JPH02123182A - Re-releasing-type tack agent - Google Patents
Re-releasing-type tack agentInfo
- Publication number
- JPH02123182A JPH02123182A JP63276892A JP27689288A JPH02123182A JP H02123182 A JPH02123182 A JP H02123182A JP 63276892 A JP63276892 A JP 63276892A JP 27689288 A JP27689288 A JP 27689288A JP H02123182 A JPH02123182 A JP H02123182A
- Authority
- JP
- Japan
- Prior art keywords
- silicone
- adhesive
- acrylic
- tack agent
- graft copolymer
- 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
- 239000000853 adhesive Substances 0.000 claims abstract description 49
- 230000001070 adhesive effect Effects 0.000 claims abstract description 49
- 229920001296 polysiloxane Polymers 0.000 claims abstract description 44
- 229920000578 graft copolymer Polymers 0.000 claims abstract description 24
- 239000000178 monomer Substances 0.000 claims abstract description 14
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229920005601 base polymer Polymers 0.000 claims abstract description 9
- 125000000524 functional group Chemical group 0.000 claims abstract description 7
- 229920000058 polyacrylate Polymers 0.000 claims abstract description 3
- 238000004132 cross linking Methods 0.000 claims description 8
- 239000003522 acrylic cement Substances 0.000 claims description 7
- 239000013464 silicone adhesive Substances 0.000 claims description 7
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 5
- 125000005907 alkyl ester group Chemical group 0.000 claims description 3
- 239000000463 material Substances 0.000 abstract description 7
- 238000010186 staining Methods 0.000 abstract description 6
- 229920001577 copolymer Polymers 0.000 abstract description 5
- 239000003795 chemical substances by application Substances 0.000 abstract 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 239000007787 solid Substances 0.000 description 8
- 239000004820 Pressure-sensitive adhesive Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2,2'-azo-bis-isobutyronitrile Substances N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000011109 contamination Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- -1 phosphate ester Chemical class 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- 239000010935 stainless steel Substances 0.000 description 3
- 230000037303 wrinkles Effects 0.000 description 3
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 2
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 239000012790 adhesive layer Substances 0.000 description 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 2
- 239000003431 cross linking reagent Substances 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- WUDNUHPRLBTKOJ-UHFFFAOYSA-N ethyl isocyanate Chemical compound CCN=C=O WUDNUHPRLBTKOJ-UHFFFAOYSA-N 0.000 description 2
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 2
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- RBQRWNWVPQDTJJ-UHFFFAOYSA-N methacryloyloxyethyl isocyanate Chemical compound CC(=C)C(=O)OCCN=C=O RBQRWNWVPQDTJJ-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 229920001228 polyisocyanate Polymers 0.000 description 2
- 239000005056 polyisocyanate Substances 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 description 1
- 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
- VHSHLMUCYSAUQU-UHFFFAOYSA-N 2-hydroxypropyl methacrylate Chemical compound CC(O)COC(=O)C(C)=C VHSHLMUCYSAUQU-UHFFFAOYSA-N 0.000 description 1
- GWZMWHWAWHPNHN-UHFFFAOYSA-N 2-hydroxypropyl prop-2-enoate Chemical compound CC(O)COC(=O)C=C GWZMWHWAWHPNHN-UHFFFAOYSA-N 0.000 description 1
- DPNXHTDWGGVXID-UHFFFAOYSA-N 2-isocyanatoethyl prop-2-enoate Chemical compound C=CC(=O)OCCN=C=O DPNXHTDWGGVXID-UHFFFAOYSA-N 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
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 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
- 238000007718 adhesive strength test Methods 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 235000013405 beer Nutrition 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 238000012662 bulk polymerization Methods 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 238000010556 emulsion polymerization method Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000000873 masking effect Effects 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 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
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229920005573 silicon-containing polymer Polymers 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000010558 suspension polymerization method Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 235000012431 wafers Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Adhesive Tapes (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
この発明は表面保護材などに好適な非シリコーン系の再
剥離型粘着剤に関する。DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] This invention relates to a non-silicone removable adhesive suitable for surface protection materials and the like.
従来、表面保護材などの粘着剤として、粘着剤中にリン
酸エステル系やアミン系の界面活性剤を配合して被着体
に対する接着力の経日上昇を抑制し、これにより被着体
よりの再剥離を容易としたものが知られている。Conventionally, as adhesives for surface protection materials, phosphate ester-based or amine-based surfactants are blended into the adhesive to suppress the increase in adhesive strength to the adherend over time. There are known products that facilitate re-peeling.
