JP2021534287A - 2パートシアノアクリレート硬化性接着剤系 - Google Patents
2パートシアノアクリレート硬化性接着剤系 Download PDFInfo
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- JP2021534287A JP2021534287A JP2021507665A JP2021507665A JP2021534287A JP 2021534287 A JP2021534287 A JP 2021534287A JP 2021507665 A JP2021507665 A JP 2021507665A JP 2021507665 A JP2021507665 A JP 2021507665A JP 2021534287 A JP2021534287 A JP 2021534287A
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Abstract
Description
シアノアクリレート接着剤などの硬化性組成物は、一般に数分で、特定の基材に応じて、多くの場合数秒で、広範囲の基材を迅速に接着する優れた能力でよく認識されている。
(a)シアノアクリレート成分およびカチオン硬化触媒を含む第1パート、
(b)カチオン硬化性成分、開始剤成分および環状カーボネートを含む第2パートを含む2パート硬化性組成物であって、一緒に混合されると、カチオン性触媒はカチオン硬化性成分の硬化を開始する組成物を提供する。
式中、nは1〜3であり、
各Rは、水素、C1〜C12脂肪族またはC3〜C10環状脂肪族から独立して選択され、または一緒に少なくとも2つのRが、4〜12個の炭素原子を含む環系を形成し、前記環系は、任意に1つ以上の窒素、酸素または硫黄原子を含み、
各Rは、独立して非置換であるか、またはハロゲン、ヒドロキシル、アミノ基、スルホニル基、スルホンアミド基、チオール、C1〜C6アルキル、C1〜C6アルコキシ、C1〜C6エーテル、C1〜C6チオエーテル、C1〜C6エステル、C1〜C6ケトン、C1〜C6ケチミン、C1〜C6スルホン、C1〜C6スルホキシド、C1〜C6第一級アミド、C1〜C6第二級アミド、ハロC1〜C6アルキル、カルボキシル基、シアノ基、ニトロ基、ニトロソ基、−C(O)O−C1〜C6アルキル、−OC(O)O−C1〜C6アルキル、−OC(O)NR’R’、−N(R’)C(O)NR’R’、−N(R’)C(O)O−C1〜C6アルキル、オキソ、C3〜C6シクロアルキル、C3〜C6ヘテロシクリル、C2〜C5ヘテロアリールおよびC6〜C10アリールの少なくとも一つで置換されていてもよく、各R’は、水素およびC1〜C6アルキルからなる群から独立して選択される。
式中、nは、1または2であり、各Rは、Hまたは1以上のヒドロキシル、C1〜C6アルキルまたはC1〜C6アルコキシで任意に置換されたC1〜C12脂肪族から独立して選択される。
本発明は、以下の実施例を検討することにより、より容易に理解されるであろう。
シアノアクリレート成分には、H2C=C(CN)−COOR(式中、Rは、C1〜15アルキル、C2〜15アルコキシアルキル、C3〜15シクロアルキル、C2〜15アルケニル、C7〜15アラルキル、C6〜15アリール、C3〜15アリルおよびC3〜15ハロアルキル基から選択される)で表されるものなどのシアノアクリレートモノマーが含まれる。望ましくは、シアノアクリレートモノマーは、メチルシアノアクリレート、エチル−2−シアノアクリレート、プロピルシアノアクリレート、ブチルシアノアクリレート(n−ブチル−2−シアノアクリレートなど)、オクチルシアノアクリレート、アリルシアノアクリレート、β−メトキシエチルシアノアクリレート、およびそれらの組み合わせから選択される。特に望ましいものは、エチル−2−シアノアクリレート(「ECA」)である。
式中、
R3およびR4はそれ自体がシアノアクリレートモノマーの重合を引き起こさない有機基であり、R5はHまたはCH3であり、nは1〜4の整数である。適切なR3およびR4基の例は、R基、メトキシなどのアルコキシ基、およびフェノキシなどのアリールオキシ基である。R3およびR4基は、ハロゲンまたは他の置換基を含んでいてもよく、その例はトリフルオロプロピルである。しかしながら、R4およびR5基として適していない基は、アミノ、置換アミノおよびアルキルアミノなどの塩基性基である。
