JPH0414153B2 - - Google Patents

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Publication number
JPH0414153B2
JPH0414153B2 JP58134089A JP13408983A JPH0414153B2 JP H0414153 B2 JPH0414153 B2 JP H0414153B2 JP 58134089 A JP58134089 A JP 58134089A JP 13408983 A JP13408983 A JP 13408983A JP H0414153 B2 JPH0414153 B2 JP H0414153B2
Authority
JP
Japan
Prior art keywords
weight
parts
polyester film
irradiation
ultraviolet rays
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
Application number
JP58134089A
Other languages
Japanese (ja)
Other versions
JPS6026074A (en
Inventor
Hiroshi Yoshida
Original Assignee
Nagoya City
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Nagoya City filed Critical Nagoya City
Priority to JP58134089A priority Critical patent/JPS6026074A/en
Publication of JPS6026074A publication Critical patent/JPS6026074A/en
Publication of JPH0414153B2 publication Critical patent/JPH0414153B2/ja
Granted legal-status Critical Current

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  • Adhesives Or Adhesive Processes (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Description

【発明の詳細な説明】 本発明は、CH2=CHCOOR(Rは炭素数4以上
のアルキル基)を主成分として使い、2段階の紫
外線照射により感圧性接着剤を製造するための感
光性樹脂組成物に関するものである。
DETAILED DESCRIPTION OF THE INVENTION The present invention provides a photosensitive resin for producing a pressure-sensitive adhesive through two-step ultraviolet irradiation using CH 2 =CHCOOR (R is an alkyl group having 4 or more carbon atoms) as a main component. The present invention relates to a composition.

従来からよく使われている溶剤タイプの感圧性
接着剤は、製造工程で有機溶剤を使用するため、
溶剤回収のための費用、作業環境の汚染に対する
配慮、火災の危険等が伴い、無溶剤タイプへの転
換がはかられている。そのため、水系エマルジヨ
ンタイプ、ホツトメルトタイプ、液状硬化タイプ
等の感圧性接着剤の開発研究が数多く行われてい
る。紫外線照射による感圧性接着剤の製造につい
ての試みも行われているが、粘着力等の性能、製
造工程における制御の難しさが問題になつてい
る。
Solvent-type pressure-sensitive adhesives, which have traditionally been commonly used, use organic solvents in the manufacturing process, so
Due to the costs associated with solvent recovery, consideration for contamination of the working environment, and the risk of fire, efforts are being made to switch to solvent-free types. For this reason, much research and development has been conducted on the development of pressure-sensitive adhesives such as water-based emulsion types, hot melt types, and liquid curing types. Attempts have been made to produce pressure-sensitive adhesives using ultraviolet irradiation, but problems such as adhesive strength and difficulty in controlling the production process have been encountered.

本発明は、CH2=CHCOOR(Rは炭素数4以上
のアルキル基)で示されるアクリル酸エステル
100重量部とベンゾインイソプロピルエーテル
0.01〜0.4重量部の混合溶液に第1段階の紫外線
照射を行うと、架橋したアクリル酸エステルポリ
マーが簡単に得られ、さらに、この樹脂組成物
100重量部にアクリル酸エステルモノマー50〜150
重量部多官能性アクリル酸エステル0〜5重量
部、アクリル酸0〜20重量部、光重合開始剤0.1
〜5重量部を加えて混合した感光性樹脂組成物を
基材へ塗布した後、第2段階の紫外線照射を行う
ことにより強固な粘着力を示す感圧性接着剤を製
造できることを発見したことに基づいている。
The present invention relates to acrylic esters represented by CH 2 =CHCOOR (R is an alkyl group having 4 or more carbon atoms)
100 parts by weight and benzoin isopropyl ether
When 0.01 to 0.4 parts by weight of the mixed solution is irradiated with ultraviolet light in the first step, a crosslinked acrylic acid ester polymer can be easily obtained, and furthermore, this resin composition
100 parts by weight of acrylic acid ester monomer 50-150
Parts by weight: 0 to 5 parts by weight of polyfunctional acrylic ester, 0 to 20 parts by weight of acrylic acid, 0.1 part by weight of photopolymerization initiator
We have discovered that it is possible to produce a pressure-sensitive adhesive that exhibits strong adhesive strength by applying a photosensitive resin composition mixed with ~5 parts by weight to a substrate and then irradiating it with ultraviolet rays in the second step. Based on.

