DE2439950C2 - - Google Patents
Info
- Publication number
- DE2439950C2 DE2439950C2 DE2439950A DE2439950A DE2439950C2 DE 2439950 C2 DE2439950 C2 DE 2439950C2 DE 2439950 A DE2439950 A DE 2439950A DE 2439950 A DE2439950 A DE 2439950A DE 2439950 C2 DE2439950 C2 DE 2439950C2
- Authority
- DE
- Germany
- Prior art keywords
- formula
- triazine
- alkyl
- vat dyes
- parts
- 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
- 239000000984 vat dye Substances 0.000 claims description 27
- -1 cyano, thiocyano Chemical group 0.000 claims description 24
- 150000001412 amines Chemical class 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 125000004414 alkyl thio group Chemical group 0.000 claims description 8
- 238000004043 dyeing Methods 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 125000003277 amino group Chemical group 0.000 claims description 6
- 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 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000002252 acyl group Chemical group 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- RZVHIXYEVGDQDX-UHFFFAOYSA-N 9,10-anthraquinone Chemical group C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 RZVHIXYEVGDQDX-UHFFFAOYSA-N 0.000 claims description 4
- 125000004442 acylamino group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 4
- XBNVWXKPFORCRI-UHFFFAOYSA-N 2h-naphtho[2,3-f]quinolin-1-one Chemical class C1=CC=CC2=CC3=C4C(=O)CC=NC4=CC=C3C=C21 XBNVWXKPFORCRI-UHFFFAOYSA-N 0.000 claims description 3
- RVBXFOZIRRHESC-UHFFFAOYSA-N 4h-naphtho[2,3-f]quinazolin-1-one Chemical class C1=CC=CC2=CC3=C4C(=O)NC=NC4=CC=C3C=C21 RVBXFOZIRRHESC-UHFFFAOYSA-N 0.000 claims description 3
- HUKPVYBUJRAUAG-UHFFFAOYSA-N 7-benzo[a]phenalenone Chemical compound C1=CC(C(=O)C=2C3=CC=CC=2)=C2C3=CC=CC2=C1 HUKPVYBUJRAUAG-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- PGEHNUUBUQTUJB-UHFFFAOYSA-N anthanthrone Chemical compound C1=CC=C2C(=O)C3=CC=C4C=CC=C5C(=O)C6=CC=C1C2=C6C3=C54 PGEHNUUBUQTUJB-UHFFFAOYSA-N 0.000 claims description 3
- ACPOUJIDANTYHO-UHFFFAOYSA-N anthra[1,9-cd]pyrazol-6(2H)-one Chemical compound C1=CC(C(=O)C=2C3=CC=CC=2)=C2C3=NNC2=C1 ACPOUJIDANTYHO-UHFFFAOYSA-N 0.000 claims description 3
- 125000001769 aryl amino group Chemical group 0.000 claims description 3
- 125000005110 aryl thio group Chemical group 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- OBJNZHVOCNPSCS-UHFFFAOYSA-N naphtho[2,3-f]quinazoline Chemical class C1=NC=C2C3=CC4=CC=CC=C4C=C3C=CC2=N1 OBJNZHVOCNPSCS-UHFFFAOYSA-N 0.000 claims description 3
- 230000004048 modification Effects 0.000 claims description 2
- 238000012986 modification Methods 0.000 claims description 2
- 239000004753 textile Substances 0.000 claims description 2
- 239000000975 dye Substances 0.000 description 29
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 22
- 238000009833 condensation Methods 0.000 description 14
- 230000005494 condensation Effects 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 229920000742 Cotton Polymers 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- MWPZLWRHHPWTFS-UHFFFAOYSA-N 2,4-dichloro-6-methylsulfanyl-1,3,5-triazine Chemical compound CSC1=NC(Cl)=NC(Cl)=N1 MWPZLWRHHPWTFS-UHFFFAOYSA-N 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000003513 alkali Substances 0.000 description 4
