GB630181A - Manufacture of azo dyestuffs - Google Patents
Manufacture of azo dyestuffsInfo
- Publication number
- GB630181A GB630181A GB28979/47A GB2897947A GB630181A GB 630181 A GB630181 A GB 630181A GB 28979/47 A GB28979/47 A GB 28979/47A GB 2897947 A GB2897947 A GB 2897947A GB 630181 A GB630181 A GB 630181A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- disulphonic
- sulphonic acid
- phenylenediamine
- aminobenzoyl
- 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
- 238000004519 manufacturing process Methods 0.000 title 1
- 239000002253 acid Substances 0.000 abstract 7
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 abstract 2
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 abstract 2
- -1 aminoazo Chemical group 0.000 abstract 2
- 238000010168 coupling process Methods 0.000 abstract 2
- 238000005859 coupling reaction Methods 0.000 abstract 2
- 150000004985 diamines Chemical class 0.000 abstract 2
- 239000000975 dye Substances 0.000 abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 2
- IHZCKOBTZMHTDA-UHFFFAOYSA-N 2-(2-amino-4-methylphenoxy)acetic acid Chemical compound CC1=CC=C(OCC(O)=O)C(N)=C1 IHZCKOBTZMHTDA-UHFFFAOYSA-N 0.000 abstract 1
- JRBJSXQPQWSCCF-UHFFFAOYSA-N 3,3'-Dimethoxybenzidine Chemical compound C1=C(N)C(OC)=CC(C=2C=C(OC)C(N)=CC=2)=C1 JRBJSXQPQWSCCF-UHFFFAOYSA-N 0.000 abstract 1
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 abstract 1
- 229920003043 Cellulose fiber Polymers 0.000 abstract 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 abstract 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 abstract 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 150000001491 aromatic compounds Chemical class 0.000 abstract 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 abstract 1
- 230000008878 coupling Effects 0.000 abstract 1
- NCBZRJODKRCREW-UHFFFAOYSA-N m-anisidine Chemical compound COC1=CC=CC(N)=C1 NCBZRJODKRCREW-UHFFFAOYSA-N 0.000 abstract 1
- WXWCDTXEKCVRRO-UHFFFAOYSA-N para-Cresidine Chemical compound COC1=CC=C(C)C=C1N WXWCDTXEKCVRRO-UHFFFAOYSA-N 0.000 abstract 1
- 150000003142 primary aromatic amines Chemical class 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 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
- 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
- C09B43/136—Preparation of azo dyes from other azo compounds by acylation of amino groups with polyfunctional acylating agents
- C09B43/14—Preparation of azo dyes from other azo compounds by acylation of amino groups with polyfunctional acylating agents with phosgene or thiophosgene
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Azo dyestuffs are manufactured by treating two molecular proportions of an aminoazo dyestuff of the general formula R1-N=N-R2-NH2, wherein R1 represents the radical of an O-acyl (e.g. acetyl or especially p-toluenesulphonyl) 1 : 8-aminonaphthol-3 : 6- or 4 : 6-disulphonic acid, and R2 represents the radical of a primary aromatic amine coupling in p-position to the amino group, together with one molecular proportion of a mono- or polynuclear aromatic compound containing two primary amino groups, not in o-position to one another, and, if desired, further substituents, particularly water-solubilizing groups, with phosgene until the primary amino groups are completely converted, and subsequently splitting off the acyl radical from the O-acyl group. The products dye cellulose fibres in red tints. Examples and a table illustrate the use of the following components: p-coupling amines: 1 - amino - 3 - methyl - 6 - methoxybenzene, m - anisidine, m - toluidine, 2 - amino - 4-methylphenoxyacetic acid; diamines: 4 : 41-diaminostilbene - 2 : 21 - disulphonic acid and its mono- (m- and p-aminobenzoyl)- and di-(p-aminobenzoyl)-derivatives, benzidine and its 3-sulphonic acid, 2 : 21- and 3 : 31-disulphonic acids and 3 : 31-dicarboxylic acid, m- and p-phenylenediamine, p - phenylenediamine - carboxylic and sulphonic acid, 1 : 3-phenylenediamine - 4 - sulphonic acid, 4 : 41 - diaminodiphenylurea - 3 : 31 - disulphonic acid, 4-(41 - aminobenzoylamino) - 1 - aminobenzene-2 - sulphonic acid, 1 - methyl - 2 : 6 - diaminobenzene - 4 - sulphonic acid, 4 : 41 - diaminodiphenyl sulphide and its 2 : 21-disulphonic acid, 4 : 41 - diaminodiphenylamine - 2 - sulphonic acid, 41 - aminobenzoyl - p - phenylenediamine, o - dianisidine, o - tolidine and 4 : 41-diaminodiphenylmethane. Additional diamines specified are 4 : 41-diaminodiphenylurea-2 : 21-disulphonic acid, 4-(31-aminocinnamoylamino)-1-aminobenzene-2-sulphonic acid and 1 : 5-diaminonaphthalene-3 : 7-disulphonic acid.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH630181X | 1946-10-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB630181A true GB630181A (en) | 1949-10-06 |
Family
ID=4524693
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB28979/47A Expired GB630181A (en) | 1946-10-31 | 1947-10-30 | Manufacture of azo dyestuffs |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB630181A (en) |
-
1947
- 1947-10-30 GB GB28979/47A patent/GB630181A/en not_active Expired
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