JPH023481A - Acrylic pressure-sensitive adhesive composition - Google Patents
Acrylic pressure-sensitive adhesive compositionInfo
- Publication number
- JPH023481A JPH023481A JP15259188A JP15259188A JPH023481A JP H023481 A JPH023481 A JP H023481A JP 15259188 A JP15259188 A JP 15259188A JP 15259188 A JP15259188 A JP 15259188A JP H023481 A JPH023481 A JP H023481A
- Authority
- JP
- Japan
- Prior art keywords
- meth
- acrylic
- adhesive composition
- acrylate
- adhesive
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 19
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 title abstract description 15
- 239000004820 Pressure-sensitive adhesive Substances 0.000 title description 11
- -1 acrylic ester Chemical class 0.000 claims abstract description 18
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 16
- 239000003522 acrylic cement Substances 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 9
- 150000003512 tertiary amines Chemical class 0.000 claims description 9
- 238000007334 copolymerization reaction Methods 0.000 claims description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
- 230000001070 adhesive effect Effects 0.000 abstract description 19
- 239000000853 adhesive Substances 0.000 abstract description 18
- 230000007062 hydrolysis Effects 0.000 abstract description 13
- 238000006460 hydrolysis reaction Methods 0.000 abstract description 13
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 abstract description 12
- 238000000034 method Methods 0.000 abstract description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 abstract description 3
- 150000003254 radicals Chemical class 0.000 abstract description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract description 2
- 239000003999 initiator Substances 0.000 abstract description 2
- 150000002978 peroxides Chemical class 0.000 abstract description 2
- 150000001412 amines Chemical class 0.000 abstract 2
- 125000002348 vinylic group Chemical group 0.000 abstract 2
- MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 230000002265 prevention Effects 0.000 abstract 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 11
- 230000007423 decrease Effects 0.000 description 9
- 238000012360 testing method Methods 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 229920006267 polyester film Polymers 0.000 description 6
- 229920002284 Cellulose triacetate Polymers 0.000 description 4
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 4
- 229920006243 acrylic copolymer Polymers 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- DPBJAVGHACCNRL-UHFFFAOYSA-N 2-(dimethylamino)ethyl prop-2-enoate Chemical compound CN(C)CCOC(=O)C=C DPBJAVGHACCNRL-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 125000005396 acrylic acid ester group Chemical group 0.000 description 1
- 239000012790 adhesive layer Substances 0.000 description 1
- CHIHQLCVLOXUJW-UHFFFAOYSA-N benzoic anhydride Chemical compound C=1C=CC=CC=1C(=O)OC(=O)C1=CC=CC=C1 CHIHQLCVLOXUJW-UHFFFAOYSA-N 0.000 description 1
- AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 238000012662 bulk polymerization Methods 0.000 description 1
- 239000012986 chain transfer agent Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は、粘着力、凝集力並びに耐熱性に優れ、被着体
や支持体の加水分解を阻止しうるアクリル系粘着剤組成
物に関する。DETAILED DESCRIPTION OF THE INVENTION (Field of Industrial Application) The present invention relates to an acrylic pressure-sensitive adhesive composition that has excellent adhesive strength, cohesive strength, and heat resistance, and is capable of inhibiting hydrolysis of adherends and supports.
（従来の技術）
アクリル系粘着剤の一般的な組成は、１５重量％以下の
（メタ）アクリル酸と、８５重量％以上の（メタ）アク
リル酸エステル及び重合性のビニルモノマーとから成っ
ている。(Prior Art) The general composition of acrylic adhesives is 15% by weight or less of (meth)acrylic acid, and 85% by weight or more of (meth)acrylic ester and polymerizable vinyl monomer. .
ここで添加される（メタ）アクリル酸は、粘着剤の粘着
力と凝集力とを向上させるとともに、カルボキシル基が
架橋点となり、粘着剤内部に架橋構造が形成される。The (meth)acrylic acid added here improves the adhesive strength and cohesive force of the adhesive, and the carboxyl groups serve as crosslinking points to form a crosslinked structure inside the adhesive.