- 150000003973 alkyl amines Chemical class 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 150000004056 anthraquinones Chemical class 0.000 description 3
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 238000004040 coloring Methods 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000003973 paint Substances 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- 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 2
- ZCZJJJXYLSCYII-UHFFFAOYSA-N 2,4-dichloro-6-ethylsulfanyl-1,3,5-triazine Chemical compound CCSC1=NC(Cl)=NC(Cl)=N1 ZCZJJJXYLSCYII-UHFFFAOYSA-N 0.000 description 2
- XPBYMVFXDJZOAW-UHFFFAOYSA-N 2,4-dichloro-6-propan-2-ylsulfanyl-1,3,5-triazine Chemical compound CC(C)SC1=NC(Cl)=NC(Cl)=N1 XPBYMVFXDJZOAW-UHFFFAOYSA-N 0.000 description 2
- OTFPBEGMQXEJJG-UHFFFAOYSA-N 2,4-dichloro-6-propylsulfanyl-1,3,5-triazine Chemical compound CCCSC1=NC(Cl)=NC(Cl)=N1 OTFPBEGMQXEJJG-UHFFFAOYSA-N 0.000 description 2
- FRCJZVRRIQZXBL-UHFFFAOYSA-N 2-butylsulfanyl-4,6-dichloro-1,3,5-triazine Chemical compound CCCCSC1=NC(Cl)=NC(Cl)=N1 FRCJZVRRIQZXBL-UHFFFAOYSA-N 0.000 description 2
- SFPNVVXUUHYBQW-UHFFFAOYSA-N 6-(methylthio)-1,3,5-triazine-2,4-diamine Chemical compound CSC1=NC(N)=NC(N)=N1 SFPNVVXUUHYBQW-UHFFFAOYSA-N 0.000 description 2
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 2
- 240000007817 Olea europaea Species 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 229920000180 alkyd Polymers 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- FWEQPMZEKHHFTB-UHFFFAOYSA-N n-(5-amino-9,10-dioxoanthracen-1-yl)benzamide Chemical compound C1=CC=C2C(=O)C=3C(N)=CC=CC=3C(=O)C2=C1NC(=O)C1=CC=CC=C1 FWEQPMZEKHHFTB-UHFFFAOYSA-N 0.000 description 2
- AJDUTMFFZHIJEM-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229920000915 polyvinyl chloride Polymers 0.000 description 2
- 239000004800 polyvinyl chloride Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 239000001043 yellow dye Substances 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- ZQNAPBOSLCTZIB-UHFFFAOYSA-N 1,3-dichloroanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC(Cl)=C3C(=O)C2=C1 ZQNAPBOSLCTZIB-UHFFFAOYSA-N 0.000 description 1
- SRRLOAAMZYZYQY-UHFFFAOYSA-N 1,5-dibromoanthracene-9,10-dione Chemical compound O=C1C2=C(Br)C=CC=C2C(=O)C2=C1C=CC=C2Br SRRLOAAMZYZYQY-UHFFFAOYSA-N 0.000 description 1
- MQIUMARJCOGCIM-UHFFFAOYSA-N 1,5-dichloroanthracene-9,10-dione Chemical compound O=C1C2=C(Cl)C=CC=C2C(=O)C2=C1C=CC=C2Cl MQIUMARJCOGCIM-UHFFFAOYSA-N 0.000 description 1
- GYCAKIYVWNSQFO-UHFFFAOYSA-N 1,6-dichloroanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3C(=O)C2=C1Cl GYCAKIYVWNSQFO-UHFFFAOYSA-N 0.000 description 1
- QIFCTRBXWWHIFG-UHFFFAOYSA-N 1,8-dibromoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC(Br)=C2C(=O)C2=C1C=CC=C2Br QIFCTRBXWWHIFG-UHFFFAOYSA-N 0.000 description 1
- VBQNYYXVDQUKIU-UHFFFAOYSA-N 1,8-dichloroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC(Cl)=C2C(=O)C2=C1C=CC=C2Cl VBQNYYXVDQUKIU-UHFFFAOYSA-N 0.000 description 1
- ZMESHQOXZMOOQQ-UHFFFAOYSA-N 1-(naphthalen-1-ylmethyl)naphthalene Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 ZMESHQOXZMOOQQ-UHFFFAOYSA-N 0.000 description 1
- PQZQBQUFXZDPOH-UHFFFAOYSA-N 1-(propylamino)anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NCCC PQZQBQUFXZDPOH-UHFFFAOYSA-N 0.000 description 1
