CA2302336C - Release coating for adhesive articles and method - Google Patents
Release coating for adhesive articles and method Download PDFInfo
- Publication number
- CA2302336C CA2302336C CA002302336A CA2302336A CA2302336C CA 2302336 C CA2302336 C CA 2302336C CA 002302336 A CA002302336 A CA 002302336A CA 2302336 A CA2302336 A CA 2302336A CA 2302336 C CA2302336 C CA 2302336C
- Authority
- CA
- Canada
- Prior art keywords
- group
- polymer
- water solubilizing
- release coating
- coating composition
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
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- 238000000034 method Methods 0.000 title claims description 27
- 238000000576 coating method Methods 0.000 title description 57
- 239000011248 coating agent Substances 0.000 title description 44
- 239000000853 adhesive Substances 0.000 title description 23
- 230000001070 adhesive effect Effects 0.000 title description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 151
- 229920000642 polymer Polymers 0.000 claims abstract description 129
- 230000003381 solubilizing effect Effects 0.000 claims abstract description 102
- 239000000203 mixture Substances 0.000 claims abstract description 90
- 239000008199 coating composition Substances 0.000 claims abstract description 66
- 150000002430 hydrocarbons Chemical group 0.000 claims abstract description 53
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 41
- 239000006185 dispersion Substances 0.000 claims abstract description 36
- 125000001424 substituent group Chemical group 0.000 claims abstract description 28
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims abstract description 26
- 239000003960 organic solvent Substances 0.000 claims abstract description 26
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 23
- 239000001301 oxygen Substances 0.000 claims abstract description 23
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 23
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000005977 Ethylene Substances 0.000 claims abstract description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 18
- 125000001931 aliphatic group Chemical group 0.000 claims description 42
- 150000001875 compounds Chemical class 0.000 claims description 42
- 239000004820 Pressure-sensitive adhesive Substances 0.000 claims description 40
- 125000000217 alkyl group Chemical group 0.000 claims description 32
- 229920002554 vinyl polymer Polymers 0.000 claims description 29
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 28
- -1 polyethylene backbone Polymers 0.000 claims description 27
- 229930195733 hydrocarbon Natural products 0.000 claims description 26
- 239000001257 hydrogen Substances 0.000 claims description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims description 25
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
- 239000012948 isocyanate Substances 0.000 claims description 24
- 150000002513 isocyanates Chemical class 0.000 claims description 21
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 21
- 239000004215 Carbon black (E152) Substances 0.000 claims description 20
- 229920002689 polyvinyl acetate Polymers 0.000 claims description 20
- 239000011118 polyvinyl acetate Substances 0.000 claims description 20
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 16
- 239000000654 additive Substances 0.000 claims description 15
- 150000001450 anions Chemical class 0.000 claims description 14
- 150000001768 cations Chemical class 0.000 claims description 14
- 239000000178 monomer Substances 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 125000002947 alkylene group Chemical group 0.000 claims description 13
- 125000000732 arylene group Chemical group 0.000 claims description 13
- 239000004094 surface-active agent Substances 0.000 claims description 13
- 125000004450 alkenylene group Chemical group 0.000 claims description 12
- 150000002148 esters Chemical class 0.000 claims description 12
- 150000004820 halides Chemical class 0.000 claims description 12
- 125000005647 linker group Chemical group 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 10
- 230000002378 acidificating effect Effects 0.000 claims description 9
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 8
- 239000003995 emulsifying agent Substances 0.000 claims description 8
- 239000004606 Fillers/Extenders Substances 0.000 claims description 7
- 230000000996 additive effect Effects 0.000 claims description 7
