RU2008140929A - MODIFIED WAXES, METHOD FOR PRODUCING THEM AND THEIR APPLICATION - Google Patents

Abstract

 1. The compounds of formula (A)! ! in which L1 are the same or different and represent a group of formula (M)! ! in which (***) is the bond of a group of formula (M) with a group E in formula (A); ! G1 and G2 can be the same or different and independently represent each other! hydrogen, halogen, NO2, cyano, CONR5R6, (R9) COOR4, C (O) -R7, OR8, SR8, NHR8, N (R18) 2, carbamoyl, di (C1-C18-alkyl) carbamoyl, C (= NR5 ) (NHR6), C1-C18 alkyl; C3-C18 alkenyl; C3-C18 alkynyl, C7-C9 phenylalkyl, C3-C12 cycloalkyl or C2-C12 heterocycloalkyl; ! C1-C18-alkyl or C3-C18-alkenyl or C3-C18-alkynyl or C7-C9-phenylalkyl, C3-C12-cycloalkyl or C2-C12-heterocycloalkyl, in each case substituted by OH, halogen, NO2, amino, cyano , carboxyl, COOR21, C (O) -R22, C1-C4 alkoxy groups, C1-C4 alkylthio groups, C1-C4 alkylamino groups, di (C1-C4 alkyl) amino groups or OC (O) -R7; ! C2-C18 alkyl interrupted by at least one O atom and / or by -NR5-; ! C6-C10 aryl; ! phenyl or naphthyl, in each case substituted by C1-C4 alkyl, C1-C4 alkoxy groups, C1-C4 alkylthio groups, halogen, cyano groups, hydroxyl, carboxyl, COOR21, C (O) -R22, C1-C4 alkylamino groups or di (C1-C4-alkyl) amino group; ! or ! G1 and G2 together with the C atom to which they are attached form a C3-C12 ring; ! T1 is hydrogen, primary C1-C18 alkyl, secondary C3-C18-alkyl, tertiary C4-C18-alkyl or phenyl group, each of them unsubstituted or substituted by halogen, OH, COOR21 and C (O) -R22; or ! T1 is C5-C12 cycloalkyl, C5-C12 cycloalkyl interrupted by at least one O or —N (R18) -; or ! T1 is a polycyclic alkyl group having 7-18 C atoms, or a similar g

Claims (11)

1. The compounds of formula (A)

in which L1 are the same or different and represent a group of formula (M)

in which (***) is the bond of a group of formula (M) with a group E in formula (A); G1 and G2 may be the same or different and independently represent hydrogen, halogen, NO ₂ , cyano, CONR ₅ R ₆ , (R ₉ ) COOR ₄ , C (O) -R ₇ , OR ₈ , SR ₈ , NHR ₈ , N (R ₁₈ ) ₂ , carbamoyl, di (C ₁ -C ₁₈ -alkyl) carbamoyl, C (= NR ₅ ) (NHR ₆ ), C ₁ -C ₁₈ -alkyl; C ₃ -C ₁₈ alkenyl; C ₃ -C ₁₈ alkynyl, C ₇ -C ₉ phenylalkyl, C ₃ -C ₁₂ cycloalkyl or C ₂ -C ₁₂ heterocycloalkyl; C ₁ -C ₁₈ alkyl or C ₃ -C ₁₈ alkenyl or C ₃ -C ₁₈ alkynyl or C ₇ -C ₉ phenylalkyl, C ₃ -C ₁₂ cycloalkyl or C ₂ -C ₁₂ heterocycloalkyl in each case substituted by OH, halogen, NO _2, amino, cyano, carboxyl, COOR _21, C (O) -R _22, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ alkylamino di (C ₁ -C ₄ alkyl) amino group or OC (O) -R ₇ ; C ₂ -C ₁₈ -alkyl interrupted by at least one O atom and / or by -NR ₅ -; C ₆ -C ₁₀ aryl; phenyl or naphthyl, in each case substituted with C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, halogen, cyano, hydroxyl, carboxyl, COOR ₂₁ , C (O) -R ₂₂ , a C ₁ -C ₄ alkylamino group or a di (C ₁ -C ₄ alkyl) amino group; or G1 and G2 together with the C atom to which they are attached form a C ₃ -C ₁₂ ring; T1 is hydrogen, primary C ₁ -C ₁₈ alkyl, secondary C ₃ -C ₁₈ -alkyl, tertiary C ₄ -C ₁₈ -alkyl or phenyl group, each of them unsubstituted or substituted by halogen, OH, COOR ₂₁ and C (O) -R ₂₂ ; or T1 is C ₅ -C ₁₂ cycloalkyl, C ₅ -C ₁₂ cycloalkyl interrupted by at least one O or —N (R ₁₈ ) -; or T1 is a polycyclic alkyl group having 7-18 C atoms, or a similar group interrupted by at least one —O— or —N (R ₁₈ ) -; T2 represents hydrogen, halogen, NO ₂ , a cyano group or a monovalent organic group having 1-50 C atoms; or T2 and T1 together form a group of formula (F)