- ZLCUIOWQYBYEBG-UHFFFAOYSA-N 1-Amino-2-methylanthraquinone Chemical compound C1=CC=C2C(=O)C3=C(N)C(C)=CC=C3C(=O)C2=C1 ZLCUIOWQYBYEBG-UHFFFAOYSA-N 0.000 description 1
- WITKIIIPSSFHST-UHFFFAOYSA-N 1-[(9,10-dioxoanthracen-1-yl)amino]anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC1=C2C(=O)C3=CC=CC=C3C(=O)C2=CC=C1 WITKIIIPSSFHST-UHFFFAOYSA-N 0.000 description 1
- QQOBTPNGSQEDAS-UHFFFAOYSA-N 1-amino-2-chloroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC(Cl)=C2N QQOBTPNGSQEDAS-UHFFFAOYSA-N 0.000 description 1
- DYHUOVJBKPICOY-UHFFFAOYSA-N 1-amino-3-chloro-2-methylanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(N)=C(C)C(Cl)=C2 DYHUOVJBKPICOY-UHFFFAOYSA-N 0.000 description 1
- FWZSKNXEMCLIOL-UHFFFAOYSA-N 1-amino-3-chloro-6-methylanthracene-9,10-dione Chemical compound C1=C(Cl)C=C2C(=O)C3=CC(C)=CC=C3C(=O)C2=C1N FWZSKNXEMCLIOL-UHFFFAOYSA-N 0.000 description 1
- XEONODGQEFLDTL-UHFFFAOYSA-N 1-amino-3-chloroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=C(Cl)C=C2N XEONODGQEFLDTL-UHFFFAOYSA-N 0.000 description 1
- AWACQBFBMROGQC-UHFFFAOYSA-N 1-amino-4-chloroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(Cl)=CC=C2N AWACQBFBMROGQC-UHFFFAOYSA-N 0.000 description 1
- KXOGXZAXERYOTC-UHFFFAOYSA-N 1-amino-4-methoxyanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(N)=CC=C2OC KXOGXZAXERYOTC-UHFFFAOYSA-N 0.000 description 1
- YFEHGCGWUWOAFA-UHFFFAOYSA-N 1-amino-6,7-dichloroanthracene-9,10-dione Chemical compound O=C1C2=CC(Cl)=C(Cl)C=C2C(=O)C2=C1C=CC=C2N YFEHGCGWUWOAFA-UHFFFAOYSA-N 0.000 description 1
- GGJNMALYBXOQEF-UHFFFAOYSA-N 1-amino-7-chloroanthracene-9,10-dione Chemical compound O=C1C2=CC=C(Cl)C=C2C(=O)C2=C1C=CC=C2N GGJNMALYBXOQEF-UHFFFAOYSA-N 0.000 description 1
- IBORLNHLBSQHQL-UHFFFAOYSA-N 1-bromo-2-methoxyanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C(Br)C(OC)=CC=C3C(=O)C2=C1 IBORLNHLBSQHQL-UHFFFAOYSA-N 0.000 description 1
- ITXBUJHIGBXXKK-UHFFFAOYSA-N 1-bromo-4-methoxyanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(Br)=CC=C2OC ITXBUJHIGBXXKK-UHFFFAOYSA-N 0.000 description 1
- CXTPIHZYOGDSLV-UHFFFAOYSA-N 1-bromoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2Br CXTPIHZYOGDSLV-UHFFFAOYSA-N 0.000 description 1
- WEVFFIZMKQMIFI-UHFFFAOYSA-N 1-chloro-2-(methylamino)anthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C(Cl)C(NC)=CC=C3C(=O)C2=C1 WEVFFIZMKQMIFI-UHFFFAOYSA-N 0.000 description 1
- MRBBOZQDOWNTLW-UHFFFAOYSA-N 1-chloro-4-methoxyanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(Cl)=CC=C2OC MRBBOZQDOWNTLW-UHFFFAOYSA-N 0.000 description 1
- FUACWUFYFGVLMM-UHFFFAOYSA-N 1-chloro-4-methylanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(Cl)=CC=C2C FUACWUFYFGVLMM-UHFFFAOYSA-N 0.000 description 1
- OSBCKVKNSCPFHD-UHFFFAOYSA-N 10H-anthracen-9-one pyrimidine Chemical compound C1=CC=CC=2CC3=CC=CC=C3C(C12)=O.N1=CN=CC=C1 OSBCKVKNSCPFHD-UHFFFAOYSA-N 0.000 description 1
- YHOZSDAIDDDNIK-UHFFFAOYSA-N 10h-anthracen-9-one;1,2-thiazol-3-amine Chemical compound NC=1C=CSN=1.C1=CC=C2C(=O)C3=CC=CC=C3CC2=C1 YHOZSDAIDDDNIK-UHFFFAOYSA-N 0.000 description 1
- ORORZEXLELVUDX-UHFFFAOYSA-N 10h-anthracen-9-one;1,2-thiazole Chemical compound C=1C=NSC=1.C1=CC=C2C(=O)C3=CC=CC=C3CC2=C1 ORORZEXLELVUDX-UHFFFAOYSA-N 0.000 description 1
- YWVPLPVOZCOMQA-UHFFFAOYSA-N 2,3,4-tribromo-2H-pyranthren-1-one Chemical compound C1=C2C(C(Br)=C(Br)C(C3=O)Br)=C3C=C(C=C3)C2=C2C3=CC3=C(C=CC=C4)C4=CC4=CC=C1C2=C34 YWVPLPVOZCOMQA-UHFFFAOYSA-N 0.000 description 1
