N-acyloxy hindered amine stabilizers

Claim 2

A stabilized ambient curable or acid catalyzed thermosetting coating composition containing an effective stabilizing amount of a hindered amine compound containing the group wherein R is hydrogen or methyl and R 1 is a group wherein D is C 1 -C 18 alkyl, C 1 -C 18 alkoxy, phenyl, phenyl substituted by hydroxy, Ci-C 4 alkyl or C 1 -C 4 alkoxy, or D is amino or amino mono- or disubstituted by C 1 -C 12 alkyl or phenyl.

Claim 3

The composition according to claim 1, which contains a hindered amine compound corresponding to one of the formulae A-N wherein R is hydrogen or methyl, R 1 is a group D-CO- , wherein D is C 1 -C 18 alkyl, C 1 -C 18 alkoxy, phenyl, phenyl substituted by hydroxy, C 1 -C 4 alkoxy, or amino oramino mono-or disubstituted by C 1 -C 12 alkyl or phenyl; m is 1-4, when m is 1, R 2 is hydrogen, C 1 -C 18 alkyl optionally interrupted by one or more oxygen atoms, C 2 -C 12 alkenyl, C 6 -C 10 aryl, C 7 -C 18 aralkyl, glycidyl, a monovalent acyl radical of an aliphatic, cycloaliphatic, araliphatic or aromatic carboxylic acid, or of a carbamic acid, or R 2 is a group wherein x is 0 or 1, or is a group wherein y is 2-4; when m is 2, R 2 is C 1 -C 12 alkylene, C 4 -C 12 alkenylene, xylylene, a divalent acyl radical of an aliphatic, cycloaliphatic, araliphatic or aromatic dicarboxylic acid or of a dicarbamic acid, or R 2 is a group wherein D 1 and D 2 independently are hydrogen, an alkyl radical containing up to 8 carbon atoms, phenyl, benzyl or 3,5-di-t-butyl-4-hydroxybenzyl, and D 3 is an alkyl or alkenyl radical containing up to 18 carbon atoms; when m is 3, R 2 is a trivalent acyl radical of an aliphatic, cycloaliphatic, or aromatic tricarboxylic acid; when m is 4, R 2 is a tetravelent acyl radical of a saturated or unsaturated aliphatic or aromatic tetracarboxylic acid: p is 1, 2 or 3, R 3 is hydrogen, C 1 -C 12 alkyl, C 5 -C 7 cycloalkyl, C 7 -C 9 aralkyl, C 2 -C 18 alkanoyl, C 3 -Cs alkenoyl or benzoyl; when p is 1, R 4 is hydrogen, C 1 -C 18 alkyl, C 5 -C 7 cycloalkyl, C 2 -C 8 alkenyl unsubstituted or substituted by a cyano, carbonyl or carbamide group, or it is aryl, aralkyl, glycidyl, a group of the formula -CH 2 -CH(OH)-Z or of the formula -CONH-Z wherein Z is hydrogen, methyl or phenyl; or R 4 is a group of the formula I or with h as 0 or 1; or R 3 and R 4 together are alkylene of 4 to 6 carbon atoms or 1-oxo alkylene or the divalent acyl radical of an aliphatic or aromatic 1,2- 1,3-dicarboxylic acid; when p is 2, R 4 is C 1 -C 12 alkylene, C 6 -C 12 arylene, xylylene, a -CH 2 CH(OH)-CH 2 group, or a group -CH 2 -CH(OH)-CH 2 -0-X-0-CH 2 -CH(OH)-CH 2 - wherein X is C 2 -Cio alkylene, C 6 -C 15 arylene or C 6 -C 12 cycloalkylene; or, provided that R 3 is not alkanoyl, alkenoyl or benzoyl, R 4 can also be a divalent acyl radical of an aliphatic, cycloaliphatic or aromatic dicarboxylic or dicarbamic acid, or can be the group -CO-; or R 4 is a group of formula II where T 8 and T 9 are independently hydrogen, alkyl of 1 to 18 carbon atoms, or T 8 and T 9 together are alkylene of 4 to 6 carbon atoms or 3-oxapentamethylene, preferably T 8 and T 9 together are 