Abstract
The usage of acrylic esters as building blocks for polymers of industrial importance began in earnest with the research of Otto Röhm. The first recorded preparation of the basic building block for acrylic ester polymers, acrylic acid, took place in 1843; this synthesis relied on the air oxidation of acrolein. The first acrylic acid derivatives to be made were methyl acrylate and ethyl acrylate. Although these two monomers were synthesized in 1873, their utility in the polymer area was not discovered until 1880 when Kahlbaum polymerized methyl acrylate and tested its thermal stability. To his surprise, the polymerized methyl acrylate did not depolymerize at temperatures up to 320°C. Despite this finding of incredibly high thermal stability, the industrial production of acrylic ester polymers was not realized for almost another 50 years.
The commercial discovery of acrylic ester polymers took place while Otto Röhm was conducting his doctoral research in 1901. Röhm obtained a U.S. patent in 1912 covering the vulcanization of acrylates with sulfur. Commercial production of acrylic ester polymers by the Rohm and Haas Co. of Darmstadt, Germany, commenced in 1927.
Bibliography
“Acrylic Ester Polymers” in EPST 1st ed., Vol. 1, pp. 246-328, by L. S. Luskin and R. J. Myers, Rohm and Haas Co.; “Acrylic and Methacrylic Polymers” in EPST 2nd ed., Vol. 1, pp. 211-299, by B. B. Kine and R. W. Novak, Rohm and Haas Co; “Acrylic Ester Polymers” in EPST 3rd ed., Vol. 1, pp. 96-124, by Robert V. Slone, Rohm and Haas Co; in EPST (Online) Posting Date: October 22, 2001, by Robert V. Slone, Rohm and Haas Co
Cited References
- 1 J. Redtenbacher, Ann. 47, 125 (1843).
- 2 Fr. Englehorn, Berichte 13, 433 (1880); L. Balbiano and A. Testa, Berichte 13, 1984 (1880).
- 3 W. Caspary and B. Tollens, Ann. 167, 241 (1873).
- 4
G. W. A. Kahlbaum,
Berichte
13,
2348
(1880).
10.1002/cber.188001302269 Google Scholar
- 5U.S. Pat. 1,121,134 (Dec. 15, 1914), O. Röhm.
- 6 E. H. Riddle, Monomeric Acrylic Esters, Reinhold Publishing Corp., New York, 1954.
- 7 J. Brandrup, H. Immergut, A. Edmund, E. Grulke, A. Akihiro, D. R. Bloch, Polymer Handbook, 4th ed., John Wiley & Sons, New York, 2005.
- 8 H. B. Burrell, Off. Dig. Fed. Soc. Paint Technol. 131 (Feb. 1962).
- 9 D. W. van Krevelen, Properties of Polymers, Elsevier, Amsterdam, 1972.
- 10 J. L. Gardon, in N. M. Bikales, ed., Encyclopedia of Polymer Science and Technology, Vol. 3, Interscience Publishers, a division of John Wiley & Sons, Inc., New York, 1965, pp. 833–862.
- 11 T. G. Fox Jr., Bull. Am. Phys. Soc. 1 (3), 123 (1956).
- 12 J. A. Shetter, J. Polym. Sci., Part B 1, 209 (1963).
- 13 L. E. Nielsen, Mechanical Properties of Polymers, Van Nostrand Reinhold Co., Inc., New York, 1962, p. 122.
- 14 I. Williamson, Br. Plast. 23, 87 (1950).
- 15
R. F. Clark Jr. and
R. M. Berg,
Ind. Eng. Chem.
34,
1218
(1942).
10.1021/ie50385a021 Google Scholar
- 16 ASTM Standards, ASTM D1043-61T, Vol. 27, American Society for Testing and Materials, Philadelphia, Pa., 1964.
- 17 S. D. Gehman, D. E. Woodford, and C. S. Wikinson Jr., Ind. Eng. Chem. 39, 1108 (1947).
- 18 ASTM Standards, ASTM D1053-61, Vol. 19, American Society for Testing and Materials, Philadelphia, Pa., 1974.
