US 2014/0005301 A1Published application

Sulfonium sulfates, their preparation and use

AssigneeBASF SE

InventorsKazuhiko Kunimoto, Hisatoshi Kura

Life of this patent

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Abstract

The present invention relates to a heat-curable composition comprising (a) at least one compound which is capable of undergoing cationic polymerization; and (b) at least one sulfonium sulfate selected from compounds of the formulae Ia and Ib where Yn− is a monovalent or divalent anion selected from (1) where n, M, R1 to R10 are as defined in claim 1 and in the description. The present invention also relates to novel sulfonium sulfates of the formulae Ia and Ib, to a process for curing cationically polymerizable material and to the cured material obtained by said process.

Claims31

Dependent claims

A heat-curable composition, comprising:

at least one compound which is capable of undergoing cationic polymerization;
and
at least one sulfonium sulfate selected from the group consisting of compounds of the formulae (Ia) and (Ib):
wherein:
Yn− is a monovalent or divalent anion selected from
n is one or two;
R1 is C1-C20-alkyl, C3-C20-cycloalkyl, heterocycloalkyl, a group A or a group B, where C1-C20-alkyl may be substituted by one or more identical or different radicals R1a and/or may be interrupted by one or more non-adjacent groups selected from —O—, —S—, —C(O)— and —N(RN)—,
where
R1a is F, Cl, Br, I, CN, SR19, OR20, COR21, COOR22, CONR23R24, C3-C20-cycloalkyl or heterocycloalkyl, where the two last-mentioned radicals may be interrupted by one or more CO groups, and/or may carry one or more identical or different radicals R1ab,
where
R1ab is F, Cl, Br, I, C1-C12-alkyl, C1-C12-haloalkyl, CN, SR19, OR20, COR21, COOR22 or CONR23R24;
where C3-C20-cycloalkyl and heterocycloalkyl may be interrupted by one or more CO groups and/or may be substituted by one or more identical or different radicals R1b,
where
R1b is F, Cl, Br, I, C1-C12-alkyl, C1-C12-haloalkyl, CN, SR19, OR20, COR21, COOR22 or CONR23R24;
where
the group of the formula A is
in which
# is the point of attachment to the sulfonium atom, and
where
the group of the formula B is
in which
# is the point of attachment to the sulfonium atom,
with the proviso that R1 is the group A or the group B, if R2 and R3 are both selected from the group consisting of C1-C20-alkyl;
C1-C20-alkyl substituted by one or more radicals R2a;
C1-C20-alkyl which is interrupted by one or more non-adjacent groups selected from —O—, —S—, —C(O)—, and —N(RN));
C1-C20-alkyl which is interrupted by one or more non-adjacent groups selected from —O—, —S—, —C(O)—, and —N(RN)) and substituted by one or more radicals R2a;
C3-C20-cycloalkyl;
C3-C20-cycloalkyl interrupted by one or more CO groups;
C3-C20-cycloalkyl substituted by one or more radicals R2b;
and C3-C20-cycloalkyl interrupted by one or more CO groups and substituted by one or more radicals R2b;
R2 and R3 are selected independently of one another from C1-C20-alkyl, C2-C20-alkenyl, C2-C20-alkynyl, C3-C20-cycloalkyl, heterocycloalkyl, C6-C20-aryl and heteroaryl,
where C1-C20-alkyl, C2-C20-alkenyl and C2-C20-alkynyl may be substituted by one or more identical or different radicals R2a and/or may be interrupted by one or more non-adjacent groups selected from —O—, —S—, —C(O)— and —N(RN)—,
where C3-C20-cycloalkyl and heterocycloalkyl may be interrupted by one or more CO groups, and/or may carry one or more identical or different radicals R2b,
where C6-C20-aryl and heteroaryl may be substituted by one or more identical or different radicals R2c,
where
R2a is selected from F, Cl, Br, I, CN, SR10, OR20, COR21, COOR22, CONR23R24, C3-C20-cycloalkyl and heterocycloalkyl, where the two last-mentioned radicals may be interrupted by one or more CO groups and/or may be substituted by one or more identical or different radicals R2ab, and also from the group consisting of heteroaryl and C6-C10-aryl, where the two last-mentioned radicals may be substituted by one or more identical or different radicals R2ac,
where
R2ab has one of the meanings indicated for R1ab,
R2ac is F, Cl, Br, I, C1-C12-alkyl, C1-C12-haloalkyl, CN, NO2, SR19, OR20, COR21, COOR22 or CONR23R24;
R2b is F, Cl, Br, I, C1-C12-alkyl, C1-C12-haloalkyl, CN, SR19, OR20, COR21, COOR22, CONR23R24, C6-C10-aryl or heteroaryl where the two last-mentioned radicals may be substituted by one or more identical or different radicals R2bc,
where
R2bc has one of the meanings indicated for R2ac;
R2c is F, Cl, Br, I, C1-C12-alkyl, C1-C12 haloalkyl, CN, NO2, SR19, OR20, COR21, COOR22, CONR23R24, phenyl,
C3-C10-cycloalkyl or heterocycloalkyl where the two last-mentioned radicals may be interrupted by one or more CO groups;
or
R1 and R2 or R1 and R3 may together form a straight-chain C2-C6-alkylene group, a straight-chain C2-C6-alkenylene group, or a —(CH2)a—C6H4—(CH2)b group, where a and b are an integer from 0 to 10 and the sum of a and b is 1 to 10, where alkylene, alkenylene and the alkylene moiety of —(CH2)a—C6H4—(CH2)b may be substituted by one or more identical or different radicals R32 and/or may be interrupted by one or more non-adjacent groups selected from —O—, —S—, —C(O)— and —N(RN)—;
or
R2 and R3 may together form a straight-chain C2-C6-alkylene, a straight-chain C2-C6-alkenylene, or a straight-chain —(CH2)c—C6H4—(CH2)d group, where c and d are an integer from 0 to 10 and the sum of c and d is 1 to 10, where alkylene, alkenylene and the alkylene moiety of —(CH2)c—C6H4—(CH2)d may be substituted by one or more identical or different radicals R32 and/or may be fused to 1 or 2 phenyl rings and/or may be interrupted by one or more non-adjacent groups selected from —O—, —S—, —C(O)— and —N(RN)—;
R4 is C1-C20-alkyl, C2-C20-alkenyl, C2-C20-alkynyl, C3-C20-cycloalkyl, heterocycloalkyl, C6-C20-aryl, heteroaryl, —NR11R12 or —N═CR13R14,
where C1-C20-alkyl, C2-C20-alkenyl and C2-C20-alkynyl may be substituted by one or more identical or different radicals R4a and/or may be interrupted by one or more non-adjacent groups selected from —O—, —S—, —C(O)— and —N(RN)—,
where C3-C20-cycloalkyl and heterocycloalkyl may be interrupted by one or more CO groups and/or may be substituted by one or more identical or different radicals R4b, and where C6-C20-aryl and heteroaryl may be substituted by one or more identical or different radicals R4c,
where
R4a is selected from F, Cl, Br, I, CN, SR19, OR20, COR21, COOR22, CONR23R24, C3-C20-cycloalkyl and heterocycloalkyl where the 2 last-mentioned radicals may be interrupted by one or more CO groups and/or may be substituted by one or more identical or different radicals R4ab, and also from the group consisting of heteroaryl and C6-C10-aryl, where the two last-mentioned radicals may be substituted by one or more identical or different radicals R4ac,
