Stabilized compositions comprising leuco compounds

Patent metadata

Field	Value
Publication number	US-11261403-B2
Application number	US-201916523650-A
Country	US
Kind code	B2
Filing date	Jul 26, 2019
Priority date	Jul 27, 2018
Publication date	Mar 1, 2022
Grant date	Mar 1, 2022

Abstract

A composition comprising: (a) a leuco composition; and (b) a stabilizing amount of an antioxidant composition. The antioxidant composition comprises at least one sterically hindered phenol and at least one substituted diarylamine, and the mole ratio of the hindered phenol to the substituted diarylamine is greater than 1:1. In another embodiment, a composition comprises (a) a leuco composition and (b) an antioxidant composition; and optionally (c) a solvent composition. The combined mass of the leuco compounds and antioxidants present in the composition is 10% or more of the total mass of the composition, and (b) the molar ratio of antioxidants present in the composition to leuco compounds present in the composition is greater than 1:1.

First claim

We claim:

1. A composition comprising: (a) a leuco composition; and (b) a stabilizing amount of an antioxidant composition which comprises at least one sterically hindered phenol and at least one substituted diarylamine, wherein (i) the leuco composition is from about 5 wt. % to about 20 wt. % of the composition and (ii) the mole ratio of the hindered phenol to the substituted diarylamine is greater than 1:1.

2. The composition of claim 1 , wherein the composition comprises about 1 wt. % or more sterically hindered phenol compounds.

3. The composition of claim 2 , wherein the mole ratio of the hindered phenol to the substituted diarylamine is greater than 5.0:1.0.

4. A composition comprising: (a) a leuco composition; and (b) an antioxidant composition, wherein (i) the combined mass of the leuco compounds and antioxidants present in the composition is 10% or more of the total mass of the composition, and (b) the molar ratio of antioxidants present in the composition to leuco compounds present in the composition is greater than 1:1.

5. The composition of claim 4 , wherein the antioxidant composition comprises at least one sterically hindered phenol and at least one substituted diarylamine.