- 19 A. C. Nuessle and B. B. Kine, Ind. Eng. Chem. 45, 1287 (1953).
- 20 A. C. Nuessle and B. B. Kine, Am. Dyest. Rep. 50 (26), 13 (1961).
- 21 V. J. Moser, Am. Dyest. Rep. 53 (38), 11 (1964).
- 22 M. K. Lindemann, Appl. Polym. Symp. 10, 73 (1969).
- 23 W. H. Brendley Jr., Paint Varn. Prod. 63 (3), 23 (1973).
- 24 R. Zdanowski and G. L. Brown Jr., Resin Review, Vol. 9, No. 1, Rohm and Haas Co., Philadelphia, Pa., 1959, p. 19.
- 25 R. Bakule and J. M. Blickensderfer, Tappi 56 (4), 70 (1973).
- 26
A. V. Tobolsky,
J. Polym. Sci., Polym. Symp.
9,
157
(1975).
10.1002/polc.5070090110 Google Scholar
- 27 L. J. Hughes and G. E. Britt, J. Appl. Polym. Sci. 5 (15), 337 (1961).
- 28 S. Krause and N. Roman, J. Polym. Sci., Part A 3, 1631 (1965).
- 29 H. L. Gerhart, Off. Dig. Fed. Soc. Paint Technol. 680 (June 1961).
- 30 R. M. Christenson and D. P. Hart, Off. Dig. Fed. Soc. Paint Technol. 684 (June 1961).
- 31 H. A. Vogel and H. G. Brittle, Off. Dig. Fed. Soc. Paint Technol. 699 (June 1961).
- 32 J. D. Murdock and G. H. Segall, Off. Dig. Fed. Soc. Paint Technol. 709 (June 1961).
- 33 J. D. Petropoulous, C. Frazier, and L. E. Cadwell, Off. Dig. Fed. Soc. Paint Technol. 719 (June 1961).
- 34 D. G. Applegath, Off. Dig. Fed. Soc. Paint Technol. 737 (June 1961).
- 35U.S. Pat. 2,886,474 (May 12, 1959), B. B. Kine and A. C. Nuessle (to Rohm and Haas Co.).
- 36U.S. Pat. 2,923,653 (Feb. 2, 1960), N. A. Matlin and B. B. Kine (to Rohm and Haas Co.).
- 37 D. H. Klein, J. Paint Technol. 42 (545), 335 (1970).
- 38 S. H. Rider and E. E. Hardy, Polymerization and Polycondensation Processes (Adv. Chem. Ser. No. 34), American Chemical Society, Washington, D.C., 1962.
- 39 R. H. Wiley and G. M. Braver, J. Polym. Sci. 3, 647 (1948).
- 40 J. R. Martin, J. F. Johnson, and A. R. Cooper, J. Macrol. Sci. Rev. Macromol. Chem. 8, 57 (1972).
- 41 A. S. Craemer, Kunststoffe 30, 337 (1940).
- 42 B. E. Rehberg and C. H. Fisher, Ind. Eng. Chem. 40, 1429 (1948).
- 43 G. G. Cameron and D. R. Kane, Makromol. Chem. 109, 194 (1967).
- 44 L. Gunawan and J. K. Haken, J. Polym. Sci., Polym. Chem. Ed. 23, 2539 (1985).
- 45 A. R. Burgess, Chem. Ind. 78 (1952).
- 46
R. Stelle and
H. Jacobs,
J. Appl. Polym. Sci.
2
(4),
86
(1959).
10.1002/app.1959.070020413 Google Scholar
- 47 B. G. Achhammer, Mod. Plast. 35, 131 (1959).
- 48 K. L. Hoy, J. Paint Technol. 43, 76 (1970).
- 49 A. F. M. Martin, Handbook of Solubility Parameters and Other Cohesion Parameters, CRC Press, Inc., Boca Raton, Fla., 1983.
