JPH0344592B2 - - Google Patents
Info
- Publication number
- JPH0344592B2 JPH0344592B2 JP61154360A JP15436086A JPH0344592B2 JP H0344592 B2 JPH0344592 B2 JP H0344592B2 JP 61154360 A JP61154360 A JP 61154360A JP 15436086 A JP15436086 A JP 15436086A JP H0344592 B2 JPH0344592 B2 JP H0344592B2
- Authority
- JP
- Japan
- Prior art keywords
- meth
- acrylate
- weight
- parts
- alkyl group
- 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.)
- Expired - Lifetime
Links
- 239000003822 epoxy resin Substances 0.000 claims description 15
- 229920000647 polyepoxide Polymers 0.000 claims description 15
- -1 methacryloyl Chemical group 0.000 claims description 14
- 239000000178 monomer Substances 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 8
- 238000010438 heat treatment Methods 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 230000005855 radiation Effects 0.000 claims description 6
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 5
- 125000003700 epoxy group Chemical group 0.000 claims description 4
- 125000005395 methacrylic acid group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- 239000000853 adhesive Substances 0.000 description 29
- 230000001070 adhesive effect Effects 0.000 description 29
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 22
- 239000000203 mixture Substances 0.000 description 13
- 239000004820 Pressure-sensitive adhesive Substances 0.000 description 10
- 238000001723 curing Methods 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 7
- 229920000193 polymethacrylate Polymers 0.000 description 7
- 150000002431 hydrogen Chemical class 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 229920005862 polyol Polymers 0.000 description 4
- 150000003077 polyols Chemical class 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 3
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 3
- DPZSNGJNFHWQDC-ARJAWSKDSA-N (z)-2,3-diaminobut-2-enedinitrile Chemical compound N#CC(/N)=C(/N)C#N DPZSNGJNFHWQDC-ARJAWSKDSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000001678 irradiating effect Effects 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 229920003986 novolac Polymers 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- PIZHFBODNLEQBL-UHFFFAOYSA-N 2,2-diethoxy-1-phenylethanone Chemical compound CCOC(OCC)C(=O)C1=CC=CC=C1 PIZHFBODNLEQBL-UHFFFAOYSA-N 0.000 description 1
- BZUILZIKDIMXBK-UHFFFAOYSA-N 2-(oxiran-2-ylmethoxycarbonyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)OCC1OC1 BZUILZIKDIMXBK-UHFFFAOYSA-N 0.000 description 1
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 1
- KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-UHFFFAOYSA-N 0.000 description 1
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- ROHTVIURAJBDES-UHFFFAOYSA-N 2-n,2-n-bis(prop-2-enyl)-1,3,5-triazine-2,4,6-triamine Chemical compound NC1=NC(N)=NC(N(CC=C)CC=C)=N1 ROHTVIURAJBDES-UHFFFAOYSA-N 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 238000003848 UV Light-Curing Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000002390 adhesive tape Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 230000003712 anti-aging effect Effects 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 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
