ES2491367A1 - Diurethane compounds, water mark production methods using flexography and corresponding compositions and uses - Google Patents
Diurethane compounds, water mark production methods using flexography and corresponding compositions and uses Download PDFInfo
- Publication number
- ES2491367A1 ES2491367A1 ES201330304A ES201330304A ES2491367A1 ES 2491367 A1 ES2491367 A1 ES 2491367A1 ES 201330304 A ES201330304 A ES 201330304A ES 201330304 A ES201330304 A ES 201330304A ES 2491367 A1 ES2491367 A1 ES 2491367A1
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- Prior art keywords
- tmdi
- etilhexanol
- migra
- okay
- peg400
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title abstract description 16
- 239000000203 mixture Substances 0.000 title abstract 5
- 150000001875 compounds Chemical class 0.000 title abstract 4
- 238000007647 flexography Methods 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 abstract description 43
- 238000007639 printing Methods 0.000 abstract description 3
- 239000002904 solvent Substances 0.000 abstract description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 abstract 3
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 abstract 2
- 239000002202 Polyethylene glycol Substances 0.000 abstract 2
- 229920001223 polyethylene glycol Polymers 0.000 abstract 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 abstract 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 abstract 1
- 229920002678 cellulose Polymers 0.000 abstract 1
- 239000001913 cellulose Substances 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 abstract 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 abstract 1
- 235000013772 propylene glycol Nutrition 0.000 abstract 1
- -1 trimethyl-hexamethylene Chemical group 0.000 abstract 1
- PMHURSZHKKJGBM-UHFFFAOYSA-N isoxaben Chemical compound O1N=C(C(C)(CC)CC)C=C1NC(=O)C1=C(OC)C=CC=C1OC PMHURSZHKKJGBM-UHFFFAOYSA-N 0.000 description 18
- 229920002565 Polyethylene Glycol 400 Polymers 0.000 description 13
- 229920002556 Polyethylene Glycol 300 Polymers 0.000 description 9
- 230000035515 penetration Effects 0.000 description 3
- JNUZADQZHYFJGW-JOCHJYFZSA-N (2R)-N-[3-[5-fluoro-2-(2-fluoro-3-methylsulfonylanilino)pyrimidin-4-yl]-1H-indol-7-yl]-3-methoxy-2-(4-methylpiperazin-1-yl)propanamide Chemical compound FC=1C(=NC(=NC=1)NC1=C(C(=CC=C1)S(=O)(=O)C)F)C1=CNC2=C(C=CC=C12)NC([C@@H](COC)N1CCN(CC1)C)=O JNUZADQZHYFJGW-JOCHJYFZSA-N 0.000 description 2
- KEEKMOIRJUWKNK-CABZTGNLSA-N (2S)-2-[[2-[(4R)-4-(difluoromethyl)-2-oxo-1,3-thiazolidin-3-yl]-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]amino]propanamide Chemical compound FC([C@H]1N(C(SC1)=O)C=1N=C2N(CCOC3=C2C=CC(=C3)N[C@H](C(=O)N)C)C=1)F KEEKMOIRJUWKNK-CABZTGNLSA-N 0.000 description 2
- DNBCBAXDWNDRNO-FOSCPWQOSA-N (3aS,6aR)-N-(3-methoxy-1,2,4-thiadiazol-5-yl)-5-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrole-2-carboxamide Chemical compound COC1=NSC(NC(=O)N2C[C@H]3CC(C[C@H]3C2)N(C)C=2C=3C=CNC=3N=CN=2)=N1 DNBCBAXDWNDRNO-FOSCPWQOSA-N 0.000 description 2