- VHYBUUMUUNCHCK-UHFFFAOYSA-N 2,4,6-tribromo-1,3,5-triazine Chemical compound BrC1=NC(Br)=NC(Br)=N1 VHYBUUMUUNCHCK-UHFFFAOYSA-N 0.000 description 1
- JUFYHUWBLXKCJM-UHFFFAOYSA-N 2,6-dibromoanthracene-9,10-dione Chemical compound BrC1=CC=C2C(=O)C3=CC(Br)=CC=C3C(=O)C2=C1 JUFYHUWBLXKCJM-UHFFFAOYSA-N 0.000 description 1
- KJGPMAHVCDFRBN-UHFFFAOYSA-N 2,6-dichloroanthracene-9,10-dione Chemical compound ClC1=CC=C2C(=O)C3=CC(Cl)=CC=C3C(=O)C2=C1 KJGPMAHVCDFRBN-UHFFFAOYSA-N 0.000 description 1
- SAKIJMSLTKGUQV-UHFFFAOYSA-N 2,7-dibromoanthracene-9,10-dione Chemical compound C1=C(Br)C=C2C(=O)C3=CC(Br)=CC=C3C(=O)C2=C1 SAKIJMSLTKGUQV-UHFFFAOYSA-N 0.000 description 1
- HQUNBWGQFXPVES-UHFFFAOYSA-N 2,7-dichloroanthracene-9,10-dione Chemical compound C1=C(Cl)C=C2C(=O)C3=CC(Cl)=CC=C3C(=O)C2=C1 HQUNBWGQFXPVES-UHFFFAOYSA-N 0.000 description 1
- WOPHAXVWACNHPM-UHFFFAOYSA-N 2-(methylthio)-1,3,5-triazine Chemical compound CSC1=NC=NC=N1 WOPHAXVWACNHPM-UHFFFAOYSA-N 0.000 description 1
- XOGPDSATLSAZEK-UHFFFAOYSA-N 2-Aminoanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(N)=CC=C3C(=O)C2=C1 XOGPDSATLSAZEK-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- GUUWHMTVVVFXIF-UHFFFAOYSA-N 2-acetyl-1,4-diaminoanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C(N)C(C(=O)C)=CC(N)=C3C(=O)C2=C1 GUUWHMTVVVFXIF-UHFFFAOYSA-N 0.000 description 1
- WVIQUGWECBTDMQ-UHFFFAOYSA-N 2-acetyl-1-amino-4-chloroanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C(N)C(C(=O)C)=CC(Cl)=C3C(=O)C2=C1 WVIQUGWECBTDMQ-UHFFFAOYSA-N 0.000 description 1
- VMOJFUJVEWWUAV-UHFFFAOYSA-N 2-amino-3-chloroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=C(N)C(Cl)=C2 VMOJFUJVEWWUAV-UHFFFAOYSA-N 0.000 description 1
- VTSDGYDTWADUJQ-UHFFFAOYSA-N 2-bromoanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC(Br)=CC=C3C(=O)C2=C1 VTSDGYDTWADUJQ-UHFFFAOYSA-N 0.000 description 1
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- GWOWVOYJLHSRJJ-UHFFFAOYSA-L cadmium stearate Chemical compound [Cd+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O GWOWVOYJLHSRJJ-UHFFFAOYSA-L 0.000 description 1
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- 239000005018 casein Substances 0.000 description 1
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- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 1
- 239000000986 disperse dye Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 1
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- 230000002349 favourable effect Effects 0.000 description 1
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- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
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- XFSTXCLZOYNIOA-UHFFFAOYSA-N n-(4-amino-9,10-dioxoanthracen-1-yl)-4-methylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=CC=C(N)C2=C1C(=O)C1=CC=CC=C1C2=O XFSTXCLZOYNIOA-UHFFFAOYSA-N 0.000 description 1
- GNRDMELOAWUYCJ-UHFFFAOYSA-N n-(4-amino-9,10-dioxoanthracen-1-yl)-4-phenylbenzamide Chemical compound C1=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=CC=C1NC(=O)C(C=C1)=CC=C1C1=CC=CC=C1 GNRDMELOAWUYCJ-UHFFFAOYSA-N 0.000 description 1
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- QQFCYAFTRWDEJR-UHFFFAOYSA-N n-(4-bromo-9,10-dioxoanthracen-1-yl)-4-phenylbenzamide Chemical compound C1=2C(=O)C3=CC=CC=C3C(=O)C=2C(Br)=CC=C1NC(=O)C(C=C1)=CC=C1C1=CC=CC=C1 QQFCYAFTRWDEJR-UHFFFAOYSA-N 0.000 description 1