nは3より大きく、例えば3〜12の範囲内であり、nは9であることが特に望ましい。
式中、Cmは、直鎖または分枝アルキルまたはアルケニル鎖であることができ、mは1〜30の整数であり、例えば5〜20であり、nは2〜30の整数であり、例えば5〜15であり、RはHまたはアルキル、例えばC1−6アルキルであってもよい。
式中、Rは水素、C1〜6アルキル、C1〜6アルキルオキシ、アルキルチオエーテル、ハロアルキル、カルボン酸およびそれらのエステル、スルフィン酸、スルホン酸および亜硫酸およびエステル、ホスフィン酸、ホスホン酸および亜リン酸およびそれらのエステルであり、Zは、ポリエーテル結合、nは、1〜12、pは、1〜3であり、上記で定義したとおりであり、R’は、Rと同じであり、gはnと同じである。
パートB
環状カーボネートという用語は、環状リング構造の一部としてカーボネート官能基を含む環部材を意味すると理解すべきである。
式中、nは1〜3であり、
各Rは、水素、C1〜C12脂肪族またはC3〜C10環状脂肪族から独立して選択され、または一緒に少なくとも2つのRが4〜12個の炭素原子を含む環系を形成し、前記環系は、任意に1つ以上の窒素、酸素または硫黄原子を含み、
各Rは、独立して非置換であるか、またはハロゲン、ヒドロキシル、アミノ基、スルホニル基、スルホンアミド基、チオール、C1〜C6アルキル、C1〜C6アルコキシ、C1〜C6エーテル、C1〜C6チオエーテル、C1〜C6エステル、C1〜C6ケトン、C1〜C6ケチミン、C1〜C6スルホン、C1〜C6スルホキシド、C1〜C6第一級アミド、C1〜C6第二級アミド、ハロC1〜C6アルキル、カルボキシル基、シアノ基、ニトロ基、ニトロソ基、−C(O)O−C1〜C6アルキル、−OC(O)O−C1〜C6アルキル、−OC(O)NR’R’、−N(R’)C(O)NR’R’、−N(R’)C(O)O−C1〜C6アルキル、オキソ、C3〜C6シクロアルキル、C3〜C6ヘテロシクリル、C2〜C5ヘテロアリールおよびC6〜C10アリールの少なくとも一つで置換されていてもよく、各R’は、水素およびC1〜C6アルキルからなる群から独立して選択される。
Claims (33)
- a.シアノアクリレート成分およびカチオン硬化触媒を含む第1パート、
b.カチオン硬化性成分、開始剤成分および環状カーボネートを含む第2パートを含む2パート硬化性組成物であって、一緒に混合されると、カチオン性触媒はカチオン硬化性成分の硬化を開始する組成物。 - 環状カーボネートが以下の構造
(式中、nは1〜3であり、
各Rは、水素、C1〜C12脂肪族またはC3〜C10環状脂肪族から独立して選択され、または一緒に少なくとも2つのRが4〜12個の炭素原子を含む環系を形成し、前記環系は、任意に1つ以上の窒素、酸素または硫黄原子を含み、
各Rは、独立して非置換であるか、またはハロゲン、ヒドロキシル、アミノ基、スルホニル基、スルホンアミド基、チオール、C1〜C6アルキル、C1〜C6アルコキシ、C1〜C6エーテル、C1〜C6チオエーテル、C1〜C6エステル、C1〜C6ケトン、C1〜C6ケチミン、C1〜C6スルホン、C1〜C6スルホキシド、C1〜C6第一級アミド、C1〜C6第二級アミド、ハロC1〜C6アルキル、カルボキシル基、シアノ基、ニトロ基、ニトロソ基、−C(O)O−C1〜C6アルキル、−OC(O)O−C1〜C6アルキル、−OC(O)NR’R’、−N(R’)C(O)NR’R’、−N(R’)C(O)O−C1〜C6アルキル、オキソ、C3〜C6シクロアルキル、C3〜C6ヘテロシクリル、C2〜C5ヘテロアリールおよびC6〜C10アリールの少なくとも一つで置換されていてもよく、各R’は、水素およびC1〜C6アルキルからなる群から独立して選択される。)を有する、請求項1に記載の組成物。 - nが1または2であり、好ましくはnが1である、請求項1または2に記載の組成物。
- Rが、1以上のヒドロキシル、C1〜C6アルキルまたはC1〜C6アルコキシで任意に置換されたC1〜C12脂肪族である、請求項2または3に記載の組成物。
- Rが、1以上のヒドロキシル、C1〜C6アルキルまたはC1〜C6アルコキシで任意に置換されたC1〜C12アルキルである、請求項6に記載の組成物。
