US 10,241,399 B2 · Polymerizable composition comprising an oxime sulfonate as thermal curing agent

Abstract

The present invention relates to a polymerizable composition comprising at least one ethylenically unsaturated, polymerizable compound and at least one oxime sulfonate compound of the formula I QAaBbCc (I) where a is 0, 1, 2, 3, 4 or 6, b is 0, 1, 2, 3, 4 or 6, and c is 0, 1, 2, 3, 4 or 6, where the sum of a+b+c is 1, 2, 3, 4 or 6 where A is a group B is a group C is a group where # denotes the point of attachment to Q; X is S or NR14 and Q, R1, R2, R3 and R14 are as defined in claim 1 and in the description. 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.

An oxime sulfonate compound of the formula IA.1,

R1 is C1-C20-alkyl, C2-C20-alkenyl, C2-C20-alkynyl, C3-C20-cycloalkyl, heterocyclyl, C6-C20-aryl, heteroaryl, C1-C20-alkanoyl, C3-C20-cycloalkanoyl, C2-C20-alkenoyl, C6-C20-aroyl, CSNR12R13, C(O)OR9 or CSOR9,
where C1-C20-alkyl, C2-C20-alkenyl and C2-C20-alkynyl may be interrupted by one or more identical or different groups selected —O—, —S—, —N(R6)— and CO, and/or may carry one or more identical or different radicals R1a,
where C3-C20-cycloalkyl and heterocyclyl may be interrupted by one or more CO groups, and/or may carry one or more identical or different radicals R1b,
where C6-C20-aryl and heteroaryl may carry one or more identical or different radicals R1c,
where C1-C20-alkanoyl and C2-C20-alkenoyl may carry one or more identical or different radicals R1a,
where C3-C20-cycloalkanoyl may carry one or more identical or different radicals R1b,
where C6-C20-aroyl may carry one or more identical or different radicals R1d,
where
R1a is selected independently of one another from F, Cl, Br, I, CN, SR4, OR5, NR6R7, COR8, COOR9, CONR10R11, C3-C20-cycloalkyl which may be interrupted by one or more CO groups, heterocyclyl which may be interrupted by one or more CO groups, heteroaryl and C6-C10-aryl where the four last-mentioned radicals may carry one or more identical or different radicals R1aa,
where
R1aa is selected independently of one another from C1-C12-alkyl, C1-C12-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), C1-C12-haloalkyl, C1-C12-hydroxyalkyl, C2-C12-alkenyl, F, Cl, Br, I, NO2, SR4, OR5, NR6R7, COR8, COOR9 and CONR10R11;
R1b is selected independently of one another from F, Cl, Br, I, CN, SR4, OR5, NR6R7, COR8, COOR9, CONR10R11, C1-C12-alkyl, C1-C12-hydroxyalkyl, C1-C12-haloalkyl, C2-C12-alkenyl, heteroaryl and C6-C10-aryl where the two last-mentioned radicals may carry one or more identical or different radicals R1ba, where
R1ba has one of the meanings indicated for R1aa;
R1c is selected independently of one another from C1-C12-alkyl, C1-C12-haloalkyl, C1-C12-hydroxyalkyl, C2-C12-alkenyl, F, Cl, Br, I, CN, NO2, SR4, OR5, NR6R7, COR8, COOR9, CONR10R11, phenyl, heteroaryl, heterocyclyl and C3-C10-cycloalkyl where the two last-mentioned radicals may be interrupted by one or two C═O groups and where phenyl, heteroaryl, heterocyclyl and C3-C10-cycloalkyl may carry one or more identical or different radicals R1ca, where
R1ca has one of the meanings indicated for R1aa;
R1d is selected independently of one another from C1-C12-alkyl, C1-C12-haloalkyl, C1-C12-hydroxyalkyl, C2-C12-alkenyl, F, Cl, Br, I, CN, SR4, OR5, NR6R7, COR8, COOR9, CONR10R11, C3-C20-cycloalkyl which may be interrupted by one or more CO groups, heterocyclyl which may be interrupted by one or more CO groups, C6-C10-aryl and heteroaryl where the four last-mentioned radicals may carry one or more radicals R1da, where R1da has one of the meanings indicated for R1aa;
