GB1074028A - Dyestuffs of the amino-anthraquinone series - Google Patents
Dyestuffs of the amino-anthraquinone seriesInfo
- Publication number
- GB1074028A GB1074028A GB4993465A GB4993465A GB1074028A GB 1074028 A GB1074028 A GB 1074028A GB 4993465 A GB4993465 A GB 4993465A GB 4993465 A GB4993465 A GB 4993465A GB 1074028 A GB1074028 A GB 1074028A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- dyes
- anthraquinone
- radical
- alkyl
- 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
- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical class O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 title 1
- -1 anthraquinone compounds Chemical class 0.000 abstract 7
- 239000000975 dye Substances 0.000 abstract 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 6
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 abstract 4
- 150000004056 anthraquinones Chemical class 0.000 abstract 4
- QAMCXJOYXRSXDU-UHFFFAOYSA-N 2,4-dimethoxy-n-[2-(1,3,3-trimethylindol-1-ium-2-yl)ethenyl]aniline;chloride Chemical compound [Cl-].COC1=CC(OC)=CC=C1NC=CC1=[N+](C)C2=CC=CC=C2C1(C)C QAMCXJOYXRSXDU-UHFFFAOYSA-N 0.000 abstract 2
- 229920002972 Acrylic fiber Polymers 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000003277 amino group Chemical group 0.000 abstract 2
- 150000001449 anionic compounds Chemical class 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 150000005840 aryl radicals Chemical group 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 2
- 150000002790 naphthalenes Chemical class 0.000 abstract 2
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 2
- 150000002891 organic anions Chemical class 0.000 abstract 2
- NMZZABJWNUABDN-UHFFFAOYSA-N 1-bromo-4-(4-methylanilino)anthracene-9,10-dione Chemical compound BrC1=CC=C(C=2C(C3=CC=CC=C3C(C12)=O)=O)NC1=CC=C(C=C1)C NMZZABJWNUABDN-UHFFFAOYSA-N 0.000 abstract 1
- 241000974482 Aricia saepiolus Species 0.000 abstract 1
- 229920001353 Dextrin Polymers 0.000 abstract 1
- 239000004375 Dextrin Substances 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 230000002378 acidificating effect Effects 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 239000001000 anthraquinone dye Substances 0.000 abstract 1
- IPTLKMXBROVJJF-UHFFFAOYSA-N azanium;methyl sulfate Chemical compound N.COS(O)(=O)=O IPTLKMXBROVJJF-UHFFFAOYSA-N 0.000 abstract 1
- 239000011230 binding agent Substances 0.000 abstract 1
- 235000019425 dextrin Nutrition 0.000 abstract 1
- 150000004985 diamines Chemical class 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 abstract 1
- 238000004043 dyeing Methods 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 229920002239 polyacrylonitrile Polymers 0.000 abstract 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 abstract 1
- 125000001453 quaternary ammonium group Chemical group 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 239000004094 surface-active agent Substances 0.000 abstract 1
- 239000004753 textile 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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
- C09B1/32—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups
- C09B1/325—Dyes with no other substituents than the amino groups
-
- 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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/207—Dyes with amino groups and with onium groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Coloring (AREA)
Abstract
The invention comprises anthraquinone compounds of the formula <FORM:1074028/C4-C5/1> and their quaternary derivatives of the formula <FORM:1074028/C4-C5/2> wherein R1 is an aryl radical of the benzene or naphthalene series containing at least one halogen substituent in a position ortho to the amino group; R2 is a 1,4-phenylene radical or a C2-C4 alkylene radical; R3 and R4 are alkyl radicals or, together with the N atom to which they are attached, form a heterocyclic ring; R5 is alkyl, hydroxyalkyl, cycloalkyl or aralkyl; and A\sK is an inorganic or organic anion. They may be obtained by condensing a diamine of formula <FORM:1074028/C4-C5/3> with a 1-(o-haloarylamino) anthraquinone derivative of the formula <FORM:1074028/C4-C5/4> wherein X is a replaceable substituent, e.g. halogen, NO2 or lower alkoxy, in the presence of a condensing agent and a weak acid-binding agent in an inert organic diluent, and if desired, converting the anthraquinone base formed to the quaternary ammonium dyestuff by treating with a quaternizing agent in the presence of a solvent. Several anthraquinones of the first formula above are specified. An example is given for the preparation of 1-(21 - bromo - 41 - methylanilino) - 4 -(31-dimethylaminopropylamino) anthraquinone and the quaternary ammonium compound obtained by treatment with dimethyl sulphate. The dyes are useful for dyeing acrylic fibres greenish-blue shades and in conjunction with CI Basic Yellow 11 to give a green shade. The corresponding unhalogenated dyestuff trimethyl - (3 - [41 - p - toluidino - 11 -anthraquinonyl]aminopropyl) ammonium methyl sulphate is obtained by a similar method from 1 - p - toluidino - 4 - bromoanthraquinone and dyes acrylic fibres reddish-blue shades.ALSO:Polyacrylonitrile textiles are dyed with anthraquinone dyes of the formula: <FORM:1074028/D1-D2/1> where R1 is an aryl radical of the benzene or naphthalene series containing at least one halogen substituent in an o-position to the amino group; R2 is a 1,4-phenylene radical or a C2-C4 alkylene radical; R3 and R4 are alkyl radicals or together with the N atom form a heterocyclic ring; R5 is alkyl, hydroxyalkyl, cycloalkyl or aralkyl; and A is an inorganic or organic anion. The dyes are preferably applied from mildly acidic aqueous dyebaths which may contain a surface active agent. In an Example the dye is previously mixed with dextrin and pulverised. Other dyes may be present such as CI basic yellow 11.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US41612464A | 1964-12-04 | 1964-12-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1074028A true GB1074028A (en) | 1967-06-28 |
Family
ID=23648645
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4993465A Expired GB1074028A (en) | 1964-12-04 | 1965-11-24 | Dyestuffs of the amino-anthraquinone series |
Country Status (4)
| Country | Link |
|---|---|
| CH (1) | CH1672265A4 (en) |
| DE (1) | DE1469598A1 (en) |
| FR (1) | FR1459493A (en) |
| GB (1) | GB1074028A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4123222A (en) | 1976-03-23 | 1978-10-31 | Ciba-Geigy Corporation | Process for the dyeing or printing of polyacrylonitrile material |
| WO2019223015A1 (en) * | 2018-05-25 | 2019-11-28 | 苏州大学张家港工业技术研究院 | Precursor of blue anthraquinone active disperse dye and preparation method therefor |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2533428A1 (en) * | 1975-07-25 | 1977-02-10 | Bayer Ag | CATIONIC COLORS |
-
1965
- 1965-11-24 GB GB4993465A patent/GB1074028A/en not_active Expired
- 1965-12-03 FR FR40907A patent/FR1459493A/en not_active Expired
- 1965-12-03 CH CH1672265D patent/CH1672265A4/en unknown
- 1965-12-03 DE DE19651469598 patent/DE1469598A1/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4123222A (en) | 1976-03-23 | 1978-10-31 | Ciba-Geigy Corporation | Process for the dyeing or printing of polyacrylonitrile material |
| WO2019223015A1 (en) * | 2018-05-25 | 2019-11-28 | 苏州大学张家港工业技术研究院 | Precursor of blue anthraquinone active disperse dye and preparation method therefor |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1469598A1 (en) | 1968-12-05 |
| CH1672265A4 (en) | 1967-05-13 |
| FR1459493A (en) | 1966-11-18 |
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