- Preparation method of antioxidant 330
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The invention relates to the technical field of chemical material processing, in particular to a synthetic method for preparing a hindered phenol antioxidant 330. The method comprises the following steps: reducing 3, 5-di-tert-butyl-4-hydroxybenzoic acid serving as an initial raw material into 3, 5-di-tert-butyl-4-hydroxybenzyl alcohol, and condensing the 3, 5-di-tert-butyl-4-hydroxybenzyl alcoholwith mesitylene under the action of an acid catalyst to generate the antioxidant 330. In the condensation reaction process, the phase transfer catalyst polyethylene glycol is utilized to improve thecatalytic effect of the concentrated sulfuric acid and reduce the consumption of the concentrated sulfuric acid, thereby having higher industrial value. The reaction yield is high, the optimal yield can reach 95%, the purity of the obtained reduction product is high, and in the industrial process, aftertreatment is simple. Therefore, the antioxidant 330 is synthesized by taking 3, 5-di-tert-butyl-4-hydroxybenzoic acid as an initial raw material and reducing 3, 5-di-tert-butyl-4-hydroxybenzoic acid into alcohol, and the method is a process route with relatively high industrial value.
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Paragraph 0027-0034
(2021/01/29)
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- Bifunctional compound and synthesis method thereof, and applications of bifunctional compound as antioxidant
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The invention discloses a bifunctional compound and a synthesis method thereof, and applications of the bifunctional compound as an antioxidant, wherein the bifunctional compound comprises a hinderedphenol unit, a phosphite unit, a trimethylbenzene unit and a straight-chain segment unit. According to the invention, the synergistic effect of the hindered phenol unit and the phosphite unit and thecontent of the effective functional groups in unit mass are adjusted by controlling the length of the straight-chain segment unit, and the trimethylbenzene structure is beneficial to preventing the antioxidant compound from being precipitated out of the polymer; and the compound can be used as an antioxidant of polypropylene or polyethylene.
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Page/Page column 10-16
(2020/02/14)
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- Novel method for synthesizing antioxidant 330 by catalyst
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The invention aims at providing a method for synthesizing an antioxidant 330. Manganese dioxide-titanium dioxide-molecular sieve loaded phosphoric acid and ferroferric oxide-molecular sieve loaded phosphoric acid catalysts are prepared; under the existence of manganese dioxide-titanium dioxide-molecular sieve loaded phosphoric acid catalysts, 2,6-butylated hydroxytoluene and methyl alcohol are used as preparation raw materials to synthesize 3,5-di-tert-4-hydroxybenzyl ether; the methyl alcohol is used as preparation raw materials to synthesize 3,5-di-tert-4-hydroxybenzyl ether; next, under theexistence of the iron oxide-molecular sieve loaded phosphoric acid catalysts, the 3,5-di-tert-4-hydroxybenzyl ether and mesitylene react to obtain the antioxidant 330. The yield of the synthesized antioxidant is high; the purity is high.
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Page/Page column 12-18
(2018/09/28)
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- Method for synthesizing multi-hindered phenolic antioxidant 330
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The invention relates to a method for synthesizing a multi-hindered phenolic antioxidant 330. The method comprises putting an appropriate amount of 2, 6-di-tert-butyl-4-methoxymethylphenol and dichloromethane into a reactor, controlling the temperature to less than or equal to 10 DEG C, adding mesitylene into the reactor, then controlling the temperature to less than or equal to 5 DEG C, after adding the acid solution drop by drop, maintaining the temperature of 0-5 DEG C for 3-4h, adding an appropriate amount of an alkali solution into the reaction product for neutralization, pouring the liquid after the neutralization reaction into a water segregator, adding water into the water segregator, carrying out washing under the conditions of heating and reflux for 0.5h, removing the water layer, carrying out repeated washing until pH of the water layer is 7-8, distilling the organic layer at 90 DEG C to remove dichloromethane, adding a crystallization solvent into the organic layer, carrying out heating reflux so that the materials are completely dissolved, distilling the solution under -0.1MPa to remove 40 to 50% of the crystallization solvent, cooling the solution to less than 8 DEG C, carrying out crystallization, and carrying out suction filtration and washing to obtain a desired product. The method has simple processes, high production efficiency and low energy consumption.