また、上記の界面活性剤を粘着剤中に配合する方式では
その剥離特性がバラツキやすいことなどから、界面活性
剤が粘着剤層の表面を占めることとなるように、支持基
材の背面側に界面活性剤層を設けるようにしたものも知
られている。In addition, in the method of blending the above-mentioned surfactant into the adhesive, its peeling properties tend to vary, so it is necessary to place the surfactant on the back side of the support base so that it occupies the surface of the adhesive layer. Also known are those provided with a surfactant layer.
しかるに、上記従来の方式では、再剥離性に好結果が得
られても、界面活性剤により被着体が汚染されるという
問題点があった。However, in the conventional method described above, even if good results are obtained in terms of removability, there is a problem in that the adherend is contaminated by the surfactant.
そこで、この発明は、再剥離性と非汚染性とに共にすぐ
れた表面保護材などとして好適な粘着剤を提供すること
を目的としている。Therefore, an object of the present invention is to provide an adhesive suitable for use as a surface protection material, etc., which has excellent removability and non-staining properties.
この発明者らは、上記の目的を達成するために鋭意研究
を重ねた結果、粘着剤中に架橋性を有する特定のシリコ
ーン系グラフト共重合体を含有させることにより、再剥
離性と非汚染性とに共にすぐれた再剥離型粘着剤が得ら
れることを見い出し、この発明をなすに至った。As a result of extensive research to achieve the above objectives, the inventors discovered that by incorporating a specific silicone-based graft copolymer with crosslinking properties into the adhesive, removability and non-staining properties were improved. It has been discovered that an excellent removable adhesive can be obtained in combination with the above methods, and the present invention has been completed.
すなわち、この発明は、非シリコーン系粘着剤に、この
粘着剤のベースポリマーと架橋反応しうる官能基を持っ
た架橋性モノマーおよびシリコーンマクロモノマーを必
須成分としたシリコーン系グラフト共重合体を含有させ
たことを特徴とする再剥離型粘着剤に係るものである。That is, the present invention allows a non-silicone adhesive to contain a silicone graft copolymer containing a crosslinkable monomer having a functional group capable of crosslinking with the base polymer of the adhesive and a silicone macromonomer as essential components. The present invention relates to a removable adhesive characterized by:
このように、この発明においては、上記の如き特定のシ
リコーン系グラフト共重合体を用いたことにより、再剥
離性と非汚染性とを共に改善しえたものであるが、これ
はこの共重合体が接着力の上昇に対する抑制効果にすぐ
れる一方、粘着剤から分離しにくいためである、つまり
この共重合体が非シリコーン系の粘着剤より疎外されや
すいために粘着剤層の表面に位置しやすく、一方この共
重合体に含まれる架橋性の官能基が粘着剤を構成するベ
ースポリマーの官能基との間で架橋反応を起こし、粘着
剤との分離が起こらないためである、と考えられる。As described above, in this invention, by using the above-mentioned specific silicone-based graft copolymer, both removability and non-staining property were improved; Although this copolymer has an excellent effect of suppressing increases in adhesive strength, it is difficult to separate from the adhesive; in other words, this copolymer is more easily separated than non-silicone adhesives, and is therefore more likely to be located on the surface of the adhesive layer. On the other hand, this is thought to be because the crosslinkable functional groups contained in this copolymer cause a crosslinking reaction with the functional groups of the base polymer constituting the adhesive, and separation from the adhesive does not occur.
この発明において用いられる非シリコーン系粘着剤とは
、ベースポリマーとして非シリコーン系のポリマーを用
いた粘着剤を意味し、これにはアクリル系粘着剤やゴム
系粘着剤などで代表されるようなシリコーン系粘着剤以
外の粘着剤が広く包含されるものである。The non-silicone adhesive used in this invention means an adhesive that uses a non-silicone polymer as a base polymer, and includes silicone adhesives such as acrylic adhesives and rubber adhesives. It broadly includes adhesives other than type adhesives.
このような粘着剤の中でも、耐候性などの点より、アク
リル酸またはメタクリル酸のアルキルエステルを主モノ
マーとした、つまり通常５０重量％以上使用したアクリ
ル系ポリマーをベースポリマーとして含むアクリル系粘
着剤が、特に好適なものとして挙げられる。Among these adhesives, from the viewpoint of weather resistance, etc., acrylic adhesives containing an acrylic polymer as a base polymer whose main monomer is an alkyl ester of acrylic acid or methacrylic acid, that is, usually 50% by weight or more. , are particularly preferred.
この発明において用いられるシリコーン系グラフト共重
合体は、シリコーンマクロモノマーと架橋性モノマーと
を必須成分として含む単量体混合物を共重合させること
により得られる、重量平均分子量が通常２０．０００〜
５００．０００程度の共重合体である。The silicone-based graft copolymer used in this invention is obtained by copolymerizing a monomer mixture containing a silicone macromonomer and a crosslinkable monomer as essential components, and has a weight average molecular weight of usually 20.000 to 20.000.
