GB852517A - New vat dyestuffs of the anthraquinone series and a process for their manufacture - Google Patents
New vat dyestuffs of the anthraquinone series and a process for their manufactureInfo
- Publication number
- GB852517A GB852517A GB36163/56A GB3616356A GB852517A GB 852517 A GB852517 A GB 852517A GB 36163/56 A GB36163/56 A GB 36163/56A GB 3616356 A GB3616356 A GB 3616356A GB 852517 A GB852517 A GB 852517A
- Authority
- GB
- United Kingdom
- Prior art keywords
- chloride
- amino
- pentyl
- give
- vat
- 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
- 238000000034 method Methods 0.000 title abstract 2
- 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
- 238000004519 manufacturing process Methods 0.000 title 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 9
- 239000000975 dye Substances 0.000 abstract 5
- 239000003795 chemical substances by application Substances 0.000 abstract 3
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 235000011118 potassium hydroxide Nutrition 0.000 abstract 3
- BIZVHVKTTCPVPP-UHFFFAOYSA-N 1-amino-9,10-dioxoanthracene-2-carbonyl chloride Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC(C(Cl)=O)=C2N BIZVHVKTTCPVPP-UHFFFAOYSA-N 0.000 abstract 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 2
- 229920000742 Cotton Polymers 0.000 abstract 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 abstract 2
- 125000004442 acylamino group Chemical group 0.000 abstract 2
- 230000001476 alcoholic effect Effects 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 238000002844 melting Methods 0.000 abstract 2
- 230000008018 melting Effects 0.000 abstract 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 abstract 2
- 229910052708 sodium Inorganic materials 0.000 abstract 2
- 239000011734 sodium Substances 0.000 abstract 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 abstract 2
- KLTVSWGXIAYTHO-UHFFFAOYSA-N 1-Octen-3-one Chemical compound CCCCCC(=O)C=C KLTVSWGXIAYTHO-UHFFFAOYSA-N 0.000 abstract 1
- RZNHSEZOLFEFGB-UHFFFAOYSA-N 2-methoxybenzoyl chloride Chemical compound COC1=CC=CC=C1C(Cl)=O RZNHSEZOLFEFGB-UHFFFAOYSA-N 0.000 abstract 1
- SYVNVEGIRVXRQH-UHFFFAOYSA-N 3-fluorobenzoyl chloride Chemical compound FC1=CC=CC(C(Cl)=O)=C1 SYVNVEGIRVXRQH-UHFFFAOYSA-N 0.000 abstract 1
- 229920002955 Art silk Polymers 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- 240000007817 Olea europaea Species 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- RJGDLRCDCYRQOQ-UHFFFAOYSA-N anthrone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3CC2=C1 RJGDLRCDCYRQOQ-UHFFFAOYSA-N 0.000 abstract 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 abstract 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract 1
- 230000031709 bromination Effects 0.000 abstract 1
- 238000005893 bromination reaction Methods 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 238000005660 chlorination reaction Methods 0.000 abstract 1
- 150000001805 chlorine compounds Chemical class 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 238000004043 dyeing Methods 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- FWEQPMZEKHHFTB-UHFFFAOYSA-N n-(5-amino-9,10-dioxoanthracen-1-yl)benzamide Chemical compound C1=CC=C2C(=O)C=3C(N)=CC=CC=3C(=O)C2=C1NC(=O)C1=CC=CC=C1 FWEQPMZEKHHFTB-UHFFFAOYSA-N 0.000 abstract 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 239000007800 oxidant agent Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- -1 sodium anilide Chemical class 0.000 abstract 1
- 229910000029 sodium carbonate Inorganic materials 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- 239000000984 vat dye Substances 0.000 abstract 1
- 235000013311 vegetables Nutrition 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
- C09B3/00—Dyes with an anthracene nucleus condensed with one or more carbocyclic rings
- C09B3/02—Benzathrones
- C09B3/06—Preparation from starting materials already containing the benzanthrone nucleus
-
- 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
- C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
- C09B5/24—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic rings being only condensed with an anthraquinone nucleus in 1-2 or 2-3 position
- C09B5/34—Anthraquinone acridones or thioxanthrones
