GB1473015A - Water-insoluble red anthraquinone dyes - Google Patents
Water-insoluble red anthraquinone dyesInfo
- Publication number
- GB1473015A GB1473015A GB3352074A GB3352074A GB1473015A GB 1473015 A GB1473015 A GB 1473015A GB 3352074 A GB3352074 A GB 3352074A GB 3352074 A GB3352074 A GB 3352074A GB 1473015 A GB1473015 A GB 1473015A
- Authority
- GB
- United Kingdom
- Prior art keywords
- anthraquinone
- reacting
- amino
- alkyl
- alcohol
- 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
- 239000001000 anthraquinone dye Substances 0.000 title abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 abstract 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 abstract 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 150000001350 alkyl halides Chemical class 0.000 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 abstract 2
- 239000003153 chemical reaction reagent Substances 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 239000000975 dye Substances 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- QUXBARPXUAPKDG-UHFFFAOYSA-N 1-amino-2,4-dihydroxyanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=CC(O)=C2N QUXBARPXUAPKDG-UHFFFAOYSA-N 0.000 abstract 1
- 125000000579 2,2-diphenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(C1=C([H])C([H])=C([H])C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 abstract 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-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
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 abstract 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000004793 Polystyrene Substances 0.000 abstract 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical class [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 1
- 125000005396 acrylic acid ester group Chemical group 0.000 abstract 1
- 150000004056 anthraquinones Chemical class 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
- 150000004649 carbonic acid derivatives Chemical class 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 229920001577 copolymer Polymers 0.000 abstract 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 abstract 1
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- MBHINSULENHCMF-UHFFFAOYSA-N n,n-dimethylpropanamide Chemical compound CCC(=O)N(C)C MBHINSULENHCMF-UHFFFAOYSA-N 0.000 abstract 1
- 125000003884 phenylalkyl group Chemical group 0.000 abstract 1
- 239000002798 polar solvent Substances 0.000 abstract 1
- 229920000728 polyester Polymers 0.000 abstract 1
- 229920002223 polystyrene Polymers 0.000 abstract 1
- 235000011118 potassium hydroxide Nutrition 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 235000011121 sodium hydroxide 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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
- C09B1/54—Amino-hydroxy-anthraquinones; Ethers and esters thereof etherified
- C09B1/545—Anthraquinones with aliphatic, cycloaliphatic or araliphatic ether 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
- C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
- C09B1/503—Amino-hydroxy-anthraquinones; Ethers and esters thereof unsubstituted amino-hydroxy anthraquinone
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1473015 Anthraquinone dyes BASF AG 30 July 1974 [1 Aug 1973] 33520/74 Heading C4P The invention comprises red anthraquinone dyes of the general formula wherein X is a group or -CH(R<SP>1</SP>)CH(R<SP>2</SP>)R<SP>3</SP> wherein R<SP>1</SP> is H, alkyl or optionally substituted phenyl, R<SP>2</SP> is H or phenyl and R<SP>3</SP> is H, alkyl, phenylalkyl, diphenylmethyl or 2,2-diphenylethyl at least one of R<SP>1</SP>, R<SP>2</SP> and R<SP>3</SP> containing a benzene ring. They are prepared by (a) reacting a 1-amino-4- hydroxy - 2 - alkoxy - or 2 - aryloxy - anthraquinone with an alcohol HOCH 2 X where X is as above in presence of an alkaline agent either in an excess of the alcohol or in an inert aprotic polar water-miscible solvent, (b) reacting a 1- amino - 2 - halo - 4 - hydroxy - anthraquinone with an alcohol HOCH 2 X where X is as above in presence of a phenol and at least 1 mol equivalent based on the anthraquinone of an alkaline reagent or (c) reacting 1-amino-2,4- dihydroxyanthraquinone with an alkyl halide Hal-CH 2 -X where Hal is chlorine or bromine and X is as above in presence of at least one equivalent of an alkaline reagent per mole alkyl halide in an inert aprotic polar solvent. The alkaline agents are sodium and potassium hydroxides, carbonates and bicarbonates and sodium methylate and the solvents include dimethylsulphoxide, N,N-dimethylformamide, N, N - dimethylacetamide, N,N - dimethylpropionamide, N - methylpyrrolidone and mixtures thereof. The dyes dye polyester fibres and mass colour polystyrene, copolymers of styrene, acrylonitrile and butadiene and/or acrylic acid esters and P.V.C.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19732338929 DE2338929A1 (en) | 1973-08-01 | 1973-08-01 | WATER-INSOLUBLE RED ANTHRAQUINONE DYES |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1473015A true GB1473015A (en) | 1977-05-11 |
Family
ID=5888549
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3352074A Expired GB1473015A (en) | 1973-08-01 | 1974-07-30 | Water-insoluble red anthraquinone dyes |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS5038231A (en) |
| CH (1) | CH584254A5 (en) |
| DE (1) | DE2338929A1 (en) |
| FR (1) | FR2239507B3 (en) |
| GB (1) | GB1473015A (en) |
| IT (1) | IT1018758B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5421773U (en) * | 1977-07-15 | 1979-02-13 | ||
| IT1266113B1 (en) * | 1993-08-02 | 1996-12-20 | Nordica Spa | PROCEDURE FOR OBTAINING INJECTED ELEMENTS PRESENTING PREDETERMINABLE OPACITY OR TRANSPARENCY |
-
1973
- 1973-08-01 DE DE19732338929 patent/DE2338929A1/en active Pending
-
1974
- 1974-07-29 CH CH1042674A patent/CH584254A5/xx not_active IP Right Cessation
- 1974-07-30 GB GB3352074A patent/GB1473015A/en not_active Expired
- 1974-07-30 IT IT52341/74A patent/IT1018758B/en active
- 1974-07-31 FR FR7426579A patent/FR2239507B3/fr not_active Expired
- 1974-08-01 JP JP49087600A patent/JPS5038231A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| FR2239507B3 (en) | 1977-06-03 |
| IT1018758B (en) | 1977-10-20 |
| JPS5038231A (en) | 1975-04-09 |
| FR2239507A1 (en) | 1975-02-28 |
| CH584254A5 (en) | 1977-01-31 |
| DE2338929A1 (en) | 1975-02-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |