JPWO2015015529A1 - ポリエステル樹脂、ホットメルト接着剤及びホットメルト接着剤溶液 - Google Patents
ポリエステル樹脂、ホットメルト接着剤及びホットメルト接着剤溶液 Download PDFInfo
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- polyester resin
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- 239000004831 Hot glue Substances 0.000 title claims abstract description 94
- 229920001225 polyester resin Polymers 0.000 title claims abstract description 84
- 239000004645 polyester resin Substances 0.000 title claims abstract description 84
- 150000001732 carboxylic acid derivatives Chemical group 0.000 claims abstract description 33
- 150000005846 sugar alcohols Polymers 0.000 claims abstract description 23
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 12
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical group CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000002253 acid Substances 0.000 claims abstract description 7
- 239000002904 solvent Substances 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical group OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid group Chemical group C(CCCCC(=O)O)(=O)O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 3
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical group OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 3
- TVIDDXQYHWJXFK-UHFFFAOYSA-N dodecanedioic acid Chemical group OC(=O)CCCCCCCCCCC(O)=O TVIDDXQYHWJXFK-UHFFFAOYSA-N 0.000 claims description 3
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical group OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 claims description 3
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical group OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 3
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid group Chemical group C(CCCCCCCCC(=O)O)(=O)O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 claims description 3
- KKEYFWRCBNTPAC-UHFFFAOYSA-N terephthalic acid group Chemical group C(C1=CC=C(C(=O)O)C=C1)(=O)O KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 3
- 239000010410 layer Substances 0.000 description 23
- 238000004220 aggregation Methods 0.000 description 10
- 230000002776 aggregation Effects 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 10
- 239000000203 mixture Substances 0.000 description 9
- 238000001879 gelation Methods 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 239000000463 material Substances 0.000 description 7
- 239000000758 substrate Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- 229920008790 Amorphous Polyethylene terephthalate Polymers 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- -1 alicyclic hydrocarbons Chemical class 0.000 description 5
- 238000005809 transesterification reaction Methods 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 238000006068 polycondensation reaction Methods 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 239000011324 bead Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 239000002216 antistatic agent Substances 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000002981 blocking agent Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000001721 carbon Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 239000011256 inorganic filler Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000012766 organic filler Substances 0.000 description 2
- 239000000123 paper Substances 0.000 description 2
