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US 4,537,923 AGranted
Polyalkylpiperidinesulfonic acid esters
AssigneeCiba-Geigy Corporation
InventorsMario Slongo, Friedrich Karrer
Life of this patent
Estimating the term…
Abstract
Polyalkylpiperidinesulfonic acid esters of the formulae I and II B--X--O--SO.sub.2 --A).sub.m (I) (B'--X--O--SO.sub.2).sub.2 A' (II), in which A, A', B, B', X and m are as defined in claim 1, the polyalkylpiperidine group being present in each of the substituents B and B'. These esters are suitable for use as curing catalysts for acid-curable resins and act therein, at the same time, as light stabilizers.
Claims9
A composition of matter containing an acid-curable resin and a compound of the formulae I
- B--X--O--SO.sub.2 --A).sub.m (I)
- in which m is a number 1 to 3, X is a direct bond or a group of the formula III ##STR69## which is attached via C* to the oxygen of the sulfo group, p being zero if the group of the formula III is attached to a nitrogen atom of B, and p otherwise being the number 1, and R.sup.1, R.sup.2 and R.sup.3 independently of one another being hydrogen or methyl, A is C.sub.1 -C.sub.20 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.2 -C.sub.12 -alkenyl, C.sub.7 -C.sub.12 -aralkyl, C.sub.6 -C.sub.10 -aryl, C.sub.7 -C.sub.30 -alkaryl, C.sub.5 -C.sub.8 -cycloalkyl, trifluoromethyl or camphoryl, each of which is unsubstituted or substituted by hydroxyl, a group --N(R.sup.4)(R.sup.5) or --C(CH.sub.3).sub.2 --CH.sub.2 --N(R.sup.6)--C(O)--C(R.sup.7).dbd.CH.sub.2, in which R.sup.4, R.sup.5 and R.sup.6 are hydrogen or C.sub.1 -C.sub.12 -alkyl and R is hydrogen or methyl, or a group of the formula ##STR70## or of the formula ##STR71## and B, provided that m=1, is a group of the formulae IV to X ##STR72## in addition, B, provided that m=1, and provided that X is a group of the formula III, can also be a group of the formulae XI to XVI ##STR73## if m=2, B is a group of the formulae XVII to XX ##STR74## in addition, if m=2 and if X is a group of the formula III, B can also be a group of the formulae XXI to XXV ##STR75## and, if m=3, B is a group of the formula XXVI ##STR76## and, if the formulae IV to XXV, R is hydrogen or methyl, R.sup.9 is hydrogen, C.sub.1 -C.sub.20 -alkyl, C.sub.3 -C.sub.5 -alkenyl, C.sub.3 -C.sub.5 -alkynyl, C.sub.7 -C.sub.12 -aralkyl, C.sub.1 -C.sub.18 -acyl, C.sub.3 -C.sub.10 -alkoxycarbonylalkyl, C.sub.2 -C.sub.4 -hydroxyalkyl, cyanomethyl, oxyl, a group of the formula --CH.sub.2 --CH(OH)--CH.sub.2 --OR.sup.27 or a group of the formula --C(O)--N(R.sup.22)(R.sup.23), R.sup.10 is hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, phenyl, phenoxy which is unsubstituted or substituted in the phenyl nucleus by C.sub.1 -C.sub.4 -alkyl, or phenoxymethyl, R.sup.11 is hydrogen, hydroxyl, C.sub.1 -C.sub.12 -alkoxy, C.sub.3 -C.sub.5 -alkenyloxy, C.sub.1 -C.sub.12 -acyloxy, C.sub.1 -C.sub.12 -acylamino, C.sub.2 -C.sub.14 -alkoxycarbonyl or a group of the formula ##STR77## --C(O)--N(R.sup.24)(R.sup.25), --OC(O)--N(R.sup.24)(R.sup.25), or --CH.sub.2 --COOR.sup.24, R.sup.12 is hydrogen, C.sub.1 -C.sub.12 -alkyl, C.sub.3 -C.sub.5 alkenyl, C.sub.3 -C.sub.5 -alkynyl, C.sub.7 -C.sub.12 -aralkyl, C.sub.1 -C.sub.18 -acyl, cyanomethyl or C.sub.2 -C.sub.4 -hydroxyalkyl, R.sup.13 is hydrogen or C.sub.1 -C.sub.4 -alkyl, R.sup.14 is hydrogen, C.sub.1 -C.sub.20 -alkyl, C.sub.3 -C.sub.5 -alkenyl C.sub.3 -C.sub.5 -alkynyl, C.sub.7 -C.sub.12 -aralkyl or C.sub.6 -C.sub.8 -cycloalkyl, R.sup.15 is hydrogen, C.sub.1 -C.sub.12 -alkyl, C.sub.3 -C.sub.5 -alkenyl, C.sub.7 -C.sub.12 -aralkyl, C.sub.1 -C.sub.18 -acyl, cyanomethyl or C.sub.2 -CHD 4-hydroxyalkyl, R.sup.16 is hydrogen, methyl or ethyl, R.sup.17 and R.sup.18 independently of one another are hydrogen or C.sub.1 -C.sub.6 -alkyl or R.sup.17 and R.sup.18 together are one of the groups of the formulae ##STR78## R.sup.19 and R.sup.20 independently of one another are hydrogen, C.sub.1 -C.sub.12 -alkyl, phenyl which is unsubstituted or substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.5 -C.sub.8 -cycloalkyl or C.sub.7 -C.sub.12 -aralkyl or R.sup.19 and R.sup.20 together are C.sub.4 -C.sub.11 -alkylene, R.sup.21 is hydrogen, C.sub.1 -C.sub.12 -alkyl, C.sub.3 -C.sub.5 -alkenyl, C.sub.1 -C.sub.18 -acyl or C.sub.7 -C.sub.12 -aralkyl, R.sup.22 and R.sup.23 independently of one another are hydrogen, C.sub.1 -C.sub.12 -alkyl, C.sub.3 -C.sub.5 -alkenyl, phenyl or cyclohexyl, R.sup.24 is C.sub.1 -C.sub.12 -alkyl, R.sup.25 is hydrogen or C.sub.1 -C.sub.12 -alkyl, R.sup.26 is C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.12 -alkoxy, phenyl, benzyl or phenoxy, R.sup.27 is C.sub.1 -C.sub.4 -alkyl or phenyl, r is a number 1 to 4, q is the number 0 or 1, k is a number 4 to 11, Y is ethylene, 1,4-but-2-enylene or o-, p- or m-xylylene, Z is a group of the formulae --O--R.sup.28 --O--, --OC(O)--R.sup.29 --C(O)O--, --N(R.sup.30)--C(O)--R.sup.31 --C(O)--N(R.sup.30)--, --N(R.sup.30)--C(O)--C(O)--N(R.sup.30), --C(O)O--R.sup.31 --OC(O)-- or ##STR79## R.sup.28 is C.sub.2 -C.sub.20 -alkylene, o-, m- or p-xylylene or 1,2-, 1,3- or 1,4-dimethylenecyclohexylene, R.sup.29 is C.sub.2 -C.sub.20 -alkylene, o-, m- or p-phenylene or C.sub.8 -C.sub.12 -arylenedialkylene, R.sup.30 is hydrogen, C.sub.1 -C.sub.12 -alkyl, C.sub.7 -C.sub.12 -aralkyl, C.sub.5 -C.sub.8 -cycloalkyl or phenyl which is unsubstituted or substituted by C.sub.1 -C.sub.4 -alkyl,
- R.sup.31 is C.sub.2 -C.sub.20 -alkylene or o-, m- or p-phenylene or 1,2-, 1,3- or 1,4-cyclohexylene, each of which is unsubstituted or substituted by C.sub.1 -C.sub.4 -alkyl, and R.sup.32 is ethylene or propylene, and acid addition salts thereof.
Dependencies are inferred from the claim text.