CA1036756A - Transfer printing process - Google Patents
Transfer printing processInfo
- Publication number
- CA1036756A CA1036756A CA216,540A CA216540A CA1036756A CA 1036756 A CA1036756 A CA 1036756A CA 216540 A CA216540 A CA 216540A CA 1036756 A CA1036756 A CA 1036756A
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- formula
- amino
- dyestuff
- ethyl
- 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
- 238000010023 transfer printing Methods 0.000 title claims abstract description 6
- 238000000034 method Methods 0.000 title claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
- 125000001424 substituent group Chemical group 0.000 claims abstract description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 7
- 239000000463 material Substances 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 239000000835 fiber Substances 0.000 claims abstract description 3
- 230000002209 hydrophobic effect Effects 0.000 claims abstract description 3
- 239000000975 dye Substances 0.000 claims description 16
- 238000007639 printing Methods 0.000 claims description 13
- -1 sulpho groups Chemical group 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000000976 ink Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- 238000005859 coupling reaction Methods 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 239000004753 textile Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Substances ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 238000007646 gravure printing Methods 0.000 description 3
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Substances [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 2
- 229920002284 Cellulose triacetate Polymers 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000001856 Ethyl cellulose Substances 0.000 description 2
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- 150000001989 diazonium salts Chemical class 0.000 description 2
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 229920001249 ethyl cellulose Polymers 0.000 description 2
- 235000019325 ethyl cellulose Nutrition 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000001117 sulphuric acid Substances 0.000 description 2
- 235000011149 sulphuric acid Nutrition 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- QIDUETMNCXXNKY-UHFFFAOYSA-N 2,4,6-tris(trifluoromethyl)aniline Chemical compound NC1=C(C(F)(F)F)C=C(C(F)(F)F)C=C1C(F)(F)F QIDUETMNCXXNKY-UHFFFAOYSA-N 0.000 description 1
- UIWVOUBVGBJRNP-UHFFFAOYSA-N 2,4-bis(trifluoromethyl)aniline Chemical compound NC1=CC=C(C(F)(F)F)C=C1C(F)(F)F UIWVOUBVGBJRNP-UHFFFAOYSA-N 0.000 description 1
- VBXPHDBFAZDZOB-UHFFFAOYSA-N 2,4-dinitro-6-(trifluoromethyl)aniline Chemical compound NC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1C(F)(F)F VBXPHDBFAZDZOB-UHFFFAOYSA-N 0.000 description 1
- XWMVIJUAZAEWIE-UHFFFAOYSA-N 2,5-bis(trifluoromethyl)aniline Chemical compound NC1=CC(C(F)(F)F)=CC=C1C(F)(F)F XWMVIJUAZAEWIE-UHFFFAOYSA-N 0.000 description 1
- KEYVECAMLDRXSJ-UHFFFAOYSA-N 2,6-bis(trifluoromethyl)aniline Chemical compound NC1=C(C(F)(F)F)C=CC=C1C(F)(F)F KEYVECAMLDRXSJ-UHFFFAOYSA-N 0.000 description 1
- VACNDKUQVLNNLD-UHFFFAOYSA-N 2,6-dinitro-4-(trifluoromethyl)aniline Chemical compound NC1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O VACNDKUQVLNNLD-UHFFFAOYSA-N 0.000 description 1
