Advertisement

Fluorine-containing polymers. I. Fluorinated vinyl polymers with functional groups, condensation polymers, and styrene polymers

  • William Postelnek
  • Lester E. Coleman
  • Alan M. Lovelace
Conference paper
Part of the Advances in Polymer Science book series (POLYMER, volume 1/1)

Keywords

Acrylic Acid Benzoyl Peroxide Vinyl Ether Vinyl Acetate Vinyl Ester 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Bibliography

  1. 1.
    Ahlbrecht, A. H., and D. W. Codding: Acrylates of difficultly esterified alcohols. J. Amer. chem. Soc. 75, 984 (1953).CrossRefGoogle Scholar
  2. 2.
    Anspon, H. D., and J. J. Baron jr.: Development of a rigid transparent plastic material suitable for aircraft glazing at elevated temperature. Wright Air Development Center Technical Report 57-24 (1957).Google Scholar
  3. 3.
    Bachman, G. B., and L. L. Lewis: Monomers and polymers. I. Fluorinated styrenes. J. Amer. chem. Soc. 69, 2022–2025 (1947).Google Scholar
  4. 4.
    Barr, J. T., K. E. Rapp, R. L. Pruett, C. T. Bahner, J. D. Gibson and R. H. Lafferty jr.: Reactions of polyfluoro olefins. III. Preparation of polyfluoro ethers. J. Amer. chem. Soc. 72, 4480–4482 (1950).CrossRefGoogle Scholar
  5. 5.
    Bittles jr., J. A.: Fluorinated alkyl acrylates and methacrylates. U. S. Patent 2,628,958 (1953).Google Scholar
  6. 6.
    Borders, A. M.: Synthetic rubbers from carbon-fluorine compounds. Wright Air Development Center Technical Report 52-197, Part I (1951).Google Scholar
  7. 7.
    -Synthetic rubbers from carbon-fluorine compounds. Wright Air Development Center Technical Report 52-197, Part II (1952).Google Scholar
  8. 8.
    Bovey, F. A.: Synthetic rubbers from carbon-fluorine compounds. Wright Air Development Center Technical Report 52-197, Part III (1953).Google Scholar
  9. 9.
    -Synthetic rubbers from carbon-fluorine compounds. Wright Air Development Center Technical Report 52-197, Part IV (1955).Google Scholar
  10. 10.
    -Synthetic rubbers from carbon-fluorine compounds. Wright Air Development Center Technical Report 52-197, Part V (1956).Google Scholar
  11. 11.
    -, J. F. Abere, G. B. Rathmann and C. L. Sandberg: Fluorine-containing polymers. III. Polymers and copolymers of 1,1-dihydroperfluoroalkyl acrylates. J. Polymer Sci. 15, 520–536 (1955).Google Scholar
  12. 12.
    --: Fluorine-containing polymers. IV. Polymers of acrylates of fluorinecontaining ether alcohols. J. Polymer Sci. 15, 537–543 (1955).Google Scholar
  13. 12A.
    Brooks, L. A.: The preparation of substituted styrenes. J. Amer. chem. Soc. 66, 1295–1297 (1944).CrossRefGoogle Scholar
  14. 13.
    -, and M. Nazzewski: Electrical insulation from dihalogenated polystyrene and copolymers. U. S. Patent 2,406,319 (1946).Google Scholar
  15. 14.
    Butler, G. B., R. Dunmire, G. W. Dykes and P. Tarrant: Preparation and polymerization of fluoroalkylmethylchlorosilanes. Abstracts 130th Meeting Amer. chem. Soc. 3 S (1956).Google Scholar
  16. 15.
    Buxton, M. W., M. Stacey and J. C. Tatlow: Studies upon α-trifluoromethylacrylic acid, α-trifluoromethylpropionic acid and some derived compounds. J. chem. Soc. 1954, 366–374.Google Scholar
  17. 16.
