CA1093243A - Polyurethane printing composition - Google Patents
Polyurethane printing compositionInfo
- Publication number
- CA1093243A CA1093243A CA259,634A CA259634A CA1093243A CA 1093243 A CA1093243 A CA 1093243A CA 259634 A CA259634 A CA 259634A CA 1093243 A CA1093243 A CA 1093243A
- Authority
- CA
- Canada
- Prior art keywords
- composition
- polyetherurethane
- polyether
- percent
- diluent
- 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
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 45
- 239000004814 polyurethane Substances 0.000 title abstract description 11
- 229920002635 polyurethane Polymers 0.000 title abstract description 11
- 239000007788 liquid Substances 0.000 claims abstract description 17
- 239000003085 diluting agent Substances 0.000 claims abstract description 13
- 239000003504 photosensitizing agent Substances 0.000 claims abstract description 7
- 239000003518 caustics Substances 0.000 claims abstract description 5
- 239000007787 solid Substances 0.000 claims abstract description 3
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 30
- 229920000570 polyether Polymers 0.000 claims description 29
- -1 hydroxyalkoxy acrylate Chemical compound 0.000 claims description 15
- 229920005862 polyol Polymers 0.000 claims description 13
- PIZHFBODNLEQBL-UHFFFAOYSA-N 2,2-diethoxy-1-phenylethanone Chemical compound CCOC(OCC)C(=O)C1=CC=CC=C1 PIZHFBODNLEQBL-UHFFFAOYSA-N 0.000 claims description 11
- 150000003077 polyols Chemical class 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 229940063557 methacrylate Drugs 0.000 claims description 9
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 8
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 8
- 239000004698 Polyethylene Substances 0.000 claims description 7
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 7
- 229920000573 polyethylene Polymers 0.000 claims description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- 239000000178 monomer Substances 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 4
- 239000003999 initiator Substances 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 238000006116 polymerization reaction Methods 0.000 claims description 3
- DKEGCUDAFWNSSO-UHFFFAOYSA-N 1,8-dibromooctane Chemical group BrCCCCCCCCBr DKEGCUDAFWNSSO-UHFFFAOYSA-N 0.000 claims description 2
- 125000004386 diacrylate group Chemical group 0.000 claims description 2
- 230000000694 effects Effects 0.000 claims description 2
- 229940048053 acrylate Drugs 0.000 claims 4
- 239000007795 chemical reaction product Substances 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- HLJDOURGTRAFHE-UHFFFAOYSA-N isocyanic acid;3,5,5-trimethylcyclohex-2-en-1-one Chemical compound N=C=O.N=C=O.CC1=CC(=O)CC(C)(C)C1 HLJDOURGTRAFHE-UHFFFAOYSA-N 0.000 claims 1
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 16
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 16
- 229920000642 polymer Polymers 0.000 description 14
- 150000002009 diols Chemical class 0.000 description 11
- 239000000243 solution Substances 0.000 description 8
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 7
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 7
- 239000012948 isocyanate Substances 0.000 description 7
- 150000002513 isocyanates Chemical class 0.000 description 7
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 239000000758 substrate Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 6
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 6
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 239000005642 Oleic acid Substances 0.000 description 6
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 6
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 6
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 6
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 5
- PFANXOISJYKQRP-UHFFFAOYSA-N 2-tert-butyl-4-[1-(5-tert-butyl-4-hydroxy-2-methylphenyl)butyl]-5-methylphenol Chemical compound C=1C(C(C)(C)C)=C(O)C=C(C)C=1C(CCC)C1=CC(C(C)(C)C)=C(O)C=C1C PFANXOISJYKQRP-UHFFFAOYSA-N 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000003599 detergent Substances 0.000 description 5
