Skip to main content
Log in

Vinyl monomers derived from fats and oils

  • Technical
  • Symposium on Chemical Modification of Fats and Oils Conducted by The American Oil Chemists' Society at Its 53rd Annual Meeting May 7, 1963
  • Published:
Journal of the American Oil Chemists Society

Abstract

Preparation, properties, and uses of monomers containing saturated or unsaturated C12–18 fatty radicals derived from fats and oils and capable of polymerization or copolymerization by vinyltype mechanisms are reviewed. Principal monomers discussed are vinyl esters and ethers, acrylic esters, allylic esters and ethers, and α-olefins.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Adelman, R. L., J. Org. Chem.14, 1057–1077 (1949).

    Article  CAS  Google Scholar 

  2. Adelson, D. E., and H. F. Gray, Jr. (Shell Development Co.), U. S. 2,555,775 (1951).

  3. Adicoff, A., and A. Buselli, J. Polymer Sci,21, 340–343 (1956).

    Article  CAS  Google Scholar 

  4. Agius, P. J. V. J., and P. R. Morris. (Esso Research and Engineering Co.), Brit. 804,222 (1958).

    Google Scholar 

  5. Agius, P. J. V. J., P. R. Morris, T. A. Garbett, and J. D. Bryan. (Ibid.) Brit. 798,542 (1958).

    Google Scholar 

  6. Alfrey, T., Jr. (L. A. Dreyfus Co.), U. S. 2,740,772 (1956).

  7. Anon., Chem. Eng. News36 (31), 23–24 (Aug. 4. 1958).

  8. Asahara, T., J. Chem. soc. Japan Ind. Chem. Sect.52, 52–53 (1949).

    CAS  Google Scholar 

  9. Asahara, T., and K. Mitsuhashi, Yukagaku6, 331–335 (1957).

    CAS  Google Scholar 

  10. Asahara, T., and K. Mitsuhashi,Ibid.,,6, 339–350 (1959).

    Google Scholar 

  11. Asahara, T., and M. Tomita, Yushi Kagaku Kyokaishi1, 76–79 (1952).

    CAS  Google Scholar 

  12. Asinger, F., Ber.75B, 660–663 (1942).

    CAS  Google Scholar 

  13. Asinger, F.,Ibid., Ber., 1247–1259.

  14. Asinger, F., and H. Eckoldt,Ibid. 76B, 585–592 (1943).

    CAS  Google Scholar 

  15. Ballantine, D. S., P. Colombo, A. Glines, B. Manowitz, and D. J. Metz, U. S. Atomic Energy Commission BNL-414 (1956).

  16. Barnum, E. R., and L. E. Lorensen. (Shell Development Co.), U. S. 2,781,319 (1957).

  17. Barnum, E. R., L. E. Lorensen, and J. Zachar. (Ibid.), U. S. 2,839,512 (1958).

  18. Bartl, H., and H. Gensel (Farbenfabriken Bayer, A.-G.), U. S., 2,917,478 (1959).

  19. Bartlett, J. H. (Standard Oil Development Co.), U. S. 2,656,318 (1953).

  20. Bartlett, J. H., (Ibid.) (Standard Oil Development Co.), U. S. 2,694,685 (1954).

  21. Bauer, L. N., and H. T. Neher. (Rohm and Haas Co.), U. S. 2,692,256 (1954); Brit. 715,913 (1954).

  22. Bauer, L. N., H. T. Neher, and W. L. Van Horne. (Ibid.), (Rohm and Haas Co.), (a) U. S. 2,731,448 (1956); (b) 2,600,420 (1952); (c) 2,600,421 (1952); (d) 2,600,448 (1952); (e) 2,600,446 (1952); (f) 2,600,383 (1952); (g) 2,600,447 (1952).

