JPS609061B2 - クロム錯体染料の製造法 - Google Patents

クロム錯体染料の製造法

Info

Publication number: JPS609061B2
Authority: JP; Japan
Prior art keywords: dye; chromium; parts; weight; alkylene
Prior art date: 1976-02-12
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

Application number

JP1315877A

Other languages

English (en)

Japanese (ja)

Other versions

JPS5298737A (en

Inventor

ビンフリ−ト・メンニツケ

バルタ−・シヨ−ル

カ−ル・ハインツ・シユンデヒユツテ

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Bayer AG

Original Assignee

Bayer AG

Priority date (The priority date 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 date listed.)

1976-02-12

Filing date

1977-02-10

Publication date

1985-03-07

1977-02-10 Application filed by Bayer AG filed Critical Bayer AG

1977-08-18 Publication of JPS5298737A publication Critical patent/JPS5298737A/ja

1985-03-07 Publication of JPS609061B2 publication Critical patent/JPS609061B2/ja

Status Expired legal-status Critical Current

Links

239000011651 chromium Substances 0.000 title claims description 55
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 title claims description 54
229910052804 chromium Inorganic materials 0.000 title claims description 53
238000004519 manufacturing process Methods 0.000 title claims description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 31
150000003839 salts Chemical class 0.000 claims description 25
239000003795 chemical substances by application Substances 0.000 claims description 15
POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 claims description 13
125000002947 alkylene group Chemical group 0.000 claims description 12
238000006243 chemical reaction Methods 0.000 claims description 9
230000018044 dehydration Effects 0.000 claims description 8
238000006297 dehydration reaction Methods 0.000 claims description 8
150000001844 chromium Chemical class 0.000 claims description 7
238000000034 method Methods 0.000 claims description 7
-1 and n is 1 to 5 Chemical group 0.000 claims description 6
150000001845 chromium compounds Chemical class 0.000 claims description 6
125000001931 aliphatic group Chemical group 0.000 claims description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
RMXTYBQNQCQHEU-UHFFFAOYSA-N ac1lawpn Chemical compound [Cr]#[Cr] RMXTYBQNQCQHEU-UHFFFAOYSA-N 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
239000000975 dye Substances 0.000 description 143
239000000203 mixture Substances 0.000 description 47
NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 31
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 26
239000000843 powder Substances 0.000 description 26
210000002268 wool Anatomy 0.000 description 23
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 19
238000001914 filtration Methods 0.000 description 18
238000010992 reflux Methods 0.000 description 16
238000003756 stirring Methods 0.000 description 16
150000001875 compounds Chemical class 0.000 description 13
229910000030 sodium bicarbonate Inorganic materials 0.000 description 13
235000017557 sodium bicarbonate Nutrition 0.000 description 13
JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 12
239000002904 solvent Substances 0.000 description 10
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 9
239000004952 Polyamide Substances 0.000 description 8
238000005352 clarification Methods 0.000 description 8
238000004043 dyeing Methods 0.000 description 8
229920002647 polyamide Polymers 0.000 description 8
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 6
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 6
239000005977 Ethylene Substances 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
239000010985 leather Substances 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
238000004532 chromating Methods 0.000 description 5
238000001816 cooling Methods 0.000 description 5
238000001465 metallisation Methods 0.000 description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
229910052783 alkali metal Inorganic materials 0.000 description 4
150000007524 organic acids Chemical class 0.000 description 4
235000005985 organic acids Nutrition 0.000 description 4
239000000047 product Substances 0.000 description 4
125000000542 sulfonic acid group Chemical group 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
238000004821 distillation Methods 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
239000007921 spray Substances 0.000 description 3
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 2
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
239000000370 acceptor Substances 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
239000000654 additive Substances 0.000 description 2
229910000288 alkali metal carbonate Inorganic materials 0.000 description 2
150000008041 alkali metal carbonates Chemical class 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
238000010533 azeotropic distillation Methods 0.000 description 2
238000009835 boiling Methods 0.000 description 2
VQWFNAGFNGABOH-UHFFFAOYSA-K chromium(iii) hydroxide Chemical compound [OH-].[OH-].[OH-].[Cr+3] VQWFNAGFNGABOH-UHFFFAOYSA-K 0.000 description 2
235000019646 color tone Nutrition 0.000 description 2
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
239000003792 electrolyte Substances 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
150000004679 hydroxides Chemical class 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000000463 material Substances 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
239000001044 red dye Substances 0.000 description 2
229910052709 silver Inorganic materials 0.000 description 2
239000004332 silver Substances 0.000 description 2
239000011734 sodium Substances 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 1
SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
COBPKKZHLDDMTB-UHFFFAOYSA-N 2-[2-(2-butoxyethoxy)ethoxy]ethanol Chemical compound CCCCOCCOCCOCCO COBPKKZHLDDMTB-UHFFFAOYSA-N 0.000 description 1
YEYKMVJDLWJFOA-UHFFFAOYSA-N 2-propoxyethanol Chemical compound CCCOCCO YEYKMVJDLWJFOA-UHFFFAOYSA-N 0.000 description 1
DVFGEIYOLIFSRX-UHFFFAOYSA-N 3-(2-ethylhexoxy)propan-1-amine Chemical compound CCCCC(CC)COCCCN DVFGEIYOLIFSRX-UHFFFAOYSA-N 0.000 description 1
235000017166 Bambusa arundinacea Nutrition 0.000 description 1
235000017491 Bambusa tulda Nutrition 0.000 description 1
241001330002 Bambuseae Species 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
101100258315 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) crc-1 gene Proteins 0.000 description 1
235000015334 Phyllostachys viridis Nutrition 0.000 description 1
241000270666 Testudines Species 0.000 description 1
MPHOYESWVFOEGJ-UHFFFAOYSA-N [Cr].[Pb] Chemical compound [Cr].[Pb] MPHOYESWVFOEGJ-UHFFFAOYSA-N 0.000 description 1
125000004442 acylamino group Chemical group 0.000 description 1
238000007259 addition reaction Methods 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
239000011425 bamboo Substances 0.000 description 1
239000002585 base Substances 0.000 description 1
125000002843 carboxylic acid group Chemical group 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical compound [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 description 1
NFTADESQVWCREX-UHFFFAOYSA-L chromium(3+);carbonate Chemical compound [Cr+3].[O-]C([O-])=O NFTADESQVWCREX-UHFFFAOYSA-L 0.000 description 1
239000003086 colorant Substances 0.000 description 1
229940125833 compound 23 Drugs 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
229940028356 diethylene glycol monobutyl ether Drugs 0.000 description 1
XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
239000000428 dust Substances 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
239000000835 fiber Substances 0.000 description 1
239000002657 fibrous material Substances 0.000 description 1
235000013312 flour Nutrition 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
239000001046 green dye Substances 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000004922 lacquer Substances 0.000 description 1
XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
229910052808 lithium carbonate Inorganic materials 0.000 description 1
229910003002 lithium salt Inorganic materials 0.000 description 1
159000000002 lithium salts Chemical class 0.000 description 1
239000008267 milk Substances 0.000 description 1
210000004080 milk Anatomy 0.000 description 1
235000013336 milk Nutrition 0.000 description 1
238000002156 mixing Methods 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
239000012465 retentate Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000011343 solid material Substances 0.000 description 1
238000003860 storage Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
238000000967 suction filtration Methods 0.000 description 1
229940124530 sulfonamide Drugs 0.000 description 1
150000003456 sulfonamides Chemical class 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 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
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/01—Complex metal compounds of azo dyes characterised by the method of metallisation

