GB576306A - Manufacture of monoazo dyestuffs, capable of being chromed - Google Patents
Manufacture of monoazo dyestuffs, capable of being chromedInfo
- Publication number
- GB576306A GB576306A GB7004/43A GB700443A GB576306A GB 576306 A GB576306 A GB 576306A GB 7004/43 A GB7004/43 A GB 7004/43A GB 700443 A GB700443 A GB 700443A GB 576306 A GB576306 A GB 576306A
- Authority
- GB
- United Kingdom
- Prior art keywords
- tert
- phenol
- amyl
- butyl
- methyl
- 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 abstract 3
- 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 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 4
- 230000008878 coupling Effects 0.000 abstract 4
- 238000010168 coupling process Methods 0.000 abstract 4
- 238000005859 coupling reaction Methods 0.000 abstract 4
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- WGLLSSPDPJPLOR-UHFFFAOYSA-N 2,3-dimethylbut-2-ene Chemical group CC(C)=C(C)C WGLLSSPDPJPLOR-UHFFFAOYSA-N 0.000 abstract 2
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 abstract 2
- OSDLLIBGSJNGJE-UHFFFAOYSA-N 4-chloro-3,5-dimethylphenol Chemical compound CC1=CC(O)=CC(C)=C1Cl OSDLLIBGSJNGJE-UHFFFAOYSA-N 0.000 abstract 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 abstract 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- 238000010438 heat treatment Methods 0.000 abstract 2
- UUBASQRIVIRMIQ-UHFFFAOYSA-N 4-chloro-2-hexylphenol Chemical compound CCCCCCC1=CC(Cl)=CC=C1O UUBASQRIVIRMIQ-UHFFFAOYSA-N 0.000 abstract 1
- OAHMVZYHIJQTQC-UHFFFAOYSA-N 4-cyclohexylphenol Chemical compound C1=CC(O)=CC=C1C1CCCCC1 OAHMVZYHIJQTQC-UHFFFAOYSA-N 0.000 abstract 1
- GYMNBLJZTNBLNB-UHFFFAOYSA-N 4-methyl-2-octylphenol Chemical compound CCCCCCCCC1=CC(C)=CC=C1O GYMNBLJZTNBLNB-UHFFFAOYSA-N 0.000 abstract 1
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 239000000975 dye Substances 0.000 abstract 1
- 239000000835 fiber Substances 0.000 abstract 1
- 238000007689 inspection Methods 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- GJYCVCVHRSWLNY-UHFFFAOYSA-N ortho-butylphenol Natural products CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- 239000001117 sulphuric acid Substances 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
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
- C09B45/14—Monoazo compounds
- C09B45/16—Monoazo compounds containing chromium
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Monoazo dyes, chromable in substance, in the dyebath or on the fibre, are obtained by coupling diazotised 4-nitro-2-aminophenol-6-sulphonic acid with a phenol of the general formula <FORM:0576306/IV/1> wherein X represents tertiary alkyl with at most 8 carbon atoms or cycloalkyl and Y represents alkyl with at most 8 carbon atoms or cycloalkyl and Z represents H or methyl. Specified coupling components are 2 : 4-di-(tert.-amyl)-phenol (cf. Specification 452,335), 2-tert.-butyl-4-tert.-amyl-phenol, 2 : 4-di-(tert.-butyl)-phenyl, 2-tert.-amyl-4-methyl-phenol, 2-tert.-octyl-4-methyl-phenol, 2-tert.-amyl-4 : 5-dimethyl - phenol, 2 - tert. - hexyl - 4 - tert. - butyl-phenol and 2-tert.-butyl-4-cyclohexylphenol. Examples relate to the production of the dyestuffs having as coupling components: (1) 2 : 4-di-(tert.-amyl)-phenol; (2) 2-tert.-amyl-4-methyl-phenol or 2-tert.-hexyl-4-tert.-butyl-phenol. Specifications 325,208, [Class 2 (iii)], and 450,127 also are referred to. The Specification as open to inspection under Sect. 91 comprises also the manufacture of the corresponding dyestuffs in which (a) X in the general formula represents any alkyl residue containing from 3 to 8 carbon atoms, Y in the general formula represents chlorine, and specifies, as additional coupling components, 2-hexyl-4-chloro-phenol, 2-tert.-butyl-4-chloro-phenol, 2-propyl-4-tert.-butyl-phenol. This subject-matter does not appear in the Specification as accepted. p 2-Tert.-butyl-4-tert.-amyl phenol is obtained by reaction of p-tert.-amyl phenol with trimethyl-carbinol in 72 per cent sulphuric acid at 60 DEG C. 2-Tert.-amyl-4-methyl-phenol is obtained by similar reaction of p-cresol with tert.-amyl alcohol. 2-Tert.-amyl-4 : 5-dimethyl-phenol is obtained by similar reaction of 3 : 4-dimethyl-phenol with tert.-amyl alcohol. 2-Tert.-butyl-4-cyclohexyl-phenol is obtained by similar reaction of 4-cyclohexyl-phenol with trimethylcarbinol. 2-Octyl-4-methyl-phenol is obtained by heating p-cresol with di-isobutylene at 80 DEG C. in presence of aluminium chloride. 2-Hexyl-4-tert.-butyl-phenol is obtained by similar heating of tetramethylethylene with p-tert.-butyl-phenol.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH576306X | 1958-03-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB576306A true GB576306A (en) | 1946-03-28 |
Family
ID=4521226
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB7004/43A Expired GB576306A (en) | 1942-05-05 | 1943-05-04 | Manufacture of monoazo dyestuffs, capable of being chromed |
Country Status (2)
| Country | Link |
|---|---|
| BE (1) | BE576306A (en) |
| GB (1) | GB576306A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES260505A1 (en) * | 1959-09-04 | 1961-04-01 | Parque Davis & Company | Benzamide compounds and methods for their production |
-
1943
- 1943-05-04 GB GB7004/43A patent/GB576306A/en not_active Expired
-
1959
- 1959-03-03 BE BE576306A patent/BE576306A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BE576306A (en) | 1959-09-03 |
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