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Paragraph 0022-0024
(2018/11/03)
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- Antioxidant hindered phenol compound 330 method for the synthesis of (by machine translation)
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The invention provides a synthesis method for a hindered phenolic compound antioxidant 330; the method comprises the following steps: in the presence of a ternary composite catalyst and a diluted hydrochloric acid aqueous solution with specific concentration and amount, a compound represented by the following formula (I) and a compound represented by the following formula (II) are subjected to a reaction in a solvent, and thus the antioxidant 330 is obtained. In the synthesis method, through suitable selection and combination of a catalyst system and a solvent system, the target product is obtained with high yield; and the synthesis method is quite suitable for industrialization large-scale production and application and has a quite broad market prospect.
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Paragraph 0065-0066; 0071; 0074; 0077; 0082; 0090; 0095
(2019/02/02)
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- METHODS AND COMPOSITIONS FOR INHIBITING VINYL AROMATIC MONOMER POLYMERIZATION
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Methods and compositions are provided for inhibiting the polymerization of a vinyl aromatic monomer, such as styrene monomer, during elevated temperature processing thereof or during storage or shipment of polymer containing product. The compositions comprise a combination of a quinone methide derivative A) and a phenol compound B). The methods comprise adding from about 1-10,000 ppm of the combination to the monomer containing medium, per one million parts of the monomer.
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- GREEN AND ATOM-ECONOMICAL PROCESSES FOR PRODUCING PHENOLIC ANTIOXIDANTS
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Processes for producing 1,3,5-trimethyI-2,4,6-tris(3,5-dialkyl-4- hydroxybenzyl)benzene are provided, in particular such processes that utilize 2,6-di-tert- butylphenol, paraformaldehyde, a secondary amine, mesitylene, and acetic acid.
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Page/Page column 9
(2011/02/24)
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- Thioether substituted hydroxybenzophenones and stabilized compositions
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2-Hydroxybenzophenone derivatives substituted in the 4′-position by a thioether moiety exhibit enhanced absorption in the UV at longer wavelength. Compositions comprising organic material subject to actinic degradation are beneficially stabilized with such derivatives.
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- 2-(2′-hydroxyphenyl)benzotriazoles used as U.V. stabilizers
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2-(2′-hydroxyphenyl)benzotriazoles having general formula (I). The above 2-(2′-hydroxyphenyl)benzotriazoles are useful as light stabilizers for organic polymers.
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- Mixture of substances containing compounds with vinyl groups and stabilizers
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A mixture contains one or more vinyl-containing compounds as component (A) and, as a further component, a stabilizer (B) which contains one or more readily volatile nitroxyl compounds as component (b1), one or more sparingly volatile nitroxyl compounds as component (b2), if required one or more aromatic nitro compounds as component (b3) and, if required, one or more iron compounds as component (b4).Stabilizers (B) contain the components (b1) and (b2), (b1) and (b2) and (b3), (b1) and (b2) and (b4), and (b1), (b2), (b3) and (b4), and the premature polymerization of vinyl-containing compounds during their purification or distillation is inhibited by a process in which a stabilizer (B) is added or the components of stabilizer (B) are added as individual substances or in at least two groups of the components.
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- 2-(2′-hydroxyphenyl) benzotriazoles containing a 2,4-imidazolidinedione group and process for their preparation
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2-(2′-hydroxyphenyl)benzotriazoles having general formula (I). The above 2-(2′-hydroyzphenyl)benzotriazoles having general formula (I) are useful as heat, oxygen and light stabilizers for organic polymers. In particular they are useful as UV stabilizers for organic polymers.
