GB1099097A - Disazo dispersion dyestuffs containing a urethane group - Google Patents
Disazo dispersion dyestuffs containing a urethane groupInfo
- Publication number
- GB1099097A GB1099097A GB5450265A GB5450265A GB1099097A GB 1099097 A GB1099097 A GB 1099097A GB 5450265 A GB5450265 A GB 5450265A GB 5450265 A GB5450265 A GB 5450265A GB 1099097 A GB1099097 A GB 1099097A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- coupling
- compound
- diazotizing
- dyes
- 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
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
- C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
- C09B31/02—Disazo dyes
-
- 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
- C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
- C09B31/02—Disazo dyes
- C09B31/06—Disazo dyes from a coupling component "C" containing a directive hydroxyl group
-
- 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
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/12—Preparation of azo dyes from other azo compounds by acylation of amino groups
- C09B43/124—Preparation of azo dyes from other azo compounds by acylation of amino groups with monocarboxylic acids, carbamic esters or halides, mono- isocyanates, or haloformic acid esters
- C09B43/1245—Preparation of azo dyes from other azo compounds by acylation of amino groups with monocarboxylic acids, carbamic esters or halides, mono- isocyanates, or haloformic acid esters with formation of NHCOOR, NHCOSR or NHCSOR groups by acylation
-
- 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
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/28—Preparation of azo dyes from other azo compounds by etherification of hydroxyl groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Abstract
The invention comprises disperse dyestuffs (free from SO3H and COOH groups) of the formula <FORM:1099097/C4-C5/1> wherein R represents an alkyl, cycloalkyl, aralkyl or aryl radical, R1 represents an alkyl, aralkyl or aryl radical, R1 and R2 represent aryl radicals, R3 represents an aromatic-carbocyclic or -heterocyclic or aliphatic radical in which the OR4 group is in the adjacent or p-position to the azo grouping, and R4 represents H or alkyl. The dyes may contain non-ionic substituents. They may be obtained by either diazotizing an aminoazo compound of the formula: ROOC-NR1-R1-N = N-R2-NH2 and coupling with an enolic or phenolic coupling component in an adjacent or p-position to the OH group, or treating a dye of the formula: R1HN-R1-N = N-R2-N = N-R3-OR4 with a haloformic ester of the formula: hal-COOR wherein 'hal' represents a halogen atom. The resulting dyes may be alkylated. Suitable enolic and phenolic coupling components are those of the phenol, naphthol, 5-pyrazolone, acylacetic acid amide and hydroxyquinoline series. Examples are given for the production of the dyes. They may be used for dyeing or printing hydrophobic materials. Aminoazo compounds of the formula: ROOC-NR1-R1-N = N-R2-NH2 are obtained by diazotizing an aminoarylurethane of the formula: ROOC-NR1-R1-NH2 and coupling with an arylamine of the formula R2-NH2. Diazo dyes of the formula R1HN-R1-N = N-R2-N = N-R3-OR4 are obtained either by diazotizing a compound Acyl-NR1-R1-NH2, coupling this compound with a coupling component R2-NH2, diazotizing the product, coupling this compound with an enolic or phenolic coupling component R3-OH and hydrolysing the acylamino group either during the course of the process or afterwards, or by coupling a diazo compound of an amine of the formula HO-R3-NH2 with an aminoaryl compound R2-NH2, diazotizing and coupling the product with an amine R1-NHR1.ALSO:1 - Amino - 4 - N - carbomethoxy - N - methylaminobenzene is obtained by reacting 1-N-methylamino -4-nitrobenzene with chloroformic acid methyl ester at 50 DEG C. in dimethylaniline and dioxan, giving 1 - nitro - 4 - N - carbomethoxy - N - methylaminobenzene, and reducing this intermediate with H2 and Raney Ni in methanol giving the required product. The compound is useful as an intermediate in the preparation of dyestuffs (see Division C4).
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEF44812A DE1289591B (en) | 1964-12-24 | 1964-12-24 | Process for the preparation of disperse dyes |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1099097A true GB1099097A (en) | 1968-01-17 |
Family
ID=7100200
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB5450265A Expired GB1099097A (en) | 1964-12-24 | 1965-12-23 | Disazo dispersion dyestuffs containing a urethane group |
Country Status (5)
Country | Link |
---|---|
BE (1) | BE674021A (en) |
DE (1) | DE1289591B (en) |
FR (1) | FR1461862A (en) |
GB (1) | GB1099097A (en) |
NL (1) | NL6516849A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4344880A (en) * | 1979-12-01 | 1982-08-17 | Basf Aktiengesellschaft | Disazo dyestuffs having an acylamino group and an aromatic-oxy group on different terminal moieties |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3019064A1 (en) * | 1980-05-19 | 1981-11-26 | Cassella Ag, 6000 Frankfurt | METHOD FOR COLORING AND PRINTING HYDROPHOBIC FIBER MATERIALS AND AZO DYES SUITABLE FOR THIS |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE963093C (en) * | 1952-10-31 | 1957-05-02 | Sandoz Ag | Process for the preparation of water-insoluble disazo dyes |
DE1099668B (en) * | 1958-02-12 | 1961-02-16 | Ciba Geigy | Process for the preparation of water-insoluble diazo dyes |
DE1153476B (en) * | 1960-02-15 | 1963-08-29 | Sandoz Ag | Process for the preparation of disazo dyes |
-
1964
- 1964-12-24 DE DEF44812A patent/DE1289591B/en active Pending
-
1965
- 1965-12-20 BE BE674021D patent/BE674021A/xx unknown
- 1965-12-23 GB GB5450265A patent/GB1099097A/en not_active Expired
- 1965-12-23 NL NL6516849A patent/NL6516849A/xx unknown
- 1965-12-24 FR FR43672A patent/FR1461862A/en not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4344880A (en) * | 1979-12-01 | 1982-08-17 | Basf Aktiengesellschaft | Disazo dyestuffs having an acylamino group and an aromatic-oxy group on different terminal moieties |
Also Published As
Publication number | Publication date |
---|---|
DE1289591B (en) | 1969-02-20 |
NL6516849A (en) | 1966-06-27 |
FR1461862A (en) | 1966-12-09 |
BE674021A (en) | 1966-04-15 |
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