Etheramines and their use as intermediates for polymer synthesis
AssigneeHuntsman Petrochemical Corporation
InventorsHoward P. Klein, Terry L. Renken, Martin J. Renner, Bruce L. Burton, Katty Darragas
Life of this patent
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Abstract
The present invention relates to an etheramine mixture containing a monoether diamine and its method of production by alkoxylating an initiator with an alkylene oxide to produce a precursor polyol and reductively aminating the precursor polyol to form the etheramine mixture. The etheramine mixture may be used in variety of applications including as a curing agent for an epoxy resin or as a reactant in the production of polyurea.
Claims20
An etheramine mixture comprising:
- at least 10% by weight, based on the total weight of the etheramine mixture, of a monoether amine of formula (I):
- wherein R1 and R2 are identical or different and are each, independently of one another, hydrogen or a linear or branched C1-C5 alkyl group which may be optionally substituted by one or more NH2 groups, a is an integer from 3 to 6,and X and Y are identical or different and are each, independently of one another, hydrogen, a linear or branched C1-C5 alkyl group, a linear or branched C2-C5 alkenyl group, or a substituted or unsubstituted C6-C12 aryl group, and
- wherein at least one of R1 and R2 is the linear or branched C1-C5 alkyl group which may be optionally substituted by one or more NH2 groups;
- and
- at least one polyetheramine.
A process for preparing an etheramine mixture comprising:
- (i) charging an initiator to an alkoxylation reaction zone;
- (ii) contacting the initiator with an alkylene oxide in the alkoxylation reaction zone to provide a precursor polyol, wherein the alkoxylation reaction zone is maintained at a temperature from about 50° C. to about 150 ° C. and a pressure ranging from about 40 psi to about 100 psi;
- and
- (iii) charging the precursor polyol to a reductive amination zone and reductively aminating the precursor polyol in the presence of a reductive amination catalyst, hydrogen and ammonia to form the etheramine mixture,
- wherein the etheramine mixture contains at least 10% by weight, based on the total weight of the etheramine mixture, of a monoether amine of formula (I):
- wherein R1 and R2 are identical or different and are each, independently of one another, hydrogen or a linear or branched C1-C5 alkyl group which may be optionally substituted by one or more NH2 groups, a is an integer from 3 to 6, and X and Y are identical or different and are each, independently of one another, hydrogen, a linear or branched C1-C5 alkyl group, a linear or branched C2-C5 alkenyl group, or a substituted or unsubstituted C6-C12 aryl group,
- wherein at least one of R1 R2 is the linear or branched C1-C5 alkyl group which may optionally be substituted by one or more NH2 groups;
- and
- wherein hydrogen is used in an amount ranging from about 0.5 mole equivalents To about 10 mole equivalents of hydrogen per hydroxyl equivalent of the precursor polyol.
An etheramine mixture produced by a process comprising the steps of:
- (i) charging an initiator to an alkoxylation reaction zone;
- (ii) contacting the initiator with an alkylene oxide in the alkoxylation reaction zone to provide a precursor polyol;
- and
- (iii) charging the precursor polyol to a reductive amination zone and reductively aminating the precursor polyol in the presence of a reductive amination catalyst, hydrogen and ammonia to form the etheramine mixture,
- wherein the etheramine mixture contains;
- at least 10% by weight, based on the total weight of the etheramine mixture, of a monoether amine of formula (I):
- wherein R1 and R2 are identical or different and are each, independently of one another, hydrogen or a linear or branched C1-C5 alkyl group which may be optionally substituted by one or more NH2 groups, a is an integer from 3 to 6, and X and Y are identical or different and are each, independently of one another, hydrogen, a linear or branched C1-C5 alkyl group, a linear or branched C2-C5 alkenyl group, or a substituted or unsubstituted C6-C12 aryl group, and
- wherein at least one of R1 and R2 is the linear or branched C1 -C5 alkyl group which may be optionally substituted by one or more NH2 groups;
- and
- at least one polyetheramine.
Dependencies are inferred from the claim text.