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US 4,046,737 AGranted
Piperidine derivatives
AssigneeCiba-Geigy Corporation
InventorsBrian Holt, Donald Richard Randell
Life of this patent
Estimating the term…
Abstract
New 1- and 4-substituted piperidines are stabilizers for organic material. They are produced by reacting corresponding 1-substituted piperidinols with acid chlorides or corresponding 4-substituted piperidines with a compound introducing into the 1-position a residue.
Claims16
A composition comprising an organic material and 0.01% to 5% by weight of a stabilizer having the formula ##STR155## and their salts wherein n is 1, 2, 3 or 4;
- R.sub.1 is a monovalent residue and is an alkyl residue from 1 to 20 carbon atoms, an alkenyl or alkynyl residue having from 3 to 20 carbon atoms, an aralkyl residue having from 7 to 12 crbon atoms, or a residue having the formula:
- ##STR156## wherein m is 1, 2 or 3, R.sub.4 is a hydrogen, methyl or phenyl residue,
- X.sub.2 is halogen, cyano, ##STR157## --COR.sub.5, --C0.0R.sub.5, --CO.SR.sub.5 --, or --CONR.sub.5 R.sub.6 and
- X.sub.1 is hydroxyl, halogen, cyano, ##STR158## where R.sub.5 is an alkyl residue having from 1 to 20 carbon atoms, an alkenyl residue having from 2 to 20 carbon atoms, a cycloalkyl residue having from 5 to 12 carbon atoms, an aryl residue having from 6 to 11 carbon atoms or an aralkyl residue having 7 to 14 carbon atoms or when R.sub.5 is joined to a nitrogen atom, also hydrogen and
- R.sub.6 is hydrogen or an alkyl residue having from 1 to 4 carbon atoms, or
- R.sub.5 and R.sub.6 together with the nitrogen atom to which they are bound form a 5- or 6-membered ring which contains no other heteroatoms or contains one or more other heteroatoms, or R.sub.1 is an acyl group ##STR159## where R.sub.7 is hydrogen, an unsubstituted aliphatic or substituted aliphatic residue having from 1 to 20 carbon atoms, an alkenyl or alkynyl residue having from 2 to 20 carbon atoms, a cycloaliphatic residue having from 5 to 12 carbon atoms, an araliphatic residue having from 7 to 14 carbon atoms, an aromatic residue having from 6 to 20 carbon atoms or an heterocyclic residue, or
- R.sub.1 is a carbamoyl or thiocarbamoyl residue having the formula:
- ##STR160## wherein X.sub.3 is --O-- or --S--, R.sub.8 is hydrogen or an alkyl residue having from 1 to 4 carbon atoms, and
- R.sub.9 is hydrogen, an alkyl residue having from 1 to 20 carbon atoms, an alkenyl residue having from 3 to 20 carbon atoms, a cycloalkyl residue having from 5 to 12 carbon atoms or an unsubstituted aryl or substituted aryl residue having from 6 to 12 carbon atoms;
- R.sub.2 is an alkyl residue having from 1 to 4 carbon atoms, an alkenyl or alkynyl residue having 3 to 20 carbon atoms, a cycloalkyl residue having from 5 to 12 carbon atoms, an aryl residue having from 6 to 11 carbon atoms or an aralkyl residue having from 7 to 9 carbon atoms or hydrogen;
- and
- when n is 1, R.sub.3 is a monovalent residue and is an alkyl residue having from 1 to 20 carbon atoms, a cycloalkyl residue having from 5 to 12 carbon atoms, an alkenyl or alkynyl residue hving from 3 to 20 carbon atoms, an aralkyl residue having from 7 to 12 carbon atoms, or a residue having the formula:
- ##STR161## wherein m is 1, 2 or 3, R.sub.4 is a hydrogen, methyl or phenyl residue,
- X.sub.2 is halogen, cyano, ##STR162## --COR.sub.5, --CO.OR.sub.5, --CO.SR.sub.5, or CONR.sub.5 R.sub.6 and
