A diisocyanate stabilizer, use thereof, and diisocyanate composition

Patent metadata

Field	Value
Publication number	US-2024217923-A1
Application number	US-202218555812-A
Country	US
Kind code	A1
Filing date	Mar 28, 2022
Priority date	Apr 26, 2021
Publication date	Jul 4, 2024
Grant date	—

Abstract

The present disclosure relates to a diisocyanate stabilizer, use of the diisocyanate stabilizer for stabilizing diisocyanate, and a diisocyanate composition comprising the stabilizer. The diisocyanate stabilizer comprises a sterically hindered phenol other than butylated hydroxytoluene, a thioether, and a phosphite other than triphenyl phosphite. The present disclosure aims to provide a diisocyanate stabilizer which can make diisocyanates maintain stable during long-term storage and heating condition.

First claim

1 . A diisocyanate stabilizer, comprising a sterically hindered phenol other than butylated hydroxytoluene, a thioether, and a phosphite other than triphenyl phosphite.

2 . The diisocyanate stabilizer according to claim 1 , wherein the sterically hindered phenol is present in an amount of 10 to 90 wt %, the thioether is present in an amount of 5 to 80 wt %, and the phosphite is present in an amount of 5 to 80 wt %, based on the total weight of the diisocyanate stabilizer.

3 . The diisocyanate stabilizer according to claim 1 , consisting of a sterically hindered phenol, a thioether and a phosphite.

4 . The diisocyanate stabilizer according to claim 1 , wherein the diisocyanate stabilizer has a melting point of lower than 50° C., preferably lower than 20° C.

5 . The diisocyanate stabilizer according to claim 1 , wherein the sterically hindered phenol is at least one selected from a group consisting of alkylphenols, bisphenol A, bisphenol F, bisphenol B, bisphenol C, bisphenol S, 3,3′,5,5′-tetrabromobisphenol A, methyl 3,5-di-tert-butyl-4-hydroxybenzoate, 4-tert-butylpyrocatechol, 2-hydroxybenzyl alcohol, 2-methoxy-4-methylphenol, n-octadecyl β-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate, 1,1,3-tris-(2-methyl-4-hydroxy-5-tert-butylphenyl)butane, 1,3,5-trimethyl-2,4,6-tris(3,5-di-tert-butyl-4-hydroxybenzyl)benzene, 1,3,5-tris-(3,5-di-tert-butyl-4-hydroxybenzyl) isocyanurate, 1,3,5,-tris-(3,5-di-tert-butyl-4-hydroxyphenyl)propionyloxyethyl isocyanurate, 1,3,5-tris-(2,6-dimethyl-3-hydroxy-4-tert-butylbenzyl) isocyanurate or pentaerythritol tetrakis[β-(3,5,-di-tert-butyl-4-hydroxyphenyl)propionate], 2,6-di-tert-butyl-4-dimethylaminomethylphenol, 6-isobutyl-2,4-dinitrophenol, 6-sec-butyl-2,4-dinitrophenol, 2,6-ditert-butyl-4-(4,6-bis(octylthio)-1,3,5-triazin-2-ylamino) phenol, octadecyl 3-(3′,5′-di-tert-butyl-4′-hydroxyphenyl)propionate, hexadecyl 3-(3′,5′-di-tert-butyl-4′-hydroxyphenyl)propionate, octyl 3-(3′,5′-di-tert-butyl-4′-hydroxyphenyl)propionate, thiodiethylenebis[3-[3,5-di-tert-butyl-4-hydroxyphenyl]propionate], 4,8-dioxa-1,11-undecanediol bis[(3′,5′-di-tert-butyl-4′-hydroxyphenyl)propionate], 4,8-dioxa-1,11-undecanediol bis[(3′-tert-butyl-4′-hydroxy-5′-methylphenyl)propionate], 1,9-nonanediol bis[(3′,5′-di-tert-butyl-4′-hydroxyphenyl)propionate], 1,7-heptanediaminebis[3-(3′,5′-di-tert-butyl-4′-hydroxyphenyl)propionamide], 1,1-methanediaminebis[3-(3′,5′-di-tert-butyl-4′-hydroxyphenyl)propionamide], 3-(3′,5′-di-tert-butyl-4′-hydroxyphenyl)propionoic hydrazide, 3-(3′,5′-dimethyl-4′-hydroxyphenyl)propionoic hydrazide, bis(3-tert-butyl-5-ethyl-2-hydroxyphen-1-yl)methane, bis(3,5-di-tert-butyl-4-hydroxyphen-1-yl)methane, bis[3-(l′-methylcyclohex-1′-yl)-5-methyl-2-hydroxyphen-1-yl]methane, bis(3-tert-butyl-2-hydroxy-5-methylphen-1-yl)methane, 1,1-bis(5-tert-butyl-4-hydroxy-2-methylphen-1-yl)ethane, bis(5-tert-butyl-4-hydroxy-2-methylphen-1-yl) sulfide, bis(3-tert-butyl-2-hydroxy-5-methylphen-1-yl) sulfide, 1,1-bis(3,4-dimethyl-2-hydroxyphen-1-yl)-2-methylpropane, 1,1-bis(5-tert-butyl-3-methyl-2-hydroxyphen-1-yl)butane, 1,3,5-tris[1′-(3″,5″-di-tert-butyl-4″-hydroxyphen-1″-yl)-meth-1′-yl]-2,4,6-trimethylbenzene, 1,1,4-tris(5′-tertbutyl-4′-hydroxy-2′-methylphen-1′-yl)butane, aminophenols, nitrosophenols, alkoxyphenols, eugenol, dihydroeugenol, isoeugenol, tocopherols, tocol, α-tocopherolhydroquinone, 4-methylpyrocatechol, 3-methylpyrocatechol, hydroquinone monobenzyl ether, p-phenoxyphenol, hydroquinone, tert-butylhydroquinone, 2,5-di-tert-butylhydroquinone, 2-methyl-p-hydroquinone, 2,3-dimethylhydroquinone, trimethylhydroquinone, 2,5-di-tert-amylhydroquinone, 2,3-dihydro-2,2-dimethyl-7-hydroxybenzofuran (2,2-dimethyl-7-hydroxycoumaran), 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid, and derivatives thereof.