in which (*) denotes a bond with a Quaternary atom C, substituted by G1 and G2, in the formula (M), and (**) means a bond with nitrogen N in the formula (M), E2 is —CO— or - (CH ₂ ) _b -, where b is 0, 1 or 2; E1 is —CO—, - (C = NR ₂₃ ) -, - (NR ₂₃ ) -, - (CR ₂₄ R ₂₅ ) -, or —O—, where R ₂₄ and R ₂₅ are the same or different and independently from each other represent H, OH, OR ₂₆ or NR ₂₇ R ₂₈ or R ₂₄ and R ₂₅ together form a group of formula (H)

in which (****) and (*****) represent a bond with a Quaternary carbon atom of the group - (CR ₂₄ R ₂₅ ) - in E1 from the formula (F); H1 is —CH ₂ -, —CO— or —NR ₂₉ -; H2 is —O—, —CH ₂ -, —CO— or —NR ₂₉ -; R ₂₃ , R ₂₆ , R ₂₇ , R ₂₈ and R ₂₉ are the same or different and independently represent hydrogen or an organic group having a total of 1-500 carbon atoms and 0-200 heteroatoms, where the heteroatoms are oxygen, nitrogen, sulfur, phosphorus, silicon or halogens, L2 is a divalent organic group having 1-500 C atoms and 0-200 heteroatoms, where the heteroatoms are oxygen, nitrogen, sulfur, phosphorus, silicon or halogens, and which together with H1 and H2 from formula (H) and quaternary a carbon atom from - (CR ₂₄ R ₂₅ ) - in E1 from formula (F) forms an optionally substituted 4-, 5-, 6- or 7-membered ring, preferably a 5- or 6-membered ring; and R ₄ represents hydrogen, C ₁ -C ₁₈ -alkyl, phenyl, an alkali metal ion or tetraalkylammonium cation; R ₅ and R ₆ independently of one another are C ₁ -C ₁₈ alkyl, C ₂ -C ₁₈ alkyl substituted with hydroxyl, or, taken together, form a C ₂ -C ₁₂ alkylene bridge or C ₂ -C ₁₂ an alkylene bridge interrupted by —O— or / and —N (R ₁₈ ) -; R ₇ represents hydrogen, C ₁ -C ₁₈ alkyl or C ₆ -C ₁₀ aryl; R ₈ represents hydrogen, C ₁ -C ₁₈ alkyl or C ₂ -C ₁₈ hydroxyalkyl; R ₉ represents a C ₁ -C ₁₂ alkylene or a bond; R ₁₈ is C ₁ -C ₁₂ alkyl or phenyl unsubstituted or substituted with halogen, OH, COOR ₂₁ or C (O) -R ₂₂ ; R ₂₁ represents hydrogen, an alkali metal atom, or C ₁ -C ₁₈ alkyl; R ₂₂ is C ₁ -C ₁₈ alkyl; E is a wax with a C ₈₀ -C ₈₀₀ alkyl group, where the alkyl chain of the alkyl group may contain alkyl substituents, aromatic substituents and polar groups as substituents and may be interrupted by alkene units and heteroatoms; and n is an integer from 1 to 1000. 2. The compounds of formula (A) according to claim 1, where G1 and G2, independently of one another, are preferably hydrogen, C ₁ -C ₁₈ alkyl, C ₃ -C ₁₈ alkenyl, C ₃ -C ₁₈ alkynyl, C ₇ -C ₉ phenylalkyl, C ₃ -C ₁₂ - cycloalkyl; or G1 and G2 together with the C atom to which they are attached form a C ₅ -C ₁₂ ring. 3. The compounds of formula (A) according to claim 1 or 2, where n is an integer from 1 to 20. 4. The compounds of formula (A) according to claim 1, where G1 and G2 are independently hydrogen or C ₁ -C ₁₈ alkyl; T1 represents a tertiary C ₄ -C ₁₈ -alkyl group or phenyl group; T2 represents hydrogen or a monovalent organic group containing 1-50 carbon atoms; or T2 and T1 together form a group of formula (F), where b is 0 or 1. 5. The compounds of formula (A) according to claim 1, where T1 and T2 together with the nitrogen atom N in the formula (M) and with the Quaternary atom C substituted by G1 and G2 in the formula (M), represent a tetramethylpiperidyl group. 6. The compounds of formula (A) according to claim 1, where the tetramethylpiperidyl group is one of the groups: 2,2,6,6-tetramethylpiperidine, 2,2,6,6-tetramethylpiperidin-4-one, 2,2,6,6-tetramethylpiperidin-4-ol, 4-amino-2,2,6,6-tetramethylpiperidine, 2,2,4,4-tetramethyl-7-oxa-3,20-diazadispiro [5.1.11.2] geneikosan-21-one, 2,2,4,4-tetramethyl-20-lauryloxycarbonylethyl-7-oxa-3,20-diazadispiro [5.1.11.2] -genicosan-21-one, 2,2,4,4-tetramethyl-20-myristyloxycarbonylethyl-7-oxa-3,20-diazadispiro [5.1.11.2] -genicosan-21-one, bis (2,2,6,6-tetramethyl-4-piperidinyl) sebacinate, esters of 2,2,6,6-tetramethyl-4-piperidinol and higher fatty acids, especially stearic or palmitic acid and mixtures thereof, N, N'-bis-2,2,6,6-tetramethyl-4-piperidinyl-1,3-benzenedicarboxamide, 2,2,4,4-tetramethyl-20- (β-myristyloxycarbonyl) ethyl-7-oxa-3,20-diazadispiro [5.1.11.2] geneikosan-21-one, 2,2,4,4-tetramethyl-20- (β-lauryloxycarbonyl) ethyl-7-oxa-3,20-diazadispiro [5.1.11.2] geneikosan-21-one, 3-dodecyl-1- (2,2,6,6-tetramethyl-4-piperidyl) pyrrolidin-2,5-dione, 2,2,6,6-tetramethyl-4N- (β-lauryloxycarbonyl) ethylaminopiperidine, 2,2,6,6-tetramethyl-4N- (β-myristyloxycarbonyl) ethylaminopiperidine, N, N'-1,6-hexanediylbis (N- (2,2,6,6-tetramethylpiperidin-4-yl) formamide), 2,6-bis (2,2,6,6-tetramethylpiperidin-4-yl) -1H, 4H, 5H, 8H-2,3a, 4a, 6,7a, 8a-hexaazaperhydrocyclopentafluoren-4,8-dione or 3-dodecyl-7,7,9,9-tetramethyl-1,3,8-triazaspiro [4.5] decan-2,4-dione. 7. A method of obtaining compounds of formula (A)