where
R4ab has one of the meanings indicated for R1ab,
R4ac has one of the meanings indicated for R2ac, and
in addition, if 2 radicals R4a are geminally bound, the 2 radicals R4a together may also form an N-hydroxyimino group;
R4b is F, Cl, Br, I, C1-C12-alkyl, CN, SR19, OR20, COR21, COOR22, CONR23R24, C6-C10-aryl or heteroaryl, where the two last-mentioned radicals may be substituted by one or more identical or different radicals R4bc,
where
R4bc has one of the meanings indicated for R2bc;
R4c is F, Cl, Br, I, C1-C12-alkyl, C1-C12-haloalkyl, CN, NO2, SR19, OR20, COR21, COOR22, CONR23R24, phenyl, C3-C10-cycloalkyl or heterocycloalkyl, where two last-mentioned radicals may be interrupted by one or more CO groups;
R5, R6, R7 and R8 are selected independently of one another from C1-C20-alkyl, C2-C20-alkenyl, C2-C20-alkynyl, C3-C20-cycloalkyl, heterocycloalkyl, C6-C20-aryl and heteroaryl,
where C1-C20-alkyl, C2-C20-alkenyl and C2-C20-alkynyl may be substituted by one or more identical or different radicals R5a and/or may be interrupted by one or more non-adjacent groups selected from —O—, —S—, —C(O)— and —N(RN)—,
where C3-C20-cycloalkyl and heterocycloalkyl may be interrupted by one or more CO groups and/or may be substituted by one or more identical or different radicals R5b, where C6-C20-aryl and heteroaryl may be substituted by one or more identical or different radicals R5c, where
R5a has one of the meanings indicated for R2a,
R5b has one of the meanings indicated for R2b,
R5c has one of the meanings indicated for R2c;
or
R5 and R6 and/or R7 and R8 may together form a straight-chain C2-C6-alkylene, a straight-chain C2-C6-alkenylene or a straight-chain —(CH2)c—C6H4—(CH2)d group, where c and d are an integer from 0 to 10 and the sum of c and d is 1 to 10, where alkylene, alkenylene and the alkylene moiety of —(CH2)c—C6H4—(CH2)d may be substituted by one or more identical or different radicals R32 and/or may be fused to 1 or 2 phenyl rings and/or may be interrupted by one or more non-adjacent groups selected from —O—, —S—, —C(O)— and —N(RN)—;
R9 and R10 are independently of one another selected from C1-C20-alkyl, C2-C20-alkenyl, C2-C20-alkynyl, C3-C20-cycloalkyl, heterocycloalkyl, C6-C20-aryl, heteroaryl, —NR11R12 and —N═CR13R14, where C1-C20-alkyl, C2-C20-alkenyl and C2-C20-alkynyl may be substituted by one or more identical or different radicals R9a and/or may be interrupted by one or more non-adjacent groups selected from —O—, —S—, —C(O)— and —N(RN)—, where C3-C20-cycloalkyl and heterocycloalkyl may be interrupted by one or more CO groups and/or may be substituted by one or more identical or different radicals R9b, where C6-C20-aryl and heteroaryl may be substituted by one or more identical or different radicals R9c, where
R9a has one of the meanings indicated for R4a,
R9b has one of the meanings indicated for R4b,
R9c has one of the meanings indicated for R4c;
R11 and R12 are independently of one another selected from hydrogen, C1-C20-alkyl, C2-C20-alkenyl, C2-C20-alkynyl, C3-C20-cycloalkyl, heterocycloalkyl, C6-C20-aryl, heteroaryl, C2-C20-alkanoyl, C3-C20-alkenoyl and C6-C10-aroyl,
where C1-C20-alkyl, C2-C20-alkenyl and C2-C20-alkynyl may be substituted by one or more identical or different radicals R11a and/or may be interrupted by one or more non-adjacent groups selected from —O—, —S—, —C(O)— and —N(RN)—,
where C3-C20-cycloalkyl and heterocycloalkyl may be interrupted by one or CO groups and/or may be substituted by one or more identical or different radicals R11b,
where C6-C20-aryl and heteroaryl may be may be substituted by one or more identical or different radicals R11c,
where C2-C20-alkanoyl and C3-C20-alkenoyl may be substituted by one or more identical or different radicals R11d,
where C6-C10-aroyl may be substituted by one or more identical or different radicals R11e,
R11a has one of the meanings indicated for R2a,
R11b has one of the meanings indicated for R2b,
R11c has one of the meanings indicated for R2c,
R11d is F, Cl, Br, I, CN, NO2, SR19, OR20, COR21, COOR22 or CONR23R24;
R11e is F, Cl, Br, I, C1-C12-alkyl, C1-C12-haloalkyl, CN, NO2, SR19, OR20, COR21, COOR22 or CONR23R24;
or
R11 and R12 may together form a straight-chain C2-C5-alkylene or a straight-chain C2-C5-alkenylene chain, where alkylene and alkenylene may be substituted by one or more identical or different radicals R11f and/or may be interrupted by one or more non-adjacent groups selected from —O—, —S—, —C(O)— and —N(RN)—,
or
R11 and R12 may together form an o-phenylenedicarbonyl or 1,8-naphthalenedicarbonyl group, where the two last mentioned radicals may be substituted by one or more identical or different radicals R11f, where
R11f has one of the meanings indicated for R11e;
R13 and R14 are, independently of one another, selected from hydrogen, CN, NO2, SR19, OR20, COR21, COOR22, CONR23R24, C1-C20-alkyl, C2-C20-alkenyl, C2-C20-alkynyl, C3-C20-cycloalkyl, heterocycloalkyl, C6-C20-aroyl, C6-C20-aryl and heteroaryl,
where C1-C20-alkyl, C2-C20-alkenyl and C2-C20-alkynyl may be substituted by one or more identical or different radicals R13a and/or may be interrupted by one or more non-adjacent groups selected from —O—, —S— —C(O)— and —N(RN)—,
where
C3-C20-cycloalkyl and heterocycloalkyl may be interrupted by one or more CO groups and/or may be substituted by one or more identical or different radicals R13b,
where
C6-C20-aroyl, C6-C20-aryl and C5-C20-heteroaryl may be substituted by one or more identical or different radicals R13c,
where
R13a is selected from F, Cl, Br, I, CN, SR19, OR20, COR21, COOR22, CONR23R24, C3-C20-cycloalkyl and heterocycloalkyl where the 2 last-mentioned radicals may be interrupted by one or more CO groups and/or may be substituted by one or more identical or different radicals R13ab, and also from the group consisting of phenyl and phenyl which is substituted by one or more identical or different radicals R13ac,
where
R13ab has one of the meanings indicated for R1ab,
R13ac has one of the meanings indicated for R2ac;
R13b is F, Cl, Br, I, C1-C12-alkyl, C1-C12-haloalkyl, CN, SR19, OR20, COR21, COOR22, CONR23R24, phenyl or phenyl which is substituted by one or more identical or different radicals R13bc, where
R13bc has one of the meanings indicated for R2ac;
R13c has one of the meanings indicated for R4c;
or
R13 and R14 may together form a straight-chain C2-C6-alkylene or a straight-chain C2-C6-alkenylene chain, where alkylene and alkenylene may be substituted by one or more identical or different radicals R32 and/or may be interrupted by one or more non-adjacent groups selected from —O—, —S—, —C(O)— and —N(RN)—;
