- Synthetic method of antioxidant 565
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The invention discloses a synthetic method of an antioxidant 565. The antioxidant 565 refers to 4-[4, 6-dioctyl-1, 3, 5-triazine-2-group] amino]-2, 6-di-tert-butylphenol; acid, 2, 6-di-tert-butylphenol and sodium nitrite are added into an organic solvent for nitrification reaction, and 2,6-ditert-butyl-4-nitrosophenol; sodium hydroxide and a reductant are added, and 2,6-ditert-butyl-4-nitrosophenol has a reduction reaction to generate 2,6-di-tert-butyl-4-aminophenol; n-octyl mercaptan reacts with cyanuric chloride under action of a catalyst to generate a 2,4-dioctyl thiol-6-chlorine-1,3,5-triazine compound; 2,6-ditert-butyl-4-nitrosophenol reacts with the 2,4-dioctyl thiol-6-chlorine-1,3,5-triazine compound to generate 4-[4, 6-dioctyl-1, 3, 5-triazine-2-amino]-2, 6-di-tert-butylphenol. Thesynthesis method avoids the use of an expensive hydrogenation catalyst and dangerous high pressure. The reaction condition is mild, operation is simple, the yield is high, the quality of intermediateproducts is good, and the yield and quality of the prepared 4-[4,6-dioctylthio-1,3,5-triazine-2-group] amino] 2,6-di-tert-butylphenol are higher.
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- 4-Formyl amino-n-methylpiperidine derivatives, the use thereof as stabilisers and organic material stabilised therewith
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The present invention relates to 4-formylamino-N-methylpiperidine derivatives of the formula (I) where the variables are as defined in the Description, to a process for preparing these piperidine derivatives, to the use of these piperidine derivatives of the invention, or prepared according to the invention, for stabilizing organic material, in particular for stabilizing plastics or coating materials, and also to the use of these piperidine derivatives of the invention, or prepared according to the invention, as light stabilizers or stabilizers for wood surfaces. The present invention further relates to stabilized organic material which comprises these piperidine derivatives of the invention or prepared according to the invention.
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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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- 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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- Piperidyl organosiloxanes and polymer substrates light-stabilized therewith
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Novel piperidyl organosiloxanes, well adapted for the light/UV-stabilization of a wide variety of polymer substrates, e.g., polyolefins and polyalkadienes, have the structural formula (I): STR1
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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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- Process for the preparation of polyalkyl-1-oxa-diazaspirodecane compounds
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The invention relates to a process for the preparation of polyalkyl-1-oxa-diazaspirodecane compounds, which can be used as highly active light stabilizers for polymers. The reaction is carried out in a solvent mixture of at least one alcohol and if appropriate an inert organic solvent in the presence of solid alkali metal hydroxide or a corresponding amount of a mixture of solid alkali metal hydroxide and water as the sole catalyst. The process offers the advantage that, by using a solvent mixture and dispensing with a phase transfer catalyst, a higher rate of reaction and therefore higher product quality with the same yield are achieved. By dispensing with a phase transfer catalyst, which remains in the waste water and must be disposed of expensively, and by the reusability of the solvent mixture, the process is more environment-friendly and more economical than processes known to date.
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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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- 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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- 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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- Piperidine compounds containing silane groups for use as stabilisers for organic materials
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The present invention relates to novel piperidine compounds of the formula (I) STR1 in which A is e.g. a group of the formula STR2 where R4 is e.g. hydrogen or methyl, X3 is e.g. --O-- or --NH-- and R5 ' is e.g. ethylene, propylene or decamethylene, R1 is e.g. methyl, methoxy, ethoxy or OH, R2 and R3 are e.g. methyl, m+n is e.g. a number from 1 to 40, n varies e.g. from zero to 50% of the sum m+n, X1 is e.g. as defined for R1 or is a group (CH3)3 SiO-- and X2 is e.g. hydrogen, methyl, ethyl, a group (CH3)3 Si-- or a group STR3 and, when m+n is a number from 3 to 10, X1 and X2 together also form a direct bond. The compounds of the formula (I) are effective in stabilising an organic material against thermal, oxidative and light-induced degradation.
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- Non-migrating 1-hydrocarbyloxy-2,2,6,6-tetramethylpiperidine 1,3,5-triazine derivatives
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1-Hydrocarbyloxy-2,2,6,6-tetramethylpiperidine derivatives of s-triazines having functional groups such as hydroxy, amino, carboxy, epoxy, isocyanate or the like present are capable of chemically bonding with polymer substrates having anhydride, epoxide, alkoxymethylmelamine or isocyanate moieties present. This chemical bonding prevents migration or loss of the stabilizer during subsequent processing or end-use application of the stabilized polymer.