It is a copolymer of about 500,000.
シリコーンマクロモノマーとしては、分子鎖中にシロキ
サン結合を有するとともに、その分子鎖末端に重合性不
飽和結合を有する、通常１，０００〜２０．０００程度
の重量平均分子量を有するものが好ましく用いられる。As the silicone macromonomer, one having a siloxane bond in its molecular chain, a polymerizable unsaturated bond at the end of its molecular chain, and usually having a weight average molecular weight of about 1,000 to 20,000 is preferably used.
その代表例としては、下記の一般式で表されるものが挙
げられる。Typical examples include those represented by the following general formula.
Ｃ１）゜
ＣＨｚ ＝ ＣＲ−ＣＯＯ−（ＳｉＯ）−−５ｉ（ＣＨ
ｚ）ｚＨ３
０Ｓｔ （ＣＨ，） ｚ
ＣＨ２＝ＣＲ−Ｃｏｏ Ｃ３１（＆ Ｓｉ ０
５ｉ（ＣＨ３）ｚＯ５ｉ（ＣＨ：＋ｈ
ＣＨ３
ＣＨ！ ＝ ＣＲＣＯ０−ＣＪｈべＳｉＯト、ｌＳｉ
（Ｃｔｈ） ｓ１ｉｓ
ＣＨ２＝ＣＲＣｏｏ Ｃ３１）６Ｓｉ（ＯＸ ）：
１なお、上記の各式中のＲは水素またはメチル基であり
、Ｘはつぎの式；
％式％）：
で表される基である。また、上記の各式中、Ｓｉ原子に
結合するメチル基は、エチル基やフェニル基などであっ
てもよいし、またメトキシ基やエトキシ基などであって
もよく、上記のものに特に限定されない。C1)゜CHz = CR-COO-(SiO)--5i(CH
z)zH3 0St (CH,) z CH2=CR-Coo C31(&Si 0
5i(CH3)zO5i(CH:+h CH3CH!=CRCO0−CJhBeSiO,lSi
(Cth) s1is CH2=CRCoo C31)6Si(OX):
1. In addition, R in each of the above formulas is hydrogen or a methyl group, and X is a group represented by the following formula; Furthermore, in each of the above formulas, the methyl group bonded to the Si atom may be an ethyl group, a phenyl group, or a methoxy group, an ethoxy group, etc., and is not particularly limited to the above. .
一方、架橋性モノマーとしては、粘着剤のベースポリマ
ーに含まれる官能基と反応しうる官能基として、たとえ
ばエポキシ基、イソシアナート基、カルボキシル基、水
酸基、アミド基などを有する七ツマ−が用いられる。そ
の代表例としては、アクリル酸グリシジル、メタクリル
酸グリシジル、アクリル酸２−イソシアナートエチル、
メタクリル酸２−イソシアナートエチル、アクリル酸、
メタクリル酸、イタコン酸、アクリル酸２−ヒドロキシ
エチル、メタクリル酸２−ヒドロキシエチル、アクリル
酸２−ヒドロキシプロピル、メタクリル酸２−ヒドロキ
シプロピル、アクリルアミド、メタクリルアミドなどが
挙げられる。On the other hand, as the crosslinking monomer, a hexamer having a functional group that can react with a functional group contained in the base polymer of the adhesive, such as an epoxy group, an isocyanate group, a carboxyl group, a hydroxyl group, or an amide group, is used. . Representative examples include glycidyl acrylate, glycidyl methacrylate, 2-isocyanatoethyl acrylate,
2-isocyanatoethyl methacrylate, acrylic acid,
Examples include methacrylic acid, itaconic acid, 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl acrylate, 2-hydroxypropyl methacrylate, acrylamide, and methacrylamide.
この発明においては、これらのシリコーンマクロモノマ
ーおよび架橋性モノマーのほかに、これらのモノマーと
共重合可能でかつ架橋反応を阻害しないモノマーを任意
成分として用いることもできる。その具体例としては、
アクリル酸やメタクリル酸のアルキルエステル、スチレ
ンまたはその誘導体、酢酸ビニル、アクリロニトリル、
メタクリロニトリルなどが挙げられる。In this invention, in addition to these silicone macromonomers and crosslinking monomers, monomers that are copolymerizable with these monomers and do not inhibit the crosslinking reaction can also be used as optional components. As a specific example,
Alkyl esters of acrylic acid and methacrylic acid, styrene or its derivatives, vinyl acetate, acrylonitrile,
Examples include methacrylonitrile.