  23. Bondi, A. A., and L. B. Scott. (Shell Development Co.), U. S. 2,800,453 (1957).

  24. Bosen, R., and W. J. Sparks. (Standard Oil Development Co.), U. S. 2,468,516 (1949).

  25. Brekke, O. L., and L. D. Kirk, JAOCS37, 568–570 (1960).

    Article  CAS  Google Scholar 

  26. Bryant, H. W., and W.R. Cornthwaite. (DuPont Co.), U. S. 2,668,809 (1954).

  27. Burlant, W. J., and A. Adicoff, J. Polymer Sci.27, 269–274 (1958).

    Article  CAS  Google Scholar 

  28. Butler, J. M. (Monsanto Chemical Co.), U. S. 2,541,686 (1951).

  29. Butler, J. M. (Ibid.), (Monsanto Chemical Co.), U. S. 2,541,687 (1951).

  30. Butler, J. M. (Ibid.), (Monsanto Chemical Co.), U. S. 2,544,375 (1951).

  31. Calderon, R., H. P. Dupuy, E. R. McCall, R. T. O'Connor, and L. A. Goldblatt, JAOCS37, 132–136 (1960).

    CAS  Google Scholar 

  32. Catlin, W. E. (Du Pont Co), U. S. 2,613,184 (1952).

  33. Catlin, W. E., and B. W. Howk. (Ibid.), (DuPont Co.), U. S. 2,728,751 (1955).

  34. C-D-I-C Production Clubs, Off. Dig. Federation Socs. Paint Technol.27, 783–793 (1955).

    Google Scholar 

  35. CIBA, Swiss 265,396; 265,398-265,401 (1950).

  36. (a) Clarke, J. T., and (b) R. S. Corley, Articles in “Monomers,” edited by E. R. Blout, W. P. Hohenstein, and H. Mark, Interscience Publishers, New York, 1949-1951.

    Google Scholar 

  37. Coenne, M. (Farbenfabriken Bayer A.-G.), Ger. 1,001,665 (1957).

  38. Collins, W. C., (Johnson and Johnson, Inc.), U. S. 2,913,355 (1959).

  39. Cook, J. F. (Union Oil Co., Calif.), U. S. 2,858,272 (1958).

  40. Copenhaver, J. W., and M. H. Bigelow, “Acetylene and Carbon Monoxide Chemistry,” Reinhold Publishing Corp., New York, 1949, pp. 32–55.

    Google Scholar 

  41. Cowan, J. C., and H. M. Teeter, (U.S.D.A.), U. S. 2,901,469 (1959).

  42. Cox, R. P., R. D. Jerabek, and J.C. Konen, JAOCS30, 360–365 (1953).

    Article  CAS  Google Scholar 

  43. (a) Craig, L. E., R. F. Kleinschmidt, E. S. Miller, J. M. Wilkinson, R. W. Davis, C. F. Montross, and W. S. Port, Int. Eng. Chem.47, 1702–1706 (1955); (b) C. S. Redfleild, W. S. Port, and D. Swern,Ibid.Ind. Eng. Chem., 1707–1710.

    Article  Google Scholar 

  44. Dainton, F. S., K. J. Ivin, and D. R. Sherd, Trans. Faraday Soc.52, 414–425 (1956); Disc. Faraday Soc. No. 14, 199–207 (1953).

    Article  CAS  Google Scholar 

  45. Dannenberg, H. (Shell Development Co.), U. S. 2,884,339 (1959).

  46. Davies, G. G., I. M. Heilbron, and W. M. Owens, J. Chem. Soc. 2542 (1930).

  47. DeJarlais, W. J., J. L. O'Donnell, and H. M. Teeter, JAOCS38, 241–243 (1961).

    Article  CAS  Google Scholar 

  48. DeJarlais, W. J., and H. M. Teeter,Ibid. 37, 556–558 (1960).

    Article  CAS  Google Scholar 

  49. Deschamps, J., M. Paty, and P. Pineau, Compt. red.238, 2006–2008 (1954).

    CAS  Google Scholar 

  50. Dreisbach, R. R., Physical Properties of Chemical Compounds-II. Am. Chem. Soc., Advances in Chemistry Serries, No. 22, 1959.

