CN101195581A - 取代的氨基蒽醌的制备 - Google Patents
取代的氨基蒽醌的制备 Download PDFInfo
- Publication number
- CN101195581A CN101195581A CNA2007101947812A CN200710194781A CN101195581A CN 101195581 A CN101195581 A CN 101195581A CN A2007101947812 A CNA2007101947812 A CN A2007101947812A CN 200710194781 A CN200710194781 A CN 200710194781A CN 101195581 A CN101195581 A CN 101195581A
- Authority
- CN
- China
- Prior art keywords
- alkyl
- chemical formula
- represent
- group
- quinizarin
- 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.)
- Pending
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- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical class O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 title claims abstract description 12
- 238000002360 preparation method Methods 0.000 title description 8
- GUEIZVNYDFNHJU-UHFFFAOYSA-N quinizarin Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=CC=C2O GUEIZVNYDFNHJU-UHFFFAOYSA-N 0.000 claims abstract description 133
- 238000000034 method Methods 0.000 claims abstract description 43
- 150000001412 amines Chemical class 0.000 claims abstract description 21
- 238000004043 dyeing Methods 0.000 claims abstract description 6
- 239000004033 plastic Substances 0.000 claims abstract description 5
- 229920003023 plastic Polymers 0.000 claims abstract description 5
- -1 boric acid ester Chemical class 0.000 claims description 61
- 239000000126 substance Substances 0.000 claims description 53
- 239000004327 boric acid Substances 0.000 claims description 39
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 34
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 21
- 229910052736 halogen Inorganic materials 0.000 claims description 17
- 150000002367 halogens Chemical class 0.000 claims description 17
- 239000004310 lactic acid Substances 0.000 claims description 17
- 235000014655 lactic acid Nutrition 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 16
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 239000000975 dye Substances 0.000 claims description 13
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 11
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 claims description 11
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 7
- 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 7
- 229960001156 mitoxantrone Drugs 0.000 claims description 7
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 150000004982 aromatic amines Chemical class 0.000 claims description 5
- 125000000217 alkyl group Chemical class 0.000 claims description 4
- CUBCNYWQJHBXIY-UHFFFAOYSA-N benzoic acid;2-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=CC=C1.OC(=O)C1=CC=CC=C1O CUBCNYWQJHBXIY-UHFFFAOYSA-N 0.000 claims description 4
- 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 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- LGQXXHMEBUOXRP-UHFFFAOYSA-N tributyl borate Chemical compound CCCCOB(OCCCC)OCCCC LGQXXHMEBUOXRP-UHFFFAOYSA-N 0.000 claims description 4
- AJSTXXYNEIHPMD-UHFFFAOYSA-N triethyl borate Chemical compound CCOB(OCC)OCC AJSTXXYNEIHPMD-UHFFFAOYSA-N 0.000 claims description 4
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 claims description 3
- DBXBTMSZEOQQDU-UHFFFAOYSA-N 3-hydroxyisobutyric acid Chemical compound OCC(C)C(O)=O DBXBTMSZEOQQDU-UHFFFAOYSA-N 0.000 claims description 2
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 2
- 235000019445 benzyl alcohol Nutrition 0.000 claims description 2
- 229960004217 benzyl alcohol Drugs 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 2