これらの単量体混合物における各七ツマ−の割合として
は、全七ツマー中、シリコーンマクロモノマーが通常１
〜５０重量％、好適には５〜３０重量％、架橋性七ツマ
−が通常０．５〜５０重量％、好適には２〜２０重量％
、任意成分としての前記共重合可能なモノマーが通常０
〜９０重量％、好適には３０〜８０重量％となるように
するのがよい。As for the proportion of each heptamer in these monomer mixtures, silicone macromonomer usually accounts for 1 out of all heptamers.
~50% by weight, preferably 5 to 30% by weight, and crosslinkable nitrate usually 0.5 to 50% by weight, preferably 2 to 20% by weight
, the copolymerizable monomer as an optional component is usually 0
It is preferable to adjust the amount to 90% by weight, preferably 30 to 80% by weight.
このような単量体混合物を用いた共重合は、たとえば公
知の溶液重合方式、エマルジョン重合方式、懸濁重合方
式、バルク重合方式などにより行うことができる。これ
らの中でも、溶液重合方式が簡便性の点より特に好まし
い。Copolymerization using such a monomer mixture can be carried out, for example, by a known solution polymerization method, emulsion polymerization method, suspension polymerization method, bulk polymerization method, or the like. Among these, the solution polymerization method is particularly preferred from the viewpoint of simplicity.
この発明においては、このようにして得られるシリコー
ン系グラフト共重合体を前記した非シリコーン系粘着剤
に含有させることにより、再剥離性および非汚染性にす
ぐれる再剥離型粘着剤を調製する。ここで、シリコーン
系グラフト共重合体の含有量は、粘着剤（の固形分）中
のシリコーンマクロ七ツマー単位が０．０５〜２０重量
％となるような割合が適当であり、特に００１〜１０重
量％となるような割合が好ましい。この含有量が過少で
は満足できる再剥離性が得られず、過多となると支持基
材などに対する密着性に乏しくなり、また被着体に対す
る汚染が起こりやすくなる。In the present invention, a removable adhesive having excellent removability and non-staining property is prepared by incorporating the thus obtained silicone graft copolymer into the above-mentioned non-silicone adhesive. Here, the content of the silicone-based graft copolymer is suitably such that the silicone macro-7mer units in the adhesive (solid content) are 0.05 to 20% by weight, particularly 001 to 10% by weight. Preferably, the ratio is % by weight. If the content is too small, satisfactory removability cannot be obtained, and if the content is too large, adhesion to supporting substrates etc. will be poor and contamination of adherends will likely occur.
この発明の再剥離型粘着剤は、加工中や運搬中などでの
傷付防止を目的とする表面保護材やマスキング材などの
ように、被着体に一旦貼着したのち再剥離する必要のあ
る用途に好ましく使用されるが、その際、紙糸、布糸、
プラスチック糸、金属箔系などの適宜の支持基材に付設
した状態で用いるのが一般的である。The removable adhesive of this invention can be used as a surface protection material or masking material for the purpose of preventing scratches during processing or transportation, etc. Once it has been applied to an adherend, it does not need to be peeled off again. It is preferably used for certain purposes, and in that case, paper thread, cloth thread,
It is generally used attached to an appropriate support base material such as plastic thread or metal foil.
貼着の対象である被着体としては、金属板、プラスチッ
ク板、ガラス板、シリコン板、半導体ウェハなどが挙げ
られる。また、被着体への粘着剤の貼着は、ロール圧着
方式などの通常方式で容易に行うことができる。Examples of adherends to be adhered include metal plates, plastic plates, glass plates, silicon plates, and semiconductor wafers. Further, the adhesive can be easily attached to the adherend by a normal method such as a roll pressure bonding method.
この発明の再剥離型粘着剤は、シリコーン系グラフト共
重合体を含有するので再剥離性にすぐれている。また、
そのシリコーン系グラフト共重合体は粘着剤と架橋反応
により結合しているため、粘着剤との分離がおこらず、
これにより被着体に対する非汚染性にもすぐれている。The removable pressure-sensitive adhesive of the present invention has excellent removability because it contains a silicone-based graft copolymer. Also,
The silicone-based graft copolymer is bonded to the adhesive through a crosslinking reaction, so it does not separate from the adhesive.
This also provides excellent non-contamination properties for adherends.
つぎに、この発明の実施例を記載してより具体的に説明
する。なお、以下部とあるのは重量部を意味し、またア
クリル系粘着剤（１）、 （ＩＩ）とシリコーン系グ
ラフト共重合体（Ｉ）〜（ＩＩＩ）は、下記の方法で調
製したものである。Next, examples of the present invention will be described in more detail. The following parts mean parts by weight, and the acrylic adhesives (1) and (II) and silicone graft copolymers (I) to (III) were prepared by the following method. be.