- 環状カーボネートが、第2パートの総重量に基づいて、約5重量%〜約35重量%の量で、任意に第2パートの総重量に基づいて、約8重量%〜30重量%、例えば、約10重量%〜約25重量%、例えば、10重量%〜18重量%の量で存在する、請求項1〜7のいずれか一項に記載の組成物。
- 環状カーボネートが、室温で液体である、請求項1〜8のいずれか一項に記載の組成物。
- コアシェルゴム粒子をさらに含む、請求項1〜9のいずれか一項に記載の組成物。
- コアシェルゴム粒子が、アクリロニトリルブタジエン−スチレンコポリマーおよび/またはメタクリル酸メチルブタジエンスチレンコポリマーを含む、請求項10に記載の組成物。
- コアシェルゴム粒子が、組成物の第2パートの総重量に基づいて、組成物の第2パートに約10重量%〜15重量%の量で存在する、請求項10または11に記載の組成物。
- 組成物を形成するために使用されるコアシェルゴム粒子が、約50μm〜約300μm、例えば、約100μm〜約250μm、例えば、150μm〜約200μm、例えば、約175μm〜190μmの平均粒子サイズを有する、請求項10〜12のいずれか一項に記載の組成物。
- 熱可塑性樹脂をさらに含む、請求項1〜13のいずれか一項に記載の組成物。
- 熱可塑性樹脂が、熱可塑性アクリル樹脂を含む、請求項14に記載の組成物。
- 熱可塑性樹脂が、メタクリル酸メチルおよびメタクリル酸ブチルコポリマーから構成される、請求項14または15に記載の組成物。
- 熱可塑性樹脂が、組成物の総重量に基づいて、約1.5重量%〜約15重量%の量で、例えば、組成物の総重量に基づいて、約2重量%〜約10重量%の量で存在する、請求項14〜16のいずれか一項に記載の組成物。
- 熱可塑性樹脂が、第2パートの総重量に基づいて、約5重量%〜約15重量%の量で、例えば、第2パートの総重量に基づいて、約7重量%〜約14重量%の量で存在する、請求項14〜17のいずれか一項に記載の組成物。
- シアノアクリレート成分が、H2C=C(CN)−COOR(式中、Rは、アルキル、アルコキシアルキル、シクロアルキル、アルケニル、アラルキル、アリール、アリルおよびハロアルキル基から選択される)を含む、請求項1〜18のいずれか一項に記載の組成物。
- カチオン性触媒が、リチウムおよび周期表の第II族からの金属の塩、ならびに非求核性酸を含む、請求項1〜19のいずれか一項に記載の組成物。
- カチオン性触媒が、水中の10重量%溶液として測定したとき、1.0未満のpHを有する非求核性酸である、請求項1〜20のいずれか1項に記載の組成物。
- カチオン性触媒が、フルオロホウ酸、フルオロヒ酸、フルオロアンチモン酸およびフルオロリン酸、テトラフルオロホウ酸リチウム、ジテトラフルオロホウ酸カルシウム、ジテトラフルオロホウ酸マグネシウム、ヘキサフルオロリン酸リチウム、ジヘキサフルオロリン酸カルシウム、ジヘキサフルオロリン酸マグネシウム、ヘキサフルオロアンチモン酸リチウムおよびヘキサフルオロヒ酸リチウム、ランタニドトリフレート塩、アリールヨードニウム塩、アリールスルホニウム塩、ランタントリフレート、イテルビウムトリフレート、トリメトキシボロキシン、トリメトキシボロキシン−アルミニウムアセチルアセトナート、アミン−ホウ素トリハライド錯体、第四アンモニウム塩、第四ホスホニウム塩、トリアリールスルホニウム塩、ジアリールヨードニウム塩、およびジアゾニウム塩、トリアルコキシボロキシン硬化剤およびそれらの組み合わせからなる群から選択されるメンバーである、請求項1〜21のいずれか一項に記載の組成物。
- カチオン硬化性成分が、エポキシ成分、エピスルフィド成分、オキセタン成分、ビニルエーテル成分およびそれらの組み合わせから選択される、請求項1〜22のいずれか一項に記載の組成物。
- カチオン硬化性成分が、脂環式エポキシ、芳香族エポキシ、脂肪族エポキシおよび水素化芳香族エポキシからなる群から選択されるエポキシ成分である、請求項1〜23のいずれか一項に記載の組成物。
- エポキシ成分が、2−(3,4−エポキシ)シクロヘキシル−5,5−スピロ−(3,4−エポキシ)シクロヘキサン−m−ジオキサン、3,4−エポキシシクロヘキシルメチル−3,4−エポキシシクロヘキサンカルボキシレート、3,4−エポキシ−6−メチルシクロヘキシルメチル−3,4−エポキシ−6−メチルシクロヘキサンカルボキシレート、ビニルシクロヘキサンジオキシド、ビス(3,4−エポキシシクロヘキシルメチル)アジペート、ビス(3,4−エポキシ−6−メチルシクロヘキシルメチル)アジペート、エキソ−エキソビス(2,3−エポキシシクロペンチル)エーテル、エンド−エキソビス(2,3−エポキシシクロペンチル)エーテル、2,2−ビス(4−(2,3−エポキシプロポキシ)シクロヘキシル)プロパン、2,6−ビス(2,3−エポキシプロポキシシクロヘキシル−p−ジオキサン)、2,6−ビス(2,3−エポキシプロポキシ)ノルボルネンからなる群から選択される脂環式エポキシを含む、請求項23または24に記載の組成物。
