Cyclic amide initialized polyetheramine and uses thereof
View Patent ↗A polyetheramine produced from a cyclic amide initiator which is first alkoxylated and then reductively aminated to form the polyetheramine. 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 or as a fuel additive in a hydrocarbon fuel composition.
1. A polyetheramine comprising a compound having a formula (I)
wherein R is a cyclic amide group having a formula (II)
wherein n is an integer of from 3 to 15, R0 is a substituent that can replace hydrogen in any hydrocarbon portion of the cyclic amide group and is an alkyl group or an aryl group, p is an integer of from 0 to 2n and X* denotes the attachment site of the cyclic amide group to the rest of the cyclic amide initialized polyetheramine compound;
R1 and R2 are each independently hydrogen, methyl or ethyl and each R1 and R2 is independently selected in each —O—CHR1-CHR2- unit;
A is an N-alkyl amino having 1 to about 20 carbon atoms in the alkyl group; and
m is an integer ranging from about 2 to about 200.
2. The polyetheramine according to claim 1 , wherein R is the cyclic amide group having the formula (II) where n is an integer of from 3 to 12, R0 is an alkyl group and p is an integer of from 0 to 4.
3. The polyetheramine according to claim 2 , wherein R is a compound having a formula
4. The polyetheramine according to claim 2 , wherein R is a compound having a formula
5. The polyetheramine according to claim 2 , wherein R is a compound having a formula
6. The polyetheramine according to claim 1 , wherein R1 and R2 are each independently hydrogen, methyl or ethyl and each R1 and R2 is independently selected in each —O—CHR1-CHR2-unit with the proviso that at least one of R1 or R2 is hydrogen; and m is an integer ranging from about 2 to about 40.
7. The polyetheramine according to claim 6 , wherein R1 and R2 are each independently hydrogen or methyl.
8. The polyetheramine according to claim 6 , wherein R1 and R2 are each independently hydrogen or ethyl.
9. A process for producing the polyetheramine according to claim 1 comprising charging a cyclic amide having a formula
where n is an integer of from 3 to 15, R0 is a substituent that can replace hydrogen in any hydrocarbon portion of the cyclic amide and is an alkyl group or an aryl group and p is an integer of from 0 to 2n to an alkoxylation reaction zone, contacting the cyclic amide 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 a primary alkyl amine.
10. A process for producing the dispersant according to claim 9 , comprising reacting from about 0.001 mole to about 2 moles of a polyetheramine comprising a compound having a formula (I)
wherein R is a cyclic amide group having a formula (II)
wherein n is an integer of from 3 to 15, R0 is a substituent that can replace hydrogen in any hydrocarbon portion of the cyclic amide group and is an alkyl group or an aryl group, p is an integer of from 0 to 2n and X* denotes the attachment site of the cyclic amide group to the rest of the cyclic amide initialized polyetheramine compound;
R1 and R2 are each independently hydrogen, methyl or ethyl and each R1 and R2 is independently selected in each —O—CHR1-CHR2- unit;
A is or an N-alkyl amino having 1 to about 20 carbon atoms in the alkyl group; and
m is an integer ranging from about 2 to about 200 with 1 mole of the copolymer at a temperature ranging from about 50° C. to about 250° C.
11. A dispersant comprising the reaction product of a polyetheramine according to claim 1 , and an epoxy resin.
12. A process for producing the dispersant according to claim 11 , comprising reacting a polyetheramine comprising a compound having a formula (I)
wherein R is a cyclic amide group having a formula (II)
wherein n is an integer of from 3 to 15, R0 is a substituent that can replace hydrogen in any hydrocarbon portion of the cyclic amide group and is an alkyl group or an aryl group, p is an integer of from 0 to 2n and X* denotes the attachment site of the cyclic amide group to the rest of the cyclic amide initialized polyetheramine compound;
R1 and R2 are each independently hydrogen, methyl or ethyl and each R1 and R2 is independently selected in each —O—CHR1-CHR2- unit;
A is an N-alkyl amino having 1 to about 20 carbon atoms in the alkyl group; and
m is an integer ranging from about 2 to about 200 with an 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.
13. An aqueous solution comprising the dispersant according to claim 11 , wherein the dispersant is soluble in the aqueous solution to a degree of at least 40% by weight of the dispersant.
14. A hydrocarbon fuel composition comprising a hydrocarbon base fuel and the polyetheramine according to claim 1 .
15. The hydrocarbon fuel composition according to claim 14 , further comprising a supplemental fuel additive.
16. A method for preventing and/or reducing the formation of deposits in an engine comprising fueling and operating said engine with the hydrocarbon fuel composition according to claim 14 .