〈アクリル系粘着剤（Ｉ）〉
アクリル酸ブチル８０部とアクリル酸エチル１５部とア
クリル酸２−ヒドロキシエチル５部とを、トルエン中で
過酸化ベンゾイル０．４部の存在下に、７０℃で１２時
間重合処理して、アクリル系粘着剤（１）のトルエン溶
液を得た。<Acrylic adhesive (I)> 80 parts of butyl acrylate, 15 parts of ethyl acrylate, and 5 parts of 2-hydroxyethyl acrylate were mixed in toluene at 70°C in the presence of 0.4 part of benzoyl peroxide. The polymerization treatment was carried out for 12 hours to obtain a toluene solution of the acrylic pressure-sensitive adhesive (1).
くアクリル系粘着剤（■）〉
アクリル酸２−エチルヘキシル７０部とメタクリル酸ブ
チル２８部とアクリル酸２部とを、酢酸エチル中で２・
２′−アゾビスイソブチロニトリル０．５部の存在下に
、７０°Ｃで１６時間重合処理して、アクリル系粘着剤
（ｎ）の酢酸エチル溶液を得た。Acrylic adhesive (■)> 70 parts of 2-ethylhexyl acrylate, 28 parts of butyl methacrylate, and 2 parts of acrylic acid were mixed in ethyl acetate with 2.
Polymerization was carried out at 70°C for 16 hours in the presence of 0.5 part of 2'-azobisisobutyronitrile to obtain an ethyl acetate solution of the acrylic adhesive (n).
くシリコーン系グラフト共重合体（Ｉ）〉ＣＨｚ
ＣＨ３
ＣＨｚ ＝ ＣＣＯＯ（Ｓｉ Ｏト、 ５ｔ（Ｃ１ｈ）
□Ｈ３
で表されるシリコーンマクロモノマ−（式中のｎ＃７０
）２０部とアクリル酸ブチル６０部とメタクリル酸２−
イソシアナートエチル２０部とを、トルエン中で２・２
′−アゾビスイソブチロニトリル０．６部の存在下に７
０°Ｃで１２時間反応させて、重量平均分子量１２万の
シリコーン系グラフト共重合体（１）のトルエン溶液を
得た。Silicone-based graft copolymer (I)〉CHz
CH3 CHz = CCOO(SiO, 5t(C1h)
□Silicone macromonomer represented by H3 (n#70 in the formula
), 60 parts of butyl acrylate, and 2-methacrylic acid.
20 parts of ethyl isocyanate and 2.2 parts of ethyl isocyanate in toluene.
7 in the presence of 0.6 parts of '-azobisisobutyronitrile.
The reaction was carried out at 0°C for 12 hours to obtain a toluene solution of silicone graft copolymer (1) having a weight average molecular weight of 120,000.
〈シリコーン系グラフト共重合体（■）〉で表されるシ
リコーンマクロモノマー（式中のｎ＝３０）２０部とア
クリル酸２−エチルへキシル６０部とメタクリル酸グリ
シジル２０部とを、トルエン中で２・２′−アゾビスイ
ソブチロニトリル０．８部の存在下に７０℃で１０時間
反応させて、重量平均分子量１５万のシリコーン系グラ
フト共重合体（ｎ）のトルエン溶液を得た。20 parts of a silicone macromonomer (n=30 in the formula) represented by <Silicone-based graft copolymer (■)>, 60 parts of 2-ethylhexyl acrylate, and 20 parts of glycidyl methacrylate were mixed in toluene. A reaction was carried out at 70°C for 10 hours in the presence of 0.8 part of 2,2'-azobisisobutyronitrile to obtain a toluene solution of silicone graft copolymer (n) having a weight average molecular weight of 150,000.
〈シリコーン系グラフト共重合体（■）〉メタクリル酸
２−イソシアナートエチル２０部の代わりにメタクリル
酸ブチルを２０部用いた以外は、シリコーン系グラフト
共重合体（１）の場合と同様に重合処理して、重量平均
分子量ｌＯ万のシリコーン系グラフト共重合体（ＩＩＩ
）のトルエン溶液を得た。<Silicone-based graft copolymer (■)> Polymerization treatment was carried out in the same manner as in the case of silicone-based graft copolymer (1), except that 20 parts of butyl methacrylate was used instead of 20 parts of 2-isocyanatoethyl methacrylate. A silicone-based graft copolymer (III) having a weight average molecular weight of 10,000
) was obtained.
