Ciba-geigy Corporation

Ciba Specialty Chemicals Corporation

Basf Se Corporation

Hugo Camenzind

Paul Dubs

Peter Nesvadba

Alfred Dratva

Samuel Evans

Emyr Phillips

Roger Martin

Kay S Groninger

Peter H&auml;nggi

Robert M O'Neil

Andreas Mühlebach

David Eliezer Chasan

Rolf Schumacher

Marc Ribeaud

John David Payne

François Rime

Peter Rohrbach

Peter Hänggi

Michael Fletschinger

James Robbins

Gunnar Demme

Miles Hutchings

The present invention relates to a block copolymer prepared by ATRP, wherein the polymer chain terminal group is structurally modified with the functionally effective group of a lubricant or polymer additive selected from the group consisting of antioxidants, metal deactivators, antiwear and extreme pressure additives and corrosion inhibitors. The invention also relates to a composition comprising the structurally modified block copolymer and a composition of matter subject to oxidative, thermal or light induced degradation, such as lubricants or polymers.

Polymers produced by atom transfer radical polymerisation technique with structurally modified terminal groups

The invention relates to liquid sulphur-containing antioxidants and to compositions comprising them. The novel lubricant compositions comprise the reaction product of a selected group of 5-tert-butyl-4-hydroxy-3-methyl(or tert-butyl)phenyl substituted carboxylic acid esters with thiodiethylene glycol and a mono-hydroxy alcohol with a carbon chain length higher than 4 C-atoms. The novel lubricant compositions are highly resistant to oxidative degradation and are capable of reducing the negative effects of deposits, such as black sludge, in motor combustion engines, particularly spark ignition internal combustion engines.

Liquid phenolic sulphur-containing antioxidants

Heterocyclic thioethers as additives for lubricants

Suitable lubricant additives are the compounds of formulae

Phosphorus-free multifunctional additives for lubricants

This invention relates to compounds which are suitable as ash-free antiwear additives and antioxidants, to lubricant compositions comprising said compounds as well as to their use. Compounds of formulae ##STR1## are particularly preferred. In the preferred compounds I',

Described are products suitable as lubricant and fuel additives which are obtainable by reacting a polyunsaturated polymer, for example polybutadiene, polyisoprene, ring-opening polymerised polycyclooctenamer or polynorbomene, with at least one enophilic compound of the groups of the dihydrocarbyidithiophosphoric acids, dihydrocarbylmonothiophosphoric acids, dihydrocarbylphosphoric acids or mercaptans.

Polymeric multifunctional lubricant additives

Suitable lubricant additives are the compounds of formulae wherein the substituents and groups have the following preferred meanings:

Benzothiazolylthio or thiadiazolylthio substituted phenols as

A description is given of compositions comprising

.beta.-dithiophosphorylated porpionic acid in lubricants

The instant invention relates to novel compounds of formula (II) ##STR1## wherein R, R.sup.2 and x are as defined in the Specification. These compounds retard oxidation of, confer protection under extreme pressures to and reduce frictional wear of lubricants and hydraulic fluids.

Thiocarbonyl allophanate derivatives used as lubricants

Products are described which can be obtained by reacting components a), b), c) and d), where component a) is a compound of the formula I or a mixture of compounds of the formula I, component b) is a compound of the formula II or a mixture of compounds of the formula II, component c) is a compound of the formula III or a mixture of compounds of the formula III and component d) is a compound of the formula IV or a mixture of compounds of the formula IV, ##STR1## in which the general symbols are as defined in claim 1, the compound of the formula I being, for example, pentaerythritol, thiodiethylene glycol, 1,4-butanediol, 1,2-propanediol, diethylene glycol, triethylene glycol, diethanolamine or glycerol, the compound of the formula II being, for example, sunflower oil or coconut fat, the compound of the formula III being, for example, methyl 3-(3',5'-di-tert-butyl-4'-hydroxyphenyl)propionate and the compound of the formula IV, being for example, sulfur or diisopropyl dithiophosphate. The abovementioned products can be used as liquid antioxidants in polymers and lubricants.

