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US 4,309,546 AGranted
Piperidino pyrrolidinones
AssigneeCiba-Geigy Corporation
InventorFriedrich Karrer
Life of this patent
Estimating the term…
Abstract
Pyrrolidiones of the formula I ##STR1## wherein n is 1, 2, 3 or 4, R.sub.1 is free or esterified hydroxyl or hydroxyl which has been converted to a salt or is substituted or unsubstituted amino, X is a direct bond or a linking member and Pip is a substituted or unsubstituted 2,2,6,6-tetraalkylpiperidin-4-yl or a 2,2,6,6-tetraalkylpiperidin-4-ylidene, which pyrrolidones can be oligomerized or polymerized by linking R.sub.1 with X or by linking R.sub.1 with Pip. These compounds are used as light stabilizers for polymers.
Claims9
A pyrrolidone of the formula I ##STR39## wherein n is 1, 2, 3 or 4;
- R.sub.1 is hydroxyl, hydroxyl converted to Ca, Mg, Al, Zn, Co or Ni salts, or, when n is 1, is C.sub.1-20 alkoxy, C.sub.3-20 oxaalkoxy, C.sub.3-20 alkenyloxy, C.sub.3-6 alkynyloxy, C.sub.5-7 cycloalkoxy, C.sub.6-18 aryloxy, (C.sub.1-8 alkyl)-phenoxy, halogenophenoxy, hydroxyphenoxy, (C.sub.1-8 alkyl)-hydroxyphenoxy, C.sub.7-16 aralkoxy which can be substituted in the phenyl nucleus by C.sub.1-8 alkyl, halogen or hydroxyl, or also 2-hydroxyethoxy, which can be substituted in the 2-position by alkyl, phenyl or phenoxymethyl, or also amino, C.sub.1-20 alkylamino, C.sub.3-4 alkenylamino, di-C.sub.1-20 -alkylamino, di-C.sub.3-14 -alkenylamino, C.sub.5-7 cycloalkylamino, di-C.sub.5-7 -cycloalkylamino, C.sub.6-18 arylamino, (C.sub.1-8 alkylphenyl)-amino, (halophenyl)amino, (hydroxyphenyl)amino or (C.sub.1-8 alkylhydroxyphenyl)amino, while the amino group can also be N-substituted by C.sub.1-8 alkyl, or a radical of the formula IVa ##STR40## in which R.sub.4 is hydrogen or methyl, R.sub.16 is hydrogen, C.sub.1-16 alkyl, C.sub.3-8 alkenyl, propargyl, C.sub.7-16 aralkyl, C.sub.1-4 alkanoyl, C.sub.3-5 alkenoyl, C.sub.3-6 .beta.-hydroxyalkyl, C.sub.8-12 .beta.-hydroxyaralkyl, (C.sub.1-4 alkoxycarbonyl) methyl, oxyl or 2-hydroxy-3-phenoxypropyl, and Z is O, NH or N(C.sub.1-12 alkyl);
- when n is 2, R.sub.1 is --O--R.sub.3 --O--, in which R.sub.3 is C.sub.2-20 alkylene, C.sub.4-8 alkenylene, C.sub.4 alkynylene, C.sub.5-6 cycloalkylene, C.sub.6-10 arylene or C.sub.7-16 aralkylene, or also ##STR41## in which R.sub.4 is hydrogen or methyl and R.sub.5 is 2-butenylene, p-phenylenedimethylene, or --N(R.sub.6)--R.sub.7 --N(R.sub.6)--, in which R.sub.6 is hydrogen, C.sub.1-6 alkyl, C.sub.3-5 alkenyl, C.sub.5-6 cycloalkyl, phenyl, C.sub.7-12 aralkyl or 2,2,6,6-tetramethylpiperidin-4-yl with hydrogen, methyl or benzyl substituted at the piperidine nitrogen atom and R.sub.7 is C.sub.2-12 alkylene, C.sub.3-12 oxalkylene, C.sub.3-12 azalkylene, C.sub.6-12 arylene, C.sub.8-15 aralkylene or C.sub.5-6 cycloalkylene, or also --O--CH.sub.2 --C(OH)(R.sub.8)--R.sub.9 --C(OH)(R.sub.8)--CH.sub.2 --O--, in which R.sub.8 is hydrogen or methyl, or in which the radicals R.sub.8 together with the radical to which they are linked can form a 5- or 6-membered cycloalkyl ring, and in which R.sub.9 is a direct bond, C.sub.1-6 alkylene or C.sub.3-6 oxalkylene or in which R.sub.9 is VI or VII ##STR42## and R.sub.10 and R.sub.11 are hydrogen or C.sub.1-4 alkyl, or R.sub.10 and R.sub.11 together are tetramethylene or pentamethylene;
- when n is 3, R.sub.1 is a trioxy radical of a C.sub.3-20 alkanetriol in which one carbon atom is attached to not more than one oxygen atom, or also a radical VIII ##STR43## in which R.sub.12 is hydrogen, C.sub.1-4 alkyl, C.sub.3-5 alkenyl, phenyl or benzyl, and in which R.sub.13 is a trivalent radical of C.sub.3-20 alkyl, C.sub.6-12 aryl or C.sub.7-16 aralkyl, or also a radical IX ##STR44## in which R.sub.8 is hydrogen or methyl or two radicals R.sub.8 together with the radical to which they are linked form a 5- or 6-membered cycloalkyl ring, and in which R.sub.14 is a trivalent radical of C.sub.3-18 alkyl, or R.sub.14 is X ##STR45## in which R.sub.10 and R.sub.11 are hydrogen or C.sub.1-4 alkyl, or R.sub.10 and R.sub.11 together are tetramethylene or pentamethylene;
- and
- when n is 4, R.sub.1 is a tetroxy radical of a C.sub.4-20 alkanetetraol in which one carbon atom is attached to not more than one oxygen atom, or also a radical XII ##STR46## in which R.sub.12 is hydrogen, C.sub.1-4 alkyl, C.sub.3-5 alkenyl, phenyl or benzyl and R.sub.15 is a tetravalent radical of C.sub.3-20 alkyl, C.sub.6-12 aryl or C.sub.7-16 aralkyl;
- X-Pip is a radical of the formulae XIII-XX ##STR47## in which R.sub.4, R.sub.5, R.sub.7 and R.sub.16 are as previously defined, R.sub.17 is oxygen or NR.sub.18 with R.sub.18 being hydrogen, methyl, benzyl, allyl or C.sub.2-5 alkanoyl, p is 0 or 2 and q is 2, 3, 4 or 5;
- or the oligomers or polymers of said pyrrolidones corresponding to the formulae III or IV ##STR48## wherein X--Pip is as defined above, X--Pip' corresponds to X--Pip, R.sub.1 ' corresponds to the radical R.sub.1 and E is hydrogen or C.sub.1-6 alkoxy.
4 more elements
Dependencies are inferred from the claim text.