Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – From carboxylic acid or derivative thereof
Patent
1995-01-03
1998-05-05
Cooney, Jr., John M.
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
From carboxylic acid or derivative thereof
252 891, 426 51, 525418, 525419, 525420, 5263031, 526304, 526307, 526312, 528190, 528327, 528363, C08G 6910, A23B 710, C08F 2054
Patent
active
057476357
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to modified polyaspartic acids obtainable by polycocondensation of aspartic acid with cocondensable compounds other than amino acids or by polymerizing monoethylenically unsaturated monomers in the presence of polyaspartic acids in the manner of a free-radically initiated graft polymerization, to processes for preparing the modified polyaspartic acids, and to the use thereof as detergent additive and water treatment agent.
Polyaspartic acid and condensates of aspartic acid with other amino acids are known.
For instance, it is stated in Nature 163 (1949), 213, that when aspartic acid is heated to 200.degree. C. it forms high molecular weight condensation products. J. Amer. Chem. Soc. 74 (1952), 5304, 5307, discloses the thermal polycondensation of aspartic acid/glutamic acid mixtures in the presence of phosphoric acid.
Arch. Biochem. Biophys. 86 (1960), 281-285, describes the polycondensation of amino acid mixtures consisting of 2 parts of glutamic acid, 2 parts of aspartic acid and one part of a mixture of other amino acids in the presence of phosphoric acid at above 100.degree. C. to form proteinoids, the yield and molecular weight of which increase with the condensation temperature. The proteinoids in question contain from 10 to 30 mol % of glutamic acid as cocondensed units. The glutamic acid units are chiefly located at the chain ends. The attainable molecular weights are of the order of 35000.
According to J. Amer. Chem. Soc. 80 (1958), 2694, a purely thermal treatment of glutamic acid results virtually quantitatively in pyroglutamic acid, which is not capable of polycondensation. However, by copolycondensation of glutamic acid with other amino acids it is possible to prepare polycondensates which contain cocondensed glutamic acid units.
Nature 190 (1961) 531, and Polym. Bull. 1 (1978) 3, 177-180, describe the thermal polycondensation of L-asparagine and isoasparagine in boiling water. The resulting polyaspartic acids have average molecular weights of up to 3000.
J. Org. Chem. 26 (1961), 1084, describes the polycondensation of N-acetylaspartic acid at 145.degree.-200.degree. C. with elimination of water and acetic acid. The product obtained is a glassy solid which has been identified as polyaspartimide. This reference also describes the polycondensation of the hydrobromide of aspartic anhydride in pyridine.
A method of using phosphoric acid for the polycondensation of DL-aspartic acid is described by Neri in J. Med. Chem. 16 (1972), 893-897. A molar ratio of phosphoric acid/aspartic acid of 0.6 produces a polyaspartimide which, dissolved in dimethylformamide, has a reduced viscosity of 45 ml/g. Subsequent reaction with ethanolamine gives a modified polyaspartic acid which is suitable for use as a plasma expander. The reaction is carried out in dimethylformamide as solvent.
Polyaspartic acids obtained by thermal polyconcondensation are useful as corrosion inhibitors for steel; cf. Surface Reactive Peptides and Polymers, C. S. Sikes and A. P. Wheeler, Dallas, 1989, ACS Symposium Series 444, Washington 1991, chapter 21.
The use of biodegradable polymers as additives in water treatment is considered to be an ecologically promising alternative to the purely synthetic polymers; cf. U.S. Pat. No. 4,534,881 and also contributions by Sikes and Wheeler in Chemical Aspects of Regulation of Mineralization, Univ. S. Alabama Publ. Services, Mobile, 1988, pages 15-20, and in Surface Reactive Peptides and Polymers (see above).
U.S. Pat. No. 4,868,287 describes mineral deposit inhibitors comprising polyanionic hydrophobic peptides having block structures. A block consists for example of 15 aspartic acid units and is bonded to a block consisting of 8 alanine units. The smallest effective peptide consists of 5 units, of which 2 are to be selected from the group of the ionic amino acids. The two blocks together should not exceed 120 units.
U.S. Pat. No. 4,534,881 describes the inhibition of inorganic or biological calcium carbonate precipitations using polyaspartate, polyglutamate and copoly
REFERENCES:
patent: 3052655 (1962-09-01), Fox et al.
patent: 3846380 (1974-11-01), Fujimoto et al.
patent: 4534881 (1985-08-01), Sikes et al.
patent: 4696981 (1987-09-01), Harada et al.
Frankel, et al., Nature, vol. 163, "Synthesis of Poly-Aspartic Acid," p. 213 Dec. 1949.
Fox, et al., Arch. Biochem. Biophys., vol. 86, "Thermal Copolymerization of Amino Acids in the Presence of Phosphoric Acid," pp. 281-285 Dec. 1960.
Harada, et al., J. Amer. Chem. Soc. vol. 80, "The Thermal Condensation of Glutamic Acid and Glycine to Linear Peptides," p. 2694, Dec. 1957.
Kovacs, et al., Nature, vol. 190, "Polypeptide Formation from Asparagine Under Hypothetically Primitive Conditions," p. 531, Dec. 1961.
Harada, et al., Polym. Bull. vol. 1 "The Aqueous Thermal Polycondensation of Asparagine and Isoasparagine and the Structure of Polyaspartic Acid," pp. 177-180. Dec. 1978.
Kovacs, et al., J. Org. Chem. vol. 26 "Chemical Studies of Polyaspartic Acids," p. 1084. Dec. 1961.
Jain, et al., Makromol. Chem., vol. 182, "Synthesis and Characterization of Random Copolymers of Aspartic Acid with Lactic Acid and Glycolic Acid," pp. 2557-2561 Dec. 1987.
Sikes, et al., ACS Symposium Series 444, "Inhibition of Calcium Carbonate and Phosphate Crystallization by Peptides Enriched in Aspartic Acid and Phosphoserine," Chapter 5, Washington, Dec. 1991.
Neri, et al., J. Med. Chem. vol. 16, Synthesis of .alpha., .beta.-Poly 893-897.
Baur Richard
Boeckh Dieter
Buechner Karl-Heinz
Funhoff Angelika
Hartmann Heinrich
BASF - Aktiengesellschaft
Cooney Jr. John M.
LandOfFree
Modified polyaspartic acids, preparation thereof and use thereof does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Modified polyaspartic acids, preparation thereof and use thereof, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Modified polyaspartic acids, preparation thereof and use thereof will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-55988