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Coloring (AREA)
Inorganic Compounds Of Heavy Metals (AREA)

JP1315877A 1976-02-12 1977-02-10 クロム錯体染料の製造法 Expired JPS609061B2 (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE2605574.3		1976-02-12
DE19762605574 DE2605574C2 (de)	1976-02-12	1976-02-12	Verfahren zur Herstellung von Chrom- und Kobaltkomplexfarbstoffen und deren Lösungen

Publications (2)

Publication Number	Publication Date
JPS5298737A JPS5298737A (en)	1977-08-18
JPS609061B2 true JPS609061B2 (ja)	1985-03-07

Family

ID=5969709

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP1315877A Expired JPS609061B2 (ja)	1976-02-12	1977-02-10	クロム錯体染料の製造法

Country Status (8)

Country	Link
JP (1)	JPS609061B2 (fr)
BE (1)	BE851283A (fr)
BR (1)	BR7700783A (fr)
CH (1)	CH624978A5 (fr)
DE (1)	DE2605574C2 (fr)
ES (1)	ES455712A1 (fr)
FR (1)	FR2340970A1 (fr)
GB (1)	GB1567691A (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2918634A1 (de) *	1979-05-09	1980-11-20	Basf Ag	Verfahren zur herstellung von kobalt- und chrom-1 zu 2-komplexfarbstoffen
DE2934015A1 (de) *	1979-08-22	1981-03-26	Bayer Ag, 51373 Leverkusen	Verfahren zur herstellung von konzentrierten loesungen sulfogruppenfreier 1 zu 2-cr- bzw. 1 zu 2-co-komplexfarbstoffe
JPS5993457A (ja) *	1982-11-19	1984-05-29	Nippon Kayaku Co Ltd	電子写真印刷用トナ−
DE19905279A1 (de) *	1999-02-09	2000-08-10	Bayer Ag	Verwendung flüssiger Farbstoffpräparationen zum Färben von Holz
JP7283249B2 (ja) *	2019-06-19	2023-05-30	セイコーエプソン株式会社	水系インクジェット捺染インク組成物及び捺染方法