- 239000002202 Polyethylene glycol Substances 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 125000005442 diisocyanate group Chemical group 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 229940057847 polyethylene glycol 600 Drugs 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000000306 component Substances 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- RBGUKBSLNOTVCD-UHFFFAOYSA-N 1-methylanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C RBGUKBSLNOTVCD-UHFFFAOYSA-N 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 102100026735 Coagulation factor VIII Human genes 0.000 description 2
- GUUVPOWQJOLRAS-UHFFFAOYSA-N Diphenyl disulfide Chemical compound C=1C=CC=CC=1SSC1=CC=CC=C1 GUUVPOWQJOLRAS-UHFFFAOYSA-N 0.000 description 2
- 101000911390 Homo sapiens Coagulation factor VIII Proteins 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229920001983 poloxamer Polymers 0.000 description 2
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000001488 sodium phosphate Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 2
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 2
- 235000019801 trisodium phosphate Nutrition 0.000 description 2
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
- BOCJQSFSGAZAPQ-UHFFFAOYSA-N 1-chloroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2Cl BOCJQSFSGAZAPQ-UHFFFAOYSA-N 0.000 description 1
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 1
- BGJQNPIOBWKQAW-UHFFFAOYSA-N 1-tert-butylanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C(C)(C)C BGJQNPIOBWKQAW-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
- OLVMPQNPFWQNTC-UHFFFAOYSA-N 2-hydroxy-2-phenyl-1-(2-phenylphenyl)ethanone Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1C1=CC=CC=C1 OLVMPQNPFWQNTC-UHFFFAOYSA-N 0.000 description 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
- BQZJOQXSCSZQPS-UHFFFAOYSA-N 2-methoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OC)C(=O)C1=CC=CC=C1 BQZJOQXSCSZQPS-UHFFFAOYSA-N 0.000 description 1
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 description 1
- 101100012544 Bacillus subtilis (strain 168) ylmB gene Proteins 0.000 description 1
- 229920002799 BoPET Polymers 0.000 description 1
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- 239000005041 Mylar™ Substances 0.000 description 1
- RVGRUAULSDPKGF-UHFFFAOYSA-N Poloxamer Chemical compound C1CO1.CC1CO1 RVGRUAULSDPKGF-UHFFFAOYSA-N 0.000 description 1
- 229910021607 Silver chloride Inorganic materials 0.000 description 1
- BGNXCDMCOKJUMV-UHFFFAOYSA-N Tert-Butylhydroquinone Chemical compound CC(C)(C)C1=CC(O)=CC=C1O BGNXCDMCOKJUMV-UHFFFAOYSA-N 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 125000005250 alkyl acrylate group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 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
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 229950011260 betanaphthol Drugs 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000005594 diketone group Chemical group 0.000 description 1
- AUZONCFQVSMFAP-UHFFFAOYSA-N disulfiram Chemical compound CCN(CC)C(=S)SSC(=S)N(CC)CC AUZONCFQVSMFAP-UHFFFAOYSA-N 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Chemical compound CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 125000001145 hydrido group Chemical class *[H] 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 229940086559 methyl benzoin Drugs 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- AYOOGWWGECJQPI-NSHDSACASA-N n-[(1s)-1-(5-fluoropyrimidin-2-yl)ethyl]-3-(3-propan-2-yloxy-1h-pyrazol-5-yl)imidazo[4,5-b]pyridin-5-amine Chemical compound N1C(OC(C)C)=CC(N2C3=NC(N[C@@H](C)C=4N=CC(F)=CN=4)=CC=C3N=C2)=N1 AYOOGWWGECJQPI-NSHDSACASA-N 0.000 description 1
- OPECTNGATDYLSS-UHFFFAOYSA-N naphthalene-2-sulfonyl chloride Chemical compound C1=CC=CC2=CC(S(=O)(=O)Cl)=CC=C21 OPECTNGATDYLSS-UHFFFAOYSA-N 0.000 description 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- NHDHVHZZCFYRSB-UHFFFAOYSA-N pyriproxyfen Chemical compound C=1C=CC=NC=1OC(C)COC(C=C1)=CC=C1OC1=CC=CC=C1 NHDHVHZZCFYRSB-UHFFFAOYSA-N 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 1
