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EP0282182A2 Expired / Lapsed EP ⏱️ 0.0 years remaining

Substituted Phthalocyanine

Assignee: Syngenta Ltd
•
Filing: 1988-02-17
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Granted: —
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Expires: 2008-02-17
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Abstract

Abstract A phthalocyanine compound of the formula: (R-X-) m Pc (-Y-R¹-Z-) n (-SO₃M) p I wherein Pc is a phthalocyanine nucleus (Pc); each R independently is a monovalent aromatic radical linked to a peripheral carbon atom of the Pc nucleus through X; X selected from S, Se and Te; m is 4 to 16; each R¹ independently is a divalent aromatic radical linked to two adjacent peripheral carbon atoms of the Pc nucleus through Y and Z; Y is selected from S, NT, Se and Te; Z is selected from S, Se, Te, NT and 0; T is selected from H, alkyl and aryl; n is 0 to 7; M is H, a metal or optionally-substituted ammonium; and p is from 1 to 16. The compounds have a significant absorption band in the near infra red and depending on the number of sulphonic acids groups and the nature of the counter ion are soluble in aqueous and polar organic media. The compounds are useful in many applications where absorption of infra-red radiation is desirable, such as in OCR readable inks, rapid-drying inks, security printing and reprographic toners.

Inventors

  • 👤 William Marshall Institute Of Genetics Stark
  • 👤 Nigel Hughes
  • 👤 Donald Murray Gunn

Bibliographic Details

Application Number —
Jurisdiction EP
Data Source google_patents
Last Synchronized 2026-11-05 14:40
CPC Classifications
C; C07; C07D; C07D487/00; C07D487/22; C09; C09D; C09D11/00; C09D11/02; C09D11/03; C09D11/037; C09B; C09B47/00; C09B47/04; C09B47/045; C09B47/08; C09B47/20; C09B47/24; G; G03; G03G; G03G9/00; G03G9/08; G03G9/09; G03G9/0906; G03G9/0918

Claims Analysis

Total Claims: 11
Claim 1
Independent Claim 123 words
A phthalocyanine compound of the formula: (R-X-) m Pc (-Y-R¹-Z-) n (-SO₃M) p I wherein Pc is a phthalocyanine nucleus (Pc); each R independently is a monovalent aromatic radical linked to a peripheral carbon atom of the Pc nucleus through X; X selected from S, Se and Te; m is 4 to 16; each R¹ independently is a divalent aromatic radical linked to two adjacent peripheral carbon atoms of the Pc nucleus through Y and Z; Y is selected from S, NT, Se and Te; Z is selected from S, Se, Te, NT and 0; T is selected from H, alkyl and aryl; n is 0 to 7; M is H, a metal or optionally-substituted ammonium; and p is from 1 to 16.
Claim 2
Dependent Claim 123 words
A phthalocyanine compound of the formula: (R-X-) m Pc (-Y-R¹-Z-) n (-SO₃M) p I wherein Pc is a phthalocyanine nucleus (Pc); each R independently is a monovalent aromatic radical linked to a peripheral carbon atom of the Pc nucleus through X; X selected from S, Se and Te; m is 4 to 16; each R¹ independently is a divalent aromatic radical linked to two adjacent peripheral carbon atoms of the Pc nucleus through Y and Z; Y is selected from S, NT, Se and Te; Z is selected from S, Se, Te, NT and 0; T is selected from H, alkyl and aryl; n is 0 to 7; M is H, a metal or optionally-substituted ammonium; and p is from 1 to 16.
Claim 3
Dependent Claim 11 words
A compound according to Claim 1 in which Pc is Cu(II)Pc.
Claim 4
Dependent Claim 58 words
A compound according to Claim 1 wherein R is selected from phenyl, naphthyl, thienyl, furyl, pyrryl, thiazolyl, isothiazolyl, quinolyl, indolyl, pyridyl, benzoimidazolyl and benzothiazolyl, each of which is unsubstituted or is substituted by up to 3 substituents selected from C₁₋₂₀-alkyl, O-C₁₋₂₀-alkoxy, S-C₁₋₂₀-alkyl, aryl S-aryl, halogen, nitro, cyano, dialkyl-, N-alkyl-N-aryl- and diaryl­amino, -COOH, acyl and acylamino, SO₂T¹ and SO₂NT¹T².
Claim 5
Dependent Claim 49 words
A compound according to Claim 1 wherein R¹ is selected from phenylene or naphthylene each of which is unsubstituted or is substituted by up to 3 substituents selected from C₁₋₂₀-alkyl, 0-C₁₋₂₀-alkoxy, S-C₁₋₂₀-alkyl, aryl S-aryl, halogen, nitro, cyano, dialkyl-, N-alkyl-N-aryl- and diaryl- amino, -COOH, acyl and acylamino, SO₂T¹ and SO₂NT¹T².
Claim 6
Dependent Claim 13 words
A compound according to Claim 1 wherein Y is S, Se or Te.
Claim 7
Dependent Claim 50 words
A compound according to Claim 1 or Claim 5 wherein the substituted ammonium group is of the formula, NQ₄, in which at least one Q is a fatty aliphatic group or two Qs, together with the N atom, form an heteroalicyclic or heteroaromatic group selected from pyridino, piperidino and morpholino.
Claim 8
Dependent Claim 16 words
A compound according to Claim 7 wherein the fatty aliphatic group represented by Q is C₆₋₂₀-alkyl.
Claim 9
Dependent Claim 41 words
A compound according to Claim 7 wherein Q is selected from 3,5,5-trimethylhexyl, 2-ethylhexyl, 1,1,3,3-tetramethylbutyl, 1,2,2-trimethylpropyl, 2-ethylbutyl, 1-propylbutyl, 1,2-dimethyl­butyl, 2-methylpentyl, 1-ethylpentyl, 1,4-dimethylpentyl, 1-ethyl-­3-methylpentyl, hexyl, 1-methylhexyl, 3-methylhexyl, 1,3,3-trimethyl­butyl, 1,5-dimethyl- hexyl, heptyl, 1-methylheptyl, 1,4-dimethyl­heptyl, octyl, nonyl, 1-methylnonyl, decyl, dodecyl, tridecyl, pentadecyl, hexadecyl and octadecyl.
Claim 10
Dependent Claim 18 words
A compound according to Claim 6 wherein one Q is C₈₋₉-alkyl and the other three Qs are H.
Claim 11
Dependent Claim 65 words
A compound according to Claim 1 wherein Pc is Cu(II)Pc; R is phenyl, C₁₋₄-alkylphenyl or C₁₋₄-alkoxyphenyl; X is S;       m is 8 to 16; R¹ is phen-1,2-ylene, naphth-1,2-ylene or naphth-2,3-ylene; Y is S;       n is 0 to 4; Z is NT, S or 0       T is H or C₁₋₄-alkyl M is selected from H, alkali metal, NH₄, NH₃Q and diarylguanidinium; and Q is a C₈₋₉-alkyl.

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