- 239000005011 phenolic resin Substances 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000003825 pressing Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 238000013112 stability test Methods 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical group C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-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
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 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
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical group CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000012790 adhesive layer Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 239000011280 coal tar Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000007766 curtain coating Methods 0.000 description 1
- 238000007607 die coating method Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- IRXRGVFLQOSHOH-UHFFFAOYSA-L dipotassium;oxalate Chemical compound [K+].[K+].[O-]C(=O)C([O-])=O IRXRGVFLQOSHOH-UHFFFAOYSA-L 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 238000007756 gravure coating Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000007719 peel strength test Methods 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-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
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- 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
- C09J167/00—Adhesives based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Adhesives based on derivatives of such polymers
- C09J167/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/16—Dicarboxylic acids and dihydroxy compounds
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/16—Dicarboxylic acids and dihydroxy compounds
- C08G63/18—Dicarboxylic acids and dihydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
- C08G63/181—Acids containing aromatic rings
- C08G63/183—Terephthalic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Polyesters Or Polycarbonates (AREA)
Abstract
Description
前記多価カルボン酸残基が、脂肪族多価カルボン酸残基を50〜80モル%の範囲内の割合で含有し、
前記多価アルコール残基が、プロピレングリコール残基を5〜60モル%の範囲内の割合で含有することを特徴とする。
試験1(初期状態)
調製直後のホットメルト接着剤溶液を、25℃の雰囲気中に1時間放置した。その結果、ホットメルト接着剤溶液内のポリエステル樹脂の凝集及びホットメルト接着剤溶液のゲル化が認められない場合を「3」、ポリエステル樹脂の凝集とホットメルト接着剤溶液のゲル化のうち少なくとも一方が認められた場合を「1」、その中間の状態を「2」と、評価した。その結果を後掲の表に示す。
上記試験1で「3」又は「2」と評価されたホットメルト接着剤溶液を、25℃の雰囲気中に120時間放置した。その結果、ホットメルト接着剤溶液内のポリエステル樹脂の凝集及びホットメルト接着剤溶液のゲル化が認められない場合を「3」、ポリエステル樹脂の凝集とホットメルト接着剤溶液のゲル化のうち少なくとも一方が認められた場合を「1」、その中間の状態を「2」と、評価した。その結果を後掲の表に示す。
上記試験1で「3」又は「2」と評価されたホットメルト接着剤溶液を、5℃の雰囲気中に120時間放置した。その結果、ホットメルト接着剤溶液内のポリエステル樹脂の凝集及びホットメルト接着剤溶液のゲル化が認められない場合を「3」、ポリエステル樹脂の凝集とホットメルト接着剤溶液のゲル化のうち少なくとも一方が認められた場合を「1」、その中間の状態を「2」と、評価した。その結果を後掲の表に示す。
基材としてA−PET(アモルファスポリエチレンテレフタレート)製シートを用意した。この基材の上に、上記安定性試験の試験1で「3」又は「2」と評価されたホットメルト接着剤溶液を、バーコータ−#4を用いて塗布してから、100℃で5分間加熱した。これにより、基材上に厚み約2μmのホットメルト接着層を形成した。
ホットメルト接着層に重ねる部材として、A−PET(アモルファスポリエチレンテレフタレート)製シートを用意した。
ホットメルト接着層に接着される部材として、A−PET(アモルファスポリエチレンテレフタレート)製シートを用意した。
Claims (8)
- 多価カルボン酸残基と多価アルコール残基とを備えるホットメルト接着剤用のポリエステル樹脂であって、
前記多価カルボン酸残基が、脂肪族多価カルボン酸残基を50〜80モル%の範囲内の割合で含有し、
前記多価アルコール残基が、プロピレングリコール残基を5〜60モル%の範囲内の割合で含有することを特徴とするポリエステル樹脂。 - 前記脂肪族多価カルボン酸残基が、二つのエステル結合間に介在する炭素数4〜10の直鎖骨格を備える請求項1に記載のポリエステル樹脂。
- 前記脂肪族多価カルボン酸残基が、アジピン酸残基、セバシン酸残基、及びドデカン二酸残基からなる群から選択される一種以上の基を含有する請求項2に記載のポリエステル樹脂。
- 前記多価カルボン酸残基が、テレフタル酸残基及びイソフタル酸残基のうち少なくとも一方の基を更に含有する請求項1乃至3のいずれか一項に記載のポリエステル樹脂。
- 前記多価アルコール残基が、二つのエステル結合間に介在する炭素数2〜6の直鎖骨格を備えるジアルコール残基を更に含有する請求項1乃至4のいずれか一項に記載のポリエステル樹脂。
- 前記ジアルコール残基が、エチレングリコール残基、1,4−ブタンジオール残基、及び1,6−ヘキサンジオール残基からなる群から選択される一種以上の基を含有する請求項5に記載のポリエステル樹脂。
- 請求項1乃至6のいずれか一項に記載のポリエステル樹脂からなるホットメルト接着剤。
- 請求項1乃至6のいずれか一項に記載のポリエステル樹脂と、溶剤とを含有するホットメルト接着剤溶液。