  51. Dufek, E. J., R. A. Awl, L. E. Gast, J. C. Cowan, and H. M. Teeter, JAOCS37, 37–40 (1960).

    Article  CAS  Google Scholar 

  52. Dufek, E. J., and H. M. Teeter,Ibid. JAOCS, In Press.

  53. Dunphy, J. F., and C. S. Marvel, J. Polymer Sci.46, 542–543 (1960).

    Article  CAS  Google Scholar 

  54. Dunphy, J. F., and C. S. Marvel,Ibid. 47, 1–8 (1960).

    Article  CAS  Google Scholar 

  55. DuPont Co., Brit. 585,396 (1947).

  56. Dupont, G., R. Dulon, and Y. Cretien-Bessiere, Compt. rend.246, 128–130 (1948).

    Google Scholar 

  57. Dyer, E., and W. C. Meisenhelder, J.Am. Chem. Soc.73, 1134–1137 (1951).

    Article  Google Scholar 

  58. Dyer, E., and G. A. Weisgerber. (Armstrong Cork Co.), U. S. 2,698,840 (1955).

  59. Eckey, E. W., R. O. Alderson, and E. W. Woestman, JAOCS32, 185–191 (1955).

    CAS  Google Scholar 

  60. Eley, D. D., J. Oil & Colour Chemists' Assoc.40, 810–813 (1957).

    CAS  Google Scholar 

  61. Esso Research and Engineering Co., Brit. 825,885 (1959).

    Google Scholar 

  62. Ibid., Esso Research and Egineerin Co., Brit. 830,727 (1960).

  63. Ibid., Esso Research and Egineerin Co., Brit. 834,516 (1960).

  64. Ibid., Esso Research and Egineerin Co., Brit. 838,235 (1960).

  65. Ibid., Esso Research and Egineerin Co., Brit. Ger. 1,032,460 (1958).

  66. Esso Std. Societe Anon. francaise, Brit. 810,647 (1959).

  67. Farbenfabriken Baver A.-G., Brit. 771.336 (1957).

  68. Ibid., Farbenfabriken Baver A.-G., Brit. 771,746 (1957).

  69. Ibid., Farbenfabriken Baver A.-G., Brit. 776,805 (1957).

  70. Ibid., 818,715 (1959).

  71. Fee, J. G., W. S. Port, and L. P. Witnauer, J. Polymer Sci.33, 95–100 (1958).

    Article  CAS  Google Scholar 

  72. Feldon, M., R. R. Hammel, and R. W. Laundine, Ind. Eng. Chem.46, 2248–2260 (1954).

    Article  CAS  Google Scholar 

  73. Frostick, F. C., Jr., B. Phillips, and P. S. Starcher, J. Am. Chem. Soc.81, 3350–3356 (1959).

    Article  CAS  Google Scholar 

  74. Garber, J. D., and W. C. Hollyday, Jr., (Standard Oil Development Co.). U. S. 2,581.092 (1952).

  75. Garber, J. D. C. Hollyday, Jr., and B. M. Vanderbilt. (Esso Research and Engineering Co.), U. S. 2.746.925 (1956).

  76. Gast, L. E., C. B. Coleman, and H. M. Teeter, J. Org. Chem.24, 160–165 (1959).

    Article  CAS  Google Scholar 

  77. Gast, L. E., W. J. Schneider, J. L. O'Donnell, J. C. Cowan, and H. M. Teeter, JAOCS35, 347–350 (1958).

    CAS  Google Scholar 

  78. Gast, L. E., W. J. Schneider, J. L. O'Donnell, and H. M. Teeter,Ibid. 37, 78–80 (1960).

    CAS  Google Scholar 

  79. Gast, L. E., W. J. Schneider, and H. M. Teeter,Ibid. 34, 307–310 (1957

    CAS  Google Scholar 

  80. Gast, L. E., W. J. Schneider, H.M. Teeter, G. E. McManis, and J. C. Cowan. Presented at AOCS meeting, St. Louis, Mo., 1961.

  81. Gast, L. E., R. J. Stenberg W. J. Schneider, and H. M. Teeter, Off. Dig. Federation Socs. Paint Technol.32, 1091–1101 (1960).

    Google Scholar 

  82. Gaylord, N. G., J. Polymer Sci.22, 71–78 (1956).

    Article  CAS  Google Scholar 

  83. Giammaria, J. J. (Socony-Vacuum Oil Co., Inc.). (a) U. S. 2,616,852 (1952); (b) U. S. 2,698,297 (1954): (c) (Socony Mobil Oil Co.), Ger. 945,282 (1956).

  84. Gleason, H. H. (Standard Oil Development Co.), U. S. 2,380,304 (1945).

  85. Geenberg, S. A., and T. Alfrey, J. Am. Chem. Soc.76, 6280–6285 (1954). See also H. S. Kaufman, A. Sacher, T. Alfrey, and I. Fankuchen,Ibid. J. Am. Chem. Soc.70, 3147 (1948).

