CH405552A - Verfahren zur Herstellung von neuen wasserlöslichen Farbstoffen - Google Patents

Verfahren zur Herstellung von neuen wasserlöslichen Farbstoffen

Info

Publication number: CH405552A
Authority: CH; Switzerland
Prior art keywords: group; formula; acid group; triazine; contain
Prior art date: 1959-07-02

Application number

CH747665A

Other languages

German (de)

English (en)

Inventor

Durham Rattee Ian

Andrew Waite Frederick

Original Assignee

Ici Ltd

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.)

1959-07-02

Filing date

1960-07-01

Publication date

1966-01-15

1959-07-02 Priority claimed from GB22763/59A external-priority patent/GB929425A/en

1960-07-01 Application filed by Ici Ltd filed Critical Ici Ltd

1966-01-15 Publication of CH405552A publication Critical patent/CH405552A/de

Links

239000000975 dye Substances 0.000 title claims description 19
238000000034 method Methods 0.000 title claims description 10
125000004432 carbon atom Chemical group C* 0.000 claims description 10
125000000714 pyrimidinyl 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
229910052799 carbon Inorganic materials 0.000 claims description 7
230000008878 coupling Effects 0.000 claims description 7
238000010168 coupling process Methods 0.000 claims description 7
238000005859 coupling reaction Methods 0.000 claims description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
125000000542 sulfonic acid group Chemical group 0.000 claims description 6
125000002843 carboxylic acid group Chemical group 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
229930194542 Keto Natural products 0.000 claims description 3
125000003172 aldehyde group Chemical group 0.000 claims description 3
239000000987 azo dye Substances 0.000 claims description 3
150000008049 diazo compounds Chemical class 0.000 claims description 3
125000000468 ketone group Chemical group 0.000 claims description 3
229910052757 nitrogen Inorganic materials 0.000 claims description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims 2
-1 alkyl radical Chemical class 0.000 description 39
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
239000000243 solution Substances 0.000 description 8
239000004753 textile Substances 0.000 description 8
239000000203 mixture Substances 0.000 description 7
239000001913 cellulose Substances 0.000 description 6
229920002678 cellulose Polymers 0.000 description 6
239000000463 material Substances 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
230000002378 acidificating effect Effects 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
125000005843 halogen group Chemical group 0.000 description 4
150000003141 primary amines Chemical class 0.000 description 4
238000011282 treatment Methods 0.000 description 4
125000003363 1,3,5-triazinyl group Chemical group N1=C(N=CN=C1)* 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
125000003277 amino group Chemical group 0.000 description 3
238000004043 dyeing Methods 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
239000000725 suspension Substances 0.000 description 3
PKPZZAVJXDZHDW-LJTMIZJLSA-N (2r,3r,4r,5s)-6-(methylamino)hexane-1,2,3,4,5-pentol;hydrochloride Chemical compound Cl.CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO PKPZZAVJXDZHDW-LJTMIZJLSA-N 0.000 description 2
ZMCHBSMFKQYNKA-UHFFFAOYSA-N 2-aminobenzenesulfonic acid Chemical compound NC1=CC=CC=C1S(O)(=O)=O ZMCHBSMFKQYNKA-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
125000003047 N-acetyl group Chemical group 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
150000005840 aryl radicals Chemical class 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
125000003396 thiol group Chemical group [H]S* 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Chemical compound [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 description 2
