JPH01207372A - Heat-activated delayed type tacky agent composition and heat-activated delayed type tacky sheet - Google Patents
Heat-activated delayed type tacky agent composition and heat-activated delayed type tacky sheetInfo
- Publication number
- JPH01207372A JPH01207372A JP63032419A JP3241988A JPH01207372A JP H01207372 A JPH01207372 A JP H01207372A JP 63032419 A JP63032419 A JP 63032419A JP 3241988 A JP3241988 A JP 3241988A JP H01207372 A JPH01207372 A JP H01207372A
- Authority
- JP
- Japan
- Prior art keywords
- heat
- activated delayed
- polyurethane
- molecule
- polyurethane resin
- 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.)
- Pending
Links
- 230000003111 delayed effect Effects 0.000 title claims abstract description 29
- 239000000203 mixture Substances 0.000 title claims abstract description 14
- 230000001070 adhesive effect Effects 0.000 claims abstract description 31
- 239000000463 material Substances 0.000 claims abstract description 29
- 239000000853 adhesive Substances 0.000 claims abstract description 28
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000007787 solid Substances 0.000 claims abstract description 18
- 229920005749 polyurethane resin Polymers 0.000 claims abstract description 17
- 239000004014 plasticizer Substances 0.000 claims abstract description 13
- -1 polytetramethylene Polymers 0.000 claims abstract description 13
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims abstract description 13
- 239000006185 dispersion Substances 0.000 claims abstract description 8
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000004820 Pressure-sensitive adhesive Substances 0.000 claims description 19
- 229920002635 polyurethane Polymers 0.000 claims description 17
- 239000004814 polyurethane Substances 0.000 claims description 17
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 9
- 229920001577 copolymer Polymers 0.000 claims description 9
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 9
- 229920005862 polyol Polymers 0.000 claims description 9
- 150000003077 polyols Chemical class 0.000 claims description 9
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 6
- 239000002994 raw material Substances 0.000 claims description 6
- 238000001994 activation Methods 0.000 claims description 5
- 230000004913 activation Effects 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 239000001361 adipic acid Substances 0.000 claims description 3
- 235000011037 adipic acid Nutrition 0.000 claims description 3
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 claims description 3
- 238000007725 thermal activation Methods 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 2
- 229920000728 polyester Polymers 0.000 claims description 2
- 229920005906 polyester polyol Polymers 0.000 claims 1
- 238000000576 coating method Methods 0.000 abstract description 14
- 239000011248 coating agent Substances 0.000 abstract description 13
- 239000002861 polymer material Substances 0.000 abstract description 8
- 230000000903 blocking effect Effects 0.000 abstract description 7
- 229920003023 plastic Polymers 0.000 abstract description 7
- 239000004033 plastic Substances 0.000 abstract description 7
- 208000019901 Anxiety disease Diseases 0.000 abstract 1
- 230000036506 anxiety Effects 0.000 abstract 1
- 230000001747 exhibiting effect Effects 0.000 abstract 1
- 239000000758 substrate Substances 0.000 abstract 1
- 238000004804 winding Methods 0.000 abstract 1
- 239000000839 emulsion Substances 0.000 description 11
- 239000000123 paper Substances 0.000 description 10
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Chemical class C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 9
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Chemical class 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 8
- 229920001038 ethylene copolymer Polymers 0.000 description 8
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Chemical class OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- HDERJYVLTPVNRI-UHFFFAOYSA-N ethene;ethenyl acetate Chemical group C=C.CC(=O)OC=C HDERJYVLTPVNRI-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- VOWAEIGWURALJQ-UHFFFAOYSA-N Dicyclohexyl phthalate Chemical compound C=1C=CC=C(C(=O)OC2CCCCC2)C=1C(=O)OC1CCCCC1 VOWAEIGWURALJQ-UHFFFAOYSA-N 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- ZSBRYDJXHOFQMW-UHFFFAOYSA-N chloroethene;ethene;ethenyl acetate Chemical group C=C.ClC=C.CC(=O)OC=C ZSBRYDJXHOFQMW-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- KCXZNSGUUQJJTR-UHFFFAOYSA-N Di-n-hexyl phthalate Chemical compound CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCC KCXZNSGUUQJJTR-UHFFFAOYSA-N 0.000 description 2
- 239000000919 ceramic Substances 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 125000005442 diisocyanate group Chemical group 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- 230000001804 emulsifying effect Effects 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 239000012943 hotmelt Substances 0.000 description 2
- 239000004816 latex Substances 0.000 description 2
- 229920000126 latex Polymers 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- 229920003048 styrene butadiene rubber Polymers 0.000 description 2
