CH520185A - Verfahren zur Herstellung von Monoazofarbstoffen - Google Patents

Verfahren zur Herstellung von Monoazofarbstoffen

Info

Publication number: CH520185A
Authority: CH; Switzerland
Prior art keywords: dyes; alkoxy; dichloro; formula; triazines
Prior art date: 1968-05-17

Application number

CH556369A

Other languages

German (de)

English (en)

Inventor

Henri Dr Riat

Oesterlein Fritz

Original Assignee

Ciba Geigy 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.)

1968-05-17

Filing date

1969-04-10

Publication date

1972-03-15

1968-05-17 Priority claimed from CH729668A external-priority patent/CH502424A/de

1969-04-10 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1969-04-10 Priority to CH556369A priority Critical patent/CH520185A/de

1969-05-16 Priority to ES367302A priority patent/ES367302A1/es

1972-03-15 Publication of CH520185A publication Critical patent/CH520185A/de

Links

239000002253 acid Substances 0.000 title claims abstract description 36
239000000975 dye Substances 0.000 title claims abstract description 35
-1 aminomonoazo Chemical group 0.000 title claims abstract description 24
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 title claims abstract description 6
125000001624 naphthyl group Chemical group 0.000 title description 2
125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
125000000217 alkyl group Chemical group 0.000 claims abstract description 5
238000009833 condensation Methods 0.000 claims abstract description 3
230000005494 condensation Effects 0.000 claims abstract description 3
238000000034 method Methods 0.000 claims description 17
230000008569 process Effects 0.000 claims description 9
238000002360 preparation method Methods 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
230000001419 dependent effect Effects 0.000 claims 3
OMRXVBREYFZQHU-UHFFFAOYSA-N 2,4-dichloro-1,3,5-triazine Chemical class ClC1=NC=NC(Cl)=N1 OMRXVBREYFZQHU-UHFFFAOYSA-N 0.000 claims 2
125000004430 oxygen atom Chemical group O* 0.000 claims 2
IHDBZCJYSHDCKF-UHFFFAOYSA-N 4,6-dichlorotriazine Chemical compound ClC1=CC(Cl)=NN=N1 IHDBZCJYSHDCKF-UHFFFAOYSA-N 0.000 claims 1
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
239000000987 azo dye Substances 0.000 claims 1
125000004432 carbon atom Chemical group C* 0.000 claims 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
229910052760 oxygen Inorganic materials 0.000 claims 1
239000001301 oxygen Substances 0.000 claims 1
239000007858 starting material Substances 0.000 claims 1
229910052717 sulfur Inorganic materials 0.000 claims 1
125000004434 sulfur atom Chemical group 0.000 claims 1
238000004043 dyeing Methods 0.000 abstract description 7
229920000742 Cotton Polymers 0.000 abstract description 5
239000001913 cellulose Substances 0.000 abstract description 2
229920002678 cellulose Polymers 0.000 abstract description 2
239000010985 leather Substances 0.000 abstract description 2
239000004627 regenerated cellulose Substances 0.000 abstract description 2
210000002268 wool Anatomy 0.000 abstract description 2
125000004183 alkoxy alkyl group Chemical group 0.000 abstract 1
125000002947 alkylene group Chemical group 0.000 abstract 1
238000010025 steaming Methods 0.000 abstract 1
239000004753 textile Substances 0.000 abstract 1
JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 8
FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical group C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 7
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 5
FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 5
239000004744 fabric Substances 0.000 description 4
ZNXSFVXZQBETRJ-UHFFFAOYSA-N (3-aminophenyl)urea Chemical class NC(=O)NC1=CC=CC(N)=C1 ZNXSFVXZQBETRJ-UHFFFAOYSA-N 0.000 description 3
CKZQTJDTHHVYSK-UHFFFAOYSA-N C1(=CC=CC=C1)C.N1=NN=CC=C1 Chemical compound C1(=CC=CC=C1)C.N1=NN=CC=C1 CKZQTJDTHHVYSK-UHFFFAOYSA-N 0.000 description 3
239000000463 material Substances 0.000 description 3
239000000203 mixture Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
FPZWZCWUIYYYBU-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl acetate Chemical group CCOCCOCCOC(C)=O FPZWZCWUIYYYBU-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