- 50 J. H. Hildebrand and R. L. Scott, The Solubility of Non-Electrolytes, 3rd ed., Rheinhold Publishing Corp., New York, 1949.
- 51 P. A. Small, J. Appl. Chem. 3, 71 (1953).
- 52 H. Burrell, Off. Dig. Fed. Soc. Paint Technol. 726 (Oct. 1955).
- 53 J. L. Gardon, J. Paint Technol. 38, 43 (1966).
- 54 A. Rudin and H. K. Johnston, J. Paint Technol. 43 (559), 39 (1971).
- 55 T. P. Forbarth, Chem. Eng. 69 (5), 96 (1962).
- 56 M. Salkind, E. H. Riddle, and R. W. Keefer, Ind. Eng. Chem. 51, 1328 (1959).
- 57 H. Warson, The Applications of Synthetic Resin Emulsions, Ernest Benn Ltd., London, 1972.
- 58 R. F. B. Davies and G. E. J. Reynolds, J. Appl. Polym. Sci. 12, 47 (1968).
- 59 A. R. Burgess, Chem. Ind. 78 (1952).
- 60 M. Tabata, G. Nilsson, and A. Lund, J. Polym. Sci., Polym. Chem. Ed. 21, 3257 (1983).
- 61 R. K. Graham, J. Polym. Sci. 38, 209 (1959).
- 62 W. Burlant, J. Minsch, and C. Taylor, J. Polym. Sci., Part A 2, 57 (1964).
- 63 S. Sakuyama and co-workers, Chem. Technol. 350 (June 1973).
- 64 F. T. Maler and W. Bayer, Encycl. Chem. Process Des. 1, 401 (1976).
- 65 D. J. Hadley and E. M. Evans, Propylene and Its Industrial Derivatives, John Wiley & Sons, Inc., New York, 1973, pp. 416–497.
- 66U.S. Pat. 3,875,212 (1975), T. Ohrui (to Sumitomo Chemical).
- 67 S. Schulze and H. Vogel, Chemical Engineering & Technology 21 (10), 829-837 (1998).
- 68 Analytical Methods for the Acrylic Monomers, CM-18, Rohm and Haas Co., Philadelphia, Pa.
- 69 Acrylate Monomers, Bulletin F-40252, Union Carbide Corp., New York.
- 70 Celanese Acrylates, Product Manual N-70-1, Celanese Chemical Co., New York.
- 71
D. Quigley,
F. Simmons,
H. Whyte,
J. Robertson, and
D. Freshwater,
J. Chem. Health Safety
17
(1),
29-53
(2010).
10.1016/j.jchas.2009.04.001 Google Scholar
- 72 UCB Chemicals Corp., J. Coatings Technol., 69 (871), 83-89 (1997).
- 73 G. M. Burnett and L. D. Loan, International Symposium on Macromolecular Chemistry, Prague, 1957, p. 113.
- 74U.S. Pats. 2,367,660 and 2,367,661 (Jan. 23, 1945), C. L. Agre (to E. I. du Pont de Nemours & Co., Inc.).
- 75 A. Chapiro, Radiative Chemistry of Polymeric Systems, Wiley-Interscience, New York, 1972.
- 76 Preparation, Properties and Uses of Acrylic Polymers, CM-19, Rohm and Haas Co., Philadelphia, Pa.
- 77 T. G. Fox Jr. and R. Loshock, J. Am. Chem. Soc. 75, 3544 (1953).
- 78 J. L. O'Brien, J. Am. Chem. Soc. 77, 4757 (1955).
- 79 E. P. Bonsall, Trans. Faraday Soc. 49, 686 (1953).
- 80 P. G. Griffiths and co-workers, Tetrahedron Lett. 23, 1309 (1982).
- 81 G. V. Schulz and G. Henrici, Makromol. Chem. 18/19, 473 (1956).
- 82 F. R. Mayo and A. A. Miller, J. Am. Chem. Soc. 80, 2493 (1956).
- 83
M. M. Mogilevich,
Russ. Chem. Rev.
48,
199
(1979).