R2 is hydrogen, SR4, OR5, NR1R14, COR8, SO2R4, COOR9, CONR10R11, SO2NR10R11, PO(OR9)2, C1-C16-alkyl, C2-C20-alkenyl, C2-C20-alkynyl, C3-C20-cycloalkyl, heterocyclyl, C6-C20-aryl, heteroaryl, C1-C20-alkanoyl, C2-C20-alkenoyl, C3-C20-cycloalkanoyl, C6-C20-aroyl or a group E,
where C1-C16-alkyl, C2-C20-alkenyl and C2-C20-alkynyl may be interrupted by one or more identical or different groups selected from —O—, —S—, —N(R6)— and CO, and/or may carry one or more identical or different radicals R2a,
where C3-C20-cycloalkyl and heterocyclyl 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 carry one or more identical or different radicals R2c,
where C1-C20-alkanoyl and C2-C20-alkenoyl may carry one or more identical or different radicals R2a,
where C3-C20-cycloalkanoyl may carry one or more identical or different radicals R2b,
where C6-C20-aroyl may carry one or more identical or different radicals R2d,
where
R2a is selected independently of one another from F, Cl, Br, I, CN, SR4, OR5, NR6R7, COR8, COOR9, CONR10R11, C3-C20-cycloalkyl which may be interrupted by one or more CO groups, heterocyclyl which may be interrupted by one or more CO groups, heteroaryl and C6-C10-aryl where the four last-mentioned radicals may carry one or more identical or different radicals R2aa,
where
R2aa is selected independently of one another from C1-C12-alkyl, C1-C12-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), C1-C12-haloalkyl, C1-C12-hydroxyalkyl, C2-C12-alkenyl, phenyl, F, Cl, Br, I, CN, NO2, SR4, OR5, NR6R7, COR8, COOR9 and CONR10R11;
R2b has one of the meanings indicated for R1b;
R2c is selected independently of one another from C1-C12-alkyl, C1-C12-haloalkyl, C1-C12-hydroxyalkyl, C2-C12-alkenyl, F, Cl, Br, I, CN, NO2, SR4, NR6R7, COR8, COOR9, CONR10R11, phenyl, heteroaryl, heterocyclyl and C3-C10-cycloalkyl where the two last-mentioned radicals may be interrupted by one or two C═O groups and where phenyl, heteroaryl, heterocyclyl and C3-C10-cycloalkyl may carry one or more identical or different radicals R1ca;
R2d has one of the meanings indicated for R1d;
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;
R2e has one of the meanings indicated for R2e;
R2f is C1-C20-alkylene-COO−, C2-C20-alkenylene-COO−, C2-C20-alkynylene-COO−, C3-C20-cycloalkylene-COO−, heterocycloalkylene-COO−, C6-C20-arylene-COO−, heteroarylene-COO−, C1-C20-alkylene-S(O2)O−, C2-C20-alkenylene-S(O2)O−, C2-C20-alkynylene-S(O2)O−, C3-C20-cycloalkylene-S(O2)O−, heterocycloalkylene-S(O2)O−, C6-C20-arylene-S(O2)O−, heteroarylene-S(O2)O−, C1-C20-alkylene-OS(O2)O−, C2-C20-alkenylene-OS(O2)O−, C2-C20-alkynylene-OS(O2)O−, C3-C20-cycloalkylene-OS(O2)O−, heterocycloalkylene-OS(O2)O−, C6-C20-arylene-OS(O2)O− or heteroarylene-OS(O2)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(R6)— and CO, and/or may carry one or more identical or different radicals R2a,
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 R2b,
where each arylene and each heteroarylene may carry one or more radicals R2c,
An− is Cl−, Br−, I−, SCN−, BF4−, PF6−, ClO4−, SbF6−, AsF6−, C1-C20-alkyl-COO−, C1-C20-alkyl-S(O)2O−, C1-C20-alkyl-OS(O)2O−, C6-C20-aryl-COO−, C6-C20-aryl-S(O)2O− or C6-C20-aryl-OS(O)2O−, where the aryl moiety of the three last-mentioned radicals may be substituted by 1, 2, 3 or 4 identical or different C1-C20-alkyl;
or
—R2 together with —X—R1 may be X—(C1-C20-alkylene)-Y, X—(C2-C20-alkenylene)-Y, X—(C3-C20-cycloalkylene)-Y, X-(heterocycloalkylene)-Y, X-(o-phenylene)-Y, X-(o-xylylene)-Y, X-(o-phenylene-C1-C12-alkylene)-Y,
