CA1045133A - Process for the manufacture of halogen-containing anthraquinoidal compounds, their use and new halogen-containing anthraquinoidal compounds - Google Patents
Process for the manufacture of halogen-containing anthraquinoidal compounds, their use and new halogen-containing anthraquinoidal compoundsInfo
- Publication number
- CA1045133A CA1045133A CA211,018A CA211018A CA1045133A CA 1045133 A CA1045133 A CA 1045133A CA 211018 A CA211018 A CA 211018A CA 1045133 A CA1045133 A CA 1045133A
- Authority
- CA
- Canada
- Prior art keywords
- denotes
- hydrogen
- formula
- group
- compound
- 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
- 150000001875 compounds Chemical class 0.000 title claims abstract description 21
- 238000000034 method Methods 0.000 title claims abstract description 15
- 229910052736 halogen Inorganic materials 0.000 title claims abstract description 13
- 150000002367 halogens Chemical class 0.000 title claims abstract description 13
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 29
- 239000001257 hydrogen Substances 0.000 claims abstract description 29
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 14
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 6
- 125000003435 aroyl group Chemical group 0.000 claims abstract description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims abstract description 3
- -1 diphenylyloxy Chemical group 0.000 claims description 41
- 229910052794 bromium Inorganic materials 0.000 claims description 29
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 27
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 27
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 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 13
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- 239000000460 chlorine Substances 0.000 claims description 11
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 9
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000001769 aryl amino group Chemical group 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- RZVHIXYEVGDQDX-UHFFFAOYSA-N 9,10-anthraquinone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 RZVHIXYEVGDQDX-UHFFFAOYSA-N 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- 238000004043 dyeing Methods 0.000 abstract description 16
- 230000002140 halogenating effect Effects 0.000 abstract description 4
- 150000002894 organic compounds Chemical class 0.000 abstract description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 31
- 239000000975 dye Substances 0.000 description 23
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 18
- 239000000126 substance Substances 0.000 description 17
- 229920000728 polyester Polymers 0.000 description 16
- 239000000463 material Substances 0.000 description 14
- 239000000203 mixture Substances 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 238000004040 coloring Methods 0.000 description 10
- 150000004056 anthraquinones Chemical class 0.000 description 9
- 229920000139 polyethylene terephthalate Polymers 0.000 description 9
- 239000005020 polyethylene terephthalate Substances 0.000 description 9
- KOJOUCAVSDKDPR-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)benzamide Chemical compound C=1C=CC=2C(=O)C3=CC=CC=C3C(=O)C=2C=1NC(=O)C1=CC=CC=C1 KOJOUCAVSDKDPR-UHFFFAOYSA-N 0.000 description 8
- 229960001156 mitoxantrone Drugs 0.000 description 7
- 239000000047 product Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- XRIGHGYEGNDPEU-UHFFFAOYSA-N 1-anilinoanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1NC1=CC=CC=C1 XRIGHGYEGNDPEU-UHFFFAOYSA-N 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 239000004744 fabric Substances 0.000 description 5
- 230000026030 halogenation Effects 0.000 description 5
- 238000005658 halogenation reaction Methods 0.000 description 5
- OBJNZHVOCNPSCS-UHFFFAOYSA-N naphtho[2,3-f]quinazoline Chemical compound C1=NC=C2C3=CC4=CC=CC=C4C=C3C=CC2=N1 OBJNZHVOCNPSCS-UHFFFAOYSA-N 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 239000004952 Polyamide Substances 0.000 description 4
- 238000005108 dry cleaning Methods 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 229920002647 polyamide Polymers 0.000 description 4
- 238000010186 staining Methods 0.000 description 4
- 238000000859 sublimation Methods 0.000 description 4
- 230000008022 sublimation Effects 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 238000006068 polycondensation reaction Methods 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- ZKIVUFFTMWIBCO-UHFFFAOYSA-N 1,5-bis(4-methylanilino)anthracene-9,10-dione Chemical compound C1=CC(C)=CC=C1NC1=CC=CC2=C1C(=O)C1=CC=CC(NC=3C=CC(C)=CC=3)=C1C2=O ZKIVUFFTMWIBCO-UHFFFAOYSA-N 0.000 description 2
- FPRGJFFNVANESG-UHFFFAOYSA-N 1-phenylsulfanylanthracene-9,10-dione Chemical class C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1SC1=CC=CC=C1 FPRGJFFNVANESG-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 230000031709 bromination Effects 0.000 description 2
- 238000005893 bromination reaction Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000005660 chlorination reaction Methods 0.000 description 2
- 229910001919 chlorite Inorganic materials 0.000 description 2
- 229910052619 chlorite group Inorganic materials 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 238000010409 ironing Methods 0.000 description 2
- 238000002074 melt spinning Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- GUEIZVNYDFNHJU-UHFFFAOYSA-N quinizarin Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=CC=C2O GUEIZVNYDFNHJU-UHFFFAOYSA-N 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ZYECOAILUNWEAL-NUDFZHEQSA-N (4z)-4-[[2-methoxy-5-(phenylcarbamoyl)phenyl]hydrazinylidene]-n-(3-nitrophenyl)-3-oxonaphthalene-2-carboxamide Chemical compound COC1=CC=C(C(=O)NC=2C=CC=CC=2)C=C1N\N=C(C1=CC=CC=C1C=1)/C(=O)C=1C(=O)NC1=CC=CC([N+]([O-])=O)=C1 ZYECOAILUNWEAL-NUDFZHEQSA-N 0.000 description 1
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- YFGXHOXJMJBGNY-UHFFFAOYSA-N 1,4,5,8-tetraanilinoanthracene-9,10-dione Chemical compound C1=CC(NC=2C=CC=CC=2)=C2C(=O)C3=C(NC=4C=CC=CC=4)C=CC(NC=4C=CC=CC=4)=C3C(=O)C2=C1NC1=CC=CC=C1 YFGXHOXJMJBGNY-UHFFFAOYSA-N 0.000 description 1
- CYHXULBAHNKPOM-UHFFFAOYSA-N 1,4,5-trianilino-8-hydroxyanthracene-9,10-dione Chemical compound C1=2C(=O)C3=C(NC=4C=CC=CC=4)C=CC(NC=4C=CC=CC=4)=C3C(=O)C=2C(O)=CC=C1NC1=CC=CC=C1 CYHXULBAHNKPOM-UHFFFAOYSA-N 0.000 description 1