    Chaney, D. W.: Perfluorinated acrylonitriles. U. S. Patent 2, 439, 505, April 13, 1948.Google Scholar
  18. 17.
    Clark jr., R. T.: Elastomeric fluoroalkyl silicone copolymers. Wright Air Development Center Technical Report 54-213 (1954).Google Scholar
  19. 18.
    Codding, D. W., T. S. Reid, A. H. Ahlbrecht, G. H. Smith jr. and D. R. Husted: Fluorine-containing polymers. II. 1,1-dihydroperfluoroalkyl acrylates: preparation of monomers. J. Polymer Sci. 15, 515–519 (1955).Google Scholar
  20. 19.
    Cohen, S. G., H. T. Wolosinski and P. J. Scheuer: α,Β,Β-trifluorostyrene and α-chloro-Β,Β-difluorostyrene. J. Amer. chem. Soc. 71, 3439–3440 (1949).CrossRefGoogle Scholar
  21. 20.
    Coleman jr., L. E.: Unpublished data.Google Scholar
  22. 21.
    Coleman, L. E., and G. R. Eykamp: Polymerization of some α,α,Ω-trihydroperfluoroacrylates. Wright Air Development Center Technical Memorandum 57–56 (1957).Google Scholar
  23. 22.
    -, D. A. Rausch jr. and W. R. Griffin: Polymerization of some 1-alkyl-1-hydroperfluoroalkyl acrylates. Wright Air Development Technical Memorandum 57–57 (1957).Google Scholar
  24. 23.
    Coover, H. W., and J. B. Dickey: Polymerization of monomeric vinyl compounds. U. S. Patent 2,675,372 (1954).Google Scholar
  25. 24.
    Coover jr., H. W., J. E. Stanin and J. B. Dickey: Alkenyl trifluoroacetates. U. S. Patent 2,525,526 (1950).Google Scholar
  26. 25.
    Copenhaver, J. W.: Arctic rubber. The M. W. Kellogg Company. Report No. RL-54-353 (1954) and Report No. RL-55-401 (1955).Google Scholar
  27. 26.
    -Arctic rubber. The M. W. Kellogg Company. Report No. RL-55-434 (1955).Google Scholar
  28. 27.
    Corley, R. S., J. Lal and M. W. Kane: The properties of some fluorinated vinyl ethers. J. Amer. chem. Soc. 78, 3489–3493 (1956).Google Scholar
  29. 28.
    Crawford, J. W. C., R. H. Stanley and Imperial Chemical Industries Ltd.: Fluoroalkyl methacrylate esters and polymers. British Patent 580, 665 (1946).Google Scholar
  30. 29.
    -Fluorine-containing esters and their polymers. British Patent 616,849 (1949).Google Scholar
  31. 30.
    Dahlquist, C. A.: Synthetic rubbers from carbon-fluorine compounds. Wright Air Development Center Technical Report 52-197, Part VI (1955).Google Scholar
  32. 31.
    Darrall, R. A., F. Smith, M. Stacey and J. C. Tatlow: Organic fluorides. Part IX. The formation and resolution of α-hydroxy-α-trifluoromethylpropionic acid. J. chem. Soc. 1951, 2329–2332.Google Scholar
  33. 32.
    Dickey, J. B.: α-(fluoromethyl)acrylamides. U. S. Patent 2,541,465 (1951).Google Scholar
  34. 33.
    -α-(fluoromethyl)acrylonitrile. U. S. Patent 2,541,466 (1951).Google Scholar
  35. 34.
    -Fluoroacrylate ester polymers. U. S. Patent 2,472,811 (1949).Google Scholar
  36. 35.
    -Derivatives of fluoridated methacrylic acid. U. S. Patent 2,472,812 (1949).Google Scholar
  37. 36.
    -, and H. W. Coover: Polymerization with alkyl phosphite catalysts. U. S. Patent 2,652,393.Google Scholar
  38. 37.
