Tetrahydrofurfuryl alcohol initialized polyetheramines and uses thereof

Patent metadata

Field	Value
Publication number	US-2021284796-A1
Application number	US-201816612451-A
Country	US
Kind code	A1
Filing date	Jun 7, 2018
Priority date	Jun 28, 2017
Publication date	Sep 16, 2021
Grant date	—

Abstract

The present disclosure provides a non-hydrocarbyl-based alcohol initiated polyetheramine. In particular, the polyetheramine of the present disclosure is produced from a tetrahydrofurfuryl alcohol-based initiator which is alkoxylated and then reductively aminated. The polyetheramine of the present disclosure may be used in a variety of applications, such as a raw material in the synthesis of a dispersant for use in an aqueous pigment dispersion.

First claim

1 . A polyetheramine having a formula (I)

wherein R is a tetrahydrofurfuryl group or an alky-substituted tetrahydrofurfuryl group; R 1 and R 2 are each independently hydrogen, methyl or ethyl and each R 1 and R 2 is independently selected in each —O—CHR 1 —CHR 2 — unit; A is NH 2 or an N-alkyl amino having 1 to 20 carbon atoms in the alkyl group; and, m is an integer ranging from about 2 to about 200.

2 . The polyetheramine of claim 1 , wherein R is a tetrahydrofurfuryl group.

3 . The polyetheramine of claim 2 , wherein A is NH 2 .

4 . The polyetheramine of claim 1 , wherein R 1 and R 2 are each independently hydrogen, methyl or ethyl and each R 1 and R 2 is independently selected in each —O—CHR 1 —CHR 2 — unit with the proviso that at least one of R 1 or R 2 is hydrogen; and m is an integer ranging from about 5 to about 100.

5 . The polyetheramine of claim 1 , wherein R is a C 1 -C 4 alkyl-substituted tetrahydrofurfuryl group; R 1 and R 2 are each independently hydrogen, methyl or ethyl and each R 1 and R 2 is independently selected in each —O—CHR 1 —CHR 2 — unit with the proviso that at least one of R 1 or R 2 is hydrogen; A is NH 2 ; and m is an integer ranging from about 5 to about 100.

6 . A process for producing the polyetheramine of claim 1 comprising charging a tetrahydrofurfuryl alcohol or alkyl substituted tetrahydrofurfuryl alcohol to an alkoxylation reaction zone, contacting the tetrahydrofurfuryl alcohol or alkyl substituted tetrahydrofurfuryl alcohol with an alkylene oxide in the alkoxylation reaction zone for a period of time to provide an intermediate polyol, charging the intermediate polyol to a reductive amination zone, and contacting the intermediate polyol in the reductive amination zone with a reductive amination catalyst in the presence of hydrogen and ammonia or a primary alkyl amine.

7 . The process of claim 6 , wherein the intermediate polyol is contacted with the reductive amination catalyst in the presence of hydrogen and ammonia.

8 . A dispersant comprising the reaction product of a polyetheramine having a formula (I)

wherein R is a tetrahydrofurfuryl group or an alky-substituted tetrahydrofurfuryl group; R 1 and R 2 are each independently hydrogen, methyl or ethyl and each R 1 and R 2 is independently selected in each —O—CHR 1 —CHR 2 — unit; A is NH 2 ; and, m is an integer ranging from about 2 to about 200 and a copolymer comprised of polymerized units of an alkenyl aromatic monomer and an α,β-unsaturated carboxylic acid moiety.

9 . The dispersant of claim 8 , wherein the alkenyl aromatic monomer comprises styrene.

10 . The dispersant of claim 8 , wherein the α,β-unsaturated carboxylic acid moiety comprises maleic anhydride.

11 . A process for producing the dispersant of claim 8 comprising reacting from about 0.001 mole to about 2 moles of the polyetheramine with 1 mole of the copolymer at a temperature ranging from about 50° C. to about 250° C.

12 . The process of claim 11 , wherein the copolymer is comprised of polymerized units of styrene and maleic anhydride.

13 . A dispersant comprising the reaction product of a polyetheramine having a formula (I)

wherein R is a tetrahydrofurfuryl group or an alky-substituted tetrahydrofurfuryl group; R 1 and R 2 are each independently hydrogen, methyl or ethyl and each R 1 and R 2 is independently selected in each —O—CHR 1 —CHR 2 — unit; A is NH 2 ; and, m is an integer ranging from about 2 to about 200 and an epoxy resin.

14 . The dispersant of claim 13 , wherein the epoxy resin comprises a compound having the formula

wherein R 1 is an alkyl group, an aryl group or an arylalkyl group.

15 . A process for producing the dispersant of claim 13 comprising reacting the polyetheramine with the epoxy resin at an epoxy equivalent:amine equivalent ratio of between about 1.10:1 to about 5:1 and at a temperature ranging from about 20° C. to about 200° C.

16 . A process for producing the dispersant of claim 13 comprising reacting the polyetheramine with the epoxy resin at a temperature ranging from about 20° C. to about 200° C. and wherein the polyetheramine is present in an amount that is stoichiometrically equal to or greater than the amount of epoxide in the epoxy resin.

17 . An aqueous solution comprising the dispersant of claim 8 , wherein the dispersant is soluble in the aqueous solution to a degree of at least 40% by weight of the dispersant.

18 . An aqueous solution comprising the dispersant of claim 13 , wherein the dispersant is soluble in the aqueous solution to a degree of at least 40% by weight of the dispersant.

19 . An aqueous pigment dispersion comprising the dispersant of claim 8 , a pigment and a solvent component.

20 . An aqueous pigment dispersion comprising the dispersant of claim 13 , a pigment and a solvent component.

Assignees

• Huntsman Petrochemical Llc

Inventors

• Zhao Haibo
• Fang Xiaohua

Classifications

• C08G65/3255 Primary

  Ammonia · CPC title

• C08L63/00

  Compositions of epoxy resins; Compositions of derivatives of epoxy resins · CPC title

• C08G65/36

  Furfuryl alcohol · CPC title

• C08F222/06

  Maleic anhydride · CPC title

• C08L71/02

  Polyalkylene oxides · CPC title