10.1070/RC1979v048n02ABEH002314 Google Scholar
- 84 D. A. Tirrell, in J. I. Kroschwitz, ed., Encyclopedia of Polymer Science and Engineering, Wiley-Interscience, New York, 1986, pp. 192–233.
- 85 O. Yoshiahi and T. Imato, Rev. Phys. Chem. Jpn. 42 (1), 34 (1972).
- 86 F. W. Billmeyer Jr., Textbook of Polymer Chemistry, Interscience Publishers, New York, 1957.
- 87 Emulsion Polymerization of Acrylic Monomers, CM-104, Rohm and Haas Co., Philadel-phia, Pa.
- 88 J. J. Uibel and F. J. Dinon, J. Polym. Sci., Polym. Chem. Ed. 21, 1773 (1983).
- 89 F. A. Bovey, High Resolution NMR of Macromolecules, Academic Press, New York, 1972.
- 90 M. S. Matheson and co-workers, J. Am. Chem. Soc. 73, 5395 (1951).
- 91 T. G. Fox and R. Gratch, Ann. N.Y. Acad. Sci. 57, 367 (1953).
- 92 L. Maduga, An. Quim. 65, 993 (1969).
- 93 P. G. Griffiths, E. Rizzardo, and D. H. Solomon, J. Macromol. Sci., Chem. 17, 45 (1982).
- 94 J. G. Kloosterboer and H. L. Bressers, Polym. Bull. 2, 205 (1982).
- 95 The Manufacture of Acrylic Polymers, CM-107, Rohm and Haas Co., Philadelphia, Pa.
- 96 The Manufacture of Ethyl Acrylate–Acrylic Acid Copolymers, TMM–48, Rohm and Haas Co., Philadelphia, Pa.
- 97 Bulk Storage and Handling of Acryloid Coating Resins, C-186, Rohm and Haas Co., Philadelphia, Pa.
- 98 P. A. Lovell and M. S. El-Aasser, Emulsion Polymerization and Emulsion Polymers, John Wiley and Sons, Inc., New York, 1997.
- 99 S.C. Thickett and R.G. Gilbert, Emulsion polymerization: State of the Art in Kinetics and Mechanisms. Polymer 48 (24), 6965-6991 (2007).
- 100U.S. Pat. 5,521,266 (May 28, 1996), W. Lau (to Rohm and Haas Co.).
- 101 B. B. Kine and G. H. Redlich, in D. T. Wasan, ed., Surfactants in Chemical/Process Engineering, Marcel Dekker, Inc., New York, 1988, p. 163.
- 102 A. E. Alexander, J. Oil Colour Chem. Assoc. 42, 12 (1962).
- 103 C. E. McCoy Jr., Off. Dig. Fed. Soc. Paint Technol. 35, 327 (1963).
- 104 A. F. Sirianni and R. D. Coleman, Can. J. Chem. 42, 682 (1964).
- 105 G. L. Brown, Off. Dig. Fed. Soc. Paint Technol. 28, 456 (1956).
- 106Brit. Pat. 940,366 (Oct. 30, 1963), P. R. van Ess (to Shell Oil).
- 107U.S. Pat. 3,080,333 (Mar. 5, 1963), R. J. Kray and C. A. DeFazio (to Celenese).
- 108 A. R. M. Azad, R. M. Fitch, and J. Ugelstad, Colloidal Dispersions Micellar Behavior (ACS Symp. Ser. No. 9), American Chemical Society, Washington, D.C., 1980.
- 109 H. Fikentscher, H. Gerrens, and H. Schuller, Angew. Chem. 72, 856 (1960).
- 110 A. S. Sarac, Prog. Polym. Sci. 24, 1149 (1999).
- 111U.S. Pat. 3,458,466 (July 29, 1969), W. J. Lee (to The Dow Chemical Company).
- 112U.S. Pat. 3,344,100 (Sept. 26, 1967), F. J. Donat and co-workers (to B. F. Goodrich Co.).
- 113 H. Warson and C.A. Finch Applications of Synthetic Resin Latices, John Wiley & Sons Ltd., UK, 2001.
- 114
G. Odian
Principles of Polymerization, 4th Edition,
John Wiley & Sons, Inc.,
New York,
2004.
10.1002/047147875X Google Scholar
- 115 G. S. Whitby and co-workers, J. Polym. Sci. 16, 549 (1955).
- 116 B. N. Rutovshii and co-workers, J. Appl. Chem. USSR 26, 397 (1953).
- 117 H. Warson, Polym. Paint Colour J. 178, 625 (1988).
- 118 H. Warson, Polym. Paint Colour J. 178, 865 (1988).
- 119 L. J. Hughes and G. L. Brown, J. Appl. Polym. Sci. 7, 59 (1963).
- 120 B. N. Kishore and co-workers, J. Polym. Sci., Polym. Chem. Ed. 24, 2209 (1986).
- 121 G. Graczyk and V. Hornof, J. Macromol. Sci., Chem. 12, 1633 (1988).
- 122 O. Y. Mansour and A. B. Moustafa, J. Polym. Sci., Polym. Chem. Ed. 13, 2795 (1975).
- 123 T. Nagabhushanam and M. Santoppa, J. Polym. Sci., Polym. Chem. Ed. 14, 507 (1976).
- 124 L. Zhi-Chong and co-workers, J. Macromol. Sci., Chem. 12, 1487 (1988).
- 125 C. E. Brockway and K. B. Moser, J. Polym. Sci., Part A-1 1, 1025 (1963).
- 126 G. Smets, A. Poot, and G. L. Dunean, J. Polym. Sci. 54, 65 (1961).
- 127 C. H. Bamford and E. F. T. White, Trans. Faraday Soc. 52, 719 (1956).
- 128 J. A. Hicks and H. W. Melville, Nature (London) 171, 300 (1953).
- 129 I. Sahata and D. A. I. Goring, J. Appl. Polym. Sci., 20, 573 (1976).
- 130 R. K. Graham, M. J. Gluchman, and M. J. Kampf, J. Polym. Sci. 38, 417 (1959).
- 131 D. J. Angier, E. D. Farlie, and W. F. Watson, Trans. Inst. Rubber Ind. 34, 8 (1958).
- 132 W. J. Burlant and A. S. Hoffman, Block and Graft Polymers, Reinhold Publishing Corp., New York, 1960.
- 133 A.E. Muftuoglu, M. Tasdelen, Y. Atilla, M. Yusuf, K. Mishra Plastics 73, 307-344 (2009).
- 134 M. Szwarc, J. Polym. Sci., Part A: Polym. Chem. 36, ix, (1998).
- 135 T. E. Patten and K. Matyjaszewski, Adv. Mater. 10, 901 (1998).
- 136 M. K. Georges and co-workers, Macromolecules 26, 2987 (1993).
- 137 G. Moad, J. Chem. 59 (10), 661-66, (2006).
- 138 C. J. Hawker and co-workers, Macromolecules 31, 213 (1998).
- 139 J. S. Wang and K. Matyjaszewski, Macromolecules 28, 7901 (1995).
- 140 T. E. Patten and co-workers, Science 272, 866 (1996).
- 141 S. Coca and co-workers, J. Polym. Sci., Part A: Polym. Chem. 36, 1417 (1998).
- 142 K. Matyjaszewski, S. Coca, and C. B. Jasiaczek, Macromol. Chem. Phys. 198, 4001 (1997).
- 143 S. Coca and K. Matyjaszewski, Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.) 38, 691 (1997).
- 144 D. McGinniss, Ultraviolet Light Induced Reactions in Polymers, ACS Symp. Ser. No. 25, American Chemical Society, Washington, D.C., 1976.
- 145 J. W. Vanderhoff, J. Polym. Sci. 38 (1959).
- 146 Y. Irmouli, B. George, and A. Merlin, J. Thermal Analysis and Calorimetry 96 (3), 911-916 (2009).
- 147U.S. Pat. 3,418,295 (Dec. 24, 1968), A. C. Schwenthaler (to E. I. du Pont de Nemours & Co., Inc.).
- 148 V. D. McGinnis, SME Technical Paper (Ser.) FC 76-486, 1976.
- 149 J. V. Koleche, Photochemistry of Cycloaliphatic Epoxides and Epoxy Acrylates, Vol. I, ASTM International, 1989.
- 150 B.E. Hulme and J.J. Marron, Paint & Resin 54 (1), 31-41, 1984.
- 151 T. A. Du Plessis and G. De Hollain, J. Oil Colour Chem. Assoc. 62, 239 (1979).
- 152 M. L. Miller and C. E. Rauhut, J. Polym. Sci. 38, 63 (1959).
- 153 B. Garret, J. Am. Chem. Soc. 81, 1007 (1959).
- 154
A. Kawasahi and co-workers,
Makromol. Chem.
49,
76
(1961).
10.1002/macp.1961.020490108 Google Scholar
- 155 G. Smets and W. Van Hurnbeeck, J. Polym. Sci., Part A-1 1, 1227 (1963).
- 156 W. E. Goode, R. P. Fellman, and F. H. Owens, in C. G. Overberger, ed., Macromolecular Synthesis, Vol. 1, John Wiley & Sons, Inc., New York, 1963, p. 25.
- 157
J. Furukawa,
T. Tsuruta, and
T. Makimoto,
Makromol. Chem.
42,
162
(1960).
10.1002/macp.1960.020420116 Google Scholar
- 158
T. Makmoto,
T. Tsuruta, and
J. Furukawa,
Makromol. Chem.
50,
116
(1961).
10.1002/macp.1961.020500108 Google Scholar
- 159 Y. Heimei and co-workers, in N. A. J. Platzer, ed., Appl. Polym. Symp., Vol. 26, 1975, p. 39.
- 160 D. E. Glusker and co-workers, J. Polym. Sci. 49, 315 (1961).
- 161 D. J. Cram and K. R. Kopecky, J. Am. Chem. Soc. 81, 2748 (1959).
- 162 H. Yuki and co-workers, in O. Vogl and J. Furukawan, eds., Ionic Polymerization, Marcel Dekker, Inc., New York, 1976.
- 163 M. T. Reetz, Angew. Chem., Int. Ed. Engl. 27, 994 (1988).
- 164 V. V. Korshak and co-workers, Makromol. Chem. Suppl. 6, 55 (1984).
- 165 C. P. Bosmyak, I. W. Parsons, and J. N. Hay, Polymer 21, 1488 (1980).
- 166 F. L. Keohan and co-workers, J. Polym. Sci., Polym. Chem. Ed. 22, 679 (1984).
- 167 Y. D. Lee and H. B. Tsai, Makromol. Chem. 190, 1413 (1989).
- 168 E. A. Collines and co-workers, J. Coat. Technol. 47, 35 (1975).
- 169 E. B. Bradford and J. W. Vanderhoff, J. Polym. Sci. Part C, 1 41 (1963).
- 170
T. F. Protxman and
G. L. Brown,
J. Appl. Polym. Sci.
81
(1960).
10.1002/app.1960.070041012 Google Scholar
- 171 P. W. Allen, Technique of Polymers Characterization, Butterworths, London, 1959.
- 172 Dilute Solution Properties of Acrylic and Methacrylic Polymers, SP-160, Rohm and Haas Co., Philadelphia, Pa.
- 173 M. Harmon and J. King, U.S. NTIS AD Rept. AD-A0I7443, p. 142, 1974.
- 174 R. E. Harren, A. Mercurio, and J. D. Scott, Aust. Oil Colour Chem. Assoc. Proc. News 17 (Oct. 1977).
- 175 W.H. Brendley and R.D. Bakule, Chemistry and Technology of Acrylic Resins for Coatings. ACS Symposium Series 285 (Appl. Polym. Sci. (2nd Ed.)), 1031-52 (1985).