    -, and J. G. McNally: Copolymers of Β,Β-difluoroacrylates. U. S. Patent 2,571,687 (1951).Google Scholar
  39. 38.
    -, and T. E. Stanin: Polymers of α-fluoroacetoxy acrylonitrile compounds. U. S. Patent 2,464,120 (1949).Google Scholar
  40. 39.
    --Polyfluoromethyl styrene. U. S. Patent 2,475,423 (1949).Google Scholar
  41. 40.
    --Alkenyl fluoroacetates. U. S. Patent 2,525,530 (1950).Google Scholar
  42. 41.
    Dishart, K. T., and R. Levine: A new synthesis of ketones containing one perfluoroalkyl group. J. Amer. chem. Soc. 78, 2268–2270 (1956).CrossRefGoogle Scholar
  43. 42.
    Dixson, S.: Elimination reactions of fluoroolefins with organolithium compounds. J. org. Chem. 21, 400–403 (1956).Google Scholar
  44. 43.
    Dow Corning Corporation: Data sheet, handling and processing Silastic LS-53. Midland, Michigan, 1957.Google Scholar
  45. 44.
    Frost, L. W.: Fluorine-containing organosilicon compounds. U. S. Patent 2,596,967 (1952).Google Scholar
  46. 45.
    -Trifluoromethylphenyl siloxanes. U. S. Patent 2, 636, 896 (1953).Google Scholar
  47. 46.
    Haas, H. C., E. S. Emerson and N. W. Schuler: Polyvinyl trifluoroacetate. J. Polymer Sci. 22, 291–302 (1956).Google Scholar
  48. 47.
    Halpern, B. D., W. Karo, L. Laskin, P. Levine and J. Zomlefer: Synthesis of monomeric materials. Wright Air Development Center Technical Report 54–264 (1954).Google Scholar
  49. 48.
    Haszeldine, R. N., and R. J. Marklow: Fluoroalkyl compounds of silicon. Abstracts 128 th Meeting Amer. chem. Soc. 43M (1955).Google Scholar
  50. 49.
    Hellmann, M., A. J. Bilbo and W. J. Pummer: Synthesis and properties of fluorinated polyphenyls. J. Amer. chem. Soc. 77, 3650–3651 (1955).CrossRefGoogle Scholar
  51. 50.
    Henne, A. L., and C. J. Fox: Ionization constants of fluorinated acids. III. Unsaturated acids. J. Amer. chem. Soc. 76, 479–481 (1954).Google Scholar
  52. 51.
    Howk, B. W., and R. A. Jacobson: Vinyl fluoroacetate polymers. U. S. Patent 2,436,144 (1948).Google Scholar
  53. 52.
    Hyde, J. F.: Siloxanes. U. S. Patent 2,629,725 (1953).Google Scholar
  54. 53.
    Izard, E. F., and S. L. Kwolek: Reaction of perfluoroalkyl chlorides with silicon. J. Amer. chem. Soc. 73, 1156–1158 (1951).Google Scholar
  55. 54.
    Jacobs, T. L., and R. S. Bauer: Tetrafluoroallene. J. Amer. chem. Soc. 78, 4814–4816 (1956).Google Scholar
  56. 55.
    Jones, F. B.: Battelle memorial institute. Private Communication.Google Scholar
  57. 56.
    -, P. B. Stickney, L. E. Coleman jr., D. A. Rausch and A. M. Lovelace: Polymerization of some fluorine-containing olefin oxides. J. Polymer Sci. 26, 81–88 (1957).Google Scholar
  58. 56A.
    Juve, A. E.: Crack growth in GR-S tread stocks. Ind. Eng. Chem. 39, 1494–1498 (1947).Google Scholar
  59. 57.
    Knobloch, F. W.: Polymers and copolymers of N-1,1-dihydrofluoroalkyl acrylamides. J. Polymer Sci. 25, 453–463 (1957).Google Scholar
  60. 58.
    -, and H. C. Hamlin: Polymers derived from dihydroperfluorobutyl acrylate. Wright Air Development Center Technical Report 55-25 (1955).Google Scholar
  61. 59.
    Kohl jr., C. F.: (Trifluoromethyl)phenylsilanols. U. S. Patent 2,640,063 (1953).Google Scholar
  62. 60.
    -Halohydrocarbon derivatives of silanes. U. S. Patent 2,530,202 (1950).Google Scholar
  63. 61.
    -Fluorocarbon substituted methylsiloxanes. U. S. Patent 2,571,090 (1951).Google Scholar
  64. 62.
    -Organosilicon compounds. U. S. Patent 2,640,066 (1953).Google Scholar
  65. 63.
    LaZerte, J. D., W. H. Pearlson, J. L. Rendall and T. J. Brice: Presented before the Fluorine Chemistry Symposium, 120th Meeting of the Amer. chem. Soc., New York 1951.Google Scholar
  66. 64.
    -, D. A. Rausch, R. J. Koshar, J. D. Park, W. H. Pearlson and J. R. Lacher: Perfluoroacrylonitrile and its derivatives. J. Amer. chem. Soc. 78, 5639–5641 (1956).CrossRefGoogle Scholar
  67. 65.
    Livingston, D. I., P. M. Kamath and R. S. Corley: Poly-α, Β,Β-trifluorostyrene. J. Polymer Sci. 20, 485–490 (1956).Google Scholar
  68. 66.
    McBee, E. T., and T. M. Burton: The preparation and properties of 3,3,3-trifluoro-1,2-epoxypropane. J. Amer. chem. Soc. 74, 3022–3023 (1952).Google Scholar
  69. 67.
    -, W. Marzluff and O. R. Pierce: The ionization constants of some fluorinecontaining alcohols. J. Amer. chem. Soc. 74, 444–446 (1952).Google Scholar
  70. 68.
    -, and O. R. Pierce: Fluorine-containing elastomers. Wright Air Development Center Technical Report 55-191, Part II (1953).Google Scholar
  71. 69.
    --and D. D. Smith: The ionization constants of some new fluorinecontaining acids. J. Amer. chem. Soc. 76, 3722–3725 (1954).CrossRefGoogle Scholar
  72. 70.
    -, C. W. Roberts, C. F. Judd and T. S. Chao: Reaction of Grignard reagents with alkoxysilanes at elevated temperatures. J. Amer. chem. Soc. 77, 1292–1293 (1955).Google Scholar
  73. 71.
    --and G. W. R. Puerckhauer: Addition of silicochloroform and methyl dichlorosilane to fluorine-containing olefins. J. Amer. chem. Soc. 79, 2326–2329 (1957).Google Scholar
  74. 72.
    -, and R. A. Sanford: Preparation and polymerization of trifluoromethyl-and chloro-(trifluoromethyl)-substituted styrenes. J. Amer. chem. Soc. 72, 4053–4055 (1950).Google Scholar
  75. 73.
    -, P. A. Wiseman and G. B. Bachmann: Perfluoro dibasic acids and derivatives. Ind. Engng. Chem. 39, 415–417 (1947).Google Scholar
  76. 74.
    McGinty, L.: α-fluoroacrylic esters and polymers thereof. British Patent 590,015 (1947).Google Scholar
  77. 75.
    -α-fluoroacrylic esters and polymers. U. S. Patent 2,454,663 (1948).Google Scholar
  78. 76.
    Manowitz, B.: The industrial future of radiation chemistry. Nucleonics 11, No. 10, 18–20 (1953).Google Scholar
  79. 77.
    Marvel, C. S., and D. W. Hein: o-methoxy-, p-benzyl-, o-fluoro-, and o-cyanostyrenes. Further examples of the disproportionation of phenylmethylcarbinols to ethylbenzenes. J. Amer. chem. Soc. 70, 1895–1898 (1948).Google Scholar
  80. 78.