X—(C1-C12-alkylene-o-phenylene)-Y, X—(O—C1-C20-alkylene)-Y, X—(S—C1-C20-alkylene)-Y or X—(N(R6)—C1-C20-alkylene)-Y, Y being attached to the oxime carbon atom carrying X
where each alkylene and alkenylene may comprise one or more identical or different groups selected from O, S, NR6 and CO and/or may be substituted by one or more radicals R2g,
where cycloalkylene and heterocycloalkylene may be interrupted by one or more groups CO and/or may be optionally substituted by one or more identical or different radicals R2h,
where each phenylene and the phenylene moiety of o-xylylene may be substituted by one or more identical or different radicals R2h,
where
Y is O, S, NR14, CO, SC(O), OC(O), C(O)O, NR10C(O), C(O)NR10, NR10SO2 or a single bond;
R2g is independently of one another selected from F, Cl, Br, I, SR4, OR5, NR6R7, COR8, COOR9, CONR10R11, heteroaryl and C6-C10-aryl where the two-last-mentioned radicals may carry one or more radicals R2ga, where R2ga is phenoxy or has one of the meanings indicated for R1aa;
R2h is independently of one another selected from F, Cl, Br, I, SR4, OR5, NR6R7, COR8, COOR9, CONR10R11, C1-C12-alkyl, C1-C12-haloalkyl, heteroaryl and C6-C10-aryl where the two last-mentioned radicals may carry one or more radicals R2ha, where R2ha has one of the meanings indicated for R1aa;
or if X is S, —R2 together with —S—R1 may be S—C(S)—NR12—C(O) or S—C(═NOR15)—C(O)—NR12—C(O), where R15 is hydrogen or phenylsulfonyl where the phenyl moiety may be substituted by C1-C4-alkyl or C1-C4-alkoxy
R3 is C1-C20-alkyl, C2-C20-alkenyl, C2-C20-alkynyl, C3-C20-cycloalkyl, heterocyclyl, C6-C20-aryl or heteroaryl,
where C1-C20-alkyl, C2-C20-alkenyl and C2-C20-alkynyl may be interrupted by one or more identical or different groups selected from —O—, —S—, —N(R6)— and CO, and/or may carry one or more identical or different radicals R3a,
where C3-C20-cycloalkyl and heterocyclyl may be interrupted by one or more CO groups, and/or may carry one or more identical or different radicals R3b,
where C6-C20-aryl and heteroaryl may carry one or more identical or radicals R3c,
where
R3a has one of the meanings indicated for R2a;
R3b has one of the meanings indicated for R1b;
R3c has one of the meanings indicated for R1c;
or
—X—R1 and R3 may together form a divalent radical selected from
X—(C1-C20-alkylene)-Z, X—(C2-C20-alkenylene)-Z, X—(C3-C20-cycloalkylene)-Z, X-(heterocycloalkylene)-Z, X-(o-phenylene)-Z,
X-(o-xylylene)-Z, X—(C0-C12-alkylene-heteroarylene-C0-C12-alkylene)-Z;
X-(o-phenylene-C1-C12-alkylene)-Z,
X—(C1-C12-alkylene-o-phenylene)-Z and S—C(S)—NR12—C(O),
where Z is attached to the sulfur atom of the sulfonate group, where each alkylene and each alkenylene may be interrupted by one or more identical or different groups selected from O, S, NR6 and CO and/or may be substituted by one or more radicals R3g,
where each cycloalkylene and each heterocycloalkylene may be interrupted by one or more groups CO and/or may be optionally substituted by one or more identical or different radicals R3h,
where each phenylene and the phenylene moiety of o-xylylene may be substituted by one or more identical or different radicals R3h, where
R3g has one of the meanings indicated for R2g;
R3h has one of the meanings indicated for R2h;
and
Z is O, S, NR14, CO, OC(O), SC(O), C(O)O, NR10C(O), C(O)NR10, NR10 (SO2) or a single bond;
R4 is selected independently of one another from hydrogen, C1-C20-alkyl, C2-C12-alkenyl,
C3-C10-cycloalkyl, heterocyclyl, where the two last-mentioned radicals may be interrupted by one or more C═O groups,
