Ciba-geigy Corporation

Siegfried Rosenberger

Andreas Schmidt

Kurt Schwarzenbach

Samuel Evans

Heimo Brunetti

Helmut Muller

Michael Rasberger

Hans-Rudolf Meier

Bernard Gilg

Werner Stegmann

Helmut Mueller

The phenol-mercaptocarboxylic acid esters used for stabilizing elastomers are those of the formula ##STR1## wherein R is C.sub.1 -C.sub.18 alkyl.

Use of phenol-mercaptocarboxylic acid esters as stabilizers for

Compounds of the formula I ##STR1## in which n is 1, 2 or 3, R.sup.1 is C.sub.1 -C.sub.5 -alkyl, cyclohexyl or .alpha.-methylcyclohexyl and, if n is 1, X is a group of the formula II or III ##STR2## in which R.sup.2 and R.sup.3 independently of one another are C.sub.1 -C.sub.8 -alkyl or cyclohexyl, Y is a direct bond, --S--, &gt;S.dbd.O or a radical --CR.sup.4 R.sup.5 -- in which R.sup.4 is hydrogen, C.sub.1 -C.sub.8 -alkyl, C.sub.5 -C.sub.8 -cycloalkyl, phenyl or benzyl and R.sup.5 is hydrogen or C.sub.1 -C.sub.8 -alkyl, and Z is 1,2-alkylene or 1,3-alkylene having not more than 15 carbon atoms or o-phenylene, and, if n is 2, X is a group of the formula IV or V ##STR3## in which R.sup.6 is methyl or ethyl, and, if n is 3, X is a phosphorus atom, are suitable for stabilizing organic material against light-induced and/or thermo-oxidative degradation.

Stabilizers for organic polymers

Compounds of the formula I ##STR1## wherein R.sup.1 and R.sup.2 independently of one another are each tert-butyl, R.sup.3 is C.sub.1 -C.sub.20 -alkyl, or C.sub.2 -C.sub.20 -alkyl interrupted by --O-- or --S--, and n is the number 1 or 2, can be obtained, with a very high degree of yield and purity, by reaction of a phenol of the formula II ##STR2## with formaldehyde and a mercaptan of the formula III

Process for producing phenolic thiocarboxylic esters

Compounds of formula I ##STR1## where R.sub.1 and R.sub.2 independently are alpha-branched alkyl of 3 to 8 carbon atoms, R.sub.3 is hydrogen, R.sub.4 is ethylene, 1,3-propylene or 1,4-butylene, and n is 2 or 4 are effective stabilizers for protecting elastomeric or acrylonitrile copolymer compositions or lubricating oil compositions against thermal oxidation and discoloration. 2-Mercaptoethyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate is particularly useful.

Stabilized rubber or lubricant compositions containing mercaptoalkyl

Compounds of the formula ##STR1## in which R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are as defined in the main claim, are suitable for use as stabilizers for organic material, such as polymers or lubricants. In addition to high activity, they are distinguished, in particular, by good color behavior and good compatibility with the substrates to be protected.

Benzylated phenols

The invention relates to phenols which contain a number of aromatic nuclei and in which the bridge formation of these nuclei is in the meta-position to the OH groups. These phenols have the formula I, wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are as defined in claim 1. The novel phenols are most suitable for use as stabilizers for organic polymers and lubricants and have particularly good color properties.

Phenols and use thereof as stabilizers

The invention relates to phenols which contain a number of aromatic nuclei and in which the bridge formation of these nuclei is in the meta-position to the OH groups. These phenols have the formula I, ##STR1## or ##STR2## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, A and n are as defined in claim 1. The novel phenols are most suitable for use as stabilizers for organic polymers and lubricants and have particularly good color properties.

Compounds of the formula V ##STR1## wherein R.sup.2 is straight-chain or branched alkyl of 1 to 8 carbon atoms, cycloalkyl, aryl, alkaryl or aralkyl, L is a bivalent radical, for example --SCH.sub.2 CO.O(CH.sub.2 CH.sub.2 S).sub.y --CH.sub.2 CH.sub.2 -- or --O.COC.sub.p H.sub.2p -- wherein y is a number from 1 to 3 and p is a number from 1 to 18.