- OPFFAOSYJXWUCW-UHFFFAOYSA-N 2-amino-3-nitro-5-(trifluoromethyl)benzonitrile Chemical compound NC1=C(C#N)C=C(C(F)(F)F)C=C1[N+]([O-])=O OPFFAOSYJXWUCW-UHFFFAOYSA-N 0.000 description 1
- QKRJIXSZTKOFTD-UHFFFAOYSA-N 2-bromo-4-(trifluoromethyl)aniline Chemical compound NC1=CC=C(C(F)(F)F)C=C1Br QKRJIXSZTKOFTD-UHFFFAOYSA-N 0.000 description 1
- ALWPXRLPKWZMRF-UHFFFAOYSA-N 2-chloro-n-[3-(diethylamino)-4-methoxyphenyl]acetamide Chemical compound CCN(CC)C1=CC(NC(=O)CCl)=CC=C1OC ALWPXRLPKWZMRF-UHFFFAOYSA-N 0.000 description 1
- PAXQXJDYVORMOO-UHFFFAOYSA-N 2-methyl-4-(trifluoromethyl)aniline Chemical compound CC1=CC(C(F)(F)F)=CC=C1N PAXQXJDYVORMOO-UHFFFAOYSA-N 0.000 description 1
- OGOBINRVCUWLGN-UHFFFAOYSA-N 3-(trifluoromethyl)benzonitrile Chemical compound FC(F)(F)C1=CC=CC(C#N)=C1 OGOBINRVCUWLGN-UHFFFAOYSA-N 0.000 description 1
- SFTBLNXWRAQUHE-UHFFFAOYSA-N 3-methyl-n,n-di(propan-2-yl)aniline Chemical compound CC(C)N(C(C)C)C1=CC=CC(C)=C1 SFTBLNXWRAQUHE-UHFFFAOYSA-N 0.000 description 1
- MWLZJOBGDXBMBP-UHFFFAOYSA-N 4-amino-3-(trifluoromethyl)benzonitrile Chemical compound NC1=CC=C(C#N)C=C1C(F)(F)F MWLZJOBGDXBMBP-UHFFFAOYSA-N 0.000 description 1
- CVINWVPRKDIGLL-UHFFFAOYSA-N 4-chloro-2-(trifluoromethyl)aniline Chemical compound NC1=CC=C(Cl)C=C1C(F)(F)F CVINWVPRKDIGLL-UHFFFAOYSA-N 0.000 description 1
- PLAJILMIMRWOTQ-UHFFFAOYSA-N 4-ethylsulfonyl-2-(trifluoromethyl)aniline Chemical compound CCS(=O)(=O)C1=CC=C(N)C(C(F)(F)F)=C1 PLAJILMIMRWOTQ-UHFFFAOYSA-N 0.000 description 1
- RZMLCRWDGFATCO-UHFFFAOYSA-N 4-nitro-2,6-bis(trifluoromethyl)aniline Chemical compound NC1=C(C(F)(F)F)C=C([N+]([O-])=O)C=C1C(F)(F)F RZMLCRWDGFATCO-UHFFFAOYSA-N 0.000 description 1
- ODGIMMLDVSWADK-UHFFFAOYSA-N 4-trifluoromethylaniline Chemical compound NC1=CC=C(C(F)(F)F)C=C1 ODGIMMLDVSWADK-UHFFFAOYSA-N 0.000 description 1
- PRCZLMXSACDELF-UHFFFAOYSA-N 5-chloro-n,n-diethyl-2-methoxyaniline Chemical compound CCN(CC)C1=CC(Cl)=CC=C1OC PRCZLMXSACDELF-UHFFFAOYSA-N 0.000 description 1
- 229920000298 Cellophane Polymers 0.000 description 1
- 235000013912 Ceratonia siliqua Nutrition 0.000 description 1
- 240000008886 Ceratonia siliqua Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- 230000003139 buffering effect Effects 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 235000011167 hydrochloric acid Nutrition 0.000 description 1
- 229960000443 hydrochloric acid Drugs 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 229960004592 isopropanol Drugs 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- OVSARSKQWCLSJT-UHFFFAOYSA-N n,n-di(propan-2-yl)aniline Chemical compound CC(C)N(C(C)C)C1=CC=CC=C1 OVSARSKQWCLSJT-UHFFFAOYSA-N 0.000 description 1
- ISGXOWLMGOPVPB-UHFFFAOYSA-N n,n-dibenzylaniline Chemical compound C=1C=CC=CC=1CN(C=1C=CC=CC=1)CC1=CC=CC=C1 ISGXOWLMGOPVPB-UHFFFAOYSA-N 0.000 description 1
- MUKJUKMSNRJVBD-UHFFFAOYSA-N n,n-dibutyl-3-methylaniline Chemical compound CCCCN(CCCC)C1=CC=CC(C)=C1 MUKJUKMSNRJVBD-UHFFFAOYSA-N 0.000 description 1
- FZPXKEPZZOEPGX-UHFFFAOYSA-N n,n-dibutylaniline Chemical compound CCCCN(CCCC)C1=CC=CC=C1 FZPXKEPZZOEPGX-UHFFFAOYSA-N 0.000 description 1
- CIPVVROJHKLHJI-UHFFFAOYSA-N n,n-diethyl-3-methylaniline Chemical compound CCN(CC)C1=CC=CC(C)=C1 CIPVVROJHKLHJI-UHFFFAOYSA-N 0.000 description 1