C1-C20-alkyl which is interrupted by one or more identical or different groups selected from —O—, —S—, —N(C1-C8-alkyl)- and CO, and/or may carry one or more identical or different radicals R4a,
C2-C12-alkenyl which is interrupted by one or more identical or different groups selected from —O—, —S—, and —N(C1-C8-alkyl)-,
—(CH2CH2O)mH, with m being 1-20,
—(CH2CH2O)n(CO)—(C1-C8-alkyl), with n being 1-20,
C2-C8-alkanoyl, C3-C6-alkenoyl, where the two-last mentioned radicals may be substituted by one or more identical or different radicals selected from F, Cl, Br, I, OH or C1-C6-alkoxy,
benzoyl which may be substituted by one or more identical or different radicals selected from F, Cl, Br, I, C1-C6-alkyl, OH or C1-C6-alkoxy,
phenyl and naphthyl, where the two last-mentioned radicals may be substituted by one or more identical or different radicals R4c,
or phenyl or naphthyl which forms a 5- or 6-membered ring with the phenyl ring to which the SR4 is attached via a single bond, C1-C4-alkylene, O, S, NR6 or CO,
where
R4a is selected independently of one another from F, Cl, Br, I, C3-C10-cycloalkyl, heterocyclyl, phenyl, OH, SH, CN, C3-C6-alkenoxy, OCH2CH2CN, OCH2CH2(CO)O(C1-C8-alkyl), O(CO)—(C1-C8-alkyl), O(CO)-phenyl, (CO)OH and (CO)O(C1-C8-alkyl);
R4c is selected independently of one another from F, Cl, Br, I, C1-C12-alkyl, C1-C12-haloalkyl, C1-C12-alkoxy, phenyl-C1-C3-alkoxy, phenoxy, C1-C12-alkylsulfanyl, phenylsulfanyl, —(CO)O(C1-C8-alkyl), (CO)N(C1-C8-alkyl)2 and phenyl;
R5 is selected independently of one another from hydrogen, C1-C20-alkyl, C2-C12-alkenyl,
C3-C10-cycloalkyl, heterocyclyl, where the two last-mentioned radicals may be interrupted by one or two C═O groups,
C1-C20-alkyl which is interrupted by one or more identical or different groups selected from —O—, —S—, —N(C1-C8-alkyl)- and CO, and/or may carry one or more identical or different radicals R5a,
C2-C12-alkenyl which is interrupted by one or more identical or different groups selected from —O—, —S—, and —N(C1-C8-alkyl)-,
—(CH2CH2O)mH, with m being 1-20,
—(CH2CH2O)n(CO)—(C1-C8-alkyl), with n being 1-20,
C2-C8-alkanoyl, C3-C6-alkenoyl, where the two-last mentioned radicals may be substituted by one or more identical or different radicals selected from F, Cl, Br, I, OH or C1-C6-alkoxy,
C2-C8-alkanoyl, which is interrupted by one or more identical or different groups selected from —O— and —S— and may be substituted by one or more identical or different radicals selected from hydroxyaminylene (═N—OH), F, Cl, Br, I, OH and C1-C6-alkoxy,
benzoyl which may be substituted by one or more identical or different radicals selected from F, Cl, Br, I, C1-C6-alkyl, OH or C1-C6-alkoxy,
phenyl and naphthyl, where the two last-mentioned radicals may be substituted by one or more identical or different radicals R5c,
or phenyl or naphthyl which forms a 5- or 6-membered ring with the phenyl ring to which the OR5 is attached via a single bond, C1-C4-alkylene, O, S, NR6 or CO, where
R5a has one of the meanings indicated for R4a;
R5c has one of the meanings indicated for R4c;
R6, R10 and R12 are selected independently of one another from hydrogen, OR5, C1-C20-alkyl, C2-C12-alkenyl,
C3-C10-cycloalkyl, heterocyclyl, where the two last-mentioned radicals may be interrupted by one or two C═O groups,
C1-C20-alkyl which is interrupted by one or more identical or different groups selected from —O—, —S—, —N(C1-C8-alkyl)- and CO, and/or may carry one or more identical or different radicals R6a,