- 150000003142 primary aromatic amines Chemical class 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 229940095064 tartrate Drugs 0.000 claims description 2
- NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 claims 1
- 239000002904 solvent Substances 0.000 abstract description 18
- 238000005187 foaming Methods 0.000 abstract description 10
- 239000006227 byproduct Substances 0.000 abstract description 5
- 230000035484 reaction time Effects 0.000 abstract description 5
- 150000002148 esters Chemical class 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 229920002994 synthetic fiber Polymers 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 63
- 239000000203 mixture Substances 0.000 description 47
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- 238000009833 condensation Methods 0.000 description 17
- 230000005494 condensation Effects 0.000 description 17
- 239000000843 powder Substances 0.000 description 17
- 238000010438 heat treatment Methods 0.000 description 14
- 229910052757 nitrogen Inorganic materials 0.000 description 14
- 238000004809 thin layer chromatography Methods 0.000 description 13
- AQXYVFBSOOBBQV-UHFFFAOYSA-N 1-amino-4-hydroxyanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=CC=C2N AQXYVFBSOOBBQV-UHFFFAOYSA-N 0.000 description 9
- 238000000967 suction filtration Methods 0.000 description 9
- 238000007689 inspection Methods 0.000 description 8
- 238000001291 vacuum drying Methods 0.000 description 8
- 238000009835 boiling Methods 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- JJVKJJNCIILLRP-UHFFFAOYSA-N 2-ethyl-6-methylaniline Chemical compound CCC1=CC=CC(C)=C1N JJVKJJNCIILLRP-UHFFFAOYSA-N 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- FBMQNRKSAWNXBT-UHFFFAOYSA-N 1,4-diaminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(N)=CC=C2N FBMQNRKSAWNXBT-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000012752 auxiliary agent Substances 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000002798 polar solvent Substances 0.000 description 3
- BTLXPCBPYBNQNR-UHFFFAOYSA-N 1-hydroxyanthraquinone Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2O BTLXPCBPYBNQNR-UHFFFAOYSA-N 0.000 description 2
- CZZZABOKJQXEBO-UHFFFAOYSA-N 2,4-dimethylaniline Chemical group CC1=CC=C(N)C(C)=C1 CZZZABOKJQXEBO-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 230000006837 decompression Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- KWVPRPSXBZNOHS-UHFFFAOYSA-N 2,4,6-Trimethylaniline Chemical compound CC1=CC(C)=C(N)C(C)=C1 KWVPRPSXBZNOHS-UHFFFAOYSA-N 0.000 description 1
- OIXUMNZGNCAOKY-UHFFFAOYSA-N 2,6-diethyl-4-methylaniline Chemical compound CCC1=CC(C)=CC(CC)=C1N OIXUMNZGNCAOKY-UHFFFAOYSA-N 0.000 description 1
- UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical group CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 description 1
- MKARNSWMMBGSHX-UHFFFAOYSA-N 3,5-dimethylaniline Chemical group CC1=CC(C)=CC(N)=C1 MKARNSWMMBGSHX-UHFFFAOYSA-N 0.000 description 1
- CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 description 1
- WRDWWAVNELMWAM-UHFFFAOYSA-N 4-tert-butylaniline Chemical compound CC(C)(C)C1=CC=C(N)C=C1 WRDWWAVNELMWAM-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 229960001413 acetanilide Drugs 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-N benzene-dicarboxylic acid Natural products OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 1
- 239000001045 blue dye Substances 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical class CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 1
- 229930188620 butyrolactone Natural products 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- HFXKQSZZZPGLKQ-UHFFFAOYSA-N cyclopentamine Chemical compound CNC(C)CC1CCCC1 HFXKQSZZZPGLKQ-UHFFFAOYSA-N 0.000 description 1