    Article  Google Scholar 

  86. Hanford, W. E., and D. L. Fuller, Ind. Eng. Chem.40, 1171–1177 (1948).

    Article  CAS  Google Scholar 

  87. Harrison, S. A., and W. E. Tolberg, JAOCS30, 114–117 (1953).

    Article  Google Scholar 

  88. Harrison, S. A., and D. N. Wheeler, J. Am. Chem. Soc.73, 839–842 (1951).

    Article  CAS  Google Scholar 

  89. Hercules Powder Co., Ger. 1,033,413 (1958).

  90. Hewett, W. A., R. C. Jones, and L. E. Lorensen. (Shell Oil Co.), U. S. 2,895,915 (1959).

  91. Honig, C. W., and F. Reichert. (Dynamit A.-G. vorm. Alfred Nobel and Co.), Ger. 1,024,238 (1958).

  92. Huber, W. F., and E. S. Lutton, J. Am. Chem. Soc.,79, 3919–3920 (1957).

    Article  CAS  Google Scholar 

  93. Hunig, S., and M. Kiessel, Chem. Ber.91, 380–392 (1958).

    Article  CAS  Google Scholar 

  94. Huttenlocher, R., and E. Brudi. (Chemische Fabrik Duren G.m. b.H.), Ger. 1,020,011 (1958).

  95. Hwa, J. C. H., and W. H. Watanabe. (Rohm and Haas Co.), U. S. 2,847,478 (1958).

  96. I. G. Farbenindustrie A.-G., Brit. 279,674 (1932).

  97. Ishikawa, S., E. Kuroda, and K. Ishino, Bull. Inst. Phys. Chem. Research (Tokyo) Chem. Ed.23, 373–381 (1944).

    CAS  Google Scholar 

  98. Jones, J. L. (Libbey-Owens-Ford Glass Co.), U. S. 2,533,376 (1950).

  99. Jordan, E. F., Jr., K. M. Doughty, and W. S. Port, J. Appl. Polymer Sci.4, 203–206 (1960).

    Article  CAS  Google Scholar 

  100. Jordan, E. F., Jr., W. E. Palm, and W. S. Port, JAOCS38, 231–233 (1961).

    Article  CAS  Google Scholar 

  101. (a) Jordan, E. F., Jr., W. E. Palm, D. Swern, L. P. Witnauer, and W. S. Port, J. Polymer Sci.32, 33–46 (1958); (b) E. F. Jordan, Jr., and W. S. Port,Ibid. J. Polymer. Sci. 47–56.

    Article  CAS  Google Scholar 

  102. Jordan, E. F., Jr., W. E. Palm, L. P. Witnauer, and W. S. Port, Ind. Eng. Chem.49, 1695–1698 (1957).

    Article  CAS  Google Scholar 

  103. Jordan, E. F., Jr., and W. S. Port. (U.S.D.A.), U. S. 2,843,574 (1958).

  104. Kimura, T., and K. Yoshida, Kagaku to Kogyo (Osaka)32, 223–227 (1957).

    Google Scholar 

  105. Klemka, A. J., and C. O. Pike. (Norton Co.), U. S. 2,862, 613 (1958).

  106. Koch, W. T. (Societe industrielle de la Cellulose), Belg. 567,211 (1958).

    Google Scholar 

  107. Komori, S., S. Miyamori, and C. Sakai, Kogyo Kagaku Zasshi59, 1134–1137 (1956). (See also S. Komori, Japan. 2869 (1958).

    CAS  Google Scholar 

  108. Komori, S., E. Shinsugi, T. Sasaki, and H. Shimaoka,Ibid. 1137–1142.

    Google Scholar 

  109. Kornblum, N., and H. N. Holmes, J. Am. Chem. Soc.64, 3045–3046 (1942).

    Article  CAS  Google Scholar 

  110. Korschak, V. V., M. F. Shostakovskii, A. A. Ivanova, and N. A. Gernshtein, Zhur. Priklad. Khim.30, 1368–1374 (1957).

    Google Scholar 

  111. Kraft, F., Ber.16, 3018–3024 (1883).

    Google Scholar 

  112. Kray, R. J., J. Polymer Sci.44, 264–265 (1960).

    Article  Google Scholar 

  113. Laible, R. C., Chem. Revs.58, 807–843 (1958).

    Article  CAS  Google Scholar 

  114. Lal, J., J. Polymer Sci.31, 179–181 (1958).

    Article  Google Scholar 

  115. Lamm, R. R. (Patent and Licensing Corp.), U. S., 2,849,410 (1958).

  116. Larsen, R. G., and K. E. Marple. (Shell Development Co.), U. S. 2,441,023 (1948). ing Corp., New York, 1954, pp. 1–5.