- LVTPRIAGCBEGPW-UHFFFAOYSA-N (2-benzoyloxyphenyl) benzoate Chemical class C=1C=CC=CC=1C(=O)OC1=CC=CC=C1OC(=O)C1=CC=CC=C1 LVTPRIAGCBEGPW-UHFFFAOYSA-N 0.000 description 1
- XFDQLDNQZFOAFK-UHFFFAOYSA-N 2-benzoyloxyethyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCCOC(=O)C1=CC=CC=C1 XFDQLDNQZFOAFK-UHFFFAOYSA-N 0.000 description 1
- LUNMJRJMSXZSLC-UHFFFAOYSA-N 2-cyclopropylethanol Chemical compound OCCC1CC1 LUNMJRJMSXZSLC-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000002174 Styrene-butadiene Substances 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- PJLLCGNQPWXWGL-UHFFFAOYSA-N [3-benzoyloxy-2-(benzoyloxymethyl)-2-methylpropyl] benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC(COC(=O)C=1C=CC=CC=1)(C)COC(=O)C1=CC=CC=C1 PJLLCGNQPWXWGL-UHFFFAOYSA-N 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 239000011247 coating layer Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- VNGOYPQMJFJDLV-UHFFFAOYSA-N dimethyl benzene-1,3-dicarboxylate Chemical compound COC(=O)C1=CC=CC(C(=O)OC)=C1 VNGOYPQMJFJDLV-UHFFFAOYSA-N 0.000 description 1
- DWNAQMUDCDVSLT-UHFFFAOYSA-N diphenyl phthalate Chemical compound C=1C=CC=C(C(=O)OC=2C=CC=CC=2)C=1C(=O)OC1=CC=CC=C1 DWNAQMUDCDVSLT-UHFFFAOYSA-N 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- 210000004905 finger nail Anatomy 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 229920001490 poly(butyl methacrylate) polymer Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229920001909 styrene-acrylic polymer Polymers 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- SYDJVRWZOWPNNO-UHFFFAOYSA-N sucrose-benzoate Natural products OCC1OC(OC2(COC(=O)c3ccccc3)OC(CO)C(O)C2O)C(O)C(O)C1O SYDJVRWZOWPNNO-UHFFFAOYSA-N 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides 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
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 125000005628 tolylene group Chemical group 0.000 description 1
- CBKMOPGKNJBDFA-UHFFFAOYSA-N tricyclohexyl 2-hydroxypropane-1,2,3-tricarboxylate Chemical compound C1CCCCC1OC(=O)CC(C(=O)OC1CCCCC1)(O)CC(=O)OC1CCCCC1 CBKMOPGKNJBDFA-UHFFFAOYSA-N 0.000 description 1
- 229920006163 vinyl copolymer Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4854—Polyethers containing oxyalkylene groups having four carbon atoms in the alkylene group
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
- C09J175/08—Polyurethanes from polyethers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
- C08L2666/02—Organic macromolecular compounds, natural resins, waxes or and bituminous materials
- C08L2666/04—Macromolecular compounds according to groups C08L7/00 - C08L49/00, or C08L55/00 - C08L57/00; Derivatives thereof
Abstract
Description
【発明の詳細な説明】
（Ａ＞産業上の利用分野
本発明は、常温では非粘着性であるが、加熱により活性
化して粘着性（タック）が顕われ、しかも熱源から離れ
た後も半永久的に粘着性が持続する熱活性遅延型粘着剤
組成物およびそれを基材シート上に塗設してなる熱活性
遅延型粘着シートに関する。Detailed Description of the Invention (A> Industrial Application Fields The present invention is non-tacky at room temperature, but becomes tacky when activated by heating, and remains semi-permanent even after being removed from the heat source. The present invention relates to a heat-activated delayed pressure-sensitive adhesive composition that maintains long-lasting tackiness and a heat-activated delayed pressure-sensitive adhesive sheet formed by coating the same on a base sheet.
（Ｂ）従来の技術
熱活性遅延型粘着シートはサーマルデイレードタック紙
とも呼ばれ、例えば「接着便覧」第１２版（高分子刊行
会発行、昭和５５年）に記載されており、基本的に、ポ
リ酢酸ビニル、ポリメタクリル酸ブチル、塩化ビニル−
塩化ビニリデンコポリマー、合成ゴム、酢酸ビニル−ア
クリル酸２−エチルへキシルコポリマー、酢酸ビニル−
エチレンコポリマー、ビニルピロリドン−スチレンコポ
リマー、スチレン−ブタジェンコポリマー、ビニルピロ
リドン−アクリル酸エチルコポリマー、などの高分子材
料（ポリマー）と、フタル酸ジフェニル、フタル酸ジヘ
キシル、フタル酸ジシクロヘキシル、フタル酸ジヒドロ
アビエチル、イソフタル酸ジメチル、安息香酸スクロー
ス、二安息香酸エチレングリコール、三安息香酸トリメ
チロールエタン、三安息香酸グリセリド、四安息香酸ペ
ンタエリトリット、へ酢酸スクロース、クエン酸トリシ
クロヘキシル、Ｎ−シクロヘキシル−ｐ−トルエンスル
ホンアミド、カテコールジベンゾエートなどの常温で固
体の可塑剤とロジン誘導体（ロジン、重合ロジン、水添
ロジン及びそれらのグリセリン、ペンタエリスリトール
等とのエステル、樹脂酸ダイマー、など）、テルペン樹
脂系、石油樹脂系、フェノール樹脂系、キシレン樹脂系
などの粘着付与剤とを含有する塗層を有したシートであ
る。(B) Conventional technology A heat-activated delayed adhesive sheet is also called thermal delayed tack paper, and is described in, for example, the 12th edition of "Adhesive Handbook" (published by Kobunshi Kankai, 1982), and basically , polyvinyl acetate, polybutyl methacrylate, vinyl chloride
Vinylidene chloride copolymer, synthetic rubber, vinyl acetate-2-ethylhexyl acrylate copolymer, vinyl acetate-
Polymer materials (polymers) such as ethylene copolymer, vinylpyrrolidone-styrene copolymer, styrene-butadiene copolymer, vinylpyrrolidone-ethyl acrylate copolymer, diphenyl phthalate, dihexyl phthalate, dicyclohexyl phthalate, dihydroabiethyl phthalate , dimethyl isophthalate, sucrose benzoate, ethylene glycol dibenzoate, trimethylolethane tribenzoate, glyceride tribenzoate, pentaerythritol tetrabenzoate, sucrose helacetate, tricyclohexyl citrate, N-cyclohexyl-p-toluene Plasticizers that are solid at room temperature such as sulfonamides and catechol dibenzoates, rosin derivatives (rosin, polymerized rosin, hydrogenated rosin and their esters with glycerin, pentaerythritol, etc., resin acid dimers, etc.), terpene resins, petroleum This sheet has a coating layer containing a tackifier such as resin, phenol resin, or xylene resin.
ここで高分子材料は粘着・接着力の根源を為すものであ
り、粘着付与剤は加熱により活性化された際に粘着性を
増すための成分である。固体可塑剤は常温では固体であ
って高分子材料に塑性を与えず、加熱により溶融し高分
子材料を膨潤・溶解して粘着性を発現させる。そして−
旦溶融した後は、極めてゆっくりと固化するので、熱活
性化後の粘着シートの粘着保持時間を長くとることがで
きる。Here, the polymeric material is the source of adhesive strength, and the tackifier is a component that increases tackiness when activated by heating. Solid plasticizers are solid at room temperature and do not impart plasticity to the polymeric material, but when heated, they melt and swell and dissolve the polymeric material, making it sticky. And-
Once melted, it solidifies extremely slowly, so that the adhesive retention time of the adhesive sheet after heat activation can be extended.
また、熱活性遅延型粘着シート製造用の塗工液の形態と
しては、ホットメルトタイプ（例；特開昭５５−１６０
５５号公報、特開昭５６−１０６９８４号公報）、有機
溶剤タイプ（例；特開昭５１−１１１２４６号公報）や
水性タイプ（「高分子ラテックス接着剤」室井宗−著、
高分子刊行会発行）の例が見られた。In addition, as the form of the coating liquid for producing a heat-activated delayed pressure-sensitive adhesive sheet, hot-melt type (e.g., JP-A-55-160
No. 55, JP-A-56-106984), organic solvent type (e.g., JP-A-51-111246) and water-based type ("Polymer Latex Adhesive" by So Muroi,
(Published by Kobunshi Publishing Association).
（Ｃ）発明が解決しようとする問題点
高分子材料、粘着付与剤および固体可塑剤を調合した組
成物（塗工液）の形態として、ホットメルトタイプある
いは有機溶剤タイプを採る時には、固体可塑剤が熱ある
いは有機溶剤により溶けるために塗工された直後のシー
トは活性化していて粘着状態にあり、これを非粘着化す
るには固体可塑剤の再結晶化を待つ必要があって、非常
に長時間放置する工程が必要という問題点がおった。(C) Problem to be solved by the invention When the composition (coating liquid) containing a polymeric material, a tackifier, and a solid plasticizer is in the form of a hot melt type or an organic solvent type, the solid plasticizer is Because it is melted by heat or organic solvents, the sheet immediately after coating is activated and sticky, and in order to make it non-stick, it is necessary to wait for the solid plasticizer to recrystallize, which is extremely difficult. There was a problem that a process of leaving it for a long time was required.
本発明は離型剤を塗布した特殊な基材シートに塗布する
ことなく、塗工直後に直接巻き取ってもブロッキングの
心配のない熱活性遅延型粘着シートを提供することが第
１の目的である。The first object of the present invention is to provide a heat-activated delayed pressure-sensitive adhesive sheet that can be rolled up directly after coating without worrying about blocking, without having to be coated on a special base sheet coated with a release agent. be.
また、従来の熱活性遅延型粘着シートは貼付する被着体
のうち特に極性の低いプラスチック材料に対しては貼付
後早期に被着体からの剥離が生じ実用価値の乏しいもの
であった。従って、本発明の第２の目的は、極性の低い
プラスチック材料に対しても、十分長く粘・接着性を持
続できる熱活性遅延型粘着シートを提供することである
。In addition, conventional heat-activated delayed pressure-sensitive adhesive sheets tend to peel off from the adherend at an early stage after application, especially when applied to a plastic material with low polarity, resulting in poor practical value. Therefore, a second object of the present invention is to provide a heat-activated delayed pressure-sensitive adhesive sheet that can maintain adhesiveness and adhesion for a sufficiently long time even on plastic materials with low polarity.