- ROCQMWBLOZLGOD-UHFFFAOYSA-N 1,4-bis(4-benzylanilino)-5-hydroxyanthracene-9,10-dione Chemical compound C1=CC(NC=2C=CC(CC=3C=CC=CC=3)=CC=2)=C2C(=O)C=3C(O)=CC=CC=3C(=O)C2=C1NC(C=C1)=CC=C1CC1=CC=CC=C1 ROCQMWBLOZLGOD-UHFFFAOYSA-N 0.000 description 1
- PDDUCMVNYPVMFA-UHFFFAOYSA-N 1,4-dianilino-5-hydroxyanthracene-9,10-dione Chemical compound C1=CC(NC=2C=CC=CC=2)=C2C(=O)C=3C(O)=CC=CC=3C(=O)C2=C1NC1=CC=CC=C1 PDDUCMVNYPVMFA-UHFFFAOYSA-N 0.000 description 1
- CKBFYMOTEJMJTP-UHFFFAOYSA-N 1,5-bis(3-methylanilino)anthracene-9,10-dione Chemical compound CC1=CC=CC(NC=2C=3C(=O)C4=CC=CC(NC=5C=C(C)C=CC=5)=C4C(=O)C=3C=CC=2)=C1 CKBFYMOTEJMJTP-UHFFFAOYSA-N 0.000 description 1
- JOVYZKJSVDUVAE-UHFFFAOYSA-N 1,5-bis(4-chloroanilino)anthracene-9,10-dione Chemical compound C1=CC(Cl)=CC=C1NC1=CC=CC2=C1C(=O)C1=CC=CC(NC=3C=CC(Cl)=CC=3)=C1C2=O JOVYZKJSVDUVAE-UHFFFAOYSA-N 0.000 description 1
- SZBCGALOEJCNMH-UHFFFAOYSA-N 1,5-diamino-4,8-bis(4-methylanilino)anthracene-9,10-dione Chemical compound C1=CC(C)=CC=C1NC1=CC=C(N)C2=C1C(=O)C1=C(N)C=CC(NC=3C=CC(C)=CC=3)=C1C2=O SZBCGALOEJCNMH-UHFFFAOYSA-N 0.000 description 1
- RCIJNRUZBPLGKJ-UHFFFAOYSA-N 1,8-bis(2-ethylanilino)anthracene-9,10-dione Chemical compound CCC1=CC=CC=C1NC1=CC=CC2=C1C(=O)C1=C(NC=3C(=CC=CC=3)CC)C=CC=C1C2=O RCIJNRUZBPLGKJ-UHFFFAOYSA-N 0.000 description 1
- TWOSUNBTTMOKAN-UHFFFAOYSA-N 1,8-bis(4-benzoylanilino)anthracene-9,10-dione Chemical compound C=1C=C(NC=2C=3C(=O)C4=C(NC=5C=CC(=CC=5)C(=O)C=5C=CC=CC=5)C=CC=C4C(=O)C=3C=CC=2)C=CC=1C(=O)C1=CC=CC=C1 TWOSUNBTTMOKAN-UHFFFAOYSA-N 0.000 description 1
- VFCLJTMDHRGPTF-UHFFFAOYSA-N 1,8-bis(4-benzylanilino)anthracene-9,10-dione Chemical compound C=12C(=O)C3=C(NC=4C=CC(CC=5C=CC=CC=5)=CC=4)C=CC=C3C(=O)C2=CC=CC=1NC(C=C1)=CC=C1CC1=CC=CC=C1 VFCLJTMDHRGPTF-UHFFFAOYSA-N 0.000 description 1
- OZABUTKVDLHOOK-UHFFFAOYSA-N 1,8-bis(4-ethoxyanilino)anthracene-9,10-dione Chemical compound C1=CC(OCC)=CC=C1NC1=CC=CC2=C1C(=O)C1=C(NC=3C=CC(OCC)=CC=3)C=CC=C1C2=O OZABUTKVDLHOOK-UHFFFAOYSA-N 0.000 description 1
- CNRPDCKHCGUKDK-UHFFFAOYSA-N 1,8-bis(phenylsulfanyl)anthracene-9,10-dione Chemical compound C=12C(=O)C3=C(SC=4C=CC=CC=4)C=CC=C3C(=O)C2=CC=CC=1SC1=CC=CC=C1 CNRPDCKHCGUKDK-UHFFFAOYSA-N 0.000 description 1
- QWXDVWSEUJXVIK-UHFFFAOYSA-N 1,8-diaminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC(N)=C2C(=O)C2=C1C=CC=C2N QWXDVWSEUJXVIK-UHFFFAOYSA-N 0.000 description 1
- NILBWBQAUNENGK-UHFFFAOYSA-N 1,8-dianilino-4,5-dihydroxyanthracene-9,10-dione Chemical compound C1=2C(=O)C3=C(NC=4C=CC=CC=4)C=CC(O)=C3C(=O)C=2C(O)=CC=C1NC1=CC=CC=C1 NILBWBQAUNENGK-UHFFFAOYSA-N 0.000 description 1
- GYIADLIECYSJEO-UHFFFAOYSA-N 1,8-dianilinoanthracene-9,10-dione Chemical compound C=12C(=O)C3=C(NC=4C=CC=CC=4)C=CC=C3C(=O)C2=CC=CC=1NC1=CC=CC=C1 GYIADLIECYSJEO-UHFFFAOYSA-N 0.000 description 1
- MFPXWYCEOHQEFI-UHFFFAOYSA-N 1-(4-anilinoanilino)-4-hydroxy-2-phenoxyanthracene-9,10-dione Chemical compound C=1C=C(NC=2C=CC=CC=2)C=CC=1NC=1C=2C(=O)C3=CC=CC=C3C(=O)C=2C(O)=CC=1OC1=CC=CC=C1 MFPXWYCEOHQEFI-UHFFFAOYSA-N 0.000 description 1
- FVISJFYQZYUVGI-UHFFFAOYSA-N 1-(4-anilinoanilino)anthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1NC(C=C1)=CC=C1NC1=CC=CC=C1 FVISJFYQZYUVGI-UHFFFAOYSA-N 0.000 description 1