  117. Larsen, R. G., and K. E. Marple. (Ibid.), (Shell Development Co.), U. S. 2,541,590 (1951).

  118. LeBesnerais, D., F.A.T.I.P.E.C. 4th Congr. Lucerne1957, 259–264.

  119. Linsk, J., and C. S. Scanley. (Standard Oil, Indiana), U. S. 2,710,282 (1955).

  120. Lippincott, S. B., and L. A. Mikeska. (Standard Oil Development Co.), U. S. 2,542,542 (1951).

  121. Lippincott, S. B., and L. A. Mikeska. (Ibid.), (Standard Oil Development Co.), U. S. 2,615,845 (1952).

  122. Lippincott, S. B., and D. W. Young. (Ibid.) (Standard Oil Development Co.), U. S. 2,599,339 (1952).

  123. Lorensen, L. E., E. R. Barnum, and J. Zachar. (Shell Development Co.), U. S. 2,889,282 (1959).

  124. Lorensen, L. E., J. Zachar, and R. C. Jones. (Shell Oil Co.), U. S. 2,944,974 (1960).

  125. Lowe, W., W. T., Stewart, and F. A. Stuart. (California Research Corp.), U. S. 2,892,791 (1959).

  126. McCorkle, M. R. (Armour and Co.), U. S. 2,355,314 (1944).

  127. Marvel, C. S., and W. G. DePierri, J. Polymer Sci.27, 39–58 (1958).

    Article  CAS  Google Scholar 

  128. Marvel, C. S., and J. R. Rogers,Ibid. 49, 335–352 (1961).

    Article  CAS  Google Scholar 

  129. Masuno, M., T. Asahara, and K. Kanabu, J. Chem. Soc. Japan Ind. Chem. Sect.52, 50–51 (1949).

    CAS  Google Scholar 

  130. Mattil, K. F. (Swift and Co.), U. S. 2,610,915 (1952).

  131. Melamed, S. (Rohm and Haas Co.), U. S. 2,816,880 (1957); Brit. 786,927 (1957).

  132. Melamed, S. (Ibid.), (Rohm and Haas Co.), U. S. 2,845,408 (1958).

  133. Michaels, E. B. (Stamford Chemical Co.), U. S. 2,913,427 (1959).

  134. Min, S., and C. Chu, Hua Hsueh Hsueh Pao23, 262–265 (1957).

    CAS  Google Scholar 

  135. Moroff, H. (Rohm and Haas, G.m.b.H.), Ger. 1,002,281 (1957).

  136. Mustakas, G. C., M. C. Raether, and E. L. Griffith, Jr., JAOCS37, 68–72 (1960).

    CAS  Google Scholar 

  137. Mustakas, G. C., M. C. Raether, and E. L. Griffin, Jr.,Ibid., JAOCS 100–103.

  138. Natta, G., I. Bassi, and P. Carradini, Makromol. Chem.18/19, 455–462 (1956).

    Article  CAS  Google Scholar 

  139. Natta, G., F. Danusso, and G. Moraglio, Atti accad. nazl. Lincei. Rend. classe sci. fis., mat. e nat.24, 254–260 (1958).