R19 and R20 are selected independently of one another from hydrogen, C1-C20-alkyl, C2-C12-alkenyl, C3-C10-cycloalkyl, heterocycloalkyl, where the two last-mentioned radicals may be interrupted by one or more CO groups, C1-C20-alkyl which is interrupted by one or more non-adjacent groups selected from —O—, —S—, —C(O)— and —N(RN)—, C1-C8-alkyl substituted by one or more identical or different radicals R19a, —(CH2CH2O)mH with m being 1-20, —(CH2CH2O)n(CO)—(C1-C8-alkyl) with n being 1-20, C2-C8-alkanoyl, C2-C8-haloalkanoyl, C3-C6-alkenoyl, benzoyl where the last-mentioned radical may be substituted by one or more radicals selected independently of one another from F, Cl, Br, I, C1-C6-alkyl, OH and C1-C4-alkoxy, phenyl, naphthyl, where the two last-mentioned radicals may be substituted by one or more identical or different radicals R19c,
or phenyl or naphthyl which forms a 5- or 6-membered ring via the phenyl ring to which SR19 or OR20, respectively, is attached via a single bond, C1-C4-alkylene, O, S, CO or NR23,
where
R19a is F, Cl, Br, I, OH, SH, CN, C3-C10-cycloalkyl, heterocycloalkyl, phenyl, C3-C6 alkenoxy, —OCH2CH2CN, —OCH2CH2(CO)O(C1-C8-alkyl), —O(CO)—(C1-C8-alkyl), —O(CO)-phenyl, —(CO)OH or —(CO)O(C1-C8-alkyl),
R19c is F, Cl, Br, I, C1-C12-alkyl, C1-C12-haloalkyl, C1-C12-alkoxy, phenyl-C1-C3-alkyloxy, phenoxy, C1-C12-alkylsulfanyl, phenylsulfanyl, —(CO)O(C1-C8-alkyl), (CO)N(C1-C8-alkyl)2 or phenyl;
R21 is selected independently of one another from hydrogen, C1-C20-alkyl, C2-C12-alkenyl, C1-C20-alkyl which is interrupted by one or more non-adjacent groups selected from —O—, —S—, —CO— and —N(RN)—, C1-C8-alkyl substituted by one or more identical or different radicals R21a, —(CH2CH2O)oH with o being 1-20, —(CH2CH2O)p(CO)—(C1-C8-alkyl) with p being 1-20, C3-C10-cycloalkyl, heterocycloalkyl, where the two last-mentioned radicals may be interrupted by one or more CO groups, C6-C20-aryl and heteroaryl, where the two last-mentioned radicals may be substituted by one or more radicals identical or different radicals R21c,
where
R21a is F, Cl, Br, I, OH, SH, CN, phenyl, C3-C6 alkenoxy, —OCH2CH2CN, —OCH2CH2(CO)O(C1-C8-alkyl), —O(CO)—(C1-C8-alkyl), —O(CO)-phenyl, —(CO)OH or —(CO)O(C1-C8-alkyl), and
R21c has one of the meanings indicated for R19c;
R22 is selected independently of one another from hydrogen, C1-C20-alkyl, C2-C12-alkenyl, C2-C20-alkyl which is interrupted by one or more non-adjacent groups selected from —O—, —S—, —C(O)— and —NRN—, C1-C8-alkyl substituted by one or more identical or different radicals R22a, —(CH2CH2O)qH with q being 1-20, —(CH2CH2O)r(CO)—(C1-C8-alkyl) with r being 1-20, C3-C10-cycloalkyl, heterocycloalkyl, where the two last-mentioned radicals may be interrupted by one or more CO groups, phenyl and naphthyl, where the two last-mentioned radicals may be substituted by one or more identical or different radicals R22c,
where
R22a is F, Cl, Br, I, OH, SH, CN, C3-C6 alkenoxy, —OCH2CH2CN, —OCH2CH2(CO)O(C1-C8-alkyl), —O(CO)—(C1-C8-alkyl), —O(CO)-phenyl, —(CO)OH, —(CO)O(C1-C8-alkyl), phenyl or naphthyl, where the two last-mentioned radicals may be substituted by one or more identical or different radicals R22ac,
where
R22ac has one of the meanings indicated for R19c;
R22c has one of the meanings indicated for R19c;
R23 and R24 are, independently of one another, selected from hydrogen, OR20, C1-C20-alkyl, C2-C12-alkenyl, C2-C20-alkyl which is interrupted by one or more non-adjacent groups selected from —O—, —S—, —C(O)— and —NRN—, C1-C8-alkyl substituted by one or more identical or different radicals R23a, —(CH2CH2O)sH with s being 1-20, —(CH2CH2O)t(CO)—(C1-C8-alkyl) with t being 1-20, C2-C8alkanoyl, C2-C8-haloalkanoyl, C3-C6-alkenoyl, benzoyl which may be substituted by one or more identical or different radicals selected from F, Cl, Br, I, C1-C6-alkyl, —OH and C1-C4-alkoxy, C3-C10-cycloalkyl, heterocycloalkyl, where the two last-mentioned radicals may be interrupted by one or more CO groups, phenyl and naphthyl, where the two last-mentioned radicals may be substituted by one or more identical or different radicals R23c,
where
R23a is F, Cl, Br, I, OH, SH, CN, phenyl, C3-C6-alkenoxy, —OCH2CH2CN, —OCH2CH2(CO)O(C1-C8-alkyl), —O(CO)—(C1-C8-alkyl), —O(CO)-phenyl, —(CO)OH or —(CO)O(C1-C8-alkyl),
R23c has one of the meanings indicated for R19c;
or
R23 and R24 together may form a C2-C5-alkylene group, which may be interrupted by one or more non-adjacent groups selected from —O—, —S—, —C(O)— and —N(RN)—;
R25 and R26 are, each independently of one another, selected from hydrogen, F, Cl, Br, CN, NO2, SR19, OR20, COR21, COOR22, CONR23R24, C1-C20-alkyl, C3-C20-cycloalkyl, heterocycloalkyl, C6-C20-aryl and heteroaryl,
where
C1-C20-alkyl may be interrupted by one or more non-adjacent groups selected from —O—, —S—, —C(O)— and —N(RN)— and/or may be substituted by one or more identical or different radicals R25a,
where
C3-C20-cycloalkyl and heterocycloalkyl may be interrupted by one or more CO groups and/or may be substituted by one or more identical or different radicals R25b, and
where
C6-C20-aryl and heteroaryl may be substituted by one or more identical or different radicals R25c,
where
R25a has one of the meanings indicated for R13a;
R25b has one of the meanings indicated for R13b;
R25c has one of the meanings indicated for R13c;
R27, R28, R29, R30 and R31 are, each independently of one another, selected from hydrogen, F, Cl, Br, I, CN, NO2, SR19, OR20, COR21, COOR22, CONR23R24, C1-C20-alkyl, C2-C20-alkenyl, C2-C20-alkynyl, C3-C20-cycloalkyl, heterocycloalkyl, C6-C20-aryl and heteroaryl,
where
C1-C20-alkyl, C2-C20-alkenyl and C2-C20-alkynyl may be substituted one or more radicals identical or different radicals R27a and/or may be interrupted by one or more non-adjacent groups selected from —O—, —S—, —C(O)— and —N(RN)—,
where
C3-C20-cycloalkyl and heterocycloalkyl may be interrupted by one or more CO groups and/or may be substituted by one or more identical or different radicals R27b,
where
C6-C20-aryl and heteroaryl may be substituted by one or more identical or different radicals R27c,
where
R27a has one of the meanings indicated for R13a;
R27b has one of the meanings indicated for R13b;
R27c has one of the meanings indicated for R13c;
or
two radicals R27 and R28, R28 and R29, R29 and R30 and/or R30 and R31 may together form a straight-chain C2-C6-alkylene or a straight-chain C2-C6-alkenylene group, where the alkylene group and the alkenylene group may be substituted by one or more identical or different radicals R32 and/or may be fused to 1 or 2 C6-C10-aryl rings and/or may be interrupted by one or more non-adjacent groups selected from —O—, —S—, —C(O)— and —N(RN)—,
