US 2003/0166939 A1 · 2,2,6,6 diethyl-dimethyl-1-alkoxy-piperidine compounds and their corresponding 1-oxides

Abstract

The present invention relates to selected 1-alkoxy-2,2 diethyl-6,6 dimethyl piperidine and 1-alkoxy-2,6 diethyl-2,3,6 trimethyl piperidine derivatives which are substituted in the 4 position by an oxygen or nitrogen atom; a polymerizable composition comprising a) at least one ethylenically unsaturated monomer and b) said piperidine derivatives. Further aspects of the present invention are a process for polymerizing ethylenically unsaturated monomers, and the use of 1-alkoxy-2,2 diethyl-6,6 dimethyl piperidine and 1-alkoxy-2,6 diethyl-2,6 dimethyl piperidine derivatives which are substituted in the 4 position by an oxygen or nitrogen atom for controlled polymerization. The intermediate N-oxyl derivatives, a composition of the N-oxyl derivatives with ethylenically unsaturated monomers and a free radical initiator, as well as a process for polymerization are also subjects of the present invention.

Claims19

Dependent claims

A compound according to formula Ia or IIa

65
wherein
Y is a radical
66
R1 is hydrogen, —COOH, —COO(C1-C4alkyl), —COO-phenyl, —COObenzyl, C1-C8alkoxy, C1-C18alkyl, C2-C4alkenyl, C1-C18alkyl or C2-C4alkenyl substituted by OH, —COOH, —COO(C1-C4)alkyl, C2-C18alkyl which may be interrupted by one or more oxygen atom, unsubstituted cyclopentyl, cyclohexyl, cyclohexenyl, phenyl or naphthyl;
or cyclopentyl, cyclohexyl, cylohexenyl, phenyl or naphthyl which are substituted by C1-C4alkyl, —COOH or —COO—(C1-C4alkyl)
R2 is hydrogen, C1-C18alkyl or R1 and R2 together with the nitrogen atom form a 5-membered ring which may have an unsaturated bond or be fused to a benzene ring;
R3 is hydrogen or C1-C18alky;
and
X is selected from the group consisting of —(C5-C12)-3-cycloalkenyl, —CH2-phenyl, CH3CH-phenyl, (CH3)2C-phenyl, (C5-C6cycloalkyl)2 CCN, (CH3)2CCN, —CH2CH═CH2, CH3CH—CH═CH2 (C1-C4alkyl)CR20—C(O)-phenyl, (C1-C4)alkyl-CR20—C(O)—(C1-C4)alkoxy, (C1-C4)alkyl-CR20—C(O)—(C1-C4)alkyl, (C1-C4)alkyl-CR20—C(O)-n-di(C1-C4)alkyl, (C1-C4)alkyl-CR20—C(O)—NH(C1-C4)alkyl, (C1-C4)alkyl-CR20—C(O)—NH2, wherein R20 is hydrogen or (C1-C4)alkyl;
with the proviso that benzoic acid 2,6-diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl ester is excluded.