実施例１
アクリル系粘着剤（Ｉ）のトルエン溶液とシリコーン系
グラフト共重合体（１）のトルエン溶液とを、前者対後
者の固形分重量比が８０：２０となるように混合して、
粘着剤溶液を得た。なお、粘着剤中のシリコーンマクロ
モノマーの含有率は計算値で４．０重量％であった。Example 1 A toluene solution of the acrylic pressure-sensitive adhesive (I) and a toluene solution of the silicone-based graft copolymer (1) were mixed such that the solid content weight ratio of the former to the latter was 80:20,
An adhesive solution was obtained. The calculated content of silicone macromonomer in the adhesive was 4.0% by weight.
実施例２
アクリル系粘着剤（ｎ）の酢酸エチル溶液とシリコーン
系グラフト共重合体（ｎ）のトルエン溶液とを、前者対
後者の固形分重量比が９０：１０となるように混合し、
この混合物の固形分１００部に対してさらにトリエチル
アミン０．５部を混合して、粘着剤？８液を得た。なお
、粘着剤中のシリコーンマクロモノマーの含有率は計算
値で１．０重量％であった。Example 2 An ethyl acetate solution of an acrylic adhesive (n) and a toluene solution of a silicone graft copolymer (n) were mixed such that the solid content weight ratio of the former to the latter was 90:10,
Add 0.5 parts of triethylamine to 100 parts of the solid content of this mixture to form an adhesive. Eight liquids were obtained. The calculated content of silicone macromonomer in the adhesive was 1.0% by weight.
実施例３
アクリル系粘着剤（Ｉ）のトルエン溶液とシリコーン系
グラフト共重合体（１）のトルエン溶液とを、前者対後
者の固形分重量比が６５＝３５となるように混合して、
粘着剤溶液を得た。なお、粘着剤中のシリコーンマクロ
モノマーの含有率は計算値で７．０重量％であった。Example 3 A toluene solution of the acrylic pressure-sensitive adhesive (I) and a toluene solution of the silicone-based graft copolymer (1) were mixed such that the solid content weight ratio of the former to the latter was 65=35,
An adhesive solution was obtained. The calculated content of silicone macromonomer in the adhesive was 7.0% by weight.
比較例１
アクリル系粘着剤（１）のトルエン溶液とシリコーン系
グラフト共重合体（ＩＩＩ）のトルエン溶液とを、前者
対後者の固形分重量比が７８：２０となるように混合し
、この混合物の固形分９８部に対してさらにポリイソシ
アネート系架橋剤２部を混合して、粘着剤溶液を得た。Comparative Example 1 A toluene solution of the acrylic adhesive (1) and a toluene solution of the silicone graft copolymer (III) were mixed such that the solid content weight ratio of the former to the latter was 78:20, and this mixture An adhesive solution was obtained by further mixing 2 parts of a polyisocyanate crosslinking agent with 98 parts of the solid content.
なお、シリコーンマクロモノマーの含有率は計算値で４
．０重量％であった。The content of silicone macromonomer is calculated as 4.
．． It was 0% by weight.
比較例２
アクリル系粘着剤（１）のトルエン溶液に、その固型分
９８部に対して２部となる割合のポリイソシアネート系
架橋剤を混合して、粘着剤溶液を得た。Comparative Example 2 A toluene solution of the acrylic adhesive (1) was mixed with a polyisocyanate crosslinking agent in an amount of 2 parts based on 98 parts of the solid content to obtain an adhesive solution.
以上の実施例１〜３および比較例１．２で得た各粘着剤
溶液を、表面をコロナ処理した厚さ６０μｍのポリエチ
レンフィルムに塗布し、加熱乾燥処理して、厚さ１０μ
ｍの粘着剤層を有する表面保護シートを得、以下の試験
に供した。試験結果は、後記の表に示されるとおりであ
った。Each of the adhesive solutions obtained in Examples 1 to 3 and Comparative Example 1.2 above was applied to a 60 μm thick polyethylene film whose surface had been corona treated, and heated and dried to form a 10 μm thick polyethylene film.
A surface protection sheet having a pressure-sensitive adhesive layer of m was obtained and subjected to the following tests. The test results were as shown in the table below.
く初期接着力〉
表面保護シートを厚さ０．４ ｍのステンレス板（Ｓｔ
ｌＳ ３０４ ＢＡ仕上げ）に２３℃下で貼着し、３０
分後の接着力（１８０度ビール、引張速度３００ｆｌ／
分）を測定した。Initial adhesive strength〉 The surface protection sheet was attached to a 0.4 m thick stainless steel plate (St
IS 304 BA finish) at 23℃,
Adhesive strength after minutes (180 degree beer, tensile speed 300fl/
minutes) was measured.