- 125000000129 anionic group Chemical group 0.000 claims description 6
- 239000002243 precursor Substances 0.000 claims description 6
- 125000004419 alkynylene group Chemical group 0.000 claims description 5
- 229920001567 vinyl ester resin Polymers 0.000 claims description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 4
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 125000005395 methacrylic acid group Chemical group 0.000 claims description 4
- 239000004014 plasticizer Substances 0.000 claims description 4
- 239000004971 Cross linker Substances 0.000 claims description 3
- 239000002318 adhesion promoter Substances 0.000 claims description 3
- 229940121375 antifungal agent Drugs 0.000 claims description 3
- 239000003429 antifungal agent Substances 0.000 claims description 3
- 239000003963 antioxidant agent Substances 0.000 claims description 3
- 230000003078 antioxidant effect Effects 0.000 claims description 3
- 230000003115 biocidal effect Effects 0.000 claims description 3
- 239000003139 biocide Substances 0.000 claims description 3
- 239000003086 colorant Substances 0.000 claims description 3
- 238000005260 corrosion Methods 0.000 claims description 3
- 230000007797 corrosion Effects 0.000 claims description 3
- 239000013530 defoamer Substances 0.000 claims description 3
- 239000003112 inhibitor Substances 0.000 claims description 3
- 239000006254 rheological additive Substances 0.000 claims description 3
- 239000013008 thixotropic agent Substances 0.000 claims description 3
- DQXBYHZEEUGOBF-UHFFFAOYSA-N but-3-enoic acid;ethene Chemical compound C=C.OC(=O)CC=C DQXBYHZEEUGOBF-UHFFFAOYSA-N 0.000 claims 1
- 239000005038 ethylene vinyl acetate Substances 0.000 claims 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 claims 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 31
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
- 239000000463 material Substances 0.000 description 20
- 239000011521 glass Substances 0.000 description 17
- 238000003756 stirring Methods 0.000 description 17
- 229920002451 polyvinyl alcohol Polymers 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000002253 acid Substances 0.000 description 15
- 239000007787 solid Substances 0.000 description 15
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 14
- 229920001577 copolymer Polymers 0.000 description 14
- 239000000047 product Substances 0.000 description 13
- 238000010992 reflux Methods 0.000 description 13
- 239000004372 Polyvinyl alcohol Substances 0.000 description 11
- 230000010354 integration Effects 0.000 description 11
- 238000012360 testing method Methods 0.000 description 11
- 239000002562 thickening agent Substances 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 10
- 239000000758 substrate Substances 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 238000005481 NMR spectroscopy Methods 0.000 description 9
- 239000000839 emulsion Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- QWDQYHPOSSHSAW-UHFFFAOYSA-N 1-isocyanatooctadecane Chemical compound CCCCCCCCCCCCCCCCCCN=C=O QWDQYHPOSSHSAW-UHFFFAOYSA-N 0.000 description 8
- 238000001035 drying Methods 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 230000032683 aging Effects 0.000 description 7
- 238000012986 modification Methods 0.000 description 7
- 230000004048 modification Effects 0.000 description 7
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 6
- VANNPISTIUFMLH-UHFFFAOYSA-N glutaric anhydride Chemical compound O=C1CCCC(=O)O1 VANNPISTIUFMLH-UHFFFAOYSA-N 0.000 description 6
- 230000003301 hydrolyzing effect Effects 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 5
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000008367 deionised water Substances 0.000 description 5
- 229910021641 deionized water Inorganic materials 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 230000001376 precipitating effect Effects 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 5
- 238000010998 test method Methods 0.000 description 5
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 239000011127 biaxially oriented polypropylene Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 239000004816 latex Substances 0.000 description 4
- 229920000126 latex Polymers 0.000 description 4
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 4
- 150000007530 organic bases Chemical class 0.000 description 4
- 238000011084 recovery Methods 0.000 description 4
