CA2472738C - Radiation-cured, laminated flexible packaging material, and radiation-curable, adhesive composition - Google Patents

Radiation-cured, laminated flexible packaging material, and radiation-curable, adhesive composition Download PDF

Info

Publication number: CA2472738C
Authority: CA; Canada
Prior art keywords: radiation; anhydride; flexible packaging; packaging material; meth
Prior art date: 2002-01-22
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Lifetime

Application number

CA2472738A

Other languages

English (en)

French (fr)

Other versions

CA2472738A1 (en

Inventor

Kevin D. Rea

Stephen C. Lapin

Paul Eugene Snowwhite Jr.

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Arkema France SA

Original Assignee

Ashland Licensing and Intellectual Property LLC

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2002-01-22

Filing date

2003-01-21

Publication date

2010-07-20

2003-01-21 Application filed by Ashland Licensing and Intellectual Property LLC filed Critical Ashland Licensing and Intellectual Property LLC

2003-07-31 Publication of CA2472738A1 publication Critical patent/CA2472738A1/en

2010-07-20 Application granted granted Critical

2010-07-20 Publication of CA2472738C publication Critical patent/CA2472738C/en

2023-01-21 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

239000005021 flexible packaging material Substances 0.000 title claims abstract description 125
239000000203 mixture Substances 0.000 title claims abstract description 60
230000001070 adhesive effect Effects 0.000 title claims description 135
239000000853 adhesive Substances 0.000 title claims description 133
239000000178 monomer Substances 0.000 claims abstract description 99
239000012939 laminating adhesive Substances 0.000 claims abstract description 81
-1 titanate compound Chemical class 0.000 claims abstract description 65
150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 63
235000013305 food Nutrition 0.000 claims abstract description 21
235000013361 beverage Nutrition 0.000 claims abstract description 4
239000010410 layer Substances 0.000 claims description 123
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 64
239000010408 film Substances 0.000 claims description 55
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 47
239000000463 material Substances 0.000 claims description 39
238000000034 method Methods 0.000 claims description 35
229920000098 polyolefin Polymers 0.000 claims description 35
150000008064 anhydrides Chemical class 0.000 claims description 32
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 31
230000008569 process Effects 0.000 claims description 25
238000006243 chemical reaction Methods 0.000 claims description 24
239000005022 packaging material Substances 0.000 claims description 21
238000004806 packaging method and process Methods 0.000 claims description 19
229920000728 polyester Polymers 0.000 claims description 19
239000000047 product Substances 0.000 claims description 18
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 17
150000001875 compounds Chemical class 0.000 claims description 16
238000010894 electron beam technology Methods 0.000 claims description 16
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 11
FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 claims description 11
239000011888 foil Substances 0.000 claims description 11
238000013508 migration Methods 0.000 claims description 11
230000005012 migration Effects 0.000 claims description 11
229940014800 succinic anhydride Drugs 0.000 claims description 11
238000000605 extraction Methods 0.000 claims description 10
OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 9
229920001577 copolymer Polymers 0.000 claims description 9
238000009459 flexible packaging Methods 0.000 claims description 9
239000007788 liquid Substances 0.000 claims description 8
230000005855 radiation Effects 0.000 claims description 8
IHEDBVUTTQXGSJ-UHFFFAOYSA-M 2-[bis(2-oxidoethyl)amino]ethanolate;titanium(4+);hydroxide Chemical compound [OH-].[Ti+4].[O-]CCN(CC[O-])CC[O-] IHEDBVUTTQXGSJ-UHFFFAOYSA-M 0.000 claims description 7
LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims description 7
150000001252 acrylic acid derivatives Chemical class 0.000 claims description 7
239000012790 adhesive layer Substances 0.000 claims description 7
JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims description 7
239000004743 Polypropylene Substances 0.000 claims description 6
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 6
229920001155 polypropylene Polymers 0.000 claims description 6
238000007639 printing Methods 0.000 claims description 6
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 5
239000005977 Ethylene Substances 0.000 claims description 5
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 5
150000004645 aluminates Chemical class 0.000 claims description 5
229910052782 aluminium Inorganic materials 0.000 claims description 5
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 5
FLISWPFVWWWNNP-BQYQJAHWSA-N dihydro-3-(1-octenyl)-2,5-furandione Chemical compound CCCCCC\C=C\C1CC(=O)OC1=O FLISWPFVWWWNNP-BQYQJAHWSA-N 0.000 claims description 5
CERQOIWHTDAKMF-UHFFFAOYSA-M methacrylate group Chemical group C(C(=C)C)(=O)[O-] CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 5
229920002647 polyamide Polymers 0.000 claims description 5
VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 claims description 5
229910052725 zinc Inorganic materials 0.000 claims description 5
239000011701 zinc Substances 0.000 claims description 5
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 4
239000007795 chemical reaction product Substances 0.000 claims description 4
238000002156 mixing Methods 0.000 claims description 4
239000000825 pharmaceutical preparation Substances 0.000 claims description 4
229940127557 pharmaceutical product Drugs 0.000 claims description 4
239000003504 photosensitizing agent Substances 0.000 claims description 4
MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 claims description 3
KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 claims description 3
JPSKCQCQZUGWNM-UHFFFAOYSA-N 2,7-Oxepanedione Chemical compound O=C1CCCCC(=O)O1 JPSKCQCQZUGWNM-UHFFFAOYSA-N 0.000 claims description 3
TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 claims description 3
PAVNZLVXYJDFNR-UHFFFAOYSA-N 3,3-dimethyloxane-2,6-dione Chemical compound CC1(C)CCC(=O)OC1=O PAVNZLVXYJDFNR-UHFFFAOYSA-N 0.000 claims description 3
ACJPFLIEHGFXGP-UHFFFAOYSA-N 3,3-dimethyloxolane-2,5-dione Chemical compound CC1(C)CC(=O)OC1=O ACJPFLIEHGFXGP-UHFFFAOYSA-N 0.000 claims description 3
WVRNUXJQQFPNMN-VAWYXSNFSA-N 3-[(e)-dodec-1-enyl]oxolane-2,5-dione Chemical compound CCCCCCCCCC\C=C\C1CC(=O)OC1=O WVRNUXJQQFPNMN-VAWYXSNFSA-N 0.000 claims description 3
HIJQFTSZBHDYKW-UHFFFAOYSA-N 4,4-dimethyloxane-2,6-dione Chemical compound CC1(C)CC(=O)OC(=O)C1 HIJQFTSZBHDYKW-UHFFFAOYSA-N 0.000 claims description 3
IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 claims description 3
239000004698 Polyethylene Substances 0.000 claims description 3
ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 3
150000001336 alkenes Chemical group 0.000 claims description 3
VANNPISTIUFMLH-UHFFFAOYSA-N glutaric anhydride Chemical compound O=C1CCCC(=O)O1 VANNPISTIUFMLH-UHFFFAOYSA-N 0.000 claims description 3
FLBJFXNAEMSXGL-UHFFFAOYSA-N het anhydride Chemical compound O=C1OC(=O)C2C1C1(Cl)C(Cl)=C(Cl)C2(Cl)C1(Cl)Cl FLBJFXNAEMSXGL-UHFFFAOYSA-N 0.000 claims description 3
XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 claims description 3
229920001519 homopolymer Polymers 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
238000011065 in-situ storage Methods 0.000 claims description 3
KKHUSADXXDNRPW-UHFFFAOYSA-N malonic anhydride Chemical compound O=C1CC(=O)O1 KKHUSADXXDNRPW-UHFFFAOYSA-N 0.000 claims description 3
239000011104 metalized film Substances 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims description 3
229940117969 neopentyl glycol Drugs 0.000 claims description 3
YOURXVGYNVXQKT-UHFFFAOYSA-N oxacycloundecane-2,11-dione Chemical compound O=C1CCCCCCCCC(=O)O1 YOURXVGYNVXQKT-UHFFFAOYSA-N 0.000 claims description 3
