GB741638A - Improvements relating to chromium containing monoazo dyestuffs and their use - Google Patents
Improvements relating to chromium containing monoazo dyestuffs and their useInfo
- Publication number
- GB741638A GB741638A GB24427/53A GB2442753A GB741638A GB 741638 A GB741638 A GB 741638A GB 24427/53 A GB24427/53 A GB 24427/53A GB 2442753 A GB2442753 A GB 2442753A GB 741638 A GB741638 A GB 741638A
- Authority
- GB
- United Kingdom
- Prior art keywords
- ethyl
- dyestuffs
- methyl
- dyestuff
- diazotised
- 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
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 title abstract 2
- 229910052804 chromium Inorganic materials 0.000 title abstract 2
- 239000011651 chromium Substances 0.000 title 1
- 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 1
- 239000000975 dye Substances 0.000 abstract 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 4
- -1 methyl- Chemical group 0.000 abstract 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 3
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 abstract 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 abstract 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 abstract 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract 2
- 150000001340 alkali metals Chemical class 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 230000007935 neutral effect Effects 0.000 abstract 2
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 abstract 1
- CDULGHZNHURECF-UHFFFAOYSA-N 2,3-dimethylaniline 2,4-dimethylaniline 2,5-dimethylaniline 2,6-dimethylaniline 3,4-dimethylaniline 3,5-dimethylaniline Chemical class CC1=CC=C(N)C(C)=C1.CC1=CC=C(C)C(N)=C1.CC1=CC(C)=CC(N)=C1.CC1=CC=C(N)C=C1C.CC1=CC=CC(N)=C1C.CC1=CC=CC(C)=C1N CDULGHZNHURECF-UHFFFAOYSA-N 0.000 abstract 1
- NAZDVUBIEPVUKE-UHFFFAOYSA-N 2,5-dimethoxyaniline Chemical compound COC1=CC=C(OC)C(N)=C1 NAZDVUBIEPVUKE-UHFFFAOYSA-N 0.000 abstract 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical group COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 abstract 1
- YZQHOJYVBYWZTE-UHFFFAOYSA-N 3-piperidin-1-ylsulfonylnaphthalen-1-ol Chemical compound OC1=CC(=CC2=CC=CC=C12)S(=O)(=O)N1CCCCC1 YZQHOJYVBYWZTE-UHFFFAOYSA-N 0.000 abstract 1
- KUHCRHSZTINOMX-UHFFFAOYSA-N 4-hydroxy-N,N-dimethylnaphthalene-2-sulfonamide Chemical compound CN(S(=O)(=O)C=1C=C(C2=CC=CC=C2C1)O)C KUHCRHSZTINOMX-UHFFFAOYSA-N 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 abstract 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 1
- RGCKGOZRHPZPFP-UHFFFAOYSA-N alizarin Chemical compound C1=CC=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1 RGCKGOZRHPZPFP-UHFFFAOYSA-N 0.000 abstract 1
- 150000003863 ammonium salts Chemical class 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 239000007900 aqueous suspension Substances 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 239000004202 carbamide Substances 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 150000001845 chromium compounds Chemical class 0.000 abstract 1
- GRWVQDDAKZFPFI-UHFFFAOYSA-H chromium(III) sulfate Chemical compound [Cr+3].[Cr+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O GRWVQDDAKZFPFI-UHFFFAOYSA-H 0.000 abstract 1
- 235000015217 chromium(III) sulphate Nutrition 0.000 abstract 1
- 239000011696 chromium(III) sulphate Substances 0.000 abstract 1
- 230000008878 coupling Effects 0.000 abstract 1
- 238000010168 coupling process Methods 0.000 abstract 1
- 238000005859 coupling reaction Methods 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 1
- 125000001664 diethylamino group Chemical class [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 abstract 1
- 239000002270 dispersing agent Substances 0.000 abstract 1
- 229910052736 halogen Chemical group 0.000 abstract 1
- 150000002367 halogens Chemical group 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 229920001184 polypeptide Polymers 0.000 abstract 1
- 102000004196 processed proteins & peptides Human genes 0.000 abstract 1
- 108090000765 processed proteins & peptides Proteins 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 150000003456 sulfonamides Chemical class 0.000 abstract 1