（Ｄ＞問題点を解決するための手段
以上のことから、本発明者は先づ塗工用組成物の形態と
しては固体可塑剤を固体状態のまま塗工するために組成
物の各素材を水性分散体状に調合して水性塗液化するこ
とを選択した。これにより乾燥条件として粘着シートが
熱活性しない程度の条件を選択すればロール状に巻取っ
てもブロッキングを生じない熱活性遅延型粘着シートを
直接製造することができた。またこの際に固体可塑剤の
粉砕粒子径を塗工面の平滑性を妨げない程度に大きくす
ることにより、ブロッキングを一層防止する効果がある
ことも判った。これは各素材を水性分散体状に調合して
塗工したことによる大きな利点であった。一方、接着性
については熱活性遅延型粘着シートで従来公知の前記の
如き高分子材料を用いては極性の低いプラスチック材料
に対しては十分に長い粘・接着性を得ることができず、
その他の高分子材料について広範にかつ詳細に調べた結
果、遂にポリウレタン樹脂でその分子中に直鎖状テトラ
メチレン構造を有するという、特定構造のポリウレタン
樹脂が熱活性遅延型粘着剤用の高分子材料として特に優
秀で、無極性プラスチック類例えばポリプロピレンやポ
リエチレンに対してさえ優れた粘接着性を示す熱活性遅
延型粘着剤を与えることを本発明者が見出した。(D> Means for Solving the Problems For the reasons mentioned above, the present inventor first proposed that each material of the composition be used in the form of a coating composition in order to coat the solid plasticizer in a solid state. We chose to formulate it into an aqueous dispersion and make it into an aqueous coating liquid.This is a delayed heat activation type that does not cause blocking even when wound into a roll if the drying conditions are such that the adhesive sheet is not thermally activated. It was possible to directly manufacture an adhesive sheet.It was also found that blocking could be further prevented by increasing the crushed particle size of the solid plasticizer to an extent that did not interfere with the smoothness of the coated surface. This was a major advantage of preparing each material in the form of an aqueous dispersion and applying the coating.On the other hand, as for the adhesion, it was possible to improve the adhesion by using the previously known polymeric materials mentioned above in heat-activated delayed pressure-sensitive adhesive sheets. cannot obtain sufficient long-term adhesiveness and adhesion for plastic materials with low polarity.
As a result of extensive and detailed research on other polymeric materials, we finally found a polyurethane resin with a specific structure, which has a linear tetramethylene structure in its molecule, as a polymeric material for heat-activated delayed adhesives. The present inventors have found that the present invention provides a heat-activated delayed adhesive which is particularly excellent as a heat-activated adhesive and exhibits excellent adhesion even to non-polar plastics such as polypropylene and polyethylene.
高分子材料、粘着付与剤および固体可塑剤の好ましい配
合比としては、高分子材料１００重量部に対して、粘着
付与剤が１０〜２００重量部、固体可塑剤が５０〜３０
０重量部であり、上記特定構造のポリウレタン樹脂は高
分子材料のうちの１０〜１００重量％で本発明の目的を
達成することができる。粘着付与剤が１０重量部未満で
は熱活性後の粘・接着力が低く、２００重量部を越える
とロール状に巻き取った場合のブロッキング現象が激し
くなる。固体可塑剤が５０重量部未満では熱活性による
粘着性の発現がおこりにくく、３０Ｏ重量部を越えると
熱活性化（麦の粘着部の凝集力が低下し、また熱活性後
の粘着持続時間（オープンタイム）が短くなることから
実用的ではない。A preferred blending ratio of the polymer material, tackifier, and solid plasticizer is 10 to 200 parts by weight of the tackifier and 50 to 30 parts by weight of the solid plasticizer per 100 parts by weight of the polymer material.
The purpose of the present invention can be achieved with the amount of the polyurethane resin having the specific structure being 10 to 100% by weight of the polymer material. If the tackifier is less than 10 parts by weight, the tackiness and adhesive strength after heat activation will be low, and if it exceeds 200 parts by weight, the blocking phenomenon will become severe when wound into a roll. If the solid plasticizer is less than 50 parts by weight, it is difficult to develop adhesiveness due to thermal activation, and if it exceeds 300 parts by weight, the cohesive force of the sticky part of wheat decreases, and the adhesive duration after thermal activation ( It is not practical because the open time) is shortened.
ポリウレタンは、下式に示すようにジイソシアネートと
ジオール（ポリオール）の重付加反応によって得られる
。Polyurethane is obtained by polyaddition reaction of diisocyanate and diol (polyol) as shown in the following formula.
０ＣＮ−Ｒ−ＮＣＯ＋ＨＯ−Ｒ’ −ＯＨ通常、ジイソ
シアネートはポリウレタンのハードセグメントを与え、
ジオール（ポリオール）はソフトセグメントを与える。0CN-R-NCO+HO-R' -OH Usually, the diisocyanate provides the hard segment of the polyurethane,
Diols (polyols) provide soft segments.
本発明者は多数の種類のポリウレタン樹脂について熱活
性遅延型粘着剤組成物へ含有させて見て、その粘接着性
能向上効果を試験したところ、被着体がポリプロピレン
やポリエチレンのような無極性ポリオレフィン材料であ
る場合は、特定の分子構造を有するポリウレタンがとり
わけ優れた粘接着性能を発揮することを見出した。The present inventor incorporated many types of polyurethane resins into heat-activated delayed pressure-sensitive adhesive compositions and tested their adhesive performance improvement effects. In the case of polyolefin materials, it has been found that polyurethane having a specific molecular structure exhibits particularly excellent adhesive performance.