このような試みは、特開昭56−30410号公報、
特表昭57−500105号公報、特表昭57−500106号公
報、特表昭57−500130号公報、米国特許第
4181752号明細書、特表昭58−500130号、特開昭
54−17942号公報に開示されている。これらは、
2−エチルヘキシルアクリレート等のアクリル酸
エステルと光重合開始剤からなる組成物を紫外線
照射により、部分重合物(シロツプ)とした後、
基材上に塗布し、さらに紫外線照射することによ
り、硬化させる感圧接着剤用感光性組成物である
が、2段階目の紫外線照射前に、分子間で架橋を
起こさせる成分の添加で粘着特性を向上させるこ
とを特徴としている。即ち、特開昭56−30410号
公報では酸化性錫塩、特表昭57−500105号公報で
は発色団置換ハロメチル−s−トリアジン、特表
昭−57−500106号公報ではハロメチル−s−トリ
アジンを利用し、優れた粘着力を得ようとするも
のである。米国特許第4181752号明細書では、照
射波長の規制による重合物の分子量規制、特表昭
58−500130号公報、特開昭54−17942号公報では、
N−ビニルピロリドンの添加による架橋効果を与
えたものである。また、特表昭57−500130号公報
は、はんだマスク組成物に関するものである。前
述の発明は、全て二段階目紫外線照射で重合物を
架橋することで粘着剤の特性向上を図るもので、
本発明の感圧性接着剤製造用の感光性樹脂組成物
とは手段を異にしている。
Such an attempt was made in Japanese Unexamined Patent Publication No. 56-30410,
Special Publication No. 57-500105, Publication No. 57-500106, Publication No. 57-500130, U.S. Patent No.
Specification No. 4181752, Special Publication No. 58-500130, JP
It is disclosed in Publication No. 54-17942. these are,
After a composition consisting of an acrylic ester such as 2-ethylhexyl acrylate and a photopolymerization initiator is irradiated with ultraviolet rays to form a partially polymerized product (syrup),
This is a photosensitive composition for pressure-sensitive adhesives that is applied onto a substrate and cured by further irradiation with ultraviolet rays.Before the second step of irradiation with ultraviolet rays, a component that causes crosslinking between molecules is added to increase the adhesiveness. It is characterized by improving properties. That is, JP-A No. 56-30410 uses oxidizing tin salts, Japanese Patent Publication No. 57-500105 uses chromophore-substituted halomethyl-s-triazine, and Japanese Patent Application No. 57-500106 uses halomethyl-s-triazine. The aim is to utilize this technology to obtain superior adhesive strength. U.S. Pat.
In Publication No. 58-500130 and Japanese Unexamined Patent Publication No. 17942-1987,
A crosslinking effect is imparted by the addition of N-vinylpyrrolidone. Furthermore, Japanese Patent Publication No. 57-500130 relates to a solder mask composition. All of the above-mentioned inventions aim to improve the properties of adhesives by crosslinking the polymer in the second stage of ultraviolet irradiation.
The method is different from that of the photosensitive resin composition for producing a pressure-sensitive adhesive of the present invention.