    CAS  Google Scholar 

  140. Newey, H. A. (Shell Development Co.), U. S. 2,912,416 (1959).

  141. Nusslein, J., J. von Finck, and H. Stark. (I. G. Farbenindustrie A.-G.), U. S. 2,168,534 (1939).

  142. N.V. de Bataafse Petroleum Maatschappij, Dutch 91,489 (1959).

  143. Otsuka, S., Y. Matsumoto, and S. Murahashi, Nippon Kagaku Zasshi75, 798–801 (1954).

    CAS  Google Scholar 

  144. Overberger, C. G. (L. A. Dreyfus Co.), U. S. 2,802,812 (1957).

  145. Overberger, C. G., C. Frazier, J. Mandelman, and H. F. Smith, J. Am. Chem. Soc.75, 3326–3330 (1953).

    Article  CAS  Google Scholar 

  146. Paloheimo, O., Suomen Kemistilehti23, 71–77 (1950).

    CAS  Google Scholar 

  147. Paul, R., and S. Tchelitcheff, Bull. soc. chim. France 453–454 (1947).

  148. Phillips, B., and F. C. Frostick. (Union Carbide and Carbon Corp.), U. S. 2,779,771 (1957).

  149. Pollack, M. A. (E. F. Drew and Co.), U. S. 2,536,568 (1951).

  150. Popkin, A. H. (Standard Oil Development Co.), U. S. 2,604,453 (1952).

  151. Port, W. S., J. E. Hansen, E. F. Jordan, Jr., T. J. Diest, and D. Swern, J. Polymer Sci.7, 207–220 (1951).

    Article  CAS  Google Scholar 

  152. Port, W. S., E. F. Jordan, Jr., J. E. Hansen, and D. Swern,Ibid. 9, 493–502 (1952).

    Article  CAS  Google Scholar 

  153. Port, W. S., E. F. Jordan, Jr., W. E. Palm, L. P. Witnauer, J. E. Hansen, and D. Swern, Ind. Eng. Chem.47, 472–480 (1955).

    Article  CAS  Google Scholar 

  154. Port, W. S., E. F. Jordan, Jr., and D. Swern. (U.S.D.A.), U. S. 2,586,860 (1952).

  155. Port, W. S., F. A. Kincl, and D. Swern, Off. Dig. Federation Socs. Paint Technol.26, 408–412 (1954). See also D. Swern, and E. F. Jordan, Jr. (U.S.D.A.), U. S. 2,562,965 (1951).

    Google Scholar 

  156. Port, W. S., J. W. O'Brien, J. E. Hansen, and D. Swern, Ind. Eng. Chem.43, 2105–2107 (1951). See also W. S. Port, J. W. O'Brien, and D. Swern. (U.S.D.A.), U. S. 2,671,760 (1954).

    Article  CAS  Google Scholar 

  157. Port, W. S., and D. Swern. (U.S.D.A.), U. S. 2,876,895 (1959).

  158. Powers, P. O., Ind. Eng. Chem.38, 837–842 (1946). See also K. H. Weber and P. O. Powers. (Armstrong Cork Co.), U. S. 2,518,509 (1950).

    Article  CAS  Google Scholar 

  159. Pritchard, J. E. (Phillips Petroleum Co.), U. S. 2,769,802 (1956).

  160. Ramsey, J. R., and A. I. Gebhart. (Colgate-Palmotive-Peet Co.), U. S. 2,527,081 (1950).

  161. Rann, J. R., J. W. Gates, D. A. Smith, and C. C. Unruh. (Eastman Kodak Co.), U. S. 2,882,161 (1959).

  162. Reding, F. P., J. Polymer Sci.21, 547–549 (1956).

    Article  CAS  Google Scholar 

  163. Rehberg, C. E., and C. H. Fisher, Ind. Eng. Chem.40, 1429–1433 (1948).

    Article  CAS  Google Scholar 

  164. Rehberg, C. E., and C. H. Fisher, J. Am. Chem. Soc.66, 1203–1207 (1944).

    Article  CAS  Google Scholar 

  165. Reppe, W., Ann.601, 84–111 (1956).

    CAS  Google Scholar 

  166. Reppe, W. (I. G. Farbenindustrie A.-G.), Fr. 724,955 (1931); Ger. 584,840 (1933); U. S. 1,959,927 (1934).

  167. Reppe, W. (ibid.), (I. G. Farbenindustrie A.-G.), Ger. 588,352 (1933). See also U. S. 2,066,075 (1936).

  168. Reppe, W., and O. Hecht. (Ibid.), (I. G. Farbenindustrie A.-G.), U. S. 2,157,348 (1939); Brit. 481,389 (1938).

  169. Reppe, W., and O. Schlichting (Ibid.), (I. G. Farbenindustrie A-G.), U. S 2,104,001 (1937).

  170. Reppe, W., H. Ufer, and E. Kuhn. (Ibid.), (I. G. Farbenindustrie A.-G.), U. S. 2,125,649 (1938).

  171. Restaino, A. J., R. B. Mesrobian, H. Morawetz, D. S. Ballantine, G. J. Dienes, and D. J. Metz, J. Am. Chem. Soc.78, 2939–2943 (1956).

