Radiation-senstive, ethylenically unsaturated, copolymerizable compounds and their preparation

• US 5,248,805 A
• Filed: 03/02/1992
• Issued: 09/28/1993
• Est. Priority Date: 12/31/1988
• Status: Expired due to Fees

• Current Assignee: BASF AG (BASF SE)
• Original Assignee: BASF AG (BASF SE)
• Inventors: Boettcher, Andreas, Rehmer, Gerd
• Primary Examiner(s): McCamish, Marion E.
• Assistant Examiner(s): Koeckert, Arthur H.
• Application Number:
  US07/841,767
• Time in Patent Office: 575 Days
• Field of Search: 558/267, 558/268, 558/269, 558/270, 558/271, 522/46, 522/904, 522/905
• US Class Current: 558/270
• CPC Class Codes: C08G 65/331 containing oxygen cyclic ether compounds C08G65/26
• CPC Class Codes: G03F 7/027 Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds G03F7/075 takes precedence
• CPC Class Codes: Y10S 522/904 Monomer or polymer contains initiating group
• CPC Class Codes: Y10S 522/905 Benzophenone group

Abstract

Radiation-sensitive, ethylenically unsaturated compounds and a process for their preparation. The ethylenically unsaturated organic compounds are of the general formula ##STR1## where R is alkyl, aryl or a radical R¹ and

R¹ is a radical ##STR2## where R² to R⁶ are each H, alkyl, OH, OAlkyl, SH, SAlkyl, halogen, N (Alkyl)₂ or N (Alkyl) (Aryl) and at least one but not more than three of the radicals R² to R⁶ is or are a radical ##STR3## where X is alkylene, cycloalkylene, oxaalkylene or arylene, Y is H or CH₃ -- and Z is O or NY.

The novel radiation-sensitive ethylenically unsaturated compounds are suitable for the preparation of polymeric radiation-sensitive compounds.

Claims

1. An ethylenically unsaturated copolymerizable, radiation-sensitive organic compound of the formula (I) ##STR79## where R is aryl or a radical R¹ and

R¹ is a radical ##STR80## where R² and R⁶ are identical or different and each of the radicals can be H or one of the radicals ##STR81## R³ to R⁵ are identical or different and each is H, alkyl of 1 to 4 carbon atoms, phenyl, OCH₃, OC₂ H₅, F, Cl, Br, CN, COOAlkyl where alkyl is 1 to 17 carbon atoms, COOAryl, CF₃, N(Alkyl)₂, N(Alkyl)-(Aryl), N(Aryl)₂, N.sup.⊖

(Alkyl)₃ A.sup.⊖

or N.sup.⊕

H(Alkyl)₂ A.sup.⊖

where alkyl is of 1 to 4 carbon atoms, and A.sup.⊖

is the anion of an acid, and one of the radicals ##STR82## where at least one of the radicals R² to R⁶ is a radical ##STR83## where X is a divalent, unsubstituted or substituted alkylene radical--(CH₂)_m --or ##STR84## where m is from 1 to 10 and R'"'"' and R" are identical of different and each is H or alkyl, an oxaalkylene radical --(CH₂)_n --O--(CH₂)_p -- where n and p are each from 1 to 5, or a polyoxaalkylene radical having 2 to 20 oxygen atoms which are bonded to one another via at least one --CH₂ -- or --CH₂ -- CH(CH₃)--group, or a radical --(CH₂)_m --O--CO--O--(CH₂)_n --, --CH₂)_n --NH--CO--O--(CH₂)_m --, --(CH₂)_m --CO--O--(CH₂)_n or --(CH₂)_m --O--CO--(CH₂)_n -- where m and n are each from 1 to 10, an unsubstituted or substituted cycloalkylene radical of 5 to 10 carbon atoms, a (bis)methylenecycloalkylene radical of 6 to 12 carbon atoms or an unsubstituted or substituted o-, m- or p-phenylene radical,

Y is H, alkyl of 1 to 6 carbon atoms or phenyl and

Z is O.

2. The compound of the formula ##STR85##