3-oxapentamethylene; when p is 3, R 4 is 2,4,6-triazinetriyl; n is 1 or 2 and when n is 1, Rs and R' 5 are independently C 1 -C 12 alkyl, C 2 -C 12 alkenyl, C 7 -C 12 aralkyl, or Rs is also hydrogen, or R 5 and R' 5 together are C 2 -C 8 alkylene or hydroxyalkylene or C 4 -C 22 acyloxyalkylene; when n is 2, R s and R's together are (-CH 2 ) 2 C(CH 2 -) 2 ; R 6 is hydrogen, C 1 -C 12 alkyl, allyl, benzyl, glycidyl or C 2 -C 6 alkoxyalkyl; when n is 1, R 7 is hydrogen, C 1 -C 12 alkyl, C 3 -Cs alkenyl, C 7 -C 9 aralkyl, C 5 -C 7 cycloalkyl, C 2 -C 4 hydroxyalkyl, C 2 -C 6 alkoxyalkyl, C 6 -C 10 aryl, glycidyl, a group of the formula -(CH 2 )t-COO-Q or of the formula -(CH 2 ) t -o-CO-Q wherein t is 1 or 2, and Q is Ci-C 4 alkyl or phenyl; or when n is 2, R 7 is C 2 -C 12 alkylene, C 6 -C 12 arylene a group -CH 2 CH(OH)-CH 2 -O-X-O-CH 2 --CH(OH)-CH 2 - wherein X is C 2 -Cio alkylene, C 6 -C 15 arylene or C 6 -C 12 cycloalkylene, or a group -CH 2 CH(OZ')CH 2 -(OCH 2 -CH(OZ')CH 2 ) 2 -wherein Z' is hydrogen, C 1 -C 18 alkyl, allyl, benzyl, C 2 -C 12 alkanoyl or benzoyl; Q 1 is -N(R 8 )- or -O-; E is C 1 -C 3 alkylene, the group -CH 2 -CH(R 9 )-O- wherein R 9 is hydrogen, methyl or phenyl, or E is the group -(CH 2 ) 3 -NH or a direct bond; R 10 is hydrogen or C 1 -C 18 alkyl; R 8 is hydrogen, C 1 -C 18 alkyl, C 5 -C 7 cycloalkyl, C 7 -C 12 aralkyl, cyanoethyl, C 6 -C 10 aryl, the group -CH 2 -CH(R 9 )-OH wherein R 9 has the meaning defined above; a group of the formula I or a group of the formula wherein G can be C 2 -C 6 alkylene or C 6 -C 12 arylene; or R 8 is a group -E-CO-NH-CH 2 -ORio; T 3 is ethylene or 1,2-propylene, or is the repeating structural unit derived from an alpha-olefin copolymer with an alkyl acrylate or methacrylate; k is 2 to 100; T 4 has the same meaning as R 4 when p is 1 or 2, T 5 is methyl, T 6 is methyl or ethyl, or T 5 and T 6 together are tetramethylene or pentamethylene; M and Y are independently methylene or carbonyl; T 7 is the same as R 7 ; T 10 and T 11 are independently alkylene of 2 to 12 carbon atoms, or T 11 is a group of formula II; e is 2, 3 or 4 and T 12 is a group -N(R 5 )-(CH 2 ) d -N(R 5 )-or -NH(CH 2 ) a - N (CH 2 ) b -N[(CH 2 ) c -N ] f H where a, b and are independently 2 or 3, d is 2 to 10 and f is 0 or 1; T 13 is the same as R 4 with the proviso that R 13 cannot be hydrogen when n is 1; E 1 and E 2 , being different, each are -CO- or -N(Es)-, where E 5 is hydrogen, C 1 -C 12 alkyl or C 4 -C 22 alkoxycarbonylalkyl; E 3 is hydrogen, alkyl of 1 to 30 carbon atoms, phenyl, naphthyl, said phenyl or said naphthyl substituted by chlorine or by alkyl of 1 to 4 carbon atoms, or phenylalkyl of 7 to 12 carbon atoms, or said phenylalkyl substituted by alkyl of 1 to 4 carbon atoms, E 4 is hydrogen, alkyl of 1 to 30 carbon atoms, phenyl, naphthyl or phenylalkyl of 7 to 12 carbon atoms, or E 3 and E 4 together are polymethylene of 4 to 17 carbon atoms, or said polymethylene substituted by up to four alkyl groups of 1 to 4 carbon atoms; R 2 of formula (N) is as previously defined when m is 1; G 1 is a direct bond, C 1 -C 12 alkylene, phenylene or -NH-G'-NH wherein G' is C 1 -C 12 alkylene.