6. The composition of claim 5 , wherein the hindered phenol is selected from the group consisting of 2,6-bis(1-methylpropyl)phenol; 2,6-bis(1,1-dimethylethyl)-4-methyl-phenol; 2-(1,1-dimethylethyl)-1,4-benzenediol; 2,4-bis(1,1-dimethylethyl)-phenol; 2,6-bis(1,1-dimethylethyl)-phenol; 3,5-bis(1,1-dimethylethyl)-4-hydroxy-benzenepropanoic acid, methyl ester; 2-(1,1-dimethylethyl)-4-methylphenol; 2-(1,1-dimethylethyl)-4,6-dimethyl-phenol; 3,5-bis(1,1-dimethylethyl)-4-hydroxybenzenepropanoic acid, 1,1′-[2,2-bis[[3-[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]-1-oxopropoxy]methyl]-1,3-propanediyl] ester; 3,5-bis(1,1-dimethylethyl)-4-hydroxybenzenepropanoic acid, octadecyl ester; 2,2′-methylenebis[6-(1,1-dimethylethyl)-4-methylphenol; 2-(1,1-dimethylethyl)-phenol; 2,4,6-tris(1,1-dimethylethyl)-phenol; 4,4′-methylenebis[2,6-bis(1,1-dimethylethyl)-phenol; 4,4′,4″-[(2,4,6-trimethyl-1,3,5-benzenetriyl)tris(methylene)]tris[2,6-bis(1,1-dimethylethyl)-pshenol]; N,N′-1,6-hexanediylbis[3,5-bis(1,1-dimethylethyl)-4-hydroxybenzenepropanamide; 3,5-bis(1,1-dimethylethyl)-4-hydroxybenzoic acid, hexadecyl ester; P-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylphosphonic acid, diethyl ester; 1,3,5-tris[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methyl]-1,3,5-Triazine-2,4,6(1H,3H,5H)-trione; 3,5-bis(1,1-dimethylethyl)-4-hydroxybenzenepropanoic acid, 2-[3-[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]-1-oxopropyl]hydrazide; 3-(1,1-dimethylethyl)-4-hydroxy-5-methylbenzenepropanoic acid, 1,1′-[1,2-ethanediylbis(oxy-2,1-ethanediyl)] ester; 4-[(dimethylamino)methyl]-2,6-bis(1,1-dimethylethyl)phenol; 4-[[4,6-bis(octylthio)-1,3,5-triazin-2-yl]amino]-2,6-bis(1,1-dimethylethyl)phenol; 3,5-bis(1,1-dimethylethyl)-4-hydroxybenzenepropanoic acid, 1,1′-(thiodi-2,1-ethanediyl) ester; 3,5-bis(1,1-dimethylethyl)-4-hydroxybenzoic acid, 2,4-bis(1,1-dimethylethyl)phenyl ester; 3,5-bis(1,1-dimethylethyl)-4-hydroxybenzenepropanoic acid, 1,1′-(1,6-hexanediyl)ester; 3-(1,1-dimethylethyl)-4-hydroxy-5-methylbenzenepropanoic acid, 1,1′-[2,4,8,10-tetraoxaspiro[5.5]undecane-3,9-diylbis(2,2-dimethyl-2,1-ethanediyl)] ester; 3-(1,1-dimethylethyl)-□-[3-(1,1-dimethylethyl)-4-hydroxyphenyl]-4-hydroxy-□-methylbenzenepropanoic acid, 1,1′-(1,2-ethanediyl) ester; 2-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methyl]-2-butylpropanedioic acid, 1,3-bis(1,2,2,6,6-pentamethyl-4-piperidinyl) ester; 3,5-bis(1,1-dimethylethyl)-4-hydroxybenzenepropanoic acid, 1-[2-[3-[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]-1-oxopropoxy]ethyl]-2,2,6,6-tetramethyl-4-piperidinyl ester; 3,4-dihydro-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-(2R)-2H-1-benzopyran-6-ol; and mixtures thereof.

7. The composition of claim 5 , wherein the substituted diarylamine is selected from one or more compounds selected from the group consisting of:

wherein either X is N and Y is C—H, or X is C—H and Y is N; wherein G, when present, is selected from the group consisting of O, S, Se, —CH═CH—, and —(CH 2 ) n — wherein n=0, 1 or 2; and wherein at least one aryl ring is substituted with a non-H moiety;
wherein in the structure of formula (XI), R 1 , R 4 , R 5 , R 6 , R 9 , and R 10 are independently selected from H and C 1 -C 12 alkyl; R 2 and R 7 are independently H or may join together with R 3 or R 8 , respectively, to form a fused aromatic ring; R 3 and R 8 , when not so joined with R 2 or R 7 , respectively, are independently selected from the group consisting of H, C 1 -C 12 alkyl, —CF 3 , —NO 2 , —CN, —Cl, —Br, —F, C 6 -C 12 aryl, C 7 -C 12 alkaryl, —OR, —SO 2 N(R) 2 , and —N(R) 2 , wherein each R is independently selected from H, C 1 -C 12 alkyl, substituted C 1 -C 12 alkyl, C 6 -C 10 aryl, substituted C 6 -C 10 aryl, C 7 -C 12 alkaryl, substituted C 7 -C 12 alkaryl, alkyleneoxy, and polyalkyleneoxy moieties;
wherein in the structure of formulas (XII)-(XIX), R 11 , R 12 , R 14 , R 15 , R 17 , and R 18 are independently selected from H and C 1 -C 12 alkyl; R 13 and R 16 are independently selected from the group consisting of H, C 1 -C 12 alkyl, —CF 3 , —NO 2 , —CN, —Cl, —Br, —F, C 6 -C 12 aryl, C 7 -C 12 alkaryl, —OR, —SO 2 N(R) 2 , and —N(R) 2 , wherein each R is independently selected from H, C 1 -C 12 alkyl, substituted C 1 -C 12 alkyl, C 6 -C 10 aryl, substituted C 6 -C 10 aryl, C 7 -C 12 alkaryl, substituted C 7 -C 12 alkaryl, alkyleneoxy, and polyalkyleneoxy moieties.