CH2=CHCOOR(Rは炭素数4以上のアルキル
基)で示されるアクリル酸エステル100重量部に
ベンゾインイソアルキルエーテルのような光重合
開始剤0.01〜0.4重量部加えた混合液に一定方向
から紫外線を照射すると、CH2=CHCOOR(Rは
炭素数4以上のアルキル基)で示されるアクリル
酸エステルは、光重合してモノマーとポリマーの
混合状態を経由した後、混合液全体がポリマーと
なる。このポリマーは、部分的に架橋しており、
アクリル酸エステルモノマー、多官能性アクリル
モノマー、光重合開始剤と撹拌・混合してつくつ
た感光性樹脂組成物をポリエステルフイルム、ポ
リエチレンフイルム等の基材へ一定膜厚で塗布
後、紫外線照射すると優れた粘着力を示す感圧性
接着剤が得られる。
A mixture of 100 parts by weight of acrylic ester represented by CH 2 =CHCOOR (R is an alkyl group having 4 or more carbon atoms) and 0.01 to 0.4 parts by weight of a photopolymerization initiator such as benzoin isoalkyl ether is exposed to ultraviolet light from a certain direction. When irradiated with , the acrylic acid ester represented by CH 2 =CHCOOR (R is an alkyl group having 4 or more carbon atoms) undergoes photopolymerization and passes through a mixed state of monomer and polymer, and then the entire mixture becomes a polymer. This polymer is partially cross-linked,
A photosensitive resin composition prepared by stirring and mixing an acrylic acid ester monomer, a polyfunctional acrylic monomer, and a photopolymerization initiator can be applied to a base material such as a polyester film or polyethylene film at a constant thickness, and then irradiated with ultraviolet rays. A pressure-sensitive adhesive is obtained which exhibits a high adhesive strength.

実際には、感光性樹脂組成物をポリエステルマ
ツトフイルムに塗布してからポリエステルフイル
ムを圧着し、ポリエステルフイルム側から紫外線
を照射する。照射後、ポリエステルマツトフイル
ムとポリエステルフイルム間の180度剥離強さを
測定する。或いは、上記感光性樹脂組成物を剥離
紙の上に塗布し、塗布膜の上にポリエステルフイ
ルムをかぶせ、ポリエステル側から紫外線を照射
した後、ポリエステルフイルムと剥離紙を引き剥
すと塗布膜は、ポリエステルフイルム面へ移行
し、粘着剤層を形成する。この粘着剤層をステン
レススチール((SUS)板に2Kgの荷重で張り付
けた後、180度剥離強さを測定する。180度剥離強
さの測定は、テンシロン型引張試験機を使い、引
張速度は20mm/分である。このようにして測定し
た180度剥離強さは、300g/15mm以上の強度が得
られ、感圧性接着剤としての粘着力を充分に満足
する。
In practice, a photosensitive resin composition is applied to a polyester matte film, the polyester film is then pressure-bonded, and ultraviolet rays are irradiated from the polyester film side. After irradiation, measure the 180 degree peel strength between the polyester matte film and the polyester film. Alternatively, the above photosensitive resin composition is applied onto a release paper, a polyester film is placed over the coating film, ultraviolet rays are irradiated from the polyester side, and the polyester film and release paper are peeled off, and the coating film becomes a polyester film. It migrates to the film surface and forms an adhesive layer. After attaching this adhesive layer to a stainless steel (SUS) plate with a load of 2 kg, the 180 degree peel strength is measured.The 180 degree peel strength is measured using a Tensilon type tensile tester, and the tensile speed is 20 mm/min. The 180 degree peel strength measured in this way was 300 g/15 mm or more, which fully satisfies the adhesive force as a pressure sensitive adhesive.

以下、本発明の実施例を示すが、本発明の範囲
は、下記の実施例に限定されるものではない。
Examples of the present invention will be shown below, but the scope of the present invention is not limited to the following examples.