- GBDSOCBCFPPRGC-UHFFFAOYSA-N 1-(4-benzoylanilino)-4-hydroxy-2-phenoxyanthracene-9,10-dione Chemical compound C=1C=C(C(=O)C=2C=CC=CC=2)C=CC=1NC=1C=2C(=O)C3=CC=CC=C3C(=O)C=2C(O)=CC=1OC1=CC=CC=C1 GBDSOCBCFPPRGC-UHFFFAOYSA-N 0.000 description 1
- CWXAVEIGKXOKHA-UHFFFAOYSA-N 1-(4-benzoylanilino)anthracene-9,10-dione Chemical compound C=1C=C(NC=2C=3C(=O)C4=CC=CC=C4C(=O)C=3C=CC=2)C=CC=1C(=O)C1=CC=CC=C1 CWXAVEIGKXOKHA-UHFFFAOYSA-N 0.000 description 1
- UCPITPQLHJEBHP-UHFFFAOYSA-N 1-N-phenyl-4-N-(2-phenyl-1H-naphtho[7,6-f]quinazolin-11-yl)benzene-1,4-diamine Chemical compound C12=CC3=C4CN(C=5C=CC=CC=5)C=NC4=CC=C3C=C2C=CC=C1NC(C=C1)=CC=C1NC1=CC=CC=C1 UCPITPQLHJEBHP-UHFFFAOYSA-N 0.000 description 1
- LCGLFADRRIFFBX-UHFFFAOYSA-N 1-anilino-4-(4-anilinoanilino)anthracene-9,10-dione Chemical compound C1=CC(NC=2C=CC=CC=2)=C2C(=O)C3=CC=CC=C3C(=O)C2=C1NC(C=C1)=CC=C1NC1=CC=CC=C1 LCGLFADRRIFFBX-UHFFFAOYSA-N 0.000 description 1
- HPUIUQZSAIZALP-UHFFFAOYSA-N 1-anilino-4-(4-benzoylanilino)anthracene-9,10-dione Chemical compound C=1C=C(NC=2C=3C(=O)C4=CC=CC=C4C(=O)C=3C(NC=3C=CC=CC=3)=CC=2)C=CC=1C(=O)C1=CC=CC=C1 HPUIUQZSAIZALP-UHFFFAOYSA-N 0.000 description 1
- XZWIYSPVASNDHN-UHFFFAOYSA-N 1-hydroxy-4-phenoxyanthracene-9,10-dione Chemical compound C1=2C(=O)C3=CC=CC=C3C(=O)C=2C(O)=CC=C1OC1=CC=CC=C1 XZWIYSPVASNDHN-UHFFFAOYSA-N 0.000 description 1
- BTLXPCBPYBNQNR-UHFFFAOYSA-N 1-hydroxyanthraquinone Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2O BTLXPCBPYBNQNR-UHFFFAOYSA-N 0.000 description 1
- ZBZRJRVPMDEHFT-UHFFFAOYSA-N 2-[2-[[8-[2-(carboxymethyl)anilino]-9,10-dioxoanthracen-1-yl]amino]phenyl]acetic acid Chemical compound OC(=O)CC1=CC=CC=C1NC1=CC=CC2=C1C(=O)C1=C(NC=3C(=CC=CC=3)CC(O)=O)C=CC=C1C2=O ZBZRJRVPMDEHFT-UHFFFAOYSA-N 0.000 description 1
- VQIJPGFKPUSCCG-UHFFFAOYSA-N 2-phenyl-1-sulfanylanthracene-9,10-dione Chemical class C1=CC=2C(=O)C3=CC=CC=C3C(=O)C=2C(S)=C1C1=CC=CC=C1 VQIJPGFKPUSCCG-UHFFFAOYSA-N 0.000 description 1
- UMIFTERTMPEPIA-UHFFFAOYSA-N 3,9-bis(4-phenoxyanilino)benzo[b]phenalen-7-one Chemical compound C=1C=C2C(C=34)=CC=C(NC=5C=CC(OC=6C=CC=CC=6)=CC=5)C4=CC=CC=3C(=O)C2=CC=1NC(C=C1)=CC=C1OC1=CC=CC=C1 UMIFTERTMPEPIA-UHFFFAOYSA-N 0.000 description 1
- MVHIYIAUSAOOGX-UHFFFAOYSA-N 3,9-dianilinobenzo[b]phenalen-7-one Chemical compound C=1C=C2C(C=34)=CC=C(NC=5C=CC=CC=5)C4=CC=CC=3C(=O)C2=CC=1NC1=CC=CC=C1 MVHIYIAUSAOOGX-UHFFFAOYSA-N 0.000 description 1
- NJRDKTCOULEHNP-UHFFFAOYSA-N 3-methyl-6-(4-methylanilino)naphtho[3,2-f]quinoline-2,7-dione Chemical compound C=12C(=O)C3=CC=CC=C3C=C2C2=CC(=O)C(C)=NC2=CC=1NC1=CC=C(C)C=C1 NJRDKTCOULEHNP-UHFFFAOYSA-N 0.000 description 1
- OKWBRVDLEUCWPZ-UHFFFAOYSA-N 5-(4-benzylanilino)-1,4-dihydroxyanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C=3C(O)=CC=C(O)C=3C(=O)C2=C1NC(C=C1)=CC=C1CC1=CC=CC=C1 OKWBRVDLEUCWPZ-UHFFFAOYSA-N 0.000 description 1
