GB694451A - Improvements relating to polyazine dyestuffs - Google Patents
Improvements relating to polyazine dyestuffsInfo
- Publication number
- GB694451A GB694451A GB2829050A GB2829050A GB694451A GB 694451 A GB694451 A GB 694451A GB 2829050 A GB2829050 A GB 2829050A GB 2829050 A GB2829050 A GB 2829050A GB 694451 A GB694451 A GB 694451A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydrazine
- reacted
- terephthalaldehyde
- dialdehyde
- tetra
- 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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 20
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract 10
- ZGCHATBSUIJLRL-UHFFFAOYSA-N hydrazine sulfate Chemical compound NN.OS(O)(=O)=O ZGCHATBSUIJLRL-UHFFFAOYSA-N 0.000 abstract 10
- ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical compound N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 abstract 7
- -1 aliphatic alcohols Chemical class 0.000 abstract 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 6
- 239000001117 sulphuric acid Substances 0.000 abstract 6
- 235000011149 sulphuric acid Nutrition 0.000 abstract 6
- 239000004744 fabric Substances 0.000 abstract 5
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 abstract 4
- JRDQENHFPUQHTP-UHFFFAOYSA-N C(C)(=O)O.C(C)(=O)O.C(C)(=O)O.C(C)(=O)O.C(C1=CC=C(C=O)C=C1)=O Chemical compound C(C)(=O)O.C(C)(=O)O.C(C)(=O)O.C(C)(=O)O.C(C1=CC=C(C=O)C=C1)=O JRDQENHFPUQHTP-UHFFFAOYSA-N 0.000 abstract 4
- 229920000742 Cotton Polymers 0.000 abstract 4
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 abstract 4
- 150000003839 salts Chemical class 0.000 abstract 4
- 239000000243 solution Substances 0.000 abstract 4
- YSIIHTHHMPYKFP-UHFFFAOYSA-N 2,5-dimethoxyterephthalaldehyde Chemical compound COC1=CC(C=O)=C(OC)C=C1C=O YSIIHTHHMPYKFP-UHFFFAOYSA-N 0.000 abstract 3
- 239000007864 aqueous solution Substances 0.000 abstract 3
- 238000004043 dyeing Methods 0.000 abstract 3
- RYIGSDDWQGKRMF-UHFFFAOYSA-N 4-methoxybenzene-1,3-dicarbaldehyde Chemical compound COC1=CC=C(C=O)C=C1C=O RYIGSDDWQGKRMF-UHFFFAOYSA-N 0.000 abstract 2
- YMWWOYIEZQIQRX-UHFFFAOYSA-N C(C)(=O)O.C(C)(=O)O.C(C)(=O)O.C(C)(=O)O.ClC1=C(C=O)C=C(C(=C1)C=O)Cl Chemical compound C(C)(=O)O.C(C)(=O)O.C(C)(=O)O.C(C)(=O)O.ClC1=C(C=O)C=C(C(=C1)C=O)Cl YMWWOYIEZQIQRX-UHFFFAOYSA-N 0.000 abstract 2
- MJOQJPYNENPSSS-XQHKEYJVSA-N [(3r,4s,5r,6s)-4,5,6-triacetyloxyoxan-3-yl] acetate Chemical compound CC(=O)O[C@@H]1CO[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O MJOQJPYNENPSSS-XQHKEYJVSA-N 0.000 abstract 2
- 239000012736 aqueous medium Substances 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 229940117975 chromium trioxide Drugs 0.000 abstract 2
- WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 abstract 2
- GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 abstract 2
- 239000000463 material Substances 0.000 abstract 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 abstract 2
- 239000003960 organic solvent Substances 0.000 abstract 2
- 230000001590 oxidative effect Effects 0.000 abstract 2
- 239000000049 pigment Substances 0.000 abstract 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 abstract 1
- VSUKSWCSOBXUFG-UHFFFAOYSA-N 2,5-dibromoterephthalaldehyde Chemical compound BrC1=CC(C=O)=C(Br)C=C1C=O VSUKSWCSOBXUFG-UHFFFAOYSA-N 0.000 abstract 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 abstract 1
- 241000416162 Astragalus gummifer Species 0.000 abstract 1
- 244000248349 Citrus limon Species 0.000 abstract 1
- 235000005979 Citrus limon Nutrition 0.000 abstract 1
- 229920001615 Tragacanth Polymers 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 238000001035 drying Methods 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 235000019253 formic acid Nutrition 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 238000010025 steaming Methods 0.000 abstract 1
- KUCOHFSKRZZVRO-UHFFFAOYSA-N terephthalaldehyde Chemical compound O=CC1=CC=C(C=O)C=C1 KUCOHFSKRZZVRO-UHFFFAOYSA-N 0.000 abstract 1
- 239000004753 textile Substances 0.000 abstract 1
- 230000008719 thickening Effects 0.000 abstract 1
- 229940116362 tragacanth Drugs 0.000 abstract 1
- 235000010487 tragacanth Nutrition 0.000 abstract 1
- 239000000196 tragacanth Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/72—Hydrazones
-
- 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
- C09B26/00—Hydrazone dyes; Triazene dyes
- C09B26/02—Hydrazone dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Abstract