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 125000006226 butoxyethyl group Chemical group 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 125000003438 dodecyl 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])C([H])([H])C([H])([H])* 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000004134 energy conservation Methods 0.000 description 1
- 125000006232 ethoxy propyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000013007 heat curing Methods 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920006267 polyester film Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000007665 sagging Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
Description
【発明の詳細な説明】
技術分野
本発明は粘接着剤組成物に関し、詳しくは、紫
外線または放射線を照射すると粘着性を示し粘着
剤となり、その後加熱すると硬化可能な粘接着剤
組成物に関するものである。
従来技術
粘接着剤は、粘着性で仮接着し、その後硬化を
行ない接着するものである。一般に、粘接着剤
は、基材への塗布を容易にするために、有機溶剤
で希釈した溶液型である。このような溶液型粘接
着剤は、塗布後、有機溶剤を蒸発させるのに、乾
燥工程として長時間を必要とする。この場合使用
される有機溶剤は揮発性であり、燃えやすく、人
体に悪影響を及ぼすものが多く、その使用がしば
しば火災発生の原因となつたり、種々の公害問題
を引きおこしたりしている。
また、溶液型粘接着剤は、経済的見地、並びに
上記公害防止上の観点から溶剤回収装置の設置が
不可避とされるが、この装置は、一般に高価であ
つて、かつ設備的に大きな場所を必要とする。
従来の粘接着剤は上記の欠点を有していた。
発明の目的
本発明の目的は、紫外線または放射線を照射す
る粘着性を示し、粘着剤となり、その後加熱する
と硬化可能で、特に粘接着剤テープ等に利用可能
な粘接着剤組成物を提供することにある。
発明の具体的構成
本発明は、下記の一般式［Ａ］で示される単官
能アクリル系（メタクリル系を含む）モノマー10
〜60重量部と、
１分子中に少なくとも２個以上のアクリロイル
基（メタクリロイル基を含む）をもつ化合物0.01
〜10重量部と、
１分子中に少なくとも２個以上のエポキシ基を
もつ化合物40〜80重量部と、
エポキシ樹脂の潜在性硬化剤0.1〜20重量部
（上記４成分の合計を100重量部とする）とを有
し、紫外線または放射線の照射によつて粘着性を
示す程度まで硬化し、その後の加熱によつてさら
に硬化することを特徴とする粘接着剤組成物を提
供する。
ただし：ｎ＝１〜３の整数
R1＝Ｈ、CH3
R2＝CH2、C2H4、C3H6
R3：アルキル基、またはDETAILED DESCRIPTION OF THE INVENTION Technical Field The present invention relates to a pressure-sensitive adhesive composition, and more particularly to a pressure-sensitive adhesive composition that exhibits tackiness and becomes a pressure-sensitive adhesive when irradiated with ultraviolet rays or radiation, and that can be cured by subsequent heating. It is something. PRIOR ART Adhesives are adhesives that temporarily adhere and then harden to form an adhesive. Generally, adhesives are solution-type adhesives diluted with organic solvents to facilitate application to substrates. Such solution type adhesives require a long drying process to evaporate the organic solvent after application. The organic solvents used in this case are volatile, easily flammable, and often have an adverse effect on the human body, and their use often causes fires and causes various pollution problems. In addition, for solution-type adhesives, it is inevitable to install a solvent recovery device from an economic standpoint and the above-mentioned pollution prevention perspective, but this device is generally expensive and requires a large space. Requires. Conventional pressure-sensitive adhesives have the above-mentioned drawbacks. OBJECT OF THE INVENTION The object of the present invention is to provide a pressure-sensitive adhesive composition that exhibits tackiness when irradiated with ultraviolet rays or radiation, becomes a pressure-sensitive adhesive, and can be cured by subsequent heating, and can be used particularly for pressure-sensitive adhesive tapes, etc. It's about doing. Specific Structure of the Invention The present invention relates to a monofunctional acrylic (including methacrylic) monomer 10 represented by the following general formula [A].
