GB1061025A - Disperse dyes of the anthraquinone series - Google Patents
Disperse dyes of the anthraquinone seriesInfo
- Publication number
- GB1061025A GB1061025A GB4367463A GB4367463A GB1061025A GB 1061025 A GB1061025 A GB 1061025A GB 4367463 A GB4367463 A GB 4367463A GB 4367463 A GB4367463 A GB 4367463A GB 1061025 A GB1061025 A GB 1061025A
- Authority
- GB
- United Kingdom
- Prior art keywords
- carbon atoms
- methyl
- formula
- dinitrated
- carboxy
- 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
- 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 title 1
- 150000004056 anthraquinones Chemical class 0.000 title 1
- 239000000986 disperse dye Substances 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 5
- QBPFLULOKWLNNW-UHFFFAOYSA-N chrysazin Chemical compound O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O QBPFLULOKWLNNW-UHFFFAOYSA-N 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 239000000975 dye Substances 0.000 abstract 3
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- JPICKYUTICNNNJ-UHFFFAOYSA-N anthrarufin Chemical compound O=C1C2=C(O)C=CC=C2C(=O)C2=C1C=CC=C2O JPICKYUTICNNNJ-UHFFFAOYSA-N 0.000 abstract 2
- 125000004966 cyanoalkyl group Chemical group 0.000 abstract 2
- 229960001577 dantron Drugs 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 abstract 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 1
- 239000004411 aluminium Substances 0.000 abstract 1
- 229910052782 aluminium Inorganic materials 0.000 abstract 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 abstract 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 1
- 150000007942 carboxylates Chemical class 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000001188 haloalkyl group Chemical group 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 abstract 1
- KBOPZPXVLCULAV-UHFFFAOYSA-N mesalamine Chemical compound NC1=CC=C(O)C(C(O)=O)=C1 KBOPZPXVLCULAV-UHFFFAOYSA-N 0.000 abstract 1
- 229960004963 mesalazine Drugs 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 239000000049 pigment Substances 0.000 abstract 1
- 150000003254 radicals Chemical class 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 229910052725 zinc Inorganic materials 0.000 abstract 1
- 239000011701 zinc Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0041—Optical brightening agents, organic pigments
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/32—Compounds containing nitrogen bound to oxygen
-
- 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
- C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
-
- 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
- C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
- C09B1/51—N-substituted amino-hydroxy anthraquinone
- C09B1/514—N-aryl derivatives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Coloring (AREA)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises dyes of the formula I <FORM:1061025/C4-C5/1> wherein A has the structure of the formula <FORM:1061025/C4-C5/2> B has the structure of the formula <FORM:1061025/C4-C5/3> each X is halogen, alkyl, alkoxy, hydroxyalkoxyalkyl or cyanoalkyl of up to 5 carbon atoms, hydroxyalkyl of 2 to 5 carbon atoms or a 2 : 3-benz radical, optionally further substituted by halogen, alkyl, alkoxy of 1 to 5 carbon atoms, halogenoalkyl or carbamoyl, R is alkyl, cyanoalkyl or hydroxyalkoxyalkyl of up to 5 carbon atoms or hydroxyalkyl of 2 to 5 carbon atoms, Z is hydrogen or methyl, a is 0, 1, 2 or 3, b, c, m and n are each 0 or 1 and b+c and m+n both equal 1. The dyes are made by heating together in a solvent compounds of the formula A-H or B-H with 4 : 5-dinitro-1 : 8-dihydroxy- or 4 : 8 - dinitro - 1 : 5 - dihydroxyanthraquinones or with crude dinitrated chrysazin or anthrarufin. The dyes form pigments by reaction in solution with metal carboxylates, e.g. of aluminium and zinc. In examples, 1 : 5 - dihydroxy - 8 - nitroanthraquinones having in the 4-position a phenylamino, 21-, 31-or 41-methylphenylamino, 41-methoxyphenylamino or a -naphthylamino radical also substituted at the amino nitrogen by methyl, ethyl, n-propyl, n-butyl, isopentyl or hydroxyethyl or having in the 4-position a 31-carboxy-41-hydroxy-, 31-hydroxy-41-carboxy- or 31-methyl - 41 - hydroxy - 51 - carboxy - phenylamino group are described, as also are dyestuffs made by reacting N-methyl-aniline or 5-aminosalicylic acid with crude dinitrated chrysazin or crude dinitrated anthrarufin.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US24399562A | 1962-12-12 | 1962-12-12 | |
| US24458762A | 1962-12-14 | 1962-12-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1061025A true GB1061025A (en) | 1967-03-08 |
Family
ID=26936245
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4367463A Expired GB1061025A (en) | 1962-12-12 | 1963-11-05 | Disperse dyes of the anthraquinone series |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS4819597B1 (en) |
| BE (1) | BE635938A (en) |
| DE (1) | DE1444768A1 (en) |
| GB (1) | GB1061025A (en) |
| NL (1) | NL297395A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1045565A (en) * | 1964-06-08 | 1966-10-12 | Ici Ltd | Colouring linear polyesters |
| JPS61142578U (en) * | 1985-02-25 | 1986-09-03 |
-
0
- NL NL297395D patent/NL297395A/xx unknown
- BE BE635938D patent/BE635938A/xx unknown
-
1963
- 1963-10-29 DE DE19631444768 patent/DE1444768A1/en active Pending
- 1963-11-05 GB GB4367463A patent/GB1061025A/en not_active Expired
- 1963-12-11 JP JP38066474A patent/JPS4819597B1/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JPS4819597B1 (en) | 1973-06-14 |
| BE635938A (en) | |
| NL297395A (en) | |
| DE1444768A1 (en) | 1969-03-20 |
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