characterized in that at least one compound of formula (B) and / or at least one compound of formula (C),

in which G1, G2, T1 and T2 have a value similar to that defined in formula (M), in accordance with any one of claims 1 to 6, is reacted with a compound of formula (K)

in which E represents a C ₆₀ -C _1,000,000 alkyl group, where the alkyl chain of the alkyl group may contain alkyl substituents, aromatic substituents and polar groups as substituents and may be interrupted by alkene units and heteroatoms, in the presence of a hydroperoxide and a catalytic amount of a metal compound . 8. The use of compounds of formula (A) according to one or more of claims 1 to 6 for stabilizing organic material. 9. The use of claim 8 compounds as light stabilizers. 10. The use of claim 8 compounds as additives that increase fire resistance, for thermoplastic or thermoset polymers. 11. A mixture M containing components K1) and K2) and optionally component K3), where K1) is an organic material, K2) is at least one compound of formula (A) according to one or more of claims 1 to 6, and K3) represents at least one substance (S), where the substance (S) is selected from one or more groups consisting of: UV absorbers, reaction stopping agents phenolic antioxidants, joint thiostabilizers, technological additives peroxide scavengers, hydroxylamines nitrons, amine oxides polyamide stabilizers, preferably copper salts in combination with iodides, and / or phosphorus-containing compounds and salts of divalent manganese, main joint stabilizers nucleating agents, fillers and reinforcing substances, which may also consist of wood and which may also be so small that they appear transparent, additional additives, preferably lubricants, plasticizers, pigments, where the pigments can also be so small that they are transparent, rheological additives, catalysts, catalyst deactivators, fluorescent brighteners, brighteners, such as, for example, substituted and unsubstituted benzylidene or dibenzylidene sorbitol, flame retardant additives, antistatic agents or blowing agents, benzofuranones and benzoindolinones, metal deactivators, ster based stabilizers hindered amines (HAS) with substituents N-H, N-R, N-O *, N-OH or N-OR, on nitrogen piperidine, waxes.