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PCT/JP2013/004613 WO2015015529A1 (ja) | 2013-07-30 | 2013-07-30 | ポリエステル樹脂、ホットメルト接着剤及びホットメルト接着剤溶液 |
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JPWO2015015529A1 true JPWO2015015529A1 (ja) | 2017-03-02 |
JP6116078B2 JP6116078B2 (ja) | 2017-04-19 |
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Country Status (5)
Country | Link |
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US (1) | US9951258B2 (ja) |
JP (1) | JP6116078B2 (ja) |
KR (1) | KR101825453B1 (ja) |
CA (1) | CA2919445C (ja) |
WO (1) | WO2015015529A1 (ja) |
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WO2015026479A1 (en) | 2013-08-21 | 2015-02-26 | Sun Chemical Corporation | Shrink wrap label coating to facilitate recycling |
US9990865B2 (en) | 2013-08-21 | 2018-06-05 | Sun Chemical Corporation | Shrink wrap label coating to facilitate recycling |
JP6828245B2 (ja) * | 2016-02-10 | 2021-02-10 | 三菱ケミカル株式会社 | ポリエステル樹脂およびポリエステル樹脂の製造方法 |
KR102356309B1 (ko) * | 2017-11-20 | 2022-01-28 | 에스케이케미칼 주식회사 | 열용융 접착제용 폴리에스테르 수지 조성물 |
JP2021008639A (ja) * | 2020-10-30 | 2021-01-28 | 三菱ケミカル株式会社 | ポリエステル樹脂およびポリエステル樹脂の製造方法 |
KR102621143B1 (ko) | 2023-03-07 | 2024-01-03 | 김효열 | 생분해성 점착제 조성물 |
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JPS52155640A (en) * | 1976-06-21 | 1977-12-24 | Minnesota Mining & Mfg | Aqueous dispersion heavy duty hottmelt adhesive |
JP2002003810A (ja) * | 2000-06-21 | 2002-01-09 | Toyobo Co Ltd | 接着剤用難燃性ポリエステル樹脂及びその接着剤 |
JP2005002141A (ja) * | 2003-06-09 | 2005-01-06 | Toyobo Co Ltd | 押し出しラミネートアンカーコート剤用ポリエステル樹脂 |
JP2006206860A (ja) * | 2004-12-27 | 2006-08-10 | Toyobo Co Ltd | ポリエステル樹脂の製造方法 |
JP2008248016A (ja) * | 2007-03-29 | 2008-10-16 | Unitika Ltd | 共重合ポリエステル微粒子およびその製造方法 |
JP2010516847A (ja) * | 2007-01-26 | 2010-05-20 | エボニック デグサ ゲーエムベーハー | 非ハロゲン化溶剤中での良好な溶解性を有する結晶性のコポリエステル及びその使用 |
JP2012211307A (ja) * | 2011-03-24 | 2012-11-01 | Toyobo Co Ltd | バイオマスプラスチック塗料 |
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GB0101994D0 (en) | 2001-01-25 | 2001-03-14 | Dupont Teijin Films Us Ltd | Process for the production of coated polumeric film |
US8389117B2 (en) * | 2008-10-30 | 2013-03-05 | Eastman Chemical Company | Hot melt adhesives for roll-applied labels |
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JPS5239785A (en) * | 1975-09-25 | 1977-03-28 | Sumitomo Chem Co Ltd | Unsaturated polyester resin compositions with low shrinkage |
JPS52155640A (en) * | 1976-06-21 | 1977-12-24 | Minnesota Mining & Mfg | Aqueous dispersion heavy duty hottmelt adhesive |
JP2002003810A (ja) * | 2000-06-21 | 2002-01-09 | Toyobo Co Ltd | 接着剤用難燃性ポリエステル樹脂及びその接着剤 |
JP2005002141A (ja) * | 2003-06-09 | 2005-01-06 | Toyobo Co Ltd | 押し出しラミネートアンカーコート剤用ポリエステル樹脂 |
JP2006206860A (ja) * | 2004-12-27 | 2006-08-10 | Toyobo Co Ltd | ポリエステル樹脂の製造方法 |
JP2010516847A (ja) * | 2007-01-26 | 2010-05-20 | エボニック デグサ ゲーエムベーハー | 非ハロゲン化溶剤中での良好な溶解性を有する結晶性のコポリエステル及びその使用 |
JP2008248016A (ja) * | 2007-03-29 | 2008-10-16 | Unitika Ltd | 共重合ポリエステル微粒子およびその製造方法 |
JP2012211307A (ja) * | 2011-03-24 | 2012-11-01 | Toyobo Co Ltd | バイオマスプラスチック塗料 |
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JP6116078B2 (ja) | 2017-04-19 |
CA2919445C (en) | 2018-06-05 |
WO2015015529A1 (ja) | 2015-02-05 |
KR101825453B1 (ko) | 2018-02-05 |
US20160194533A1 (en) | 2016-07-07 |
KR20160027135A (ko) | 2016-03-09 |
CA2919445A1 (en) | 2015-02-05 |
US9951258B2 (en) | 2018-04-24 |
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