C2-C12-alkenyl which is interrupted by one or more identical or different groups selected from —O—, —S—, and —N(C1-C8-alkyl)-,
—(CH2CH2O)oH, with o being 1-20,
—(CH2CH2O)p(CO)—(C1-C8-alkyl), with p being 1-20,
C2-C8-alkanoyl, C3-C6-alkenoyl, where the two-last mentioned radicals may be substituted by one or more identical or different radicals selected from F, Cl, Br, I, OH or C1-C6-alkoxy,
benzoyl which may be substituted by one or more identical or different radicals selected from F, Cl, Br, I, C1-C6-alkyl, —OH or C1-C6-alkoxy,
phenyl and naphthyl, where the two last-mentioned radicals may be substituted by one or more identical or different radicals R6c,
where
R6a has one of the meanings indicated for R4a;
R6c has one of the meanings indicated for R4c;
R7, R11 and R13 are independently of one another selected from OR5, C1-C20-alkyl, C2-C12-alkenyl,
C3-C10-cycloalkyl, heterocyclyl, where in the two last-mentioned radicals one or two CH2 groups may be replaced by a C═O group,
C1-C20-alkyl which is interrupted by one or more identical or different groups selected from —O—, —S—, —N(C1-C8-alkyl)- and CO, and/or may carry one or more identical or different radicals R7a,
C2-C12-alkenyl which is interrupted by one or more identical or different groups selected from —O—, —S—, and —N(C1-C8-alkyl)-,
—(CH2CH2O)qH, with q being 1-20,
—(CH2CH2O)r(CO)—(C1-C8-alkyl), with r being 1-20,
C2-C8-alkanoyl, C3-C6-alkenoyl, where the two-last mentioned radicals may be substituted by one or more identical or different radicals selected from F, Cl, Br, I, OH or C1-C6-alkoxy,
benzoyl which may be substituted by one or more identical or different radicals selected from F, Cl, Br, I, C1-C6-alkyl, OH or C1-C6-alkoxy,
phenyl and naphthyl, where the two last-mentioned radicals may be substituted by one or more identical or different radicals R7c,
where
R7a has one of the meanings indicated for R4a;
R7c has one of the meanings indicated for R4c;
or
R6 and R7 together with the nitrogen atom to which they are attached form a saturated 5-, 6- or 7-membered nitrogen heterocycle which may have a further heteroatom or heteroatomic group selected from the group consisting of CO, O, S and N(C1-C8-alkyl) as ring member and which may carry 1, 2, 3 or 4 C1-C4-alkyl;
or
R10 and R11 together with the nitrogen atom to which they are attached form a saturated 5-, 6- or 7-membered nitrogen heterocycle which may have a further heteroatom or heteroatomic group selected from the group consisting of CO, O, S and N(C1-C8-alkyl) as ring member and which may carry 1, 2, 3 or 4 C1-C4-alkyl;
or
R12 and R13 together with the nitrogen atom to which they are attached form a saturated 5-, 6- or 7-membered nitrogen heterocycle which may have a further heteroatom or heteroatomic group selected from the group consisting of CO, O, S and N(C1-C8-alkyl) as ring member and which may carry 1, 2, 3 or 4 C1-C4-alkyl;
R8 is independently of one another selected from hydrogen, C1-C20-alkyl, C2-C12-alkenyl,
C3-C10-cycloalkyl, heterocyclyl, where the two last-mentioned radicals may be interrupted by one or more C═O groups,
C1-C20-alkyl which is interrupted by one or more identical or different groups selected from —O—, —S—, —N(C1-C8-alkyl)- and CO, and/or may carry one or more identical or different radicals R8a,
C2-C12-alkenyl which is interrupted by one or more identical or different groups selected from —O—, —S—, and —N(C1-C8-alkyl)-,
—(CH2CH2O)sH, with s being 1-20,
—(CH2CH2O)t(CO)—(C1-C8-alkyl), with t being 1-20,
C6-C20-aryl and heteroaryl, where the two last-mentioned radicals may be substituted by one or more identical or different radicals R8c,