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR1360942A (fr) *	1962-02-09	1964-05-15	Acna	Colorants métallisés et procédé pour leur obtention
BE633273A (fr) *	1963-06-18
NL7205191A (fr) *	1971-04-23	1972-10-25
NL7317211A (fr) *	1972-12-22	1974-06-25
CH599308A5 (fr) *	1974-07-05	1978-05-31	Ciba Geigy Ag

1976
- 1976-02-12 DE DE19762605574 patent/DE2605574C2/de not_active Expired
1977
- 1977-02-08 CH CH151277A patent/CH624978A5/de not_active IP Right Cessation
- 1977-02-08 ES ES455712A patent/ES455712A1/es not_active Expired
- 1977-02-09 GB GB530277A patent/GB1567691A/en not_active Expired
- 1977-02-09 BR BR7700783A patent/BR7700783A/pt unknown
- 1977-02-10 BE BE174809A patent/BE851283A/fr unknown
- 1977-02-10 JP JP1315877A patent/JPS609061B2/ja not_active Expired
- 1977-02-11 FR FR7703963A patent/FR2340970A1/fr active Granted

Also Published As

Publication number	Publication date
FR2340970B1 (fr)	1981-01-09
JPS5298737A (en)	1977-08-18
DE2605574C2 (de)	1984-01-12
GB1567691A (en)	1980-05-21
BE851283A (fr)	1977-08-10
BR7700783A (pt)	1977-10-11
FR2340970A1 (fr)	1977-09-09
ES455712A1 (es)	1978-04-16
DE2605574A1 (de)	1977-08-18
CH624978A5 (en)	1981-08-31

Publication	Publication Date	Title
US4085097A (en)	1978-04-18	Process for the manufacture of chromium complexes from metallizable azo or azo methine dyes
US2933489A (en)	1960-04-19	Heavy metal-containing dyestuffs
DE859343C (de)	1952-12-15	Verfahren zur Herstellung von Azofarbstoffen
JPS609061B2 (ja)	1985-03-07	クロム錯体染料の製造法
JPS6058260B2 (ja)	1985-12-19	アントラキノン化合物、その製法および染色方法
JPS5828301B2 (ja)	1983-06-15	クロムサクエンセンリヨウノセイゾウホウホウ
US4362873A (en)	1982-12-07	Process for the preparation of basic oxazine dyestuffs
JPS6020420B2 (ja)	1985-05-22	アゾ化合物の製法
DE748913C (de)	1944-11-23	Verfahren zur Herstellung von metallhaltigen Azofarbstoffen
JPS61264060A (ja)	1986-11-21	トリスアゾ黒染料
DE643164C (de)	1937-03-31	Verfahren zur Herstellung von Anthrachinonfarbstoffen
EP0532994A1 (fr)	1993-03-24	Colorants de type complexe de chrome 1:2 asymétrique
EP0024609B1 (fr)	1983-01-12	Procédé de préparation de solutions concentrées de colorants complexes de metal sans groupes sulfoniques
DE2608535C2 (de)	1986-04-30	Neue Chromkomplexfarbstoffe, ihre Herstellung und Verwendung
US4426205A (en)	1984-01-17	Novel red dyes for fiberglass and paper
DE858438C (de)	1952-12-08	Verfahren zur Herstellung von kupferhaltigen Disazofarbstoffen
EP0073377B1 (fr)	1985-11-21	Colorants complexes 1:2 chromifères asymétriques et procédé de préparation et de teinture
DE657628C (de)	1938-03-09	Herstellung von Farbstoffen
KR810001493B1 (ko)	1981-10-24	금속 착화합물 반응성 염료의 제조방법
JPS5880351A (ja)	1983-05-14	反応性アントラキノン染料、その製法及び含窒素材料の染色および捺染のための使用
DE745458C (de)	1944-03-13	Verfahren zur Herstellung von 0-Oxyazofarbstoffen
DE2623361A1 (de)	1977-12-15	Reaktivfarbstoffe
JP2001518531A (ja)	2001-10-16	アルミニウムアルキルアセトアセテート化合物及びその製法と印刷インキ付加剤としての使用
AT167616B (de)	1951-02-10	Verfahren zur Herstellung von neuen Azofarbstoffen
JP2004517228A (ja)	2004-06-10	天然材料および合成材料を染色するためのジスアゾ染料の銅錯体の使用