Claim 4

A composition according to claim 2 which contains a compound of formulae A, B, D, J, K or M wherein R is hydrogen and T 5 and T 6 are methyl.

Claim 5

A composition according to claim 2 which contains a compound of formula A wherein R is hydrogen, R 1 is a group D-CO- and D is C 1 -C 12 alkyl, C 1 -C 4 alkoxy, phenyl, amino or amino monosubstituted by C 1 -C 12 alkyl or phenyl, m is 1, 2 or 4 and when m is 1, R 2 is an acyl radical of an aliphatic C 2 -C 18 carboxylic acid, of a cycloaliphatic C 6 -C 12 carboxylic acid or of an aromatic C 7 -C 15 carboxylic acid and when m is 2, R 2 is a divalent acyl radical of an aliphatic C 2 -C 18 dicarboxylic acid or of a cycloaliphatic or aromatic C 8 -C 14 dicarboxylic acid, or of an aliphatic, cycloaliphatic or aromatic C 8 -C 14 dicarbamic acid, or R 2 is a group wherein D 1 is Ci-C 8 alkyl or 3,5-di-tert.butyl-4-hydroxybenzyl and D 2 is D 1 or hydrogen and when m is 4, R 2 is a tetravalent acyl radical of a butane- or pentane-tetracarboxylic acid.

Claim 6

A composition according to claim 2 which contains a compound of formula B wherein R is hydrogen, R 1 is a group D-CO- and D is C 1 -C 12 alkyl, C 1 -C 4 alkoxy, phenyl, amino or amino monosubstituted by C 1 -C 12 alkyl or phenyl, p is 1 or 2, R 3 is hydrogen, C 1 -C 12 alkyl or C 2 -C 12 alkanoyl and when p is 1, R 4 is Ci-C 12 alkyl, C 5 -C 7 cycloalkyl or a group of formula I, and when p is 2, R 4 is C 2 -Ca alkylene, phenylene or xylylene, and if R 3 is not alkanoyl, R 4 may also be a divalent acyl residue of an aliphatic C 2 -C↑ o dicarboxylic acid or of an aromatic C 6 dicarboxylic acid or of an aliphatic or aromatic C 8 -C 15 dicarbamic acid.

Claim 7

A composition of claim 1, which contains di-(1-acetoxy-2,2,6,6-tetramethylpiperidin-4-yl)sebacate.

Claim 8

The composition of claim 3, which contains alpha,alpha'-(di-1-ethoxy-2,2,6,6-tetramethylpiperidin-4-yloxy)-p-xylene.

Claim 9

The composition of claim 3, containing 1,4-dibenzyloxy-2,2,6,6-tetramethylpiperidine.

Claim 10

The composition of claim 3, containing di-(1-benzyloxy-2,2,6,6-tetramethylpiperidin-4-yl) sebacate.

Claim 11

The composition of claim 3, containing 4-benzyloxy-1-ethoxy-2,2,6,6-tetramethylpiperidine.

Claim 12

The composition of claim 3, containing 1,4-di-(4-hydroxy-3,5-di-tertbutylbenzoyloxy)-2,2,6,6-tetramethylpiperidine.

Claim 13

The composition of claim 3, containing alpha,alpha'-(di-1-benzoyloxy-2,2,6,6-tetramethylpiperidin-4-yloxy)-p-xylene.

Claim 14

A coating composition according to claim 1, which is an ambient curable system based on an alkyd resin, thermoplastic acrylic resin, acrylic alkyd resin, polyurethane resin or polyester resin, or said resins modified with silicones, isocyanates, epoxides, isocyanurates, ketimines or oxazolidines, or the system is based on a cellulose ester or on an epoxide resin.

Claim 15

A coating composition according to claim 1, which is an acid catalyzed thermosetting system based on a hot crosslinkable acrylic, polyester, polyurethane, polyamide or alkyd resin.

Claim 16

The composition according to claim 1, which is an enamel for industrial finishes.

Claim 17

The composition according to claim 1, which is a refinishing enamel for automobiles.