GB1285466A - Phthalocyanine dyestuffs and process for preparing them - Google Patents
Phthalocyanine dyestuffs and process for preparing themInfo
- Publication number
- GB1285466A GB1285466A GB4115169A GB4115169A GB1285466A GB 1285466 A GB1285466 A GB 1285466A GB 4115169 A GB4115169 A GB 4115169A GB 4115169 A GB4115169 A GB 4115169A GB 1285466 A GB1285466 A GB 1285466A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phthalocyanine
- dyestuffs
- optionally
- aug
- amine
- 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
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000001412 amines Chemical class 0.000 abstract 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 abstract 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 abstract 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 abstract 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 2
- -1 phthalocyanine radical Chemical class 0.000 abstract 2
- 239000004952 Polyamide Substances 0.000 abstract 1
- 241000083869 Polyommatus dorylas Species 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 239000011230 binding agent Substances 0.000 abstract 1
- 229920002678 cellulose Polymers 0.000 abstract 1
- 239000001913 cellulose Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-N diphosphoric acid Chemical compound OP(O)(=O)OP(O)(O)=O XPPKVPWEQAFLFU-UHFFFAOYSA-N 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 150000002466 imines Chemical group 0.000 abstract 1
- 239000003701 inert diluent Substances 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 239000010985 leather Substances 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 abstract 1
- 229910052759 nickel Inorganic materials 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 abstract 1
- 230000000865 phosphorylative effect Effects 0.000 abstract 1
- 229920002647 polyamide Polymers 0.000 abstract 1
- 229920000137 polyphosphoric acid Polymers 0.000 abstract 1
- 229940005657 pyrophosphoric acid Drugs 0.000 abstract 1
- 239000004627 regenerated cellulose Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- YXZRCLVVNRLPTP-UHFFFAOYSA-J turquoise blue Chemical compound [Na+].[Na+].[Na+].[Na+].[Cu+2].NC1=NC(Cl)=NC(NC=2C=C(NS(=O)(=O)C3=CC=4C(=C5NC=4NC=4[N-]C(=C6C=CC(=CC6=4)S([O-])(=O)=O)NC=4NC(=C6C=C(C=CC6=4)S([O-])(=O)=O)NC=4[N-]C(=C6C=CC(=CC6=4)S([O-])(=O)=O)N5)C=C3)C(=CC=2)S([O-])(=O)=O)=N1 YXZRCLVVNRLPTP-UHFFFAOYSA-J 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
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
- C09B62/443—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring the reactive group being alternatively specified
- C09B62/457—Porphines; Azaporphines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Abstract
1285466 Water-soluble phthalocyanine dyestuffs FARBWERKE HOECHST AG 18 Aug 1969 [16 Aug 1968] 41151/69 Heading C4P The invention comprises water-soluble phthalocyanine dyestuffs of the general formula wherein Pc is a phthalocyanine radical, optionally metal containing, e.g. copper or nickel, which may contain further substituents, R 3 is H or C 1 -C 4 alkyl, B is a bivalent organic bridging member, X is -CH 2 - or -N(CH 3 )-, R 1 and R 2 are each H or alkyl or aryl groups that may be substituted or together with the nitrogen atom may form an alkylene imine ring which may contain additional heteroatoms, A is a phenylene or naphthalene radical which may be substituted, n and m are 0 or 1, a, b and c are integers from 1 to 4 and a+b+c is at most 6. They are prepared by reacting (a) a compound of the formula (HO 3 S) p -Pc-(SO 2 Cl) q wherein Pc is as above, p is an integer from 0 to 3 and q is an integer from 1 to 4 with an amine wherein A, B, R 3 , X, m and n are as above optionally in presence of an amine HN(R 1 )R 2 wherein R 1 and R 2 are as above in aqueous, aqueous-organic or organic media at pH 4 to 11 at 0‹ to 100‹ C. in presence of an acid binding agent or by (b) phosphorylating the corresponding #-hydroxyethyl sulphone phthalocyanine compound e.g. using pyrophosphoric acid, polyphosphoric acid or phosphorus oxychloride optionally in presence of an inert solvent or diluent. The preferred starting materials in method (a) are phosphorylated #-hydroxyethyl- (aminophenyl)-sulphones, and amines HN(R 1 )R 2 include ammonia, methylamine, ethylamine, benzylamine, aniline and ethanolamine. The dyestuffs give green, blue and turquoise blue shades on wool, silk, linear polyamides, leather, natural cellulose e.g. linen and regenerated cellulose.