or
R25 and R27 may together form a C2-C6-alkylene chain, where alkylene may be substituted by one or more radicals R32 and/or may be interrupted by one or more non-adjacent groups selected from —O—, —S—, —C(O)— and —N(RN)—,
or
R25 and R27 may together form a 1,2-phenylene group, where 1,2-phenylene may be substituted by one or more identical or different radicals R32;
R32 is F, Cl, Br, I, CN, NO2, SR19, OR20, COR21, COOR22, CONR23R24, C1-C20-alkyl, C2-C20-alkenyl, C2-C20-alkynyl, C3-C20-cycloalkyl, heterocycloalkyl, C6-C20-aryl and heteroaryl;
where
C1-C20-alkyl, C2-C20-alkenyl and C2-C20-alkynyl may be interrupted by one or more non-adjacent groups selected from —O—, —S—, —C(O)— and —N(RN)— and/or may be substituted one or more radicals identical or different R32a,
where
C3-C20-cycloalkyl and heterocycloalkyl may be interrupted by one or more CO groups and/or may be substituted by one or more identical or different radicals R32b,
where
C6-C20-aryl and heteroaryl may be substituted by one or more radicals identical or different R32c,
where
R32a has one of the meanings indicated for R13a;
R32b has one of the meanings indicated for R13b;
and
R32c has one of the meanings indicated for R13c;
R33 and R34 are, each independently of one another are selected from hydrogen, F, Cl, Br, I, CN, NO2, SR19, OR20, COR21, COOR22, CONR23R24, C1-C20-alkyl, C3-C20-cycloalkyl, heterocycloalkyl, C6-C20-aryl and heteroaryl,
where
C1-C20-alkyl may be may be substituted by one or more radicals R33a and/or may be interrupted by one or more non-adjacent groups selected from —O—, —S—, —C(O)— and —N(RN)—,
where
C3-C20-cycloalkyl and heterocycloalkyl may be interrupted by one or more CO groups and/or may be substituted by one or more identical or different radicals R33b, and
where
C6-C20-aryl and heteroaryl may be substituted by one or more identical or different radicals R33c,
where
R33a has one of the meanings indicated for R13a;
R33b has one of the meanings indicated for R13b;
R33c has one of the meanings indicated for R13c;
R35, R36 and R37, each independently of one another are selected from hydrogen, F, Cl, Br, I, CN, NO2, SR10, OR20, COR21, COOR22, CONR23R24, C1-C20-alkyl, C2-C20-alkenyl, C2-C20-alkynyl, C3-C20-cycloalkyl, heterocycloalkyl, C6-C20-aryl and heteroaryl,
where
C1-C20-alkyl, C2-C20-alkenyl and C2-C20-alkynyl may be substituted by one or more identical or different radicals R35a and/or may be interrupted by one or more non-adjacent groups selected from —O—, —S—, —C(O)— and —N(RN)—,
where
C3-C20-cycloalkyl and heterocycloalkyl may be substituted by one or more identical or different radicals R35b, and
where
C6-C20-aryl and heteroaryl may be substituted by one or more identical or different radicals R35c,
where
R35a has one of the meanings indicated for R27a;
R35b has one of the meanings indicated for R27b;
R35c has one of the meanings indicated for R17c;
or
R35 and R36 may together form a straight-chain C2-C6-alkylene or a straight-chain C2-C6-alkenylene group, where alkylene and alkenylene may be substituted by one or more radicals identical or different R32 and/or may be interrupted by one or more non-adjacent groups selected from —O—, —S—, —C(O)— and —N(RN)—,
or
two radicals R33 and R35, R33 and R37, R34 and R35 and/or R34 and R37 may together form a straight-chain C2-C6-alkylene group, where the alkylene group may be substituted by one or more identical or different radicals R32 and/or may be interrupted by one or more non-adjacent groups selected from —O—, —S—, —C(O)— and —N(RN)—;
M is a divalent radical selected from C1-C20-alkylene, C2-C20-alkenylene, C2-C20-alkynylene, C3-C20-cycloalkylene, heterocycloalkylene, C6-C20-arylene and heteroarylene, where C1-C20-alkylene, C2-C20-alkenylene and C2-C20-alkynylene may be substituted by one or more identical or different radicals RMa and/or may be interrupted by one or more identical or different non-adjacent groups RMi,
where
C3-C20-cycloalkylene and heterocycloalkylene may be interrupted by one or more CO groups and/or may be substituted by one or more radicals
RMb;
where
C6-C20-arylene and heteroarylene may be substituted by one or more radicals RMc,
where
RMi is selected from —O—, —S—, —C(O)—, OC(O)—, —N(RN)—, C3-C20-cycloalkylene, —O—C3-C20-cycloalkylene, —O—C3-C20-cycloalkylene-O—, heterocycloalkylene, C6-C20-arylene, —O—C6-C20-arylene, —O—C6-C20-arylene-O—, —S—C6-C20-arylene, —S—C6-C20-arylene-S— and heteroarylene, where each cycloalkylene and heterocycloalkylene may be interrupted by one or more CO groups and/or may be substituted by one or more identical or different radicals RMib, and
where
each arylene and heteroarylene may be substituted by one or more radicals RMic,
RMa is F, Cl, Br, I, CN, SR19, OR20, COR21, COOR22, CONR23R24, C6-C10-aryl or heteroaryl where the 2 last-mentioned radicals may be substituted by one or more identical or different radicals selected from C1-C12-alkyl, C1-C12-haloalkyl, F, Cl, Br, I, CN, NO2, SR19, OR20, COR21, COOR22 and CONR23R24;
RMib is F, Cl, Br, I, C1-C12-alkyl, C1-C12-haloalkyl, CN, NO2, SR19, OR20, COR21, COOR22, CONR23R24 or phenyl;
RMic is F, Cl, Br, I, C1-C12-alkyl, C1-C12-haloalkyl, CN, NO2, SR19, OR20, COR21, COOR22, CONR23R24 or phenyl;
RMb is F, Cl, Br, I, C1-Cu-alkyl, C1-C12-haloalkyl, CN, SR19, OR20, COR21, COOR22;
CONR23R24, C6-C10-aryl or heteroaryl, where the 2 last-mentioned radicals may be substituted by one or more identical or different radicals selected from C1-C12-alkyl, C1-C12-haloalkyl, F, Cl, Br, I, CN, NO2, SR19, OR20, COR21, COOR22 or CONR23R24;
RMc is F, Cl, Br, I, C1-C12-alkyl, C1-C12-haloalkyl, CN, NO2, SR19, OR20, COR21, COOR22, CONR23R24, phenyl, C3-C10-cycloalkyl or heterocycloalkyl, where the two last-mentioned radicals may be interrupted by one or more CO groups;
Z is C1-C20-alkylene or C6-C20-arylene,
where
C1-C20-alkylene may be interrupted by one or more nonadjacent groups RZi and/or may be substituted by one or more identical or different radicals RZa, and where C6-C20-arylene may be substituted by one or more radicals RZc,
where
RZi has one of the meanings indicated for RMi,
RZa has one of the meanings indicated for RMa,
RZc has one of the meanings indicated for RMc,
RN is selected independently of one another from hydrogen, C1-C20 alkyl, C1-C10-alkanoyl, C6-C10-aroyl, C1-C20-alkylsulfonyl, C2-C20-alkenylsulfonyl, C6-C10-arylsulfonyl, C3-C10-cycloalkyl, heterocycloalkyl, C6-C10-aryl and heteroaryl, where C3-C10-cycloalkyl and heterocycloalkyl may be interrupted by one or more CO groups, and the tautomers or stereoisomers thereof.