- RZUOCXOYPYGSKL-GOSISDBHSA-N 1-[(1s)-1-(4-chloro-3-fluorophenyl)-2-hydroxyethyl]-4-[2-[(2-methylpyrazol-3-yl)amino]pyrimidin-4-yl]pyridin-2-one Chemical compound CN1N=CC=C1NC1=NC=CC(C2=CC(=O)N([C@H](CO)C=3C=C(F)C(Cl)=CC=3)C=C2)=N1 RZUOCXOYPYGSKL-GOSISDBHSA-N 0.000 description 2
- CPYTVBALBFSXSH-UHFFFAOYSA-N 2,6-difluoro-n-[1-[[4-hydroxy-2-(trifluoromethyl)phenyl]methyl]pyrazol-3-yl]benzamide Chemical compound FC(F)(F)C1=CC(O)=CC=C1CN1N=C(NC(=O)C=2C(=CC=CC=2F)F)C=C1 CPYTVBALBFSXSH-UHFFFAOYSA-N 0.000 description 2
- KJUCPVIVNLPLEE-UHFFFAOYSA-N 2,6-difluoro-n-[2-fluoro-5-[5-[2-[(6-morpholin-4-ylpyridin-3-yl)amino]pyrimidin-4-yl]-2-propan-2-yl-1,3-thiazol-4-yl]phenyl]benzenesulfonamide Chemical compound S1C(C(C)C)=NC(C=2C=C(NS(=O)(=O)C=3C(=CC=CC=3F)F)C(F)=CC=2)=C1C(N=1)=CC=NC=1NC(C=N1)=CC=C1N1CCOCC1 KJUCPVIVNLPLEE-UHFFFAOYSA-N 0.000 description 2
- SSORSZACHCNXSJ-UHFFFAOYSA-N 2-[2-(3,4-dichlorophenyl)-3-[2-(2-hydroxypropylamino)pyrimidin-4-yl]imidazol-4-yl]acetonitrile Chemical compound ClC=1C=C(C=CC=1Cl)C=1N(C(=CN=1)CC#N)C1=NC(=NC=C1)NCC(C)O SSORSZACHCNXSJ-UHFFFAOYSA-N 0.000 description 2
- KDDPNNXAZURUGP-UHFFFAOYSA-N 2-[2-(3,4-dichlorophenyl)-3-[2-(piperidin-3-ylamino)pyrimidin-4-yl]imidazol-4-yl]acetonitrile Chemical compound ClC=1C=C(C=CC=1Cl)C=1N(C(=CN=1)CC#N)C1=NC(=NC=C1)NC1CNCCC1 KDDPNNXAZURUGP-UHFFFAOYSA-N 0.000 description 2
- DILISPNYIVRDBP-UHFFFAOYSA-N 2-[3-[2-(2-hydroxypropylamino)pyrimidin-4-yl]-2-naphthalen-2-ylimidazol-4-yl]acetonitrile Chemical compound OC(CNC1=NC=CC(=N1)N1C(=NC=C1CC#N)C1=CC2=CC=CC=C2C=C1)C DILISPNYIVRDBP-UHFFFAOYSA-N 0.000 description 2
- TXIPVVLKTCCGPA-UHFFFAOYSA-N 2-[3-[2-[[1-(cyclopropanecarbonyl)piperidin-3-yl]amino]pyrimidin-4-yl]-2-quinolin-2-ylimidazol-4-yl]acetonitrile Chemical compound C1(CC1)C(=O)N1CC(CCC1)NC1=NC=CC(=N1)N1C(=NC=C1CC#N)C1=NC2=CC=CC=C2C=C1 TXIPVVLKTCCGPA-UHFFFAOYSA-N 0.000 description 2
- DWKNOLCXIFYNFV-HSZRJFAPSA-N 2-[[(2r)-1-[1-[(4-chloro-3-methylphenyl)methyl]piperidin-4-yl]-5-oxopyrrolidine-2-carbonyl]amino]-n,n,6-trimethylpyridine-4-carboxamide Chemical compound CN(C)C(=O)C1=CC(C)=NC(NC(=O)[C@@H]2N(C(=O)CC2)C2CCN(CC=3C=C(C)C(Cl)=CC=3)CC2)=C1 DWKNOLCXIFYNFV-HSZRJFAPSA-N 0.000 description 2
- LHASZEBEQGPCFM-CJFMBICVSA-N 2-amino-4-[(1r)-1-[[(6r)-6-[(5-chloro-2-methoxyphenyl)methyl]-7-oxo-3-(phenoxyamino)-5,6-dihydro-2h-1,4-diazepine-1-carbonyl]amino]propyl]benzoic acid Chemical compound C([C@@H]1CNC(CN(C1=O)C(=O)N[C@H](CC)C=1C=C(N)C(C(O)=O)=CC=1)=NOC=1C=CC=CC=1)C1=CC(Cl)=CC=C1OC LHASZEBEQGPCFM-CJFMBICVSA-N 0.000 description 2
- BVGDAZBTIVRTGO-UONOGXRCSA-N 3-[(1r)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]-5-[4-methoxy-6-[(2s)-2-methylpiperazin-1-yl]pyridin-3-yl]pyridin-2-amine Chemical compound C1([C@@H](C)OC=2C(N)=NC=C(C=2)C2=CN=C(C=C2OC)N2[C@H](CNCC2)C)=C(Cl)C=CC(F)=C1Cl BVGDAZBTIVRTGO-UONOGXRCSA-N 0.000 description 2
- HFGHRUCCKVYFKL-UHFFFAOYSA-N 4-ethoxy-2-piperazin-1-yl-7-pyridin-4-yl-5h-pyrimido[5,4-b]indole Chemical compound C1=C2NC=3C(OCC)=NC(N4CCNCC4)=NC=3C2=CC=C1C1=CC=NC=C1 HFGHRUCCKVYFKL-UHFFFAOYSA-N 0.000 description 2
- RSIWALKZYXPAGW-NSHDSACASA-N 6-(3-fluorophenyl)-3-methyl-7-[(1s)-1-(7h-purin-6-ylamino)ethyl]-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound C=1([C@@H](NC=2C=3N=CNC=3N=CN=2)C)N=C2SC=C(C)N2C(=O)C=1C1=CC=CC(F)=C1 RSIWALKZYXPAGW-NSHDSACASA-N 0.000 description 2