239000007859 condensation product Substances 0.000 description 2
230000008878 coupling Effects 0.000 description 2
238000010168 coupling process Methods 0.000 description 2
238000005859 coupling reaction Methods 0.000 description 2
239000000835 fiber Substances 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
238000002955 isolation Methods 0.000 description 2
239000011707 mineral Substances 0.000 description 2
235000010755 mineral Nutrition 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
239000001488 sodium phosphate Substances 0.000 description 2
LJRGBERXYNQPJI-UHFFFAOYSA-M sodium;3-nitrobenzenesulfonate Chemical compound [Na+].[O-][N+](=O)C1=CC=CC(S([O-])(=O)=O)=C1 LJRGBERXYNQPJI-UHFFFAOYSA-M 0.000 description 2
239000002562 thickening agent Substances 0.000 description 2
WDQPNXLZKXUEEC-UHFFFAOYSA-N (3-amino-4-methoxyphenyl)urea Chemical compound COC1=CC=C(NC(N)=O)C=C1N WDQPNXLZKXUEEC-UHFFFAOYSA-N 0.000 description 1
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
125000005923 1,2-dimethylpropyloxy group Chemical group 0.000 description 1
IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
VMCICDADKZXNHW-UHFFFAOYSA-N 1h-triazin-2-amine Chemical compound NN1NC=CC=N1 VMCICDADKZXNHW-UHFFFAOYSA-N 0.000 description 1
JKAPWXKZLYJQJJ-UHFFFAOYSA-N 2,4-dichloro-6-methoxy-1,3,5-triazine Chemical compound COC1=NC(Cl)=NC(Cl)=N1 JKAPWXKZLYJQJJ-UHFFFAOYSA-N 0.000 description 1
RDRRVDWNUVOYMG-UHFFFAOYSA-N 2-amino-1h-naphthalene-1,2,3-trisulfonic acid Chemical class C1=CC=C2C=C(S(O)(=O)=O)C(N)(S(O)(=O)=O)C(S(O)(=O)=O)C2=C1 RDRRVDWNUVOYMG-UHFFFAOYSA-N 0.000 description 1
RROGZKOUUYGSDS-UHFFFAOYSA-N 4-aminonaphthalene-1,2,3-trisulfonic acid Chemical class C1=CC=C2C(N)=C(S(O)(=O)=O)C(S(O)(=O)=O)=C(S(O)(=O)=O)C2=C1 RROGZKOUUYGSDS-UHFFFAOYSA-N 0.000 description 1
GFPQSWFFPRQEHH-UHFFFAOYSA-N 7-aminonaphthalene-1,3,6-trisulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C=C(S(O)(=O)=O)C(N)=CC2=C1S(O)(=O)=O GFPQSWFFPRQEHH-UHFFFAOYSA-N 0.000 description 1
229920003043 Cellulose fiber Polymers 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
230000009471 action Effects 0.000 description 1
150000001448 anilines Chemical class 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000006172 buffering agent Substances 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000004040 coloring Methods 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
239000003599 detergent Substances 0.000 description 1
150000008049 diazo compounds Chemical class 0.000 description 1
238000006193 diazotization reaction Methods 0.000 description 1
125000000950 dibromo group Chemical group Br* 0.000 description 1
238000009967 direct dyeing Methods 0.000 description 1
BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
229910000397 disodium phosphate Inorganic materials 0.000 description 1
235000019800 disodium phosphate Nutrition 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
239000002609 medium Substances 0.000 description 1
229910000403 monosodium phosphate Inorganic materials 0.000 description 1
235000019799 monosodium phosphate Nutrition 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
238000005185 salting out Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
150000003333 secondary alcohols Chemical class 0.000 description 1
239000000661 sodium alginate Substances 0.000 description 1
235000010413 sodium alginate Nutrition 0.000 description 1
229940005550 sodium alginate Drugs 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
238000001694 spray drying Methods 0.000 description 1
238000010186 staining Methods 0.000 description 1
238000003756 stirring Methods 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
- C09B62/04—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 to a triazine ring
- C09B62/08—Azo dyes
- C09B62/085—Monoazo dyes

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Coloring (AREA)

CH556369A 1968-05-17 1969-04-10 Verfahren zur Herstellung von Monoazofarbstoffen CH520185A (de)

Priority Applications (2)

Application Number	Priority Date	Filing Date	Title
CH556369A CH520185A (de)	1968-05-17	1969-04-10	Verfahren zur Herstellung von Monoazofarbstoffen
ES367302A ES367302A1 (es)	1968-05-17	1969-05-16	Procedimiento para la preparacion de nuevos colorantes azoicos.