213 more elements

Dependencies are inferred from the claim text.

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Abstract

A heat-curable composition, comprising:

at least one compound which is capable of undergoing cationic polymerization;
and
at least one sulfonium sulfate selected from the group consisting of compounds of the formulae (Ia) and (Ib):
wherein:
Yn− is a monovalent or divalent anion selected from
n is one or two;
R1 is C1-C20-alkyl, C3-C20-cycloalkyl, heterocycloalkyl, a group A or a group B, where C1-C20-alkyl may be substituted by one or more identical or different radicals R1a and/or may be interrupted by one or more non-adjacent groups selected from —O—, —S—, —C(O)— and —N(RN)—,
where
R1a is F, Cl, Br, I, CN, SR19, OR20, COR21, COOR22, CONR23R24, C3-C20-cycloalkyl or heterocycloalkyl, where the two last-mentioned radicals may be interrupted by one or more CO groups, and/or may carry one or more identical or different radicals R1ab,
where
R1ab is F, Cl, Br, I, C1-C12-alkyl, C1-C12-haloalkyl, CN, SR19, OR20, COR21, COOR22 or CONR23R24;
where C3-C20-cycloalkyl and heterocycloalkyl may be interrupted by one or more CO groups and/or may be substituted by one or more identical or different radicals R1b,
where
R1b is F, Cl, Br, I, C1-C12-alkyl, C1-C12-haloalkyl, CN, SR19, OR20, COR21, COOR22 or CONR23R24;
where
the group of the formula A is
in which
# is the point of attachment to the sulfonium atom, and
where
the group of the formula B is
in which
# is the point of attachment to the sulfonium atom,
with the proviso that R1 is the group A or the group B, if R2 and R3 are both selected from the group consisting of C1-C20-alkyl;
C1-C20-alkyl substituted by one or more radicals R2a;
C1-C20-alkyl which is interrupted by one or more non-adjacent groups selected from —O—, —S—, —C(O)—, and —N(RN));
C1-C20-alkyl which is interrupted by one or more non-adjacent groups selected from —O—, —S—, —C(O)—, and —N(RN)) and substituted by one or more radicals R2a;
C3-C20-cycloalkyl;
C3-C20-cycloalkyl interrupted by one or more CO groups;
C3-C20-cycloalkyl substituted by one or more radicals R2b;
and C3-C20-cycloalkyl interrupted by one or more CO groups and substituted by one or more radicals R2b;
R2 and R3 are selected independently of one another from C1-C20-alkyl, C2-C20-alkenyl, C2-C20-alkynyl, C3-C20-cycloalkyl, heterocycloalkyl, C6-C20-aryl and heteroaryl,
where C1-C20-alkyl, C2-C20-alkenyl and C2-C20-alkynyl may be substituted by one or more identical or different radicals R2a and/or may be interrupted by one or more non-adjacent groups selected from —O—, —S—, —C(O)— and —N(RN)—,
where C3-C20-cycloalkyl and heterocycloalkyl may be interrupted by one or more CO groups, and/or may carry one or more identical or different radicals R2b,
where C6-C20-aryl and heteroaryl may be substituted by one or more identical or different radicals R2c,
where
R2a is selected from F, Cl, Br, I, CN, SR10, OR20, COR21, COOR22, CONR23R24, C3-C20-cycloalkyl and heterocycloalkyl, where the two last-mentioned radicals may be interrupted by one or more CO groups and/or may be substituted by one or more identical or different radicals R2ab, and also from the group consisting of heteroaryl and C6-C10-aryl, where the two last-mentioned radicals may be substituted by one or more identical or different radicals R2ac,
where
R2ab has one of the meanings indicated for R1ab,
R2ac is F, Cl, Br, I, C1-C12-alkyl, C1-C12-haloalkyl, CN, NO2, SR19, OR20, COR21, COOR22 or CONR23R24;
R2b is F, Cl, Br, I, C1-C12-alkyl, C1-C12-haloalkyl, CN, SR19, OR20, COR21, COOR22, CONR23R24, C6-C10-aryl or heteroaryl where the two last-mentioned radicals may be substituted by one or more identical or different radicals R2bc,
where
R2bc has one of the meanings indicated for R2ac;
R2c is F, Cl, Br, I, C1-C12-alkyl, C1-C12 haloalkyl, CN, NO2, SR19, OR20, COR21, COOR22, CONR23R24, phenyl,
C3-C10-cycloalkyl or heterocycloalkyl where the two last-mentioned radicals may be interrupted by one or more CO groups;
or
R1 and R2 or R1 and R3 may together form a straight-chain C2-C6-alkylene group, a straight-chain C2-C6-alkenylene group, or a —(CH2)a—C6H4—(CH2)b group, where a and b are an integer from 0 to 10 and the sum of a and b is 1 to 10, where alkylene, alkenylene and the alkylene moiety of —(CH2)a—C6H4—(CH2)b may be substituted by one or more identical or different radicals R32 and/or may be interrupted by one or more non-adjacent groups selected from —O—, —S—, —C(O)— and —N(RN)—;
or
R2 and R3 may together form a straight-chain C2-C6-alkylene, a straight-chain C2-C6-alkenylene, or a straight-chain —(CH2)c—C6H4—(CH2)d group, where c and d are an integer from 0 to 10 and the sum of c and d is 1 to 10, where alkylene, alkenylene and the alkylene moiety of —(CH2)c—C6H4—(CH2)d may be substituted by one or more identical or different radicals R32 and/or may be fused to 1 or 2 phenyl rings and/or may be interrupted by one or more non-adjacent groups selected from —O—, —S—, —C(O)— and —N(RN)—;
R4 is C1-C20-alkyl, C2-C20-alkenyl, C2-C20-alkynyl, C3-C20-cycloalkyl, heterocycloalkyl, C6-C20-aryl, heteroaryl, —NR11R12 or —N═CR13R14,
where C1-C20-alkyl, C2-C20-alkenyl and C2-C20-alkynyl may be substituted by one or more identical or different radicals R4a and/or may be interrupted by one or more non-adjacent groups selected from —O—, —S—, —C(O)— and —N(RN)—,
where C3-C20-cycloalkyl and heterocycloalkyl may be interrupted by one or more CO groups and/or may be substituted by one or more identical or different radicals R4b, and where C6-C20-aryl and heteroaryl may be substituted by one or more identical or different radicals R4c,
where
R4a is selected from F, Cl, Br, I, CN, SR19, OR20, COR21, COOR22, CONR23R24, C3-C20-cycloalkyl and heterocycloalkyl where the 2 last-mentioned radicals may be interrupted by one or more CO groups and/or may be substituted by one or more identical or different radicals R4ab, and also from the group consisting of heteroaryl and C6-C10-aryl, where the two last-mentioned radicals may be substituted by one or more identical or different radicals R4ac,
where
R4ab has one of the meanings indicated for R1ab,
R4ac has one of the meanings indicated for R2ac, and
in addition, if 2 radicals R4a are geminally bound, the 2 radicals R4a together may also form an N-hydroxyimino group;
R4b is F, Cl, Br, I, C1-C12-alkyl, CN, SR19, OR20, COR21, COOR22, CONR23R24, C6-C10-aryl or heteroaryl, where the two last-mentioned radicals may be substituted by one or more identical or different radicals R4bc,