where
R8a has one of the meanings indicated for R4a;
R8c has one of the meanings indicated for R4c;
R9 is independently of one another selected from hydrogen, C1-C20-alkyl, C2-C12-alkenyl,
C3-C10-cycloalkyl, heterocyclyl, where the two last-mentioned radicals may be interrupted by one or more C═O groups,
C1-C20-alkyl which is interrupted by one or more identical or different groups selected from —O—, —S—, —N(C1-C8-alkyl)- and CO, and/or may carry one or more identical or different radicals R9a,
C2-C12-alkenyl which is interrupted by one or more identical or different groups selected from —O—, —S—, and —N(C1-C8-alkyl)-,
—(CH2CH2O)uH, with u being 1-20,
—(CH2CH2O)v(CO)—(C1-C8-alkyl), with v being 1-20,
phenyl and naphthyl, where the two last-mentioned radicals may be substituted by one or more identical or different radicals R9c,
where
R9a has one of the meanings indicated for R4a;
R9c has one of the meanings indicated for R4c;
R14 is C1-C20-alkyl, C2-C20-alkenyl, C2-C20-alkynyl, C3-C20-cycloalkyl, heterocyclyl, C6-C20-aryl, heteroaryl, C1-C20-alkanoyl, C2-C20-alkenoyl, C3-C20-cycloalkanoyl, C6-C20-aroyl, CSNR12R13 or CSOR9,
where C1-C20-alkyl, C2-C20-alkenyl and C2-C20-alkynyl may be interrupted by one or more identical or different groups selected —O—, —S—, —N(R6)— and CO and/or may carry one or more identical or different radicals R14a,
where C3-C20-cycloalkyl and heterocyclyl may be interrupted by one or more CO groups and/or may carry one or more identical or different radicals R14b,
where C6-C20-aryl, heteroaryl may carry one or more identical or radicals R14c,
where C1-C20-alkanoyl, C2-C20-alkenoyl may carry one or more identical or different radicals R14a,
where C3-C20-cycloalkanoyl may carry one or more identical or different radicals R14b,
where C6-C20-aroyl may carry one or more identical or different radicals R14d,
where
R14a has one of the meanings indicated for R2a,
R14b has one of the meanings indicated for R1b,
R14c has one of the meanings indicated for R1c;
R14d has one of the meanings indicated for R1a;
or
R1 together with R14 may be a divalent bridging group having 1 to 20 atoms between the flanking bonds;
except for compounds of the formula IA.1 in which
X—R1 and R2 together are N(CH3)-ethylene-N(CH3), R3 is phenyl or p-tolyl;
X—R1 and R2 together are CON(benzyl)-ethylene-S, R3 is phenyl, tolyl or fluorophenyl;
X—R1 is 3,4,5-trihydroxymethyl-6-hydroxymethyl-tetrahydropyran-2-ylsulfanyl and R2 is benzyl, R3 is 4-methylphenyl;
X—R1 and R2 together are N(CH3)-ethylene-O, R3 is p-tolyl;
X—R1 and R2 together are N(CH3)-o-phenylene-S, R3 is p-tolyl;
X—R1 and R2 together are N(CH3)-propylene, R3 is p-tolyl;
X—R1 is SCH3 and R2 is propyl or allyl, R3 is p-tolyl;
X—R1 is SCH3 or SC2H5 and R2 is methyl or ethyl, R3 is p-tolyl;
X—R1 is N(CH3)CH2CH2OH and R2 is phenyl, R3 is p-tolyl;
X—R1 is piperidino or N(C2H5)2 and R2 is CN, R3 is p-tolyl;
X—R1 is N(CH3)2 and R2 is 2,6-dichlorophenyl, R3 is methyl;
X—R1 is SC(S)NR12R13, where NR12R13 is N(CH3)2, N(C2H5)2, morpholino, piperidino or pyrrolidino and R2 is phenyl, 3-nitrophenyl, 4-nitrophenyl or 4-chlorophenyl, R3 is methyl, and
X—R1 and R2 together are S-(1,2-phenylene)-CO and R3 is phenyl.

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Polymerizable composition comprising an oxime sulfonate as thermal curing agent

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Polymerizable composition comprising an oxime sulfonate as thermal curing agent

Life of this patent

Abstract

Claims10