- 229960003263 cyclopentamine Drugs 0.000 description 1
- 238000006392 deoxygenation reaction Methods 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 230000009931 harmful effect Effects 0.000 description 1
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- CSMWJXBSXGUPGY-UHFFFAOYSA-L sodium dithionate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)S([O-])(=O)=O CSMWJXBSXGUPGY-UHFFFAOYSA-L 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 210000002268 wool 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
- 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
- C09B1/325—Dyes with no other substituents than the amino groups
-
- 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
- C08K5/17—Amines; Quaternary ammonium compounds
- C08K5/18—Amines; Quaternary ammonium compounds with aromatically bound amino 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
- C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
- C09B1/28—Dyes with amino groups substituted by hydrocarbon radicals substituted by alkyl, aralkyl or cyclo alkyl groups
- C09B1/285—Dyes with no other substituents than the amino 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
- C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
- C09B1/51—N-substituted amino-hydroxy anthraquinone
- C09B1/514—N-aryl derivatives
- C09B1/5145—N-aryl derivatives only amino and hydroxy groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Coloring (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102006057652A DE102006057652A1 (de) | 2006-12-07 | 2006-12-07 | Verfahren zur Herstellung von substituierten Aminoanthrachinonen |
| DE102006057652.7 | 2006-12-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN101195581A true CN101195581A (zh) | 2008-06-11 |
Family
ID=39272062
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNA2007101947812A Pending CN101195581A (zh) | 2006-12-07 | 2007-12-06 | 取代的氨基蒽醌的制备 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US20080139830A1 (enExample) |
| EP (1) | EP1930377A3 (enExample) |
| JP (1) | JP2008156631A (enExample) |
| CN (1) | CN101195581A (enExample) |
| DE (1) | DE102006057652A1 (enExample) |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104530745A (zh) * | 2014-12-19 | 2015-04-22 | 江苏道博化工有限公司 | 一种制备溶剂紫38的方法 |
| CN105237417A (zh) * | 2015-09-17 | 2016-01-13 | 江苏道博化工有限公司 | 一种溶剂紫13的合成方法 |
| CN104341790B (zh) * | 2014-09-25 | 2017-03-29 | 宁波龙欣精细化工有限公司 | 纯化的1‑羟基‑4‑芳胺基蒽醌产品及其制备方法 |
| CN106675081A (zh) * | 2017-01-16 | 2017-05-17 | 铜陵清华科技有限公司 | 一种溶剂蓝104染料的环保制备方法 |
| CN107501987A (zh) * | 2017-08-26 | 2017-12-22 | 宁波德欣科技有限公司 | 一种1‑羟基‑4‑对甲苯胺基蒽醌的制备方法 |
| CN108017935A (zh) * | 2017-12-26 | 2018-05-11 | 江苏道博化工有限公司 | 蓝色混合染料及其制备方法 |
| CN108395381A (zh) * | 2018-04-10 | 2018-08-14 | 大连傲视化学有限公司 | 1,4-二氨基蒽醌隐色体的合成方法 |
| CN110615741A (zh) * | 2019-09-24 | 2019-12-27 | 安徽清科瑞洁新材料有限公司 | 一种低毒低害环保型溶剂绿3的合成方法 |
| CN110713732A (zh) * | 2019-10-18 | 2020-01-21 | 湖北彩德新材料科技有限公司 | 一种溶剂颜料5b绿及其制备方法 |
| CN112322067A (zh) * | 2020-11-04 | 2021-02-05 | 罗子木 | 一种塑料着色剂紫b及其制备方法 |
| CN114315607A (zh) * | 2021-12-29 | 2022-04-12 | 万华化学集团股份有限公司 | 一种二元仲胺的制备方法 |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20100016468A1 (en) * | 2008-07-17 | 2010-01-21 | Bergstrom Todd B | Treated expanded polystyrene foam |
| CN104277494A (zh) * | 2014-09-27 | 2015-01-14 | 无锡市东北塘宏良染色厂 | 一种酸性染料 |
| US9272981B1 (en) * | 2015-06-23 | 2016-03-01 | Amazon Technologies, Inc. | Method of preparing a compound |
| SE544071C2 (en) | 2020-04-21 | 2021-12-07 | Assa Abloy Ab | Bumping preventing arrangement for lock device, lock device and method |