where
R4bc has one of the meanings indicated for R2bc;
R4c is F, Cl, Br, I, C1-C12-alkyl, C1-C12-haloalkyl, CN, NO2, SR19, OR20, COR21, COOR22, CONR23R24, phenyl, C3-C10-cycloalkyl or heterocycloalkyl, where two last-mentioned radicals may be interrupted by one or more CO groups;
R5, R6, R7 and R8 are selected independently of one another from C1-C20-alkyl, C2-C20-alkenyl, C2-C20-alkynyl, C3-C20-cycloalkyl, heterocycloalkyl, C6-C20-aryl and heteroaryl,
where C1-C20-alkyl, C2-C20-alkenyl and C2-C20-alkynyl may be substituted by one or more identical or different radicals R5a and/or may be interrupted by one or more non-adjacent groups selected from —O—, —S—, —C(O)— and —N(RN)—,
where C3-C20-cycloalkyl and heterocycloalkyl may be interrupted by one or more CO groups and/or may be substituted by one or more identical or different radicals R5b, where C6-C20-aryl and heteroaryl may be substituted by one or more identical or different radicals R5c, where
R5a has one of the meanings indicated for R2a,
R5b has one of the meanings indicated for R2b,
R5c has one of the meanings indicated for R2c;
or
R5 and R6 and/or R7 and R8 may together form a straight-chain C2-C6-alkylene, a straight-chain C2-C6-alkenylene or a straight-chain —(CH2)c—C6H4—(CH2)d group, where c and d are an integer from 0 to 10 and the sum of c and d is 1 to 10, where alkylene, alkenylene and the alkylene moiety of —(CH2)c—C6H4—(CH2)d may be substituted by one or more identical or different radicals R32 and/or may be fused to 1 or 2 phenyl rings and/or may be interrupted by one or more non-adjacent groups selected from —O—, —S—, —C(O)— and —N(RN)—;
R9 and R10 are independently of one another selected from C1-C20-alkyl, C2-C20-alkenyl, C2-C20-alkynyl, C3-C20-cycloalkyl, heterocycloalkyl, C6-C20-aryl, heteroaryl, —NR11R12 and —N═CR13R14, where C1-C20-alkyl, C2-C20-alkenyl and C2-C20-alkynyl may be substituted by one or more identical or different radicals R9a and/or may be interrupted by one or more non-adjacent groups selected from —O—, —S—, —C(O)— and —N(RN)—, where C3-C20-cycloalkyl and heterocycloalkyl may be interrupted by one or more CO groups and/or may be substituted by one or more identical or different radicals R9b, where C6-C20-aryl and heteroaryl may be substituted by one or more identical or different radicals R9c, where
R9a has one of the meanings indicated for R4a,
R9b has one of the meanings indicated for R4b,
R9c has one of the meanings indicated for R4c;
R11 and R12 are independently of one another selected from hydrogen, C1-C20-alkyl, C2-C20-alkenyl, C2-C20-alkynyl, C3-C20-cycloalkyl, heterocycloalkyl, C6-C20-aryl, heteroaryl, C2-C20-alkanoyl, C3-C20-alkenoyl and C6-C10-aroyl,
where C1-C20-alkyl, C2-C20-alkenyl and C2-C20-alkynyl may be substituted by one or more identical or different radicals R11a and/or may be interrupted by one or more non-adjacent groups selected from —O—, —S—, —C(O)— and —N(RN)—,
where C3-C20-cycloalkyl and heterocycloalkyl may be interrupted by one or CO groups and/or may be substituted by one or more identical or different radicals R11b,
where C6-C20-aryl and heteroaryl may be may be substituted by one or more identical or different radicals R11c,
where C2-C20-alkanoyl and C3-C20-alkenoyl may be substituted by one or more identical or different radicals R11d,
where C6-C10-aroyl may be substituted by one or more identical or different radicals R11e,
R11a has one of the meanings indicated for R2a,
R11b has one of the meanings indicated for R2b,
R11c has one of the meanings indicated for R2c,
R11d is F, Cl, Br, I, CN, NO2, SR19, OR20, COR21, COOR22 or CONR23R24;
R11e is F, Cl, Br, I, C1-C12-alkyl, C1-C12-haloalkyl, CN, NO2, SR19, OR20, COR21, COOR22 or CONR23R24;
or
R11 and R12 may together form a straight-chain C2-C5-alkylene or a straight-chain C2-C5-alkenylene chain, where alkylene and alkenylene may be substituted by one or more identical or different radicals R11f and/or may be interrupted by one or more non-adjacent groups selected from —O—, —S—, —C(O)— and —N(RN)—,
or
R11 and R12 may together form an o-phenylenedicarbonyl or 1,8-naphthalenedicarbonyl group, where the two last mentioned radicals may be substituted by one or more identical or different radicals R11f, where
R11f has one of the meanings indicated for R11e;
R13 and R14 are, independently of one another, selected from hydrogen, CN, NO2, SR19, OR20, COR21, COOR22, CONR23R24, C1-C20-alkyl, C2-C20-alkenyl, C2-C20-alkynyl, C3-C20-cycloalkyl, heterocycloalkyl, C6-C20-aroyl, C6-C20-aryl and heteroaryl,
where C1-C20-alkyl, C2-C20-alkenyl and C2-C20-alkynyl may be substituted by one or more identical or different radicals R13a and/or may be interrupted by one or more non-adjacent groups selected from —O—, —S— —C(O)— and —N(RN)—,
where
C3-C20-cycloalkyl and heterocycloalkyl may be interrupted by one or more CO groups and/or may be substituted by one or more identical or different radicals R13b,
where
C6-C20-aroyl, C6-C20-aryl and C5-C20-heteroaryl may be substituted by one or more identical or different radicals R13c,
where
R13a is selected from F, Cl, Br, I, CN, SR19, OR20, COR21, COOR22, CONR23R24, C3-C20-cycloalkyl and heterocycloalkyl where the 2 last-mentioned radicals may be interrupted by one or more CO groups and/or may be substituted by one or more identical or different radicals R13ab, and also from the group consisting of phenyl and phenyl which is substituted by one or more identical or different radicals R13ac,
where
R13ab has one of the meanings indicated for R1ab,
R13ac has one of the meanings indicated for R2ac;
R13b is F, Cl, Br, I, C1-C12-alkyl, C1-C12-haloalkyl, CN, SR19, OR20, COR21, COOR22, CONR23R24, phenyl or phenyl which is substituted by one or more identical or different radicals R13bc, where
R13bc has one of the meanings indicated for R2ac;
R13c has one of the meanings indicated for R4c;
or
R13 and R14 may together form a straight-chain C2-C6-alkylene or a straight-chain C2-C6-alkenylene chain, where alkylene and alkenylene may be substituted by one or more identical or different radicals R32 and/or may be interrupted by one or more non-adjacent groups selected from —O—, —S—, —C(O)— and —N(RN)—;