例えば、ポリウレタンのソフトセグメントの原料である
ポリオールがポリテトラメチレングリコール
Ｈｆ０ＣＩ（ｚｃＨｚｃｌ（ｚｃＨｚ→７−ＯＨである
場合、
あるいはエチレングリコール、ジエチレングリコール、
プロピレングリコールもしくは１，６−ヘキサンジオー
ルとアジピン酸とのポリエステル型ポリオールである場
合、などである。For example, when the polyol that is the raw material for the soft segment of polyurethane is polytetramethylene glycol Hf0CI (zcHzcl (zcHz→7-OH), or ethylene glycol, diethylene glycol,
Examples include a polyester type polyol of propylene glycol or 1,6-hexanediol and adipic acid.
ここで共通して言えることは、本発明で優れた効果を発
揮するポリウレタン樹脂は皆その分子中に直鎖状テトラ
メチレン構造を有していることが特徴である。What is common here is that all polyurethane resins that exhibit excellent effects in the present invention are characterized by having a linear tetramethylene structure in their molecules.
このような、その分子中に直鎖状テトラメチレン構造を
有するポリウレタン樹脂が熱活性遅延型粘着剤組成物も
しくはその塗設シートにおいて特に優れた粘接着性を与
えると記載された文献は未だ見当たらない。No literature has yet been found stating that such a polyurethane resin having a linear tetramethylene structure in its molecule provides particularly excellent adhesive properties in a heat-activated delayed adhesive composition or a coated sheet thereof. do not have.
本発明を実際に行なうには、上記特定分子構造を有する
ポリウレタン樹脂の水性エマルジョンを他の原材料の水
性エマルジョンと配合、混合して調合する。To actually carry out the present invention, an aqueous emulsion of the polyurethane resin having the above-mentioned specific molecular structure is blended and mixed with an aqueous emulsion of other raw materials.
水性エマルジョン化するのは公知の方法によるが、例え
ば有機溶媒に溶かして水中に乳化するとか、加熱不溶融
物を水中に乳化するとかの方法で行なう。The aqueous emulsion can be made by a known method, such as by dissolving it in an organic solvent and emulsifying it in water, or by emulsifying a heated insoluble material in water.
多様な被着体への接着特性（接着力、粘着力、凝集力、
等）、耐ブロッキング性、等を微妙にコントロールする
ためにポリウレタンエマルジョンと併用使用する高分子
材料としては、従来公知の前記高分子材料をエマルジョ
ン化したものが使用されるが、好ましい例としては酢酸
ビニル系コポリマー（例；酢酸ビニル−エチレンコポリ
マー）、アクリル酸エステル系コポリマー（例；スチレ
ン−アクリル酸エステルコポリマー）等が挙げられる。Adhesive properties to various adherends (adhesive strength, adhesive strength, cohesive strength,
etc.), blocking resistance, etc.), blocking resistance, etc., the polymer material used in combination with the polyurethane emulsion is an emulsion of the conventionally known polymer materials, but a preferred example is acetic acid. Examples include vinyl copolymers (eg, vinyl acetate-ethylene copolymers), acrylic ester copolymers (eg, styrene-acrylic ester copolymers), and the like.
いうまでもなく、熱活性遅延型粘着シートは多岐に亘る
被着体材料、例えば紙、ガラス、金属、陶磁器、セラミ
ックス、各種プラスチック、等への優れた粘接着性を実
用上要求されるので、異種高分子材料の併用使用による
配合が行なわれることが多い。そして、熱活性化後の該
粘着剤においては各素材の分離が起ってはならないので
、異種高分子材料の選択は重要で安定なポリマーアロイ
を形成する組合せを目指す必要がある。Needless to say, thermally activated delayed adhesive sheets are practically required to have excellent adhesion to a wide variety of adherend materials, such as paper, glass, metals, ceramics, ceramics, and various plastics. , compounding is often done by using different types of polymeric materials in combination. Since separation of each material must not occur in the adhesive after heat activation, the selection of different polymeric materials is important and it is necessary to aim for a combination that forms a stable polymer alloy.
本発明においては、上述のようなポリウレタンは種々の
異種高分子材料との相溶性に優れている結果、良い効果
を発揮できたと見られるが、ポリウレタンと組合わすこ
との出来る数多くの異種高分子材料の中でもラジカル乳
化重合法になる酢酸ビニル−エチレン共重合体、酢酸ビ
ニル−塩化ビニル−エチレン共重合体、等の酢酸ビニル
系共重合体と組合わせると、広い用途に対応できる実用
性の高い該粘着剤が得られることも本発明者は見出して
いる。In the present invention, it appears that polyurethane as described above was able to exhibit good effects as a result of its excellent compatibility with various different types of polymeric materials, but there are many different types of polymeric materials that can be combined with polyurethane. Among them, when combined with vinyl acetate-based copolymers such as vinyl acetate-ethylene copolymer, vinyl acetate-vinyl chloride-ethylene copolymer, etc., which can be processed by radical emulsion polymerization, it becomes a highly practical polymer that can be used in a wide range of applications. The inventor has also discovered that an adhesive can be obtained.