~60 parts by weight and 0.01 of a compound having at least two or more acryloyl groups (including methacryloyl groups) in one molecule
~10 parts by weight, 40 to 80 parts by weight of a compound having at least two or more epoxy groups in one molecule, and 0.1 to 20 parts by weight of a latent curing agent for epoxy resin (the total of the above four components is 100 parts by weight). Provided is a pressure-sensitive adhesive composition which is characterized in that it has the following properties, is cured to the extent that it exhibits tackiness by irradiation with ultraviolet rays or radiation, and is further cured by subsequent heating. However: n = integer from 1 to 3 R 1 = H, CH 3 R 2 = CH 2 , C 2 H 4 , C 3 H 6 R 3 : Alkyl group, or
【式】 R4＝水素、アルキル基 R5＝水素、アルキル基 または[Formula] R 4 = hydrogen, alkyl group R 5 = hydrogen, alkyl group or
【式】
R6＝アルキル基
以下、本発明の構成について詳しく説明する。
(1) 本発明で用いる単官能（メタ）アクリル系モ
ノマーは、下記の一般式［Ａ］で示される。
ただし：ｎ＝１〜３
R1＝Ｈ、CH3
R2＝CH2、C2H4、C3H6
R3：アルキル基、または[Formula] R 6 =Alkyl group Hereinafter, the structure of the present invention will be explained in detail. (1) The monofunctional (meth)acrylic monomer used in the present invention is represented by the following general formula [A]. However: n = 1 to 3 R 1 = H, CH 3 R 2 = CH 2 , C 2 H 4 , C 3 H 6 R 3 : Alkyl group, or
【式】 R4＝水素、アルキル基 R5＝水素、アルキル基 または[Formula] R 4 = hydrogen, alkyl group R 5 = hydrogen, alkyl group or
【式】
R6＝アルキル基
上述の一般式［Ａ］で示される（メタ）アクリ
ル系モノマーとしては、例えばメトキシエチル
（メタ）アクリレート、メトキシプロピル（メタ）
アクリレート、エトキシエチル（メタ）アクリレ
ート、エトキシプロピル（メタ）アクリレート、
ブトキシエチル（メタ）アクリレート、ブトキシ
プロピル（メタ）アクリレート、フエノキシエチ
ル（メタ）アクリレート、フエノキシプロピル
（メタ）アクリレート、ノニルフエノキシエチル
（メタ）アクリレート、ノニルフエノキシプロピ
ル（メタ）アクリレート等が代表的に挙げられ
る。
(2) １分子中に少なくとも２個以上の（メタ）ア
クリロイル基をもつ化合物としては、構造的に
特に限定されるものではないが、例えばポリオ
ールポリ（メタ）アクリレート、変性ポリオー
ルポリ（メタ）アクリレート、ポリエステルポ
リ（メタ）アクリレート、エポキシポリ（メ
タ）アクリレート、ウレタンポリ（メタ）アク
リレート等が有効に利用される。ポリオールポ
リ（メタ）アクリレートには、ポリエチレング
リコールジ（メタ）アクリレート、ポリプロピ
レングリコールジ（メタ）アクリレート、ネオ
ペンチルグリコールジ（メタ）アクリレート、
１，６−ヘキサンジオールジ（メタ）アクリレ
ート、トリメチロールプロパントリ（メタ）ア
クリレート、ペンタエリスリトールトリ（メ
タ）アクリレート、ジペンタエリスリトールヘ
キサ（メタ）アクリレートなどがある。変性ポ
リオールポリ（メタ）アクリレートには、トリ
メチロールプロパンのプロピレンオキシド付加
物のトリ（メタ）アクリレート、ビスフエノー
ルＡのエチレンオキシド付加物のジ（メタ）ア
クリレートなどがある。
(3) １分子中に少なくとも２個のエポキシ基を有
する化合物としては、例えば、ビスフエノール
型エポキシ樹脂、フエノールノボラツク型エポ
キシ樹脂、クレゾールノボラツク型エポキシ樹
脂、フタル酸グリシジルエステル型エポキシ樹
脂、ダイマー酸型エポキシ樹脂、ポリグリコー
ル型エポキシ樹脂等を代表的に挙げることがで
きる。
(4) エポキシ樹脂の潜在性硬化剤としてはいかな
るものでもよいが、ジシアンジアミド
（DICY）三フツ化ホウ素−アミン・コンプレ
ツクス、有機酸ヒドラジツド、ジアミノマレオ
ニトリル（DAMN）、ジアリルメラミン、アミ
ンイミド、ポリアミンの塩、等が利用可能であ
る。
(5) さらに、本発明の組成物には、その性能を変
えない範囲内で上記(1)〜(4)以外の他の添加剤を
加えることができる。この添加剤は、例えば、
（メタ）アクリル酸のアルキルエステルモノマ
ー、光開始剤、光増感剤、重合禁止剤、充填
剤、顔料、タレ防止剤、分散剤、老化防止剤等
である。
（メタ）アクリル酸のアルキルエステルモノ
マーとしては、（メタ）アクリル酸ｎ−ブチル、