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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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- Process for the preparation of alkylhydroxyanilinothiotriazine derivatives
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A process for the preparation of compounds of formula I STR1 wherein R1 and R2 are each independently of the other hydrogen, C1 -C12 alkyl, C5 -C6 cycloalkyl or phenyl, and R3 and R4 are each independently of the other C1 -C18 alkyl, C5 -C6 cycloalkyl, phenyl, phenyl which is substituted by C1 -C6 alkyl and/or hydroxy, or phenyl-C1 -C4 alkyl. The process comprises reacting a compound of formula III STR2 with a nitrite in aqueous or aqueous/organic medium to a compound of formula II STR3 extracting said compound of formula II from the reaction solution with a solvent, hydrogenating said compound, without isolation, in the cited solvent and in the presence of a palladium catalyst, to the corresponding p-aminophenol, and reacting said aminophenol, without isolation, with cyanuric chloride and a compound of formula HSR3 or HSR4 or a mixture of compounds of formulae HSR3 and HSR4. The products are obtained in high yield and purity.
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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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- 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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- Piperidine derivatives
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New 1- and 4-substituted piperidines are stabilizers for organic material. They are produced by reacting corresponding 1-substituted piperidinols with acid chlorides or corresponding 4-substituted piperidines with a compound introducing into the 1-position a residue.
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- Piperidine derivatives
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New piperidine derivatives of 1,3-pyrimidine and 1,3,5-triazine are used as stabilizers for organic materials, especially for polymers.
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- Acylated derivatives of substituted piperazines and polymeric compositions stabilized thereby
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Acylated derivatives of substituted piperazines are stabilizers for synthetic polymeric materials normally subject to deterioration caused by ultraviolet light. The compounds are prepared by the acylation reaction between a substituted piperazine and a mono or di-acid halide, ester or isocyanate. Polymeric compositions containing these stabilizers may also contain a hindered phenolic compound. A typical embodiment is 15-stearoyl-7,15-diazadispiro[5,1,5,3]hexadecane.
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- Substituted piperazines and polymeric compositions stabilized thereby
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Substituted piperazines are stabilizers for synthetic polymeric materials normally subject to deterioration caused by ultraviolet light. The compounds are prepared by the alkylation reaction between a substituted piperazine dione and an organic halide followed by reduction with lithium aluminum hydride. Polymeric compsitions containing these stabilizers may also contain a hindered phenolic compound. A typical embodiment is 15,15'-dodecamethylene-bis(7,15-diazadispiro[5,1,5,3]hexadecane).
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- Substituted piperidin-4-ols
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Disclosed are stabilized compositions comprising a polymer, especially polyolefines, and a minor proportion of a 1,2,2,6,6-pentasubstituted piperidin-4-ol. The new compositions possess good light stability.
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- Hydroxyaryl-tetramethyl-piperidines
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New 4-(4'-hydroxyaryl)-2,2,6,6-tetramethyl-piperidines are used as stabilisers for organic materials, especially for polymers.
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- Substituted piperazine diones and polymeric compositions stabilized thereby
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Substituted piperazine diones are stabilizers for synthetic polymeric materials normally subject to deterioration caused by ultraviolet light. The compounds are prepared by the alkylation reaction between a substituted piperazine dione and an organic halide. Polymeric compositions containing these stabilizers may also contain a hindered phenolic compound. A typical embodiment is 15,15'-dodecamethylenebis(7,15-diazadispiro[5,1,5,3]hexadecane-14,16-dione).
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- 1,4-Diazaepine-5-ones
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According to the present invention, there are provided compounds having the formula: SPC1 And salts thereof, wherein n is 1 or 2, X is O of NH, Y is O, hydrogen or a branched- or straight chain alkyl residue having from 1 to 4 carbons and R1 is a hydrocarbyl residue having from 1 to 20 carbon atoms, which are useful as stabilisers for polymers.
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- Esters of piperidinols
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New alkyl substituted p-hydroxy aryl esters and alkyl substituted p-hydroxy aralkyl esters of 2,2,6,6-tetrasubstituted piperidin-4-ols are used as stabilizers for organic materials, especially for polymers.
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- 4-Piperidine acetamides
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New piperidine derivatives and in particular esters and amides of substituted (piperidinyl-4) acetic acid are used as stabilisers for polymers, especially for polyolefines.
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- 3,5-Dialkyl-4-hydroxyphenylalkyl substituted piperazine diones and polymeric compositions stabilized thereby
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3,5-dialkyl-4-hydroxyphenylalkyl substituted piperazine diones are stabilizers for synthetic polymeric materials normally subject to deterioration caused by ultraviolet light. The compounds are prepared by the alkylation reaction between a substituted piperazine dione and 3,5-dialkyl-4-hydroxyphenylalkyl halide. Polymeric compositions containing these stabilizers may also contain a hindered phenolic compound. A typical embodiment is 15-(3',5'-di-t-butyl-4'-hydroxybenzyl)(7,15-diazadispiro[5,1,5,3]hexadecane-14,16-dione).