- ONPGOSVDVDPBCY-CQSZACIVSA-N 6-amino-5-[(1r)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]-n-[4-(4-methylpiperazine-1-carbonyl)phenyl]pyridazine-3-carboxamide Chemical compound O([C@H](C)C=1C(=C(F)C=CC=1Cl)Cl)C(C(=NN=1)N)=CC=1C(=O)NC(C=C1)=CC=C1C(=O)N1CCN(C)CC1 ONPGOSVDVDPBCY-CQSZACIVSA-N 0.000 description 2
- BWJHJLINOYAPEG-HOTGVXAUSA-N 8-chloro-6-[(6-chloropyridin-3-yl)methyl]-3-[(1S,2S)-2-hydroxycyclopentyl]-7-methyl-2H-1,3-benzoxazin-4-one Chemical compound ClC1=C(C(=CC=2C(N(COC=21)[C@@H]1[C@H](CCC1)O)=O)CC=1C=NC(=CC=1)Cl)C BWJHJLINOYAPEG-HOTGVXAUSA-N 0.000 description 2
- GISRWBROCYNDME-PELMWDNLSA-N F[C@H]1[C@H]([C@H](NC1=O)COC1=NC=CC2=CC(=C(C=C12)OC)C(=O)N)C Chemical compound F[C@H]1[C@H]([C@H](NC1=O)COC1=NC=CC2=CC(=C(C=C12)OC)C(=O)N)C GISRWBROCYNDME-PELMWDNLSA-N 0.000 description 2
- LRULVYSBRWUVGR-FCHUYYIVSA-N GSK2879552 Chemical compound C1=CC(C(=O)O)=CC=C1CN1CCC(CN[C@H]2[C@@H](C2)C=2C=CC=CC=2)CC1 LRULVYSBRWUVGR-FCHUYYIVSA-N 0.000 description 2
- ZBEPMOZEXLGCTF-UHFFFAOYSA-N O=C(C1CC1)N1CCCC(C1)NC1=NC(=CC=N1)N1C(CC#N)=CN=C1C1=CC2=C(OC=C2)C=C1 Chemical compound O=C(C1CC1)N1CCCC(C1)NC1=NC(=CC=N1)N1C(CC#N)=CN=C1C1=CC2=C(OC=C2)C=C1 ZBEPMOZEXLGCTF-UHFFFAOYSA-N 0.000 description 2
- UQONAEXHTGDOIH-AWEZNQCLSA-N O=C(N1CC[C@@H](C1)N1CCCC1=O)C1=CC2=C(NC3(CC3)CCO2)N=C1 Chemical compound O=C(N1CC[C@@H](C1)N1CCCC1=O)C1=CC2=C(NC3(CC3)CCO2)N=C1 UQONAEXHTGDOIH-AWEZNQCLSA-N 0.000 description 2
- ODUIXUGXPFKQLG-QWRGUYRKSA-N [2-(4-chloro-2-fluoroanilino)-5-methyl-1,3-thiazol-4-yl]-[(2s,3s)-2,3-dimethylpiperidin-1-yl]methanone Chemical compound C[C@H]1[C@@H](C)CCCN1C(=O)C1=C(C)SC(NC=2C(=CC(Cl)=CC=2)F)=N1 ODUIXUGXPFKQLG-QWRGUYRKSA-N 0.000 description 2
- 230000005012 migration Effects 0.000 description 2
- 238000013508 migration Methods 0.000 description 2
- VZUGBLTVBZJZOE-KRWDZBQOSA-N n-[3-[(4s)-2-amino-1,4-dimethyl-6-oxo-5h-pyrimidin-4-yl]phenyl]-5-chloropyrimidine-2-carboxamide Chemical compound N1=C(N)N(C)C(=O)C[C@@]1(C)C1=CC=CC(NC(=O)C=2N=CC(Cl)=CN=2)=C1 VZUGBLTVBZJZOE-KRWDZBQOSA-N 0.000 description 2
- XULSCZPZVQIMFM-IPZQJPLYSA-N odevixibat Chemical compound C12=CC(SC)=C(OCC(=O)N[C@@H](C(=O)N[C@@H](CC)C(O)=O)C=3C=CC(O)=CC=3)C=C2S(=O)(=O)NC(CCCC)(CCCC)CN1C1=CC=CC=C1 XULSCZPZVQIMFM-IPZQJPLYSA-N 0.000 description 2
- OEBIHOVSAMBXIB-SJKOYZFVSA-N selitrectinib Chemical compound C[C@@H]1CCC2=NC=C(F)C=C2[C@H]2CCCN2C2=NC3=C(C=NN3C=C2)C(=O)N1 OEBIHOVSAMBXIB-SJKOYZFVSA-N 0.000 description 2
- KMIOJWCYOHBUJS-HAKPAVFJSA-N vorolanib Chemical compound C1N(C(=O)N(C)C)CC[C@@H]1NC(=O)C1=C(C)NC(\C=C/2C3=CC(F)=CC=C3NC\2=O)=C1C KMIOJWCYOHBUJS-HAKPAVFJSA-N 0.000 description 2
- BIIBYWQGRFWQKM-JVVROLKMSA-N (2S)-N-[4-(cyclopropylamino)-3,4-dioxo-1-[(3S)-2-oxopyrrolidin-3-yl]butan-2-yl]-2-[[(E)-3-(2,4-dichlorophenyl)prop-2-enoyl]amino]-4,4-dimethylpentanamide Chemical compound CC(C)(C)C[C@@H](C(NC(C[C@H](CCN1)C1=O)C(C(NC1CC1)=O)=O)=O)NC(/C=C/C(C=CC(Cl)=C1)=C1Cl)=O BIIBYWQGRFWQKM-JVVROLKMSA-N 0.000 description 1
- QIVUCLWGARAQIO-OLIXTKCUSA-N (3s)-n-[(3s,5s,6r)-6-methyl-2-oxo-1-(2,2,2-trifluoroethyl)-5-(2,3,6-trifluorophenyl)piperidin-3-yl]-2-oxospiro[1h-pyrrolo[2,3-b]pyridine-3,6'-5,7-dihydrocyclopenta[b]pyridine]-3'-carboxamide Chemical compound C1([C@H]2[C@H](N(C(=O)[C@@H](NC(=O)C=3C=C4C[C@]5(CC4=NC=3)C3=CC=CN=C3NC5=O)C2)CC(F)(F)F)C)=C(F)C=CC(F)=C1F QIVUCLWGARAQIO-OLIXTKCUSA-N 0.000 description 1