実施例 1 超高圧水銀灯(東芝製SHL100UV)から7
cmの距離に、ベンゾインプロピルエーテルを3.9
mg/mlを含むアクリル酸−2−エチルヘキシル溶
液を1ml入れた内径7mmのガラス製試験管を置
き、5分間紫外線を照射する。照射後の溶液は半
固化の状態で、良く撹拌・混合すると、塗布可能
になる。撹拌・混合後溶液をポリエステルマツト
フイルム(75μm)に塗布し、透明なポリエステ
ルフイルム(20μm)を圧着し、超高圧水銀灯か
ら7cm離しておき、15分間紫外線を照射する。次
いで、テンシロン型引張試験機で20mm/分の引張
速度でフイルム間の180度剥離強さを測定すると、
120g/15mmであつた。
Example 1 7 from ultra-high pressure mercury lamp (SHL100UV made by Toshiba)
benzoinpropyl ether at a distance of 3.9 cm.
A glass test tube with an inner diameter of 7 mm containing 1 ml of 2-ethylhexyl acrylate solution containing mg/ml was placed and irradiated with ultraviolet rays for 5 minutes. The solution after irradiation is in a semi-solid state and can be coated by stirring and mixing well. After stirring and mixing, the solution is applied to a polyester mat film (75 μm), a transparent polyester film (20 μm) is crimped, and the solution is irradiated with ultraviolet light for 15 minutes at a distance of 7 cm from an ultra-high pressure mercury lamp. Next, the 180 degree peel strength between the films was measured using a tensilon type tensile tester at a tensile speed of 20 mm/min.
It was 120g/15mm.

実施例 2 実施例1と同一条件で、2.1mg/mlのベンゾイ
ンイソプロピルエーテルを含むアクリル酸−2−
エチルヘキシルの溶液に5分間紫外線を照射し、
撹拌・混合後の溶液を剥離紙の上に塗布し、透明
なポリエステルフイルム(30μm)をかぶせ、ス
ペーサーで塗布膜厚を約30μmに調節する。ポリ
エステルフイルムと剥離紙を圧着後、プリンター
のケミカルランプを光源として紫外線を照射す
る。一定時間照射後、ポリエステルフイルムを剥
離紙から引き剥し、ポリエステルフイルム上に形
成された粘着剤層をステンレススチール(SUS)
板に2Kgの荷重で張り付け、テンシロン型引張試
験機を使い、20mm/分の引張速度で180度剥離強
さを測定すると、5分間照射で30g/15mm、15分
間照射で70g/15mm、120分照射で150g/15mmで
あつた。
Example 2 Acrylic acid-2-containing 2.1 mg/ml benzoin isopropyl ether was prepared under the same conditions as in Example 1.
Irradiate the ethylhexyl solution with ultraviolet light for 5 minutes,
After stirring and mixing, apply the solution onto release paper, cover with a transparent polyester film (30 μm), and adjust the coating thickness to approximately 30 μm using a spacer. After bonding the polyester film and release paper, UV light is irradiated using the printer's chemical lamp as a light source. After irradiation for a certain period of time, the polyester film is peeled off from the release paper and the adhesive layer formed on the polyester film is made of stainless steel (SUS).
When pasted on a board with a load of 2 kg and measured 180 degree peel strength at a tensile speed of 20 mm/min using a Tensilon type tensile tester, it was 30 g/15 mm after 5 minutes of irradiation, 70 g/15 mm after 15 minutes of 120 minutes. It was 150g/15mm by irradiation.