- C09B5/40—Condensation products of benzanthronyl-amino-anthraquinones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Bz-1-bromo-Bz-2-methyl-, methyl- or -isopropylbenzanthrone and Bz-1-chloro-Bz-2-isopropyl- or -n-pentyl-benzanthrone are made by brominating or chlorinating the corresponding Bz-2-alkylbenzanthrones. The bromination and chlorination may be conducted using bromine and sulphuryl chloride in chloroform or sulphuryl chloride in chlorbenzene respectively. Bz-2-isopropyl- or -n-pentyl-benzanthrone is made by condensing anthrone with alphaisopropyl- or alpha-n-pentyl-acrolein respectively. The condensation may be conducted in sulphuric acid in the presence of an oxidising agent.ALSO:The invention comprises vat dyestuffs of the formula: <FORM:0852517/IV (c)/1> where R is alkyl or aryl and R1 is amino or acylamino, and a process for making them by reacting a Bz-1-halogen-benzanthrone substituted by an alkyl or aryl group in the Bz-2-position with a 1 : 5- diaminoanthrquinone or an N-monoacyl compound thereof to give a compound of the formula: p <FORM:0852517/IV (c)/2> which is then melted with an alkaline condensing agent, such as alcoholic caustic potash, and reacting the product, if desired, with an acylating agent such as benzoyl chloride, m- or pchloro-, o- or mfluoro-, or methoxybenzoyl chloride, o-, m- or ptoluyl chloride, a - or b - naphthoyl chloride or 1 - aminoanthraquinone - 2 - carboxylic acid chloride. Hydrolysis of the acylamino group to form an amino group when using alcoholic potassium hydroxide in the melting step can be avoided if desired by melting the benzanthronylamino-5-acylaminoanthraquinone with an alkaline condensing agent substantially free from hydroxyl groups, such as sodium anilide or a sodium alcoholate, in aniline at about 140 DEG -170 DEG C. In examples (1), Bz - 1 - bromo -Bz -2- ethylbenzanthrone is reacted with 1-amino -5- benzoylaminoanthraquinone in nitrobenzene with copper powder and sodium carbonate to give Bz -2- ethyl- Bz -1- benzanthronyl -1- amino -5- benzoylaminoanthraquinone which is melted with caustic potash and monethanolamine, the leuco compound thus obtained being oxidized with air to give a vat dyestuff which dyes cotton grey, and (2) this dyestuff is treated with m-fluorobenzoyl chloride in chlorobenzene to give a khaki cotton dye from a blue vat; in further examples, vat dyes dyeing vegetable fibres or artificial silk grey, khaki, brown and olive shades are made in a similar manner from 1- amino-5-benzoylamineanthraquinone and Bz -1- bromo- or Bz -1- chloro- Bz-2- hydrocarbonbenzanthrones, the hydrocarbon radicals being selected from methyl, ethyl, isopropyl, n-pentyl and phenyl, and the dyes being acylated with benzoyl, mfluoro-, mchloro- or mmethoxybenzoyl chlorides or 1- aminoanthraquinone -2- carboxylic acid chloride. Specification 339,369 is referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1955F0018927 DE1070314B (en) | 1955-11-26 | 1955-11-26 | Process for the production of vat dyes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB852517A true GB852517A (en) | 1960-10-26 |
Family
ID=595235
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB36163/56A Expired GB852517A (en) | 1955-11-26 | 1956-11-26 | New vat dyestuffs of the anthraquinone series and a process for their manufacture |
Country Status (5)
| Country | Link |
|---|---|
| CH (1) | CH347923A (en) |
| DE (1) | DE1070314B (en) |
| FR (1) | FR1167835A (en) |
| GB (1) | GB852517A (en) |
| NL (1) | NL94007C (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103897424A (en) * | 2014-03-27 | 2014-07-02 | 重庆华彩化工有限责任公司 | Preparation method of vat olive green B dye |
| CN114517021A (en) * | 2022-03-07 | 2022-05-20 | 赤峰市恒祥化工有限公司 | Novel gray vat dye and preparation method and application thereof |
-
0
- NL NL94007D patent/NL94007C/xx active
-
1955
- 1955-11-26 DE DE1955F0018927 patent/DE1070314B/en active Pending
-
1956
- 1956-11-24 CH CH347923D patent/CH347923A/en unknown
- 1956-11-26 FR FR1167835D patent/FR1167835A/en not_active Expired
- 1956-11-26 GB GB36163/56A patent/GB852517A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103897424A (en) * | 2014-03-27 | 2014-07-02 | 重庆华彩化工有限责任公司 | Preparation method of vat olive green B dye |
| CN103897424B (en) * | 2014-03-27 | 2016-04-06 | 重庆华彩化工有限责任公司 | A kind of preparation method of Vat Olive Green B dyestuff |
| CN114517021A (en) * | 2022-03-07 | 2022-05-20 | 赤峰市恒祥化工有限公司 | Novel gray vat dye and preparation method and application thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CH347923A (en) | 1960-07-31 |
| FR1167835A (en) | 1958-12-01 |
| NL94007C (en) | |
| DE1070314B (en) | 1959-12-03 |
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