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- 2-(2'Hydroxyphenyl) benzotriazoles and process for their preparation
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2-(2'-hydroxyphenyl)benzotriazoles having general formula (I): The above 2-(2'-hydroxyphenyl)benzotriazoles can be used as light stabilizers for organic polymers.
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- 4-acylaminopiperidin-N-oxyle
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4-Acylaminopiperidine N-oxides Ia where A1 is hydrogen or an organic radical and B1 is a radical IIa STR1 where R1 -R4 are each C1 -C4 -alkyl and R1 and R2, on the one hand, and R3 and R4, on the other hand, may furthermore be bonded to form a 5-membered or 6-membered ring, R5 is H or C1 14 C4 -alkyl and R6 is H or C1 -C18 -alkyl, are used for stabilizing organic materials against the harmful effect of free radicals, particularly in the distillation of monomers which undergo free radical polymerization, especially styrene.
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- 2-(2'Hydroxyphenyl) benzotriazoles and their use as light stabilizers for organic polymers
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2-(2'-hydroxyphenyl)benzotriazoles having general formula (I): The above 2-(2'-hydroxyphenyl)benzotriazoles can be used as light stabilizers for organic polymers.
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- Amorphous modification of 1,1',1"-nitrilo(tri-2-propyl-tris-[2,2'-ethylidene-bis(4,6-di-tert-butylphenyl] phosphite)
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The new amorphous modification of 1,1',1"-nitrilo{tri-2-propyl-tris-[2,2'-ethylidene-bis(4,6-di-tert-butylphenyl)]phosphite } is obtained by cooling rapidly said compound from the melt to ambient temperature. This amorphous form is an effective process stabilizer for polyolefins, particularly polypropylene.
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- Beta crystalline modification of 2,2',2"-nitrilo[triethyl-tris-(3,3',5,5'-tetra-tert-butyl-1,1'-biphenyl-2,2'-diyl) phosphite]
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The beta crystalline modification of 2,2',2"-nitrilo[triethyl-tris-(3,3',5,5'-tetra-tert-butyl-1,1'-biphenyl-2,2'-diyl) phosphite] is obtained by crystallizing said compound from the melt at elevated temperatures. The beta crystalline form is an effective process stabilizer for polyolefins, particularly polypropylene.
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- 3,9-carbohydrate substituted 2,4,8,10-tetraoxa-3,9-diphosphaspiro(5.5)undecane phosphite stabilizers
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Carbohydrate substituted phosphites of Formula I STR1 where A is a carbohydrate residue are effective stabilizers for polymers processed at elevated temperatures and subject to thermal or oxidative degradation.
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- Non-migrating 1-hydrocarbyloxy hindered amine derivatives as polymer stabilizers
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1-Hydrocarbyloxy substituted hindered amine compounds which also contain a reactive functional group such as hydroxy, amino, oxirane or carboxyl can be chemically attached to selected polymer substrates by condensation reactions to give polymers containing a chemically-bonded, non-migrating stabilizer having excellent stabilization efficacy for protecting said polymer substrate from the adverse effects of actinic light.
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- Substituted 1,4-diamino-2-butene stabilizers
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N,N,N',N'-Tetrasubstituted 1,4-diamino-2-butenes where the substituents are alkyl, cycloalkyl, aralkyl, aryl or mixtures thereof provide effective antioxidant protection to lubricants and/or synthetic polymers.
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- Perfluoroalkyl substituted hydroxyphenylalkanoic ester antioxidants and stabilized compositions
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Perfluoroalkyl substituted neopentyl alcohols can be reacted with substituted hydroxphenylalkanoic esters to form perfluoroalkyl containing hydroxyphenylalkanoic ester antioxidants. The perfluoroalkyl substituted hindered hydroxyphenyl alkanoates are stablizers which confer superior processing stability to polymers processed at elevated temperatures such as polypropylene, as well as protecting said polymers from thermal and oxidative degradation.