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- 101150050634 thiQ gene Proteins 0.000 description 1
- HLCHESOMJVGDSJ-UHFFFAOYSA-N thiq Chemical compound C1=CC(Cl)=CC=C1CC(C(=O)N1CCC(CN2N=CN=C2)(CC1)C1CCCCC1)NC(=O)C1NCC2=CC=CC=C2C1 HLCHESOMJVGDSJ-UHFFFAOYSA-N 0.000 description 1
- 239000012974 tin catalyst Substances 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 125000005289 uranyl group Chemical group 0.000 description 1
- 229910002007 uranyl nitrate Inorganic materials 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F299/00—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers
- C08F299/02—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates
- C08F299/06—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates from polyurethanes
-
- 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
- C08G18/67—Unsaturated compounds having active hydrogen
- C08G18/671—Unsaturated compounds having only one group containing active hydrogen
- C08G18/672—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Polyurethanes Or Polyureas (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polymerisation Methods In General (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/617,883 US4057431A (en) | 1975-09-29 | 1975-09-29 | Ethylenically polyurethane unsaturated composition |
| US617,883 | 1975-09-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1093243A true CA1093243A (en) | 1981-01-06 |
Family
ID=24475430
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA259,634A Expired CA1093243A (en) | 1975-09-29 | 1976-08-23 | Polyurethane printing composition |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4057431A (cg-RX-API-DMAC7.html) |
| JP (1) | JPS5242587A (cg-RX-API-DMAC7.html) |
| AR (1) | AR218615A1 (cg-RX-API-DMAC7.html) |
| AU (1) | AU502604B2 (cg-RX-API-DMAC7.html) |
| BR (1) | BR7606414A (cg-RX-API-DMAC7.html) |
| CA (1) | CA1093243A (cg-RX-API-DMAC7.html) |
| DE (1) | DE2641189A1 (cg-RX-API-DMAC7.html) |
| FR (1) | FR2325690A1 (cg-RX-API-DMAC7.html) |
| GB (1) | GB1507808A (cg-RX-API-DMAC7.html) |
| IT (1) | IT1066188B (cg-RX-API-DMAC7.html) |
| ZA (1) | ZA765077B (cg-RX-API-DMAC7.html) |
Families Citing this family (48)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4057431A (en) * | 1975-09-29 | 1977-11-08 | The Goodyear Tire & Rubber Company | Ethylenically polyurethane unsaturated composition |
| US4234676A (en) * | 1978-01-23 | 1980-11-18 | W. R. Grace & Co. | Polythiol effect curable polymeric composition |
| US4188455A (en) * | 1978-01-03 | 1980-02-12 | Lord Corporation | Actinic radiation-curable formulations containing at least one unsaturated polyether-esterurethane oligomer |
| US4145509A (en) * | 1978-04-21 | 1979-03-20 | Dana Corporation | Polyacrylated polyurethanes and gaskets having sealants thereof |
| CA1122999A (en) * | 1978-05-01 | 1982-05-04 | Alan D. Rousseau | Photopolymerizable composition |
| US4221646A (en) * | 1978-05-01 | 1980-09-09 | The Goodyear Tire & Rubber Company | Treated polyetherurethane photopolymer composition containing triaryl phosphine |
| US4198200A (en) * | 1978-05-18 | 1980-04-15 | Lord Corporation | Damage-preventive coatings |
| US4266007A (en) * | 1978-06-22 | 1981-05-05 | Hercules Incorporated | Multilayer printing plates and process for making same |
| US4230770A (en) * | 1978-10-06 | 1980-10-28 | The Goodyear Tire & Rubber Company | Metal photopolymer substrates |
| DE2854192A1 (de) * | 1978-12-15 | 1980-06-26 | Basf Ag | Polyurethan-beschichtungsmittel |
| US4228232A (en) * | 1979-02-27 | 1980-10-14 | Minnesota Mining And Manufacturing Company | Photopolymerizable composition containing ethylenically unsaturated oligomers |
| US4304923A (en) * | 1979-02-27 | 1981-12-08 | Minnesota Mining And Manufacturing Company | Photopolymerizable oligomer |
| DE2936039A1 (de) * | 1979-09-06 | 1981-04-02 | Bayer Ag, 5090 Leverkusen | Wasserdispergierbare, durch strahlen vernetzbare bindemittel aus urethanacrylaten, ein verfahren zu ihrer herstellung sowie die verwendung dieser bindemittel in waessriger dispersion auf dem anstrich-, druckfarben- und textilsektor |