- IINUILUUARLUBD-UHFFFAOYSA-N 5-[4-(benzenesulfonyl)anilino]-1,4-dihydroxyanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C=3C(O)=CC=C(O)C=3C(=O)C2=C1NC(C=C1)=CC=C1S(=O)(=O)C1=CC=CC=C1 IINUILUUARLUBD-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 229920001634 Copolyester Polymers 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- 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 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- CHAZWGWARFFSQA-UHFFFAOYSA-N N-(4-chlorophenyl)naphtho[7,6-f]quinazolin-11-amine Chemical compound C1=CC(Cl)=CC=C1NC1=CC=CC2=CC3=CC=C(N=CN=C4)C4=C3C=C12 CHAZWGWARFFSQA-UHFFFAOYSA-N 0.000 description 1
- FMGWFYWUYFJSNB-UHFFFAOYSA-N N-(4-methylphenyl)naphtho[7,6-f]quinazolin-11-amine Chemical compound C1=CC(C)=CC=C1NC1=CC=CC2=CC3=CC=C(N=CN=C4)C4=C3C=C12 FMGWFYWUYFJSNB-UHFFFAOYSA-N 0.000 description 1
- ZGFDOSYOLWQPIM-UHFFFAOYSA-N N-(4-phenoxyphenyl)-2-phenyl-1H-naphtho[7,6-f]quinazolin-11-amine Chemical compound C12=CC3=C4CN(C=5C=CC=CC=5)C=NC4=CC=C3C=C2C=CC=C1NC(C=C1)=CC=C1OC1=CC=CC=C1 ZGFDOSYOLWQPIM-UHFFFAOYSA-N 0.000 description 1
- FRQVTVGYMHRJQF-UHFFFAOYSA-N N-(4-phenoxyphenyl)naphtho[7,6-f]quinazolin-11-amine Chemical compound C=1C=CC2=CC3=CC=C4N=CN=CC4=C3C=C2C=1NC(C=C1)=CC=C1OC1=CC=CC=C1 FRQVTVGYMHRJQF-UHFFFAOYSA-N 0.000 description 1
- HGUMYMRHRBCLIU-UHFFFAOYSA-N N1=CC=CC2=C(C=C3C(CC(C=C3)=O)=C3)C3=CC=C21 Chemical compound N1=CC=CC2=C(C=C3C(CC(C=C3)=O)=C3)C3=CC=C21 HGUMYMRHRBCLIU-UHFFFAOYSA-N 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 229920002125 Sokalan® Chemical class 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 102100035115 Testin Human genes 0.000 description 1
- 101710070533 Testin Proteins 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 125000005599 alkyl carboxylate group Chemical group 0.000 description 1
- 229920003180 amino resin Polymers 0.000 description 1
- 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 description 1
- 239000001000 anthraquinone dye Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000005605 benzo group Chemical group 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
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 229920006217 cellulose acetate butyrate Polymers 0.000 description 1
- 229920001727 cellulose butyrate Polymers 0.000 description 1
- 229920003086 cellulose ether Polymers 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- SURLGNKAQXKNSP-DBLYXWCISA-N chlorin Chemical compound C\1=C/2\N/C(=C\C3=N/C(=C\C=4NC(/C=C\5/C=CC/1=N/5)=CC=4)/C=C3)/CC\2 SURLGNKAQXKNSP-DBLYXWCISA-N 0.000 description 1
- QBWCMBCROVPCKQ-UHFFFAOYSA-N chlorous acid Chemical compound OCl=O QBWCMBCROVPCKQ-UHFFFAOYSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 125000000950 dibromo group Chemical group Br* 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 125000005113 hydroxyalkoxy group Chemical group 0.000 description 1
- 150000005165 hydroxybenzoic acids Chemical class 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 150000002505 iron Chemical class 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- BLZZOMHXWLCYKG-UHFFFAOYSA-N n,2-diphenyl-1h-naphtho[7,6-f]quinazolin-11-amine Chemical compound C12=CC3=C4CN(C=5C=CC=CC=5)C=NC4=CC=C3C=C2C=CC=C1NC1=CC=CC=C1 BLZZOMHXWLCYKG-UHFFFAOYSA-N 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-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
- 239000000025 natural resin Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004584 polyacrylic acid Chemical class 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 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