- 229940014800 succinic anhydride Drugs 0.000 description 4
- 239000003039 volatile agent Substances 0.000 description 4
- 238000010626 work up procedure Methods 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000005909 Kieselgur Substances 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 3
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 3
- 229920006378 biaxially oriented polypropylene Polymers 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 229920002301 cellulose acetate Polymers 0.000 description 3
- 238000010276 construction Methods 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 229920001971 elastomer Polymers 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229920001155 polypropylene Polymers 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- NCYNKWQXFADUOZ-UHFFFAOYSA-N 1,1-dioxo-2,1$l^{6}-benzoxathiol-3-one Chemical compound C1=CC=C2C(=O)OS(=O)(=O)C2=C1 NCYNKWQXFADUOZ-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
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- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
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- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
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- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
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- 238000010533 azeotropic distillation Methods 0.000 description 1
- UKMSUNONTOPOIO-UHFFFAOYSA-M behenate Chemical compound CCCCCCCCCCCCCCCCCCCCCC([O-])=O UKMSUNONTOPOIO-UHFFFAOYSA-M 0.000 description 1
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- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
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- 239000013065 commercial product Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 229960002887 deanol Drugs 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 239000012972 dimethylethanolamine Substances 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000004715 ethylene vinyl alcohol Substances 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000003709 fluoroalkyl group Chemical group 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- RZXDTJIXPSCHCI-UHFFFAOYSA-N hexa-1,5-diene-2,5-diol Chemical compound OC(=C)CCC(O)=C RZXDTJIXPSCHCI-UHFFFAOYSA-N 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 1
- 229940030980 inova Drugs 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229940070765 laurate Drugs 0.000 description 1
- 230000000873 masking effect Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920005547 polycyclic aromatic hydrocarbon Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920006267 polyester film Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920001290 polyvinyl ester Polymers 0.000 description 1
- HPCIWDZYMSZAEZ-UHFFFAOYSA-N prop-2-enyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC=C HPCIWDZYMSZAEZ-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000012429 release testing Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 239000000080 wetting agent 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
- C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
- C08G18/6212—Polymers of alkenylalcohols; Acetals thereof; Oxyalkylation products thereof
-
- 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
- C08G18/08—Processes
- C08G18/0804—Manufacture of polymers containing ionic or ionogenic groups
- C08G18/0819—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups
- C08G18/0823—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups containing carboxylate salt groups or groups forming them
-
- 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
- C08G18/30—Low-molecular-weight compounds
- C08G18/34—Carboxylic acids; Esters thereof with monohydroxyl compounds
- C08G18/341—Dicarboxylic acids, esters of polycarboxylic acids containing two carboxylic acid groups
-
- 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
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/71—Monoisocyanates or monoisothiocyanates
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Paints Or Removers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Adhesive Tapes (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Materials For Medical Uses (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Application Of Or Painting With Fluid Materials (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/934,263 US5990238A (en) | 1997-09-19 | 1997-09-19 | Release coating for adhesive articles and method |