（メタ）アクリル酸の添加量が増加すると、アクリル系
粘着剤のガラス転移温度（Ｔｇ）が上昇し、内部凝集力
が向上するが、逆に初期接着性（タック）は低下する。When the amount of (meth)acrylic acid added increases, the glass transition temperature (Tg) of the acrylic adhesive increases and the internal cohesive force improves, but on the contrary, the initial adhesiveness (tack) decreases.
一方、該粘着剤中に含有された（メタ）アクリル酸等の
カルボキシル基が、加水分解され易い被着体や支持体と
長期間接触した状態で置かれ、且つ水分が共存する場合
には、該カルボキシル基はアクリル系粘着剤の被着体や
支持体が加水分解するのを促進することが知られている
。On the other hand, if the carboxyl group such as (meth)acrylic acid contained in the adhesive is left in contact with an easily hydrolyzed adherend or support for a long period of time, and moisture is present, It is known that the carboxyl group promotes hydrolysis of the adherend or support of the acrylic pressure-sensitive adhesive.
そこで、被着体や支持体に加水分解を起こす恐れのない
アクリル系粘着剤組成物として、特開昭５９−１１１１
１４号公報には（メタ）アクリル酸を含まないアクリル
系粘着剤組成物、即ち、アクリル酸ブチルとメタクリル
酸ベンジルとメタクリル酸２−ヒドロキシエチルとを共
重合したアクリル系粘着剤組成物が開示されている。Therefore, as an acrylic pressure-sensitive adhesive composition that does not cause hydrolysis on adherends or supports, JP-A-59-1111
Publication No. 14 discloses an acrylic adhesive composition that does not contain (meth)acrylic acid, that is, an acrylic adhesive composition that is a copolymerization of butyl acrylate, benzyl methacrylate, and 2-hydroxyethyl methacrylate. ing.
しかしながら、上述の（メタ）アクリル酸を含まないア
クリル系粘着剤組成物は、加水分解され易い被着体、例
えば、三酢酸セルロースフィルムに対し、加水分解を抑
制する性能は優れているものの、粘着剤として要求され
る各種性能、特に内部凝集力と粘着力との両性能を同時
に満足させることが難しいという問題点があった。However, although the above-mentioned acrylic adhesive compositions that do not contain (meth)acrylic acid have excellent performance in suppressing hydrolysis on adherends that are easily hydrolyzed, such as cellulose triacetate film, There has been a problem in that it is difficult to simultaneously satisfy various performances required as an agent, especially internal cohesive strength and adhesive strength.
特に、該粘着剤が被着状態で高温下に置かれた場合は、
粘着剤層にずれ、発泡、剥離が起こり易く、高信鎖性が
要求される光学用途で使用することが難かしいという問
題点もあった。In particular, if the adhesive is placed under high temperature while adhered,
There was also the problem that the adhesive layer was prone to slipping, foaming, and peeling, making it difficult to use it in optical applications that required high chain reliability.
又、ＯＨ基を架橋点とし、イソシアネートと架橋反応さ
せた場合は、イソシアネートの適正添加量が極めて狭い
範囲に限られるので、粘着剤の性能を制御するのが難し
いという問題点もあった。In addition, when the OH group is used as a crosslinking point and a crosslinking reaction is performed with an isocyanate, the appropriate amount of isocyanate added is limited to an extremely narrow range, so there is a problem that it is difficult to control the performance of the adhesive.
