーのトルエン/2−プロパノールの混合物[75/25(重量/重量)]中の溶液を調製した。このエラストマーは、表2に要約されているように、モル比が1/1/2のPDMSジアミン 20k/DYTEK A/H−MDIのコポリマーであった。
固形分20重量%の、エラストマーのトルエン/2−プロパノールの混合物[75/25(重量/重量)]中の溶液を調製した。このエラストマーは、表2に要約されているように、モル比が1/1/2のPDMSジアミン 33k/DYTEK A/H−MDIのコポリマーであった。
固形分20重量%の、エラストマーのトルエン/2−プロパノールの混合物[65/35(重量/重量)]中の溶液を調製した。このエラストマーは、表2に要約されているように、モル比が1/0.5/1.5のPDMSジアミン 33k/DYTEK A/H−MDIのコポリマーであった。
以下は、本開示による様々なシリコーン接着剤の調製の実施例、及び比較例について例証するものである。
EX−1〜EX−12のそれぞれについて、表3に要約したMQ樹脂の種類及び量を使用して、エラストマーA溶液のサンプル及びMQ樹脂のサンプルをジャーに秤量することで、接着剤コーティング溶液を調製した。このジャーをローラー上に置いて、内容物を1晩周囲温度で混合して、接着剤コーティング溶液を提供した。比較例1(CE−1)は、エラストマーAのみを含み、MQ樹脂は含まなかった。
EX−13〜EX−24のそれぞれについて、表5に要約したMQ樹脂の種類及び量を使用して、エラストマーB溶液のサンプル及びMQ樹脂のサンプルをジャーに秤量することで、接着剤コーティング溶液を調製した。このジャーをローラー上に置いて、内容物を1晩周囲温度で混合して、接着剤コーティング溶液を提供した。比較例2(CE−2)は、エラストマーBのみを含み、MQ樹脂は含まなかった。
EX−13〜EX−24のそれぞれについて、表7に要約したMQ樹脂の種類及び量を使用して、エラストマーC溶液のサンプル及びMQ樹脂のサンプルをジャーに秤量することで、接着剤コーティング溶液を調製した。このジャーをローラー上に置いて、内容物を1晩周囲温度で混合して、接着剤コーティング溶液を提供した。比較例3(CE−3)は、エラストマーCのみを含み、MQ樹脂は含まなかった。
Claims (32)
- ウレア系シリコーンコポリマー、オキサミド系シリコーンコポリマー、アミド系シリコーンコポリマー、ウレタン系シリコーンコポリマー、及びこれらの混合物からなる群から選択される、エラストマー性シリコーン系コポリマーと、
0重量%超かつ20重量%以下のMQ樹脂と、
を含む、接着剤組成物。 - 10重量%未満のMQ樹脂を含む、請求項1に記載の接着剤組成物。
- 前記エラストマー性シリコーン系コポリマーが、少なくとも5,000グラム/モルの分子量を有するポリジオルガノシロキサンジアミンと、ポリイソシアネートとの反応生成物である、ウレア系シリコーンコポリマーを含む、請求項1又は2に記載の接着剤組成物。
- 前記エラストマー性シリコーン系コポリマーが、少なくとも5,000g/モルの分子量を有するポリジオルガノシロキサンジアミンと、ポリアミンと、ポリイソシアネートとの反応生成物である、ウレア系シリコーンコポリマーを含む、請求項1又は2に記載の接着剤組成物。
- 前記ポリアミンが、約300g/モル以下の分子量を有する、請求項4に記載の接着剤組成物。
- 前記ポリジオルガノシロキサンジアミンが、約10,000g/モル〜約65,000g/モルの分子量を有する、請求項3〜5のいずれか一項に記載の接着剤組成物。
- 前記ウレア系シリコーンコポリマーが、
以下の式によって表されるブロックをn個
式中、
各Rは、アルキル基、ビニル基、高級アルケニル基、シクロアルキル基、アリール基、及びフッ素含有基からなる群から選択される一価の基を独立して表し、
各Zは、アリーレン基、アルカリーレン基、アラルキレン基、アルキレン基、及びシクロアルキレン基、並びにこれらの組み合わせからなる群から選択される二価の基を独立して表し、
各Yは、アルキレン基、アルカリーレン基、アラルキレン基、アリーレン基、及びこれらの組み合わせからなる群から選択される二価の基を独立して表し、
各Dは、水素、1〜10個の炭素原子を有するアルキル基、フェニル、及びB又はYを含む環構造を完成させて複素環を形成する基からなる群から独立して選択され、
各Bは、アルキレン基、アルカリーレン基、アラルキレン基、シクロアルキレン基、アリーレン基、及びポリ(アルキレンオキシ)基、並びにこれらの組み合わせからなる群から選択される二価の基を独立して表し、
pは、少なくとも10である整数であり、
nは、少なくとも1である整数であり、かつ
mは、少なくとも1〜最大1,000以下の範囲内の整数であり、nのmに対する比は、約1:10〜約10:1の範囲内である、請求項3〜6のいずれか一項に記載の接着剤組成物。 - Rがメチルであり、Zが−CH2C6H4C(CH3)2C6H4CH2−であり、Yが−CH2CH2CH2−であり、DがHであり、かつBが−CH2CH2CH2CH(CH3)−である、請求項7又は8に記載の接着剤組成物。
- 前記nのmに対する比が、約1である、請求項7〜9のいずれか一項に記載の接着剤組成物。
- 前記シリコーンポリウレアブロックコポリマーが、約10,000g/モル〜約65,000g/モルの重量平均分子量を有するポリジオルガノシロキサンジアミンと、3モル以下のポリアミンと、ポリイソシアネートとの反応生成物を含む、請求項7〜10のいずれか一項に記載の接着剤組成物。
- 前記エラストマー性シリコーン系コポリマーが、以下の式の反復単位を少なくとも2個含むアミド系シリコーンコポリマーを含み、
各Yは独立して、アルキレン、アラルキレン、又はこれらの組み合わせであり、