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- Carbohydrate substituted dibenzo(d,f)(1,3,2)dioxaphosphepin stabilizers
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Carbohydrate substituted dibenzo[d,f][1,3,2]dioxaphosphepin compounds of formula I STR1 where A is a carbohydrate residue are effective stabilizers for polymers processed at elevated temperatures and subject to thermal or oxidative degradation.
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- 2-(2-hydroxy-3-perfluoroalkyl thiomethyl-5-alkylphenyl)2H-benzotriazoles and stabilized compositions thereof
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2-(2-Hydroxy-3-perfluoroalkylthiomethyl-5-alkylphenyl)-2H-benzotriazoles are prepared by reacting the Mannich base hydrohalide or quaternary salt of a 2-(2-hydroxy-5-alkylphenyl)-2H-benzotriazole with a perfluoroalkyl mercaptan. The products exhibit outstanding efficacy in protecting organic substrates from light induced deterioration as well as good resistance to loss by volatilization or exudation during the processing of stabilized compositions at elevated temperatures.
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- Substituted 1-hydroxy-2,6-diaryl-4-piperidone ketals and polymer compositions stabilized therewith
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1-Hydroxy-2,6-diaryl-4-piperidone ketal derivatives, such as the compound of formula I STR1 wherein Ar1 and Ar2 are each phenyl, R1 to R6 are all hydrogen, X1 and X2 are each --O-- and T is a direct bond, are novel compounds and are effective process stabilizers, such as polypropylene, for polymers processed at elevated tempertures providing both good melt flow stabilization and good resistance against discoloration during said processing.
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- Substituted 1-aminonaphthalenes and stabilized compositions
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Substituted 1-aminonaphthalenes of formula I STR1 wherein n is 1-3, Ar is arylene, R1 and R2 are independently hydrogen, alkyl or phenyl, R3 is hydrogen, alkyl or substituted alkyl, and R4 and R5 have independently the same definitions as R3 or are independently aryl, substituted aryl or cycloalkyl, are effective stabilizers for lubricating oil or polymer compositions. The instant compounds are particularly effective in lubricating oil compositions when used with a diarylamine antioxidant.
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- Substituted 2,3-dihydroperimidine stabilizers
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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.
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- 2-Propanol derivatives as corrosion inhibitors
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New composition comprises a functional fluid in contact with ferrous metal and a corrosion inhibiting amount of at least one compound of formula (I) STR1 or a derivative thereof in which R1, R2 and R3 are, independently, hydrogen, a C1 -C15 straight or branched chain alkyl residue, a C5 -C12 cycloalkyl residue, a C6 -C15 aryl residue or C7 -C12 alkaryl residue, and R4 and R5 are, independently, hydrogen, 2-hydroxyethyl or 2-hydroxypropyl with the provisos that (a) R4 and R5 are not simultaneously hydrogen, (b) when R4 and R5 are each --CH2 --CH2 --OH, R1 and R2 are not simultaneously hydrogen and R3 is not a pentyl residue and (c) that polyalkylene and phenol or polycarboxylic ester co-additives are absent; as well as salts thereof. Some of the compounds of formula I are new.
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- Corrosion inhibiting composition
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A composition, in contact with a corrodable metal surface, which composition comprises: (a) an aqueous-based or oil-based system; and (b) as inhibitor for protecting the metal surface against corrosion, at least one compound having the formula I: STR1 as well as salts or partial esters thereof wherein: n is 0 or an integer ranging from 1 to 20, R is a straight or branched chain C4 -C30 alkyl group, optionally interrupted by one, two or three oxygen atoms or substituted by one, two or three hydroxy groups, a C5 -C12 cycloalkyl group, a C6 -C10 aryl group optionally substituted by one, two or three C1 -C12 alkyl groups, or a C7 -C13 aralkyl group which is optionally substituted by a hydroxyl group; R1 is H or a straight- or branched chain C1 -C4 alkyl group; R2 is H, a straight or branched chain C1 -C4 alkyl group or CO2 H; R3 is H, a straight or branched chain C1 -C4 alkyl group, --CH2 CO2 H or --CH2 CH2 CO2 H; R4 is H, a straight or branched chain C1 -C4 alkyl group or CO2 H; R5 is H, a straight or branched chain C1 -C4 alkyl group, CH2 CO2 H or CH2 CH2 CO2 H; provided that at least one group R4 must be CO2 H, with the provisio, that compositions comprising an oil-based system and a compound having the formula STR2 wherein R, R1 and R2 are hydrogen or alkyl radicals, having a total from 10 to 38 C-atoms, are excluded.
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- Corrosion inhibition
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The present invention provides a composition in contact with a corrodable metal surface, comprising a functional fluid and, as corrosion inhibitor, a compound having the formula I: as well as salts or esters thereof, wherein, R1 is C4-C20 linear or branched alkyl, phenyl or C7-C20 alkylphenyl;, R2 is C1-C12 linear or branched alkyl, phenyl or C7-C20 alkylphenyl, or arylalkyl containing 7-20 carbon atoms;, X is CH2, O or S;, Y is O or S; and, Z is -(CH2)n- in which n is 1, 2, 3, 4 or 5, or Z is -CH2-CH(CH3)-. Some of the compounds of formula I are new.
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- Organothioethyl alcohol segmers as antidegradant synergists
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This invention is concerned with the stabilization of organic materials subject to oxidative degradation. The synergists of this invention possess organothioethyl alcohol segmers or moieties which enhance the antioxidative activity of phenolic and amine stabilizers. The invention is also concerned with compounds that contain an organothioethyl alcohol moiety and their use in oxidizable materials in combination with polymerizable and/or conventional antidegradants.
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- Methylphosphonic acid amine salt lubricant additives
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Novel salts of methylphosphonic acid with primary amines are described. These compounds are preferably used as extreme pressure additives in lubricant compositions.
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- 1,4-Oxathianones and 1,4-oxathiepanones
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The compounds of the formula STR1 in which R is C1 -C24 alkyl, C3 -C20 alkenyl, C5 -C6 cycloalkyl, unsubstituted or C1 -C4 alkyl-substituted phenyl or phenyl-C1 -C4 alkyl, n is 1 or 2, and X is S or O, are highly suitable as additives, in particular as antiwear and high-pressure additives, and as corrosion inhibitors in functional fluids, for example in lubricants, fuels, hydraulic fluids, metal-working fluids and drilling fluids.
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- Triazole-organodithiophosphate reaction product additives for functional fluids
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New reaction products, useful as additives for functional fluids, are obtained by reacting, at elevated temperature, (A) a triazole having the formula IA or IB: STR1 wherein R7 is hydrogen or a C1 -C20 alkyl residue; R8 and R9 are the same or different and each is C1 -C20 alkyl, C3 -C20 alkenyl, C5 -C12 cycloalkyl, C7 -C13 aralkyl, C6 -C10 aryl or R8 and R9, together with the nitrogen atom to which they are attached, form a 5-, 6- or 7-membered heterocyclic residue or R8 and R9 is each a residue of formula: wherein X is O, S or N(R12), R12 is hydrogen or C1 -C20 alkyl, "alkylene" is a C1 -C12 alkylene residue and n is 0 or an integer from 1 to 6; R10 is hydrogen, C1 -C20 alkyl or C6 -C10 aryl or C7 -C18 alkyl phenyl; and R11 is hydrogen, C1 -C20 alkyl or a residue --CH2 NR8 R9 wherein R8 and R9 have their previous significance; with (B) an organodithiophosphate having the formula: STR2 in which R13 is a C1 -C20 alkyl or C7 -C18 alkyl phenyl or C7 -C13 aralkyl group, M is a metal ion of Group IA, IB, IIA, IIB, VB, VIB, VIIB or VIII of the Periodic System of Elements, and y is the valency of M.