- NYNZQNWKBKUAII-KBXCAEBGSA-N (3s)-n-[5-[(2r)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-3-yl]-3-hydroxypyrrolidine-1-carboxamide Chemical compound C1[C@@H](O)CCN1C(=O)NC1=C2N=C(N3[C@H](CCC3)C=3C(=CC=C(F)C=3)F)C=CN2N=C1 NYNZQNWKBKUAII-KBXCAEBGSA-N 0.000 description 1
- LCFFREMLXLZNHE-GBOLQPHISA-N (e)-2-[(3r)-3-[4-amino-3-(2-fluoro-4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carbonyl]-4-methyl-4-[4-(oxetan-3-yl)piperazin-1-yl]pent-2-enenitrile Chemical compound C12=C(N)N=CN=C2N([C@@H]2CCCN(C2)C(=O)C(/C#N)=C/C(C)(C)N2CCN(CC2)C2COC2)N=C1C(C(=C1)F)=CC=C1OC1=CC=CC=C1 LCFFREMLXLZNHE-GBOLQPHISA-N 0.000 description 1
- BWSQKOKULIALEW-UHFFFAOYSA-N 2-[2-[4-fluoro-3-(trifluoromethyl)phenyl]-3-[2-(piperidin-3-ylamino)pyrimidin-4-yl]imidazol-4-yl]acetonitrile Chemical compound FC1=C(C=C(C=C1)C=1N(C(=CN=1)CC#N)C1=NC(=NC=C1)NC1CNCCC1)C(F)(F)F BWSQKOKULIALEW-UHFFFAOYSA-N 0.000 description 1
- UXHQLGLGLZKHTC-CUNXSJBXSA-N 4-[(3s,3ar)-3-cyclopentyl-7-(4-hydroxypiperidine-1-carbonyl)-3,3a,4,5-tetrahydropyrazolo[3,4-f]quinolin-2-yl]-2-chlorobenzonitrile Chemical compound C1CC(O)CCN1C(=O)C1=CC=C(C=2[C@@H]([C@H](C3CCCC3)N(N=2)C=2C=C(Cl)C(C#N)=CC=2)CC2)C2=N1 UXHQLGLGLZKHTC-CUNXSJBXSA-N 0.000 description 1
- 229920002535 Polyethylene Glycol 1500 Polymers 0.000 description 1
- MCRWZBYTLVCCJJ-DKALBXGISA-N [(1s,3r)-3-[[(3s,4s)-3-methoxyoxan-4-yl]amino]-1-propan-2-ylcyclopentyl]-[(1s,4s)-5-[6-(trifluoromethyl)pyrimidin-4-yl]-2,5-diazabicyclo[2.2.1]heptan-2-yl]methanone Chemical compound C([C@]1(N(C[C@]2([H])C1)C(=O)[C@@]1(C[C@@H](CC1)N[C@@H]1[C@@H](COCC1)OC)C(C)C)[H])N2C1=CC(C(F)(F)F)=NC=N1 MCRWZBYTLVCCJJ-DKALBXGISA-N 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
- VOVZXURTCKPRDQ-CQSZACIVSA-N n-[4-[chloro(difluoro)methoxy]phenyl]-6-[(3r)-3-hydroxypyrrolidin-1-yl]-5-(1h-pyrazol-5-yl)pyridine-3-carboxamide Chemical compound C1[C@H](O)CCN1C1=NC=C(C(=O)NC=2C=CC(OC(F)(F)Cl)=CC=2)C=C1C1=CC=NN1 VOVZXURTCKPRDQ-CQSZACIVSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/12—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/10—Printing inks based on artificial resins
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- 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
- C08G18/2805—Compounds having only one group containing active hydrogen
- C08G18/2815—Monohydroxy compounds
- C08G18/282—Alkanols, cycloalkanols or arylalkanols including terpenealcohols
- C08G18/2825—Alkanols, cycloalkanols or arylalkanols including terpenealcohols having at least 6 carbon atoms
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- 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
- C08G18/2805—Compounds having only one group containing active hydrogen
- C08G18/2815—Monohydroxy compounds
- C08G18/283—Compounds containing ether groups, e.g. oxyalkylated monohydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4833—Polyethers containing oxyethylene units
-
- 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
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/73—Polyisocyanates or polyisothiocyanates acyclic
