GB717137A - New phthalocyanine dyestuffs - Google Patents
New phthalocyanine dyestuffsInfo
- Publication number
- GB717137A GB717137A GB26833/51A GB2683351A GB717137A GB 717137 A GB717137 A GB 717137A GB 26833/51 A GB26833/51 A GB 26833/51A GB 2683351 A GB2683351 A GB 2683351A GB 717137 A GB717137 A GB 717137A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phthalocyanine
- methyl
- phthalimide
- heated
- sulphuric acid
- 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 3
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 3
- -1 phthalocyanine methyl phthalamic acids Chemical class 0.000 abstract 3
- 235000011149 sulphuric acid Nutrition 0.000 abstract 3
- 239000001117 sulphuric acid Substances 0.000 abstract 3
- ZZWSGBAZZZEAQQ-UHFFFAOYSA-N 7a-chloro-2-methyl-3aH-isoindole-1,3-dione Chemical compound ClC12C(C(=O)N(C1=O)C)C=CC=C2 ZZWSGBAZZZEAQQ-UHFFFAOYSA-N 0.000 abstract 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 abstract 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 abstract 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 239000000975 dye Substances 0.000 abstract 2
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 abstract 2
- 230000007062 hydrolysis Effects 0.000 abstract 2
- 238000006460 hydrolysis reaction Methods 0.000 abstract 2
- PRILUMSJUOXABT-UHFFFAOYSA-N (2-methyl-1,3-dioxoisoindol-4-yl) acetate Chemical compound C(C)(=O)OC1=C2C(C(=O)N(C2=O)C)=CC=C1 PRILUMSJUOXABT-UHFFFAOYSA-N 0.000 abstract 1
- WIYARXPRJIBMQA-UHFFFAOYSA-N 7a-hydroxy-2-methyl-3aH-isoindole-1,3-dione Chemical compound OC12C(C(=O)N(C1=O)C)C=CC=C2 WIYARXPRJIBMQA-UHFFFAOYSA-N 0.000 abstract 1
- RISUMPVKPHEEJG-UHFFFAOYSA-N C1=CC=CC=C1[Cu](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 Chemical compound C1=CC=CC=C1[Cu](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 RISUMPVKPHEEJG-UHFFFAOYSA-N 0.000 abstract 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract 1
- 229920000742 Cotton Polymers 0.000 abstract 1
- 239000004411 aluminium Substances 0.000 abstract 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 abstract 1
- 229910052782 aluminium Inorganic materials 0.000 abstract 1
- 239000010941 cobalt Substances 0.000 abstract 1
- 229910017052 cobalt Inorganic materials 0.000 abstract 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000010949 copper Substances 0.000 abstract 1
- 229910052802 copper Inorganic materials 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 1
- 229910052742 iron Inorganic materials 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000011707 mineral Substances 0.000 abstract 1
- 229910052759 nickel Inorganic materials 0.000 abstract 1
- 239000001007 phthalocyanine dye Substances 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 238000006467 substitution reaction Methods 0.000 abstract 1
- 229920002994 synthetic fiber Polymers 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
- 210000002268 wool Anatomy 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
- C09B47/12—Obtaining compounds having alkyl radicals, or alkyl radicals substituted by hetero atoms, bound to the phthalocyanine skeleton
- C09B47/16—Obtaining compounds having alkyl radicals, or alkyl radicals substituted by hetero atoms, bound to the phthalocyanine skeleton having alkyl radicals substituted by nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
The invention comprises water soluble phthalocyanine dyes of the formula: Pc -(CH2 NH2 HX)n in which Pc is a phthalocyanine residue, X is halogen, and n is an integer from 1 to 8, and also a process of producing these and similar dyes by condensing a phthalocyanine with o -hydroxy-N-methyl-phthalimide or a functional derivative thereof in presence of a concentrated mineral acid such as sulphuric acid, or a solution of aluminium chloride in tertiary amine at 30 DEG -160 DEG C. and hydrolysing the product. Hydrolysis in an alkaline medium produces phthalocyanine methyl phthalamic acids which give the above products on further hydrolysis in hydrohalic acid medium. Phthalocyanines specified are the copper, cobalt, nickel, iron, aluminium and metal-free compounds and substituted phthalocyanines such as the tetraphenyl body (in this case substitution is effected in the external nuclei). The products dye cotton, wool, and synthetic fibres. In examples, (1) copper phthalocyanine is heated with o -chloro-N-methyl-phthalimide in aluminium chloride and piperidine or in fuming sulphuric acid; (2) tetraphenyl copper phthalocyanine is heated with o -chloro-N-methyl-phthalimide in aluminium chloride and pyridine or in sulphuric acid; (3) copper phthalocyanine is heated with o -hydroxy-, methoxy-, or acetoxy-N-methylphthalimide or with diphthalimide-o -o 1-dimethyl ether.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE717137X | 1950-11-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB717137A true GB717137A (en) | 1954-10-20 |
Family
ID=6626617
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB26833/51A Expired GB717137A (en) | 1950-11-15 | 1951-11-15 | New phthalocyanine dyestuffs |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB717137A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2360638A1 (en) * | 1976-08-06 | 1978-03-03 | Sterling Drug Inc | PHTHALOCYANINE SALTS AND THEIR STABILIZED SOLUTIONS, USEFUL AS COLORS |
| EP0064631A3 (en) * | 1981-05-07 | 1984-02-22 | Basf Aktiengesellschaft | Cationic dyes, their use in dyeing or printing paper and paper dyed or printed with these dyes |
| DE3641891A1 (en) * | 1985-12-10 | 1987-06-11 | Dainippon Ink & Chemicals | METHOD FOR PRODUCING DIMETHYLAMINOMETHYL COPPER PHTHALOCYANINE AND / OR ITS DERIVATIVES |
| US5250111A (en) * | 1991-04-11 | 1993-10-05 | Ciba-Geigy Corporation | Pigment compositions |
-
1951
- 1951-11-15 GB GB26833/51A patent/GB717137A/en not_active Expired
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2360638A1 (en) * | 1976-08-06 | 1978-03-03 | Sterling Drug Inc | PHTHALOCYANINE SALTS AND THEIR STABILIZED SOLUTIONS, USEFUL AS COLORS |
| EP0064631A3 (en) * | 1981-05-07 | 1984-02-22 | Basf Aktiengesellschaft | Cationic dyes, their use in dyeing or printing paper and paper dyed or printed with these dyes |
| US4491662A (en) * | 1981-05-07 | 1985-01-01 | Basf Aktiengesellschaft | Aminomethyl group containing cationic dyes |
| DE3641891A1 (en) * | 1985-12-10 | 1987-06-11 | Dainippon Ink & Chemicals | METHOD FOR PRODUCING DIMETHYLAMINOMETHYL COPPER PHTHALOCYANINE AND / OR ITS DERIVATIVES |
| DE3641891C2 (en) * | 1985-12-10 | 1999-01-14 | Dainippon Ink & Chemicals | Process for the preparation of dimethylaminomethyl copper phthalocyanine and / or its derivatives |
| US5250111A (en) * | 1991-04-11 | 1993-10-05 | Ciba-Geigy Corporation | Pigment compositions |
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