JP2520145B2 - Ultraviolet-crosslinkable hot melt adhesive composition - Google Patents
Ultraviolet-crosslinkable hot melt adhesive compositionInfo
- Publication number
- JP2520145B2 JP2520145B2 JP62301679A JP30167987A JP2520145B2 JP 2520145 B2 JP2520145 B2 JP 2520145B2 JP 62301679 A JP62301679 A JP 62301679A JP 30167987 A JP30167987 A JP 30167987A JP 2520145 B2 JP2520145 B2 JP 2520145B2
- Authority
- JP
- Japan
- Prior art keywords
- melt adhesive
- crosslinkable
- base component
- acrylate
- hot
- 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 - Fee Related
Links
- 239000004831 Hot glue Substances 0.000 title claims description 26
- 229920005989 resin Polymers 0.000 claims description 15
- 239000011347 resin Substances 0.000 claims description 15
- -1 ester acrylate Chemical class 0.000 claims description 11
- 239000005062 Polybutadiene Substances 0.000 claims description 9
- 229920002857 polybutadiene Polymers 0.000 claims description 9
- 239000003999 initiator Substances 0.000 claims description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 7
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 6
- 229920002367 Polyisobutene Polymers 0.000 claims description 5
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 claims description 5
- 229920001195 polyisoprene Polymers 0.000 claims description 5
- 229920002725 thermoplastic elastomer Polymers 0.000 claims description 5
- 229920001083 polybutene Polymers 0.000 claims description 4
- 239000013032 Hydrocarbon resin Substances 0.000 claims description 3
- 239000004902 Softening Agent Substances 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 238000004132 cross linking Methods 0.000 claims description 3
- 229920006270 hydrocarbon resin Polymers 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 claims description 3
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 239000000853 adhesive Substances 0.000 description 11
- 230000001070 adhesive effect Effects 0.000 description 11
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 3
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- 238000013329 compounding Methods 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 230000001678 irradiating effect Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 229920000098 polyolefin Polymers 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 238000012719 thermal polymerization Methods 0.000 description 2
- KEOLYBMGRQYQTN-UHFFFAOYSA-N (4-bromophenyl)-phenylmethanone Chemical compound C1=CC(Br)=CC=C1C(=O)C1=CC=CC=C1 KEOLYBMGRQYQTN-UHFFFAOYSA-N 0.000 description 1
- SWFHGTMLYIBPPA-UHFFFAOYSA-N (4-methoxyphenyl)-phenylmethanone Chemical compound C1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1 SWFHGTMLYIBPPA-UHFFFAOYSA-N 0.000 description 1
- MSAHTMIQULFMRG-UHFFFAOYSA-N 1,2-diphenyl-2-propan-2-yloxyethanone Chemical compound C=1C=CC=CC=1C(OC(C)C)C(=O)C1=CC=CC=C1 MSAHTMIQULFMRG-UHFFFAOYSA-N 0.000 description 1
- DKEGCUDAFWNSSO-UHFFFAOYSA-N 1,8-dibromooctane Chemical compound BrCCCCCCCCBr DKEGCUDAFWNSSO-UHFFFAOYSA-N 0.000 description 1
- CERJZAHSUZVMCH-UHFFFAOYSA-N 2,2-dichloro-1-phenylethanone Chemical compound ClC(Cl)C(=O)C1=CC=CC=C1 CERJZAHSUZVMCH-UHFFFAOYSA-N 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
- ZCDADJXRUCOCJE-UHFFFAOYSA-N 2-chlorothioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3SC2=C1 ZCDADJXRUCOCJE-UHFFFAOYSA-N 0.000 description 1
- NLGDWWCZQDIASO-UHFFFAOYSA-N 2-hydroxy-1-(7-oxabicyclo[4.1.0]hepta-1,3,5-trien-2-yl)-2-phenylethanone Chemical compound OC(C(=O)c1cccc2Oc12)c1ccccc1 NLGDWWCZQDIASO-UHFFFAOYSA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 1
- 241000705989 Tetrax Species 0.000 description 1