VQSVOQJUFSROBP-LXGUWJNJSA-N (2r,3r,4r,5s)-6-(2-hydroxyethylamino)hexane-1,2,3,4,5-pentol Chemical compound OCCNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO VQSVOQJUFSROBP-LXGUWJNJSA-N 0.000 description 1
IKXCHOUDIPZROZ-LXGUWJNJSA-N (2r,3r,4r,5s)-6-(ethylamino)hexane-1,2,3,4,5-pentol Chemical compound CCNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO IKXCHOUDIPZROZ-LXGUWJNJSA-N 0.000 description 1
XMWZOWQYICPGNI-JQCXWYLXSA-N (2r,3r,4r,5s)-6-(propan-2-ylamino)hexane-1,2,3,4,5-pentol Chemical compound CC(C)NC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO XMWZOWQYICPGNI-JQCXWYLXSA-N 0.000 description 1
YCANAXVBJKNANM-UHFFFAOYSA-N 1-nitroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2[N+](=O)[O-] YCANAXVBJKNANM-UHFFFAOYSA-N 0.000 description 1
XYOSFLPUWVWHOA-UHFFFAOYSA-N 2-ethylidenepropane-1,3-diol;urea Chemical compound NC(N)=O.CC=C(CO)CO XYOSFLPUWVWHOA-UHFFFAOYSA-N 0.000 description 1
ZEYUSQVGRCPBPG-UHFFFAOYSA-N 4,5-dihydroxy-1,3-bis(hydroxymethyl)imidazolidin-2-one Chemical compound OCN1C(O)C(O)N(CO)C1=O ZEYUSQVGRCPBPG-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
VGGLHLAESQEWCR-UHFFFAOYSA-N N-(hydroxymethyl)urea Chemical compound NC(=O)NCO VGGLHLAESQEWCR-UHFFFAOYSA-N 0.000 description 1
MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
MBHRHUJRKGNOKX-UHFFFAOYSA-N [(4,6-diamino-1,3,5-triazin-2-yl)amino]methanol Chemical compound NC1=NC(N)=NC(NCO)=N1 MBHRHUJRKGNOKX-UHFFFAOYSA-N 0.000 description 1
125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 1
239000002253 acid Substances 0.000 description 1
239000003513 alkali Substances 0.000 description 1
LFVGISIMTYGQHF-UHFFFAOYSA-N ammonium dihydrogen phosphate Chemical compound [NH4+].OP(O)([O-])=O LFVGISIMTYGQHF-UHFFFAOYSA-N 0.000 description 1
229910000387 ammonium dihydrogen phosphate Inorganic materials 0.000 description 1
SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000007900 aqueous suspension Substances 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
150000001720 carbohydrates Chemical class 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
229910052804 chromium Inorganic materials 0.000 description 1
239000011651 chromium Substances 0.000 description 1
229910017052 cobalt Inorganic materials 0.000 description 1
239000010941 cobalt Substances 0.000 description 1
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
150000004985 diamines Chemical class 0.000 description 1
WVJOGYWFVNTSAU-UHFFFAOYSA-N dimethylol ethylene urea Chemical compound OCN1CCN(CO)C1=O WVJOGYWFVNTSAU-UHFFFAOYSA-N 0.000 description 1
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
239000012948 isocyanate Substances 0.000 description 1
150000002513 isocyanates Chemical class 0.000 description 1
229910001629 magnesium chloride Inorganic materials 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
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 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
235000019837 monoammonium phosphate Nutrition 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
235000011056 potassium acetate Nutrition 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
238000006798 ring closing metathesis reaction Methods 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
210000004243 sweat Anatomy 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
ZMZDMBWJUHKJPS-UHFFFAOYSA-M thiocyanate group Chemical group [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 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
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
- 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
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- 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
- C09B69/00—Dyes not provided for by a single group of this subclass

