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Monolayer-forming substituted phthalocyanine compounds and method of preparation thereof

Assignee: United States Department of the Navy
•
Filing: 1985-08-21
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Granted: 1988-06-07
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Expires: 2005-08-21
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Abstract

Abstract The invention relates to phthalocyanine compounds, and more particularly to the preparation of aryloxy, arylthio, alkyloxy, and alkylthio phthalocyanine compounds and their subsequent incorporation into semiconducting thin films by the Langmuir-Blodgett technique.

Inventors

  • 👤 William R. Barger
  • 👤 Neldon L. Jarvis
  • 👤 Arthur W. Snow
  • 👤 Henry Wohltjen

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-08 09:02
CPC Classifications
C; C09; C09B; C09B47/00; C09B47/04; C09B47/06; C09B47/067; C09B47/0675; H; H10; H10K; H10K85/00; H10K85/30; H10K85/311

Claims Analysis

Total Claims: 33
Claim 1
Independent Claim 6 words
The compound Metal-Free Tetrakis (cumylphenoxy) phthalocyanine.
Claim 2
Dependent Claim 6 words
The compound Metal-Free Tetrakis (cumylphenoxy) phthalocyanine.
Claim 3
Dependent Claim 6 words
The compound Tetrakis (cumylphenoxy) phthalocyanine copper.
Claim 4
Dependent Claim 6 words
The compound Tetrakis (cumylphenoxy) phthalocyanine copper.
Claim 5
Dependent Claim 6 words
The compound Tetrakis (cumylphenoxy) phthalocyanine nickel.
Claim 6
Dependent Claim 6 words
The compound Tetrakis (cumylphenoxy) phthalocyanine nickel.
Claim 7
Dependent Claim 6 words
The compound Tetrakis (cumylphenoxy) phthalocyanine palladium.
Claim 8
Dependent Claim 6 words
The compound Tetrakis (cumylphenoxy) phthalocyanine palladium.
Claim 9
Dependent Claim 6 words
The compound Tetrakis (cumylphenoxy) phthalocyanine platinum.
Claim 10
Dependent Claim 6 words
The compound Tetrakis (cumylphenoxy) phthalocyanine platinum.
Claim 11
Dependent Claim 6 words
The compound Tetrakis (cumylphenoxy) phthalocyanine magnesium.
Claim 12
Dependent Claim 6 words
The compound Tetrakis (cumylphenoxy) phthalocyanine magnesium.
Claim 13
Dependent Claim 6 words
The compound Tetrakis (cumylphenoxy) phthalocyanine cobalt.
Claim 14
Dependent Claim 6 words
The compound Tetrakis (cumylphenoxy) phthalocyanine cobalt.
Claim 15
Dependent Claim 6 words
The compound Tetrakis (cumylphenoxy) phthalocyanine Zinc.
Claim 16
Dependent Claim 6 words
The compound Tetrakis (cumylphenoxy) phthalocyanine Zinc.
Claim 17
Dependent Claim 6 words
The compound Tetrakis (cumylphenoxy) phthalocyanine lead.
Claim 18
Dependent Claim 6 words
The compound Tetrakis (cumylphenoxy) phthalocyanine lead.
Claim 19
Dependent Claim 6 words
The compound Tetrakis (cumylphenoxy) phthalocyanine bismuth.
Claim 20
Dependent Claim 6 words
The compound Tetrakis (cumylphenoxy) phthalocyanine bismuth.
Claim 21
Dependent Claim 4 words
The compound Tetrathiophenoxy phthalocyanine.
Claim 22
Dependent Claim 4 words
The compound Tetrathiophenoxy phthalocyanine.
Claim 23
Dependent Claim 3 words
The compound Tetraneopentoxyphthalocyanine.
Claim 24
Dependent Claim 3 words
The compound Tetraneopentoxyphthalocyanine.
Claim 25
Dependent Claim 5 words
The compound Tetra(octadecyl) copper phthalocyanine.
Claim 26
Dependent Claim 5 words
The compound Tetra(octadecyl) copper phthalocyanine.
Claim 27
Dependent Claim 3 words
The compound monocumylphenoxyphthalocyanine.
Claim 28
Dependent Claim 3 words
The compound monocumylphenoxyphthalocyanine.
Claim 29
Independent Claim 181 words
A method for preparing a phthalocyanine of the general formula: ##STR2## wherein R 1 to R 4 are selected from the group consisting of aryloxy, arylthio, alkyloxy and alkylthio and m, n, p, q and r are equal to 0 or 1 with the sum of m, n, p, and q being equal to at least 1; M is transition metal, which comprises the steps of: forming a dimethyl sulfoxide solution of 4-nitrophthalo-nitrile and a reactant selected from the group consisting of aryl or alkylalcohol, aryl or alkyl sulfide and mixtures thereof: slowly admixing anhydrous potassium carbonate into said solution under a nitrogen atmosphere until the reaction is completed; filtering out any undissolved potassium carbonate from the reaction mixture leaving a filtrate comprising a dimethyl sulfoxide solution of an oxy or thio substituted phthalonitride or a mixture thereof; slowly adding said filtrate to rapidly stirred water, forming a suspension; neutralizing said suspension; separating said oxy or thio substituted phthalonitrile; heating said oxy or thio substituted phthalonitrile alone or with a transition metal powder or salt, thereby forming phthalocyanine; separating said phthalocyanine.
Claim 30
Independent Claim 181 words
A method for preparing a phthalocyanine of the general formula: ##STR2## wherein R 1 to R 4 are selected from the group consisting of aryloxy, arylthio, alkyloxy and alkylthio and m, n, p, q and r are equal to 0 or 1 with the sum of m, n, p, and q being equal to at least 1; M is transition metal, which comprises the steps of: forming a dimethyl sulfoxide solution of 4-nitrophthalo-nitrile and a reactant selected from the group consisting of aryl or alkylalcohol, aryl or alkyl sulfide and mixtures thereof: slowly admixing anhydrous potassium carbonate into said solution under a nitrogen atmosphere until the reaction is completed; filtering out any undissolved potassium carbonate from the reaction mixture leaving a filtrate comprising a dimethyl sulfoxide solution of an oxy or thio substituted phthalonitride or a mixture thereof; slowly adding said filtrate to rapidly stirred water, forming a suspension; neutralizing said suspension; separating said oxy or thio substituted phthalonitrile; heating said oxy or thio substituted phthalonitrile alone or with a transition metal powder or salt, thereby forming phthalocyanine; separating said phthalocyanine.
Claim 31
Dependent Claim 34 words
The method of claim 15 wherein said aryl alcohol is cumylphenol and the transition metal is selected from the group consisting of copper, nickel, cobalt, platinum, palladium, magnesium, zinc, lead, bismuth, and mixtures thereof.
Claim 32
Dependent Claim 19 words
The method of claim 16 wherein said alkyl alcohol is selected from the group consisting of neopentanol and octadecanol.
Claim 33
Dependent Claim 12 words
The method of claim 15 wherein said aryl sulfide is phenyl sulfide.

References Cited (Backward Citations)

US2290906A Cited
US2456274A Cited
DE2455675C2 Cited
US3981734A Cited
US4606859A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1991-06-07 1991-12-07 1992-06-07 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1995-06-07 1995-12-07 1996-06-07 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1999-06-07 1999-12-07 2000-06-07 $7700.00 Window Closed / Lapsed

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