LJAGLQVRUZWQGK-UHFFFAOYSA-N oxecane-2,10-dione Chemical compound O=C1CCCCCCCC(=O)O1 LJAGLQVRUZWQGK-UHFFFAOYSA-N 0.000 claims description 3
ZJHUBLNWMCWUOV-UHFFFAOYSA-N oxocane-2,8-dione Chemical compound O=C1CCCCCC(=O)O1 ZJHUBLNWMCWUOV-UHFFFAOYSA-N 0.000 claims description 3
RMIBXGXWMDCYEK-UHFFFAOYSA-N oxonane-2,9-dione Chemical compound O=C1CCCCCCC(=O)O1 RMIBXGXWMDCYEK-UHFFFAOYSA-N 0.000 claims description 3
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 3
229920000573 polyethylene Polymers 0.000 claims description 3
JIYNFFGKZCOPKN-UHFFFAOYSA-N sbb061129 Chemical compound O=C1OC(=O)C2C1C1C=C(C)C2C1 JIYNFFGKZCOPKN-UHFFFAOYSA-N 0.000 claims description 3
AUHHYELHRWCWEZ-UHFFFAOYSA-N tetrachlorophthalic anhydride Chemical compound ClC1=C(Cl)C(Cl)=C2C(=O)OC(=O)C2=C1Cl AUHHYELHRWCWEZ-UHFFFAOYSA-N 0.000 claims description 3
SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 claims description 3
QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 claims description 3
KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 claims description 2
JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims description 2
239000004952 Polyamide Substances 0.000 claims description 2
239000004793 Polystyrene Substances 0.000 claims description 2
230000005540 biological transmission Effects 0.000 claims description 2
229910052751 metal Inorganic materials 0.000 claims description 2
239000002184 metal Substances 0.000 claims description 2
FBUKVWPVBMHYJY-UHFFFAOYSA-N noncarboxylic acid Natural products CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 claims description 2
PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 2
229920002223 polystyrene Polymers 0.000 claims description 2
239000005033 polyvinylidene chloride Substances 0.000 claims description 2
WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims 2
XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims 2
XNFGZQXMDBREDW-FLFKKZLDSA-N [(e)-dodec-2-enoyl] (e)-dodec-2-enoate Chemical group CCCCCCCCC\C=C\C(=O)OC(=O)\C=C\CCCCCCCCC XNFGZQXMDBREDW-FLFKKZLDSA-N 0.000 claims 2
FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims 2
229920006254 polymer film Polymers 0.000 claims 2
229940117958 vinyl acetate Drugs 0.000 claims 2
229920001328 Polyvinylidene chloride Polymers 0.000 claims 1
235000021056 liquid food Nutrition 0.000 claims 1
235000021485 packed food Nutrition 0.000 claims 1
235000021055 solid food Nutrition 0.000 claims 1
238000009281 ultraviolet germicidal irradiation Methods 0.000 claims 1
239000005026 oriented polypropylene Substances 0.000 description 21
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
238000000576 coating method Methods 0.000 description 18
UZDMJPAQQFSMMV-UHFFFAOYSA-N 4-oxo-4-(2-prop-2-enoyloxyethoxy)butanoic acid Chemical compound OC(=O)CCC(=O)OCCOC(=O)C=C UZDMJPAQQFSMMV-UHFFFAOYSA-N 0.000 description 14
238000009472 formulation Methods 0.000 description 13
238000012360 testing method Methods 0.000 description 12
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
239000011248 coating agent Substances 0.000 description 9
238000001723 curing Methods 0.000 description 9
230000032798 delamination Effects 0.000 description 9
229920000092 linear low density polyethylene Polymers 0.000 description 8
239000004707 linear low-density polyethylene Substances 0.000 description 8
230000004888 barrier function Effects 0.000 description 7
230000008901 benefit Effects 0.000 description 7
238000003475 lamination Methods 0.000 description 7
238000007789 sealing Methods 0.000 description 7
239000010936 titanium Substances 0.000 description 7
229910052719 titanium Inorganic materials 0.000 description 6
125000000524 functional group Chemical group 0.000 description 5
239000000976 ink Substances 0.000 description 5
238000012545 processing Methods 0.000 description 5
239000002904 solvent Substances 0.000 description 5
229960004418 trolamine Drugs 0.000 description 5
229940095095 2-hydroxyethyl acrylate Drugs 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 4
239000000654 additive Substances 0.000 description 4