8. The composition of claim 7 , wherein the substituted diarylamine is a compound selected from formula (XI), formula (XII), and mixtures thereof.

9. The composition of claim 6 wherein the substituted diarylamine is selected from the group consisting of 4-butyl-N-(4-methylphenyl)benzenamine; 2,4,6-trimethyl-N-(2,4,6-trimethylphenyl)benzenamine; 4-(trifluoromethyl)-N-[4-(trifluoromethyl)phenyl]-benzenamine; 4-(1,1-dimethylethyl)-N-[4-(1,1-dimethylethyl)phenyl]benzenamine; N 1 ,N 1 -dimethyl-N4-phenyl-1,4-benzenediamine; N 4 -[4-(dimethylamino)phenyl]-N 1 ,N 1 -dimethyl-1,4-benzenediamine; 4-nitro-N-(4-nitrophenyl)benzenamine; 4-methoxy-N-phenylbenzenamine; 4-methyl-N-(4-methylphenyl)benzenamine; N-phenyl-2-naphthalenamine; 4-methoxy-N-(4-methoxyphenyl)benzenamine; 4-octyl-N-(4-octylphenyl)benzenamine; N-[1,1′-biphenyl]-4-yl-[1,1′-biphenyl]-4-amine; 4-heptyl-N-(4-heptylphenyl)-benzenamine; 4-(1-phenylethyl)-N-[4-(1-phenylethyl)phenyl]-benzenamine; 4,4′-iminobisbenzonitrile; 4-nonyl-N-(4-nonylphenyl)benzenamine; N-(2,4-dimethylphenyl)-2,4-dimethylbenzenamine; 4-(1,1,3,3-tetramethylbutyl)-N-[4-(1,1,3,3-tetramethylbutyl)phenyl]benzenamine; 4-(1-methyl-1-phenylethyl)-N-[4-(1-methyl-1-phenylethyl)phenyl]benzenamine; 1,9-bis(1,1-dimethylethyl)-10H-phenothiazine; 1,9-dimethyl-10H-phenothiazine; 3,7-dichloro-10H-phenothiazine; 3,7-dimethoxy-10H-phenothiazine; 10,11-dihydro-5H-dibenz[b,f]azepine; 10H-phenoselenazine; 5H-dibenz[b,f]azepine; 10H-phenoxazine; 10H-phenothiazine; 9,10-dihydroacridine; 9H-Carbazole; 2-(trifluoromethyl)-10H-phenoxazine; 2-(1,1-dimethylethyl)-10H-phenoxazine; 3-(trifluoromethyl)-10H-phenoxazine; 3,7-bis(trifluoromethyl)-10H-phenoxazine; 3-(1,1-dimethylethyl)-10H-phenoxazine; 3-(N,N-diethylsulfonyl)-10H-phenoxazine; 10H-phenoxazine-3-carbonitrile; 3-nitro-10H-phenoxazine; 3-methoxy-10H-phenoxazine; 2,4,6,8-tetrakis(1,1-dimethylethyl)-10H-phenoxazine; 2,8-bis(1,1-dimethylethyl)-10H-phenoxazine; 3-methoxy-7-nitro-10H-phenoxazine; 7-nitro-10H

Assignees

• Milliken & Co

Inventors

• Qin Haihu
• Freund Wesley A
• Dey Sanjeev K
• Miracle Gregory S

Classifications

• C11D7/5022

  containing oxygen · CPC title

• C11D3/2079

  Monocarboxylic acids-salts thereof · CPC title

• C11D3/0084 Primary

  Antioxidants; Free-radical scavengers · CPC title

• C11D1/66

  Non-ionic compounds {(C11D1/002, C11D1/004, C11D1/008 take precedence)} · CPC title

• C11D3/40

  Dyes {; Pigments} · CPC title