Oxygenated aminophenol compounds and methods for preventing monomer polymerization

Patent metadata

Field	Value
Publication number	US-11866631-B2
Application number	US-202016860954-A
Country	US
Kind code	B2
Filing date	Apr 28, 2020
Priority date	Apr 29, 2019
Publication date	Jan 9, 2024
Grant date	Jan 9, 2024

Abstract

Described are compounds, compositions, and methods that include a nitrogen- and oxygen-containing aromatic compound, such as an aminophenol-based compound, which can be used for inhibiting polymerization of a monomer (e.g., styrene) composition. The compound includes a tertiary amine group wherein the nitrogen is attached to carbon-containing groups, and at least one of oxygen atom separated from the nitrogen by one or more carbon atoms. The antipolymerant can provide excellent antipolymerant activity in a monomer-containing composition.

First claim

What is claimed is:

1. A method for inhibiting the polymerization of monomers in a monomer-containing composition, the method comprising:
adding a nitrogen- and oxygen-containing aromatic antipolymerant to a composition comprising a polymerizable monomer, wherein the polymerizable monomer is (a) selected from the group consisting of acrolein, acrylonitrile, alkylated styrene, chloroprene, divinylbenzene, ethyl acrylate, ethyl methacrylate, isoprene, methyl methacrylate, methyl acrylate, α-methylstyrene, methacrylonitrile, styrene, styrene sulfonic acid, vinyl acetate, vinyltoluene, and vinylpyridine, (b) selected from the group consisting of ethylene, acetylene, methylacetylene, vinylacetylene, propylene, butene, butyne, and butadiene;
or (c) an unsaturated cyclic aliphatic compound, the nitrogen- and oxygen-containing aromatic antipolymerant being a compound of Formula I:

wherein at least one of —R 1 , —R 2 , —R 3 , —R 4 , and —R 5 is or are —OR 8 ,
wherein R 8 is selected from the group consisting of —H, alkyl, aryl, alkyl-aryl, and aryl-alkyl having 3-18 carbon atoms, wherein any one or more of —R 1 , —R 2 , —R 3 , —R 4 , and —R 5 that is not —OR 8 is or are selected from the group consisting of hydrogen, alkyl, aryl, alkyl aryl and aryl alkyl, or any two adjacent groups of —R 1 , —R 2 , —R 3 , —R 4 , and —R 5 that are not —OR 8 form one or more ring structures;
wherein R 6 and R 7 are, independently, carbon-containing groups, and at least one of R 6 and R 7 comprises one or more oxygen atom(s) separated from the N atom by one or more carbon atoms;
wherein the compound of Formula I inhibits polymerization of the polymerizable monomer in the composition.

2. The method of claim 1 wherein the one or more oxygen atom(s) is or are present in the form of a hydroxyl group, an ether group, or both.

3. The method of claim 1 wherein the one or more oxygen atom(s) is or are separated from the N atom by two or more carbon atoms.

4. The method of claim 1 , wherein one or both of R 6 and R 7 is or are of the formula: —R 9 OR 10 , wherein R 9 is a hydrocarbylene group, optionally substituted, and R 10 is a hydrocarbyl group, optionally substituted, wherein one or both of R 9 and R 10 optionally have an amount of carbon atoms in the range of 1-12, 1-8, 1-6, or 1-3.

5. The method of claim 4 wherein R 9 is selected from the group consisting of methylene, ethylene, propylene, isopropylene, butylene, isobutylene, sec-butylene, tert-butylene, pentylene, and hexylene.

6. The method of claim 4 wherein R 10 is selected from the group consisting of linear alkyl, branched alkyl, cyclic alkyl, aryl, alkyl-aryl, and aryl-alkyl, each having 1-18 carbon atoms, wherein R 10 is optionally:
methyl,
ethyl,
propyl, isopropyl,
butyl, isobutyl, sec-butyl, tert-butyl,
pentyl, cyclopentyl, isopentyl, neopentyl,
hexyl, cyclohexyl, 1-, 2-, or 3-methylbutyl, 1,1-, 1,2-, or 2,2-dimethylpropyl, 1-ethyl-propyl, 1-, 2-, 3-, or 4-methylpentyl, 1,1-, 1,2-, 1,3-, 2,2-, 2,3-, or 3,3-dimethylbutyl, 1- or 2-ethylbutyl, 1-ethyl-l-methylpropyl, 1,1,2- or 1,2,2-trimethylpropyl, methylcyclopentyl;
heptyl, 2-methylhexyl, 3-methylhexyl, 4-methylhexyl, 5-methylhexyl, 3-ethylpentyl, 2,2,3-trimethylbutyl, 2,2-dimethylpentyl, 2,3-dimethylpentyl, 2,4-dimethylpentyl, 3,3-dimethylpentyl, 3,4-dimethylpentyl, 4,4-dimethylpentyl, cycloheptyl, 1-methylcyclohexyl, 2-methylcyclohexyl;
octyl, 2-methylheptyl, 3-methylheptyl, 4-methylheptyl, 2-ethylhexyl, 3-ethylhexyl, 4-ethylhexyl, 5-ethylhexyl, 2,2-dimethylhexyl, 2,3-dimethylhexyl, 2,4-dimethylhexyl, 2,5-dimethylhexyl, 3,3-dimethylhexyl, 3,4-dimethylhexyl, 3-ethyl-2-methylpentyl, 3-ethyl-3-methylpentyl, 2,2,3-trimethylpentyl, 2,2,4-trimethylpentyl, 2,3,3-trimethylpentyl, 2,3,4-trimethylpentyl, or_2,2,3,3-tetramethylbutyl.

