Ciba-geigy Corporation

Other

David H Steinberg

Martin Dexter

John J Luzzi

Frank P Cortolano

David G Leppard

John D Spivack

Henri Dubas

Raymond R Seltzer

Paul A Odorisio

Thomas E Furia

Compounds of the formula ##STR1## in which R is hydrogen or hydroxyl, R.sub.1 is alkyl, alkoxy, amino or aryl, and R.sub.2 is hydrocarbylcarbonyl or hydrocarbylsulfonyl, are highly suitable for stabilizing magenta couplers in photographic materials.

Substituted benzophenone stabilizers

N-Allyl and N-methylene-thio substituted naphthalene-1,8- or -1,5-diamine compounds are very effective antioxidant stabilizers for organic material subject to oxidative or thermal degradation, particularly for lubricant compositions.

Substituted naphthalenediamine stabilizers

N-Allyl and N-methylene-thio substituted 2,3-dihydroperimidine compounds are very effective antioxidant stabilizers for organic material subject to oxidative or thermal degradation, particularly for lubricant compositions.

Substituted 2,3-dihydroperimidine stabilizers

Process for stabilizing magenta couplers and the corresponding image

An improved process for preparing dithiobisphenols comprising reacting an appropriate phenol with an alkali metal hydride, an alkaline earth metal hydride or mixtures thereof and subsequently reacting the product thereof with sulfur monochloride.

Process for preparing dithiobisphenols

Compounds of the formula I ##STR1## in which R.sub.1 and R.sub.2, independently, denote alkyl with 1 to 6 carbon atoms, cycloalkyl with 5 to 8 carbon atoms, allyl, methallyl, aralkyl with 5 to 9 carbon atoms, phenyl, 1- or 2-naphthyl, or alkaryl with 7 to 9 carbon atoms, R.sub.2 moreover also denotes hydrogen, R.sub.3 denotes hydrogen, alkyl with 1 to 6 carbon atoms, unsubstituted phenyl or phenyl substituted by one or two chlorine atoms and/or one or two methyl groups, B denotes a hetero atom, the group --OC(O)--, --OC(O)--CH.sub.2 CH.sub.2 -- or a direct bond, m is an integer from 0 to 6, and n is an integer from 1 to 6, are prepared by reaction of a thioglycerol derivative with a carboxylic acid containing the hindered phenol moiety in the presence of an acid and are used as antioxidants and thermal stabilizers for lubricating oils, plastics, resins and other organic substrates.

Stabilizer thiirane derivatives containing hindered phenol groups

Esters and urethanes of certain polydialkylsiloxanepolyoxyalkylene block and graft copolymers which impart high voltage stabilization to dielectric olefin polymers, the stabilized olefin polymer insulating materials resulting therefrom and electric wire or cable insulated therewith.

Voltage stabilizing esters and urethanes

Long chain (4-hydroxyphenyl) propanoate derivatives of the formula ##STR1## are effective in stabilizing organic materials against oxidative and thermal degradation.

Long chain (4-hydroxyphenyl) propanoate stabilizers

The title compounds correspond to the formula ##STR1## where R.sub.1 is tert-butyl, R.sub.2 is methyl or tert-butyl, R.sub.3, R.sub.4 and R.sub.7 are hydrogen, R.sub.5 and R.sub.8 are hydrogen or methyl, and R.sub.6 is hydrogen, alkyl of 1 to 3 carbon atoms or phenyl, and are useful as stabilizers for organic polymers and lubricating oils to counteract the degradative effects of heat, light and air.

Substituted 4-hydroxybenzylthio aldehyde and ketone stabilizers

Process for preparing stabilizers containing sulfur and a hindered

The title compounds correspond to the formula ##STR1## wherein A is a monovalent, bivalent, trivalent or tetravalent radical of a mono-, di-, tri- or tetraamine. These compounds are useful as stabilizers for organic polymers and lubricating oils to counteract the degradative effects of heat, light and air.

Anti-oxidative, anti-thermal, and anti-actinic degradation amides of

Hindered phenol hydrazones of the formula ##STR1## wherein R.sub.1 and R.sub.2 are alkyl of 1 to 8 carbons or R.sub.1 can also be hydrogen, n is 1 to 6, R' is hydrogen or alkyl, R.sub.3 is alkyl, phenyl, substituted phenyl, alkylenethioalkyl or alkylenethioether ester of a carboxylic acid or a group ##STR2## where T is a direct bond, alkylene, sulfur or oxygen interrupted alkylene or phenylene, said compounds being useful as diene rubber stabilizers.

Hindered phenol hydrazones and compositions stabilized therewith

Alkylthioalkanoyloxyalkyl and alkylthioalkyl derivatives of N-heterocyclic moieties are stabilizers for organic materials subject to oxidative, thermal and/or light induced deterioration. They are prepared by classical transesterification, oxirane ring opening and addition of mercaptan to olefin reactions. Typical embodiments are tris[2-(3-n-dodecythiopropionyloxy)ethyl isocyanurate] and 3-(3-n-dodecylthio-2-hydroxypropyl)-5,5-dimethylhydantoin. These compounds are used in conjunction with phenolic antioxidants to stabilize organic materials, particularly polyolefins and hydrocarbon compositions, against the deleterious effects of heat and oxygen and against discoloration.

Alkylthioalkanoyloxyalkyl and alkylthioalkyl substituted bis-hydantoin

The compounds are esters having the formula ##STR1## wherein R.sub.1 and R.sub.2 are each independently alkyl, cycloalkyl, alkylthioethyl or alkylpolyoxyalkylene, Z is oxygen or sulfur, R.sub.3 is the group ##STR2## R.sub.4 is hydrogen, alkyl, cycloalkyl or .alpha.-methylbenzyl, R.sub.5 is alkyl or cycloalkyl, R.sub.6 is hydrogen or alkyl and, provided when R.sub.4 is hydrogen, R.sub.6 is alkyl and R.sub.5 is located on the carbon atom ortho to the hydroxyl group, and A is a covalent carbon bond or lower alkylene. The esters of this invention are prepared by usual esterification procedures from a thioether isopropanol and an acid of formula ##STR3## or a derivative thereof, preferably the methyl ester. The thioether isopropanols are prepared by reaction of epichlorohydrin with an alcohol or mercaptan followed by the opening of the oxirane ring with a mercaptide to give the desired thioether isopropanol. The compounds are useful as stabilizers for organic materials, especially polyolefins, which degrade upon exposure to light and heat.

Hindered hydroxyphenylalkanoates of thioether isopropanols and

The compounds are esters having the formula ##STR1## wherein R.sub.1 is alkyl, cycloalkyl, alkylthioethyl or alkylpolyoxyalkylene, Z is oxygen or sulfur, R.sub.2 is the group ##STR2## R.sub.3 is hydrogen, alkyl, cycloalkyl, or .alpha.-methylbenzyl, R.sub.4 is alkyl or cycloalkyl, R.sub.5 is hydrogen or alkyl, provided when R.sub.3 is hydrogen, R.sub.5 is alkyl and R.sub.4 is located on the carbon atom ortho to the hydroxyl group, and A is a covalent carbon bond or lower alkylene.

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Bronx, NY, United States of America

David H Steinberg