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 229920005549 butyl rubber Polymers 0.000 description 1
- VZWXIQHBIQLMPN-UHFFFAOYSA-N chromane Chemical compound C1=CC=C2CCCOC2=C1 VZWXIQHBIQLMPN-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 238000001723 curing Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 229920006332 epoxy adhesive Polymers 0.000 description 1
- 230000003628 erosive effect Effects 0.000 description 1
- 239000005038 ethylene vinyl acetate Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 238000000016 photochemical curing Methods 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000012985 polymerization agent Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000010734 process oil Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Polymerisation Methods In General (AREA)
- Adhesives Or Adhesive Processes (AREA)
Description
【発明の詳細な説明】 産業上の利用分野 本発明は紫外線架橋性ホツトメルト型接着剤組成物、
更に詳しくは、ホツトメルト型接着剤に特定の紫外線架
橋性樹脂オリゴマーおよび光重合開始剤を配合し、これ
を紫外線照射（UV照射）で架橋せしめ、特に該組成物の
塗布時の熱安定性を向上せしめたものに関する。TECHNICAL FIELD The present invention relates to a UV-crosslinkable hot melt adhesive composition,
More specifically, a hot-melt adhesive is blended with a specific UV-crosslinkable resin oligomer and a photopolymerization initiator, and this is crosslinked by UV irradiation (UV irradiation) to improve the thermal stability particularly when the composition is applied. It's about the stuff.
従来技術と発明の解決すべき問題点 ホツトメルト型接着剤（以下、HMAと略す）は、無溶
剤型で速硬化性を有することから、各種の分野で広く使
用されている。例えば、光デイスクの製造分野において
は、その使いよさなどの利点から、従来のエポキシ系接
着剤や溶剤型接着剤に代わるものとして注目されてい
る。BACKGROUND ART Problems to be Solved by the Invention and Invention The hot melt adhesive (hereinafter abbreviated as HMA) is widely used in various fields because it is solvent-free and has fast curing property. For example, in the field of optical disc manufacturing, it has been attracting attention as an alternative to conventional epoxy adhesives and solvent-based adhesives because of its advantages such as ease of use.
たとえば、ブロツク状熱可塑性エラストマー、粘着付
与剤および軟化剤から成り、軟化点や溶融粘度を規制し
たHMAが知られている（特開昭58−108044号公報参
照）。しかしながら、その適用に際しデイスクに損傷を
与えないためにはなるべく低温、低粘度での塗布が望ま
れるが、それでは耐熱性に限界がある。このようにHMA
の欠点として耐熱性の不足が挙げられ、特に塗布性能の
耐熱性のバランスをとるのが困難なため、接着剤の使用
範囲が制限される。For example, an HMA comprising a block-like thermoplastic elastomer, a tackifier and a softening agent and having a controlled softening point and melt viscosity is known (see JP-A-58-108044). However, in order to prevent damage to the disk during its application, it is desirable to apply at a low temperature and a low viscosity, but this has a limit in heat resistance. HMA like this
Insufficient heat resistance is mentioned as a drawback of the above method, and since it is difficult to balance the heat resistance of the coating performance, the range of use of the adhesive is limited.
一方、このような状況下で、HMAに放射線硬化性化合
物（アクリレートモノマーど）を配合し、これを放射線
照射で硬化せしめ耐熱性を向上させる試みがなされてい
る（特開昭47−1086号公報、西独特許公開第2350030号
公報参照）。しか、アクリレートモノマーは配合時ある
いは塗布作業時の加熱によつて容易に熱重合を起し、HM
Aの増粘、ゲル化が頻繁に起る。このため、混練から塗
工までのプロセスを一連の作業で単時間のうちにすまさ
なければならない（「接着」29巻６号（1985年）、36〜
37頁参照）。On the other hand, under such circumstances, an attempt has been made to blend HMA with a radiation-curable compound (such as an acrylate monomer) and cure it by irradiation with radiation to improve heat resistance (JP-A-47-1086). , West German Patent Publication No. 2350030). However, the acrylate monomer easily undergoes thermal polymerization due to heating during compounding or coating work, and HM
Thickening and gelation of A frequently occur. For this reason, the process from kneading to coating must be completed in a single time in a series of operations ("Adhesion" Vol. 29 No. 6 (1985), 36-
(See page 37).
そこで本発明者らは、かかる光硬化による耐熱性の向
上および接着作業時の熱安定性化を両立させるべく鋭意
検討を進めたところ、HMAに特定の紫外線架橋性樹脂オ
リゴマーおよび光重合開始剤を配合し、これをUV照射す
れば、所期目的が達成されることを見出し、本発明を完
成させるに至つた。Therefore, the present inventors have conducted intensive studies to improve the heat resistance due to such photo-curing and the heat stabilization during the bonding work, and a specific UV-crosslinkable resin oligomer and a photopolymerization initiator are added to HMA. It was found that the intended purpose can be achieved by compounding and irradiating with UV, and the present invention has been completed.
発明の構成と効果 すなわち、本発明は、HMAベース成分、紫外線架橋性
成分として１分子中に少なくとも１個のアクリロイル基
を含有する飽和炭化水素系樹脂オリゴマー、および光重
合開始剤から成り、上記HMAベース成分が、ブロック状
熱可塑性エラストマー、粘着付与剤および軟化剤からな
り、上記紫外線架橋性樹脂オリゴマーが、１分子中に少
なくとも１個の水酸基もしくはカルボキシ基を含有する
水添ポリブタジエン、ポリブテン、水添ポリイソプレン
またはポリイソブチレンオリゴマーのアクリレート、ウ
レタンアクリレート、エポキシアクリレートまたはエス
テルアクリレートであり、かつ上記紫外線架橋性樹脂オ
リゴマーの使用量がHMAベース成分100重量部に対して５
〜100重量部、および上記光重合開始剤の使用量がHMAベ
ース成分と紫外線架橋性樹脂オリゴマーの合計量に対し
て0.5〜５重量％であることを特徴とする紫外線架橋性
ホツトメルト型接着剤組成物を提供するものである。That is, the present invention comprises an HMA base component, a saturated hydrocarbon resin oligomer containing at least one acryloyl group in one molecule as a UV-crosslinkable component, and a photopolymerization initiator. The base component comprises a block-shaped thermoplastic elastomer, a tackifier and a softening agent, and the above-mentioned UV-crosslinkable resin oligomer contains at least one hydroxyl group or carboxy group in one molecule. Hydrogenated polybutadiene, polybutene, hydrogenated It is an acrylate, urethane acrylate, epoxy acrylate or ester acrylate of polyisoprene or polyisobutylene oligomer, and the amount of the above UV-crosslinkable resin oligomer used is 5 per 100 parts by weight of the HMA base component.
To 100 parts by weight, and the amount of the photopolymerization initiator used is 0.5 to 5% by weight, based on the total amount of the HMA base component and the ultraviolet-crosslinkable resin oligomer, an ultraviolet-crosslinkable hot melt adhesive composition. It is to provide things.