-
- 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
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
- C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
- C08G18/752—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
- C08G18/753—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group
- C08G18/755—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/04—Polyurethanes
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M3/00—Printing processes to produce particular kinds of printed work, e.g. patterns
- B41M3/10—Watermarks
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Materials Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Printing Plates And Materials Therefor (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Paper (AREA)
Abstract
The invention relates to compounds of formula R1-O-CO-NH-X-NH-CO-O-R2 (I), in which R1 and R2 are, independently, 2-ethylhexanol, polyethylene glycol having a molecular weight of between 200 and 600 or monomethyl ether of polyethylene glycol having a molecular weight of between 400 and 700, and X is trimethyl-hexamethylene. The composition comprises a compound of formula (I) and a solvent from the group containing propylene carbonate, 1,2-propanediol, ethylene glycol, diethylene glycol, dimethyl sulfoxide (DMSO), water and mixtures of same, in which the solvent is at a concentration of less than or equal to 40 wt.-% in relation to the total weight of said composition. Said compounds and compositions are particularly suitable for the production of water marks on cellulose materials using the printing technique known as flexography.
Description
- Ejemplos Examples
- Polímero Disolvente Viscosidad 35ºC Aplicación sobre papel laboratorio Polymer Solvent Viscosity 35ºC Application on laboratory paper
- EJEMPLO-1 EXAMPLE 1
- 2-ETILHEXANOL-TMDI-PEG300 - ALTA NO SE APLICA 2-ETILHEXANOL-TMDI-PEG300 - HIGH DOES NOT APPLY
- EJEMPLO-2 EXAMPLE-2
- 2-ETILHEXANOL-TMDI-TRIETILENGLICOL - MUY ALTA NO SE APLICA 2-ETILHEXANOL-TMDI-TRIETILENGLICOL - VERY HIGH DOES NOT APPLY
- EJEMPLO-3 EXAMPLE-3
- PEG600-TMDI-PEG1500 - SÓLIDO<60º C NO MIGRA PEG600-TMDI-PEG1500 - SOLID <60º C NOT MIGRA
- EJEMPLO-4 EXAMPLE-4
- PEG600-TMDI-2-ETILHEXANOL - ALTA MIGRA MUCHO PEG600-TMDI-2-ETILHEXANOL - HIGH MIGRA MUCH
- EJEMPLO-5 EXAMPLE-5
- PEGmonoMet-TMDI-2-ETILHEXANOL - 49s MIGRA POCO PEGmonoMet-TMDI-2-ETILHEXANOL - 49s LITTLE MIGRA
- EJEMPLO-6 EXAMPLE-6
- 2-ETILHEXANOL-IPDI-2-ETILHEXANOL-TMDI-2-ETILHEXANOL 15%PC - NO SE APLICA (2 FASES) 2-ETILHEXANOL-IPDI-2-ETILHEXANOL-TMDI-2-ETILHEXANOL 15% PC - DOES NOT APPLY (2 PHASES)
- EJEMPLO-7 EXAMPLE-7
- 2-ETILHEXANOL-IPDI-2-ETILHEXANOL-TMDI-2-ETILHEXANOL 15% 1,2-PROPANODIOL 1min27s MIGRA POCO 2-ETILHEXANOL-IPDI-2-ETILHEXANOL-TMDI-2-ETILHEXANOL 15% 1,2-PROPANODIOL 1min27s LITTLE MIGRA
- EJEMPLO-8 EXAMPLE-8
- 2-ETILHEXANOL-IPDI-2-ETILHEXANOL-TMDI-2-ETILHEXANOL 15% DMSO 1min42s MIGRA POCO 2-ETILHEXANOL-IPDI-2-ETILHEXANOL-TMDI-2-ETILHEXANOL 15% DMSO 1min42s LITTLE MIGRA
- EJEMPLO-9 EXAMPLE-9
- PEGmonoMet-IPDI-2-ETILHEXANOL - ALTA OK PEGmonoMet-IPDI-2-ETILHEXANOL - HIGH okay
- EJEMPLO-10 EXAMPLE-10