- MMFBQHXDINNBMW-UHFFFAOYSA-N n,n-dipropylaniline Chemical compound CCCN(CCC)C1=CC=CC=C1 MMFBQHXDINNBMW-UHFFFAOYSA-N 0.000 description 1
- MABNHLIMYDDYMP-UHFFFAOYSA-N n-[3-(diethylamino)-4-ethoxyphenyl]acetamide Chemical compound CCOC1=CC=C(NC(C)=O)C=C1N(CC)CC MABNHLIMYDDYMP-UHFFFAOYSA-N 0.000 description 1
- VFEDHLNZINIBNR-UHFFFAOYSA-N n-[3-(diethylamino)-4-phenoxyphenyl]acetamide Chemical compound CCN(CC)C1=CC(NC(C)=O)=CC=C1OC1=CC=CC=C1 VFEDHLNZINIBNR-UHFFFAOYSA-N 0.000 description 1
- VMOVMBPAMMYRHV-UHFFFAOYSA-N n-[3-(diethylamino)-4-phenylmethoxyphenyl]acetamide Chemical compound CCN(CC)C1=CC(NC(C)=O)=CC=C1OCC1=CC=CC=C1 VMOVMBPAMMYRHV-UHFFFAOYSA-N 0.000 description 1
- YQMWHJPUEGBIAJ-UHFFFAOYSA-N n-[3-(diethylamino)-4-propoxyphenyl]acetamide Chemical compound CCCOC1=CC=C(NC(C)=O)C=C1N(CC)CC YQMWHJPUEGBIAJ-UHFFFAOYSA-N 0.000 description 1
- SVIPVFDSQLTSKB-UHFFFAOYSA-N n-[3-(diethylamino)phenyl]formamide Chemical compound CCN(CC)C1=CC=CC(NC=O)=C1 SVIPVFDSQLTSKB-UHFFFAOYSA-N 0.000 description 1
- UPSVCAOHEJFCAL-UHFFFAOYSA-N n-[3-(dimethylamino)phenyl]formamide Chemical compound CN(C)C1=CC=CC(NC=O)=C1 UPSVCAOHEJFCAL-UHFFFAOYSA-N 0.000 description 1
- RUBVZYIEDJJNDG-UHFFFAOYSA-N n-[3-(dimethylamino)phenyl]propanamide Chemical compound CCC(=O)NC1=CC=CC(N(C)C)=C1 RUBVZYIEDJJNDG-UHFFFAOYSA-N 0.000 description 1
- WQGNLSJPWONKIY-UHFFFAOYSA-N n-[3-[cyclohexyl(ethyl)amino]-4-methoxyphenyl]acetamide Chemical compound C=1C(NC(C)=O)=CC=C(OC)C=1N(CC)C1CCCCC1 WQGNLSJPWONKIY-UHFFFAOYSA-N 0.000 description 1
- QROYYWNKSNVUGP-UHFFFAOYSA-N n-benzyl-3-chloro-n-ethylaniline Chemical compound C=1C=CC(Cl)=CC=1N(CC)CC1=CC=CC=C1 QROYYWNKSNVUGP-UHFFFAOYSA-N 0.000 description 1
- DRPFVVZJLZHJJQ-UHFFFAOYSA-N n-benzyl-n-cyclohexylaniline Chemical compound C=1C=CC=CC=1CN(C=1C=CC=CC=1)C1CCCCC1 DRPFVVZJLZHJJQ-UHFFFAOYSA-N 0.000 description 1
- HSZCJVZRHXPCIA-UHFFFAOYSA-N n-benzyl-n-ethylaniline Chemical compound C=1C=CC=CC=1N(CC)CC1=CC=CC=C1 HSZCJVZRHXPCIA-UHFFFAOYSA-N 0.000 description 1
- LXZGVFCKZRHKMU-UHFFFAOYSA-N n-benzyl-n-methylaniline Chemical compound C=1C=CC=CC=1N(C)CC1=CC=CC=C1 LXZGVFCKZRHKMU-UHFFFAOYSA-N 0.000 description 1
- KQSCBVZELICFPH-UHFFFAOYSA-N n-butyl-n-cyclohexylaniline Chemical compound C=1C=CC=CC=1N(CCCC)C1CCCCC1 KQSCBVZELICFPH-UHFFFAOYSA-N 0.000 description 1
- VQQXVDXXPDMOMH-UHFFFAOYSA-N n-cyclohexyl-n-ethylaniline Chemical compound C=1C=CC=CC=1N(CC)C1CCCCC1 VQQXVDXXPDMOMH-UHFFFAOYSA-N 0.000 description 1
- HRBASXKYUKFHKC-UHFFFAOYSA-N n-cyclohexyl-n-methylaniline Chemical compound C=1C=CC=CC=1N(C)C1CCCCC1 HRBASXKYUKFHKC-UHFFFAOYSA-N 0.000 description 1
- OYIYRYKXEOXXIC-UHFFFAOYSA-N n-cyclopentyl-n,3-dimethylaniline Chemical compound C=1C=CC(C)=CC=1N(C)C1CCCC1 OYIYRYKXEOXXIC-UHFFFAOYSA-N 0.000 description 1
- GRPQYYGFJFDIQI-UHFFFAOYSA-N n-cyclopentyl-n-ethyl-3-methylaniline Chemical compound C=1C=CC(C)=CC=1N(CC)C1CCCC1 GRPQYYGFJFDIQI-UHFFFAOYSA-N 0.000 description 1
- WADJRMVXIXJUOS-UHFFFAOYSA-N n-cyclopentyl-n-ethylaniline Chemical compound C=1C=CC=CC=1N(CC)C1CCCC1 WADJRMVXIXJUOS-UHFFFAOYSA-N 0.000 description 1
- ZPWSDUMJLDOMDQ-UHFFFAOYSA-N n-cyclopentyl-n-methylaniline Chemical compound C=1C=CC=CC=1N(C)C1CCCC1 ZPWSDUMJLDOMDQ-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- VQTGUFBGYOIUFS-UHFFFAOYSA-N nitrosylsulfuric acid Chemical compound OS(=O)(=O)ON=O VQTGUFBGYOIUFS-UHFFFAOYSA-N 0.000 description 1