6 . The diisocyanate stabilizer according to claim 1 , wherein the sterically hindered phenol is at least one selected from a group consisting of 3,5-bis(1,1-dimethylethyl)-4-benzenepropanoic acid, branched C 7 -C 9 -alkyl ester, octadecyl 3-(3,5-di-tertbutyl-4-hydroxyphenyl) propionate, 3,5-bis(1,1-dimethylethyl)-4-hydroxy-benzenepropanoic acid, branched C 13 -C 15 -alkyl esters, esters of polyglycol ether terminated with phenol derivatives, 2,4-dimethyl-6-(1-methylpentadecyl)-phenol and 4,6-bis(octylthiomethyl)-o-cresol.

7 . The diisocyanate stabilizer according to claim 1 , wherein the thioether is at least one selected from formula (III)

wherein
R 4 is selected from C 1 -C 20 -alkylene or C 3 -C 12 -cycloalkylene, optionally substituted by hydroxy, amino, aryl, alkyl, aryloxy, alkyloxy, alkylthio, alkoxycarbonyl, nitro, acyl, carbocycles, heteroatoms and/or heterocycles, and
R 5 is selected from C 1 -C 18 -alkyl, C 2 -C 18 -alkyl, which is interrupted by one or more oxygen and/or sulfur atoms and/or one or more substituted or unsubstituted imino groups, C 6 -C 12 -aryl or C 5 -C 12 -cycloalkyl, which are optionally substituted by hydroxy, amino, aryl, alkyl, aryloxy, alkyloxy, alkylthio, alkoxycarbonyl, nitro, acyl, carbocycles, heteroatoms and/or heterocycles.

8 . The diisocyanate stabilizer according to claim 1 , wherein the thioether is at least one selected from a group consisting of didodecyl 3,3′-thiodipropionate, dioctadecyl 3,3′-thiodipropionate, ditridecyl 3,3′-thiodipropionate, dimyristyl thiodipropionate and 2,2-bis[[3-(dodecylthio)-1-oxopropoxy]methyl]propane-1,3-diyl bis[3-(dodecylthio)propionate].

9 . The diisocyanate stabilizer according to claim 1 , wherein the phosphite is at least one selected from formula (IV)

wherein
R 6 , R 7 and R 8 are each independently selected from C 1 -C 18 -alkyl, C 6 -C 12 -aryl or C 5 -C 12 -cycloalkyl, which are optionally substituted by hydroxy, amino, aryl, alkyl, aryloxy, alkyloxy, alkylthio, alkoxycarbonyl, nitro, acyl, carbocycles, heteroatoms and/or heterocycles.

10 . The diisocyanate stabilizer according to claim 1 , wherein the phosphite is polymeric phosphites having a structure of formula (V)

wherein
each R 9 , R 10 , R 11 and R 12 can be the same or different and independently selected from the group consisting of C1-20 alkyl, C3-22 alkenyl, C6-40 cycloalkyl, C7-40 cycloalkylene, C1-20 methoxy alkyl glycol ethers, C1-20 alkyl glycol ethers, and/or Y—OH (serving as an end capping moiety);
Y is selected from the group consisting of C2-40 alkylene, C2-40 alkyl lactone, (e.g., ethylene, propylene, caprylactone), —R 13 —N(R 14 )—R 15 — (e.g., C2-40 alkyl diamines and C2-40 alkyl triamines),
wherein R 13 , R 14 and R 15 are independently selected from the group previously defined for R 9 , R 10 , R 11 and R 12 , now further including H;
m is an integral value ranging from 2 to 100; and
x is an integral value ranging from 1 to 1,000.

11 . The diisocyanate stabilizer according to claim 10 , wherein the polymeric phosphites are polymeric diphosphites having a structure of formula (VI)

wherein
each R 9 , R 10 , R 11 and R 12 can be the same or different and independently selected from the group consisting of C1-20 alkyl, C3-22 alkenyl, C6-40 cycloalkyl, C7-40 cycloalkylene, C1-20 methoxy alkyl glycol ethers, C1-20 alkyl glycol ethers, and/or Y—OH (serving as an end capping moiety);
Y is selected from the group cons

Assignees

• Basf Se
• Basf China Co Ltd

Inventors

• Yuan Guo Liang
• Ishaque Michael
• Jin Shun Ying
• Wang Ke
• Zheng yi zhou

Classifications

• C07C265/14 Primary

  containing at least two isocyanate groups bound to the same carbon skeleton · CPC title

• C07C263/18 Primary

  Separation; Purification; Stabilisation; Use of additives · CPC title