238000001035 drying Methods 0.000 description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
238000012986 modification Methods 0.000 description 4
230000004048 modification Effects 0.000 description 4
230000002829 reductive effect Effects 0.000 description 4
239000000126 substance Substances 0.000 description 4
UYCICMIUKYEYEU-ZHACJKMWSA-N 3-[(e)-dodec-2-enyl]oxolane-2,5-dione Chemical compound CCCCCCCCC\C=C\CC1CC(=O)OC1=O UYCICMIUKYEYEU-ZHACJKMWSA-N 0.000 description 3
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 3
238000007796 conventional method Methods 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
238000010030 laminating Methods 0.000 description 3
239000012785 packaging film Substances 0.000 description 3
229920006280 packaging film Polymers 0.000 description 3
238000011282 treatment Methods 0.000 description 3
229940096522 trimethylolpropane triacrylate Drugs 0.000 description 3
239000012855 volatile organic compound Substances 0.000 description 3
VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 2
229920010126 Linear Low Density Polyethylene (LLDPE) Polymers 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 2
125000005233 alkylalcohol group Chemical group 0.000 description 2
230000009286 beneficial effect Effects 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
239000013522 chelant Substances 0.000 description 2
239000011247 coating layer Substances 0.000 description 2
238000003851 corona treatment Methods 0.000 description 2
VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 2
238000001227 electron beam curing Methods 0.000 description 2
238000005516 engineering process Methods 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
238000013401 experimental design Methods 0.000 description 2
238000001125 extrusion Methods 0.000 description 2
238000011049 filling Methods 0.000 description 2
229920001903 high density polyethylene Polymers 0.000 description 2
239000004700 high-density polyethylene Substances 0.000 description 2
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
229910052753 mercury Inorganic materials 0.000 description 2
238000012856 packing Methods 0.000 description 2
230000035515 penetration Effects 0.000 description 2
239000002985 plastic film Substances 0.000 description 2
229920006255 plastic film Polymers 0.000 description 2
229920002959 polymer blend Polymers 0.000 description 2
AZIQALWHRUQPHV-UHFFFAOYSA-N prop-2-eneperoxoic acid Chemical group OOC(=O)C=C AZIQALWHRUQPHV-UHFFFAOYSA-N 0.000 description 2
230000002441 reversible effect Effects 0.000 description 2
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 2
239000010409 thin film Substances 0.000 description 2
231100000419 toxicity Toxicity 0.000 description 2
230000001988 toxicity Effects 0.000 description 2
JNELGWHKGNBSMD-UHFFFAOYSA-N xanthone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3OC2=C1 JNELGWHKGNBSMD-UHFFFAOYSA-N 0.000 description 2
QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 1
WWMFRKPUQJRNBY-UHFFFAOYSA-N (2,3-dimethoxyphenyl)-phenylmethanone Chemical compound COC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1OC WWMFRKPUQJRNBY-UHFFFAOYSA-N 0.000 description 1
GJZFGDYLJLCGHT-UHFFFAOYSA-N 1,2-diethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=C(CC)C(CC)=CC=C3SC2=C1 GJZFGDYLJLCGHT-UHFFFAOYSA-N 0.000 description 1
QWQFVUQPHUKAMY-UHFFFAOYSA-N 1,2-diphenyl-2-propoxyethanone Chemical compound C=1C=CC=CC=1C(OCCC)C(=O)C1=CC=CC=C1 QWQFVUQPHUKAMY-UHFFFAOYSA-N 0.000 description 1
239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
DLEWDCPFCNLJEY-UHFFFAOYSA-N 1-morpholin-4-ylpropan-1-one Chemical compound CCC(=O)N1CCOCC1 DLEWDCPFCNLJEY-UHFFFAOYSA-N 0.000 description 1
KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 1
XRBWKWGATZNBFW-UHFFFAOYSA-N 2-[2-(2-ethenoxyethoxy)ethoxy]ethanol Chemical compound OCCOCCOCCOC=C XRBWKWGATZNBFW-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
KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-UHFFFAOYSA-N 0.000 description 1
QPXVRLXJHPTCPW-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-(4-propan-2-ylphenyl)propan-1-one Chemical compound CC(C)C1=CC=C(C(=O)C(C)(C)O)C=C1 QPXVRLXJHPTCPW-UHFFFAOYSA-N 0.000 description 1
XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 1
BWLBGMIXKSTLSX-UHFFFAOYSA-N 2-hydroxyisobutyric acid Chemical compound CC(C)(O)C(O)=O BWLBGMIXKSTLSX-UHFFFAOYSA-N 0.000 description 1
RIWRBSMFKVOJMN-UHFFFAOYSA-N 2-methyl-1-phenylpropan-2-ol Chemical compound CC(C)(O)CC1=CC=CC=C1 RIWRBSMFKVOJMN-UHFFFAOYSA-N 0.000 description 1
KTALPKYXQZGAEG-UHFFFAOYSA-N 2-propan-2-ylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C(C)C)=CC=C3SC2=C1 KTALPKYXQZGAEG-UHFFFAOYSA-N 0.000 description 1
CYUZOYPRAQASLN-UHFFFAOYSA-N 3-prop-2-enoyloxypropanoic acid Chemical compound OC(=O)CCOC(=O)C=C CYUZOYPRAQASLN-UHFFFAOYSA-N 0.000 description 1
UGVRJVHOJNYEHR-UHFFFAOYSA-N 4-chlorobenzophenone Chemical compound C1=CC(Cl)=CC=C1C(=O)C1=CC=CC=C1 UGVRJVHOJNYEHR-UHFFFAOYSA-N 0.000 description 1
HMBNQNDUEFFFNZ-UHFFFAOYSA-N 4-ethenoxybutan-1-ol Chemical compound OCCCCOC=C HMBNQNDUEFFFNZ-UHFFFAOYSA-N 0.000 description 1
AIXZBGVLNVRQSS-UHFFFAOYSA-N 5-tert-butyl-2-[5-(5-tert-butyl-1,3-benzoxazol-2-yl)thiophen-2-yl]-1,3-benzoxazole Chemical compound CC(C)(C)C1=CC=C2OC(C3=CC=C(S3)C=3OC4=CC=C(C=C4N=3)C(C)(C)C)=NC2=C1 AIXZBGVLNVRQSS-UHFFFAOYSA-N 0.000 description 1
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
238000003855 Adhesive Lamination Methods 0.000 description 1
239000004971 Cross linker Substances 0.000 description 1
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical group COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
239000004593 Epoxy Substances 0.000 description 1
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
229920000219 Ethylene vinyl alcohol Polymers 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical class OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
OWYWGLHRNBIFJP-UHFFFAOYSA-N Ipazine Chemical compound CCN(CC)C1=NC(Cl)=NC(NC(C)C)=N1 OWYWGLHRNBIFJP-UHFFFAOYSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
229920002732 Polyanhydride Polymers 0.000 description 1
229910000831 Steel Inorganic materials 0.000 description 1
238000003848 UV Light-Curing Methods 0.000 description 1
GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 1
230000001133 acceleration Effects 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
238000007259 addition reaction Methods 0.000 description 1
PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
150000004056 anthraquinones Chemical class 0.000 description 1
230000003254 anti-foaming effect Effects 0.000 description 1
150000004982 aromatic amines Chemical class 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
239000011127 biaxially oriented polypropylene Substances 0.000 description 1
229920006378 biaxially oriented polypropylene Polymers 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
ZLSMCQSGRWNEGX-UHFFFAOYSA-N bis(4-aminophenyl)methanone Chemical compound C1=CC(N)=CC=C1C(=O)C1=CC=C(N)C=C1 ZLSMCQSGRWNEGX-UHFFFAOYSA-N 0.000 description 1
MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
125000002843 carboxylic acid group Chemical group 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000000919 ceramic Substances 0.000 description 1
230000008859 change Effects 0.000 description 1
235000013351 cheese Nutrition 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
239000008199 coating composition Substances 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
238000010276 construction Methods 0.000 description 1
238000011109 contamination Methods 0.000 description 1
238000000151 deposition Methods 0.000 description 1
238000001514 detection method Methods 0.000 description 1
238000011161 development Methods 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000000539 dimer Substances 0.000 description 1
230000000447 dimerizing effect Effects 0.000 description 1
PODOEQVNFJSWIK-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethoxyphenyl)methanone Chemical compound COC1=CC(OC)=CC(OC)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 PODOEQVNFJSWIK-UHFFFAOYSA-N 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
239000003814 drug Substances 0.000 description 1