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- Alkyl alkanoate derivatives of substituted piperazine-diones and polymer compositions stabilized thereby
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Alkyl alkanoate derivatives of substituted piperazinediones are stabilizers for synthetic polymeric materials normally subject to deterioration caused by ultraviolet light. The compounds may be formed by reacting a substituted piperazinedione with an acrylate or a crotonate, or reacting the alkali or alkaline earth salt of a substituted piperazine dione with a haloalkanoate. Polymeric compositions containing these stabilizers may also contain a hindered phenolic compound. A typical embodiment is n-octadecyl-β-(15{7,15-diazadispiro[5,1,5,3]hexadecane-14,16-dione}propionate.
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- 4-(4'-Hydroxycyclohexyl)-2,2,6,6-tetramethyl piperidines
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A compound having the formula:- SPC1 And salts thereof, wherein R1, R2, R3 and R4 are the same or different and each is hydrogen, an alkyl residue having from 1 to 9 carbon atoms, a cycloalkyl residue having from 5 to 14 carbon atoms or a cycloalkyl-alkyl residue having from 7 to 14 carbon atoms, Y is hydrogen, 0°, an alkyl residue having from 1 to 4 carbon atoms, or an aralkyl residue having from 7 to 12 carbon atoms and Z is hydrogen, an unsubstituted or substituted alkyl residue having from 1 to 20 carbon atoms, an alkenyl or alkynyl residue having from 2 to 20 carbon atoms, a cycloalkyl residue having from 5 to 12 carbon atoms, an aralkyl residue having from 7 to 12 carbon atoms, an aryl residue having from 6 to 12 carbon atoms, or the group having the formula: wherein Z1 has the same significance as Z as hereinbefore defined, or Z1 is a group --NR5 R6 wherein R5 is hydrogen or an alkyl residue having from 1 to 4 carbon atoms and R6 is hydrogen, an alkyl group having from 1 to 20 carbon atoms, a cycloalkyl group having from 5 to 12 carbon atoms, an aralkyl residue having from 7 to 12 carbon atoms or an aryl residue having from 6 to 12 carbon atoms having light stabilising activity.
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- Piperidine derivatives
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New piperidine derivatives and in particular esters and amides of substituted (piperidinylidene-4) acetic acid are used as stabilizers for polymers, especially for polyolefines.
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- N-carbamoyl imidazolidinones and imidazolidinethiones
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Compounds having the formula SPC1 As well as salts thereof, wherein n is 1 or 2, Y is 0, hydrogen or a straight- or branched chain alkyl residue having from 1 to 4 carbon atoms Z is 0 or S and when n is 1, R1 is a substituted or unsubstituted hydrocarbyl residue having from 1 to 20 carbon atoms and when n is 2, R1 is a substituted or unsubstituted hydrocarbyl residue having from 2 to 20 carbon atoms, are suitable as stabilisers of organic material.
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- Piperidine derivatives
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A composition comprising an organic material and, as stabiliser, a compound having the formula SPC1 And salts thereof, wherein R1 and R2 are the same or different and each is an alkyl residue having from 1 to 12 carbon atoms or R1 and R2, together with the carbon atom to which they are bound, form a cycloalkyl residue having from 5 to 12 carbon atoms in the ring, Y is O, hydrogen, a straight or branched alkyl residue having from 1 to 20 carbon atoms, an alkenyl or alkynyl residue having from 3 to 12 carbon atoms, an aralkyl residue having from 7 to 12 carbon atoms or a group having the formula EQU1 wherein R is hydrogen, or a methyl or phenyl residue and R3 is hydrogen or a straight- or branched chain alkyl residue having from 1 to 12 carbon atoms.
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- 4-(Carboxamidoethyl) piperidines
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New piperidine derivatives and in particular 2-(piperidinyl-4')-ethyl-amines, -ethers and -esters are used as stabilisers for polymers, especially for polyolefines.
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- Substituted piperazine dione oxyls and hydroxides and polymer compositions stabilized thereby
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Substituted piperazine dione oxyls and hydroxides are stabilizers for synthetic polymeric materials normally subject to deterioration caused by ultraviolet light. The compounds may be prepared by first preparing a substituted piperazine dione with subsequent oxidation of the piperazine dione to yield the oxyl and reduction of the oxyl to yield the hydroxide derivative. Polymeric compositions containing these stabilizers may also contain a hindered phenolic compound. A typical embodiment is 15-n-octadecyl-7-oxyl-7,15-diazadispiro[5,1,5,3]hexadecane-14,16-dione.
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