Liquid antioxidants as stabilizers

New compounds of the formula I are described which are active, for example, as antioxidants, and also a process for their preparation: ##STR1## R.sub.1 and R.sub.2 are independently of one another C.sub.1 -C.sub.20 alkyl, allyl, methallyl, unsubstituted or C.sub.1 -C.sub.8 alkyl-substituted C.sub.5 -C.sub.12 cycloalkyl, C.sub.5 -C.sub.8 cycloalkenyl, phenyl or C.sub.7 -C.sub.9 phenylalkyl, A is a direct bond, --CH.sub.2 --, --(CH.sub.2).sub.2 -- or --CH.sub.2 --CH(CH.sub.3)--, E is --(CH.sub.2).sub.2 --, --CHR.sub.6 --CH.sub.2 -- or --CH.sub.2 CHR.sub.6 --, n is 1, 2 or 3, R.sub.3 is C.sub.1 -C.sub.18 alkyl or is C.sub.1 -C.sub.18 alkyl which is interrupted by --O-- or --S--, unsubstituted or C.sub.1 -C.sub.8 alkyl-substituted C.sub.5 -C.sub.12 cycloalkyl, phenyl, naphthyl, C.sub.7 -C.sub.9 phenylalkyl, C.sub.7 -C.sub.18 alkylphenyl or is of the formula ##STR2## R.sub.4 is phenyl, naphthyl, C.sub.7 -C.sub.9 phenylalkyl, C.sub.7 -C.sub.18 alkylphenyl or is a radical of the formula ##STR3## or NR.sub.3 R.sub.4 is a group of the formula ##STR4## R.sub.5 is hydrogen, C.sub.1 -C.sub.18 alkyl, allyl, methallyl, unsubstituted or C.sub.1 -C.sub.8 alkyl-substituted C.sub.5 -C.sub.12 cycloalkyl, phenyl or naphthyl, R.sub.6 is hydrogen, C.sub.1 -C.sub.20 alkyl or C.sub.2 -C.sub.20 alkyl which is interrupted by --O--, --S--, --NR.sub.7 -- or --C(O)O--, and R.sub.7 is hydrogen or C.sub.1 -C.sub.6 alkyl.

(Di)arylaminoalkyl 4-hydroxyphenylalkanecarboxylates

Lubricant composition

The invention relates to novel compounds of formula I ##STR1## n is 1 or 2,

Phosphorus-free lubricant additives

The invention relates to novel compounds of formulae I, II and III ##STR1## wherein R.sub.1 is hydrogen, C.sub.1 -C.sub.20 alkyl or C.sub.5 -C.sub.7 cycloalkyl, R.sub.2 is hydrogen, C.sub.1 -C.sub.20 alkyl or C.sub.5 -C.sub.7 cycloalkyl, and R.sub.3 is C.sub.1 -C.sub.18 alkyl or C.sub.3 -C.sub.18 alkenyl. The compounds are used as antiwear additives for lubricants.

Dithiophosphates as antiwear additives

Novel compounds of the formula (I) ##STR1## in which X is oxygen or sulfur, R and R.sub.1 independently of one another are C.sub.3 -C.sub.30 alkyl, R.sub.2 is C.sub.4 -C.sub.18 alkyl and R.sub.3, R.sub.4, R.sub.5 and R.sub.6 independently of one another are H, C.sub.1 -C.sub.20 alkyl, C.sub.3 -C.sub.20 alkenyl, benzyl, phenyl or phenyl which is substituted by C.sub.1 -C.sub.12 alkyl, and in which R.sub.5 and R.sub.6 can also be a direct bond, or R.sub.3 and R.sub.4 together are trimethylene, tetramethylene, ##STR2## and R.sub.5 and R.sub.6 are a direct bond or H, or in each case R.sub.3 and R.sub.6 together are a group .dbd.CH.sub.2 and R.sub.4 and R.sub.5 are H, or R.sub.4 and R.sub.5 together are a group .dbd.CH.sub.2 and R.sub.3 and R.sub.6 are H, or R.sub.3, R.sub.4, R.sub.5 and R.sub.6 together are ##STR3## and salts of these compounds, are described. They can be employed as multipurpose additives, in particular as anticorrosion, high pressure and antiwear additives, and as antioxidants in the lubricants and hydraulic or metalworking fluids.

Growing community of inventors

Bern, Switzerland

Hugo Camenzind