Insoluble coloured polyazines are made by reacting hydrazine, its hydrate or a salt thereof with an aromatic p- or m dialdehyde or a tetra-acetate thereof in substantially an aqueous medium the hydrazine, its hydrate or its salt being used in the proportion of at least 1 mol. to 1 mol. of the dialdehyde; 80-90 DEG C. are preferred temperatures. Water-miscible organic solvents, e.g. lower aliphatic alcohols, may be present. The dialdehyde may be substituted and specified dialdehydes are terephthal-, isophthal-, 4-methoxy-, isophthal-, 2,5-dichloroterephthal-, 5-hydroxy-isophthal-, 2,5-dibromoterephthal and 2,5-dimethoxy-terephthal-aldehyde. The pigments are yellow. The tetra-acetates may be made by oxidizing the corresponding dimethyl compound with chromium trioxide and sulphuric acid in the presence of acetic acid and anhydride. In examples: (1) terephthalaldehyde tetra-acetate is reacted in aqueous ethanol with hydrazine sulphate in the presence of sulphuric acid, (5) 4-methoxy-isophthalaldehyde is reacted in aqueous ethanol with hydrazine sulphate, (6) 2,5-dichloro-terephthalaldehyde tetra-acetate is reacted in aqueous ethanol with hydrazine hydrate in the presence of sulphuric acid, (7) 5-acetoxy-isophthalaldehyde tetra-acetate is reacted in aqueous ethanol with hydrazine sulphate and (8) 2,5-dibromo-terephthaldehyde in aqueousethanol is reacted with hydrazine sulphate.ALSO:Insoluble coloured polyazines used in dyeing processes are made by reacting hydrazine, its hydrate or a salt thereof with an aromatic p-or m-dialdehyde or a tetra-acetate thereof in substantially an aqueous medium, the hydrazine, its hydrate or its salt being used in the proportion of at least 1 mol. to 1 mol. of the dialdehyde. 80-90 DEG C. are preferred temperatures. Water-miscible organic solvents, e.g. a lower aliphatic alcohol, may be present. The dialdehyde may be substituted and specified dialdehydes are terephthal-, isophthal-, 4-methoxy-isophthal-, 2,5-dichloro-terephthal-, 5-hydroxy - isophthal-, 2,5 - dibromo - terephthal and 2,5-dimethoxy-terephthal-aldehyde. The pigments are yellow. The tetra-acetates may be made by oxidizing the corresponding dimethyl compound with chromium trioxide and sulphuric acid in the presence of acetic acid and anhydride. In the dyeing of textiles the polyazine may be caused to form on the materials, e.g. by impregnating with a solution of the dialdehyde, and after removal of excess liquid the material is run, with or without drying, through an aqueous solution containing the hydrazine compound, preferably at an elevated temperature, the fabric finally being washed and dried. Alternatively treatment with the hydrazine compound may precede that with dialdehyde. Pattern effects are produced by applying one or both reagents in selected areas only. The polyazine may be caused to form subsequently, e.g. by steaming, tetraacetates being particularly useful in this respect since they require hydrolysis before they react. In examples: (1) terephthalaldehyde tetraacetate is reacted in aqueous ethanol with hydrazine sulphate in the presence of sulphuric acid; (5) 4-methoxy-isophthalaldehyde is reacted in aqueous ethanol with hydrazine sulphate; (6) 2,5-dichloro-terephthalaldehyde tetra-acetate is reacted in aqueous ethanol with hydrazine hydrate in the presence of sulphuric acid; (7) 5-acetoxy-isophthalaldehyde tetraacetate is reacted in aqueous ethanol with hydrazine sulphate and (8) 2,5-dibromo-terephthalaldehyde in aqueous-ethanol is reacted with hydrazine sulphate; in (2) a cotton fabric is impregnated with a 5 per cent aqueous ethanol solution of terephthalaldehyde and run through a 5 per cent aqueous solution of hydrazine sulphate to be dyed a bright lemon yellow; (3) a cotton fabric is impregnated with a solution containing terephthalaldehyde tetraacetate and hydrazine hydrate, dried and the colour developed by passing through steam and formic acid vapour; (4) a cotton fabric is printed with a paste containing terephthalaldehyde tetracetate, hydrazine hydrate and tragacanth thickening, dried and steamed to develop the colour and in (9) a cotton fabric is impregnated with an aqueous alcohol solution of 2,5-dimethoxy terephthalaldehyde, dried and further impregnated with an aqueous solution of hydrazine sulphate, dried and steamed to yield an orange dyeing.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2829050A GB694451A (en) | 1950-11-20 | 1950-11-20 | Improvements relating to polyazine dyestuffs |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2829050A GB694451A (en) | 1950-11-20 | 1950-11-20 | Improvements relating to polyazine dyestuffs |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB694451A true GB694451A (en) | 1953-07-22 |
Family
ID=10273305
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2829050A Expired GB694451A (en) | 1950-11-20 | 1950-11-20 | Improvements relating to polyazine dyestuffs |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB694451A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2953987A4 (en) * | 2013-02-06 | 2016-09-28 | Avertica Inc | POLYMERS, SUBSTRATES, METHODS OF MAKING SAME, AND DEVICES COMPRISING SAME |
-
1950
- 1950-11-20 GB GB2829050A patent/GB694451A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2953987A4 (en) * | 2013-02-06 | 2016-09-28 | Avertica Inc | POLYMERS, SUBSTRATES, METHODS OF MAKING SAME, AND DEVICES COMPRISING SAME |
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