（発明が解決しようとする課題）
本発明は、アクリル酸エステル及び該アクリル酸エステ
ルと共重合可能なカルボキシル基含有化合物からなるア
クリル系粘着剤に、第三級アミンをラジカル共重合させ
ることにより、該アクリル系粘着剤中に存在するカルボ
キシル基によって被着体や支持体に加水分解が起こるの
を阻止し、粘着力、凝集力及び耐久性に優れたアクリル
系粘着剤組成物を提供することを主旨とする。(Problems to be Solved by the Invention) The present invention provides a solution by radically copolymerizing a tertiary amine with an acrylic pressure-sensitive adhesive consisting of an acrylic ester and a carboxyl group-containing compound copolymerizable with the acrylic ester. It is an object of the present invention to provide an acrylic adhesive composition that prevents hydrolysis of adherends and supports due to the carboxyl groups present in the acrylic adhesive and has excellent adhesive strength, cohesive force, and durability. The main idea.
（課題を解決するための手段）
本発明のアクリル系粘着剤組成物は、上記問題点を解決
するためになされたものであり、（メタ）アクリル酸エ
ステル６５〜９６重量％、該（メタ）アクリル酸エステ
ルと共重合可能なカルボキシル基含有化合物３〜１５重
量％及びビニル基を有する第三級アミン１〜２０重量％
をラジカル共重合することにより、上記目的が達成され
る。(Means for Solving the Problems) The acrylic pressure-sensitive adhesive composition of the present invention was made to solve the above problems, and contains 65 to 96% by weight of (meth)acrylic ester, the (meth) 3 to 15% by weight of a carboxyl group-containing compound copolymerizable with an acrylic acid ester and 1 to 20% by weight of a tertiary amine having a vinyl group.
The above object can be achieved by radical copolymerization.
本発明で使用される（メタ）アクリル酸エステルとは、
アクリル酸エステル又はメタクリル酸エステルであって
、例えば、（メタ）アクリル酸ブチル、（メタ）アクリ
ル酸２−エチルヘキシル、（メタ）アクリル酸イソオク
チル、（メタ）アクリル酸イソノニル、（メタ）アクリ
ル酸オクチル、（メタ）アクリル酸デシル、（メタ）ア
クリル酸ベンジル、 （メタ）アクリル酸２−ヒドロキ
シエチル等が好適に使用される。The (meth)acrylic acid ester used in the present invention is
Acrylic esters or methacrylic esters, such as butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, isooctyl (meth)acrylate, isononyl (meth)acrylate, octyl (meth)acrylate, Decyl (meth)acrylate, benzyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, etc. are preferably used.
本発明で使用される（メタ）アクリル酸エステルと共重
合可能なカルボキシル基含有化合物としては、例えば、
アクリル酸、メタクリル酸、イタコン酸、クロトン酸、
マレイン酸等が挙げられる。Examples of the carboxyl group-containing compound copolymerizable with the (meth)acrylic ester used in the present invention include:
Acrylic acid, methacrylic acid, itaconic acid, crotonic acid,
Examples include maleic acid.
本発明で使用されるビニル基を有する第三級アミンとし
ては、例えば、（メタ）アクリル酸ジメチルアミノエチ
ル、（メタ）アクリル酸ジメチルアミノエチル、ジメチ
ルアミノプロピル（メタ）アクリルアミド等が好適に使
用される。As the tertiary amine having a vinyl group used in the present invention, for example, dimethylaminoethyl (meth)acrylate, dimethylaminoethyl (meth)acrylate, dimethylaminopropyl (meth)acrylamide, etc. are preferably used. Ru.