実施例 3 実施例1と同一条件で、1.9mg/mlのベンゾイ
ンイソプロピルエーテルを含むアクリル酸−2−
エチルヘキシルの溶液に5分間紫外線を照射して
得られる重合溶液100重量部にヘキサングリコー
ルジアクリレート0.03重量部を加え、撹拌・混合
後、剥離紙の上に塗布し、透明なポリエステルフ
イルムをかぶせ、実施例2と同様な条件で紫外線
を照射する。一定時間照射後、ポリエステルフイ
ルムと剥離紙を引き剥し、ポリエステルフイルム
上に形成された粘着剤層をステンレススチール
(SUS)板上に2Kgの荷重で貼り付け、テンシロ
ン型引張試験機を使い、20mm/分の引張速度で
180度剥離強さを測定すると、15分間照射で180
g/15mmであつた。
Example 3 Acrylic acid-2-containing 1.9 mg/ml benzoin isopropyl ether was prepared under the same conditions as in Example 1.
Add 0.03 parts by weight of hexane glycol diacrylate to 100 parts by weight of a polymerization solution obtained by irradiating an ethylhexyl solution with ultraviolet rays for 5 minutes, stir and mix, apply on release paper, cover with a transparent polyester film, and carry out the process. Ultraviolet rays are irradiated under the same conditions as in Example 2. After irradiation for a certain period of time, the polyester film and release paper were peeled off, and the adhesive layer formed on the polyester film was pasted on a stainless steel (SUS) plate with a load of 2 kg. At a tensile speed of
When measuring 180 degree peel strength, it was 180 after 15 minutes of irradiation.
g/15mm.

実施例 4 実施例1と同一条件で、1.9mg/1mlのベンゾ
インイソプロピルエーテルを含むアクリル酸−2
−エチルヘキシルの溶液に5分間紫外線を照射・
撹拌・混合して得られる溶液100重量部にヘキサ
ングリコールジアクリレート0.17重量部、アクリ
ル酸14重量部、ベンゾインイソプロピルエーテル
0.5重量部を混合した感光性樹脂組成物をポリエ
ステルマツトフイルム(75μm)に塗布し、透明
なポリエステルフイルム(20μm)を圧着し、プ
リンターのケミカルランプを光源として紫外線を
照射する。一定時間照射後、ポリエステルフイル
ムとポリエステルマツトフイルム間の180度剥離
強さをテンシロン型張試験機、20mm/分の引張速
度で測定すると、10分間照射で500g/15mmであ
つた。
Example 4 Acrylic acid-2 containing 1.9 mg/1 ml of benzoin isopropyl ether under the same conditions as Example 1.
- Irradiate ultraviolet light to ethylhexyl solution for 5 minutes.
0.17 parts by weight of hexane glycol diacrylate, 14 parts by weight of acrylic acid, and benzoin isopropyl ether to 100 parts by weight of the solution obtained by stirring and mixing.
A photosensitive resin composition mixed with 0.5 parts by weight is applied to a polyester matte film (75 μm), a transparent polyester film (20 μm) is pressed and irradiated with ultraviolet rays using a printer's chemical lamp as a light source. After irradiation for a certain period of time, the 180 degree peel strength between the polyester film and the polyester matte film was measured using a Tensilon tension tester at a tensile rate of 20 mm/min, and it was found to be 500 g/15 mm after 10 minutes of irradiation.

Claims (1)

【特許請求の範囲】[Claims] 1 CH2=CHCOOR(Rは炭素数4以上のアルキ
ル基)で示されるアクリル酸エステル100重量部、
ベンゾインイソアルキルエーテル0.01〜0.4重量
部の組成物に紫外線を照射して得られる重合物
100重量部、前記アクリル酸エステル50〜150重量
部、多官能性アクリル酸エステル0〜5重量部、
アクリル酸0〜20重量部、光重合開始剤0.1〜5
重量部を混合して得られる感圧性接着剤製造用の
感光性樹脂組成物。
100 parts by weight of acrylic ester represented by CH 2 =CHCOOR (R is an alkyl group having 4 or more carbon atoms),
Polymer obtained by irradiating a composition containing 0.01 to 0.4 parts by weight of benzoin isoalkyl ether with ultraviolet rays
100 parts by weight, 50 to 150 parts by weight of the acrylic ester, 0 to 5 parts by weight of polyfunctional acrylic ester,
Acrylic acid 0-20 parts by weight, photoinitiator 0.1-5
A photosensitive resin composition for producing a pressure-sensitive adhesive obtained by mixing parts by weight.
JP58134089A 1983-07-21 1983-07-21 Photosensitive resin composition for preparing pressure- sensitive adhesive Granted JPS6026074A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP58134089A JPS6026074A (en) 1983-07-21 1983-07-21 Photosensitive resin composition for preparing pressure- sensitive adhesive