〈接着力上昇性〉
初期接着力の試験に準じ、表面保護シートをステンレス
板に貼着したのち５０℃下に７日間放置し、２３℃に冷
却後その接着力を測定した。<Increasing Adhesion Strength> According to the initial adhesive strength test, the surface protection sheet was attached to a stainless steel plate and then left at 50°C for 7 days, and after cooling to 23°C, the adhesive strength was measured.
く非汚染性〉
表面保護シートをガラス板に貼着し、５０℃下に２４時
間放置後取り出して表面保護シートを引き剥がし、第１
図の如くそのガラス板ｌの剥がし面に水滴２を落として
接触角計によりその角度（θ）を測定し、接触角が１０
度以下の場合を０１）１度以上の場合を×として評価し
た。Non-contaminating> Attach the surface protection sheet to a glass plate, leave it at 50℃ for 24 hours, then take it out and peel off the surface protection sheet.
As shown in the figure, a water droplet 2 is dropped on the peeled surface of the glass plate 1, and its angle (θ) is measured using a contact angle meter, and the contact angle is 10.
The evaluation was rated as 01 when the temperature was less than 1 degree, and × when it was 1 degree or more.
〈加工性〉
初期接着力の試験に準じ、表面保護シートを貼着したス
テンレス板４を、第２図の如きポンチ３と金型５を用い
て絞り加工した際に、加工後の表面保護シートにシワ、
破れ、浮きなどの問題がなく、良好な貼着状態を維持し
ている場合を○、シワ、破れ、浮きなどが部分的に発生
している場合を△、シワや彼れが著しかったり、全面が
浮いている場合を×として評価した。<Workability> According to the initial adhesion test, when the stainless steel plate 4 with the surface protection sheet pasted was drawn using the punch 3 and die 5 as shown in Fig. 2, the surface protection sheet after processing was wrinkles,
○: If there are no problems such as tears or lifting, and the adhesion remains in good condition, △: If wrinkles, tears, lifting, etc. have occurred partially, △: If there are severe wrinkles or peeling, A case where the mark was floating was evaluated as ×.
上記表の結果から明らかなように、この発明の再剥離型
粘着剤は、接着力の変化が少なくて再剥離性にすぐれる
うえに、非汚染性にもすぐれており、しかも良好な加工
性をも備えていることが判る。As is clear from the results in the table above, the removable adhesive of the present invention has excellent removability with little change in adhesive strength, excellent non-staining properties, and good processability. It turns out that it also has the following.
第１図は非汚染性の試験における接触角を測定する方法
を示す説明図、第２図は加工性の試験方法を示す説明図
である。
特許出願人 日東電工株式会社FIG. 1 is an explanatory diagram showing a method for measuring a contact angle in a non-contamination test, and FIG. 2 is an explanatory diagram showing a processability test method. Patent applicant Nitto Denko Corporation
Claims (3)
リマーと架橋反応しうる官能基を持つた架橋性モノマー
およびシリコーンマクロモノマーを必須成分としたシリ
コーン系グラフト共重合体を含有させたことを特徴とす
る再剥離型粘着剤。(1) A non-silicone adhesive contains a silicone graft copolymer containing a crosslinkable monomer having a functional group capable of crosslinking with the base polymer of the adhesive and a silicone macromonomer as essential components. Features a removable adhesive.
剤中のシリコーンマクロモノマー単位で０．０５〜２０
重量％となる割合とされた請求項（１）に記載の再剥離
型粘着剤。(2) The content of the silicone-based graft copolymer is 0.05 to 20 in silicone macromonomer units in the adhesive.
The removable adhesive according to claim 1, wherein the proportion is expressed as % by weight.