Gは、式R3HN−G−NHR3のジアミンから2個の−NHR3基を引いたものに等しい二価残基であり、
R3は、水素又はアルキルであるか、あるいはR3は、G及びそれら両方が結合している窒素と一緒になって複素環式基を形成し、
nは独立して、0〜1500の整数であり、かつ
pは、1〜10の整数である、請求項1又は2に記載の接着剤組成物。 - 感圧性接着剤である、請求項1〜12のいずれか一項に記載の接着剤組成物。
- 前記感圧性接着剤が、光学的に透明である、請求項13に記載の接着剤組成物。
- 基材の少なくとも一方の主表面に適用された、請求項1〜14のいずれか一項に記載の感圧性接着剤を含む、接着剤物品。
- 前記感圧性接着剤が、前記基材の少なくとも一方の主表面上に単一層を含む、請求項15に記載の接着剤物品。
- 前記基材が、硬質表面、テープ裏材、フィルム、シート、又は剥離ライナーを含む、請求項15又は16に記載の接着剤物品。
- 前記基材が、ガラス、セラミック、ポリマー、金属、木材、又はこれらの組み合わせから選択される、請求項15〜17のいずれか一項に記載の接着剤物品。
- 前記基材が、ポリマーフィルム、光学フィルム、又は剥離ライナーから選択される、請求項18に記載の接着剤物品。
- 少なくとも約90%の可視光透過率及び5%以下の曇り度を有する、請求項15〜19のいずれか一項に記載の接着剤物品。
- 伸長可能であり、かつ引き伸ばし剥離可能である、請求項15〜20のいずれか一項に記載の接着剤物品。
- 追加的な伸長可能層を更に含む、請求項21に記載の接着剤物品。
- 前記感圧性接着剤層が、約25マイクロメートル〜約300マイクロメートルの厚さを有する、請求項15〜22のいずれか一項に記載の接着剤物品。
- 前記感圧性接着剤が、少なくとも1つの構造化表面を含む、請求項15〜23のいずれか一項に記載の接着剤物品。
- 少なくとも1つの、発泡体を含む層を更に含む、請求項15〜24のいずれか一項に記載の接着剤物品。
- 85℃で7日間エージングさせた後に、約500N/dm以下の、ガラス基材に対する180°剥離接着力を呈する、請求項15〜25のいずれか一項に記載の接着剤物品。
- 第1の基材、
第2の基材、及び
前記第1の基材と前記第2の基材との間に配置された感圧性接着剤
を含み、前記感圧性接着剤が、請求項1〜14のいずれか一項に記載の接着剤組成物を含む、接着剤アセンブリ。 - 前記第1の基材及び前記第2の基材の各々が、硬質表面、テープ裏材、フィルム、シート、又は剥離ライナーを含む、請求項27に記載の接着剤アセンブリ。
- 前記第1の基材が、フルオロ熱可塑性フィルム、ポリエステルフィルム、ポリアミドフィルム、ポリ(メタ)アクリレートフィルム、ポリオレフィンフィルム、又はポリカーボネートフィルムから選択されるポリマーフィルムを含む、請求項28に記載の接着剤アセンブリ。
- 前記第2の基材が、ガラス、セラミック、陶材、ポリマー、金属、又は木材から選択される硬質表面を含む、請求項29に記載の接着剤アセンブリ。
- 前記第2の基材が、窓、車両の風防、又は電子ディスプレイデバイスを含む、請求項30に記載の接着剤アセンブリ。
- 前記第2の基材が、テレビ、コンピューターモニター、携帯電話ディスプレイ、ラップトップコンピューターディスプレイ、ノート型コンピューターディスプレイ、又はタブレットコンピューターディスプレイから選択される電子ディスプレイデバイスを含み、更に、前記感圧性接着剤が、光学的に透明であり、かつ引き伸ばし剥離可能である、請求項31に記載の接着剤アセンブリ。
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AU2019326076A1 (en) * | 2018-08-23 | 2021-03-18 | 3M Innovative Properties Company | Tackified and filled silicone adhesive compositions |
WO2020188423A1 (en) * | 2019-03-20 | 2020-09-24 | 3M Innovative Properties Company | Siloxane tackifying resin layers as adhesion promotion agents |
EP4013910B1 (en) * | 2019-08-15 | 2023-04-05 | 3M Innovative Properties Company | Core-sheath filament with a silicone-containing block copolymer core |
CN111469515A (zh) * | 2020-05-20 | 2020-07-31 | 京东方科技集团股份有限公司 | 显示装置、显示面板、显示盖板及其制造方法 |
KR20220011924A (ko) * | 2020-07-22 | 2022-02-03 | 주식회사 엘지화학 | 실리콘계 코팅 조성물 및 이를 포함하는 실리콘계 이형필름 |
CN111808539A (zh) * | 2020-09-09 | 2020-10-23 | 苏州桐力光电股份有限公司 | 一种热熔型oca光学胶膜及制备方法 |
EP4169994A1 (en) | 2021-10-25 | 2023-04-26 | Nitto Belgium NV | Pressure-sensitive adhesive composition and surface protection sheets comprising the same |