粘着付与剤としては、従来公知のものが使用できるが、
好ましい例として、軟化点が９０〜１３Ｏ°Ｃのロジン
あるいは重合ロジンのグリセリン、ペンタエリスリトー
ル等によるエステル化物が挙げられる。As the tackifier, conventionally known ones can be used, but
Preferred examples include rosin or polymerized rosin esterified with glycerin, pentaerythritol, etc., having a softening point of 90 to 130°C.
水性塗工方式としては、通常一般に行なわれているロー
ルコータ−、エアーナイフコーター、ブレードコーター
、グラビアコーター等が使用でき、塗工量としては乾燥
固形分で１Ｑ〜３０９／尻が好ましい。As the aqueous coating method, commonly used roll coaters, air knife coaters, blade coaters, gravure coaters, etc. can be used, and the coating amount is preferably 1Q to 309/l in terms of dry solid content.
（Ｅ）実施例
本実施例においてはＵ部Ｊは仝て「固形分重量部」を表
わす。(E) Example In this example, U and J represent "parts by weight of solid content."
実施例１
トリレンジインシアネートとポリテトラメチレングリコ
ールとから合成されたポリウレタン（繰り返し単位は下
記構造式）の水性エマルジョン５０部
ＣＨ３＜ｍは正の整数〉
酢酸ビニル−塩化ビニル−エチレン共重合体の水性エマ
ルジョン ５０部ロジンエステル水
性エマルジョン １００部フタル酸ジシクロヘキシル水
性分散物
２００部
上記配合の水性塗液（固形分濃度５５％）を坪量９（１
／ｍの両面アート紙の片面へ乾燥塗布量２０ｇ／Ｔｒｔ
となるように塗布し、５０’Ｃで乾燥し、非粘着性の塗
被紙を得た。Example 1 50 parts of an aqueous emulsion of polyurethane (the repeating unit has the following structural formula) synthesized from tolylene diincyanate and polytetramethylene glycol CH3 <m is a positive integer> Vinyl acetate-vinyl chloride-ethylene copolymer Aqueous emulsion: 50 parts Rosin ester aqueous emulsion: 100 parts Dicyclohexyl phthalate aqueous dispersion: 200 parts
Dry coating amount 20g/Trt on one side of /m double-sided art paper
It was coated to give a non-tacky coated paper and dried at 50'C.
比較例１
実施例１におけるポリウレタンを全く加えず、酢酸ビニ
ル−塩化ビニル−エチレン共重合体を１００部使用し、
他は同様にして比較用塗被紙を作製した。Comparative Example 1 Using 100 parts of vinyl acetate-vinyl chloride-ethylene copolymer without adding any polyurethane in Example 1,
A comparative coated paper was produced in the same manner as above.
実施例２
トリレンジイソシアネートとポリ（ジエチレングリコー
ルアジペート）とから合成されたポリウレタン（繰り返
し単位は下記構造式）の水性エマルジョン
３０部Ｃ）１３
− ＣＨ２ＣＨ２ＣＨ２ＣＨ２−Ｃ−０−ＣＨ□ＣＨ２
−Ｏ−ＣＩｌ□ＧＨｚ −Ｏｉ「くｎは正の整数〉
酢酸ビニル−エチレン共重合体の
水性エマルジョン ７０部ロジンエス
テルの水性エマルジョン １２５部フタル酸ジシクロヘ
キシル水性分散物
２５０部
上記配合の水性塗液（固形分濃度５４．５％）を坪量８
０ｇ／７７ｆの片面アート紙の裏面のバリアーコート層
（カオリン２５部 ＳＢＲラテックス’１００部からな
る層、塗布量４７Ｉｊ／ゴ）の上へ乾燥塗布量１３ｇ／
ｍとなるように塗布し、４０°Ｃで乾燥し、非粘着性の
塗被紙を得た。Example 2 Aqueous emulsion of polyurethane (repeating unit has the following structural formula) synthesized from tolylene diisocyanate and poly(diethylene glycol adipate)
30 parts C) 13 - CH2CH2CH2CH2-C-0-CH□CH2
-O-CIl□GHz -Oi (n is a positive integer) Aqueous emulsion of vinyl acetate-ethylene copolymer 70 parts Aqueous emulsion of rosin ester 125 parts Dicyclohexyl phthalate aqueous dispersion 250 parts Aqueous coating liquid of the above formulation ( Solid content concentration 54.5%) and basis weight 8
A dry coating amount of 13 g/g was applied onto the barrier coat layer (a layer consisting of 25 parts of kaolin and 100 parts of SBR latex', coating amount of 47 Ij/g) on the back side of 0 g/77 f single-sided art paper.
m and dried at 40°C to obtain a non-tacky coated paper.
比較例２
実施例２におけるポリウレタンを全く加えず、酢酸ビニ
ル−エチレン共重合体を１００部使用し、他は同様にし
て比較用塗被紙を作製した。Comparative Example 2 A comparative coated paper was prepared in the same manner as in Example 2 except that 100 parts of vinyl acetate-ethylene copolymer was used without adding any polyurethane.