| US08/934,263 | 1997-09-19 | ||
| PCT/US1998/001228 WO1999015568A1 (en) | 1997-09-19 | 1998-01-22 | Release coating for adhesive articles and method |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2302336A1 CA2302336A1 (en) | 1999-04-01 |
| CA2302336C true CA2302336C (en) | 2008-10-28 |
Family
ID=25465259
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002302336A Expired - Fee Related CA2302336C (en) | 1997-09-19 | 1998-01-22 | Release coating for adhesive articles and method |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US5990238A (enExample) |
| EP (1) | EP1021469B1 (enExample) |
| JP (1) | JP4243422B2 (enExample) |
| AU (1) | AU6036098A (enExample) |
| BR (1) | BR9812517A (enExample) |
| CA (1) | CA2302336C (enExample) |
| DE (1) | DE69830324T2 (enExample) |
| ES (1) | ES2241115T3 (enExample) |
| WO (1) | WO1999015568A1 (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3797776B2 (ja) * | 1997-12-09 | 2006-07-19 | 一方社油脂工業株式会社 | エマルション型剥離剤 |
| US6257623B1 (en) * | 2000-01-18 | 2001-07-10 | Rr Donnelley & Sons | Printed publication having integrated bookmarks and method of manufacturing same |
| US6521111B1 (en) | 2000-04-10 | 2003-02-18 | Invitrogen Corporation | Methods and articles for labeling polymer gels |
| US6465081B2 (en) | 2000-04-17 | 2002-10-15 | 3M Innovative Properties Company | Image receptor sheet |
| US6824885B2 (en) * | 2001-09-18 | 2004-11-30 | Toray Plastics (America), Inc. | Releasing thermoplastic film, and method of making |
| CA2367812A1 (en) * | 2002-01-15 | 2003-07-15 | Robert F. Smith | Abrasive article with hydrophilic/lipophilic coating |
| US7524545B2 (en) | 2002-05-16 | 2009-04-28 | 3M Innovative Properties Company | Release coating containing thermoplastic silicone-containing polymer |
| US20050130527A1 (en) * | 2003-12-11 | 2005-06-16 | 3M Innovative Properties Company | UV stabilized fibrous articles and method of making the same |
| US7187286B2 (en) | 2004-03-19 | 2007-03-06 | Applera Corporation | Methods and systems for using RFID in biological field |
| US20080216232A1 (en) * | 2006-04-12 | 2008-09-11 | White Elizabeth A | Patient Repositioning System |
| DE102007033807A1 (de) * | 2007-07-13 | 2009-01-22 | Beiersdorf Ag | Modifizierte Acrylatklebemassen |
| JP7049764B2 (ja) | 2014-03-30 | 2022-04-07 | オムノバ ソリューソンズ インコーポレーティッド | 剥離性を備えた低ｖｏｃポリマー |
| US11112416B2 (en) | 2018-01-30 | 2021-09-07 | Life Technologies Corporation | Instruments, devices and consumables for use in a workflow of a smart molecular analysis system |
| CN115989290B (zh) * | 2020-08-24 | 2025-05-27 | 昕特玛公司 | 用于提供剥离涂层的组合物和方法 |
Family Cites Families (41)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2532011A (en) * | 1946-09-07 | 1950-11-28 | Minnesota Mining & Mfg | Liners and adhesive tapes having low adhesion polyvinyl carbamate coatings |
| BE511062A (enExample) * | 1949-10-27 | |||
| BE541740A (enExample) * | 1954-10-01 | 1900-01-01 | ||
| DE1075772B (de) * | 1955-08-01 | 1960-02-18 | Minnesota Mining And Manufacturing Company, St. Paul, Minn. (V. St. A.) | Klebstreifen mit wenighaftenden Rückseitenüberzügen |
| US2913355A (en) * | 1955-12-27 | 1959-11-17 | Johnson & Johnson | Adhesive tape with low adhesion backsize coating |
| US3051588A (en) * | 1959-04-10 | 1962-08-28 | Johnson & Johnson | Product and method of manufacture |
| US3052566A (en) * | 1959-11-20 | 1962-09-04 | Johnson & Johnson | Pressure sensitive adhesive tape having a release coating of fatty alcohol itaconate |
| US3285771A (en) * | 1962-12-21 | 1966-11-15 | Johnson & Johnson | Permanent attachment pressure sensitive adhesive tape |
| US3342625A (en) * | 1964-08-11 | 1967-09-19 | Norton Co | Maleamic acid-vinyl copolymer release agent for pressure-sensitive adhesive tape |
| US3502497A (en) * | 1964-08-26 | 1970-03-24 | Johnson & Johnson | Pressure-sensitive adhesive product |
| DE1494462A1 (de) * | 1965-12-02 | 1969-12-11 | Henkel & Cie Gmbh | Klebstoffabweisender Oberflaechenueberzug |
| US3475196A (en) * | 1965-12-27 | 1969-10-28 | Borden Inc | Pressure-sensitive tape coated with a release agent |
| US3928690A (en) * | 1974-12-30 | 1975-12-23 | Grace W R & Co | Release coated adhesive tape |
| JPS6017319B2 (ja) * | 1977-12-29 | 1985-05-02 | ソニー株式会社 | 剥離性処理剤 |
| US4342815A (en) * | 1980-03-06 | 1982-08-03 | Permacel | Pressure-sensitive adhesive tape having a release coating |