- 150000004992 toluidines Chemical class 0.000 abstract 1
- 238000009736 wetting Methods 0.000 abstract 1
- 239000000080 wetting agent Substances 0.000 abstract 1
- 210000002268 wool Anatomy 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)
- Coloring (AREA)
Abstract
The invention comprises chromium compounds of the formula [D-Cr-D]M2 where M2 is an alkali metal or ammonium cation and D is a dyestuff which has no water solubilising groups which dissociate acid in neutral water of formula <FORM:0741638/IV(c)/1> where R is an unsubstituted or substituted alkyl group having a total of at most 4 C atoms, X is hydrogen or halogen, Y1 is H or an alkyl, cycloalkyl or phenyl group and Y2 is H or an alkyl group and Y1 and Y2 may be found together in the form of a ring by themselves or with oxygen. They may be made by treating dyestuffs of the above formula in which the hydrogen group of the benzene ring is replaced by OR1 where R1 is as R with chromium-yielding agents so that there is 1 chromium atom to two dyestuff molecules and under conditions to remove R1. Preferably R and R1 are hydroxyl substituted alkyl groups which may be etherized. The unmetallized dyestuffs may be made by coupling the diazotised 2, 5-dialkoxy amine with the appropriate naphthol advantageously in an alkaline medium. Specified amines from which the sulphonamides may be derived are methyl-, ethyl-, propyl-, butyl, cyclohexyl-, dimethyl- and diethyl-amines, aniline, toluidines, xylidines, anisdines, phenetidines, piperidine, morpholine and monomethyl and -ethyl-aniline. Chroming may be effected with chromic sulphate, formate and acetate and alkali metal and ammonium salts of chromosalicylic acid, advantageously at over 100 DEG C in aqueous solution or suspension under pressure preferably in the presence of a wetting or dispersing agent such as turkey red oil at 120-150 DEG C. Chroming may also be effected in alcohol under pressure or in solvents such as ethylene glycol, ethylene glycol monomethyl- or monoethyl-ether, formamide, acetamide or in a urea melt at 135-155 DEG C. The dyestuffs dye wool and synthetic polypeptide fibres from a neutral to weakly acid bath in blue shades. In Examples (1) diazotised 1-amino-, 5-dimethoxy benzene or its 4-chloro-derivative are coupled with 1-hydroxynaphthalene-3-sulphonic acid dimethylamide and the resulting dyestuff chromed; (2) diazotised 1-amino-2, 5-dimethoxy benzene is coupled with 1 - hydroxynaphthalene-3-sulphonic acid piperidide and the resulting dyestuff chromed. In a Table showing chromed dyestuffs preparable as in the Examples the following values are given for R and R1, methyl, ethyl and hydroxyethel, for X, H and C1, for Y2, H, methyl and ethyl, for Y1, H, methyl, ethyl, phenyl, cyclohexyl and Y1 and Y2 combined as a morpholine residue.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH741638X | 1952-09-10 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB741638A true GB741638A (en) | 1955-12-07 |
Family
ID=4533216
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB24427/53A Expired GB741638A (en) | 1952-09-10 | 1953-09-03 | Improvements relating to chromium containing monoazo dyestuffs and their use |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB741638A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102718636A (en) * | 2012-06-11 | 2012-10-10 | 武汉旭日华科技发展有限公司 | Recovering and processing method of ethylene glycol monoethyl ether waste liquid containing 2:1 type chromium complex dye and by-product thereof |
-
1953
- 1953-09-03 GB GB24427/53A patent/GB741638A/en not_active Expired
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102718636A (en) * | 2012-06-11 | 2012-10-10 | 武汉旭日华科技发展有限公司 | Recovering and processing method of ethylene glycol monoethyl ether waste liquid containing 2:1 type chromium complex dye and by-product thereof |
CN102718636B (en) * | 2012-06-11 | 2014-06-25 | 武汉旭日华科技发展有限公司 | Recovering and processing method of ethylene glycol monoethyl ether waste liquid containing 2:1 type chromium complex dye and by-product thereof |
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