- X.sub.1 is hydroxyl, halogen, cyano, ##STR163## wherein R.sub.5 is an alkyl residue having from 1 to 20 carbon atoms, an alkenyl residue having from 2 to 20 carbon atoms, a cycloalkyl residue having from 5 to 12 carbon atoms, an aryl residue having from 6 to 11 carbon atoms or an aralkyl residue having 7 to 14 carbon atoms, or when
- R.sub.5 is joined to a nitrogen atom, also hydrogen and
- R.sub.6 is hydrogen or an alkyl residue having from 1 to 4 carbon atoms, or
- R.sub.5 and R.sub.6 together with the nitrogen atom to which they are bound form a 5- or 6-membered ring which contains no other heteroatoms or contains one or more other heteroatoms, or
- R.sub.3 is an acyl group, ##STR164## wherein R.sub.7 is hydrogen, an unsubstituted aliphatic or substitued aliphatic residue having from 1 to 20 carbon atoms, an alkenyl or alkynyl residue having from 2 to 20 carbon atoms, a cycloaliphatic residue having from 5 to 12 carbon atoms, an araliphatic residue having from 7 to 14 carbon atoms, an aromatic residue having from 6 to 20 carbon atoms or an heterocyclic residue, or
- R.sub.3 is a carbamoyl or thiocarbamoyl residue having the formula:
- ##STR165## wherein X.sub.3 is --O-- or --S--, R.sub.8 is hydrogen or an alkyl residue having from 1 to 4 carbon atoms, and
- R.sub.9 is hydrogen, an alkyl residue having from 1 to 20 carbon atoms, an alkenyl residue having from 3 to 20 carbon atoms, a cycloalkyl residue having from 5 to 12 carbon atoms or an unsubstituted aryl or substituted aryl residue having from 6 to 12 carbon atoms;
- or
- R.sub.3 represents a monovalent group obtained by removing a hydroxyl group from a sulphinic acid, a sulphonic acid, a phosphorus containing acid or a boric acid, or
- R.sub.3 is an aryl residue or a residue having the formula:
- ##STR166## wherein R.sub.1 ' is hydrogen or R.sub.1 ' has the same significance as R.sub.1 :
- when n is 2, R.sub.3 is a divalent residue and is an aklkylene residue having from 1 to 20 carbon atoms, an alkenylene residue having from 2 to 20 carbon atoms, an alkynylene residue having from 2 to 20 carbon atoms, a cycloalkyliden residue having from 5 to 12 carbon atoms, an arylene residue having 6 to 14 carbon atoms, an aralkylene residue having from 8 to 14 carbon atoms or an aliphatic, aromatic or heterocyclic diacyl residue, the group --Co-- or --CO.CO--, an aliphatic or aromatic dicarbomoyl or dithiocarbamoyl, sulphinyl or sulponyl residue or a divalent residue obtained by removing two hydroxyl groups from a disulphonic acid, a phosphorus containing acid or a boric acid;
- when n is 3, R.sub.3 is a trivalent residue and is an alkanetriyl, an arenetriyl or an arenetriyl-trialkylene residue, an aliphatic or aromatic triacyl residue or a triacyl residue derived from o-phosphoric, o-phosphorous or o-boric and
- when n is 4, R.sub.3 is a tetravalent residue and is an alkanetetrayl residue or a tetraacyl residue derived from an aliphatic or aromatic tetracarboxylic acid or from o-silicic acid as well as, when n is 2, 3 or 4, partial ethers, esters and carbamoyloxy and thiocarbamoyloxy compounds related to the fully reacted compounds of formula I;
- provided that when a compound of formula I is an ester, the alkyl group of R.sub.1 has only 5 to 20 carbon atoms.
27 more elements
Dependencies are inferred from the claim text.