本発明のアクリル系粘着剤組成物は、上記（メタ）アク
リル酸エステル、カルボキシル基含有化合物及び第三級
アミンをラジカル共重合したものであって、カルボキシ
基含有化合物の比率は小さくなると粘着剤の凝集力が低
下し、逆に多くなると粘着力が低下すると共に、被着体
や支持体の加水分解を促進するようになるので、３〜１
５重量％に限定されるのであり、第三級アミンの比率は
小さくなるとカルボキシ基含有化合物による加水分解を
抑止する効果が低下し、逆に多くなると粘着剤が軟らか
くなり、粘着力や凝集力が低下するので１〜２０重量％
に限定され、残りの６５〜９６重量％が（メタ）アクリ
ル酸エステルである。The acrylic pressure-sensitive adhesive composition of the present invention is obtained by radical copolymerization of the above-mentioned (meth)acrylic acid ester, a carboxyl group-containing compound, and a tertiary amine, and as the ratio of the carboxyl group-containing compound decreases, the pressure-sensitive adhesive composition decreases. If the cohesive force decreases, and conversely if it increases, the adhesive force will decrease and the hydrolysis of the adherend or support will be promoted, so 3 to 1
The amount of tertiary amine is limited to 5% by weight, and as the ratio of tertiary amine decreases, the effect of inhibiting hydrolysis by carboxy group-containing compounds decreases, and on the other hand, as it increases, the adhesive becomes soft and the adhesive strength and cohesive force decrease. 1 to 20% by weight as it decreases
The remaining 65 to 96% by weight is (meth)acrylic acid ester.
本発明の粘着剤組成物の凝集力を向上させるために、更
に（メタ）アクリル酸エステルと共重合可能なビニルエ
ステル、例えば、酢酸ビニル、塩化ビニル、塩化ビニリ
デン、アクリロニトリル、スチレン等を共重合させても
よい。In order to improve the cohesive force of the adhesive composition of the present invention, a vinyl ester copolymerizable with the (meth)acrylic acid ester, such as vinyl acetate, vinyl chloride, vinylidene chloride, acrylonitrile, styrene, etc., is further copolymerized. You can.
本発明のアクリル粘着剤組成物のラジカル共重合方法は
、任意の方法が採用されてよく、例えば、溶液重合、塊
状重合、エマルジョン重合等が挙げられる。Any method may be employed as the radical copolymerization method for the acrylic pressure-sensitive adhesive composition of the present invention, and examples thereof include solution polymerization, bulk polymerization, emulsion polymerization, and the like.
重合開始剤としては、過酸化物系、アゾ系化合物等従来
公知の任意のものが使用しうるが、光又は放射線等を照
射して重合してもよい。As the polymerization initiator, any conventionally known initiators such as peroxides and azo compounds can be used, and polymerization may be carried out by irradiation with light or radiation.
又、分子量を調節するために、適当な連鎖移動剤、例え
ば、ラウリルメルカプタン等を使用してもよい。Further, in order to adjust the molecular weight, a suitable chain transfer agent such as lauryl mercaptan may be used.
更に、幅広い粘着物性を得るために、必要に応じて、可
塑剤、粘着付与剤、劣化防止剤等が添加されでもよい。Furthermore, in order to obtain a wide range of adhesive properties, plasticizers, tackifiers, deterioration inhibitors, etc. may be added as necessary.
（作用）
本発明のアクリル系粘着剤組成物は、（メタ）アクリル
酸エステル、該（メタ）アクリル酸エステルと共重合可
能なカルボキシル基含有化合物、及び第三級アミンがラ
ジカル共重合されているので、該カルボキシル基含有化
合物のカルボキシル基による加水分解が抑制される。(Function) The acrylic pressure-sensitive adhesive composition of the present invention comprises a (meth)acrylic ester, a carboxyl group-containing compound copolymerizable with the (meth)acrylic ester, and a tertiary amine, which are radically copolymerized. Therefore, hydrolysis of the carboxyl group-containing compound by the carboxyl group is suppressed.
又、本発明による粘着剤が、例えば、三酢酸セルロース
のような被着体や支持体と接触し、これを加水分解して
も、その際遊離した酢酸を第三級アミンが補足し、該酢
酸により加水分解が促進されるのを防［ヒする。Furthermore, even if the adhesive according to the present invention comes into contact with an adherend or support such as cellulose triacetate and hydrolyzes it, the tertiary amine captures the acetic acid liberated at that time, and Prevents hydrolysis from being accelerated by acetic acid.