R19 and R20 are selected independently of one another from hydrogen, C1-C20-alkyl, C2-C12-alkenyl, C3-C10-cycloalkyl, heterocycloalkyl, where the two last-mentioned radicals may be interrupted by one or more CO groups, C1-C20-alkyl which is interrupted by one or more non-adjacent groups selected from —O—, —S—, —C(O)— and —N(RN)—, C1-C8-alkyl substituted by one or more identical or different radicals R19a, —(CH2CH2O)mH with m being 1-20, —(CH2CH2O)n(CO)—(C1-C8-alkyl) with n being 1-20, C2-C8-alkanoyl, C2-C8-haloalkanoyl, C3-C6-alkenoyl, benzoyl where the last-mentioned radical may be substituted by one or more radicals selected independently of one another from F, Cl, Br, I, C1-C6-alkyl, OH and C1-C4-alkoxy, phenyl, naphthyl, where the two last-mentioned radicals may be substituted by one or more identical or different radicals R19c,
or phenyl or naphthyl which forms a 5- or 6-membered ring via the phenyl ring to which SR19 or OR20, respectively, is attached via a single bond, C1-C4-alkylene, O, S, CO or NR23,
where
R19a is F, Cl, Br, I, OH, SH, CN, C3-C10-cycloalkyl, heterocycloalkyl, phenyl, C3-C6 alkenoxy, —OCH2CH2CN, —OCH2CH2(CO)O(C1-C8-alkyl), —O(CO)—(C1-C8-alkyl), —O(CO)-phenyl, —(CO)OH or —(CO)O(C1-C8-alkyl),
R19c is F, Cl, Br, I, C1-C12-alkyl, C1-C12-haloalkyl, C1-C12-alkoxy, phenyl-C1-C3-alkyloxy, phenoxy, C1-C12-alkylsulfanyl, phenylsulfanyl, —(CO)O(C1-C8-alkyl), (CO)N(C1-C8-alkyl)2 or phenyl;
R21 is selected independently of one another from hydrogen, C1-C20-alkyl, C2-C12-alkenyl, C1-C20-alkyl which is interrupted by one or more non-adjacent groups selected from —O—, —S—, —CO— and —N(RN)—, C1-C8-alkyl substituted by one or more identical or different radicals R21a, —(CH2CH2O)oH with o being 1-20, —(CH2CH2O)p(CO)—(C1-C8-alkyl) with p being 1-20, C3-C10-cycloalkyl, heterocycloalkyl, where the two last-mentioned radicals may be interrupted by one or more CO groups, C6-C20-aryl and heteroaryl, where the two last-mentioned radicals may be substituted by one or more radicals identical or different radicals R21c,
where
R21a is F, Cl, Br, I, OH, SH, CN, phenyl, C3-C6 alkenoxy, —OCH2CH2CN, —OCH2CH2(CO)O(C1-C8-alkyl), —O(CO)—(C1-C8-alkyl), —O(CO)-phenyl, —(CO)OH or —(CO)O(C1-C8-alkyl), and
R21c has one of the meanings indicated for R19c;
R22 is selected independently of one another from hydrogen, C1-C20-alkyl, C2-C12-alkenyl, C2-C20-alkyl which is interrupted by one or more non-adjacent groups selected from —O—, —S—, —C(O)— and —NRN—, C1-C8-alkyl substituted by one or more identical or different radicals R22a, —(CH2CH2O)qH with q being 1-20, —(CH2CH2O)r(CO)—(C1-C8-alkyl) with r being 1-20, C3-C10-cycloalkyl, heterocycloalkyl, where the two last-mentioned radicals may be interrupted by one or more CO groups, phenyl and naphthyl, where the two last-mentioned radicals may be substituted by one or more identical or different radicals R22c,
where
R22a is F, Cl, Br, I, OH, SH, CN, C3-C6 alkenoxy, —OCH2CH2CN, —OCH2CH2(CO)O(C1-C8-alkyl), —O(CO)—(C1-C8-alkyl), —O(CO)-phenyl, —(CO)OH, —(CO)O(C1-C8-alkyl), phenyl or naphthyl, where the two last-mentioned radicals may be substituted by one or more identical or different radicals R22ac,
where
R22ac has one of the meanings indicated for R19c;
R22c has one of the meanings indicated for R19c;
R23 and R24 are, independently of one another, selected from hydrogen, OR20, C1-C20-alkyl, C2-C12-alkenyl, C2-C20-alkyl which is interrupted by one or more non-adjacent groups selected from —O—, —S—, —C(O)— and —NRN—, C1-C8-alkyl substituted by one or more identical or different radicals R23a, —(CH2CH2O)sH with s being 1-20, —(CH2CH2O)t(CO)—(C1-C8-alkyl) with t being 1-20, C2-C8alkanoyl, C2-C8-haloalkanoyl, C3-C6-alkenoyl, benzoyl which may be substituted by one or more identical or different radicals selected from F, Cl, Br, I, C1-C6-alkyl, —OH and C1-C4-alkoxy, C3-C10-cycloalkyl, heterocycloalkyl, where the two last-mentioned radicals may be interrupted by one or more CO groups, phenyl and naphthyl, where the two last-mentioned radicals may be substituted by one or more identical or different radicals R23c,
where
R23a is F, Cl, Br, I, OH, SH, CN, phenyl, C3-C6-alkenoxy, —OCH2CH2CN, —OCH2CH2(CO)O(C1-C8-alkyl), —O(CO)—(C1-C8-alkyl), —O(CO)-phenyl, —(CO)OH or —(CO)O(C1-C8-alkyl),
R23c has one of the meanings indicated for R19c;
or
R23 and R24 together may form a C2-C5-alkylene group, which may be interrupted by one or more non-adjacent groups selected from —O—, —S—, —C(O)— and —N(RN)—;
R25 and R26 are, each independently of one another, selected from hydrogen, F, Cl, Br, CN, NO2, SR19, OR20, COR21, COOR22, CONR23R24, C1-C20-alkyl, C3-C20-cycloalkyl, heterocycloalkyl, C6-C20-aryl and heteroaryl,
where
C1-C20-alkyl may be interrupted by one or more non-adjacent groups selected from —O—, —S—, —C(O)— and —N(RN)— and/or may be substituted by one or more identical or different radicals R25a,
where
C3-C20-cycloalkyl and heterocycloalkyl may be interrupted by one or more CO groups and/or may be substituted by one or more identical or different radicals R25b, and
where
C6-C20-aryl and heteroaryl may be substituted by one or more identical or different radicals R25c,
where
R25a has one of the meanings indicated for R13a;
R25b has one of the meanings indicated for R13b;
R25c has one of the meanings indicated for R13c;
R27, R28, R29, R30 and R31 are, each independently of one another, selected from hydrogen, F, Cl, Br, I, CN, NO2, SR19, OR20, COR21, COOR22, CONR23R24, C1-C20-alkyl, C2-C20-alkenyl, C2-C20-alkynyl, C3-C20-cycloalkyl, heterocycloalkyl, C6-C20-aryl and heteroaryl,
where
C1-C20-alkyl, C2-C20-alkenyl and C2-C20-alkynyl may be substituted one or more radicals identical or different radicals R27a and/or may be interrupted by one or more non-adjacent groups selected from —O—, —S—, —C(O)— and —N(RN)—,
where
C3-C20-cycloalkyl and heterocycloalkyl may be interrupted by one or more CO groups and/or may be substituted by one or more identical or different radicals R27b,
where
C6-C20-aryl and heteroaryl may be substituted by one or more identical or different radicals R27c,
where
R27a has one of the meanings indicated for R13a;
R27b has one of the meanings indicated for R13b;
R27c has one of the meanings indicated for R13c;
or
two radicals R27 and R28, R28 and R29, R29 and R30 and/or R30 and R31 may together form a straight-chain C2-C6-alkylene or a straight-chain C2-C6-alkenylene group, where the alkylene group and the alkenylene group may be substituted by one or more identical or different radicals R32 and/or may be fused to 1 or 2 C6-C10-aryl rings and/or may be interrupted by one or more non-adjacent groups selected from —O—, —S—, —C(O)— and —N(RN)—,
or