Mercaptophenol stabilizers

A process for the manufacture of phenols of the formula I ##STR1## wherein R.sub.1 is alkyl of 1 to 18 carbon atoms, cycloalkyl, phenyl, aralkyl or chlorine, R.sub.2 is hydrogen or has the same meaning as R.sub.1, R.sub.3 is hydrogen or alkyl of 1 to 12 carbon atoms, R.sub.4 is alkylene of 2 to 18 carbon atoms which is unsubstituted or substituted by aryl or hydroxyl, and n is an integer from 0 to 4, which process comprises transesterifying a compound of the formula II ##STR2## wherein R.sub.1, R.sub.2 and R.sub.3 are as defined for formula (I) and R.sub.5 is alkyl of 1 to 4 carbon atoms with a mercapto alcohol of the formula

Phenols useful as stabilizers

A process for the preparation of a p-allylphenol of the formula I, which comprises reacting a phenol of the formula II with an allyl halide of the formula III ##STR1## in which the symbols R.sub.1 to R.sub.6 and X are as defined in the description, in the presence of a base and a phase transfer catalyst. p-Allylphenols are valuable intermediates and lubricant additives.

Process for the preparation of p-allylphenols

Compounds of the formula ##STR1## wherein the symbols R.sub.1 to R.sub.9 have the meanings given in claim 1, are suitable as extreme pressure and antiwear additives in lubricants. The compounds contain as radicals R.sub.5 or R.sub.7 a group of the formula ##STR2## wherein R.sub.10 and R.sub.11 have the meanings given in claim 1. The compounds according to the invention are characterized also as good antioxidants and anti-corrosion agents.

Dithiophosphates as lubricant antioxidents and anti-corrosion agents

Compounds of the formula ##STR1## wherein the symbols R.sub.1, R.sub.2, R.sub.3, m, X, n, Y, q, r and Z have the meanings given in Claim 1. The divalent radical Y can optionally contain a group of the formula ##STR2## wherein R.sub.9 and R.sub.10 have the meanings given in Claim 1. The compounds according to the invention are suitable as antioxidant-stabilizers in organic materials, and impart to lubricants, in addition to having therein a good anti-oxidation and anti-corrosion action, excellent extreme pressure and antiwear properties.

Dithiophosphate stabilizers

Novel oligomeric and polymeric phenolic 1,3,5-triazines, for example those of the formula ##STR1## their preparation and their use for stabilizing organic material and also the organic material protected against oxidative and light-induced degradation with the aid of these compounds.

Phenolic-1,3,5-triazines

A phenol of the formulae I, II or III ##STR1## in which R.sub.1, R.sub.2 and R.sub.3 are independent of one another and one of these is C.sub.1 -C.sub.12 -alkyl, C.sub.5 -C.sub.6 -cycloalkyl or C.sub.7 -C.sub.9 -aralkyl and the others are hydrogen, C.sub.1 -C.sub.12 -alkyl or C.sub.5 -C.sub.6 -cycloalkyl, R.sub.4, R.sub.5, R.sub.6 and R.sub.7 are independent of one another and one of these is C.sub.1 -C.sub.12 -alkyl or C.sub.5 -C.sub.6 -cycloalkyl and the others are hydrogen, C.sub.1 -C.sub.12 -alkyl or C.sub.5 -C.sub.6 cycloalkyl, or R.sub.4 and R.sub.5, or R.sub.6 and R.sub.7, together with the C atom which links them, form a 5-12-membered ring, R.sub.8, R.sub.9 and R.sub.10 are independent of one another and one of these is C.sub.1 -C.sub.12 -alkyl, C.sub.5 -C.sub.6 -cycloalkyl or C.sub.7 -C.sub.9 -aralkyl and the others are hydrogen, C.sub.1 -C.sub.12 -alkyl or C.sub.5 -C.sub.6 -cycloalkyl, x and y independently of one another are 0, 1, 2 or 3, one of m and n is 1 and the other is 0 or 1, A is a monovalent, divalent or trivalent hydrocarbon radical which, in formula II, can also be interrupted by S, and Z is 1, 2 or 3, corresponding to the valency of A, and, in compounds of the formula II and III, m is 1 and R.sub.4 and R.sub.5 independently of one another are C.sub.1 -C.sub.12 -alkyl or C.sub.5 -C.sub.6 -cycloalkyl and, in compounds of the formula I, R.sub.6 can be bridged with A to form a carbocyclic structure as stabilizers for organic material.

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Riehen, Switzerland

Siegfried Rosenberger