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- TVRGPOFMYCMNRB-UHFFFAOYSA-N quinizarine green ss Chemical compound C1=CC(C)=CC=C1NC(C=1C(=O)C2=CC=CC=C2C(=O)C=11)=CC=C1NC1=CC=C(C)C=C1 TVRGPOFMYCMNRB-UHFFFAOYSA-N 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 210000001550 testis Anatomy 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
- C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
- C09B5/02—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic ring being only condensed in peri position
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0041—Optical brightening agents, organic pigments
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/37—Thiols
- C08K5/375—Thiols containing six-membered aromatic 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
- C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
- C09B1/32—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups
-
- 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
- C09B1/42—Dyes with acylated amino groups the acyl groups being residues of an aromatic carboxylic acid
-
- 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
- C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
-
- 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
- C09B1/56—Mercapto-anthraquinones
- C09B1/58—Mercapto-anthraquinones with mercapto groups substituted by aliphatic, cycloaliphatic, araliphatic or aryl radicals
- C09B1/585—Mercapto-anthraquinones with mercapto groups substituted by aliphatic, cycloaliphatic, araliphatic or aryl radicals substituted by aryl radicals
-
- 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
- C09B3/02—Benzathrones
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/933—Thermosol dyeing, thermofixation or dry heat fixation or development
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Coloring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1439373A CH581166A5 (en, 2012) | 1973-10-10 | 1973-10-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1045133A true CA1045133A (en) | 1978-12-26 |
Family
ID=4400438
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA211,018A Expired CA1045133A (en) | 1973-10-10 | 1974-10-08 | Process for the manufacture of halogen-containing anthraquinoidal compounds, their use and new halogen-containing anthraquinoidal compounds |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US3975410A (en, 2012) |
| JP (1) | JPS5855985B2 (en, 2012) |
| AR (1) | AR206901A1 (en, 2012) |
| BE (1) | BE820847A (en, 2012) |
| CA (1) | CA1045133A (en, 2012) |
| CH (1) | CH581166A5 (en, 2012) |
| CS (1) | CS183764B2 (en, 2012) |
| DE (2) | DE2447708C3 (en, 2012) |
| ES (1) | ES430812A1 (en, 2012) |
| FR (1) | FR2247449B1 (en, 2012) |
| GB (1) | GB1465992A (en, 2012) |
| NL (1) | NL7413350A (en, 2012) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4128396A (en) * | 1973-10-10 | 1978-12-05 | Ciba-Geigy Corporation | Process for the improvement of dyeing properties of pigments of the anilino and arylmercapto anthraquinone series |
| CH616442A5 (en, 2012) * | 1975-07-23 | 1980-03-31 | Ciba Geigy Ag | |