R25 and R27 may together form a C2-C6-alkylene chain, where alkylene may be substituted by one or more radicals R32 and/or may be interrupted by one or more non-adjacent groups selected from —O—, —S—, —C(O)— and —N(RN)—,
or
R25 and R27 may together form a 1,2-phenylene group, where 1,2-phenylene may be substituted by one or more identical or different radicals R32;
R32 is F, Cl, Br, I, CN, NO2, SR19, OR20, COR21, COOR22, CONR23R24, C1-C20-alkyl, C2-C20-alkenyl, C2-C20-alkynyl, C3-C20-cycloalkyl, heterocycloalkyl, C6-C20-aryl and heteroaryl;
where
C1-C20-alkyl, C2-C20-alkenyl and C2-C20-alkynyl may be interrupted by one or more non-adjacent groups selected from —O—, —S—, —C(O)— and —N(RN)— and/or may be substituted one or more radicals identical or different R32a,
where
C3-C20-cycloalkyl and heterocycloalkyl may be interrupted by one or more CO groups and/or may be substituted by one or more identical or different radicals R32b,
where
C6-C20-aryl and heteroaryl may be substituted by one or more radicals identical or different R32c,
where
R32a has one of the meanings indicated for R13a;
R32b has one of the meanings indicated for R13b;
and
R32c has one of the meanings indicated for R13c;
R33 and R34 are, each independently of one another are selected from hydrogen, F, Cl, Br, I, CN, NO2, SR19, OR20, COR21, COOR22, CONR23R24, C1-C20-alkyl, C3-C20-cycloalkyl, heterocycloalkyl, C6-C20-aryl and heteroaryl,
where
C1-C20-alkyl may be may be substituted by one or more radicals R33a and/or may be interrupted by one or more non-adjacent groups selected from —O—, —S—, —C(O)— and —N(RN)—,
where
C3-C20-cycloalkyl and heterocycloalkyl may be interrupted by one or more CO groups and/or may be substituted by one or more identical or different radicals R33b, and
where
C6-C20-aryl and heteroaryl may be substituted by one or more identical or different radicals R33c,
where
R33a has one of the meanings indicated for R13a;
R33b has one of the meanings indicated for R13b;
R33c has one of the meanings indicated for R13c;
R35, R36 and R37, each independently of one another are selected from hydrogen, F, Cl, Br, I, CN, NO2, SR10, OR20, COR21, COOR22, CONR23R24, C1-C20-alkyl, C2-C20-alkenyl, C2-C20-alkynyl, C3-C20-cycloalkyl, heterocycloalkyl, C6-C20-aryl and heteroaryl,
where
C1-C20-alkyl, C2-C20-alkenyl and C2-C20-alkynyl may be substituted by one or more identical or different radicals R35a and/or may be interrupted by one or more non-adjacent groups selected from —O—, —S—, —C(O)— and —N(RN)—,
where
C3-C20-cycloalkyl and heterocycloalkyl may be substituted by one or more identical or different radicals R35b, and
where
C6-C20-aryl and heteroaryl may be substituted by one or more identical or different radicals R35c,
where
R35a has one of the meanings indicated for R27a;
R35b has one of the meanings indicated for R27b;
R35c has one of the meanings indicated for R17c;
or
R35 and R36 may together form a straight-chain C2-C6-alkylene or a straight-chain C2-C6-alkenylene group, where alkylene and alkenylene may be substituted by one or more radicals identical or different R32 and/or may be interrupted by one or more non-adjacent groups selected from —O—, —S—, —C(O)— and —N(RN)—,
or
two radicals R33 and R35, R33 and R37, R34 and R35 and/or R34 and R37 may together form a straight-chain C2-C6-alkylene group, where the alkylene group may be substituted by one or more identical or different radicals R32 and/or may be interrupted by one or more non-adjacent groups selected from —O—, —S—, —C(O)— and —N(RN)—;
M is a divalent radical selected from C1-C20-alkylene, C2-C20-alkenylene, C2-C20-alkynylene, C3-C20-cycloalkylene, heterocycloalkylene, C6-C20-arylene and heteroarylene, where C1-C20-alkylene, C2-C20-alkenylene and C2-C20-alkynylene may be substituted by one or more identical or different radicals RMa and/or may be interrupted by one or more identical or different non-adjacent groups RMi,
where
C3-C20-cycloalkylene and heterocycloalkylene may be interrupted by one or more CO groups and/or may be substituted by one or more radicals
RMb;
where
C6-C20-arylene and heteroarylene may be substituted by one or more radicals RMc,
where
RMi is selected from —O—, —S—, —C(O)—, OC(O)—, —N(RN)—, C3-C20-cycloalkylene, —O—C3-C20-cycloalkylene, —O—C3-C20-cycloalkylene-O—, heterocycloalkylene, C6-C20-arylene, —O—C6-C20-arylene, —O—C6-C20-arylene-O—, —S—C6-C20-arylene, —S—C6-C20-arylene-S— and heteroarylene, where each cycloalkylene and heterocycloalkylene may be interrupted by one or more CO groups and/or may be substituted by one or more identical or different radicals RMib, and
where
each arylene and heteroarylene may be substituted by one or more radicals RMic,
RMa is F, Cl, Br, I, CN, SR19, OR20, COR21, COOR22, CONR23R24, C6-C10-aryl or heteroaryl where the 2 last-mentioned radicals may be substituted by one or more identical or different radicals selected from C1-C12-alkyl, C1-C12-haloalkyl, F, Cl, Br, I, CN, NO2, SR19, OR20, COR21, COOR22 and CONR23R24;
RMib is F, Cl, Br, I, C1-C12-alkyl, C1-C12-haloalkyl, CN, NO2, SR19, OR20, COR21, COOR22, CONR23R24 or phenyl;
RMic is F, Cl, Br, I, C1-C12-alkyl, C1-C12-haloalkyl, CN, NO2, SR19, OR20, COR21, COOR22, CONR23R24 or phenyl;
RMb is F, Cl, Br, I, C1-Cu-alkyl, C1-C12-haloalkyl, CN, SR19, OR20, COR21, COOR22;
CONR23R24, C6-C10-aryl or heteroaryl, where the 2 last-mentioned radicals may be substituted by one or more identical or different radicals selected from C1-C12-alkyl, C1-C12-haloalkyl, F, Cl, Br, I, CN, NO2, SR19, OR20, COR21, COOR22 or CONR23R24;
RMc is F, Cl, Br, I, C1-C12-alkyl, C1-C12-haloalkyl, CN, NO2, SR19, OR20, COR21, COOR22, CONR23R24, phenyl, C3-C10-cycloalkyl or heterocycloalkyl, where the two last-mentioned radicals may be interrupted by one or more CO groups;
Z is C1-C20-alkylene or C6-C20-arylene,
where
C1-C20-alkylene may be interrupted by one or more nonadjacent groups RZi and/or may be substituted by one or more identical or different radicals RZa, and where C6-C20-arylene may be substituted by one or more radicals RZc,
where
RZi has one of the meanings indicated for RMi,
RZa has one of the meanings indicated for RMa,
RZc has one of the meanings indicated for RMc,
RN is selected independently of one another from hydrogen, C1-C20 alkyl, C1-C10-alkanoyl, C6-C10-aroyl, C1-C20-alkylsulfonyl, C2-C20-alkenylsulfonyl, C6-C10-arylsulfonyl, C3-C10-cycloalkyl, heterocycloalkyl, C6-C10-aryl and heteroaryl, where C3-C10-cycloalkyl and heterocycloalkyl may be interrupted by one or more CO groups, and the tautomers or stereoisomers thereof.

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