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US5214119A (en) * | 1986-06-20 | 1993-05-25 | Minnesota Mining And Manufacturing Company | Block copolymer, method of making the same, dimaine precursors of the same, method of making such diamines and end products comprising the block copolymer |
WO1996035458A2 (en) * | 1995-04-25 | 1996-11-14 | Minnesota Mining And Manufacturing Company | Tackified polydiorganosiloxane polyurea segmented copolymers and a process for making same |
CN1183113A (zh) * | 1995-04-25 | 1998-05-27 | 美国3M公司 | 增粘的聚二有机硅氧烷聚脲嵌段共聚物及其制备方法 |
US6730397B2 (en) * | 2001-12-18 | 2004-05-04 | 3M Innovative Properties Company | Silicone pressure sensitive adhesives, articles and methods |
US7371464B2 (en) * | 2005-12-23 | 2008-05-13 | 3M Innovative Properties Company | Adhesive compositions |
US7560166B2 (en) * | 2005-12-28 | 2009-07-14 | 3M Innovative Properties Company | Adhesive article, composite article, and methods of making the same |
KR20150119965A (ko) * | 2008-03-14 | 2015-10-26 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 연신 해제가능 접착 용품 |
EP2262868B1 (en) * | 2008-03-14 | 2018-02-28 | 3M Innovative Properties Company | Stretch releasable adhesive tape |
EP3052548B1 (en) * | 2013-09-30 | 2021-12-01 | 3M Innovative Properties Company | Silicone-polyether copolymers, adhesives and medical articles comprising same, and methods of making same |
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2016
- 2016-12-22 JP JP2018534628A patent/JP2019508522A/ja not_active Withdrawn
- 2016-12-22 CN CN201680077244.7A patent/CN108463533A/zh active Pending
- 2016-12-22 EP EP16882404.3A patent/EP3397715A4/en not_active Withdrawn
- 2016-12-22 US US16/066,786 patent/US20190016935A1/en not_active Abandoned
- 2016-12-22 WO PCT/US2016/068181 patent/WO2017116935A1/en active Application Filing
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JP7092247B1 (ja) | 2021-09-24 | 2022-06-28 | Agc株式会社 | 積層体、及び積層体の製造方法 |
JP2023046854A (ja) * | 2021-09-24 | 2023-04-05 | Agc株式会社 | 積層体、及び積層体の製造方法 |
US11840048B2 (en) | 2021-09-24 | 2023-12-12 | AGC Inc. | Laminated body and method for manufacturing laminated body |
TWI831378B (zh) * | 2021-09-24 | 2024-02-01 | 日商Agc股份有限公司 | 積層體及積層體之製造方法 |
Also Published As
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EP3397715A1 (en) | 2018-11-07 |
WO2017116935A1 (en) | 2017-07-06 |
US20190016935A1 (en) | 2019-01-17 |
EP3397715A4 (en) | 2019-08-14 |
CN108463533A (zh) | 2018-08-28 |
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