| US4436806A (en) | 1981-01-16 | 1984-03-13 | W. R. Grace & Co. | Method and apparatus for making printed circuit boards |
| US4451636A (en) * | 1981-01-16 | 1984-05-29 | W. R. Grace & Co. | Polymer composition having terminal alkene and terminal carboxyl groups |
| US4442198A (en) * | 1981-01-16 | 1984-04-10 | W. R. Grace & Co. | Polymer composition having terminal alkene and terminal carboxyl groups |
| US4422914A (en) | 1981-01-16 | 1983-12-27 | W. R. Grace & Co. | Polymer composition having terminal alkene and terminal carboxyl groups |
| US4481281A (en) * | 1981-01-16 | 1984-11-06 | W. R. Grace & Co. | Polymer composition having terminal alkene and terminal carboxyl groups |
| DE3131766A1 (de) * | 1981-08-11 | 1983-02-24 | Basf Ag, 6700 Ludwigshafen | Photopolymerisierbares aufzeichnungsmaterial und verfahren zur herstellung von reliefformen mittels dieses aufzeichnungsmaterials |
| US4634562A (en) * | 1981-09-08 | 1987-01-06 | The Goodyear Tire & Rubber Company | Photocurable polyvinyl chloride composition |
| US4446286A (en) * | 1982-08-02 | 1984-05-01 | The B. F. Goodrich Company | Electron beam curable polyrethane compositions |
| US4631229A (en) * | 1983-06-06 | 1986-12-23 | Minnesota Mining And Manufacturing Company | Article having a coating prepared from radiation curable poly(vinyl chloride) resin composition |
| US4559382A (en) * | 1983-06-06 | 1985-12-17 | Minnesota Mining And Manufacturing Company | Processable radiation curable poly(vinyl chloride) resin compositions |
| DE3328285A1 (de) * | 1983-08-05 | 1985-02-21 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von lichtgehaerteten schichten mit definierter haerte |
| US4780486A (en) * | 1983-10-26 | 1988-10-25 | Dow Corning Corporation | Fast ultraviolet radiation curing silicone composition |
| US5162389A (en) * | 1983-10-26 | 1992-11-10 | Dow Corning Corporation | Fast ultraviolet radiation curing silicone composition having a high refractive index |
| US5124212A (en) * | 1983-10-26 | 1992-06-23 | Dow Corning Corporation | Articles prepared from fast ultraviolet radiation curing silicone composition |
| US4946874A (en) * | 1983-10-26 | 1990-08-07 | Dow Corning Corporation | Fast ultraviolet radiation curing silicone composition containing two vinyl polymers |
| US5169879A (en) * | 1983-10-26 | 1992-12-08 | Dow Corning Corporation | Fast ultraviolet radiation curing silicone composition |
| JPS60191237A (ja) * | 1984-03-13 | 1985-09-28 | Asahi Chem Ind Co Ltd | 露光硬化後非粘着性感光性樹脂組成物 |
| US4607084A (en) * | 1984-06-11 | 1986-08-19 | Celanese Specialty Resins, Inc. | Radiation curable acrylated polyurethane oligomer compositions |
| US4702994A (en) * | 1984-10-01 | 1987-10-27 | W. R. Grace & Co. | Projection imaged relief printing plates |
| US5288571A (en) * | 1986-10-02 | 1994-02-22 | Asahi Kasei Kogyo Kabushiki Kaisha | Photoresin printing plate for use in printing a corrugated board |
| US4816315A (en) * | 1987-02-05 | 1989-03-28 | The Goodyear Tire & Rubber Company | Shaped skin for decorative parts |
| US4874670A (en) * | 1987-11-30 | 1989-10-17 | The Goodyear Tire & Rubber Company | Tire having cured photopolymer air barrier coating |
| US4900763A (en) * | 1988-02-26 | 1990-02-13 | Ciba-Geigy Corporation | Ultraviolet radiation curable vehicles |
| JPH0292915A (ja) * | 1988-09-30 | 1990-04-03 | Sanyo Chem Ind Ltd | 変性ポリウレタン樹脂組成物及び製造法 |
| EP0717320B1 (en) * | 1994-12-13 | 1999-09-08 | MacDermid Imaging Technology Inc. | Soft relief photopolymer printing plates for flexographic printing |
| JPH10513269A (ja) | 1994-12-13 | 1998-12-15 | マクダーミツド イメージング テクノロジー，インコーポレーテツド | 感光性組成物および清浄に稼動する感光性樹脂印刷版 |
| US5753414A (en) * | 1995-10-02 | 1998-05-19 | Macdermid Imaging Technology, Inc. | Photopolymer plate having a peelable substrate |
| US6214522B1 (en) * | 1998-08-28 | 2001-04-10 | Macdermid, Incorporated | Photosensitive resin composition useful in fabricating printing plates |
| US6528553B1 (en) * | 1999-07-20 | 2003-03-04 | Dsm N.V. | Radiation curable resin composition |