本発明で用いるHMAベース成分としては、常温で粘着
性を有するものであつて、式： Ａ−Ｂ、Ａ−Ｂ−ＡまたはＢ−Ａ−Ｂ 〔式中、Ａは分子量2000〜12500のポリスチレンブロツ
ク、およびＢは分子量1000〜250000のポリブタジエンブ
ロツク、ポリイソプレンブロツクまたはエチレンブチレ
ン共重合体ブロツクである〕 で示されるブロツク状熱可塑性エラストマーの１種また
は２種以上、またはこれに要すれば合成ゴム（ポリイソ
プレン、スチレンゴム、ブタジエンゴム、ブチルゴムな
ど）、ポリオレフインもしくはポリオレフイン系共重合
体（ポリエチレン、ポリプロピレン、エチレン−ビニル
アセテート共重合体など）を配合し、更に粘着付与剤
（ロジン樹脂、水添石油樹脂、水添テルペン樹脂、フエ
ノール樹脂、クロマン樹脂など）、軟化剤（プロセス
油、パラフイン油、ポリブテン、ポリイソブチレンな
ど）を適量加えたものである。水添タイプの粘着付与剤
は、相溶性が良く、熱安定性に悪影響を及ぼさず、また
吸水率が低いので良好な耐食性をもたらす。The HMA base component used in the present invention has adhesiveness at room temperature and has the formula: AB, ABA or BAB, where A is a polystyrene having a molecular weight of 2000-12500. And B is a polybutadiene block, a polyisoprene block or an ethylene butylene copolymer block having a molecular weight of 1000 to 250,000], one or more of the block-like thermoplastic elastomers, or a synthetic rubber if required. (Polyisoprene, styrene rubber, butadiene rubber, butyl rubber, etc.), polyolefin or polyolefin copolymers (polyethylene, polypropylene, ethylene-vinyl acetate copolymer, etc.) are added, and a tackifier (rosin resin, hydrogenated petroleum) Resin, hydrogenated terpene resin, phenol resin, chroman resin, etc.), softener ( Process oil, paraffin oil, polybutene, polyisobutylene, etc.) are added in appropriate amounts. The hydrogenation type tackifier has good compatibility, does not adversely affect the thermal stability, and has a low water absorption rate, and thus provides good corrosion resistance.
本発明で用いる紫外線架橋性成分である１分子中に少
なくとも１個のアクロイル基を含有する飽和炭化水素系
樹脂オリゴマー（紫外線架橋性樹脂オリゴマー）とは、
１分子中に少なくとも１個の水酸基もしくはカルボキシ
ル基を含有する水添ポリブタジエン、ポリブテン、水添
ポリイソプレンまたはポリイソブチレンオリゴマーのア
クリレート、ウレタンアクリレート、エポキシアクリレ
ートまたはエステルアクリレートを指称し、これらの１
種または２種以上を使用に供する。使用量は通常、HMA
ベース成分100部（重量部、以下同様）に対して５〜100
部、好ましくは10〜40部の範囲で選定すればよい。５部
未満であると、紫外線照射による耐熱性向上の効果が低
く、また100部を越えると、粘着性が低下する傾向にあ
る。The saturated hydrocarbon resin oligomer (ultraviolet crosslinking resin oligomer) containing at least one acroyl group in one molecule which is the ultraviolet crosslinking component used in the present invention is
An acrylate, urethane acrylate, epoxy acrylate or ester acrylate of hydrogenated polybutadiene, polybutene, hydrogenated polyisoprene or polyisobutylene oligomer containing at least one hydroxyl group or carboxyl group in one molecule is designated, and these 1
Use one or two or more species. HMA is usually used
5 to 100 for 100 parts of base component (weight part, the same below)
Parts, preferably 10 to 40 parts. If it is less than 5 parts, the effect of improving the heat resistance by ultraviolet irradiation is low, and if it exceeds 100 parts, the tackiness tends to decrease.
本発明で用いる光重合開始剤としては、UV照射により
ラジカルを発生する通常の、たとえばベンゾインエーテ
ル系（ベンゾインイソプロピルエーテル、ベンゾインイ
ソブチルエーテルなど）、ベンゾフエノン系（ベンゾフ
エノン、ｐ−メトキシベンゾフエノン、ｐ−ブロモベン
ゾフエノンなど）、アセトフエノン系（ベンジルメチル
ケタール、2,2−ジエトキシアセトフエノン、1,1−ジク
ロロアセトフエノンなど）、チオキサントン系（２−ク
ロロチオキサントンなで）が挙げられる。使用量は通
常、HMAベース成分と紫外線架橋性樹脂オリゴマーの合
計量に対して0.5〜５重量％の範囲で選定すればよい。Examples of the photopolymerization initiator used in the present invention include usual benzoin ether type (benzoin isopropyl ether, benzoin isobutyl ether etc.), benzophenone type (benzophenone, p-methoxybenzophenone, p- Bromobenzophenone, etc.), acetophenone type (benzyl methyl ketal, 2,2-diethoxyacetophenone, 1,1-dichloroacetophenone, etc.), and thioxanthone type (2-chlorothioxanthone). The amount used is usually selected in the range of 0.5 to 5% by weight based on the total amount of the HMA base component and the UV-crosslinkable resin oligomer.
本発明に係る紫外線架橋性HMA組成物は、上述のHMAベ
ース成分、紫外線架橋性樹脂オリゴマーおよび光重合開
始剤を所定割合で配合し、更に必要に応じて通常の充填
剤、老化防止剤、重合禁止剤等を加えた系で構成され、
通常80〜160℃の温度で溶融して使用に供する。なお、
溶融粘度は一般に120℃で5000〜500000cpsに設定されて
いる。The UV-crosslinkable HMA composition according to the present invention, the above-mentioned HMA base component, the UV-crosslinkable resin oligomer and the photopolymerization initiator are blended in a predetermined ratio, and further, if necessary, a normal filler, an antioxidant, and a polymerization agent. It is composed of a system that includes inhibitors,
Usually, it is melted at a temperature of 80 to 160 ° C. before use. In addition,
Melt viscosity is generally set at 5000 to 500000 cps at 120 ° C.
本発明接着剤組成物は、次のようにして接着作業を行
うことができる。先ず、該接着剤組成物を溶融し、これ
を被着体（たとえば光デイスク基体）の接着面に厚み10
〜50μにて塗布（たとえばロールコーター使用）した
後、UVを照射し、被着体を重ね合せて0.2〜20kg/cm2で
圧締するか、または重ね合せて圧締後にUV照射する。こ
のようにして従来のHMAの耐熱性を向上させることがで
きる。The adhesive composition of the present invention can be adhered as follows. First, the adhesive composition is melted and applied to the adherend of an adherend (for example, an optical disk substrate) with a thickness of 10
After coating (using a roll coater, for example) at ˜50 μm, UV is irradiated, and the adherends are superposed and pressed at 0.2 to 20 kg / cm 2 , or they are superposed and pressed and then UV irradiated. In this way, the heat resistance of the conventional HMA can be improved.
以上の構成から成る本発明接着剤組成物によれば、低
温、低粘度塗布が可能で、UV照射によつてHMAの物性を
高軟化点、高粘度のものに変えることができ、このため
デイスクに損傷を与えることなく、耐熱性（加えて、耐
湿性、耐候性も含む）を高めることができる。しかも、
従来の熱重合し易いアクリレートモノマーなども含まな
いことから、良好な作業時の熱安定性が達成され、ポツ
トライフが十分に長くなる。またアクリレートモノマー
はデイスク基板のプラスチツクを浸食する危険性があつ
たが、本発明は同時にこの問題を解決したものといえ
る。According to the adhesive composition of the present invention having the above-mentioned constitution, it is possible to apply at low temperature and low viscosity, and it is possible to change the physical properties of HMA to those of high softening point and high viscosity by UV irradiation. The heat resistance (in addition to the humidity resistance and the weather resistance) can be enhanced without damaging the material. Moreover,
Since it does not contain a conventional acrylate monomer that easily undergoes thermal polymerization, good thermal stability during working is achieved, and the pot life is sufficiently long. Further, the acrylate monomer had a risk of eroding the plastic of the disk substrate, but it can be said that the present invention solves this problem at the same time.
