Mallinckrodt, Inc.

Mallinckrodt Specialty Chemicals Company

Millinckrodt, Inc.

Ali A Bazzi

Neil Dunski

Henry J Buehler

Multifunctional dithiodialkanoic acid esters useful in the stabilization of organic materials normally susceptible to oxidative degradation are prepared by contacting a selected dithiodialkanoic acid chloride with a selected 4-(3-hydroxypropyl)(mono- or di-alkyl) phenol under ester-forming reaction conditions. In a preferred embodiment, the ester is bis-3-(3',5'-di-t-butyl-4'-hydroxyphenyl)propyl dithiodipropionate.

Dithiodialkanoic acid esters and polymers stabilized therewith

Pentaerythritol co-esters derived from pentaerythritol, (3-alkyl-4-hydroxyphenyl)-alkanoic acids and alkylthioalkanoic acids or lower alkyl esters of such acids are useful as stabilizers of organic material normally susceptible to oxidative and/or thermal deterioration. The co-esters are advantageously prepared by transesterification of such esters with pentaerythritol. Preferred co-esters are (I) pentaerythritol tris[3,5-di-tert-butyl-4-hydroxyphenyl)propionate]-mono[3-n-dodecylthiopro pionate] and (II) pentaerythritol bis[-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate]-bis[3-n-dodecylthiopro pionate]. The co-esters are especially useful in stabilizing applications for which physical mixtures of (i) (3-alkyl-4-hydroxyphenylalkanoic acid esters of polyols with (ii) polyalkanol esters of alkylthioalkanoic acids have heretofore been proposed.

Method of making mixed pentaerythritol esters having up to 75 percent

Pentaerythritol co-esters derived from pentaerythritol, (3-alkyl-4-hydroxyphenyl)-alkanoic acids and alkylthioalkanoic acids or lower alkyl esters of such acids are useful as stabilizers of organic material normally susceptible to oxidative and/or thermal deterioration. The co-esters are advantageously prepared by transesterification of such esters with pentaerythritol. Preferred co-esters are (I) pentaerythritol tris[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate]-mono[3-n-do-decylthi opropionate] and (II) pentaerythritol bis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate]-bis[3-n-dodecylthiopr opionate]. The co-esters are especially useful in stabilizing applications for which physical mixtures of (i) (3-alkyl-4-hydroxyphenyl)alkanoic acid esters of polyols with (ii) polyalkanol esters of alkylthioalkanoic acids have heretofore been proposed.

Pentaerythritol co-esters where up to 75 percent of the acid component

Pentaerythritol co-esters derived from pentaerythritol, (3-alkyl-4-hydroxyphenyl)-alkanoic acids and alkylthioalkanoic acids or lower alkyl esters of such acids are useful as stabilizers of organic material normally susceptible to oxidative and/or thermal deterioration. The co-esters are advantageously prepared by transesterification of such esters with pentaerythritol. Preferred co-esters are (I) pentaerythritol tris[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate]-mono[3-n-dodecylthio propionate]and (II) pentaerythritol bis [3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate]-bis[3-n-dodecylthiopropi onate]. The co-esters are especially useful in stabilizing applications for which physical mixtures of (i) (3-alkyl-4-hydroxyphenyl)alkanoic acid esters of polyols with (ii) polyalkanol esters of alkylthioalkanoic acids have heretofore been proposed.

Pentaerythritol co-esters containing sulfur in at least one of the acid

Pentaerythritol co-esters derived from pentaerythritol, (3-alkyl-4-hydroxyphenyl)-alkanoic acids and alkylthioalkanoic acids or lower alkyl esters of such acids are useful as stabilizers of organic material normally susceptible to oxidative and/or thermal deterioration. The co-esters are advantageously prepared by transesterification of such esters with pentaerythritol. Preferred co-esters are (I) pentaerythritol tris[3-(3,5-di-tert-butyl-4-hydroxylphenyl)propionate]-mono[3-n-dodecylthi opropionate] and (II) pentaerythritol bis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate]-bis[3-n-dodecylthiopr opionate]. The co-esters are especially useful in stabilizing applications for which physical mixtures of (i) (3-alkyl-4-hydroxyphenyl)alkanoic acid esters of polyols with (ii) polyalkanol esters of alkylthioalkanoic acids have heretofore been proposed.

Pentaerythritol co-esters

Isocyanurate esters of thioalkanoamidophenols useful in the stabilization of organic materials normally susceptible to oxidative degradation are prepared by reacting an appropriate isocyanurate trithiol, which is a selected tris-mercapto alkanoic acid ester of tris-(2-hydroxyethyl) isocyanurate with an appropriate alkenyl compound, which is a selected N-alkenyl[4-amino-(mono- or dialkyl)phenol] or, where the alkano moiety is a sole methylene group, by reaction of tris-(2-hydroxyethyl) isocyanurate with an appropriate [mercapto-N-(mono- or di-alkyl]-4-hydroxyphenylalkanamide alkenoic] acid. In a preferred embodiment, the ester is 1,3,5-tris{2-hydroxy ethyl-[3-mercapto-(3',5'-di-tert-butyl-4'-hydroxypropionanilide)]propionat e}isocyanurate.

Anti-oxidant isocyanurate ester of thioamidophenol and polyolefins

Polyol carboxyalkylthioalkanoamidophenol compounds useful in the stabilization of organic materials normally susceptible to oxidative degradation are prepared by (A) reaction of an appropriate polythiol, which is a selected tetra-(mercapto alkanoic acid) ester of pentaerythritol or a selected tri-(mercapto alkanoic acid) ester of a selected 1,1,1-trimethylolalkane, with an appropriate alkenyl compound, which is a selected N-alkenoyl[4-amino(mono- or dialkyl)phenol] or (B), where the alkanol moiety is a sole methylene group, by reaction of pentaerythritol or an appropriate 1,1,1-trimethylolalkane with an appropriate mercapto-N(mono- or di-alkyl-4-hydroxyphenylalkamide) alkanoic acid. In a preferred embodiment, the compound is pentaerythritol tetrakis[3-mercapto-N-(3',5'-di-ti-butyl-4'-hydroxyphenyl propanamide) propionate].

Polyol carboxyalkylthioalkanoamidophenol compounds and organic material

Isocyanurate esters of thioalkanoamidophenols useful in the stabilization of organic materials normally susceptible to oxidative degradation are prepared by reacting an appropriate isocyanurate trithiol, which is a selected tris-mercapto alkanoic acid ester of tris-(2-hydroxyethyl) isocyanurate with an appropriate alkenyl compound, which is a selected N-alkenoyl[4-amino-(mono- or dialkyl)phenol] or, where the alkano moiety is a sole methylene group, by reaction of tris-(2-hydroxyethyl) isocyanurate with an appropriate [mercapto-N-(mono- or di-alkyl-4-hydroxyphenylalkanamide alkenoic] acid. In a preferred embodiment, the ester is 1,3,5-tris{2-hydroxy ethyl-[3-mercapto-(3',5'-di tert-butyl-4'-hydroxypropionanilide)]propionate}isocyanurate.

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Creve Coeur, MO, United States of America

Ali A Bazzi