（メタ）アクリル酸−２−エチルヘキシル、（メ
タ）アクリル酸ドデシル等が添加可能である。
(6) 本発明の組成物は、放射線硬化の際は不要で
あるが、紫外線硬化を行なうときには、光開始
剤を必要とする。光開始剤としては、開裂タイ
プのもの、水素引き抜きタイプのものが有効に
使用される。
開裂タイプのものとしては、例えば、ベンゾ
インエチルエーテル、ジエトキシアセトフエノ
ン、ベンジルジメチルケタール、２−ヒドロキ
シ−２−メチルプロピオフエノン、１−ヒドロ
キシシクロヘキシルフエニルケトン等が挙げら
れる。
水素引き抜きタイプのものとしては、ベンジ
ル、ベンゾフエノン、２，４−ジエチルチオキ
サトン等が有効である。
光開始剤の使用量は組成物に対して好ましく
は0.001〜10wt％、さらに好ましくは0.01〜5wt
％の範囲である。
(7) 本発明の組成物中の各成分の配合比は、前記
(1)〜(4)の成分の合計を100重量部としたときに、
下記の通りとする。一般式［Ａ］で示される単
官能（メタ）アクリルモノマー系は、配合量が
多いほど紫外線照射後の粘着性にすぐれるが、
その後、加熱硬化を行なうためには、単官能
（メタ）アクリルモノマー系の配合量が10〜60
重量部、１分子中には少なくとも２個以上のエ
ポキシ基をもつ化合物が40〜80重量部が適当で
ある。
また、１分子中に少なくとも２個以上の（メ
タ）アクリロイル基をもつ化合物の配合量は、
（メタ）アクリロイル基の数やこの化合物の分子
量によつて異なるが、0.01〜10重量部が好まし
い。
エポキシ樹脂の潜在性硬化剤は、配合量が多い
ほぼ加熱時の硬化時間が短くなるが、反対にポツ
トライフが短かくなるので、0.1〜20重量部が好
適である。
実施例、比較例
以下に実施例、比較例を挙げて本発明を具体的
に説明する。粘着力、接着力の測定は次の方法で
行なつた。
(1) 粘着力
50μmのポリエステルフイルムの片面に、粘接
着剤の厚さが約100μmになるように粘接着剤を塗
布した後、紫外線硬化用高圧水銀ランプ（80W／
cm）のランプ下15cmの位置で10秒間紫外線を照射
し、粘着シートを作製した。該粘着シートをアル
ミ板（Ａ−1050P）に貼り付け、180度引き剥が
し粘着力を測定した。
(2) 接着力
アルミ板（Ａ−1050P）の片面に、粘接着剤の
厚さが約100μm、広さが25mm×25mmになるように
粘接着剤を塗布し紫外線硬化用高圧水銀ランプ
（80W／cm）のランプ下15cmの位置で10秒間紫外
線を照射した後、別のアルミ板（Ａ−1050P）に
貼り付け、150℃のオーブン内で20分間加熱硬化
させた。このテストピースを使い、せん断接着力
を測定した。
実施例１〜13、比較例１、２
第１表の配合に従い本発明の粘接着剤組成物を
作製し、上記の方法で粘着力及び接着力を測定し
た。
測定結果を第１表に示した。
実施例１〜３は、エポキシ樹脂と単官能アクリ
ルモノマー系の配合比を変えたものである。
実施例２、４〜７は、単官能アクリルモノマー
系の種類を変えたものである。
実施例２、８、９はエポキシ樹脂の種類を変え
たものである。
実施例２、10、11は多官能アクリル化合物の種
類を変えたものである。
実施例２、12、13はエポキシ樹脂の潜在性硬化
剤の種類を変えたものである。
比較例１、２は、組成比が本発明の範囲外であ
るものである。
第１表に示したように、本発明の粘接着剤組成
物は、0.7〜1.3Kg／25mmの粘着力と90〜135Kg／
cm2のせん断接着力を有する。
比較例 １、２
比較例１の場合、エポキシ樹脂の量が多く単官
能アクリルモノマー系の量が少ないため、紫外線
照射時に硬化しなかつた。
比較例２の場合、エポキシ樹脂の量が少なく、
単官能アクリルモノマー系の量が多いため、粘着
力は1.7Kg／25mmとすぐれているが、接着力は10
Kg／cm2と非常に弱い。[Formula] R 6 = alkyl group Examples of the (meth)acrylic monomer represented by the above general formula [A] include methoxyethyl (meth)acrylate, methoxypropyl (meth)
acrylate, ethoxyethyl (meth)acrylate, ethoxypropyl (meth)acrylate,
Butoxyethyl (meth)acrylate, butoxypropyl (meth)acrylate, phenoxyethyl (meth)acrylate, phenoxypropyl (meth)acrylate, nonylphenoxyethyl (meth)acrylate, nonylphenoxypropyl (meth)acrylate, etc. These are representative examples. (2) Compounds having at least two (meth)acryloyl groups in one molecule are not particularly limited structurally, but include, for example, polyol poly(meth)acrylate, modified polyol poly(meth)acrylate , polyester poly(meth)acrylate, epoxy poly(meth)acrylate, urethane poly(meth)acrylate, etc. are effectively used. Polyol poly(meth)acrylate includes polyethylene glycol di(meth)acrylate, polypropylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate,
