Mallinckrodt, Inc.

Ciba Specialty Chemicals Corporation

Mallinckrodt Specialty Chemicals Company

Mallinckrodt Medical, Inc.

Millinckrodt, Inc.

Neil Dunski

Ali A Bazzi

Henry J Buehler

Kurt Hoffmann

Bruno Rotzinger

Samuel D Riccitelli

Dietmar Mäder

John F Goodman

The invention describes novel mixtures comprising i) a processing stabilizer selected from the group consisting of hydroxylamine stabilizers, nitrone stabilizers, benzofuran-2-one stabilizers and/or a compound of the formula I wherein Ris C-Calkyl, Ris C-Calkyl, and ii) an antistatic agent selected from the group consisting of an ethoxylated amine and/or an ethoxylated amide, as stabilizers for protecting organic materials, in particular synthetic polymers, against oxidative, thermal or lightinduced degradation 

Stabilization of organic materials

A stabilizing system for stabilizing polymeric materials against ultraviolet light and thermooxidative deterioration is provided in which the stabilizing system is in pellet form. The pellet is formed from a substantially dry homogeneous mixture of at least one stabilizer and an agent which will prevent melting of the stabilizer. The stabilizer compound makes up about 50% to about 98% by weight of the mixture. The stabilizers are antioxidants (such as phosphites and hindered phenols) or hindered amine UV light stabilizers, or combinations thereof. The melt preventing agent may be a compound derived from a fatty acid or a fatty alcohol, or a fatty acid or a fatty alcohol, or a combination of fatty acids or fatty alcohols which makes up about 3%-10% of the homogeneous mixture. The fatty acids, fatty alcohols, and the compounds derived therefrom preferably have a low melting point in the range of 50.degree.-100.degree. C. and preferably between 50.degree. C. and about 80.degree. C. The melt preventing agent may alternatively be a lubricating agent having a small particle size (e.g., less than 100 .mu.) which makes up about 2-50% by weight of the homogeneous mixture.

Stabilization systems for polymeric material in pellet form

A carbon dioxide indicator for use in determining the proper placement of endotracheal tubes. The indicator is comprised of a pH-sensitive dye suspended in a predominantly hydrophilic polymer matrix. The indicator may be placed inside a tube or connector to form an indicator device. When the pH-sensitive dye changes color due to CO.sub.2 and moisture in exhaled air, the color change is visible from outside the device.

Carbon dioxide indicator

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

Metallic salt powder pellets are formed by blending metallic salt powder of aliphatic monocarboxylic acid, with a binder material capable of binding the metallic salt powder under normal bulk handling and transport conditions without altering end use properties of the metallic salt powder, and passing the blended composition through a pellet mill. The metallic salt powder pellets can be handled and transported with greatly reduced risk of generating hazardous dust, and readily disintegrate in conventional blending and mixing apparatus to disperse in a manner similar to unpelletized metallic salt powder.

Metallic fatty acid pellets and method of manufacture

N-acylated dialkylaminophenols are produced at greater yields under mild reaction conditions by a novel in situ process which begins with catalytic hydrogenation of dialkylnitrosophenols in an aprotic organic reaction medium.

Method for making aminophenols and their amide derivatives

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

Disclosed are stabilized linear low-density polyethylene (LLDPE) compositions containing a stabilizing amount of a ring-substituted N-acyl-para-aminophenol. In a preferred embodiment, the latter compound is N-stearoyl-2,6-di-t-butyl-4-aminophenol.

Stabilized linear low-density polyethylene containing ring-substituted

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

Polyol carboxyalkylthioalkanoesterphenol compounds useful in the stabilization of organic materials normally susceptible to oxidative degradation are prepared by reaction of an appropriate polythio, 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 4-hydroxy-(mono- or di-alkyl)phenylalkylalkenoate. In a preferred embodiment, the compound is pentaerythritol tetrakis [3,5-di-tert-butyl-4-hydroxyphenyl-(3-propyl)oxycarbonylethylthiopropionat e].

Polyol carboxyalkylthioalkanoesterphenol compounds and organic materials

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 carboxyalkylthioalkanoesterphenols 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 4-hydroxy-(mono- or di-alkyl)phenyl alkyl alkenoate. In a preferred embodiment, the ester is 1,3,5-tris [( 3,5-di-tert-butyl-4-hydroxyphenyl)-(3-propyl) oxycarbonylethylthiopropionyloxyethyl] isocyanurate.

Isocyanurate esters of carboxyalkylthioalkanoesterphenol compounds and

Disclosed are stabilized A-B-A type block copolymer compositions containing at least two monoalkenyl arene polymer end blocks and at least one polydiene internal block and a stabilizing amount of a ring-substituted N-acyl-para-aminophenol. In two preferred embodiments, the latter compound is N-stearoyl-2,6-di-t-butyl-4-aminophenol, while the block copolymers are polystyrene-polybutadiene-polystyrene and polystyrene-polyisoprene-polystyrene, respectively.

Stabilized block copolymer compositions containing ring-substituted

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.

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Creve Coeur, MO, United States of America

Neil Dunski