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- Polymerizable thioester synergists
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There are disclosed polymerizable thioester synergists which have utility in enhancing the antioxidative activity of phenolic and amine stabilizers. The invention is also concerned with the thioesters themselves, their use in oxidizable organics, their combination with polymerizable and/or conventional antioxidants, and with polymers which contain these thioesters as physical admixtures or segmeric units of the polymer.
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- Synergistic antioxidant mixtures
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Compounds prepared by reacting maleic anhydride, maleic acid or their esters with thiols; which exhibit a synergistic effect when combined with a phenolic antioxidant in the stabilization of organic materials such as natural and synthetic polymers, rubbers, lubricants and oil, etc. are disclosed.
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- Isocyanuric acid ester stabilizer
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An isocyanuric acid derivative useful as a stabilizer for organic substances, which is represented by the general formula STR1 wherein A represents STR2 R being an alkyl, cycloalkyl, aryl or aralkyl group having 1 to 8 carbon atoms; a process for preparing same; organic substances stabilized with same; and a method of stabilizing an organic substance.
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- Synergistic antioxidant mixtures
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Compounds of the formula: STR1 wherein R, R' and R2 are alkyl radicals having 1 to 20 carbon atoms, phenyl radicals which may be substituted by 1 or 2 alkyl groups having 1 to 8 carbon atoms, aralkyl radicals having 7 to 12 carbon atoms, or cycloalkyl radicals having 5 to 12 carbon atoms; and wherein R3 is hydrogen or an alkyl radical having from 1 to 4 carbon atoms. These compounds have utility as synergistic stabilizers with phenolic type antioxidants for the stabilization of organic materials such as natural and synthetic polymers, rubbers, lubricants and oils, etc.
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- Method for the production of 2,4,6-tri(3,5-ditertiary butyl-4-hydroxybenzyl) mesitylene
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A method for the production of 2,4,6-tri(3,5-ditertiary butyl-4-hydroxybenzyl)mesitylene which resides in treating a mesitylene solution in chloroalkane simultaneously with sulfuric acid used as a catalyst and a solution of 2,6-ditertiary butyl-4-methoxymethylphenol or bis-3,5-ditertiary butyl-4-hydroxybenzyl ether in chloroalkane at a temperature of -20° to +20° C. This results in a reaction mixture consisting of an acid phase and an organic phase including the target product. The phases are separated. The organic phase is subjected to neutralization by the treatment thereof with gaseous ammonia used as an alkaline agent. The precipitate of ammonium sulfate is separated and chloroalkane is removed from the remaining solution. The proposed method makes it possible to obtain the target product with a yield of 88 to 90% and a melting temperature of 239° to 239.5° C. The method prevents the formation of effluents, and the amount of phenol wastes is considerably reduced.
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- Synergistic antioxidant mixtures
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Compounds of the formula: STR1 wherein R is selected from (1) alkyl radicals having 6 to 20 carbon atoms; (2) phenyl radicals which may be substituted by 1 or 2 alkyl groups having 1 to 8 carbon atoms; or (3) aralkyl radicals having 7 to 12 carbon atoms; and wherein R1 is selected from (1) alkylene radicals having 2 to 6 carbon atoms; (2) cycloalkylene radicals having 5 to 12 carbon atoms; (3) alkylcycloalkylene radicals of the formula --R3 --R2 (R4)n, wherein R2 is a cycloalkylene radical having 5 to 12 carbon and R3 and R4 are alkylene radicals having 1 to 6 carbon atoms, and n equals 1 or 0; (4) or a group of the formula --R5 --YR6, wherein R5 and R6 are alkylene radicals having 2 to 6 carbon atoms and Y is oxygen, sulfur, or a 1,4-phenylene radical. These compounds have utility as synergistic stabilizers with phenolic type antioxidants in the stabilization of organic materials such as natural and synthetic polymers, rubbers, lubricants and oils, etc.
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