| US4299741A (en) * | 1980-03-06 | 1981-11-10 | Permacel | Aqueous release coating compositions |
| JPS6050392B2 (ja) * | 1980-09-30 | 1985-11-08 | 日東電工株式会社 | 剥離性被膜形成剤 |
| EP0086406A1 (en) * | 1982-02-02 | 1983-08-24 | Permacel | Release coating compositions |
| JPS6090672A (ja) * | 1983-10-19 | 1985-05-21 | Kanai Hiroyuki | ポリエステル製不織布研摩材 |
| JPS6172071A (ja) * | 1984-09-17 | 1986-04-14 | Yuuhoo Chem Kk | 被覆剤組成物 |
| JPS61126191A (ja) * | 1984-11-22 | 1986-06-13 | Nitto Electric Ind Co Ltd | ３成分系剥離性処理層 |
| JPH0684490B2 (ja) * | 1985-05-15 | 1994-10-26 | ニチバン株式会社 | 再剥離性粘着剤組成物 |
| GB8718987D0 (en) * | 1987-08-11 | 1987-09-16 | Unilever Plc | Agglomerated abrasive material |
| CA2021191A1 (en) * | 1989-07-19 | 1991-01-20 | Kazuo Kodama | Method for production of aqueous dispersion of long-chain alkyl graft polymer and aqueous release agent |
| US5202190A (en) * | 1989-08-14 | 1993-04-13 | Minnesota Mining And Manufacturing Company | Method of making vinyl-silicone copolymers using mercapto functional silicone chain-transfer agents and release coatings made therewith |
| US5032460A (en) * | 1989-08-14 | 1991-07-16 | Minnesota Mining And Manufacturing Company | Method of making vinyl-silicone copolymers using mercapto functional silicone chain-transfer agents and release coatings made therewith |
| US5089336A (en) * | 1989-08-14 | 1992-02-18 | Minnesota Mining And Manufacturing Company | General purpose siloxane release coatings |
| JP2802111B2 (ja) * | 1989-08-30 | 1998-09-24 | 株式会社日本触媒 | 水性剥離剤およびその製造方法 |
| JP2733107B2 (ja) * | 1989-08-30 | 1998-03-30 | 株式会社日本触媒 | 水性剥離剤 |
| JPH0386779A (ja) * | 1989-08-31 | 1991-04-11 | Nippon Shokubai Kagaku Kogyo Co Ltd | 水性剥離剤 |
| JP2802112B2 (ja) * | 1989-08-31 | 1998-09-24 | 株式会社日本触媒 | 水性剥離剤およびその製造方法 |
| CA2037319A1 (en) * | 1990-03-21 | 1991-09-22 | Chi-Ming Tseng | Water-borne acrylic low adhesion backsize and release coating compositions, methods of making the compositions, and sheet materials coated therewith |
| US5225480A (en) * | 1990-03-21 | 1993-07-06 | Minnesota Mining And Manufacturing Company | Water-borne low adhesion backsize and release coating compositions, methods of making the compositions, and sheet materials coated therewith |
| US4973513A (en) * | 1990-04-04 | 1990-11-27 | Minnesota Mining And Manufacturing Company | Process for applying a release coating to a wet nonwoven backing and article |
| FI93649C (fi) * | 1990-10-29 | 1995-05-10 | Neste Oy | Polymeerituote, joka toimii irrokekalvona sen päälle kiinnitettäviä paineherkkiä liimoja sisältäviä pintoja varten |
| AU3327093A (en) * | 1991-12-17 | 1993-07-19 | Mobil Oil Corporation | Plastic release film with textured or non-planar surface |
| US5356706A (en) * | 1992-12-14 | 1994-10-18 | Shores A Andrew | Release coating for adhesive tapes and labels |
| JP3207001B2 (ja) * | 1992-12-24 | 2001-09-10 | 花王株式会社 | 長鎖（メタ）アクリレート系ラテックスおよびその製造法 |
| JP2781124B2 (ja) * | 1993-04-16 | 1998-07-30 | 昭和高分子株式会社 | シリコーン共重合体エマルジョン |
| US5516865A (en) * | 1995-02-03 | 1996-05-14 | Minnesota Mining And Manufacturing Company | Waterborne (meth) acrylic latex polymers for release |
| US5674934A (en) * | 1996-02-23 | 1997-10-07 | The Dow Chemical Company | Reversible and irreversible water-based coatings |
-
1997
- 1997-09-19 US US08/934,263 patent/US5990238A/en not_active Expired - Lifetime
-
1998
- 1998-01-22 EP EP98903643A patent/EP1021469B1/en not_active Expired - Lifetime
- 1998-01-22 AU AU60360/98A patent/AU6036098A/en not_active Abandoned
- 1998-01-22 JP JP2000512870A patent/JP4243422B2/ja not_active Expired - Fee Related
- 1998-01-22 DE DE69830324T patent/DE69830324T2/de not_active Expired - Lifetime
- 1998-01-22 BR BR9812517-6A patent/BR9812517A/pt not_active IP Right Cessation
- 1998-01-22 ES ES98903643T patent/ES2241115T3/es not_active Expired - Lifetime
- 1998-01-22 CA CA002302336A patent/CA2302336C/en not_active Expired - Fee Related
- 1998-01-22 WO PCT/US1998/001228 patent/WO1999015568A1/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| CA2302336A1 (en) | 1999-04-01 |
| US5990238A (en) | 1999-11-23 |
| DE69830324D1 (de) | 2005-06-30 |
| JP4243422B2 (ja) | 2009-03-25 |
| DE69830324T2 (de) | 2006-05-11 |
| BR9812517A (pt) | 2000-07-25 |
| EP1021469A1 (en) | 2000-07-26 |
| AU6036098A (en) | 1999-04-12 |
| EP1021469B1 (en) | 2005-05-25 |
| JP2001517716A (ja) | 2001-10-09 |
| ES2241115T3 (es) | 2005-10-16 |
| WO1999015568A1 (en) | 1999-04-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |