GB1348149A - Phthalocyanine dyestuffs and a process for their preparation - Google Patents
Phthalocyanine dyestuffs and a process for their preparationInfo
- Publication number
- GB1348149A GB1348149A GB1665971A GB1665971A GB1348149A GB 1348149 A GB1348149 A GB 1348149A GB 1665971 A GB1665971 A GB 1665971A GB 1665971 A GB1665971 A GB 1665971A GB 1348149 A GB1348149 A GB 1348149A
- Authority
- GB
- United Kingdom
- Prior art keywords
- groups
- alkyl
- formula
- phthalocyanine
- hydroxyalkyl
- 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
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 title abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-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
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- 125000003545 alkoxy group Chemical group 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- -1 phenoxy, naphthyloxy, amino Chemical group 0.000 abstract 3
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 abstract 1
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 abstract 1
- 239000004285 Potassium sulphite Substances 0.000 abstract 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 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
- 239000012736 aqueous medium Substances 0.000 abstract 1
- 239000004202 carbamide Substances 0.000 abstract 1
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 abstract 1
- 239000000975 dye Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- 125000005191 hydroxyalkylamino group Chemical group 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 abstract 1
- 125000005184 naphthylamino group Chemical group C1(=CC=CC2=CC=CC=C12)N* 0.000 abstract 1
- BHZRJJOHZFYXTO-UHFFFAOYSA-L potassium sulfite Chemical compound [K+].[K+].[O-]S([O-])=O BHZRJJOHZFYXTO-UHFFFAOYSA-L 0.000 abstract 1
- 235000019252 potassium sulphite Nutrition 0.000 abstract 1
- 235000010265 sodium sulphite 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
- C09B47/00—Porphines; Azaporphines
- C09B47/04—Phthalocyanines abbreviation: Pc
- C09B47/08—Preparation from other phthalocyanine compounds, e.g. cobaltphthalocyanineamine complex
- C09B47/24—Obtaining compounds having —COOH or —SO3H radicals, or derivatives thereof, directly bound to the phthalocyanine radical
- C09B47/26—Amide radicals
-
- 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
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
- C09B62/04—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a triazine ring
- C09B62/10—Porphines; Azaporphines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Abstract
1348149 Phthalocyanine dyestuffs VZYKUMNY USTAV ORGANICKYCH SYNTEZ 24 May 1971 [22 May 1970] 16659/71 Heading C4P The invention comprises phthalocyanine dyestuffs of the general formula where Pc represents a copper-phthalocyanine radical; A represents a C 2 -C 4 alkylene radical; R is a C 1 -C 4 alkyl or hydroxyalkyl, or hydroxyalkyl amino) alkyl group or a benzene or naphthalene radical which is optionally substituted by one or more C 1 -C 4 alkyl groups, C 1 -C 3 alkoxy groups or CO 2 H or SO 3 H groups or with a combination of two or more of said groups; R 1 and R 2 independently represent H, C 1 -C 4 alkyl or C 1 -C 4 hydroxyalkyl; X is Cl, SO 3 H, C 1 -C 3 alkoxy, phenoxy, naphthyloxy, amino, C 1 -C 3 alkylamino or phenyl- or naphthylamino; a is a number from 0-2; b is a number from 0À5-1À5; c is a number from 1-3 and the sum of a, b and c does not exceed 4. The dyes may be prepared by reacting a compound of formula where X<SP>1</SP> is Cl, C 1 -C 3 alkoxy, phenoxy, naphthoxy, NH 2 , C 1 -C 3 alkylamino or phenyl- or napthylamino with either (a) sodium sulphite or potassium sulphite or a mixture thereof or (b) SO 2 in an aqueous medium with dropwise addition of NaOH or KOH at 20-100‹ C. in the presence of urea or dimethylformamide, the hydroxide being added until a pH of 8À0-8À5 is achieved. The compounds of Formula V may be prepared by reacting the corresponding phthalocyanine containing a group -A-NHR 2 with a triazine of formula or with cyanuric chloride followed by reaction with ammonia or an amine to produce compounds where X<SP>1</SP> is NH 2 or a substituted amino group.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS357770 | 1970-05-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1348149A true GB1348149A (en) | 1974-03-13 |
Family
ID=5376251
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1665971A Expired GB1348149A (en) | 1970-05-22 | 1971-05-24 | Phthalocyanine dyestuffs and a process for their preparation |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1348149A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4280956A (en) | 1978-06-28 | 1981-07-28 | Bayer Aktiengesellschaft | Phthalocyanine reactive dyestuffs |
| EP0173476A3 (en) * | 1984-08-24 | 1988-07-20 | Imperial Chemical Industries Plc | Water-soluble dye |
| EP0596323A3 (en) * | 1992-11-02 | 1994-06-15 | Bayer Ag | Mixture of reactive phthalocyanine dyes |
-
1971
- 1971-05-24 GB GB1665971A patent/GB1348149A/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4280956A (en) | 1978-06-28 | 1981-07-28 | Bayer Aktiengesellschaft | Phthalocyanine reactive dyestuffs |
| EP0173476A3 (en) * | 1984-08-24 | 1988-07-20 | Imperial Chemical Industries Plc | Water-soluble dye |
| EP0596323A3 (en) * | 1992-11-02 | 1994-06-15 | Bayer Ag | Mixture of reactive phthalocyanine dyes |
| US5356444A (en) * | 1992-11-02 | 1994-10-18 | Bayer Aktiengesellschaft | Phthalocyanine reactive dyestuff mixture |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |