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Process for the preparation of pyrrolidonecarboxylic acid/metal/amine complexes

Assignee: BASF Corp
•
Filing: 1978-10-31
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Granted: 1980-08-26
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Expires: 1998-10-31
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Abstract

Abstract A process for the preparation of pyrrolidone-5-carboxylic acid/metal salt/amine complexes by reacting 1 mol of a L-glutamic acid lower alkyl ester/metal salt complex with 1 mol of an aliphatic, cycloaliphatic or aromatic-aliphatic damine or 2 mols of an aliphatic or cycloaliphatic monoamine in a polar solvent, with the elimination of 2 mols of alcohol. The complex compounds prepared according to the invention are valuable curing agents for epoxide resins.

Inventors

  • 👤 Friedrich Stockinger
  • 👤 Friedrich Lohse

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-09 18:10
CPC Classifications
C; C07; C07D; C07D207/00; C07D207/02; C07D207/18; C07D207/22; C07D207/24; C07D207/26; C07D207/273; C07D207/277; C07D207/28

Claims Analysis

Total Claims: 8
Claim 1
Independent Claim 223 words
A process for the preparation of a pyrrolidone-5-carboxylic acid/metal salt/amine complex of the formula (Ia) in which Me 2+ is a divalent metal cation and, if R 1 and R 2 are each a hydrogen atom, R is one of the following radicals ##STR17## in which b is a number from 10 to 50 and the sum of a and c is a number from 2 to 4, ##STR18## and, if R 1 is a hydrogen atom and R 2 is an alkyl having 1 to 4 C atoms, cyclohexyl, benzyl, 2-aminoethyl or 3-aminopropyl, or if R 1 and R 2 are each an alkyl having 1 to 4 C atoms, cyclohexyl or benzyl, R is an ethylene or propylene radical, and in which R 3 is an alkyl having 2 to 12 C atoms, 2-hydroxyethyl, 2-hydroxypropyl, benzyl, cyclohexyl or cyclopentyl, which comprises reacting 1 mol of a L-glutamic acid ester/metal complex of the formula II ##STR19## in which R 4 is an alkyl having 1 to 4 C atoms, cyclohexyl or benzyl with 1 mol of a diamine of the formula IIIa R.sub.1 --NH--R--NH--R.sub.2 (IIIa) or with 2 mols of a monoamine of the formula IIIb NH.sub.2 --R.sub.3 (IIIb) in a polar organic solvent and in the temperature range from 60° to 180° C., with the elimination of 2 mols of alcohol.
Claim 2
Dependent Claim 223 words
A process for the preparation of a pyrrolidone-5-carboxylic acid/metal salt/amine complex of the formula (Ia) in which Me 2+ is a divalent metal cation and, if R 1 and R 2 are each a hydrogen atom, R is one of the following radicals ##STR17## in which b is a number from 10 to 50 and the sum of a and c is a number from 2 to 4, ##STR18## and, if R 1 is a hydrogen atom and R 2 is an alkyl having 1 to 4 C atoms, cyclohexyl, benzyl, 2-aminoethyl or 3-aminopropyl, or if R 1 and R 2 are each an alkyl having 1 to 4 C atoms, cyclohexyl or benzyl, R is an ethylene or propylene radical, and in which R 3 is an alkyl having 2 to 12 C atoms, 2-hydroxyethyl, 2-hydroxypropyl, benzyl, cyclohexyl or cyclopentyl, which comprises reacting 1 mol of a L-glutamic acid ester/metal complex of the formula II ##STR19## in which R 4 is an alkyl having 1 to 4 C atoms, cyclohexyl or benzyl with 1 mol of a diamine of the formula IIIa R.sub.1 --NH--R--NH--R.sub.2 (IIIa) or with 2 mols of a monoamine of the formula IIIb NH.sub.2 --R.sub.3 (IIIb) in a polar organic solvent and in the temperature range from 60° to 180° C., with the elimination of 2 mols of alcohol.
Claim 3
Dependent Claim 120 words
A process according to claim 1, wherein compounds of the formula IIIa or IIIb are used in which, if R 1 and R 2 are each a hydrogen atom, R is one of the following radicals ##STR20## in which y is a number from 2 to 35, ##STR21## and, if R 1 is a hydrogen atom and R 2 is an alkyl having 1 to 4 C atoms, cyclohexyl, benzyl, 2-aminoethyl or 3-aminopropyl, or if R 1 and R 2 are each an alkyl having 1 to 4 C atoms, cyclohexyl or benzyl, R is an ethylene or propylene radical, and in which R 3 is an alkyl having 2 to 12 C atoms, 2-hydroxyethyl, 2-hydroxypropyl, benzyl, cyclohexyl or cyclopentyl.
Claim 4
Dependent Claim 30 words
A process according to claim 1, wherein compounds of the formula II are used in which Me 2+ is a divalent metal cation of Zn, Co, Ni, Cu or Cd.
Claim 5
Dependent Claim 28 words
A process according to claim 1, wherein compounds of the formula II are used in which R 4 is an alkyl radical having 1 to 4 C atoms.
Claim 6
Dependent Claim 70 words
A process according to claim 1, wherein compounds of the formula IIIa are used in which R 1 and R 2 are each a hydrogen atom and R is one of the radicals ##STR22## in which y is a number from 3 to 35, or in which R 1 is a hydrogen atom and R 2 is cyclohexyl, benzyl, 2-aminoethyl or 3-aminopropyl and R is an ethylene or propylene radical.
Claim 7
Dependent Claim 74 words
A process according to claim 1, wherein compounds of the formula IIIa are used in which R 1 and R 2 are each a hydrogen atom and R is a radical of the formula --CH.sub.2 --CH.sub.2).sub.x in which x is a number from 1 to 5, or in which R 1 is a hydrogen atom and R 2 is a cyclohexyl or benzyl, 2-aminoethyl or 3-aminopropyl and R is an ethylene or propylene radical.
Claim 8
Dependent Claim 30 words
A process according to claim 1, wherein a compound of the formula IIIb is used in which R 3 is an alkyl having 1 to 4 C atoms or 2-hydroxyethyl.

References Cited (Backward Citations)

US2819233A Cited
US2915540A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1983-08-26 1984-02-25 1984-08-26 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1987-08-26 1988-02-25 1988-08-26 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1991-08-26 1992-02-25 1992-08-26 $7700.00 Window Closed / Lapsed

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