    Article  CAS  Google Scholar 

  172. Rheineck, A. E., JAOCS28, 456–459 (1951). See also G. L. Schertz. (Hercules Powder Co.), U. S. 2,601.561 (1952).

    Article  CAS  Google Scholar 

  173. Riddle, E. H., “Monomeric Acrylic Esters,” Reinhold Publish.

  174. Rohm and Haas Co., Brit. 736,397 (1955).

  175. Rohm and Haas, G.m.b.H., Ger. 961,884 (1957).

  176. Rosenberg, J., and H. L. Greenberg, Modern Plastics35 (4), 173–174 ff. (1957).

    CAS  Google Scholar 

  177. Sakurada, I., and G. Takahasi, Chem. High Polymers (Japan)11, 255–260 (1954).

    CAS  Google Scholar 

  178. Sakurada, I., and G. Takashashi,Ibid., Chem. High Polymers (Japan), 266–270.

  179. Sakurada, I., and G. Takahashi,Ibid. 12, 362–367 (1955).

    CAS  Google Scholar 

  180. Seger, F. M., H. G. Doherty, and A. N. Sachanen, Ind. Eng. Chem.42, 2446–2452 (1950).

    Article  CAS  Google Scholar 

  181. Schildknecht, C. E., “Vinyl and Related Polymers,” John Wiley and Sons, Inc., New York, 1952, pp. 593–634.

    Google Scholar 

  182. Schildknecht, C. E.,Ibid., “, p. 637.

    Google Scholar 

  183. Schildknecht, C. E., S. T. Gross, H. R. Davidson, J. M. Lambert, and H. O. Zoss, Ind. Eng. Chem.40, 2104–2115 (1948).

    Article  CAS  Google Scholar 

  184. Schildknecht, C. E., A. O. Zoss, and C. McKinley,Ibid. 39, 180–186 (1947).

    Article  CAS  Google Scholar 

  185. Schmidt, A. W., and V. Schoeller, Brenstoff Chem.23, 235–240, 247–252 (1952).

    Google Scholar 

  186. Schneider, W. J., L. E. Gast, E. H. Melvin, C. A. Glass, and H. M. Teeter, JAOCS34, 244–247 (1957).

    CAS  Google Scholar 

  187. Schneider, W. J., L. E. Gast, A. W. Schwab, and H. M. Teeter,Ibid., JAOCS, In Press.

  188. Schumann, C., and H. Ufer. (I. G. Farbenindustrie A.-G.), U. S. 2,020,703 (1936).

  189. Schwarz, R. F., (C-D-I-C Production Clubs) Am. Paint J.40, No. 3B, 24–27, 29–32 (1955).

    Google Scholar 

  190. Shell Research Ltd., Brit. 829,634 (1960).

  191. Shokal, E. C., and P. A. Devlin, (Shell Oil Co.), U. S.2,940,955 (1960).

  192. Silbert, L. S., Z. B. Jacob, W. E. Palm, L. P. Witnauer, W. S. Port, and D. Swern, J. Polymer Sci.21, 161–173 (1956).

    Article  CAS  Google Scholar 

  193. Sladkov, A. M., and G. S. Petrov, Zhur. Obshchei Khim.24, 450–454 (1954).

    CAS  Google Scholar 

  194. Somerville, I. C., and R. F. M. Fisher. (Rohm and Haas Co.), U. S. 2,824,816 (1958).

  195. Sopper, D. T. (DuPont Co.), U. S. 2,917,402 (1959).

  196. Stewart, W. T., F. A. Stuart, and W. Lowe. (California Research Corp.), U. S. 2,892,792 (1959). See also Ger. 1,015,564 (1957).

  197. Suida, H., and J. Haura, Reichsamt Wirtschaftsaufbau. Chem. Ber. Pruf. Nr. 15 (PB 52014) 383–402 (1942).

    CAS  Google Scholar 

  198. Swern, D., G. N. Billen, and H. B. Knight, J. Am. Chem. Soc.69, 2439–2442 (1947).

    Article  CAS  Google Scholar 

  199. Swern, D., and G. B. Dickel. (U.S.D.A.), U. S. 2,527,597 (1950).

  200. Swern, D., and E. F. Jordan, Jr., J. Am. Chem. Soc.70, 2334–2339 (1948).

    Article  CAS  Google Scholar 

  201. Swern, D., and E. F. Jordan, Jr., Org. Syn.30, 106–109 (1950).

    CAS  Google Scholar 

  202. Swern, D., and E. F. Jordan, Jr. (U.S.D.A.), U. S. 2,623,141 (1953).

  203. Swern, D., and W. S. Port, J. Am. Chem. Soc.74, 1738–1739 (1952).

    Article  CAS  Google Scholar 

  204. Swern, D., and W. S. Port. (U.S.D.A.), U. S. 2,756,222 (1956).

  205. Tamikado, T., and Y. Iwakura, J. Polymer Sci.36, 529 (1959).

    Article  CAS  Google Scholar 

  206. Teeter, H. M., L. C. Dorman, and L. Harris, JAOCS37, 552–555 (1960).

    Article  CAS  Google Scholar 

  207. Teeter, H. M., E. J. Dufek, C. B. Coleman, C. A., Glass, E. H. Melvin, aud J. C. Cowan,Ibid. 33, 399–404 (1956).

    Article  CAS  Google Scholar 

  208. Teeter, H. M., L. E. Gast, and J. C. Cowan, Ind. Eng. Chem.50, 1703–1704 (1958).

    Article  CAS  Google Scholar 

  209. Teeter, H. M., W. J. Schneider, and L. E. Gast. (U.S.D.A.), U. S. 2,889,309 (1959).

  210. Thompson, C. F., W. S. Port, and L. P. Witnauer, J. Am. Chem. Soc.81, 2552–2556 (1959).

    Article  CAS  Google Scholar 

  211. Toussaint, W. J., and L. G. MacDowell. (Carbide and Carbon Chemicals Corp), U. S. 2,299,862 (1942).

  212. Union Carbide Corp., Brit. 788,530 (1958).

  213. U. S. Rubber Co., Brit. 779,854 (1957); 805,119 (1958).

  214. Uzzan, A., Rev. franc. corps gras7, 135–145 (1960).

    CAS  Google Scholar 

  215. Van Horne, W. L. H. T. Neher, and L. V. Bauer. (Rohm and Haas Co.), U. S. 2,684,355 (1954).

  216. Voronkov, M. G., J. Gen. Chem. U.S.S.R.20, 2060–2063 (1950).

    CAS  Google Scholar 

  217. Voss, A., and H. Stark, (I. G. Farbenindustrie A.-G.), U. S. 2,160,375 (1939).

  218. Waldmann, H., and H. Schubert, Chem. Ber.84, 139–144 (1951).

    Article  CAS  Google Scholar 

  219. Walker, C. A., Ind. Eng. Chem.41, 2640–2644 (1949).

    Article  CAS  Google Scholar 

  220. Ward, H. J., E. G. Sanderson, and M. A. Maloney. (British Cellophane, Ltd.), Brit. 813,863 (1959).

  221. Watanabe, W. H., and L. E. Conlon, J. Am. chem. Soc.79, 2828–2833 (1957).

    Article  CAS  Google Scholar 

  222. Watanabe, W. H., and L. E. Conlon. (Rohm and Hass Co.), U. S. 2,760,990 (1956).

  223. Watanabe, W. H., and L. E. Conlon. (Ibid.), (Rohm and Haas Co.), U. S. 2,847,477 (1958).

  224. Watanabe, W. H., L. E. Conlon, and J. C. H. Hwa, J. Org. Chem.23, 1666–1668 (1958).

    Article  CAS  Google Scholar 

  225. Werner, J., F. A. Hessel, and D. B. Witwer. (General Aniline and Film Co.), U. S. 2,853,417 (1958).

  226. Werntz, J. H. (DuPont Co.), U. S. 2,497,705 (1950).

  227. Williams, P. L. (Adhesive Tapes, Ltd.), U. S. 2,829,073 (1958).

  228. Witnauer, L. P., N. Watkins, and W. S. Port, J. Polymer Sci.20, 213–214 (1956).

    CAS  Google Scholar 

  229. Young, D. W. (Standard Oil Development Co.), U. S. 2,534,095 (1950).

  230. Zafiriadis, Z., and P. Mastagli, Compt. rend.238, 821–822 (1954).

    CAS  Google Scholar 

  231. Zieger, K., Ger. 1,034,169 (1958).

  232. Ziegler, K., and H. G. Gellert, U. S. 2,695,327 (1954).

Download references

Author information

Authors and Affiliations

Authors

Additional information

A laboratory of the No. Utiliz. Res. & Dev. Div., ARS, U.S.D.A.

About this article

Cite this article

Teeter, H.M. Vinyl monomers derived from fats and oils. J Am Oil Chem Soc 40, 143–156 (1963). https://doi.org/10.1007/BF02640723

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02640723

Keywords

Navigation