7. The method of claim 4 wherein the nitrogen- and oxygen-containing aromatic antipolymerant is a compound selected from the group consisting of:
4-bis[(methoxymethyl)amino]phenol, 4-bis[(2-methoxyethyl)amino]phenol, 4-bis[(3-methoxypropyl)amino]phenol, 4-bis[(4-methoxybutyl)amino]phenol, 4-bis[(5-methoxypentyl)amino]phenol, 4-bis[(6-methoxyhexyl)amino]phenol, 4-bi s[(methoxyphenyl)amino]phenol;
4-bis[(ethoxymethyl)amino]phenol, 4-bis[(2-ethoxyethyl)amino]phenol, 4-bis[(3-ethoxypropyl)amino]phenol, 4-bis[(4-ethoxybutyl)amino]phenol, 4-bis[(5-ethoxypentyl)amino]phenol, 4-bis[(6-ethoxyhexyl)amino]phenol, 4-bi s[(ethoxyphenyl)amino]phenol;
4-bis[(propoxymethyl)amino]phenol, 4-bis[(2-propoxyethyl)amino]phenol, 4-bis[(3-propoxypropyl)amino]phenol, 4-bis[(4-propoxybutyl)amino]phenol, 4-bis[(5-propoxypentyl)amino]phenol, 4-bis[(6-propoxyhexyl)amino]phenol, 4-bis[(propoxyphenyl)amino]phenol;
4-bis[(butoxymethyl)amino]phenol, 4-bis[(2-butoxyethyl)amino]phenol, 4-bis[(3-butoxypropyl)amino]phenol, 4-bis[(4-butoxybutyl)amino]phenol, 4-bis[(5-butoxypentyl)amino]phenol, 4-bis[(6-butoxyhexyl)amino]phenol, and 4-bis[(butoxyphenyl)amino]phenol.

8. The method of claim 4 , wherein R 9 is a hydroxylated hydrocarbylene group, wherein R 9 is optionally selected from the group consisting of:

or —R 9 OR 10 is selected from the group consisting of:

9. The method of claim 8 wherein the nitrogen- and oxygen-containing aromatic antipolymerant is a compound selected from the group consisting of
4-bis[(2-methoxy-l-hydroxy-ethyl)amino]phenol, 4-bis[(3-methoxy-2-hydroxy-propyl) amino]phenol, 4-bis[(4-methoxy-2-hydroxy-butyl)amino]phenol,
4-bis[(5-methoxy-2-hydroxy-pentyl)amino]phenol, 4-bis[(6-methoxy-2-hydroxy-hexyl)amino]phenol, 4-bis[(methoxyhydroxyphenyl)amino]phenol;
4-bis[(2-ethoxy-l-hydroxy-ethyl)amino]phenol, 4-bis[(3-ethoxy-2-hydroxy-propyl) amino]phenol, 4-bis[(4-ethoxy-2-hydroxy-butyl)amino]phenol, 4-bis[(5-ethoxy-2-hydroxy-pentyl)amino]phenol, 4-bis[(6-ethoxy-2-hydroxy-hexyl)amino]phenol, 4-bis[(ethoxyhydroxyphenyl)amino]phenol;
4-bis[(2-propoxy-l-hydroxy-ethyl)amino]phenol, 4-bis[(3-propoxy-2-hydroxy-propyl) amino]phenol, 4-bis[(4-propoxy-2-hydroxy-butyl)amino]phenol, 4-bis[(5-propoxy-2-hydroxy-pentyl)amino]phenol, 4-bis[(6-propoxy-2-hydroxy-hexyl) amino]phenol, 4-bis[(propoxyhydroxyphenyl)amino]phenol,
4-bis[(2-butoxy-l-hydroxy-ethyl)amino]phenol, 4-bis[(3-butoxy-2-hydroxy-propyl) amino]phenol, 4-bis[(4-butoxy-2-hydroxy-butyl)amino]phenol, 4-bis[(5-butoxy-2-hydroxy-pentyl)amino]phenol, 4-bis[(6-butoxy-2-hydroxy-hexyl)amino]phenol, and 4-bis[(butoxyhydroxyphenyl)amino]phenol.

10. The method of claim 1 wherein both of R 6 and R 7 are hydroxylated hydrocarbyl groups, wherein the hydroxylated hydrocarbyl groups have an amount of carbon atoms in the range of 1-18, 1-12, 1-8, 1-6, or 1-3.

11. The method of claim 10 wherein the hydroxylated hydrocarbyl groups are selected from linear alkanol, branched alkanol, cyclic alkanol, hydroxylated aryl, hydroxylated alkyl-aryl, and hydroxylated aryl-alkyl.

12. The method of claim 11 wherein the hydroxylated hydrocarbyl formula —(CR 24 R 25 ) q (CHOH)(CH 2 ) z R 11 , wherein R 24 and R 25 are independently selected from H, R 10 , and OR 10 ), wherein q and z are independently integer in the range of 1-12, optionally integers in the range of 1-6 or 1-3, and wherein R 11 is selected from the group consisting of R 10 , and

wherein R 12 is independently selec

Assignees

• Ecolab Usa Inc

Inventors

• Masere Jonathan
• Dhawan Ashish

Classifications

• C09K15/24 Primary

  containing a phenol or quinone moiety · CPC title

• C07C7/20

  Use of additives, e.g. for stabilisation · CPC title

• C07C215/76 Primary

  of the same non-condensed six-membered aromatic ring · CPC title

• C08F2/40

  using retarding agents · CPC title

• C07C2601/16

  the ring being unsaturated · CPC title