- JKRCBOYQTINLRS-UHFFFAOYSA-N n-(4-bromo-9,10-dioxoanthracen-1-yl)benzamide Chemical compound C1=2C(=O)C3=CC=CC=C3C(=O)C=2C(Br)=CC=C1NC(=O)C1=CC=CC=C1 JKRCBOYQTINLRS-UHFFFAOYSA-N 0.000 description 1
- FNCVZYRPXOZNSM-UHFFFAOYSA-N n-(4-chloro-9,10-dioxoanthracen-1-yl)benzamide Chemical compound C1=2C(=O)C3=CC=CC=C3C(=O)C=2C(Cl)=CC=C1NC(=O)C1=CC=CC=C1 FNCVZYRPXOZNSM-UHFFFAOYSA-N 0.000 description 1
- YEBZGBFSKMGTJA-UHFFFAOYSA-N n-(5-bromo-9,10-dioxoanthracen-1-yl)benzamide Chemical compound C1=CC=C2C(=O)C=3C(Br)=CC=CC=3C(=O)C2=C1NC(=O)C1=CC=CC=C1 YEBZGBFSKMGTJA-UHFFFAOYSA-N 0.000 description 1
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- VDCUNNJIPITONP-UHFFFAOYSA-N n-(5-chloro-9,10-dioxoanthracen-1-yl)benzamide Chemical compound C1=CC=C2C(=O)C=3C(Cl)=CC=CC=3C(=O)C2=C1NC(=O)C1=CC=CC=C1 VDCUNNJIPITONP-UHFFFAOYSA-N 0.000 description 1
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- 230000007935 neutral effect Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 229940079938 nitrocellulose Drugs 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
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- 229920002050 silicone resin Polymers 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
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- 159000000000 sodium salts Chemical class 0.000 description 1
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- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
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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
- C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
-
- 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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/36—Dyes with acylated amino groups
- C09B1/46—Dyes with acylated amino groups the acyl groups being residues of cyanuric acid or an analogous heterocyclic compound
- C09B1/467—Dyes with acylated amino groups the acyl groups being residues of cyanuric acid or an analogous heterocyclic compound attached to two or more anthraquinone rings
-
- 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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/48—Anthrimides
-
- 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
- C09B3/00—Dyes with an anthracene nucleus condensed with one or more carbocyclic rings
-
- 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
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/22—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using vat dyestuffs including indigo
-
- 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
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/22—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using vat dyestuffs including indigo
- D06P1/24—Anthraquinone dyes or anthracene nucleus containing vat dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1206773A CH606271A5 (en) | 1973-08-22 | 1973-08-22 | Di-amino-alkyl-thio-s-triazine vat dyes |
| CH772774 | 1974-06-06 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2439950A1 DE2439950A1 (de) | 1975-03-06 |
| DE2439950C2 true DE2439950C2 (en, 2012) | 1988-02-18 |
Family
ID=25702041