実施例３
実施例１．２および比較例１．２で得た熱活性遅延型粘
着シートの紙片を夫々１２５℃３０秒なる加熱条件で活
性化し、ポリエチレン製の瓶の胴へ貼り付けて室温にて
３力月経過した後、爪で剥がすという実用テストを行な
った。Example 3 Paper pieces of the heat-activated delayed pressure-sensitive adhesive sheets obtained in Example 1.2 and Comparative Example 1.2 were each activated by heating at 125°C for 30 seconds, attached to the body of a polyethylene bottle, and allowed to cool to room temperature. After 3 months had passed, we conducted a practical test by peeling it off with our fingernails.
実施例１．２より得た粘着シートは瓶に強固に粘接着し
ていて、無理に剥がすと紙基材が破れてしまったく基材
破壊を示した。）
一方、比較例１．２より得た粘着シートは瓶と粘着剤の
界面から容易に剥がれた（界面破壊ないしは剥離破壊を
示した）。The pressure-sensitive adhesive sheets obtained in Examples 1 and 2 were firmly adhesively attached to the bottle, and when they were forcibly removed, the paper base material was torn, indicating destruction of the base material. ) On the other hand, the pressure-sensitive adhesive sheet obtained in Comparative Example 1.2 was easily peeled off from the interface between the bottle and the pressure-sensitive adhesive (indicating interfacial destruction or peeling failure).
即ち、本発明になる粘着シートの方がポリエチレンに対
する粘接着性が格段に優れていることが判明した。That is, it was found that the pressure-sensitive adhesive sheet of the present invention has significantly better adhesive properties to polyethylene.
（Ｆ）発明の効果
上述の通り、その分子中に直鎖状テトラメチレン構造を
有するポリウレタン樹脂を含有する高分子材料を接着剤
として加えた熱活性遅延型粘着剤は被管材料が極性の低
いプラスチック材料の場合でも優れた粘接着性能を発揮
することが明らかとなった。(F) Effects of the invention As mentioned above, the heat-activated delayed pressure-sensitive adhesive, in which a polymeric material containing a polyurethane resin having a linear tetramethylene structure in its molecule is added as an adhesive, has a tube material with low polarity. It has become clear that it exhibits excellent adhesive performance even when used with plastic materials.
Claims (8)
量部に対して粘着付与剤１０〜２００重量部および固体
可塑剤５０〜３００重量部を水性分散体状に調合して得
た熱活性遅延型粘着剤組成物において、ポリウレタン樹
脂がその分子中に直鎖状テトラメチレン構造を有するこ
とを特徴とする熱活性遅延型粘着剤組成物。(1) Heat-activated delayed adhesive obtained by preparing an aqueous dispersion of 10 to 200 parts by weight of a tackifier and 50 to 300 parts by weight of a solid plasticizer to 100 parts by weight of a polymeric material containing a polyurethane resin. 1. A delayed thermal activation adhesive composition, wherein the polyurethane resin has a linear tetramethylene structure in its molecule.
ポリウレタン樹脂が、ポリテトラメチレングリコールを
そのポリオール原料とするポリウレタンである請求項１
記載の熱活性遅延型粘着剤組成物。(2) Claim 1, wherein the polyurethane resin having a linear tetramethylene structure in its molecule is a polyurethane whose polyol raw material is polytetramethylene glycol.
The heat-activated delayed pressure-sensitive adhesive composition described above.
ポリウレタン樹脂が、エチレングリコール、ジエチレン
グリコール、プロピレングリコールもしくは１，６−ヘ
キサンジオールとアジピン酸とのポリエステル型ポリオ
ールをそのポリオール原料とするポリウレタンである請
求項１記載の熱活性遅延型粘着剤組成物。(3) The polyurethane resin having a linear tetramethylene structure in its molecule is a polyurethane whose polyol raw material is ethylene glycol, diethylene glycol, propylene glycol, or a polyester polyol of 1,6-hexanediol and adipic acid. The heat-activated delayed pressure-sensitive adhesive composition according to claim 1.
ン構造を有するポリウレタンと酢酸ビニル系共重合体を
共に含む、請求項１記載の熱活性遅延粘着剤組成物。(4) The heat-activated delayed pressure-sensitive adhesive composition according to claim 1, wherein the polymeric material contains both a polyurethane having a linear tetramethylene structure in its molecule and a vinyl acetate copolymer.
量部に対して粘着付与剤１０〜２００重量部および固体
可塑剤５０〜３００重量部を水性分散体状に調合し、基
材シート上に水性塗工し乾燥して得た熱活性遅延型粘着
シートにおいて、ポリウレタン樹脂がその分子中に直鎖
状テトラメチレン構造を有することを特徴とする熱活性
遅延型粘着シート。(5) Prepare an aqueous dispersion of 10 to 200 parts by weight of a tackifier and 50 to 300 parts by weight of a solid plasticizer to 100 parts by weight of a polymeric material containing a polyurethane resin, and apply the water-based dispersion onto a base sheet. 1. A delayed heat activation adhesive sheet obtained by processing and drying, wherein the polyurethane resin has a linear tetramethylene structure in its molecules.