Examples include 1,6-hexanediol di(meth)acrylate, trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, and dipentaerythritol hexa(meth)acrylate. Examples of the modified polyol poly(meth)acrylate include tri(meth)acrylate of a propylene oxide adduct of trimethylolpropane and di(meth)acrylate of an ethylene oxide adduct of bisphenol A. (3) Compounds having at least two epoxy groups in one molecule include, for example, bisphenol type epoxy resin, phenol novolak type epoxy resin, cresol novolak type epoxy resin, phthalate glycidyl ester type epoxy resin, dimer Representative examples include acid type epoxy resins and polyglycol type epoxy resins. (4) Any latent curing agent for epoxy resins may be used, including dicyandiamide (DICY), boron trifluoride-amine complex, organic acid hydrazide, diaminomaleonitrile (DAMN), diallylmelamine, amine imide, and polyamine. salt, etc. are available. (5) Furthermore, other additives other than the above (1) to (4) can be added to the composition of the present invention within a range that does not change its performance. This additive is, for example,
These include (meth)acrylic acid alkyl ester monomers, photoinitiators, photosensitizers, polymerization inhibitors, fillers, pigments, anti-sagging agents, dispersants, anti-aging agents, and the like. As the alkyl ester monomer of (meth)acrylic acid, n-butyl (meth)acrylate,
2-ethylhexyl (meth)acrylate, dodecyl (meth)acrylate, etc. can be added. (6) The composition of the present invention does not require a photoinitiator when curing with radiation, but does require a photoinitiator when curing with ultraviolet light. As the photoinitiator, cleavage type and hydrogen abstraction type are effectively used. Examples of the cleavage type include benzoin ethyl ether, diethoxyacetophenone, benzyl dimethyl ketal, 2-hydroxy-2-methylpropiophenone, and 1-hydroxycyclohexyl phenyl ketone. As the hydrogen abstracting type, benzyl, benzophenone, 2,4-diethylthioxatone, etc. are effective. The amount of photoinitiator used is preferably 0.001 to 10wt%, more preferably 0.01 to 5wt% based on the composition.
% range. (7) The blending ratio of each component in the composition of the present invention is as described above.
When the total of components (1) to (4) is 100 parts by weight,
The following shall apply. The monofunctional (meth)acrylic monomer system represented by the general formula [A] has better adhesiveness after UV irradiation as the amount of the monomer is larger.
After that, in order to perform heat curing, the blending amount of the monofunctional (meth)acrylic monomer system must be 10 to 60%.