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Coloring (AREA)
Inks, Pencil-Leads, Or Crayons (AREA)

CH747665A 1959-07-02 1960-07-01 Verfahren zur Herstellung von neuen wasserlöslichen Farbstoffen CH405552A (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB22763/59A GB929425A (en)	1959-07-02	1959-07-02	New heterocyclic-nitrogen containing dyestuffs
GB3943259		1959-11-20

Publications (1)

Publication Number	Publication Date
CH405552A true CH405552A (de)	1966-01-15

Family

ID=26256101

Family Applications (3)

Application Number	Title	Priority Date	Filing Date
CH747665A CH405552A (de)	1959-07-02	1960-07-01	Verfahren zur Herstellung von neuen wasserlöslichen Farbstoffen
CH747765A CH418496A (de)	1959-07-02	1960-07-01	Verfahren zur Herstellung von neuen wasserlöslichen Farbstoffen
CH747960A CH405541A (de)	1959-07-02	1960-07-01	Verfahren zur Herstellung von neuen wasserlöslichen Farbstoffen

Family Applications After (2)

Application Number	Title	Priority Date	Filing Date
CH747765A CH418496A (de)	1959-07-02	1960-07-01	Verfahren zur Herstellung von neuen wasserlöslichen Farbstoffen
CH747960A CH405541A (de)	1959-07-02	1960-07-01	Verfahren zur Herstellung von neuen wasserlöslichen Farbstoffen

Country Status (2)

Country	Link
BE (1)	BE592553A (fr)
CH (3)	CH405552A (fr)

1960
- 1960-07-01 CH CH747665A patent/CH405552A/de unknown
- 1960-07-01 BE BE592553A patent/BE592553A/fr unknown
- 1960-07-01 CH CH747765A patent/CH418496A/de unknown
- 1960-07-01 CH CH747960A patent/CH405541A/de unknown

Also Published As

Publication number	Publication date
BE592553A (fr)	1960-10-02
CH418496A (de)	1966-08-15
CH405541A (de)	1966-01-15

Publication	Publication Date	Title
DE751343C (de)	1953-05-04	Verfahren zur Herstellung von Disazofarbstoffen
DE2748929C2 (de)	1987-05-07	Wasserlösliche Farbstoffe, Verfahren zu ihrer Herstellung, deren Verwendung als faserreaktive Farbstoffe zum Färben und Bedrucken von Fasermaterialien
DE859343C (de)	1952-12-15	Verfahren zur Herstellung von Azofarbstoffen
EP0014844B1 (fr)	1982-05-05	Dérivés de fluortriazine, procédé de préparation de dérivés de fluortriazine et de colorants réactifs et leur application
DE3043915C2 (fr)	1989-07-20
EP0212345B1 (fr)	1991-09-04	Préparation tinctoriale aqueuse, sa fabrication et son utilisation
CH675126A5 (fr)	1990-08-31
CH619977A5 (fr)	1980-10-31
CH405552A (de)	1966-01-15	Verfahren zur Herstellung von neuen wasserlöslichen Farbstoffen
DE1164370B (de)	1964-03-05	Verfahren zum Faerben und Bedrucken von Textilien mit Schwefelfarbstoffen
EP0098799B1 (fr)	1986-09-10	Complexes de métaux 1:2 de colorants azométhiniques contenant des groupes arylazoiques
DE1007451B (de)	1957-05-02	Verfahren zur Herstellung von Monoazofarbstoffen
EP0005449B1 (fr)	1982-01-06	Colorants monoazoiques solubles dans l'eau, leur préparation, solutions aqueuses concentrées contenant les colorants monoazoiques, la préparation des solutions, l'utilisation des colorants et des solutions concentrées et les matériaux teints et imprimés avec ceux-ci
EP0018939B1 (fr)	1983-10-05	Colorants du type 1:2 complexes métalliques des azométhines, procédé pour leur préparation et procédé pour la teinture et l'impression au moyen de ces colorants
DE882738C (de)	1953-07-13	Verfahren zur Herstellung von Trisazofarbstoffen
DE833959C (de)	1952-03-13	Verfahren zur Herstellung von chemotherapeutisch wertvollen Biguanidderivaten
DE1444719A1 (de)	1969-10-23	Verfahren zur Herstellung von metallhaltigen Formazanfarbstoffen
AT164015B (de)	1949-09-26	Verfahren zur Herstellung metallhaltiger Azofarbstoffe
DE881711C (de)	1953-07-02	Verfahren zur Herstellung von kupferhaltigen Disazofarbstoffen der Stilbenreihe
AT167616B (de)	1951-02-10	Verfahren zur Herstellung von neuen Azofarbstoffen
DE957150C (de)	1957-01-31	Verfahren zur Herstellung von Disazofarbstoffen
CH515315A (de)	1971-11-15	Verfahren zur Herstellung von faserreaktiven, schwermetallhaltigen Formazanfarbstoffen
DE1007904B (de)	1957-05-09	Verfahren zur Herstellung von Triazinreste enthaltenden Azofarbstoffen
DE548679C (de)	1932-04-16	Verfahren zur Herstellung von metallhaltigen Azofarbstoffen
DE853188C (de)	1952-10-23	Verfahren zur Herstellung von Mono-, Dis- oder Polyazofarbstoffen