239000000975 dye Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
239000000284 extract Substances 0.000 description 1
239000000945 filler Substances 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000021554 flavoured beverage Nutrition 0.000 description 1
YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
FGPFYPIGQBDZOP-UHFFFAOYSA-N formyl 2-methylbenzoate;thioxanthen-9-one Chemical compound CC1=CC=CC=C1C(=O)OC=O.C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 FGPFYPIGQBDZOP-UHFFFAOYSA-N 0.000 description 1
239000012634 fragment Substances 0.000 description 1
ZNNLBTZKUZBEKO-UHFFFAOYSA-N glyburide Chemical compound COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)NC2CCCCC2)C=C1 ZNNLBTZKUZBEKO-UHFFFAOYSA-N 0.000 description 1
238000007646 gravure printing Methods 0.000 description 1
229920006158 high molecular weight polymer Polymers 0.000 description 1
238000007654 immersion Methods 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
229910010272 inorganic material Inorganic materials 0.000 description 1
239000011147 inorganic material Substances 0.000 description 1
239000012948 isocyanate Substances 0.000 description 1
150000002513 isocyanates Chemical class 0.000 description 1
230000000670 limiting effect Effects 0.000 description 1
FSPSELPMWGWDRY-UHFFFAOYSA-N m-Methylacetophenone Chemical compound CC(=O)C1=CC=CC(C)=C1 FSPSELPMWGWDRY-UHFFFAOYSA-N 0.000 description 1
150000002688 maleic acid derivatives Chemical class 0.000 description 1
235000013372 meat Nutrition 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
238000001465 metallisation Methods 0.000 description 1
SNVLJLYUUXKWOJ-UHFFFAOYSA-N methylidenecarbene Chemical compound C=[C] SNVLJLYUUXKWOJ-UHFFFAOYSA-N 0.000 description 1
239000007777 multifunctional material Substances 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
239000011368 organic material Substances 0.000 description 1
230000036961 partial effect Effects 0.000 description 1
239000003348 petrochemical agent Substances 0.000 description 1
239000000049 pigment Substances 0.000 description 1
239000000088 plastic resin Substances 0.000 description 1
229920006267 polyester film Polymers 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
239000003505 polymerization initiator Substances 0.000 description 1
229920005862 polyol Polymers 0.000 description 1
150000003077 polyols Chemical class 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000012851 printed packaging material Substances 0.000 description 1
RLJWTAURUFQFJP-UHFFFAOYSA-N propan-2-ol;titanium Chemical compound [Ti].CC(C)O.CC(C)O.CC(C)O.CC(C)O RLJWTAURUFQFJP-UHFFFAOYSA-N 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
238000003847 radiation curing Methods 0.000 description 1
238000011084 recovery Methods 0.000 description 1
239000013557 residual solvent Substances 0.000 description 1
239000012260 resinous material Substances 0.000 description 1
239000005060 rubber Substances 0.000 description 1
239000002356 single layer Substances 0.000 description 1
235000011888 snacks Nutrition 0.000 description 1
239000010959 steel Substances 0.000 description 1
238000003860 storage Methods 0.000 description 1
239000000758 substrate Substances 0.000 description 1
RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical class O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 description 1
238000009864 tensile test Methods 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
238000009966 trimming Methods 0.000 description 1
229920001567 vinyl ester resin Polymers 0.000 description 1
229960000834 vinyl ether Drugs 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 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
- C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82B—NANOSTRUCTURES FORMED BY MANIPULATION OF INDIVIDUAL ATOMS, MOLECULES, OR LIMITED COLLECTIONS OF ATOMS OR MOLECULES AS DISCRETE UNITS; MANUFACTURE OR TREATMENT THEREOF
- B82B3/00—Manufacture or treatment of nanostructures by manipulation of individual atoms or molecules, or limited collections of atoms or molecules as discrete units