- 229920000847 nonoxynol Polymers 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical class CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 238000007645 offset printing Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
- C09B29/0805—Amino benzenes free of acid groups
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
- D06P5/003—Transfer printing
- D06P5/004—Transfer printing using subliming dyes
- D06P5/006—Transfer printing using subliming dyes using specified dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Thermal Transfer Or Thermal Recording In General (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19732364475 DE2364475C3 (de) | 1973-12-24 | Verfahren zum Bedrucken von hydrophoben Fasermaterialien nach dem Transferdruckprinzip |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1036756A true CA1036756A (en) | 1978-08-22 |
Family
ID=5901918
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA216,540A Expired CA1036756A (en) | 1973-12-24 | 1974-12-20 | Transfer printing process |
Country Status (13)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2334721A1 (fr) * | 1975-12-11 | 1977-07-08 | Toms River Chemical Corp | Colorants azoiques et leur application dans l'impression par transfert sublimation |
| GB2094934B (en) | 1979-07-19 | 1983-06-02 | Ass Eng France | The reinforcement of piston ring grooves |
| DE3600349A1 (de) * | 1985-08-08 | 1987-02-19 | Bayer Ag | Herstellung von illustrationstiefdruckfarben |
-
1974
- 1974-11-18 IN IN2542/CAL/74A patent/IN143049B/en unknown
- 1974-12-20 DD DD183269A patent/DD117258A5/xx unknown
- 1974-12-20 CA CA216,540A patent/CA1036756A/en not_active Expired
- 1974-12-20 CH CH1708874D patent/CH1708874A4/xx unknown
- 1974-12-20 IT IT30907/74A patent/IT1027953B/it active
- 1974-12-20 JP JP49145787A patent/JPS5094283A/ja active Pending
- 1974-12-20 CH CH1708874A patent/CH583814A/xx not_active IP Right Cessation
- 1974-12-23 BE BE151856A patent/BE823761A/xx unknown
- 1974-12-23 ES ES433287A patent/ES433287A1/es not_active Expired
- 1974-12-23 GB GB5538674A patent/GB1441894A/en not_active Expired
- 1974-12-23 BR BR10770/74A patent/BR7410770D0/pt unknown
- 1974-12-23 NL NL7416793A patent/NL7416793A/xx unknown
- 1974-12-23 AT AT1029174A patent/AT332893B/de not_active IP Right Cessation
- 1974-12-24 FR FR7442656A patent/FR2255416B1/fr not_active Expired
-
1978
- 1978-02-01 JP JP939978A patent/JPS53103081A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CH583814A (enrdf_load_stackoverflow) | 1977-01-14 |
| NL7416793A (nl) | 1975-06-26 |
| FR2255416B1 (enrdf_load_stackoverflow) | 1978-04-14 |
| AT332893B (de) | 1976-10-25 |
| DD117258A5 (enrdf_load_stackoverflow) | 1976-01-05 |
| JPS53103081A (en) | 1978-09-07 |
| BR7410770D0 (pt) | 1975-09-02 |
| IT1027953B (it) | 1978-12-20 |
| CH1708874A4 (enrdf_load_stackoverflow) | 1976-07-15 |
| AU7670374A (en) | 1976-06-24 |
| IN143049B (enrdf_load_stackoverflow) | 1977-09-24 |
| ES433287A1 (es) | 1977-05-16 |
| BE823761A (fr) | 1975-06-23 |
| JPS5094283A (enrdf_load_stackoverflow) | 1975-07-26 |
| ATA1029174A (de) | 1976-02-15 |
| FR2255416A1 (enrdf_load_stackoverflow) | 1975-07-18 |
| GB1441894A (en) | 1976-07-07 |
| DE2364475A1 (de) | 1975-07-10 |
| DE2364475B2 (de) | 1977-01-13 |
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