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP58134089A JPS6026074A (en) 1983-07-21 1983-07-21 Photosensitive resin composition for preparing pressure- sensitive adhesive

Publications (2)

Publication Number Publication Date
JPS6026074A JPS6026074A (en) 1985-02-08
JPH0414153B2 true JPH0414153B2 (en) 1992-03-11

Family

ID=15120160

Family Applications (1)

Application Number Title Priority Date Filing Date
JP58134089A Granted JPS6026074A (en) 1983-07-21 1983-07-21 Photosensitive resin composition for preparing pressure- sensitive adhesive

Country Status (1)

Country Link
JP (1) JPS6026074A (en)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6026074A (en) * 1983-07-21 1985-02-08 Nagoyashi Photosensitive resin composition for preparing pressure- sensitive adhesive
DE3886470T2 (en) * 1987-08-14 1994-07-14 Minnesota Mining & Mfg Pressure sensitive adhesive.
JP3183726B2 (en) * 1992-09-17 2001-07-09 積水化学工業株式会社 Photoreactive composition and method for producing transparent laminate
JP3510722B2 (en) * 1995-10-18 2004-03-29 積水化学工業株式会社 Method for manufacturing viscoelastic sheet
JP5235294B2 (en) * 2006-11-10 2013-07-10 日東電工株式会社 Heat-foaming type removable acrylic adhesive tape or sheet
JP2012082433A (en) * 2011-12-02 2012-04-26 Nitto Denko Corp Heat-foamable re-releasable acrylic adhesive tape or sheet

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2884126A (en) * 1955-11-18 1959-04-28 Minnesota Mining & Mfg Pressure-sensitive adhesive sheet material
JPS5417942A (en) * 1977-07-09 1979-02-09 Sony Corp Adhesive mass
US4181752A (en) * 1974-09-03 1980-01-01 Minnesota Mining And Manufacturing Company Acrylic-type pressure sensitive adhesives by means of ultraviolet radiation curing
JPS5630410A (en) * 1979-08-20 1981-03-27 Minnesota Mining & Mfg Photopolymerizable mixture
JPS58108277A (en) * 1981-12-21 1983-06-28 Dainippon Printing Co Ltd Ionizing radiation curing-type pressure-sensitive adhesive composition
JPS6026074A (en) * 1983-07-21 1985-02-08 Nagoyashi Photosensitive resin composition for preparing pressure- sensitive adhesive

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4364972A (en) * 1981-01-16 1982-12-21 Minnesota Mining And Manufacturing Company Pressure-sensitive adhesive copolymers of acrylic acid ester and N-vinyl pyrrolidone

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2884126A (en) * 1955-11-18 1959-04-28 Minnesota Mining & Mfg Pressure-sensitive adhesive sheet material
US4181752A (en) * 1974-09-03 1980-01-01 Minnesota Mining And Manufacturing Company Acrylic-type pressure sensitive adhesives by means of ultraviolet radiation curing
JPS5417942A (en) * 1977-07-09 1979-02-09 Sony Corp Adhesive mass
JPS5630410A (en) * 1979-08-20 1981-03-27 Minnesota Mining & Mfg Photopolymerizable mixture
JPS58108277A (en) * 1981-12-21 1983-06-28 Dainippon Printing Co Ltd Ionizing radiation curing-type pressure-sensitive adhesive composition
JPS6026074A (en) * 1983-07-21 1985-02-08 Nagoyashi Photosensitive resin composition for preparing pressure- sensitive adhesive

Also Published As

Publication number Publication date
JPS6026074A (en) 1985-02-08

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