Squarylium compounds, and processes and intermediates for the synthesis of these compounds

US6482950B1 · kind B1 · utility

Assignee

• Polaroid Corporation · US

Inventors

• Paulina P. Garcia · Arlington, US
• John Lee · Still River, US
• John Marshall · Somerville, US
• Donald A. McGowan · Bedford, US
• Anthony J. Puttick · Arlington, US
• Thomas K. Spencer · Burrton, US
• Stephen G. Stroud · Medford, US
• Stephen J. Telfer · Arlington, US
• Michael J. Zuraw · Arlington, US

Key dates

• Filing date: Jun 6, 1995
• Grant date: Nov 19, 2002
• Expiry date: Jun 6, 2015

Classification

• Technology area (CPC G): Physics
• CPC primary: G11B7/246
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

Squarylium compounds of the formula: wherein Q1 and Q2 are each independently a pyrylium, thiopyrylium, selenopyrylium, benzpyrylium, benzthiopyrylium or benzselenopyrylium nucleus, and R1 and R2 are each independently an aliphatic or cycloaliphatic group, can be prepared by reacting a squaric acid derivative of the formula: with a compound of the formula Q2CH2R2 in the presence of a base. The derivatives of Formula II may be prepared by condensing a 2,3,4,4-tetrahalocyclobut-2-en-1-one with a compound of the formula Q1CH2R1 in the presence of a base to produce a compound of the formula: wherein Q1 and R1 are as defined above, and X represents chlorine or bromine, and hydrolyzing the compound of Formula III. Alternatively, the derivatives of Formula II may be prepared by reacting a diester, monoacid chloride monoester or diacid chloride of squaric acid with a compound of the formula Q1CH2R1 in the presence of a base, followed by hydrolysis of the resultant monoacid chloride or monoester derivative of the compound of Formula II to the parent compound.