8 more elements

A compound selected from the group consisting of

(1) Formic acid 2,6-diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl ester;
(2) Acetic acid 2,6-diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl ester;
(3) Propionic acid 2,6-diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl ester;
(4) Butyric acid 2,6-diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl ester;
(5) Pentanoic acid 2,6-diethyl-2,3,6-trimethyl-1-(i-phenyl-ethoxy)-piperidin-4-yl ester;
(6) Hexanoic acid 2,6-diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl ester,
(7) Heptanoic acid 2,6-diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl ester;
(8) Octanoic acid 2,6-diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl ester;
(9) Nonanoic acid 2,6-diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl ester;
(10) Decanoic acid 2,6-diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl ester;
(11) Undecanoic acid 2,6-diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl ester;
(12) Dodecanoic acid 2,6-diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl ester;
(13) Tridecanoic acid 2,6-diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl ester;
(14) Tetradecanoic acid 2,6-diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl ester;
(15) Pentadecanoic acid 2,6-diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl ester;
(16) Hexadecanoic acid 2,6-diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl ester;
(17) Heptadecanoic acid 2,6-diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl ester;
(18) Octadecanoic acid 2,6-diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl ester,
(19) Carbonic acid 2,6-diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl ester methyl ester;
(20) Carbonic acid 2,6-diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl ester ethyl ester;
(21) Carbonic acid benzyl ester 2,6-diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl ester;
(22) Carbonic acid .tert.-butyl ester 2,6-diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl ester;
(23) Oxalic acid 2,6-diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl ester methyl ester;
(24) Succinic acid mono-[2,6-diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]ester;
(25) Succinic acid 2,6-diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl ester methyl ester;
(26) But-2-enedioic acid mono-[2,6-diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]ester;
(27) But-2-enedioic acid 2,6-diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl ester methyl ester;
(28) Pentanedioic acid mono-[2,6-diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]ester;
(29) Pentanedioic acid 2,6-diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl ester methyl ester
(30) Hexanedioic acid mono-[2,6-diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]ester;
(31) Hexanedioic acid 2,6-diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl ester methyl ester;
(32) Cyclohexanecarboxylic acid 2,6-diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl ester;
(33) Cyclohex-3-enecarboxylic acid 2,6-diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl ester;
(34) Benzoic acid 2,6-diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl ester;
(35) Terephthalic acid 1-[2,6-diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]ester 4-methyl ester;
(36) Isophthalic acid 1-[2,6-diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]ester 3-methyl ester;
(37) Phthalic acid mono-[2,6-diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]ester;
(38) Naphthalene-1-carboxylic acid 2,6-diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl ester;
(39) Acrylic acid 2,6-diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl ester;
(40) 2-Methyl-acrylic acid 2,6-diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl ester;
(41) Methyl-carbamic acid 2,6-diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-yl ester;
(42) Ethyl-carbamic acid 2,6-diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl ester;
(43) Isopropyl-carbamic acid 2,6-diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4yl ester;
(44) Octadecyl-carbamic acid 2,6-diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl ester;
(45) Cyclohexyl-carbamic acid 2,6-diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl ester;
(46) Phenyl-carbamic acid 2,6-diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl ester;
(47) p-Tolyl-carbamic acid 2,6-diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl ester;
(48) Naphthalen-1-yl-carbamic acid 2,6-diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl ester;
(49) Dimethyl-carbamic acid 2,6-diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl ester;
(50) 2,6-Diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-ylamine;
(51) N-[2,6-Diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-formamide;
(52) N-[2,6-Diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-acetamide;
(53) N-[2,6-Diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-propionamide;
(54) N-[2,6-Diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-butyramide;
(55) Pentanoic acid [2,6-diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-amide;