- PEG600-IPDI-2-ETILHEXANOL - MUY ALTA OK PEG600-IPDI-2-ETILHEXANOL - VERY HIGH okay
- EJEMPLO-11 EXAMPLE-11
- PEG300-TMDI-PEG300 - 9min12s OK PEG300-TMDI-PEG300 - 9min12s okay
- EJEMPLO-12 EXAMPLE-12
- 2-ETILHEXANOL-TMDI-GLYPOL3020-TMDI-PEGmonoMet - ALTA OK 2-ETILHEXANOL-TMDI-GLYPOL3020-TMDI-PEGmonoMet - HIGH okay
- EJEMPLO-13 EXAMPLE-13
- PEG300-TMDI-GLYPOL3020-TMDI-PEG300 - MUY ALTA NO SE APLICA PEG300-TMDI-GLYPOL3020-TMDI-PEG300 - VERY HIGH DOES NOT APPLY
- EJEMPLO-14 EXAMPLE-14
- PEG300-TMDI-GLYPOL3020-TMDI-PEG300 - MUY ALTA NO SE APLICA PEG300-TMDI-GLYPOL3020-TMDI-PEG300 - VERY HIGH DOES NOT APPLY
- EJEMPLO-15 EXAMPLE-15
- PEG400-TMDI-PEG400 - 3min53s OK PEG400-TMDI-PEG400 - 3min53s okay
- EJEMPLO-16 EXAMPLE-16
- 2-ETILHEXANOL-IPDI-2-ETILHEXANOL-TMDI-2-ETILHEXANOL 25% 1,2-PROPANODIOL 1min7s OK 2-ETILHEXANOL-IPDI-2-ETILHEXANOL-TMDI-2-ETILHEXANOL 25% 1,2-PROPANODIOL 1min7s okay
- EJEMPLO-17 EXAMPLE-17
- 2-ETILHEXANOL-IPDI-2-ETILHEXANOL-TMDI-2-ETILHEXANOL 25% DMSO 29s OK 2-ETILHEXANOL-IPDI-2-ETILHEXANOL-TMDI-2-ETILHEXANOL 25% DMSO 29s okay
- EJEMPLO-18 EXAMPLE-18
- PEG300-TMDI-PEG300 25% AGUA 32s OK PEG300-TMDI-PEG300 25% WATER 32s okay
- EJEMPLO-19 EXAMPLE-19
- PEG300-TMDI-PEG300 25% DMSO 45s OK PEG300-TMDI-PEG300 25% DMSO 45s okay
10 10
- EJEMPLO-20 EXAMPLE-20
- 2-ETILHEXANOL-TMDI-GLYPOL3020-TMDI-PEGmonoMet 25% DMSO 59s OK 2-ETILHEXANOL-TMDI-GLYPOL3020-TMDI-PEGmonoMet 25% DMSO 59s okay
- EJEMPLO-21 EXAMPLE-21
- 2-ETILHEXANOL-TMDI-GLYPOL3020-TMDI-PEGmonoMet 15%PC - OK 2-ETILHEXANOL-TMDI-GLYPOL3020-TMDI-PEGmonoMet 15% PC - okay
- EJEMPLO-22 EXAMPLE-22
- PEG400-TMDI-PEG400 15%PC - OK PEG400-TMDI-PEG400 15% PC - okay
- EJEMPLO-23 EXAMPLE-23
- PEGmonoMet-TMDI-2-ETILHEXANOL 15%PC - OK PEGmonoMet-TMDI-2-ETILHEXANOL 15% PC - okay
- EJEMPLO-24 EXAMPLE-24
- 2-ETILHEXANOL-IPDI-2-ETILHEXANOL-TMDI-2-ETILHEXANOL 30% 1,2-PROPANODIOL 1min2s OK 2-ETILHEXANOL-IPDI-2-ETILHEXANOL-TMDI-2-ETILHEXANOL 30% 1,2-PROPANODIOL 1min2s okay
- EJEMPLO-25 EXAMPLE-25
- 2-ETILHEXANOL-IPDI-2-ETILHEXANOL-TMDI-2-ETILHEXANOL 30%DMSO 27s OK 2-ETILHEXANOL-IPDI-2-ETILHEXANOL-TMDI-2-ETILHEXANOL 30% DMSO 27s okay
- EJEMPLO-26 EXAMPLE-26
- PEG300-TMDI-PEG300 30%AGUA 30s OK PEG300-TMDI-PEG300 30% WATER 30s okay
- EJEMPLO-27 EXAMPLE-27
- PEG300-TMDI-PEG300 30%DMSO 42s OK PEG300-TMDI-PEG300 30% DMSO 42s okay
- EJEMPLO-28 EXAMPLE-28
- PEG400-TMDI-PEG400 30%AGUA 26s OK PEG400-TMDI-PEG400 30% WATER 26s okay
- EJEMPLO-29 EXAMPLE-29
- PEG400-TMDI-PEG400 30%DMSO 32s OK PEG400-TMDI-PEG400 30% DMSO 32s okay
- EJEMPLO-30 EXAMPLE-30
- PEG400-TMDI-PEG400 5%DMSO, 25%AGUA 28s OK PEG400-TMDI-PEG400 5% DMSO, 25% WATER 28s okay
- EJEMPLO-31 EXAMPLE-31
- PEG400-TMDI-PEG400 10%DMSO, 20%AGUA 29s OK PEG400-TMDI-PEG400 10% DMSO, 20% WATER 29s okay
- EJEMPLO-32 EXAMPLE-32
- PEG300-TMDI-PEG300 15%DMSO, 15%AGUA 27s OK PEG300-TMDI-PEG300 15% DMSO, 15% WATER 27s okay
- EJEMPLO-33 EXAMPLE-33
- PEG400-TMDI-PEG400 15%DMSO, 15%AGUA 28s OK PEG400-TMDI-PEG400 15% DMSO, 15% WATER 28s okay
- EJEMPLO-34 EXAMPLE-34
- PEG400-TMDI-PEG400 32,5%AGUA 22s OK PEG400-TMDI-PEG400 32.5% WATER 22s okay
- EJEMPLO-35 EXAMPLE-35
- PEG400-TMDI-PEG400 35%AGUA 20s OK PEG400-TMDI-PEG400 35% WATER 20s okay
- EJEMPLO-36 EXAMPLE-36