ポリウレタン樹脂が、ポリテトラメチレングリコールを
そのポリオール原料とするポリウレタンである請求項５
の記載の熱活性遅延型粘着シート。(6) Claim 5, wherein the polyurethane resin having a linear tetramethylene structure in its molecule is a polyurethane using polytetramethylene glycol as its polyol raw material.
A heat-activated delayed adhesive sheet as described in .
ポリウレタン樹脂が、エチレングリコール、ジエチレン
グリコール、プロピレングリコールもしくは１，６−ヘ
キサンジオールとアジピン酸とのポリエステル型ポリオ
ールをそのポリオール原料とするポリウレタンである請
求項５の記載の熱活性遅延型粘着シート。(7) The polyurethane resin having a linear tetramethylene structure in its molecule is a polyurethane whose polyol raw material is ethylene glycol, diethylene glycol, propylene glycol, or a polyester type polyol of 1,6-hexanediol and adipic acid. The heat-activated delayed pressure-sensitive adhesive sheet according to claim 5.
ン構造を有するポリウレタンと酢酸ビニル系共重合体を
共に含む、請求項５記載の熱活性遅延型粘着シート。(8) The heat-activated delayed pressure-sensitive adhesive sheet according to claim 5, wherein the polymeric material contains both a polyurethane having a linear tetramethylene structure in its molecule and a vinyl acetate copolymer.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63032419A JPH01207372A (en) | 1988-02-15 | 1988-02-15 | Heat-activated delayed type tacky agent composition and heat-activated delayed type tacky sheet |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63032419A JPH01207372A (en) | 1988-02-15 | 1988-02-15 | Heat-activated delayed type tacky agent composition and heat-activated delayed type tacky sheet |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH01207372A true JPH01207372A (en) | 1989-08-21 |
Family
ID=12358426
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63032419A Pending JPH01207372A (en) | 1988-02-15 | 1988-02-15 | Heat-activated delayed type tacky agent composition and heat-activated delayed type tacky sheet |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH01207372A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5574076A (en) * | 1995-05-03 | 1996-11-12 | National Starch And Chemical Investment Holding Corporation | Sucrose benzoate as a tackifier for water sensitive or biodegradable hot melt adhesives |
| US5583187A (en) * | 1995-05-03 | 1996-12-10 | National Starch And Chemical Investment Holding Corporation | Hot melt adhesives based on hydroxy-functional polyesters |
| US5846474A (en) * | 1992-12-21 | 1998-12-08 | Basf Corporation | Thermoplastic polyurethane with poly(hydroxyl group)-containing resin |
| US5977268A (en) * | 1993-11-08 | 1999-11-02 | Basf Corporation | Thermoplastic polyurethane with poly(hydroxyl group)-containing resin |
| JP2008179681A (en) * | 2007-01-23 | 2008-08-07 | Toho Chem Ind Co Ltd | One-pack type water stop |
| US9653006B2 (en) | 2008-09-17 | 2017-05-16 | Avery Dennison Corporation | Activatable adhesive, labels, and related methods |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61174219A (en) * | 1985-01-25 | 1986-08-05 | バイエル・アクチエンゲゼルシヤフト | Polyester polyurethane containing hydroxyl terminal group and its use as adhesive |
| JPS62240374A (en) * | 1986-04-10 | 1987-10-21 | Mitsubishi Paper Mills Ltd | Thermal activating adhesive sheet and production thereof |
-
1988
- 1988-02-15 JP JP63032419A patent/JPH01207372A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61174219A (en) * | 1985-01-25 | 1986-08-05 | バイエル・アクチエンゲゼルシヤフト | Polyester polyurethane containing hydroxyl terminal group and its use as adhesive |
| JPS62240374A (en) * | 1986-04-10 | 1987-10-21 | Mitsubishi Paper Mills Ltd | Thermal activating adhesive sheet and production thereof |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5846474A (en) * | 1992-12-21 | 1998-12-08 | Basf Corporation | Thermoplastic polyurethane with poly(hydroxyl group)-containing resin |
| US5977268A (en) * | 1993-11-08 | 1999-11-02 | Basf Corporation | Thermoplastic polyurethane with poly(hydroxyl group)-containing resin |
| US5574076A (en) * | 1995-05-03 | 1996-11-12 | National Starch And Chemical Investment Holding Corporation | Sucrose benzoate as a tackifier for water sensitive or biodegradable hot melt adhesives |
| US5583187A (en) * | 1995-05-03 | 1996-12-10 | National Starch And Chemical Investment Holding Corporation | Hot melt adhesives based on hydroxy-functional polyesters |
| JP2008179681A (en) * | 2007-01-23 | 2008-08-07 | Toho Chem Ind Co Ltd | One-pack type water stop |
| US9653006B2 (en) | 2008-09-17 | 2017-05-16 | Avery Dennison Corporation | Activatable adhesive, labels, and related methods |
| US10140891B2 (en) | 2008-09-17 | 2018-11-27 | Avery Dennison Corporation | Activatable adhesive, labels, and related methods |
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