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Nanotechnology (AREA)
Crystallography & Structural Chemistry (AREA)
Manufacturing & Machinery (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Chemical Kinetics & Catalysis (AREA)
Health & Medical Sciences (AREA)
Laminated Bodies (AREA)
Adhesives Or Adhesive Processes (AREA)
Wrappers (AREA)
Medical Preparation Storing Or Oral Administration Devices (AREA)
Bag Frames (AREA)

CA2472738A 2002-01-22 2003-01-21 Radiation-cured, laminated flexible packaging material, and radiation-curable, adhesive composition Expired - Lifetime CA2472738C (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US34942902P	2002-01-22	2002-01-22
US60/349,429		2002-01-22
PCT/US2003/001488 WO2003062339A2 (en)	2002-01-22	2003-01-21	Radiation-cured, laminated flexible packaging material, and radiation-curable, adhesive composition

Publications (2)

Publication Number	Publication Date
CA2472738A1 CA2472738A1 (en)	2003-07-31
CA2472738C true CA2472738C (en)	2010-07-20

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Application Number	Title	Priority Date	Filing Date
CA2472738A Expired - Lifetime CA2472738C (en)	2002-01-22	2003-01-21	Radiation-cured, laminated flexible packaging material, and radiation-curable, adhesive composition

Country Status (9)

Country	Link
EP (1)	EP1468058A2 (ja)
JP (2)	JP4841805B2 (ja)
KR (1)	KR100965012B1 (ja)
CN (1)	CN1317349C (ja)
AU (1)	AU2003219669C1 (ja)
BR (1)	BRPI0307034B1 (ja)
CA (1)	CA2472738C (ja)
MX (2)	MXPA04007100A (ja)
WO (1)	WO2003062339A2 (ja)

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6989407B2 (en) *	2004-01-09	2006-01-24	Northwest Coatings, Llc	Radiation curable laminating adhesives based on cycloaliphatic carboxylic acid functional monomers
CN102898972B (zh) *	2012-10-29	2014-09-10	华南理工大学	一种加成型有机硅灌封胶用增粘剂的制备方法
CN106068183A (zh) *	2014-02-12	2016-11-02	能源科学公司	在柔性包装应用中的最终白用作层压粘合剂的方法
EP3167019A1 (en)	2014-07-11	2017-05-17	Dorf Ketal Chemicals (India) Private Limited	Adhesion promoting system, and ink compositions thereof
JP6841629B2 (ja)	2015-10-02	2021-03-10	日東電工株式会社	有機金属化合物含有組成物
JP6786328B2 (ja) *	2015-10-02	2020-11-18	日東電工株式会社	偏光フィルム用硬化型接着剤組成物およびその製造方法、偏光フィルムおよびその製造方法、光学フィルムならびに画像表示装置
WO2017057615A1 (ja) *	2015-10-02	2017-04-06	日東電工株式会社	偏光フィルム用硬化型接着剤組成物およびその製造方法、偏光フィルムおよびその製造方法、光学フィルムならびに画像表示装置
KR102414612B1 (ko)	2015-10-13	2022-07-01	삼성전자주식회사	반도체 소자 및 그 제조 방법
CN106696427B (zh) *	2015-11-17	2018-07-20	江苏真美包装科技有限公司	一种热带型泡罩包装用复合硬片的制备方法
CN108441164A (zh) *	2018-04-17	2018-08-24	中山市康和化工有限公司	一种应用于软包装膜的环保型uv胶水