次に実施例および比較例を挙げて本発明をより具体的
に説明する。Next, the present invention will be described more specifically with reference to Examples and Comparative Examples.
実施例１ 成分 ポリスチレン−エチレンブチレン共重合体ブロツク状熱
可塑性エラストマー〔シエル化学（株）製、カリフレツ
クスGX−1726〕 −−−20部 両末端アクリロイル基（ウレタンアクリレートタイプ）
含有水添ポリブタジエンオリゴマー〔日本槽達（株）
製、TEAI−3000〕 −−−25部 水添スチレン系粘着付与剤〔理化ハーキユレス（株）
製、リガレツツ1094〕 −−−40部 ポリイソブチレン〔日本石油（株）製、テトラツクス3
T〕 −−−10部 ベンジルメチルケタール〔日本チバガイギー（株）製、
イルガキユアー651〕 −−−３部 上記成分を一括混合して紫外線架橋性HMA組成物を得
る。この組成物の溶融粘度（120℃）は70000cpsであつ
た。Example 1 Component Polystyrene-ethylene butylene copolymer Block-like thermoplastic elastomer [Califlex GX-1726, manufactured by Shell Chemical Co., Ltd.] -20 parts Acryloyl group at both ends (urethane acrylate type)
Containing hydrogenated polybutadiene oligomer [Nippon Tankatsu Co., Ltd.
Manufactured by TEAI-3000] --- 25 parts Hydrogenated styrene tackifier [Rika Hercules Co., Ltd.]
Made by Rigalets 1094] -40 parts polyisobutylene [Nippon Oil Co., Ltd., Tetrax 3
T] ---- 10 parts benzyl methyl ketal [manufactured by Japan Ciba Geigy Co.,
Irgaki Yur 651] --- 3 parts The above components are mixed together to obtain a UV-crosslinkable HMA composition. The melt viscosity (120 ° C.) of this composition was 70,000 cps.
比較例１ 両末端アクリロイル基（ウレタンアクリレートタイ
プ）含有水添ポリブタジエンオリゴマーの代わりに両末
端アクリロイル基含有ポリブタジエンオリゴマー〔出光
石油化学（株）製、Poly bd R−45ACR−LC〕を同量使用
する以外は、実施例１と同様にして接着剤組成物を得
る。Comparative Example 1 Other than using the same amount of polybutadiene oligomer containing acryloyl groups at both ends (Poly bd R-45ACR-LC manufactured by Idemitsu Petrochemical Co., Ltd.) instead of hydrogenated polybutadiene oligomer containing acryloyl groups at both ends (urethane acrylate type). In the same manner as in Example 1, an adhesive composition is obtained.
比較例２ 両末端アクリロイル基含有水添ポリブタジエンオリゴ
マーの代わりにトリメチロールプロパントリアクリレー
トを20部用いる以外は、実施例１と同様にして接着剤組
成物を得る。Comparative Example 2 An adhesive composition is obtained in the same manner as in Example 1 except that 20 parts of trimethylolpropane triacrylate is used instead of the hydrogenated polybutadiene oligomer containing acryloyl groups at both ends.
比較例３ 市販のHMAを使用する。Comparative Example 3 Commercially available HMA is used.
性能試験（結果を表１に示す） （１）熱安定性 各接着剤を120℃の溶融状態で24時間放置させた後、
状態変化を観察する。Performance test (results are shown in Table 1) (1) Thermal stability After each adhesive was left in a molten state at 120 ° C for 24 hours,
Observe the state change.
（２）耐熱クリープ性 ２枚のアクリル板（25×60×1.5mm）に対し、各接着
剤を120℃で溶融して厚み30μにて塗布し、これにUVを4
60mJ/cm2照射後、20mmラツプさせて直ちに重ね合せて10
Kg/cm2で圧締する。得られる貼合板を80℃の雰囲気中
で、耐熱クリープ試験（荷重200g、垂直落下時間）に供
した。(2) Heat-resistant creep resistance Two adhesive plates (25 x 60 x 1.5 mm) were melted with each adhesive at 120 ° C and applied with a thickness of 30μ, and UV was applied to this.
After irradiating 60 mJ / cm 2 , lap it by 20 mm and stack it immediately 10
Tighten with Kg / cm 2 . The obtained laminated plate was subjected to a heat resistant creep test (load 200 g, vertical drop time) in an atmosphere of 80 ° C.
表１の結果から、本発明の接着剤組成物が熱安定性お
よび耐熱クリープ性共に良好であることが認められる。 From the results shown in Table 1, it is confirmed that the adhesive composition of the present invention has good thermal stability and thermal creep resistance.
───────────────────────────────────────────────────── フロントページの続き (56)参考文献 特開 昭62−36476（ＪＰ，Ａ) 特開 昭61−64773（ＪＰ，Ａ) 特開 昭59−59761（ＪＰ，Ａ) 特開 昭56−82863（ＪＰ，Ａ) ─────────────────────────────────────────────────── ─── Continuation of front page (56) Reference JP 62-36476 (JP, A) JP 61-64773 (JP, A) JP 59-59761 (JP, A) JP 56- 82863 (JP, A)
Claims (1)
架橋性成分として１分子中に少なくとも１個のアクリロ
イル基を含有する飽和炭化水素系樹脂オリゴマー、およ
び光重合開始剤から成り、上記ホットメツト型接着剤ベ
ース成分が、ブロック状熱可塑性エラストマー、粘着付
与剤および軟化剤からなり、上記紫外線架橋性樹脂オリ
ゴマーが、１分子中に少なくとも１個の水酸基もしくは
カルボキシル基を含有する水添ポリブタジエン、ポリブ
テン、水添ポリイソプレンまたはポリイソブチレンオリ
ゴマーのアクリレート、ウレタンアクリレート、エポキ
シアクリレートまたはエステルアクリレートであり、か
つ上記紫外線架橋性樹脂オリゴマーの使用量がホットメ
ルト型接着剤ベース成分100重量部に対して５〜100重量
部、および上記光重合開始剤の使用量がホットメルト型
接着剤ベース成分と紫外線架橋性樹脂オリゴマーの合計
量に対して0.5〜５重量％であることを特徴とする紫外
線架橋性ホットメルト型接着剤組成物。1. A hot-melt adhesive base component, a saturated hydrocarbon resin oligomer containing at least one acryloyl group in one molecule as a UV-crosslinkable component, and a photopolymerization initiator. The agent base component is composed of a block-shaped thermoplastic elastomer, a tackifier and a softening agent, and the above UV-crosslinkable resin oligomer contains hydrogenated polybutadiene, polybutene, water containing at least one hydroxyl group or carboxyl group in one molecule. An acrylate, urethane acrylate, epoxy acrylate, or ester acrylate of an added polyisoprene or polyisobutylene oligomer, and the amount of the UV-crosslinkable resin oligomer used is 5 to 100 parts by weight per 100 parts by weight of the hot-melt adhesive base component. , And the above light weight UV-crosslinkable hot-melt adhesive composition, characterized in that the amount of initiator is 0.5 to 5% by weight relative to the total weight of the hot melt adhesive base component and an ultraviolet crosslinking resin oligomer.