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19681795140 DE1795140C3 (en) | 1968-08-16 | 1968-08-16 | Water-soluble phthalocyanine dyes, processes for their production and their use for dyeing or printing fiber materials made from native or regenerated cellulose, wool, silk, linear polyamides and leather |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1285466A true GB1285466A (en) | 1972-08-16 |
Family
ID=5708071
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4115169A Expired GB1285466A (en) | 1968-08-16 | 1969-08-18 | Phthalocyanine dyestuffs and process for preparing them |
Country Status (7)
| Country | Link |
|---|---|
| AT (1) | AT287144B (en) |
| BE (1) | BE737593A (en) |
| CA (1) | CA918657A (en) |
| CH (1) | CH551478A (en) |
| DE (1) | DE1795140C3 (en) |
| FR (1) | FR2015822A1 (en) |
| GB (1) | GB1285466A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2745481C2 (en) * | 1977-10-10 | 1979-12-20 | Hoechst Ag, 6000 Frankfurt | Water-soluble phthalocyanine compounds, process for their preparation, their use as dyes for cellulose, polyamide fibers and leather |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE965902C (en) * | 1949-07-19 | 1957-09-19 | Hoechst Ag | Process for fixing water-soluble organic compounds on substrates with a fibrous structure |
| NL261956A (en) * | 1960-03-05 | |||
| DE1265698C2 (en) * | 1961-05-06 | 1968-11-07 | Hoechst Ag | Process for the production of wetfast colorations and prints |
| FR1441328A (en) * | 1964-07-29 | 1966-06-03 | Hoechst Ag | New dyes of the azophthalocyanine series and their preparation |
| DE1283997B (en) * | 1965-01-02 | 1968-11-28 | Hoechst Ag | Process for the preparation of water-soluble phthalocyanine dyes |
| FR1483639A (en) * | 1965-06-18 | 1967-06-02 | Hoechst Ag | Water-soluble disazo dyes and their preparation |
| DE1544526C3 (en) * | 1965-06-18 | 1975-08-14 | Hoechst Ag, 6000 Frankfurt | Water-soluble disazo dyes, their metal complex compounds, process for their preparation and their use |
| FR1485299A (en) * | 1965-07-01 | 1967-06-16 | Sumitomo Chemical Co | Dyes from the phthalocyanine family; their manufacturing process, and process for dyeing fibrous products with these dyes |
| CH482801A (en) * | 1966-07-06 | 1969-12-15 | Ciba Geigy | Process for the production of new phthalocyanine dyes |
| FR1580134A (en) * | 1966-12-10 | 1969-09-05 | ||
| CH481190A (en) * | 1967-02-17 | 1969-11-15 | Geigy Ag J R | Process for the production of reactive formazan dyes containing heavy metals |
-
1968
- 1968-08-16 DE DE19681795140 patent/DE1795140C3/en not_active Expired
-
1969
- 1969-08-14 AT AT784669A patent/AT287144B/en not_active IP Right Cessation
- 1969-08-14 CH CH1238269A patent/CH551478A/en not_active IP Right Cessation
- 1969-08-15 CA CA059618A patent/CA918657A/en not_active Expired
- 1969-08-18 FR FR6928226A patent/FR2015822A1/fr active Pending
- 1969-08-18 BE BE737593D patent/BE737593A/xx unknown
- 1969-08-18 GB GB4115169A patent/GB1285466A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE1795140A1 (en) | 1972-03-02 |
| BE737593A (en) | 1970-02-18 |
| AT287144B (en) | 1971-01-11 |
| DE1795140B2 (en) | 1980-12-18 |
| FR2015822A1 (en) | 1970-04-30 |
| DE1795140C3 (en) | 1981-12-10 |
| CA918657A (en) | 1973-01-09 |
| CH551478A (en) | 1974-07-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PE20 | Patent expired after termination of 20 years |