| US7309550B2 (en) * | 2004-09-20 | 2007-12-18 | Chemence, Inc. | Photosensitive composition with low yellowing under UV-light and sunlight exposure |
| JP4766886B2 (ja) * | 2005-03-02 | 2011-09-07 | オート化学工業株式会社 | シーリング材上塗り塗料組成物 |
| US20080317957A1 (en) * | 2005-12-20 | 2008-12-25 | Gerardus Cornelis Overbeek | Radiation Curable Composition |
| US8512427B2 (en) | 2011-09-29 | 2013-08-20 | Rohm And Haas Electronic Materials Cmp Holdings, Inc. | Acrylate polyurethane chemical mechanical polishing layer |
| WO2016106062A1 (en) * | 2014-12-23 | 2016-06-30 | Bridgestone Americas Tire Operations, Llc | Actinic radiation curable polymeric mixtures, cured polymeric mixtures and related processes |
| EP3390006B1 (en) | 2015-12-17 | 2021-01-27 | Bridgestone Americas Tire Operations, LLC | Additive manufacturing cartridges and processes for producing cured polymeric products by additive manufacturing |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3028367A (en) * | 1958-04-14 | 1962-04-03 | Rohm & Haas | Copolymers of hydroxyalkyl acrylates and methacrylates and alkyl acrylates and methacrylates reacted with diisocyanates |
| BE592278A (cg-RX-API-DMAC7.html) * | 1959-06-26 | |||
| BE629937A (cg-RX-API-DMAC7.html) * | 1962-03-24 | |||
| US3297745A (en) * | 1962-04-05 | 1967-01-10 | Robertson Co H H | Ethylenically unsaturated di-and tetra-urethane monomers |
| GB1054533A (cg-RX-API-DMAC7.html) * | 1964-06-25 | |||
| US3509234A (en) * | 1965-08-13 | 1970-04-28 | Ford Motor Co | Radiation curable paint binders containing vinyl monomers and a hydroxylated polymer reacted with a polyisocyanate and an hydroxyl alkyl acrylate |
| US3649495A (en) * | 1965-08-31 | 1972-03-14 | Hughes Aircraft Co | Photopolymerization of vinyl monomers using a photo-oxidant dye-triorgano phosphine or arsine catalyst system |
| US3600359A (en) * | 1968-11-21 | 1971-08-17 | Brien Corp O | Novel thiourethane-urethane acrylates |
| US3719638A (en) * | 1969-10-29 | 1973-03-06 | T Miranda | Radiation curable acrylic urethane monomers |
| JPS5034964B1 (cg-RX-API-DMAC7.html) * | 1970-03-30 | 1975-11-12 | ||
| US3694415A (en) * | 1970-07-15 | 1972-09-26 | Kiyoshi Honda | Coating resinous composition |
| US3864133A (en) * | 1970-08-11 | 1975-02-04 | Dainippon Ink & Chemicals | Photo-polymerizable compositions |
| GB1412754A (en) * | 1971-12-29 | 1975-11-05 | Ici Ltd | Photopolymerisable composition |
| US3759809A (en) * | 1972-11-14 | 1973-09-18 | Sun Chemical Corp | Radiation curable compositions comprising an isocyanate modified polyfunctional ester and a photoinitiator |
| GB1467645A (en) * | 1973-01-31 | 1977-03-16 | Sun Chemical Corp | Photoinitiator systems |
| US4057431A (en) * | 1975-09-29 | 1977-11-08 | The Goodyear Tire & Rubber Company | Ethylenically polyurethane unsaturated composition |
-
1975
- 1975-09-29 US US05/617,883 patent/US4057431A/en not_active Expired - Lifetime
-
1976
- 1976-08-23 CA CA259,634A patent/CA1093243A/en not_active Expired
- 1976-08-24 ZA ZA765077A patent/ZA765077B/xx unknown
- 1976-08-30 AU AU17274/76A patent/AU502604B2/en not_active Expired
- 1976-09-13 DE DE19762641189 patent/DE2641189A1/de not_active Withdrawn
- 1976-09-16 GB GB38387/76A patent/GB1507808A/en not_active Expired
- 1976-09-17 IT IT51342/76A patent/IT1066188B/it active
- 1976-09-22 AR AR264802A patent/AR218615A1/es active
- 1976-09-27 BR BR7606414A patent/BR7606414A/pt unknown
- 1976-09-27 JP JP51115700A patent/JPS5242587A/ja active Granted
- 1976-09-29 FR FR7629271A patent/FR2325690A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| FR2325690A1 (fr) | 1977-04-22 |
| US4057431A (en) | 1977-11-08 |
| FR2325690B1 (cg-RX-API-DMAC7.html) | 1981-03-20 |
| BR7606414A (pt) | 1977-06-21 |
| AU502604B2 (en) | 1979-08-02 |
| GB1507808A (en) | 1978-04-19 |
| IT1066188B (it) | 1985-03-04 |
| JPS6211007B2 (cg-RX-API-DMAC7.html) | 1987-03-10 |
| DE2641189A1 (de) | 1977-04-07 |
| JPS5242587A (en) | 1977-04-02 |
| AU1727476A (en) | 1978-03-09 |
| AR218615A1 (es) | 1980-06-30 |
| ZA765077B (en) | 1977-08-31 |
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| MKEX | Expiry |