    -, G. E. Inskeep, R. Deanin, A. E. Juve, C. H. Schroeder and M. M. Goff: Copolymers of butadiene with halogenated styrenes. Ind. Engng. Chem. 39, 1486–1490 (1947).CrossRefGoogle Scholar
  81. 79.
    ---, D. W. Hein, P. U. Smith, J. D. Young, A. E. Juve, C. H. Schroeder and M. M. Goff: Copolymers of butadiene with alkyl, aryl, alkoxyl, and phenoxyl styrenes. Ind. Engng. Chem. 40, 2371–2373 (1948).CrossRefGoogle Scholar
  82. 80.
    -, C. G. Overberger, R. E. Allen and J. H. Saunders: The preparation and polymerization of some substituted styrenes. J. Amer. chem. Soc. 68, 736–738 (1946).Google Scholar
  83. 81.
    Miller, W.T.: Perhaloacrylonitriles from perhaloolefins. U. S. Patent 2,691,036. (1954).Google Scholar
  84. 82.
    Park, J. D., M. L. Sharrah and J. R. Lacher: Action of an alcohol on perfluorocyclobutene. J. Amer. chem. Soc. 71, 2337–2339 (1949).Google Scholar
  85. 83.
    Passino, H. J., and L. C. Rubin: Organosilicon compounds. U. S. Patent 2,686,194 (1954).Google Scholar
  86. 84.
    Pierce, O. R., and E. T. McBee: Fluorine-containing elastomers. Wright Air Development Center Technical Report 52-191, Part I (1952).Google Scholar
  87. 85.
    --Chlorine-and fluorine-containing compounds for nonflammable materials. Wright Air Development Center Technical Report 53-462 (1954).Google Scholar
  88. 86.
    --and R. E. Cline: The synthesis of fluorine-containing organosilanes. J. Amer. chem. Soc. 75, 5618–5620 (1953).Google Scholar
  89. 87.
    --and A. F. Judd: Preparation and reactions of perfluoroalkyllithiums. J. Amer. chem. Soc. 76, 474–478 (1954).Google Scholar
  90. 88.
    Postelnek, William: Air force polymer development program. Rubber World 543–545 (July 1957).Google Scholar
  91. 89.
    Prober, M.: Fluorinated styrenes. U. S. Patent 2,651,627 (1953).Google Scholar
  92. 90.
    Rathmann, G. B., and F. A. Bovey: Fluorine-containing polymers. V. Light scattering and viscosity study of poly-1,1-dihydroperfluorobutyl acrylate. J. Polymer Sci. 15, 544–552 (1955).Google Scholar
  93. 91.
    Rausch, D. A., L. E. Coleman jr. and A. M. Lovelace: α, Β-unsaturated ketones. I. The preparation and polymerization of perfluoroalkyl propenyl ketones. J. Amer. chem. Soc. 79, 4983–4984 (1957).CrossRefGoogle Scholar
  94. 92.
    -, A. M. Lovelace and L. E. Coleman jr.: The preparation and properties of some fluorine-containing epoxides. J. org. Chem. 21, 1328–1330 (1956).Google Scholar
  95. 93.
    Reid, T. S., D. W. Codding and F. A. Bovey: Vinyl esters of perfluoro acids. J. Polymer Sci. 18, 417–421 (1955).Google Scholar
  96. 94.
    Renoll, M. W.: Vinyl aromatic compounds. III. Fluorinated derivatives. J. Amer. chem. Soc. 68, 1159–1161 (1946).CrossRefGoogle Scholar
  97. 95.
    -Trifluoromethyl derivatives of vinyl aromatic compounds. U. S. Patent 2,313,330.Google Scholar
  98. 96.
    -Rubbery copolymers of (trifluoromethyl)vinyl aromatic compounds. U. S. Patent 2,469,845.Google Scholar
  99. 97.
    -: An introduction to the chemistry of the silicones (2nd Ed.). New York: John Wiley and Sons, Inc. 1951.Google Scholar
  100. 98.
    Sandberg, C. L., and F. A. Bovey: Fluorine-containing polymers. VI. Copolymerization of 1,1-dihydroperfluorobutyl acrylate. J. Polymer Sci. 15, 553–557 (1955).Google Scholar
  101. 99.
    Schweiker, G. C., and P. Robitschek: Condensation polymers containing fluorine. I. Synthesis of linear polyesters from fluorine-containing diols. J. Polymer Sci. 24, 33–41 (1957).Google Scholar
  102. 100.
    -, R. R. White and R. N. Deleo: Investigation of condensation type elastomers. Wright Air Development Center Technical Report 55-221, Part I (1955).Google Scholar
  103. 101.
    ---Investigation and condensation type elastomers. Wright Air Development Center Technical Report 55-221, Part II (1956).Google Scholar
  104. 102.
    -, B. S. Marks, R. R. White and R. N. Deleo: Investigation of condensation type elastomers. Wright Air Development Center Technical Report 55-221, Part III (1956).Google Scholar
  105. 103.
    Seymour, D., and K. B. Wolfstirn: Substituted styrenes. III. The preparation of some m-and p-substituted α-methylstyrenes. J. Amer. chem. Soc. 70, 1177–1179 (1948).CrossRefGoogle Scholar
  106. 104.
    Simons, J. H., and R. D. Dunlap: Silicon halides containing fluorocarbon radicals. U. S. Patent 2,651,651 (1953).Google Scholar
  107. 105.
    Smith, D. D., R. M. Murch and O. R. Pierce: Fluorine-containing polyethers. Ind. Engng. Chem. 49, 1241–1246 (1957).Google Scholar
  108. 106.
    Sommer, L. H., E. W. Pietrusza and F. C. Whitmore: Peroxide-catalyzed addition of trichlorosilane to 1-octene. J. Amer. chem. Soc. 69, 188 (1947).Google Scholar
  109. 107.
    Stedry, P. J., J. F. Abere and A. M. Borders: Fluorine-containing polymers. VII. 1,1-dihydroperfluoroalkyl acrylates: compounding and properties of the vulcanizates. J. Polymer Sci. 15, 558–574 (1955).Google Scholar
  110. 108.
    Stump jr., E. C.: Preparation and polymerization of some fluoroalkylcyclosiloxanes. Wright Air Development Center Technical Report 56-493 (1957).Google Scholar
  111. 109.
    Tarrant, P., G. W. Dykes, F. F. Norris and D. E. O'Conner: The addition of perhaloalkanes to vinyl silanes. Abstracts 128 th Meeting American Chemical Society 47 M (1955).Google Scholar
  112. 110.
    Wagner, G. H.: Reactions of silanes with aliphatic unsaturated compounds. U. S. Patent 2,637,738 (1953).Google Scholar
  113. 111.
    Walborsky, H. M., and M. Schwarz: Addition Reactions to ethyl γ,γ,γ-trifluorocrotonate. J. Amer. chem. Soc. 75, 3241–3243 (1953).Google Scholar
  114. 112.
    Walling, C., and K. B. Wolfstirn: Substituted styrenes. I. The decarboxylation of substituted cinnamic acids. J. Amer. chem. Soc. 69, 852–854 (1947).CrossRefGoogle Scholar
  115. 113.
    Westinghouse Electric International Co.: British Patent 706, 703 (1954).Google Scholar

Copyright information

© Springer-Verlag 1958

Authors and Affiliations

  • William Postelnek
    • 1
  • Lester E. Coleman
    • 1
  • Alan M. Lovelace
    • 1
  1. 1.Materials LaboratoryWright Air Development Center, USAF Air Research and Development CommandWright-Patterson AFB

Personalised recommendations