- 176 C.A. Hawkins, A.C. Sheppard, and T.G. Wood, Progress in Organic Coatings 32 (1-4), 253-261 (1997).
- 177 R. P. Hopkins, E. W. Lewandowski, and T. E. Purcell, J. Paint Technol. 44, 85 (1972).
- 178 T. E. Purcell, Am. Paint J. (June 1972).
- 179 Technical Practices Committee, Materials Performance, Vol. 15, National Assoc. of Corrosion Engineers, Houston, Tex., 1976, pp. 4, 13.
- 180 K. E. Buffington, Maint. Eng. (Mar. 1976).
- 181 I. K. Schahidi, J. C. Trebellas, and J. A. Vona, Paint Varn. Prod. 64, 39 (1974).
- 182 C. B. Rybyn and co-workers, J. Paint Technol. 46, 60 (1974).
- 183 Multifunctional Acrylates in Radiation Curing, Celanese Co., New York.
- 184 C. H. Carder, Paint Varn. Prod. 64, 19 (1974).
- 185 Materials for Photocurable Coatings and Inks, Union Carbide Corp., New York.
- 186 R. A. Hickner and L. M. Ward, Paint Varn. Prod. 64, 27 (1974).
- 187 F. Wingler and co-workers, Farbe Lack 78, 1063 (1972).
- 188 R. Muller, Farbe Lack 78, 1070 (1972).
- 189 J. K. Rankin, J. Oil Colour Chem. Assoc. 56, 112 (1973).
- 190 F. A. Kyrlova, Lakokras. Mater. Ikh Primen. 3, 20 (1969).
- 191 J. B. Zicherman, Am. Paint J. 56 (46), ( 23–28 1972).
- 192U.S. Pat. 1,535,228 (Aug. 16, 1968), K. Shibayama (to Eiki Jidaito).
- 193 F. Beck and co-workers, Farbe Lack 73, 298 (1967).
- 194 A. Mercurio and S. N. Lewis, J. Paint Technol. 47, 37 (1975).
- 195 W. H. Brendley Jr. and E. C. Carl, Paint Varn. Prod. 63, 23 (1973).
- 196 M. R. Yunaska and J. E. Gallagher, Resin Review, Vol. 19, Rohm and Haas Co., Philadelphia, Pa., 1969, pp. 1–3.
- 197 G. Allyn, Materials and Methods, Reinhold Publishing Co., New York, 1956.
- 198 Protecting the Surfaces of Copper and Copper-Base Alloys, International Copper Research Association, New York.
- 199 R. R. Kuhn, N. Roman, and J. D. Whiteman, Mod. Paint Coatings 71, 50 (1981).
- 200
J. C. Thiabault,
P. R. Sperry, and
E. J. Schaller, in
J. E. Glass, ed.,
Water-Soluble Polymers,
American Chemical Society,
Washington, D.C.,
1986,
p. 375.
10.1021/ba-1986-0213.ch020 Google Scholar
- 201 A. J. Reuvers, Prog. Org. Coatings 35, 171 (1999).
- 202 T. L. Maver, J. Coat. Technol. 64, 45 (1992).
- 203 T. Murakami, R. H. Fernando, and J. E. Glass, Surf. Coat. Int. 76, 8 (1993).
- 204
N. Sutterlin,
Makromol. Chem. Suppl.
10/11,
403
(1985).
10.1002/macp.1985.020101985128 Google Scholar
- 205 V. J. Moser, Resin Review, Vol. 14, Rohm and Haas Co., Philadelphia, Pa., 1964, p. 25.
- 206 D. I. Lunde, Nonwoven Fabrics Forum, Clemson University, June 15–17, 1982.
- 207U.S. Pat. 3,157,562 (Nov. 17, 1964), B. B. Kine, V. J. Moser, and H. A. Alps (to Rohm and Haas Co.).
- 208U.S. Pat. 3,101,292 (Aug. 20, 1963), B. B. Kine and N. A. Matlin (to Rohm and Haas Co.).