(56) Hexanoic acid [2,6-diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-amide;
(57) Heptanoic acid [2,6-diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-amide;
(58) Octanoic acid [2,6-diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-amide;
(59) Nonanoic acid [2,6-diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-amide;
(60) Decanoic acid [2,6-diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-amide;
(61) Undecanoic acid [2,6-diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-amide;
(62) Dodecanoic acid [2,6-diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-amide;
(63) Tridecanoic acid [2,6-diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-amide;
(64) Tetradecanoic acid [2,6-diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-amide;
(65) Pentadecanoic acid [2,6-diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-amide;
(66) Hexadecanoic acid [2,6-diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-amide;
(67) Heptadecanoic acid [2,6-diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-amide;
(68) Octadecanoic acid [2,6-diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-amide;
(69) [2,6-Diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-carbamicacidmethyl ester;
(70) [2,6-Diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-carbamic acid ethyl ester;
(71) [2,6-Diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-carbamic acid benzyl ester;
(72) [2,6-Diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-carbamic acid .tert.-butyl ester;
(73) N-[2,6-Diethyl-2,3,6-trimethyl-1 (1-phenyl-ethoxy)-piperidin-4-yl]-oxalamic acid;
(74) N-[2,6-Diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]oxalamic acid methyl ester;
(75) N-[2,6-Diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-succinamic acid;
(76) N-[2,6-Diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-succinamic acid methyl ester;
(77) 3-[2,6-Diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-ylcarbamoyl]-acrylic acid;
(78) 3-[2,6-Diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-ylcarbamoyl]-acrylic acid methyl ester;
(79) 4-[2,6-Diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-ylcarbamoyl]-butyric acid;
(80) 4-[2,6-Diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-ylcarbamoyl]-butyric acid methyl ester;
(81) 5-[2,6-Diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-ylcarbamoyl]-pentanoic acid;
(82) 5-[2,6-Diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-ylcarbamoyl]-pentanoic acid methyl ester;
(83) N-[2,6-Diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-4-hydroxy-butyramide;
(84) 6-Hydroxy-hexanoic acid [2,6-diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-amide;
(85) Cyclohexanecarboxylic acid [2,6-diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-amide;
(86) Cyclohex-3-enecarboxylic acid [2,6-diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-amide;
(87) N-[2,6-Diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-benzamide;
(88) N-[2,6-Diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-terephthalamic acid methyl ester;
(89) N-[2,6-Diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-isophthalamic acid methyl ester;
(90) N-[2,6-Diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-phthalamic acid
(91) Naphthalene-1-carboxylic acid [2,6-diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-amide;
(92) N-[2,6-Diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-acrylamide;
(93) N-[2,6-Diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-2-methyl-acrylamide;
(94) N-Butyl-N-[2,6-diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]acetamide
(95) [2,6-Diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-urea;
(96) 1-[2,6-Diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-3-methyl-urea;
(97) 1-[2,6-Diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-3-ethyl-urea;
(98) 1-[2,6-Diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-3-isopropyl-urea;
(99) 1-[2,6-Diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-3-octadecyl-urea;
(100)1-Cyclohexyl-3-[2,6-diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-urea;
(101)1-[2,6-Diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-3-phenyl-urea;
(102)1-[2,6-Diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-3-.p.-tolyl-urea;
(103)1-[2,6-Diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-3-naphthalen-1-yl-urea;
(104) 3-[2,6-Diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-1,1-dimethyl-urea;
(105) 1-Butyl-1-[2,6-diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-3-phenyl-urea;
(106)1-[2,6-Diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-pyrrolidine-2,5-dione;
(107) 1-[2,6-Diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-pyrrole-2,5-dione;
(108)1-[2,6-Diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-3,4-dimethyl-pyrrole-2,5-dione;
(109) 2′,6′-Diethyl-2′,3′,6′-trimethyl-1′-(1-phenyl-ethoxy)-[1,4′]bipiperidinyl-2,6-dione;
(110) 2-[2,6-Diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-isoindole-1,3-dione;
(111) 2-[2,6-Diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-1,3-dioxo-2,3-dihydro-1.H.-isoindole-5-carboxylic acid.

108 more elements

A compound selected from the group consisting of

(1) Formic acid 2,2-diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl ester;
(2) Acetic acid 2,2-diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl ester;
(3) Propionic acid 2,2-diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl ester;
(4) Butyric acid 2,2-diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl ester;
(5) Pentanoic acid 2,2-diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl ester;
(6) Hexanoic acid 2,2-diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl ester,
(7) Heptanoic acid 2,2-diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl ester;
(8) Octanoic acid 2,2-diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl ester;
(9) Nonanoic acid 2,2-diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl ester;
(10) Decanoic acid 2,2-diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl ester;
(11) Undecanoic acid 2,2-diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl ester,
(12) Dodecanoic acid 2,2-diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl ester;
(13) Tridecanoic acid 2,2-diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl ester;
(14) Tetradecanoic acid 2,2-diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl ester;
(15) Pentadecanoic acid 2,2-diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl ester;
(16) Hexadecanoic acid 2,2-diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl ester;
(17) Heptadecanoic acid 2,2-diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl ester;
(18) Octadecanoic acid 2,2-diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl ester;
(19) Carbonic acid 2,2-diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl ester methyl ester;
(20) Carbonic acid 2,2-diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl ester ethyl ester;
(21) Carbonic acid benzyl ester 2,2-diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl ester;
(22) Carbonic acid .tert.-butyl ester 2,2-diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl ester;
(23) Oxalic acid 2,2-diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl ester methyl ester;
(24) Succinic acid mono-[2,2-diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]ester;
(25) Succinic acid 2,2-diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl ester methyl ester;
(26) But-2-enedioic acid mono-[2,2-diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]ester;
(27) But-2-enedioic acid 2,2-diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl ester methyl ester;
(28) Pentanedioic acid mono-[2,2-diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]ester;
(29) Pentanedioic acid 2,2-diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl ester methyl ester;
(30) Hexanedioic acid mono-[2,2-diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]ester;
(31) Hexanedioic acid 2,2-diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl ester methyl ester;
(32) Cyclohexanecarboxylic acid 2,2-diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl ester;
(33) Cyclohex-3-enecarboxylic acid 2,2-diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl ester;
(34) Terephthalic acid 1-[2,2-diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]ester 4-methyl ester;
(35) Isophthalic acid 1-[2,2-diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]ester 3-methyl ester;
(36) Phthalic acid mono-[2,2-diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]ester;
(37) Naphthalene-1-carboxylic acid 2,2-diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-yl ester;
(38) Acrylic acid 2,2-diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl ester;
(39) 2-Methyl-acrylic acid 2,2-diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl ester;
(40) Methyl-carbamic acid 2,2-diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl ester;
(41) Ethyl-carbamic acid 2,2-diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl ester;
(42) Isopropyl-carbamic acid 2,2-diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl ester;
(43) Octadecyl-carbamic acid 2,2-diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl ester;
(44) Cyclohexyl-carbamic acid 2,2-diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl ester;
(45) Cyclohexyl-carbamic acid 2,2-diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-yl ester;
(46) p-Tolyl-carbamic acid 2,2-diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl ester;
(47) Naphthalen-1-yl-carbamic acid 2,2-diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl ester;
(48) Dimethyl-carbamic acid 2,2-diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl ester;
(49) 2,2-Diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-ylamine;
(50) N-[2,2-Diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-formamide;
(51) N-[2,2-Diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-acetamide;
(52) N-[2,2-Diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-propionamide;
(53) N-[2,2-Diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]butyramide;
(54) Pentanoic acid [2,2-diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-amide;
(55) Hexanoic acid [2,2-diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-amide;
(56) Heptanoic acid [2,2-diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-amide;
(57) Octanoic acid [2,2-diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-amide;
(58) Nonanoic acid [2,2-diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-amide;
(59) Decanoic acid [2-ethyl-2,6,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-amide;
(60) Undecanoic acid [2,2-diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-amide;
(61) Dodecanoic acid [2,2-diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-amide;
(62) Tridecanoic acid [2,2-diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-amide;
(63) Tetradecanoic acid [2,2-diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-amide;
(64) Pentadecanoic acid [2,2-diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-amide;
(65) Pentadecanoic acid [2,2-diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-amide;
(66) Hexadecanoic acid [2,2-diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-amide;
(67) Heptadecanoic acid [2,2-diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-amide;
(68) [2,2-Diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-carbamic acid methyl ester;
(69) [2,2-Diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-carbamic acid ethyl ester;
(70) [2,2-Diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-carbamic acid benzyl ester;
(71) [2,2-Diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-carbamic acid .tert.-butyl ester;
(72) N-[2,2-Diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-oxalamic acid;
(73) N-[2,2-Diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-oxalamic acid methyl ester;
(74) N-[2,2-Diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-succinamic acid;
(75) N-[2,2-Diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-succinamic acid methyl ester;
(76) 3-[2,2-Diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-ylcarbamoyl]-acrylic acid;
(77) 3-[2,2-Diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-ylcarbamoyl]-acrylic acid methyl ester
(78) 4-[2,2-Diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-ylcarbamoyl]-butyric acid;
(79) 4-[2,2-Diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-ylcarbamoyl]-butyric acid methyl ester;
(80) 5-[2,2-Diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-ylcarbamoyl]-pentanoic acid;
(81) 5-[2,2-Diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-ylcarbamoyl]-pentanoic acid methyl ester;
(82) N-[2,2-Diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-4-hydroxy-butyramide;
(83) 6-Hydroxy-hexanoic acid [2,2-diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-amide;
(84) Cyclohexanecarboxylic acid [2,2-diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-amide;
(85) Cyclohex-3-enecarboxylic acid [2,2-diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-amide;
(86) N-[2,2-Diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]benzamide;
(87) N-[2,2-Diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-terephthalamic acid methyl ester;
(88) N-[2,2-Diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-isophthalamic acid methyl ester;
(89) N-[2,2-Diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-phthalamic acid;
(90) Naphthalene-1-carboxylic acid [2,2-diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-amide;
(91) N-[2,2-Diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-acrylamide;
(92) N-[2,2-Diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-2-methyl-acrylamide;
(93) N-Butyl-.N.-[2,2-diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-acetamide
(94) [2,2-Diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-urea;
(95) 1-[2,2-Diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-3-methyl-urea;
(96) 1-Ethyl-3-[2-ethyl-2,6,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-urea;
(97) 1-[2,2-Diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-3-isopropyl-urea;
(98) 1-[2,2-Diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-3-octadecyl-urea;
(99) 1-Cyclohexyl-3-[2,2-diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-urea;
(100) 1-[2,2-Diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-3-phenyl-urea;
(101) 1-[2,2-Diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-3-.p.-tolyl-urea;
(102) 1-[2,2-Diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-3-naphthalen-1-yl-urea;
(103) 3-[2,2-Diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-1,1-dimethyl-urea;
(104) 1-Butyl-1-[2,2-diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-3-phenyl-urea;
(105) 1-[2,2-Diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-pyrrolidine-2,5-dione;
(106) 1-[2,2-Diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-pyrrole-2,5-dione;
(107) 1-[2,2-Diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-3,4-dimethyl-pyrrole-2,5-dione;
(108) 2′,2′-Diethyl-6′,6′-dimethyl-1′-(1-phenyl-ethoxy)-[1,4′]bipiperidinyl-2,6-dione;
(109) 2-[2,2-Diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-isoindole-1,3-dione;
(110) 2-[2,2-Diethyl-6,6-dimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-1,3-dioxo-2,3-dihydro-1H-isoindole-5-carboxylic acid.