クリル酸のアルキルエステルを主モノマーとするアクリ
ル系ポリマーをベースポリマーとして含むアクリル系粘
着剤である請求項（１）または（２）に記載の再剥離型
粘着剤。(3) The non-silicone adhesive is an acrylic adhesive containing as a base polymer an acrylic polymer whose main monomer is an alkyl ester of acrylic acid or methacrylic acid. Peelable adhesive.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63276892A JP2582875B2 (en) | 1988-11-01 | 1988-11-01 | Removable adhesive |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63276892A JP2582875B2 (en) | 1988-11-01 | 1988-11-01 | Removable adhesive |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02123182A true JPH02123182A (en) | 1990-05-10 |
| JP2582875B2 JP2582875B2 (en) | 1997-02-19 |
Family
ID=17575851
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63276892A Expired - Lifetime JP2582875B2 (en) | 1988-11-01 | 1988-11-01 | Removable adhesive |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2582875B2 (en) |
Cited By (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH04117475A (en) * | 1990-09-07 | 1992-04-17 | Toyo Ink Mfg Co Ltd | Re-releasable pressure sensitive adhesive composition |
| JPH11100509A (en) * | 1997-09-29 | 1999-04-13 | Toyo Ink Mfg Co Ltd | Releasant and release liner therewith |
| JP2004211004A (en) * | 2003-01-07 | 2004-07-29 | Ricoh Co Ltd | Heat-sensitive adhesive material |
| JP2008063551A (en) * | 2005-12-13 | 2008-03-21 | Toray Ind Inc | Adhesive composition for electronic device, adhesive sheet for electronic device, and electronic component and device using the same |
| WO2009050785A1 (en) * | 2007-10-16 | 2009-04-23 | Denki Kagaku Kogyo Kabushiki Kaisha | Pressure-sensitive adhesive, pressure-sensitive adhesive sheet, multilayered pressure-sensitive adhesive sheet, and process for producing electronic part |
| JP2014037502A (en) * | 2012-08-20 | 2014-02-27 | Shin Etsu Chem Co Ltd | Optical pressure-sensitive adhesive composition |
| JP2014105325A (en) * | 2012-11-30 | 2014-06-09 | Toyo Kagaku Kk | Composite film for coating material used by coating on objects receiving bending deformation |
| WO2014171075A1 (en) * | 2013-04-15 | 2014-10-23 | 日東電工株式会社 | Adhesive composition, adhesive layer, and adhesive sheet |
| JP2016018008A (en) * | 2014-07-04 | 2016-02-01 | 旭化成イーマテリアルズ株式会社 | Pellicle, pellicle-fitted photomask and method for producing semiconductor device |
| JP2016531167A (en) * | 2013-11-21 | 2016-10-06 | エルジー・ケム・リミテッド | Protective film |
| CN106062928A (en) * | 2014-03-03 | 2016-10-26 | 琳得科株式会社 | Sheet for semiconductor-related-member processing and process for producing chip using said sheet |
| US20170043566A1 (en) * | 2014-04-22 | 2017-02-16 | Nitto Denko Corporation | Pressure-sensitive adhesive sheet |
| JP2017203164A (en) * | 2013-04-15 | 2017-11-16 | 日東電工株式会社 | Adhesive composition, adhesive layer and adhesive sheet |
| WO2019235487A1 (en) * | 2018-06-05 | 2019-12-12 | 積水化学工業株式会社 | Pressure-sensitive adhesive tape |
| CN111748302A (en) * | 2020-05-15 | 2020-10-09 | 明基材料有限公司 | (meth) acrylate adhesive composition |
| US10894904B2 (en) | 2013-04-15 | 2021-01-19 | Nitto Denko Corporation | Pressure-sensitive adhesive sheet and pressure sensitive adhesive composition |
| JPWO2019235287A1 (en) * | 2018-06-06 | 2021-05-06 | 積水化学工業株式会社 | Adhesive tape |
| CN113260689A (en) * | 2019-03-08 | 2021-08-13 | 积水化学工业株式会社 | Adhesive composition and adhesive tape |
| CN113913135A (en) * | 2021-10-26 | 2022-01-11 | 明基材料有限公司 | (meth) acrylate adhesive composition |
| US11781046B2 (en) | 2021-10-18 | 2023-10-10 | Benq Materials Corporation | (Meth)acrylate adhesive composition |
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Cited By (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH04117475A (en) * | 1990-09-07 | 1992-04-17 | Toyo Ink Mfg Co Ltd | Re-releasable pressure sensitive adhesive composition |
| JPH11100509A (en) * | 1997-09-29 | 1999-04-13 | Toyo Ink Mfg Co Ltd | Releasant and release liner therewith |
| JP2004211004A (en) * | 2003-01-07 | 2004-07-29 | Ricoh Co Ltd | Heat-sensitive adhesive material |
| JP2008063551A (en) * | 2005-12-13 | 2008-03-21 | Toray Ind Inc | Adhesive composition for electronic device, adhesive sheet for electronic device, and electronic component and device using the same |
| WO2009050785A1 (en) * | 2007-10-16 | 2009-04-23 | Denki Kagaku Kogyo Kabushiki Kaisha | Pressure-sensitive adhesive, pressure-sensitive adhesive sheet, multilayered pressure-sensitive adhesive sheet, and process for producing electronic part |
| US20100248452A1 (en) * | 2007-10-16 | 2010-09-30 | Denki Kagaku Kogyo Kabushiki Kaisha | Adhesive, adhesive sheet, multi-layered adhesive sheet, and production method for electronic part |
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| Publication number | Publication date |
|---|---|
| JP2582875B2 (en) | 1997-02-19 |
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