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62301679A JP2520145B2 (en) | 1987-11-30 | 1987-11-30 | Ultraviolet-crosslinkable hot melt adhesive composition |
| US07/277,347 US5128388A (en) | 1987-11-30 | 1988-11-29 | Hot melt adhesive crosslinkable by ultraviolet irradiation, optical disc using the same and process for preparing thereof |
| DE3840391A DE3840391A1 (en) | 1987-11-30 | 1988-11-30 | HOT GLAZING ADHESIVE, OPTICAL DISK PRODUCED UNDER USE AND METHOD FOR THE PRODUCTION THEREOF |
| GB8827961A GB2212812B (en) | 1987-11-30 | 1988-11-30 | Hot melt adhesive |
| GB8910661A GB2217257B (en) | 1987-11-30 | 1989-05-09 | Optical disc and process for making it |
| US07/864,648 US5227213A (en) | 1987-11-30 | 1992-04-07 | Hot melt adhesive crosslinkable by ultraviolet irradiation, optical disc using the same and process for preparing thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62301679A JP2520145B2 (en) | 1987-11-30 | 1987-11-30 | Ultraviolet-crosslinkable hot melt adhesive composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH01141969A JPH01141969A (en) | 1989-06-02 |
| JP2520145B2 true JP2520145B2 (en) | 1996-07-31 |
Family
ID=17899827
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62301679A Expired - Fee Related JP2520145B2 (en) | 1987-11-30 | 1987-11-30 | Ultraviolet-crosslinkable hot melt adhesive composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2520145B2 (en) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPWO2005090509A1 (en) * | 2004-03-19 | 2008-01-31 | 株式会社スリーボンド | Photo-curable thermosensitive film adhesive composition |
| JP2006265508A (en) * | 2005-03-22 | 2006-10-05 | Shin Osaka Seal Insatsu Kk | Ultraviolet-curable hot-melt composition |
| JP4884824B2 (en) * | 2005-04-28 | 2012-02-29 | 新田ゼラチン株式会社 | UV curable hot melt sealant |
| WO2006117156A1 (en) * | 2005-05-02 | 2006-11-09 | Cytec Surface Specialties, S.A. | Radiation curable urethane (meth)acrylate polymer and adhesives formulated with them |
| JP5013585B2 (en) * | 2006-09-06 | 2012-08-29 | 日立化成ポリマー株式会社 | Reactive hot melt adhesive composition and bonding method using the same |
| JP2008063407A (en) * | 2006-09-06 | 2008-03-21 | Hitachi Kasei Polymer Co Ltd | Reactive hot-melt adhesive composition and method for bonding using the same |
| JP5129556B2 (en) * | 2007-12-14 | 2013-01-30 | サンスター技研株式会社 | Adhesive composition |
| WO2011112447A2 (en) | 2010-03-09 | 2011-09-15 | 3M Innovative Properties Company | Heat activated optically clear adhesive for bonding display panels |
| JP2011184582A (en) | 2010-03-09 | 2011-09-22 | Three M Innovative Properties Co | Adhesive sheet for optical use |
| CN114806462A (en) * | 2021-01-19 | 2022-07-29 | 韦尔通(厦门)科技股份有限公司 | Photocurable hot melt adhesive with good adhesion to polar substrates and preparation method thereof |
| CN114806471A (en) * | 2021-01-19 | 2022-07-29 | 韦尔通(厦门)科技股份有限公司 | Light-curable rubber hot melt adhesive with extremely high thermal stability and preparation method thereof |
| JP2026059423A (en) * | 2024-09-26 | 2026-04-07 | ａｒｔｉｅｎｃｅ株式会社 | Hot melt adhesive, adhesive sheets, items |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5682863A (en) * | 1979-12-12 | 1981-07-06 | Furukawa Electric Co Ltd:The | Hot-melt type adhesive composition |
| JPS5959761A (en) * | 1982-09-29 | 1984-04-05 | Harima Kasei Kogyo Kk | rubber adhesive |
| JPS6164773A (en) * | 1984-09-05 | 1986-04-03 | Nitto Electric Ind Co Ltd | Photo-setting, pressure-sensitive adhesive |
| JPS6236476A (en) * | 1985-08-12 | 1987-02-17 | Semedain Kk | Electromagnetic wave curing solvent-free adhesive composition |
-
1987
- 1987-11-30 JP JP62301679A patent/JP2520145B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH01141969A (en) | 1989-06-02 |
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