- 209 J. R. Lawrence, Resin Review, Vol. 6, Rohm and Haas Co., Philadelphia, Pa., 1956, p. 12.
- 210U.S. Pat. 2,931,749 (Apr. 5, 1960), B. B. Kine and N. A. Matlin (to Rohm and Haas Co.).
- 211 G. C. Kantner, Text. World 132, 89 (1982).
- 212 G. C. Kantner, Am. Text. 12, 30 (Feb. 1983).
- 213 L. Thompson and H. Mayfield, AATCC National Technical Conference, 1974, p. 258.
- 214 F. X. Chancler and J. G. Brodnyan, Resin Review, Vol. 23, Rohm and Haas Co., Philadelphia, Pa., 1973, p. 3.
- 215 V. J. Moser and D. G. Strong, Am. Dyest. Rep. 55, 52 (1966).
- 216U.S. Pat. 2,883,304 (Apr. 21, 1959), B. B. Kine and A. C. Nuessle (to Rohm and Haas Co.).
- 217Brit. Pat. 1,011,041 (1962), K. Craemer (to Badische Anilin).
- 218 K. F. Foley and S. G. Chu, Adhes. Age 24 (Sept. 1986).
- 219 D. Satas, Adhes. Age 28 (Aug. 1988).
- 220 J. J. Latimer, Pulp Pap. Can. 82, 83 (1981).
- 221 J. E. Young and J. J. Latimer, South. Pulp Pap. J. 45, 5 (1982).
- 222 P. J. McLaughlin, Tappi 42, 994 (1959).
- 223 L. Mlynar and R. W. McNamec Jr., Tappi 55, 359 (1972).
- 224 F. L. Schucker, Resin Review, Vol. 7, Rohm and Haas Co., Philadelphia, Pa., 1957, p. 20.
- 225 H. C. Adams, T. J. Drennen, and L. E. Kelley, Tappi 48, 486 (1965).
- 226 H. Ito, H.D. Truong, M. Okazaki, D.C. Miller, N. Fender, P.J. Brock, G.M. Wallraff, C.E. Larson, and R.D. Allen, J. Photopolymer Sci. Technol. 15 (4), 591-602. (2002).
- 227 J.W. Thackeray and R.A. Nassar, Novel Polymers and Photoresist Compositions, Rohm and Haas Electronic Materials LLC, USA. U.S. Pat. Appl. Publ. (2008).
- 228 A. Uhl, J. Bendig, U.A. Jagdhold, and J.J. Bauer, DUV and e-Beam Chemistry of High-sensitivity Positive PMMA-based resist. Proceedings of SPIE-The International Society for Optical Engineering 3678(Pt. 2, Advances in Resist Technology and Processing XVI), 1381-1387, (1999).
- 229 W. C. Prentiss, J. Am. Leather Chem. Assoc. 71, 54 (1976).
- 230 P. E. Wright and H. C. Young, Resin Review, Vol. 24, Rohm and Haas Co., Philadelphia, Pa., 1974, p. 17.
- 231 P. H. Dougherty and H. T. Freund, Resin Review, Vol. 17, Rohm and Haas Co., Philadelphia, Pa., 1967, p. 3.
- 232 L. S. Frankel, D. A. Perry, and J. J. Lavelle, Resin Review, Vol. 32, Rohm and Haas Co., Philadelphia, Pa., 1982, p. 1.
- 233 J. T. Lutz Jr., in Ref. 197, p. 18.
- 234 M. Cohen, Proc. Fl. State Hortic. Soc. 72, 56 (1959).
- 235 Resin Review, Vol. 16, Rohm and Haas Co., Philadelphia, Pa., 1966, p. 12.
- 236 T. M. Vial, Rubber Chem. Technol. 44, 344 (1971).
- 237 P. Fram, in N. M. Bikales, ed., Encyclopedia of Polymer Science and Technology, Vol. 1, Interscience Publishers, New York, 1964, pp. 226–246.
- 238 D. L. Schultz, Rubber World 182, 51 (May 1980).