（実施例） 以下に本発明の実施例について述べる。(Example) Examples of the present invention will be described below.
実施例１〜６、比較例
１）アクリル共重合体の調製
還流器及び攪拌器が設置されたフラスコ中に、表２に示
した所定量のアクリル酸ブチル、アクリル酸、ジメチル
アミノエチルアクリレート、過酸化ベンゾイル及び酢酸
エチルを添加して均一に混合した後、窒素気流中で攪拌
しながら還流温度で６時間ラジカル共重合しアクリル共
重合体溶液を調製した。Examples 1 to 6, Comparative Example 1) Preparation of acrylic copolymer In a flask equipped with a reflux device and a stirrer, predetermined amounts of butyl acrylate, acrylic acid, dimethylaminoethyl acrylate, and filtrate shown in Table 2 were added. After adding and uniformly mixing benzoyl oxide and ethyl acetate, radical copolymerization was carried out at reflux temperature for 6 hours while stirring in a nitrogen stream to prepare an acrylic copolymer solution.
（２）アクリル系粘着剤組成物の調製
上記アクリル共重合体溶液を固形分が２５重量％となる
ように酢酸エチルで希釈した後、該共重合体の固形分１
００重量部に、トリイソシアネート２重量部を添加、攪
拌しアクリル系粘着剤組成物を調製した。(2) Preparation of acrylic adhesive composition The above acrylic copolymer solution was diluted with ethyl acetate so that the solid content was 25% by weight, and then the solid content of the copolymer was 1
2 parts by weight of triisocyanate was added to 00 parts by weight and stirred to prepare an acrylic pressure-sensitive adhesive composition.
（３）アクリル粘着剤ラミネートの作成（２）で調製し
たアクリル系粘着剤組成物を、シリコン処理した３８μ
ｍ厚のポリエステルフィルム上に、乾燥後の厚さが２５
μｍになるようにアプリケーターで塗工し、オーブン中
で５分間乾燥させた後、５０℃１ｍ厚の三酢酸セルロー
スフィルムをラミネーターで貼り合わせ、アクリル粘着
剤ラミネート（ａｌを作成した。(3) Creation of acrylic adhesive laminate The acrylic adhesive composition prepared in (2) was applied to a 38μ silicon-treated laminate.
m thick polyester film with a dry thickness of 25 mm.
After coating with an applicator to a thickness of μm and drying in an oven for 5 minutes, a 1 m thick cellulose triacetate film was laminated at 50° C. with a laminator to create an acrylic adhesive laminate (al).
又、前記三酢酸セルロースフィルムの代わりに５０μｍ
厚のポリエステルフィルムをラミネーターで貼り合わせ
、アクリル粘着剤ラミネート（ｂ）を作成した。Also, instead of the cellulose triacetate film, 50 μm
Thick polyester films were laminated together using a laminator to create an acrylic adhesive laminate (b).
（４）物性の測定
ｉ）加水分解による外観試験
（３）で調製したアクリル粘着剤ラミネート（ａ）を−
週間放置後、５０ ｘ １００龍の大きさに切断し、シ
リコン処理したポリエステルフィルムを剥離した後、剥
離面に７５Ｘ１５０ ｍのガラス板を気泡の入らぬよう
にラミネーターで貼合わせ試験片とした。(4) Measurement of physical properties i) Appearance test by hydrolysis The acrylic adhesive laminate (a) prepared in (3) was
After leaving it for a week, it was cut to a size of 50 x 100 mm, the silicone-treated polyester film was peeled off, and a 75 x 150 m glass plate was attached to the peeled surface using a laminator to make a test piece.