- エポキシ成分が、エポキシ官能化水素化ビスフェノールA、ビスフェノールF、ビスフェノールE、ビスフェノールS、およびビフェニルからなる群から選択されるメンバーを含む、請求項23に記載の組成物。
- 第1パートが、デュアルチャンバーシリンジの第1のチャンバーに収容され、第2パートが、デュアルチャンバーシリンジの第2のチャンバーに収容される、請求項1〜26のいずれか一項に記載の組成物。
- 第1パートが、リン酸をさらに含む、請求項1〜27のいずれか一項に記載の組成物。
- 第2パートが、可塑剤、充填剤および強化剤のうちの少なくとも1つをさらに含む、請求項1〜28のいずれか一項に記載の組成物。
- 強化剤が、(1)(a)エチレン、アクリル酸メチルおよびカルボン酸硬化部位を有するモノマーの組み合わせの反応生成物、(2)(b)エチレンとアクリル酸メチルのジポリマー、(3)(a)と(b)の組み合わせ、(4)塩化ビニリデン−アクリロニトリル共重合体、(5)塩化ビニル/酢酸ビニル共重合体、(6)ポリエチレンとポリ酢酸ビニルの共重合体、およびその組み合わせからなる群から選択されるメンバーである、請求項29に記載の組成物。
- 第1パートおよび第2パートが、体積で約1:2の比率で存在する、請求項1〜30のいずれか一項に記載の組成物。
- 第1パートおよび第2パートがそれぞれ、デュアルチャンバー容器の別個のチャンバーに収容されている、請求項1〜31のいずれか一項に記載の組成物。
- 開始剤成分が、N、N’−ジメチル−p−トルイジンを含む、請求項1〜32のいずれか一項に記載の組成物。
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-
2018
- 2018-10-17 GB GB1816925.0A patent/GB2576792B/en active Active
-
2019
- 2019-08-12 CN CN201980064340.1A patent/CN112789302B/zh active Active
- 2019-08-12 WO PCT/EP2019/071572 patent/WO2020035442A1/en unknown
- 2019-08-12 KR KR1020217004349A patent/KR20210044784A/ko not_active Application Discontinuation
- 2019-08-12 EP EP19755320.9A patent/EP3837293A1/en active Pending
- 2019-08-12 JP JP2021507665A patent/JP2021534287A/ja active Pending
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2021
- 2021-01-26 US US17/158,989 patent/US20210171686A1/en active Pending
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CN112789302A (zh) | 2021-05-11 |
EP3837293A1 (en) | 2021-06-23 |
WO2020035442A1 (en) | 2020-02-20 |
GB201816925D0 (en) | 2018-11-28 |
GB2576792B (en) | 2022-09-14 |
KR20210044784A (ko) | 2021-04-23 |
US20210171686A1 (en) | 2021-06-10 |
CN112789302B (zh) | 2023-05-16 |
GB2576792A (en) | 2020-03-04 |
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