| US4743642A (en) * | 1986-09-08 | 1988-05-10 | The Dow Chemical Company | Color balanced rubber-reinforced plastic |
| JP2001187844A (ja) * | 1999-12-29 | 2001-07-10 | Ciba Specialty Chem Holding Inc | 合成材料の練り込み着色のための新規顔料着色剤 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2128178A (en) * | 1936-11-23 | 1938-08-23 | Du Pont | Process for the chlorination of aminoanthraquinone compounds |
| US2226909A (en) * | 1936-12-30 | 1940-12-31 | Sandoz Ltd | Anthraquinone dyestuffs and a process for their manufacture |
| US2236672A (en) * | 1937-05-04 | 1941-04-01 | Ici Ltd | Brominated arylaminoanthraquinone compounds |
| NL290564A (en, 2012) * | 1963-02-11 | |||
| US3378572A (en) * | 1964-01-28 | 1968-04-16 | Du Pont | Chlorination of anthraquinone-sulfonic acids using nascent chlorine and an inorganicammonium salt(added slowly) in dilute sulfuric acid |
| US3530151A (en) * | 1964-05-01 | 1970-09-22 | Allied Chem | Halogenation process |
| US3507606A (en) | 1966-09-27 | 1970-04-21 | Toms River Chemical Corp | Acylphenylaminoanthraquinone dyes for linear polyester materials |
| GB1238372A (en, 2012) * | 1968-03-25 | 1971-07-07 | ||
| DE2122232C3 (de) * | 1970-05-16 | 1974-12-05 | Sumitomo Chemical Co., Ltd., Osaka (Japan) | Anthrachinonverbindungen, Verfahren zu deren Herstellung und deren Verwendung |
| GB1426332A (en) * | 1972-05-19 | 1976-02-25 | Basf Ag | Blue anthraquinoid acid dyes |
| US3797995A (en) * | 1972-10-02 | 1974-03-19 | American Aniline Prod | Polyester textile fibers dyed with alpha-aminoanthraquinone dyes |
-
1973
- 1973-10-10 CH CH1439373A patent/CH581166A5/xx not_active IP Right Cessation
-
1974
- 1974-01-01 AR AR255976A patent/AR206901A1/es active
- 1974-09-27 US US05/509,877 patent/US3975410A/en not_active Expired - Lifetime
- 1974-10-07 DE DE2447708A patent/DE2447708C3/de not_active Expired
- 1974-10-07 DE DE2462717A patent/DE2462717C2/de not_active Expired
- 1974-10-08 CA CA211,018A patent/CA1045133A/en not_active Expired
- 1974-10-09 FR FR7433975A patent/FR2247449B1/fr not_active Expired
- 1974-10-09 JP JP49116782A patent/JPS5855985B2/ja not_active Expired
- 1974-10-09 ES ES430812A patent/ES430812A1/es not_active Expired
- 1974-10-09 GB GB4366074A patent/GB1465992A/en not_active Expired
- 1974-10-09 BE BE149338A patent/BE820847A/xx unknown
- 1974-10-10 NL NL7413350A patent/NL7413350A/xx not_active Application Discontinuation
- 1974-10-10 CS CS7400006953A patent/CS183764B2/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL7413350A (nl) | 1975-04-14 |
| CS183764B2 (en) | 1978-07-31 |
| DE2447708C3 (de) | 1979-10-04 |
| CH581166A5 (en, 2012) | 1976-10-29 |
| JPS5066527A (en, 2012) | 1975-06-04 |
| DE2462717C2 (de) | 1980-07-10 |
| JPS5855985B2 (ja) | 1983-12-13 |
| ES430812A1 (es) | 1976-09-16 |
| BE820847A (fr) | 1975-04-09 |
| DE2447708A1 (de) | 1975-04-17 |
| GB1465992A (en) | 1977-03-02 |
| AR206901A1 (es) | 1976-08-31 |
| AU7412974A (en) | 1976-04-15 |
| US3975410A (en) | 1976-08-17 |
| DE2447708B2 (de) | 1979-02-08 |
| DE2462717B1 (de) | 1979-10-31 |
| FR2247449A1 (en, 2012) | 1975-05-09 |
| FR2247449B1 (en, 2012) | 1976-10-22 |
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