該試験片をガラススタンドに立て、８０℃、ＲＨ９０％
の恒温恒湿槽中に、それぞれ、５００．７５０．１００
０．１２５０及び１５００時間放置した後、加水分解に
よる外観の変化を肉眼で観察し、表１に示した外観の変
化に対応する評価点を表３に示した。The test piece was placed on a glass stand at 80°C and RH90%.
500.750.100 respectively in a constant temperature and humidity chamber.
After standing for 0.1250 and 1500 hours, changes in appearance due to hydrolysis were observed with the naked eye, and evaluation scores corresponding to changes in appearance shown in Table 1 are shown in Table 3.
（以下余白）
表 １
ｉｉ ） ９０℃剪断剪断力試験
（３）で調製したアクリル粘着剤ラミネート（ｂ）を１
５ ｘ １００鶴の大きさに切断し、シリコン処理した
ポリエステルフィルムを剥離した後、剥離面にガラス板
が１５℃１５ｍｍの面積で接着するように、重さ２ ｋ
ｇのローラーを一往復させて圧着した後、粘着剤が露出
した部分にポリエステルフィルムを貼り合わせ試験片と
した。(Margin below) Table 1 ii) The acrylic adhesive laminate (b) prepared in the 90°C shear force test (3) was
After cutting the polyester film into 5 x 100 cranes and peeling off the silicone-treated polyester film, a glass plate weighing 2 kg was attached to the peeled surface at 15°C in an area of 15 mm.
After the roller g was moved back and forth once for pressure bonding, a polyester film was attached to the exposed portion of the adhesive to form a test piece.
該試験片を９０℃の恒温槽に２時間放置した後、試験片
を恒温槽付インストロン型引張試験機で９０℃に保ちな
がら、１１１／分の速度で１８０度方向に引張り、剪断
接着力を測定し、その結果を表３に示した。After leaving the test piece in a constant temperature bath at 90°C for 2 hours, the test piece was pulled in a 180 degree direction at a rate of 111/min while keeping the test piece at 90°C in an Instron type tensile tester with a constant temperature bath to measure the shear adhesive strength. was measured, and the results are shown in Table 3.
表２
表
注）９０℃剪断剪断力の単位： ｋｇｆ／１５Ｘ１５龍
クリル酸エステシクリル酸エステルリル酸エステルと共
重合可能なカルボキシル基含有化合物及び第三級アミン
がラジカル共重合されているので、粘着力、凝集力、耐
熱性等の性能が優れ、被着体や支持体が加水分解するこ
とがない。Table 2 Note: Unit of 90°C shearing force: kgf/15 It has excellent properties such as cohesive force and heat resistance, and does not cause hydrolysis of adherends or supports.
Claims (1)
（メタ）アクリル酸エステルと共重合可能なカルボキシ
ル基含有化合物３〜１５重量％及びビニル基を有する第
三級アミン１〜２０重量％をラジカル共重合してなるア
クリル系粘着剤組成物。1. 65-96% by weight of (meth)acrylic ester, 3-15% by weight of a carboxyl group-containing compound copolymerizable with the (meth)acrylic ester, and 1-20% by weight of a tertiary amine having a vinyl group. An acrylic adhesive composition formed by radical copolymerization.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63152591A JPH0798926B2 (en) | 1988-06-21 | 1988-06-21 | Acrylic adhesive composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63152591A JPH0798926B2 (en) | 1988-06-21 | 1988-06-21 | Acrylic adhesive composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH023481A true JPH023481A (en) | 1990-01-09 |
| JPH0798926B2 JPH0798926B2 (en) | 1995-10-25 |
Family
ID=15543788
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63152591A Expired - Fee Related JPH0798926B2 (en) | 1988-06-21 | 1988-06-21 | Acrylic adhesive composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0798926B2 (en) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009120805A (en) * | 2007-10-22 | 2009-06-04 | Nitto Denko Corp | Pressure-sensitive adhesive composition for optical film, pressure-sensitive adhesive layer for optical film, production method thereof, pressure-sensitive adhesive optical film and image display |
| EP2072552A3 (en) * | 2007-12-20 | 2009-07-29 | Nitto Denko Corporation | Pressure-sensitive adhesive composition for optical films, pressure-sensitive adhesive optical film and image display |
| WO2014051106A1 (en) | 2012-09-28 | 2014-04-03 | リンテック株式会社 | Adhesive sheet and method for manufacturing adhesive sheet |
| US8709597B2 (en) | 2008-02-15 | 2014-04-29 | Nitto Denko Corporation | Pressure-sensitive adhesive composition for optical films, pressure-sensitive adhesive optical film and image display |
| US8784987B2 (en) | 2008-03-14 | 2014-07-22 | Nitto Denko Corporation | Pressure-sensitive adhesive composition for optical films, pressure-sensitive adhesive optical film and image display |
| US8962135B2 (en) | 2007-10-22 | 2015-02-24 | Nitto Denko Corporation | Pressure-sensitive adhesive composition for optical film, pressure-sensitive adhesive layer for optical film, production method thereof, pressure-sensitive adhesive optical film and image display |
| US9133368B2 (en) | 2011-08-31 | 2015-09-15 | Lintec Corporation | Adhesive sheet |
| US10363718B2 (en) | 2014-04-02 | 2019-07-30 | Lintec Corporation | Adhesive sheet and adhesive sheet production method |
| US10465101B2 (en) | 2014-04-02 | 2019-11-05 | Lintec Corporation | Adhesive sheet and method for producing adhesive sheet |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS52121644A (en) * | 1976-04-06 | 1977-10-13 | Nagoya Yukagaku Kogyo Kk | Adhesive composition and adhesive tape |
-
1988
- 1988-06-21 JP JP63152591A patent/JPH0798926B2/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS52121644A (en) * | 1976-04-06 | 1977-10-13 | Nagoya Yukagaku Kogyo Kk | Adhesive composition and adhesive tape |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009120805A (en) * | 2007-10-22 | 2009-06-04 | Nitto Denko Corp | Pressure-sensitive adhesive composition for optical film, pressure-sensitive adhesive layer for optical film, production method thereof, pressure-sensitive adhesive optical film and image display |
| US8962135B2 (en) | 2007-10-22 | 2015-02-24 | Nitto Denko Corporation | Pressure-sensitive adhesive composition for optical film, pressure-sensitive adhesive layer for optical film, production method thereof, pressure-sensitive adhesive optical film and image display |
| EP2072552A3 (en) * | 2007-12-20 | 2009-07-29 | Nitto Denko Corporation | Pressure-sensitive adhesive composition for optical films, pressure-sensitive adhesive optical film and image display |
| US8709597B2 (en) | 2008-02-15 | 2014-04-29 | Nitto Denko Corporation | Pressure-sensitive adhesive composition for optical films, pressure-sensitive adhesive optical film and image display |
| US8784987B2 (en) | 2008-03-14 | 2014-07-22 | Nitto Denko Corporation | Pressure-sensitive adhesive composition for optical films, pressure-sensitive adhesive optical film and image display |
| US9133368B2 (en) | 2011-08-31 | 2015-09-15 | Lintec Corporation | Adhesive sheet |
| WO2014051106A1 (en) | 2012-09-28 | 2014-04-03 | リンテック株式会社 | Adhesive sheet and method for manufacturing adhesive sheet |
| US9752061B2 (en) | 2012-09-28 | 2017-09-05 | Lintec Corporation | Adhesive sheet and method for manufacturing adhesive sheet |
| US10363718B2 (en) | 2014-04-02 | 2019-07-30 | Lintec Corporation | Adhesive sheet and adhesive sheet production method |
| US10465101B2 (en) | 2014-04-02 | 2019-11-05 | Lintec Corporation | Adhesive sheet and method for producing adhesive sheet |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0798926B2 (en) | 1995-10-25 |
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