Benzpyrylium squarylium and croconylium dyes, and processes for their preparation and use

US5405976A · kind A · utility

Assignee

• Polaroid Corporation · US

Inventors

• Stephen J. Telfer · Arlington, US
• Robert P. Short · Arlington, US
• Stephen G. Stroud · Medford, US
• Anthony J. Puttick · Arlington, US
• Socorro M. Ramos · Belmont, US
• Michael J. Zuraw · Arlington, US

Key dates

• Filing date: Sep 24, 1993
• Grant date: Apr 11, 1995
• Expiry date: Sep 24, 2013

Classification

• Technology area (CPC Y): Emerging Cross-Sectional Technologies
• CPC primary: Y10S430/145
• WIPO field: Textile and paper machines
• WIPO sector: Mechanical engineering

Abstract

Dyes comprising an inner salt of a compound of the formula: EQU Q.sup.1 =Z-Q.sup.2 wherein: PA1 Q.sup.1 is a 4-(benz[b]-4H-pyrylium)methylidene, 4-(benz[b]-4H-thiopyrylium)methylidene or 4-(benz[b]-4H-selenopyrylium)methylidene grouping; PA1 Z is a 1,3-(2-hydroxy-4-oxo-2-cyclobutylidene) hydroxide or 1,3-(2-hydroxy-4,5-dioxo-2-cyclopentylidene) hydroxide ring; and PA1 Q.sup.2 is a 4-(benz[b]-4H-pyran-4-ylidene)methyl, 4-(benz[b]-4H-thiopyran-4-ylidene)methyl or 4-(benz[b]-4H-selenopyran-4-ylidene)methyl grouping; PA1 wherein at least one of the groupings Q.sup.1 and Q.sup.2 carries at its 2-position a substituent in which a non-aromatic carbon atom is bonded directly to the benzpyrylium, benzthiopyrylium or benzselenopyrylium nucleus, subject to the proviso that if this 2-substituent contains an aromatic nucleus, this aromatic nucleus is not conjugated with the benzpyrylium, benzthiopyrylium or benzselenopyrylium nucleus to which it is attached, are useful as visible and near infra-red absorbers, having high extinction coefficients and improved solubility in polymeric media.