- PEG400-TMDI-PEG400 37,5%AGUA 18s OK PEG400-TMDI-PEG400 37.5% WATER 18s okay
- EJEMPLO-37 EXAMPLE-37
- PEG400-TMDI-PEG400 40%AGUA 18s OK PEG400-TMDI-PEG400 40% WATER 18s okay
- EJEMPLO-38 EXAMPLE-38
- PEG400-TMDI-PEG400 17,54%DMSO, 17,54%AGUA 22s OK PEG400-TMDI-PEG400 17.54% DMSO, 17.54% WATER 22s okay
- EJEMPLO-39 EXAMPLE-39
- PEG400-TMDI-PEG400 20%DMSO, 20%AGUA 18s OK PEG400-TMDI-PEG400 20% DMSO, 20% WATER 18s okay
En la tabla siguiente se muestran los resultados obtenidos de la aplicación sobre papel realizada en una máquina de impresión flexográfica. Los mejores productos serán aquellos que tengan una penetración instantánea, un buen registro y que no presenten migración sobre el papel. The following table shows the results obtained from the application on paper made in a flexographic printing machine. The best products will be those that have an instant penetration, a good record and that do not present migration on paper.
11 eleven
- APLICACIÓN EN MÁQUINA FLEXOGRÁFICA APPLICATION IN FLEXOGRAPHIC MACHINE
- NOMBRE NAME
- PENETRACIÓN PAPEL REGISTRO MIGRACIÓN PENETRATION PENETRATION REGISTRY MIGRATION
- EJEMPLO-5 EXAMPLE-5
- INSTANTÁNEA BUENO LEVE SNAPSHOT GOOD MILD
- EJEMPLO-7 EXAMPLE-7
- RÁPIDA BUENO NO MIGRA QUICK GOOD NOT MIGRA
- EJEMPLO-8 EXAMPLE-8
- RÁPIDA BUENO NO MIGRA QUICK GOOD NOT MIGRA
- EJEMPLO-11 EXAMPLE-11
- RÁPIDA BUENO NO MIGRA QUICK GOOD NOT MIGRA
- EJEMPLO-15 EXAMPLE-15
- RÁPIDA BUENO NO MIGRA QUICK GOOD NOT MIGRA
- EJEMPLO-16 EXAMPLE-16
- INSTANTÁNEA BUENO NO MIGRA SNAPSHOT GOOD NOT MIGRA
- EJEMPLO-17 EXAMPLE-17
- LENTA BUENO LEVE SLOW GOOD MILD
- EJEMPLO-18 EXAMPLE-18
- RÁPIDA BUENO NO MIGRA QUICK GOOD DO NOT MIGRA
- EJEMPLO-19 EXAMPLE-19
- RÁPIDA BUENO NO MIGRA QUICK GOOD NOT MIGRA
- EJEMPLO-20 EXAMPLE-20
- LENTA IREGULAR NO MIGRA SLOW IREGULAR DO NOT MIGRA
- EJEMPLO-21 EXAMPLE-21
- LENTA IREGULAR MIGRA SLOW IREGULAR MIGRA
- EJEMPLO-22 EXAMPLE-22
- INSTANTÁNEA IREGULAR MIGRA SNAPSHOT IREGULAR MIGRA
- EJEMPLO-23 EXAMPLE-23
- INSTANTÁNEA IREGULAR MIGRA SNAPSHOT IREGULAR MIGRA
- EJEMPLO-24 EXAMPLE-24
- INSTANTÁNEA IREGULAR MIGRA SNAPSHOT IREGULAR MIGRA
- EJEMPLO-25 EXAMPLE-25
- INSTANTÁNEA IREGULAR NO MIGRA SNAPSHOT IREGULAR NOT MIGRA
- EJEMPLO-26 EXAMPLE-26
- INSTANTÁNEA IREGULAR NO MIGRA SNAPSHOT IREGULAR NOT MIGRA
- EJEMPLO-27 EXAMPLE-27
- INSTANTÁNEA BUENO NO MIGRA SNAPSHOT GOOD NOT MIGRA
- EJEMPLO-28 EXAMPLE-28
- INSTANTÁNEA BUENO NO MIGRA SNAPSHOT GOOD NOT MIGRA
- EJEMPLO-29 EXAMPLE-29
- INSTANTÁNEA BUENO NO MIGRA SNAPSHOT GOOD NOT MIGRA
- EJEMPLO-32 EXAMPLE-32
- INSTANTÁNEA BUENO NO MIGRA SNAPSHOT GOOD NOT MIGRA
- EJEMPLO-33 EXAMPLE-33
- INSTANTÁNEA BUENO NO MIGRA SNAPSHOT GOOD NOT MIGRA
- EJEMPLO-34 EXAMPLE-34
- INSTANTÁNEA BUENO NO MIGRA SNAPSHOT GOOD NOT MIGRA
- EJEMPLO-35 EXAMPLE-35
- INSTANTÁNEA BUENO NO MIGRA SNAPSHOT GOOD NOT MIGRA
- EJEMPLO-36 EXAMPLE-36
- INSTANTÁNEA BUENO NO MIGRA SNAPSHOT GOOD NOT MIGRA
- EJEMPLO-37 EXAMPLE-37
- INSTANTÁNEA BUENO NO MIGRA SNAPSHOT GOOD NOT MIGRA
- EJEMPLO-38 EXAMPLE-38
- INSTANTÁNEA BUENO NO MIGRA SNAPSHOT GOOD NOT MIGRA
- EJEMPLO-39 EXAMPLE-39
- INSTANTÁNEA BUENO NO MIGRA SNAPSHOT GOOD NOT MIGRA
12 12
Claims (1)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES201330304A ES2491367B1 (en) | 2013-03-04 | 2013-03-04 | Diurethane compounds, manufacturing processes of watermarks by flexography and corresponding compositions and uses |
| PCT/ES2014/070157 WO2014135728A1 (en) | 2013-03-04 | 2014-03-03 | Diurethane compounds, water mark production methods using flexography and corresponding compositions and uses |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES201330304A ES2491367B1 (en) | 2013-03-04 | 2013-03-04 | Diurethane compounds, manufacturing processes of watermarks by flexography and corresponding compositions and uses |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| ES2491367A1 true ES2491367A1 (en) | 2014-09-05 |
| ES2491367B1 ES2491367B1 (en) | 2015-06-24 |
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| ES201330304A Expired - Fee Related ES2491367B1 (en) | 2013-03-04 | 2013-03-04 | Diurethane compounds, manufacturing processes of watermarks by flexography and corresponding compositions and uses |
Country Status (2)
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| ES (1) | ES2491367B1 (en) |
| WO (1) | WO2014135728A1 (en) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6384130B1 (en) * | 1999-12-03 | 2002-05-07 | Bayer Corporation | Liquid, hydrophobic, non-migrating, non-functional polyurethane plasticizers |
| ES2294965A1 (en) * | 2007-05-07 | 2008-04-01 | Antonio Oliva Gurgui | Urethane and oligourethane derivatives and corresponding uses and methods for producing water marks using the offset printing technique |
| ES2386179A1 (en) * | 2012-06-13 | 2012-08-10 | Antonio Oliva Gurgui | Compounds derived from urethanes and oligouretans and procedures for manufacturing brands to water through the offset printing technique and corresponding uses (Machine-translation by Google Translate, not legally binding) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2265300B1 (en) | 2006-07-17 | 2008-02-01 | Antonio Oliva Gurgui | "DERIVATIVES OF POLYURETHANS AND CORRESPONDING USES AND PROCEDURES OF MANUFACTURE OF BRANDS TO WATER". |
-
2013
- 2013-03-04 ES ES201330304A patent/ES2491367B1/en not_active Expired - Fee Related
-
2014
- 2014-03-03 WO PCT/ES2014/070157 patent/WO2014135728A1/en not_active Ceased
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6384130B1 (en) * | 1999-12-03 | 2002-05-07 | Bayer Corporation | Liquid, hydrophobic, non-migrating, non-functional polyurethane plasticizers |
| ES2294965A1 (en) * | 2007-05-07 | 2008-04-01 | Antonio Oliva Gurgui | Urethane and oligourethane derivatives and corresponding uses and methods for producing water marks using the offset printing technique |
| ES2386179A1 (en) * | 2012-06-13 | 2012-08-10 | Antonio Oliva Gurgui | Compounds derived from urethanes and oligouretans and procedures for manufacturing brands to water through the offset printing technique and corresponding uses (Machine-translation by Google Translate, not legally binding) |
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| Publication number | Publication date |
|---|---|
| WO2014135728A1 (en) | 2014-09-12 |
| ES2491367B1 (en) | 2015-06-24 |
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