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CH729668A CH502424A (de)	1968-05-17	1968-05-17	Verfahren zur Herstellung von Monoazofarbstoffen
CH556369A CH520185A (de)	1968-05-17	1969-04-10	Verfahren zur Herstellung von Monoazofarbstoffen

Publications (1)

Publication Number	Publication Date
CH520185A true CH520185A (de)	1972-03-15

Family

ID=25697989

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH556369A CH520185A (de)	1968-05-17	1969-04-10	Verfahren zur Herstellung von Monoazofarbstoffen

Country Status (2)

Country	Link
CH (1)	CH520185A (es)
ES (1)	ES367302A1 (es)

1969
- 1969-04-10 CH CH556369A patent/CH520185A/de not_active IP Right Cessation
- 1969-05-16 ES ES367302A patent/ES367302A1/es not_active Expired

Also Published As

Publication number	Publication date
ES367302A1 (es)	1971-06-16

Legal Events

Date	Code	Title	Description
1987-01-30	PL	Patent ceased

Publication	Publication Date	Title
DE2557141C2 (de)	1983-05-11	Reaktivfarbstoffe, deren Herstellung und Verwendung
CH628671A5 (de)	1982-03-15	Verfahren zur herstellung von reaktivfarbstoffen.
DE2050948A1 (de)	1971-11-18	Reaktive Farbstoffe und Verfahren zu deren Herstellung
DE2500062A1 (de)	1975-07-10	Faserreaktive tetrazofarbstoffe
DE3202120A1 (de)	1983-07-28	"wasserloesliche kupferkomplex-disazoverbindungen, verfahren zu deren herstellung und ihre verwendng als farbstoffe"
DE2162612C2 (de)	1985-04-18	Azoverbindungen, deren Herstellung und Verwendung
DE2318412C2 (de)	1984-05-17	Azo-Reaktivfarbstoffe
DE1544442C3 (de)	1978-06-29	Faserreaktive Azofarbstoffe und deren Verwendung zum Färben und Bedrucken
DE1419794C3 (de)	1975-02-20	Verfahren zur Herstellung von Dlsazoreaktivfarbstoffen und deren Verwendung
CH520185A (de)	1972-03-15	Verfahren zur Herstellung von Monoazofarbstoffen
DE1924684A1 (de)	1969-11-27	Neue Monazoverbindungen und deren Verwendung
DE1298220B (de)	1969-06-26	Verfahren zur Herstellung faserreaktiver Monoazofarbstoffe
DE3118074A1 (de)	1982-11-25	Monoazoverbindungen, verfahren zu ihrer herstellung und ihre verwendung als farbstoffe
CH599316A5 (en)	1978-05-31	Fibre-reactive azo dyes prepn.
CH524671A (de)	1972-06-30	Verfahren zur Herstellung von neuen Monoazofarbstoffen
DE1192346B (de)	1965-05-06	Verfahren zur Herstellung von Azophthalocyaninfarbstoffen
DE1231365B (de)	1966-12-29	Verfahren zur Herstellung faserreaktiver Azofarbstoffe
AT214545B (de)	1961-04-10	Verfahren zur Herstellung von mindestens einen dihalogenierten Pyrimidinring enthaltenden wasserlöslichen Farbstoffen der Azo-, Anthrachinon- und Phthalocyaninreihe
DE2108402A1 (de)	1971-09-09	Neue Azoverbindungen, Verfahren zu deren Herstellung und Verwendung
DE1283984B (de)	1968-11-28	Verfahren zur Herstellung von faserreaktiven Schwermetallkomplexen von Monoazofarbstoffen
DE1924683A1 (de)	1969-11-27	Faserreaktive Farbstoffe,deren Herstellung und Verwendung
DE1112229B (de)	1961-08-03	Verfahren zur Herstellung von reaktiven Azofarbstoffen
CH377019A (de)	1964-04-30	Verfahren zur Herstellung neuer Azofarbstoffe
DE1954269A1 (de)	1970-06-04	Disazoverbindungen,deren Herstellung und Verwendung
DE1225790B (de)	1966-09-29	Verfahren zur Herstellung metallhaltiger Monoazofarbstoffe