Abstract
Hydrophobe-modified water-soluble polymers have found extensive use in the latex paint industry as thickeners and rheology modifiers.1 Hydrophobe-modified water-soluble polymers, also referred to as associative thickeners, consist of three general families of polymers: the HEUR (hydrophobe-modified ethoxylated urethane) thickeners, the HASE (hydrophobe-modified alkali-soluble emulsion) thickeners, and the HMHEC (hydrophobe-modified hydroxyethyl cellulose) thickeners.2 Because of their ease of formulation, high thickening efficiency, good tint and colorant acceptability, and good general rheology, HMHEC polymers are widely used in North America in commercial latex paints, either alone or in combination with other thickeners, and often in exterior paint formulations.
This is a preview of subscription content, log in via an institution to check access.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
Similar content being viewed by others
References
G. D. Shay and A. F. Rich, Urethane-functional alkali-soluble associative latex thickeners, J. Coatings Tech., 58 (732): 43 (1986).
J. E. Hall, P. Hodgson, L. Krivanek, and P. Malizia, Influence of rheology modifiers on the performance characteristics of latex paints, J. Coatings Tech., 58 (738): 65 (1986).
P. A. Reynolds, Association thickening of polymer latex dispersions, Prog. Org. Coatings, 20: 393 (1992).
P. R. Howard, E. L. Leasure, S. T. Rosier, and E. J. Schaller, Formulating with combinations of HEUR associative thickeners, J. Coatings Tech., 64 (804): 87 (1992).
G. D. Shay, Thickeners and rheology modifiers, in: Paint and Coating Testing Manual, J. V. Koleske, ed., 14th edition of the Gardner-Sward Handbook, ASTM, Philadelphia (1995).
A. C. Sau and L. M. Landoll, Synthesis and solution properties of hydrophobically modified hydroxyethyl cellulose, in: Polymers in Aqueous Media: Performance Through Association, J. E. Glass, ed., ACS Advances in Chemistry Series, #223, Washington, D. C. (1989).
R. A. Gelman and H. G. Barth, Viscosity studies of hydrophobically modified hydroxyethyl cellulose, in: Water-Soluble Polymers: Beauty with Performance, J. E. Glass, ed., ACS Advances in Chemistry Series, #213, Washington, D. C. (1986).
H. Yokota, Alkalization mechanism of cellulose in hydroxypropylcellulose preparation process, J. Appl. Polym.Sci., 32: 3423 (1986).
E. V. Dehmlow and S. S. Dehmlow, Phase Transfer Catalysis, 2nd. edition, Verlag Chemie, Basel (1983).
C. M. Starks and C. Liotta, Phase Transfer Catalysis: Principles and Techniques, Academic Press, New York (1978).
W. P. Weber and G. W. Gokel, Phase Transfer Catalysis in Organic Synthesis, Springer-Verlag, Berlin (1977).
J. Dockx, Quaternary ammonium compounds in organic synthesis, Synthesis, 441 (1973).
L. J. Mathias, Crown ethers and phase transfer catalysis in polymer chemistry, J. Macromol. Sci., Chem., A15 (5): 853 (1981).
J. M. J. Fréchet, Chemical modification of halogenated polymers under phase transfer conditions, J. Macromol. Sci., Chem., A15 (5): 877 (1981).
T. Nishikubo, T. Iizawa, K. Kobayashi, and M. Okawara, Substitution reaction of poly(chloromethylstyrene) with some nucleophilic reagents using phase transfer catalysis, Makromol. Chem., Rapid Comm., 1: 765 (1980).
R. Liotta and G. Brons, Coal. Kinetics of O-alkylation, J. Am. Chem. Soc., 103: 1735 (1981).
R. Liotta, K. Rose, and E. Hippo, O-Alkylation chemistry of coal and its implications for the chemical and physical structure of coal, J. Org. Chem., 46: 277 (1981).
W. H. Daly and J. D. Caldwell, Influence of quaternary ammonium salts on cellulose benzylation, J. Polym. Sci., Polym. Lett., 17: 55 (1979).
W. H. Daly, J. D. Caldwell, K. V. Phung, and R. Tang, Influence of quaternary ammonium salts on cellulose modification, in: Crown Ethers and Phase Transfer Catalysis in Polymer Science, L. J. Mathias and C. E. Carraher, ed., Plenum Press, New York (1984).
CELLOSIZE® is Union Carbide’s trademark for its hydroxyethyl cellulose (HEC) polymer.
E. M. Partain, U. S. Patent 5,504,123, Dual Functional Cellulosic Additives for Latex Compositions, April 2, 1996.
E. M. Partain, U. S. Patent 5,583,214, Dual Functional Cellulosic Additives for Latex Compositions, December 10, 1996.
A. C. Cope and E. R. Trumbull, Olefins from amines: the Hofmann elimination reaction and amine oxide pyrolysis, Organic Reactions, 11: 317 (1960).
3-n-Pentadecenyl phenyl glycidyl ether is a commercial product of the Cardolite Corporation, sold under the tradename CARDOLITE® NC-513.
L. Shechter, J. Wynstra, and R. E. Kurkjy, Glycidyl ether reactions with amines, Ind. Eng. Chem., 48: 94 (1956).
L. Shechter, J. Wynstra, and R. E. Kurkjy, Chemistry of styrene oxide, Ind. Eng. Chem., 49: 1107 (1957).
W. J. Belanger and J. H. Denham, The catalyzed reactions of various glycidyl ether compounds with amines, acids, phenols, and alcohols, ACS Preprints, Division of Paint, Plastics, and Printing Ink Chemistry, 18(2): 10 (1958).
R. E. Parker and N. S. Issacs, Mechanisms of epoxide reactions, Chem. Rev., 59: 737 (1959).
J. Murto, Hydroxide-alkoxide ion equilibria and their influence on chemical reactions, in: The Chemistry of Hydroxyl Groups, S. Patai, ed. John Wiley & Sons, New York (1971).
E. M. Partain, G. L. Brode, and R. C. Hoy, European Patent Application 0 384 167, Polysaccharides with Alkyl-Aryl Aromatic Hydrophobes and Latex Compositions Containing Same, August 29, 1990.
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1997 Springer Science+Business Media New York
About this chapter
Cite this chapter
Partain, E.M. (1997). The Synthesis of Hydrophobe-Modified Hydroxyethyl Cellulose Polymers Using Phase Transfer Catalysis. In: Swift, G., Carraher, C.E., Bowman, C.N. (eds) Polymer Modification. Springer, Boston, MA. https://doi.org/10.1007/978-1-4899-1477-4_4
Download citation
DOI: https://doi.org/10.1007/978-1-4899-1477-4_4
Publisher Name: Springer, Boston, MA
Print ISBN: 978-1-4899-1479-8
Online ISBN: 978-1-4899-1477-4
eBook Packages: Springer Book Archive