The appropriate amount of the compound having at least two or more epoxy groups per molecule is 40 to 80 parts by weight. In addition, the amount of compound having at least two (meth)acryloyl groups in one molecule is as follows:
Although it varies depending on the number of (meth)acryloyl groups and the molecular weight of the compound, it is preferably 0.01 to 10 parts by weight. The latent curing agent for the epoxy resin is preferably used in an amount of 0.1 to 20 parts by weight, since the curing time during heating will be shortened if the amount is large, but the pot life will be shortened. EXAMPLES AND COMPARATIVE EXAMPLES The present invention will be specifically described below with reference to Examples and Comparative Examples. Adhesive strength and adhesive strength were measured by the following method. (1) Adhesive strength After applying adhesive to one side of a 50 μm polyester film to a thickness of approximately 100 μm, a high-pressure mercury lamp for ultraviolet curing (80 W/
A pressure-sensitive adhesive sheet was prepared by irradiating ultraviolet light for 10 seconds at a position 15 cm below a lamp (cm). The adhesive sheet was attached to an aluminum plate (A-1050P) and peeled off at 180 degrees to measure the adhesive strength. (2) Adhesive strength Apply adhesive to one side of an aluminum plate (A-1050P) so that the thickness of the adhesive is approximately 100 μm and the area is 25 mm x 25 mm, and apply it using a high-pressure mercury lamp for UV curing. After irradiating it with ultraviolet light for 10 seconds at a position 15 cm below a (80 W/cm) lamp, it was attached to another aluminum plate (A-1050P) and cured by heating in an oven at 150°C for 20 minutes. Using this test piece, the shear adhesive strength was measured. Examples 1 to 13, Comparative Examples 1 and 2 Adhesive compositions of the present invention were prepared according to the formulations shown in Table 1, and the adhesive strength and adhesive strength were measured using the methods described above. The measurement results are shown in Table 1. In Examples 1 to 3, the blending ratio of the epoxy resin and the monofunctional acrylic monomer was changed. In Examples 2 and 4 to 7, the type of monofunctional acrylic monomer was changed. In Examples 2, 8, and 9, the type of epoxy resin was changed. In Examples 2, 10, and 11, the type of polyfunctional acrylic compound was changed. In Examples 2, 12, and 13, the type of latent curing agent used in the epoxy resin was changed. Comparative Examples 1 and 2 have composition ratios outside the scope of the present invention. As shown in Table 1, the adhesive composition of the present invention has an adhesive strength of 0.7 to 1.3 Kg/25 mm and an adhesive strength of 90 to 135 Kg/25 mm.
It has a shear adhesion strength of cm 2 . Comparative Examples 1 and 2 In Comparative Example 1, the amount of epoxy resin was large and the amount of monofunctional acrylic monomer system was small, so it was not cured when irradiated with ultraviolet rays. In the case of Comparative Example 2, the amount of epoxy resin was small;
Due to the large amount of monofunctional acrylic monomer system, the adhesive strength is excellent at 1.7Kg/25mm, but the adhesive strength is 10Kg/25mm.
Very weak at Kg/cm 2 .
【表】【table】
【表】【table】
【表】
発明の効果
本発明の粘接着剤組成物は、紫外線または放射
線を照射すると粘着性を示し、粘着剤となるた
め、塗布工程においては有機溶剤で希釈する必要
がなく、公害防止や省エネルギーの観点において
有利である。
また、粘接着剤として、初期接着時の作業性が
良く、その後加熱硬化し、接着力や耐熱性にすぐ
れる。さらに、２液硬化型のように硬化剤を混合
する必要がない１液型なので取り扱いが容易であ
る。
特に粘接着テープに好適に利用できる。[Table] Effects of the Invention The adhesive composition of the present invention becomes adhesive when irradiated with ultraviolet rays or radiation and becomes an adhesive, so there is no need to dilute it with an organic solvent during the coating process, and it is effective in preventing pollution and This is advantageous in terms of energy conservation. In addition, as a pressure-sensitive adhesive, it has good workability during initial adhesion, is then cured by heating, and has excellent adhesive strength and heat resistance. Furthermore, it is easy to handle because it is a one-component type that does not require mixing a curing agent unlike a two-component type. In particular, it can be suitably used for adhesive tapes.