107 more elements

A polymerizable composition, comprising

a) at least one ethylenically unsaturated monomer or oligomer, and
b) a compound of formula Ia or IIa.
69
wherein
Y is a radical
70
R1 is hydrogen, —COOH, —COO(C1-C4alkyl), —COO-phenyl, —COObenzyl, C1-C8alkoxy, C1-C18alkyl, C2-C4alkenyl, C1-C18alkyl or C2-C4alkenyl substituted by OH, —COOH, —COO(C1-C4)alkyl, C2-C18alkyl which may be interrupted by one or more oxygen atom, unsubstituted cyclopentyl, cyclohexyl, cyclohexenyl, phenyl or naphthyl;
or cyclopentyl, cyclohexyl, cylohexenyl, phenyl or naphthyl which are substituted by C1-C4alkyl, —COOH or —COO—(C1-C4alkyl)
R2 is hydrogen, C1-C18alkyl or R1 and R2 together with the nitrogen atom form a 5-membered ring which may have an unsaturated bond or be fused to a benzene ring;
R3 is hydrogen or C1-C18alky;
and
X is selected from the group consisting of —(C15-C12)-3-cycloalkenyl, —CH2-phenyl, CH3CH-phenyl, (CH3)2C-phenyl, (C5-C6cycloalkyl)2CCN, (CH3)2CCN, —CH2CH═CH2, CH3CH—CH═CH2 (C1-C4alkyl)CR20—C(O)-phenyl, (C1-C4)alkyl-CR20—C(O)—(C1-C4)alkoxy, (C1-C4)alkyl-CR20—C(O)—(C1-C4)alkyl, (C1-C4)alkyl-CR20—C(O)—N-di(C1-C4)alkyl, (C1-C4)alkyl-CR20—C(O)—NH(C1-C4)alkyl, (C1-C4)alkyl-CR20—C(O)—NH2, wherein R20 is hydrogen or (C1-C4)alkyl;
with the proviso that benzoic acid 2,6-diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl ester is excluded.

10 more elements

Dependencies are inferred from the claim text.

2,2,6,6 diethyl-dimethyl-1-alkoxy-piperidine compounds and their corresponding 1-oxides

Life of this patent

2,2,6,6 diethyl-dimethyl-1-alkoxy-piperidine compounds and their corresponding 1-oxides

Life of this patent

Abstract

Claims19