Polymerizable composition comprising an oxime sulfonate as thermal curing agent

Patent metadata

Field	Value
Publication number	US-10241399-B2
Application number	US-201514937308-A
Country	US
Kind code	B2
Filing date	Nov 10, 2015
Priority date	Jan 28, 2011
Publication date	Mar 26, 2019
Grant date	Mar 26, 2019

Abstract

The present invention also relates to the use of the this composition, to novel oxime sulfonates and the use of the oxime sulfonates as thermal curing promoter.

First claim

The invention claimed is:

1. An oxime sulfonate compound of the formula IA.1,

R 1 is C 1 -C 20 -alkyl, C 2 -C 20 -alkenyl, C 2 -C 20 -alkynyl, C 3 -C 20 -cycloalkyl, heterocyclyl, C 6 -C 20 -aryl, heteroaryl, C 1 -C 20 -alkanoyl, C 3 -C 20 -cycloalkanoyl, C 2 -C 20 -alkenoyl, C 6 -C 20 -aroyl, CSNR 12 R 13 , C(O)OR 9 or CSOR 9 ,
where C 1 -C 20 -alkyl, C 2 -C 20 -alkenyl and C 2 -C 20 -alkynyl may be interrupted by one or more identical or different groups selected —O—, —S—, —N(R 6 )— and CO, and/or may carry one or more identical or different radicals R 1a ,
where C 3 -C 20 -cycloalkyl and heterocyclyl may be interrupted by one or more CO groups, and/or may carry one or more identical or different radicals R 1b ,
where C 6 -C 20 -aryl and heteroaryl may carry one or more identical or different radicals R 1c ,
where C 1 -C 20 -alkanoyl and C 2 -C 20 -alkenoyl may carry one or more identical or different radicals R 1a ,
where C 3 -C 20 -cycloalkanoyl may carry one or more identical or different radicals R 1b ,
where C 6 -C 20 -aroyl may carry one or more identical or different radicals R 1d ,
where
R 1a is selected independently of one another from F, Cl, Br, I, CN, SR 4 , OR 5 , NR 6 R 7 , COR 8 , COOR 9 , CONR 10 R 11 , C 3 -C 20 -cycloalkyl which may be interrupted by one or more CO groups, heterocyclyl which may be interrupted by one or more CO groups, heteroaryl and C 6 -C 10 -aryl where the four last-mentioned radicals may carry one or more identical or different radicals R 1aa ,
where
R 1aa is selected independently of one another from C 1 -C 12 -alkyl, C 1 -C 12 -alkyl which may be interrupted by one or more groups selected from CO, O, S, C(O)O, OC(O), C(O)S and SC(O), C 1 -C 12 -haloalkyl, C 1 -C 12 -hydroxyalkyl, C 2 -C 12 -alkenyl, F, Cl, Br, I, NO 2 , SR 4 , OR 5 , NR 6 R 7 , COR 8 , COOR 9 and CONR 10 R 11 ;

R 1b is selected independently of one another from F, Cl, Br, I, CN, SR 4 , OR 5 , NR 6 R 7 , COR 8 , COOR 9 , CONR 10 R 11 , C 1 -C 12 -alkyl, C 1 -C 12 -hydroxyalkyl, C 1 -C 12 -haloalkyl, C 2 -C 12 -alkenyl, heteroaryl and C 6 -C 10 -aryl where the two last-mentioned radicals may carry one or more identical or different radicals R 1ba , where
R 1ba has one of the meanings indicated for R 1aa ;

R 1c is selected independently of one another from C 1 -C 12 -alkyl, C 1 -C 12 -haloalkyl, C 1 -C 12 -hydroxyalkyl, C 2 -C 12 -alkenyl, F, Cl, Br, I, CN, NO 2 , SR 4 , OR 5 , NR 6 R 7 , COR 8 , COOR 9 , CONR 10 R 11 , phenyl, heteroaryl, heterocyclyl and C 3 -C 10 -cycloalkyl where the two last-mentioned radicals may be interrupted by one or two C═O groups and where phenyl, heteroaryl, heterocyclyl and C 3 -C 10 -cycloalkyl may carry one or more identical or different radicals R 1ca , where
R 1ca has one of the meanings indicated for R 1aa ;

R 1d is selected independently of one another from C 1 -C 12 -alkyl, C 1 -C 12 -haloalkyl, C 1 -C 12 -hydroxyalkyl, C 2 -C 12 -alkenyl, F, Cl, Br, I, CN, SR 4 , OR 5 , NR 6 R 7 , COR 8 , COOR 9 , CONR 10 R 11 , C 3 -C 20 -cycloalkyl which may be interrupted by one or more CO groups, heterocyclyl which may be interrupted by one or more CO groups, C 6 -C 10 -aryl and heteroaryl where the four last-mentioned radicals may carry one or more radicals R 1da , where R 1da has one of the meanings indicated for R 1aa ;