Claims (1)
ル系（メタクリル系を含む）モノマー10〜60重量
部と、 １分子中に少なくとも２個以上のアクリロイル
基（メタクリロイル基を含む）をもつ化合物0.01
〜10重量部と、 １分子中に少なくとも２個以上のエポキシ基を
もつ化合物40〜80重量部と、 エポキシ樹脂の潜在性硬化剤0.1〜20重量部
（上記４成分の合計を100重量部とする）とを有
し、 紫外線または放射線の照射によつて粘着性を示
す程度まで硬化し、その後の加熱によつてさらに
硬化することを特徴とする粘接着剤組成物。 ただし：ｎ＝１〜３の整数 R1＝Ｈ、CH3 R2＝CH2、C2H4、C3H6 R3：アルキル基、または 【式】 （R4＝水素、アルキル基、 R5＝水素、アルキル基、） または【式】 （R6＝アルキル基、）[Scope of Claims] 1. 10 to 60 parts by weight of a monofunctional acrylic (including methacrylic) monomer represented by the following general formula [A], and at least two or more acryloyl groups (methacryloyl groups) in one molecule. 0.01
~10 parts by weight, 40 to 80 parts by weight of a compound having at least two or more epoxy groups in one molecule, and 0.1 to 20 parts by weight of a latent curing agent for epoxy resin (the total of the above four components is 100 parts by weight). ), which is cured to the extent that it exhibits tackiness by irradiation with ultraviolet rays or radiation, and is further cured by subsequent heating. However: n = integer of 1 to 3 R 1 = H, CH 3 R 2 = CH 2 , C 2 H 4 , C 3 H 6 R 3 : Alkyl group, or [Formula] (R 4 = hydrogen, alkyl group, R 5 = hydrogen, alkyl group, ) or [Formula] (R 6 = alkyl group,)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15436086A JPS6310680A (en) | 1986-07-01 | 1986-07-01 | Tacky adhesive composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15436086A JPS6310680A (en) | 1986-07-01 | 1986-07-01 | Tacky adhesive composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6310680A JPS6310680A (en) | 1988-01-18 |
| JPH0344592B2 true JPH0344592B2 (en) | 1991-07-08 |
Family
ID=15582452
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP15436086A Granted JPS6310680A (en) | 1986-07-01 | 1986-07-01 | Tacky adhesive composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6310680A (en) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2519543B2 (en) * | 1989-10-07 | 1996-07-31 | 秀雄 浜田 | Adhesive composition, adhesive composition layer and transfer sheet having the layer |
| JPH085277B2 (en) * | 1990-10-05 | 1996-01-24 | 秀雄 浜田 | Transfer sheet |
| US5602221A (en) * | 1993-11-10 | 1997-02-11 | Minnesota Mining And Manufacturing Company | Pressure sensitive adhesives with good low energy surface adhesion |
| US5616670A (en) * | 1993-11-10 | 1997-04-01 | Minnesota Mining And Manufacturing Company | Pressure sensitive adhesives with good oily surface adhesion |
| US5683798A (en) * | 1993-11-10 | 1997-11-04 | Minnesota Mining And Manufacturing Company | Tackified pressure sensitive adhesives |
| US5654387A (en) * | 1993-11-10 | 1997-08-05 | Minnesota Mining And Manufacturing Company | Pressure sensitive adhesives |
| JP2001031939A (en) * | 1999-07-26 | 2001-02-06 | Nitto Denko Corp | Heat-bonding adhesive composition and adhesive sheet or like coated therewith |
| JP4607270B2 (en) * | 1999-11-24 | 2011-01-05 | 日東電工株式会社 | Thermosetting adhesive and its adhesive sheets |
| JP5684243B2 (en) * | 2010-04-30 | 2015-03-11 | 日東電工株式会社 | Method for producing laminate using adhesive composition |
| JPWO2022181564A1 (en) * | 2021-02-24 | 2022-09-01 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5865717A (en) * | 1981-10-15 | 1983-04-19 | Toyo Ink Mfg Co Ltd | Actinic ray-curable composition |
-
1986
- 1986-07-01 JP JP15436086A patent/JPS6310680A/en active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5865717A (en) * | 1981-10-15 | 1983-04-19 | Toyo Ink Mfg Co Ltd | Actinic ray-curable composition |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6310680A (en) | 1988-01-18 |
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