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5143785A (en) *	1990-08-20	1992-09-01	Minnesota Mining And Manufacturing Company	Cyanate ester adhesives for electronic applications
US5300608A (en) *	1992-03-31	1994-04-05	Loctite Corporation	Process for preparing alkoxy-terminated organosiloxane fluids using organo-lithium reagents
JP2527534B2 (ja) *	1994-06-21	1996-08-28	シャープ株式会社	光メモリ素子
JP3443970B2 (ja) *	1994-09-16	2003-09-08	大日本インキ化学工業株式会社	光重合性樹脂組成物
JP3615070B2 (ja) *	1998-01-08	2005-01-26	信越化学工業株式会社	放射線硬化性シリコーンゴム組成物
US6472056B1 (en) *	1999-07-06	2002-10-29	Northwest Coatings Corp.	Radiation-cured laminate label
WO2001040329A1 (en) *	1999-11-30	2001-06-07	Daicel Chemical Industries, Ltd.	Lowly lactone-modified reactive monomer composition, acrylic polyol resins produced with the same, curable resin compositions and coating compositions
CN1317529A (zh) *	2001-04-02	2001-10-17	广州市鹿山化工材料有限公司	涂覆钢管专用胶粘剂

2003
- 2003-01-21 JP JP2003562208A patent/JP4841805B2/ja not_active Expired - Fee Related
- 2003-01-21 MX MXPA04007100A patent/MXPA04007100A/es active IP Right Grant
- 2003-01-21 AU AU2003219669A patent/AU2003219669C1/en not_active Ceased
- 2003-01-21 CA CA2472738A patent/CA2472738C/en not_active Expired - Lifetime
- 2003-01-21 KR KR1020047011185A patent/KR100965012B1/ko not_active Expired - Fee Related
- 2003-01-21 WO PCT/US2003/001488 patent/WO2003062339A2/en not_active Ceased
- 2003-01-21 MX MX2011006189A patent/MX340465B/es unknown
- 2003-01-21 CN CNB038025965A patent/CN1317349C/zh not_active Expired - Fee Related
- 2003-01-21 BR BRPI0307034A patent/BRPI0307034B1/pt not_active IP Right Cessation
- 2003-01-21 EP EP03715938A patent/EP1468058A2/en not_active Withdrawn
2011
- 2011-05-06 JP JP2011103745A patent/JP5449253B2/ja not_active Expired - Fee Related

Also Published As

Publication number	Publication date
CN1317349C (zh)	2007-05-23
EP1468058A2 (en)	2004-10-20
KR100965012B1 (ko)	2010-06-21
MX340465B (es)	2016-07-08
WO2003062339A2 (en)	2003-07-31
JP2011153322A (ja)	2011-08-11
CN1620489A (zh)	2005-05-25
KR20040083090A (ko)	2004-09-30
AU2003219669B2 (en)	2008-09-04
CA2472738A1 (en)	2003-07-31
MXPA04007100A (es)	2005-05-16
JP4841805B2 (ja)	2011-12-21
JP2005515292A (ja)	2005-05-26
AU2003219669C1 (en)	2009-03-26
BR0307034A (pt)	2004-10-26
WO2003062339A3 (en)	2004-04-15
BRPI0307034B1 (pt)	2015-12-08
JP5449253B2 (ja)	2014-03-19

Legal Events

Date	Code	Title	Description
2007-02-07	EEER	Examination request
2023-03-27	MKEX	Expiry	Effective date: 20230123

Publication	Publication Date	Title
US7294658B2 (en)	2007-11-13	Radiation-cured, laminated flexible packaging material and radiation-curable, adhesive composition
JP5449253B2 (ja)	2014-03-19	放射線硬化積層柔軟包装材及び放射線硬化性接着剤組成物
US6720050B2 (en)	2004-04-13	Radiation-cured, laminated flexible packaging material
AU2005204667B2 (en)	2010-06-03	Radiation curable laminating adhesives based on cycloaliphatic carboxylic acid functional monomers
JP4788836B2 (ja)	2011-10-05	水系重合性単量体組成物から形成されたガスバリア性フィルム及び該フィルムの製造方法
EP1736519A1 (en)	2006-12-27	Improved radiation-curable laminating adhesives
AU2003219669A1 (en)	2003-09-18	Radiation-cured, laminated flexible packaging material, and radiation-curable, adhesive composition
JPH08253736A (ja)	1996-10-01	活性エネルギー線硬化型接着剤組成物、該組成物を用いるラミネートフィルムの形成方法およびラミネートフィルム
JPH05156212A (ja)	1993-06-22	接着剤及び該接着剤による積層体の製造方法
TWI794339B (zh)	2023-03-01	用於非極性基材之黏著促進化合物