R 2 is hydrogen, SR 4 , OR 5 , NR 1 R 14 , COR 8 , SO 2 R 4 , COOR 9 , CONR 10 R 11 , SO 2 NR 10 R 11 , PO(OR 9 ) 2 , C 1 -C 16 -alkyl, C 2 -C 20 -alkenyl, C 2 -C 20 -alkynyl, C 3 -C 20 -cycloalkyl, heterocyclyl, C 6 -C 20 -aryl, heteroaryl, C 1 -C 20 -alkanoyl, C 2 -C 20 -alkenoyl, C 3 -C 20 -cycloalkanoyl, C 6 -C 20 -aroyl or a group E,
where C 1 -C 16 -alkyl, C 2 -C 20 -alkenyl and C 2 -C 20 -alkynyl may be interrupted by one or more identical or different groups selected from —O—, —S—, —N(R 6 )— and CO, and/or may carry one or more identical or different radicals R 2a ,
where C 3 -C 20 -cycloalkyl and heterocyclyl may be interrupted by one or more CO groups, and/or may carry one or more identical or different radicals R 2b ,
where C 6 -C 20 -aryl and heteroaryl may carry one or more identical or different radicals R 2c ,
where C 1 -C 20 -alkanoyl and C 2 -C 20 -alkenoyl may carry one or more identical or different radicals R 2a ,
where C 3 -C 20 -cycloalkanoyl may carry one or more identical or different radicals R 2b ,
where C 6 -C 20 -aroyl may carry one or more identical or different radicals R 2d ,
where
R 2a is selected independently of one another from F, Cl, Br, I, CN, SR 4 , OR 5 , NR 6 R 7 , COR 8 , COOR 9 , CONR 10 R 11 , C 3 -C 20 -cycloalkyl which may be interrupted by one or more CO groups, heterocyclyl which may be interrupted by one or more CO groups, heteroaryl and C 6 -C 10 -aryl where the four last-mentioned radicals may carry one or more identical or different radicals R 2aa ,
where
R 2aa is selected independently of one another from C 1 -C 12 -alkyl, C 1 -C 12 -alkyl which may be interrupted by one or more groups selected from CO, O, S, C(O)O, OC(O), C(O)S and SC(O), C 1 -C 12 -haloalkyl, C 1 -C 12 -hydroxyalkyl, C 2 -C 12 -alkenyl, phenyl, F, Cl, Br, I, CN, NO 2 , SR 4 , OR 5 , NR 6 R 7 , COR 8 , COOR 9 and CONR 10 R 11 ;

R 2b has one of the meanings indicated for R 1b ;
R 2c is selected independently of one another from C 1 -C 12 -alkyl, C 1 -C 12 -haloalkyl, C 1 -C 12 -hydroxyalkyl, C 2 -C 12 -alkenyl, F, Cl, Br, I, CN, NO 2 , SR 4 , NR 6 R 7 , COR 8 , COOR 9 , CONR 10 R 11 , phenyl, heteroaryl, heterocyclyl and C 3 -C 10 -cycloalkyl where the two last-mentioned radicals may be interrupted by one or two C═O groups and where phenyl, heteroaryl, heterocyclyl and C 3 -C 10 -cycloalkyl may carry one or more identical or different radicals R 1ca ;
R 2d has one of the meanings indicated for R 1d ;
E is selected from

where
# is the point of attachment to the remainder of the molecule;
d is 0, 1, 2, 3 or 4;
e is 0, 1, or 2;
f is 0, 1, or 2;
g is 0, 1, 2, 3 or 4;
R 2e has one of the meanings indicated for R 2e ;
R 2f is C 1 -C 20 -alkylene-COO − , C 2 -C 20 -alkenylene-COO − , C 2 -C 20 -alkynylene-COO − , C 3 -C 20 -cycloalkylene-COO − , heterocycloalkylene-COO − , C 6 -C 20 -arylene-COO − , heteroarylene-COO − , C 1 -C 20 -alkylene-S(O 2 )O − , C 2 -C 20 -alkenylene-S(O 2 )O − , C 2 -C 20 -alkynylene-S(O 2 )O − , C 3 -C 20 -cycloalkylene-S(O 2 )O − , heterocycloalkylene-S(O 2 )O − , C 6 -C 20 -arylene-S(O 2 )O − , heteroarylene-S(O 2 )O − , C 1 -C 20 -alkylene-OS(O 2 )O − , C 2 -C 20 -alkenylene-OS(O 2 )O − , C 2 -C 20 -alkynylene-OS(O 2 )O − , C 3 -C 20 -cycloalkylene-OS(O 2 )O − , heterocycloalkylene-OS(O 2 )O − , C 6 -C 20 -arylene-OS(O 2 )O − or heteroarylene-OS(O 2 )O −
where each alkylene, each alkenyle and each alkynyle may be interrupted by one or more identical or different groups selected from —O—, —S—, —N(R 6 )— and CO, and/or may carry one or more identical or different radicals R 2a ,
where each cycloalkylene and each heterocycloalkylene may be interrupted by one or two groups CO and/or may carry one or more identical or different radicals R 2b ,
where each arylene and each heteroarylene may carry one or more radicals R 2c ,

An − is Cl − , Br − , I − , SCN − , BF 4 − , PF 6 − , ClO 4 − , SbF 6 − , AsF 6 − , C 1 -C 20 -alkyl-COO − , C 1 -C 20 -alkyl-S(O) 2 O − , C 1 -C 20 -alkyl-OS(O) 2 O − , C 6 -C 20 -aryl-COO − , C 6 -C 20 -aryl-S(O) 2 O − or C 6 -C 20 -aryl-OS(O) 2 O − , where the aryl moiety of the three last-mentioned radicals may be substituted by 1, 2, 3 or 4 identical or d

Assignees

• Basf Se

Inventors

• Kunimoto Kazuhiko
• Sameshima Kaori
• Matsuoka Yuki
• Kura Hisatoshi

Classifications

• C07D277/54

  Nitrogen and either oxygen or sulfur atoms · CPC title

• G03F7/0007 Primary

  Filters, e.g. additive colour filters; Components for display devices · CPC title

• C07D309/08

  with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms · CPC title

• C07C2602/42

  the bicyclo ring system containing seven carbon atoms · CPC title

• G02B5/201

  in the form of arrays · CPC title