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| DE631518C (de) | 1934-03-22 | 1936-06-22 | Chem Fab Vormals Sandoz | Verfahren zur Herstellung von Farbstoffen der Anthrachinonreihe |
| NL273182A (enExample) * | 1961-01-05 | |||
| GB1074829A (en) * | 1964-06-08 | 1967-07-05 | Ici Ltd | Anthraquinone dyestuffs |
| GB1114936A (en) * | 1965-07-19 | 1968-05-22 | Ici Ltd | Process for mass coloring polyesters |
| JPS499535A (enExample) * | 1972-05-23 | 1974-01-28 | ||
| JPS5133724B2 (enExample) * | 1972-08-05 | 1976-09-21 | ||
| GB1444716A (en) | 1972-08-24 | 1976-08-04 | Clayton Aniline Co Ltd | Dyestuff preparations |
| US4083683A (en) * | 1977-03-11 | 1978-04-11 | American Color & Chemical Corporation | Metal-containing polypropylene dyed with 1,4-bis-(2'-methyl-6'-ethylanilino)anthraquinone |
| DE19523851A1 (de) * | 1995-06-30 | 1997-01-02 | Basf Ag | Verfahren zur Herstellung von Mischungen aus Diphenylmethan-diisocyanaten und Polyphenyl-polymethylen-polyisocyanaten mit einer verminderten Iodfarbzahl und einem reduzierten Chlorgehalt |
| DE10140107B4 (de) * | 2001-08-16 | 2006-07-06 | Lanxess Deutschland Gmbh | Verfahren zur Herstellung von 1-Amino-4-hydroxyanthrachinonen |
| DE10222819A1 (de) | 2002-05-21 | 2003-12-04 | Bayer Ag | Verfahren zur Herstellung von N,N'-disubstituierten 1,4-Diaminoanthrachinonen |
-
2006
- 2006-12-07 DE DE102006057652A patent/DE102006057652A1/de not_active Withdrawn
-
2007
- 2007-11-30 US US11/998,701 patent/US20080139830A1/en not_active Abandoned
- 2007-12-04 EP EP07122286A patent/EP1930377A3/de not_active Withdrawn
- 2007-12-06 JP JP2007315998A patent/JP2008156631A/ja not_active Withdrawn
- 2007-12-06 CN CNA2007101947812A patent/CN101195581A/zh active Pending
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| CN104341790B (zh) * | 2014-09-25 | 2017-03-29 | 宁波龙欣精细化工有限公司 | 纯化的1‑羟基‑4‑芳胺基蒽醌产品及其制备方法 |
| CN104530745B (zh) * | 2014-12-19 | 2017-02-01 | 江苏道博化工有限公司 | 一种制备溶剂紫38的方法 |
| CN104530745A (zh) * | 2014-12-19 | 2015-04-22 | 江苏道博化工有限公司 | 一种制备溶剂紫38的方法 |
| CN105237417A (zh) * | 2015-09-17 | 2016-01-13 | 江苏道博化工有限公司 | 一种溶剂紫13的合成方法 |
| CN105237417B (zh) * | 2015-09-17 | 2017-05-17 | 江苏道博化工有限公司 | 一种溶剂紫13的合成方法 |
| CN106675081A (zh) * | 2017-01-16 | 2017-05-17 | 铜陵清华科技有限公司 | 一种溶剂蓝104染料的环保制备方法 |
| CN106675081B (zh) * | 2017-01-16 | 2019-04-02 | 安徽清科瑞洁新材料有限公司 | 一种溶剂蓝104染料的环保制备方法 |
| CN107501987A (zh) * | 2017-08-26 | 2017-12-22 | 宁波德欣科技有限公司 | 一种1‑羟基‑4‑对甲苯胺基蒽醌的制备方法 |
| CN108017935B (zh) * | 2017-12-26 | 2019-04-05 | 江苏道博化工有限公司 | 蓝色混合染料及其制备方法 |
| CN108017935A (zh) * | 2017-12-26 | 2018-05-11 | 江苏道博化工有限公司 | 蓝色混合染料及其制备方法 |
| CN108395381A (zh) * | 2018-04-10 | 2018-08-14 | 大连傲视化学有限公司 | 1,4-二氨基蒽醌隐色体的合成方法 |
| CN108395381B (zh) * | 2018-04-10 | 2020-09-22 | 大连傲视化学有限公司 | 1,4-二氨基蒽醌隐色体的合成方法 |
| CN110615741A (zh) * | 2019-09-24 | 2019-12-27 | 安徽清科瑞洁新材料有限公司 | 一种低毒低害环保型溶剂绿3的合成方法 |
| CN110713732A (zh) * | 2019-10-18 | 2020-01-21 | 湖北彩德新材料科技有限公司 | 一种溶剂颜料5b绿及其制备方法 |
| CN112322067A (zh) * | 2020-11-04 | 2021-02-05 | 罗子木 | 一种塑料着色剂紫b及其制备方法 |
| CN112322067B (zh) * | 2020-11-04 | 2022-06-10 | 罗子木 | 一种塑料着色剂紫b及其制备方法 |
| CN114315607A (zh) * | 2021-12-29 | 2022-04-12 | 万华化学集团股份有限公司 | 一种二元仲胺的制备方法 |
| CN114315607B (zh) * | 2021-12-29 | 2024-02-02 | 万华化学集团股份有限公司 | 一种二元仲胺的制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1930377A3 (de) | 2009-07-15 |
| EP1930377A2 (de) | 2008-06-11 |
| US20080139830A1 (en) | 2008-06-12 |
| JP2008156631A (ja) | 2008-07-10 |
| DE102006057652A1 (de) | 2008-06-12 |
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Application publication date: 20080611 |