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2439950A Granted DE2439950A1 (de) | 1973-08-22 | 1974-08-20 | Kuepenfarbstoffe, deren herstellung und verwendung |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US3972881A (en, 2012) |
| JP (1) | JPS6048545B2 (en, 2012) |
| AR (1) | AR203298A1 (en, 2012) |
| BR (1) | BR7406914D0 (en, 2012) |
| CA (1) | CA1042883A (en, 2012) |
| DE (1) | DE2439950A1 (en, 2012) |
| ES (2) | ES429429A1 (en, 2012) |
| FR (1) | FR2245733B1 (en, 2012) |
| GB (1) | GB1476687A (en, 2012) |
| IT (1) | IT1019060B (en, 2012) |
| NL (1) | NL7409935A (en, 2012) |
| SU (1) | SU818495A3 (en, 2012) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1543541A (en) * | 1976-05-27 | 1979-04-04 | Nippon Kayaku Kk | Fibre reactive anthraquinone dyestuffs |
| CH625537A5 (en, 2012) * | 1977-06-14 | 1981-09-30 | Ciba Geigy Ag | |
| CH635855A5 (de) * | 1978-01-18 | 1983-04-29 | Ciba Geigy Ag | Verfahren zur herstellung von kuepenfarbstoffen. |
| KR100620410B1 (ko) * | 2001-02-06 | 2006-09-13 | 엠도흐멘코리아 주식회사 | 이소티아졸안트론 화합물의 제조방법 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1164001B (de) * | 1958-05-30 | 1964-02-27 | Ciba Aktiengesellschaft, Basel (Schweiz) | Verfahren zur Herstellung von Anthrachinonküpenfarbstoffen. |
| BE584852A (en, 2012) * | 1958-11-21 | |||
| FR1242048A (fr) * | 1958-12-24 | 1960-09-23 | Ciba Geigy | Procédé de préparation de colorants de cuve anthraquinoniques |
| CH428994A (de) * | 1961-03-24 | 1967-01-31 | Durand & Huguenin Ag | Verfahren zur Herstellung von neuen, wasserlöslichen Leukoschwefelsäureestersalzen von Küpenfarbstoffen der Anthrachinonreihe |
| NL270721A (en, 2012) * | 1960-10-28 | |||
| CH514987A (de) * | 1969-04-24 | 1971-11-15 | Ciba Geigy Ag | Neues herbizides Mittel |
-
1974
- 1974-07-19 GB GB3219674A patent/GB1476687A/en not_active Expired
- 1974-07-23 NL NL7409935A patent/NL7409935A/xx not_active Application Discontinuation
- 1974-08-19 US US05/498,698 patent/US3972881A/en not_active Expired - Lifetime
- 1974-08-19 IT IT52644/74A patent/IT1019060B/it active
- 1974-08-20 CA CA207,388A patent/CA1042883A/en not_active Expired
- 1974-08-20 SU SU742054183A patent/SU818495A3/ru active
- 1974-08-20 DE DE2439950A patent/DE2439950A1/de active Granted
- 1974-08-20 FR FR7428574A patent/FR2245733B1/fr not_active Expired
- 1974-08-20 AR AR255238A patent/AR203298A1/es active
- 1974-08-21 BR BR6914/74A patent/BR7406914D0/pt unknown
- 1974-08-21 ES ES429429A patent/ES429429A1/es not_active Expired
- 1974-08-21 ES ES429416A patent/ES429416A1/es not_active Expired
- 1974-08-22 JP JP49095613A patent/JPS6048545B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5050429A (en, 2012) | 1975-05-06 |
| ES429416A1 (es) | 1977-02-16 |
| FR2245733A1 (en, 2012) | 1975-04-25 |
| NL7409935A (nl) | 1975-02-25 |
| CA1042883A (en) | 1978-11-21 |
| BR7406914D0 (pt) | 1975-06-17 |
| ES429429A1 (es) | 1977-02-16 |
| AR203298A1 (es) | 1975-08-29 |
| JPS6048545B2 (ja) | 1985-10-28 |
| FR2245733B1 (en, 2012) | 1976-12-31 |
| GB1476687A (en) | 1977-06-16 |
| IT1019060B (it) | 1977-11-10 |
| DE2439950A1 (de) | 1975-03-06 |
| SU818495A3 (ru) | 1981-03-30 |
| US3972881A (en) | 1976-08-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8128 | New person/name/address of the agent |
Representative=s name: SCHWABE, H., DIPL.-ING. SANDMAIR, K., DIPL.-CHEM. |
|
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |