Acrylic (and Methacrylic) Acid Polymers
1
Graham Swift,
Graham Swift
Consultant
GS Polymer Consultants, Chapel Hill, North Carolina
Search for more papers by this authorGraham Swift,
Graham Swift
Consultant
GS Polymer Consultants, Chapel Hill, North Carolina
Search for more papers by this authorAbstract
Acrylic polymers are widely used because of their unique properties. This article selectively focuses on polymers that contain acrylic acid and/or methacrylic acid. Their content ranges from <5 wt% to 100 wt% for use in applications such as adhesives, coatings, water-soluble specialties, and superabsorbent gels. Acidic monomer selection and use may be based on monomer properties and characteristics, but is frequently based only on cost and availability, and this generally tips the choice to acrylic acid. As described, many polymer applications require optimized compositions and molecular weights that are uniquely available only by one of several different polymerization processes such as solution, emulsion, and graft, so as to accomplish commercial viability.
Bibliography
- 1
J. Redtenbacher,
Annalen
47,
125
(1843).
10.1002/jlac.18430470202 Google Scholar
- 2 J. W. Nemec and W. Bauer Jr., in M. Grayson, ed., Kirk-Othmer Encyclopedia of Chemical Technology, 3rd ed., Vol. 1, Wiley-Interscience, New York, 1978, pp. 330–354.
- 3 E. Frankland and B. F. Duppa, Ann. 136, 1 (1865).
- 4 J. W. Nemec and L. Kirch, in M. Grayson, ed., Kirk-Othmer Encyclopedia of Chemical Technology, 3rd ed., Vol. 15, Wiley-Interscience, New York, 1981, pp. 346–376.
- 5 E. H. Riddle, Monomeric Acrylic Esters, Reinhold Publishing Corp., New York, 1954.
- 6 M. Salkind, E. H. Riddle, and R. W. Keefer, Ind. Eng. Chem. 51, 1232 (1959).
- 7 L. S. Luskin, in E. C. Leonard, ed., High Polymers, Vinyl and Diene Monomers, Pt. 1, Vol. 24, Wiley-Interscience, New York, 1970, pp. 105–203.
- 8 L. S. Luskin, in F. D. Snell and C. L. Hilton, eds., Encyclopedia of Industrial Chemical Analysis, Vol. 4, John Wiley & Sons, Inc., New York, 1967, p. 181.
- 9 V. A. Kabanov and co-workers, Eur. Polym. J. 11, 153 (1975).
- 10 G. Blauer, Trans. Faraday Soc. 56, 606 (1960).
- 11
H. Ito,
S. Shimizu, and
S. Suzuki,
Kogyo Kagaku Zasshi
58,
194,
278
(1958).
10.1246/nikkashi1898.58.194 Google Scholar
- 12 S. Suzuki, H. Ito, and S. Shimizu, Kogyo Kagaku Zasshi 57, 658 (1954).
- 13 Y. Kikuchi and K. Yamaoka, J. Sci. Hiroshima Univ. Ser. A 21, 143 (1957).
- 14 J. Brandrup and E. H. Immergut, Polymer Handbook, 4th ed., John Wiley & Sons., Inc., New York, 1999.
- 15 L. J. Young, J. Polym. Sci. 54, 411 (1961).
- 16U.S. Pats. 5352726 (Oct. 4, 1994) and 5912297 (June 15, 1999), W. Hall (both to Henkel Corp.).
- 17Eur. Pat. Appl. EP 942098 (Sept. 15, 1999) (to National Starch).
- 18U.S. Pat. 5912293 (June 15, 1999) (to Allied Colloids).
- 19World Pat. WO 9936192 (July 22, 1999) (to Henkel Corp.).
- 20World Pat. WO 9923183 (May 14, 1999) (to Hewlett-Packard Co.).
- 21U.S. Pat. 5902853 (May 11, 1999), A. Rudin (to Xerox Corp.).
- 22Eur. Pat. Appl. EP 902073 (Mar. 17, 1999) (to Nippon Mektron).
- 23Ger. Offen. DE 19757669 (Jan. 7, 1999) (to BASF AG).
- 24World Pat. WO 9849205 (Nov. 5, 1998) (to Waker-Chemie GmbH).
- 25Ger. Offen. DE 19653524 (June 25, 1998) (to BASF AG).
- 26U.S. Pat. 5795932 (Aug. 18, 1998) (to Sequa Chemicals, Inc.).
- 27Euro. Pat. Appl. EP 814140 (Feb. 29, 1997) (to Hercules, Inc.).
- 28Ger. Offen. DE 19627204 (Jan. 8, 1998) (to BASF AG).
- 29Pol. Pat. PL 165052 (Nov. 30, 1994) (to Instytut Mechaniki Precyzyjnej).
- 30World Pat. WO 9709031 (Mar. 13, 1997) (to Procter & Gamble Co.).
- 31World Pat. WO 9715616 (May 1, 1997) (to Rhone-Poulenc Chimie).
- 32Eur. Pat. Appl. EP 727451 (Aug. 21, 1996) (to Rohm and Haas Co.).
- 33Eur. Pat. Appl. EP 213895 (Mar. 11, 1987) (to Hercules Inc.).
- 34Eur. Pat. Appl. EP 697423 (Feb. 21, 1996) (to Allied Colloids Ltd.).
- 35Ger. Offen. DE 4419216 (Aug. 31, 1995) (to Bollig and Kemper KG).
- 36Eur. Pat. Appl. EP 601518 (June 15, 1994) (to Air Products and Chemicals).
- 37World Pat. WO 9402112 (Feb. 3, 1994) (to National Starch and Chemical Investments Holding Corp.).
- 38Eur. Pat. Appl. EP 522791 (Jan. 13, 1993) (to Rohm and Haas Co.).
- 39U.S. Pat. 4916171 (Apr. 10, 1990) (to Rohm and Haas Co.).
- 40Eur. Pat. Appl. EP 348565 (Jan. 3, 1990) (to Rohm and Haas Co.).
- 41U.S. Pat. 4876313 (Jan. 24, 1989) (to Rohm and Haas Co.).
- 42Eur. Pat. Appl. EP 338486 (Jan. 25, 1989) (to S. C. Johnson and Sons, Inc.).
- 43Brit. Pat. BR 8705620 (Aug. 16, 1988) (to BASF Corp.).
- 44Eur. Pat. Appl. EP 258753 (Mar. 9, 1988) (to S. C. Johnson and Sons, Inc.).
- 45U.S. Pat. 4477623 (Jan. 16, 1984) (to Synres International).
- 46 D. C. Blackley, Emulsion Polymerization, Applied Science Publishers, Barking, 1975; R. G. Gilbert, Emulsion Polymerization: A Mechanistic Approach, Academic Press, Inc., New York, 1995.
- 47CN 1176986 (Mar. 25, 1998) (to Changsha Electric Powder College, PRC).
- 48
D. Y. Lee and
J. H. Kim,
J. Polym. Sci., Part A: Polym. Chem.
36,
2865–2872
(1998).
10.1002/(SICI)1099-0518(19981130)36:16<2865::AID-POLA4>3.0.CO;2-7 CAS Web of Science® Google Scholar
- 49Eur. Pat. Appl. EP 245021 (Nov. 11, 1987) (to The Dow Chemical Co.).
- 50Ger. Offen. DE 3522419 (Jan. 2, 1987) (to Chemische Fabrik Stockhausen GmbH).
- 51Eur. Pat. Appl. EP 555959 (Aug. 18, 1993) (to Rohm and Haas Co.).
- 52World Pat. WO 9511265 (Apr. 27, 1995) (to Lucky Ltd.).
- 53Ger. Offen DE 4345086 (July 21, 1994) (to Toyo Boseki KK).
- 54Eur. Pat. Appl. EP 565825 (Feb. 1, 1993) (to Huels).
- 55U.S. Pat. 4994537 (Feb. 19, 1991) (to Hercules, Inc.).
- 56World Pat. WO 9008786 (Aug. 9, 1990) (to Akzo NV).
- 57Eur. Pat. Appl. EP 252526 (Jan. 13, 1988) (to Hercules, Inc.).
- 58World Pat. WO 9614357 (May 17, 1996) (to Hercules, Inc.).
- 59Eur. Pat. Appl. EP 767180 (Apr. 9, 1997) (to Elf Atochem Italia SRL).
- 60 L. S. Park and co-workers, Pollimo 14, 583–589 (1990).
- 61 D.-Y. Lee and J.-H. Kim, Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.) 38, 418–419 (1997).
- 62 D. Steinkopff, Prog. Colloid Polym. Sci., Vol. 110 (Trends in Colloid and Interface Science XII), 1998, pp. 99–104.
- 63 D. Charmont, J. F. D'Allest, and F. Dobler, DECHEMA Monograph 131 (5th International Workshop on Polymer Reaction Engineering), 1995, pp. 113–121.
- 64 D. Charmont, J. F. D'Allest, and F. Dobler, Polymer 37, 5237–5245 (1996).
- 65 D. E. Mestach and W. H. Baan, DECHEMA Monograph 131 (5th International Workshop on Polymer Engineering), 1995, pp. 35–44.
- 66 P. Hernandez and co-workers, Annu. Tech. Conf. Soc. Plast. Eng. 52, 1672–1674 (1994).
- 67 D.-Y. Lee and co-workers, Langmuir 15, 8252–8258 (1999).
- 68 I. C. Hodges, J. Hearn, and M. C. Wilkinson, Polym. Mater. Sci. Eng. 81, 185–186 (1999).
- 69 Y.-J. Park and co-workers, Colloid Polym. Sci. 276, 709–714 (1998).
- 70
H. Kast,
Makromol. Chem.
10/11,
447–461
(1985).
10.1002/macp.1985.020101985131 Google Scholar
- 71U.S. Pat. 5866664 (Feb. 2, 1999), B. Weinstein (to Rohm and Haas Co.).
- 72Eur. Pat. Appl. EP 405818 (Jan. 2, 1991), G. Swift and K. Hughes (to Rohm and Haas Co.).
- 73Fr. Pat. FR 2751335 (Jan. 23, 1998) (to Coatex A. S.).
- 74Ger. Offen. DE 3346350 (June 13, 1985) (to Benckiser-Knapsack GmbH).
- 75U.S. Pat. 6932671 (Aug. 3, 1999) (to Phillips Petroleum Co.).
- 76Ger. Offen. DE 3620149 (Dec. 17, 1987) (to Roehm GmbH).
- 77U.S. Pat. 5298585 (Mar. 29, 1994), B. Weinstein and co-workers (to Rohm and Haas Co.).
- 78Eur. Pat. Appl. EP 429307 (May 29, 1991) (to Rohm and Haas Co.).
- 79Eur. Pat. Appl. EP 441022 (Aug. 14, 1991) (to Rohm and Haas Co.).
- 80Eur. Pat. Appl. EP 430574 (June 5, 1991) (to Rohm and Haas Co.).
- 81Eur. Pat. Appl. EP 534695 (Mar. 31, 1993) (to Rohm and Haas Co.).
- 82Pol. Pat. PL 164268 (July 29, 1994), S. Kudla (to Inst. Ciezkiej Syntezy Organicznej).
- 83Uzbekistan 1641831 (Apr. 15, 1991) (to Institute of Chemistry, Acad. Sci.).
- 84Eur. Pat. Appl. EP 398724 (Nov. 22, 1990) (to Rohm and Haas Co.).
- 85Ger. Offen. DE 3621429 (Jan. 8, 1987) (to Milchem, Inc.).
- 86CA 1274942 (Oct. 2, 1990) (to BASF).
- 87 H. Hu and co-workers, Gaofenzi Xuebao 6, 740–743 (1998).
- 88Ger. Offen. DE 3519013 (Nov. 27, 1986) (to BASF AG).
- 89 D. Fong, J. Macromol. Sci., A: Pure Appl. Chem. 35, 401–409 (1998).
- 90BE 905996 (June 19, 1987) (to Nalco Chemical Co.).
- 91AT 395592 (Jan. 25, 1993) (to Nalco Chemical Co.).
- 92U.S. Pat. 4604431 (Aug. 5, 1986) (to Nalco Chemical Co.).
- 93U.S. Pat. 5360570 (Nov. 1, 1994) (to Rohm and Haas Co.).
- 94U.S. Pat. 5100980 (Mar. 31, 1995) (to Rohm and Haas Co.).
- 95U.S. Pat. 5223590 (June 29, 1993) (to Rohm and Haas Co.).
- 96U.S. Pat. 5430114 (July 4, 1995) (to Rohm and Haas Co.).
- 97Ger. Offen. DE 3812402 (Jan. 26, 1989) (to BASF AG).
- 98World Pat. WO 9635728 (Nov. 14, 1996) (to Stockhausen).
- 99World Pat. WO 9401477 (Jan. 20, 1944) (to Stockhausen).
- 100Ger. Offen. DE 3818426 (Dec. 9, 1989) (to BASF AG).
- 101U.S. Pat. 5482647 (Jan. 9, 1996) (to Church and Dwight Co.).
- 102World Pat. WO 9742282 (Nov. 13, 1997) (to The Procter & Gamble Co.).
- 103World Pat. WO 9813452 (Apr. 2, 1998) (to The Procter & Gamble Co.).
- 104Eur. Pat. Appl. EP 877076 (Nov. 11, 1998) (to Rohm and Haas Co.).
- 105Eur. Pat. Appl. EP 893491 (Jan. 27, 1990) (to Unilever PLC).
- 106World Pat. WO 9958633 (Nov. 18, 1999) (to Unilever PLC).
- 107GB 2322137 (Aug. 19, 1998) (to Unilever PLC).
- 108U.S. Pat. 5516432 (May 14, 1996) (to Rohm and Haas Co.).
- 109World Pat. WO 9710180 (Mar. 20, 1997) (to Ashland, Inc.).
- 110U.S. Pat. 5866013 (Feb. 2, 1999) (to BetzDearborn, Inc.).
- 111Eur. Pats. Appl. EP 774506 and EP 774507 (May 21, 1997) (both to Rohm and Haas Co.).
- 112Ger. Offen. DE 4328817 (Mar. 2, 1995) (to BASF AG).
- 113Eur. Pat. Appl. EP 924174 (June 23, 1999) (to Takemoto Yushi KK).
- 114World Pat. WO 9947468 (Sept. 23, 1999) (to Lafarge SA).
- 115Eur. Pat. Appl. EP 940374 (Sept. 8, 1999) (to Takemoto Yushi KK).
- 116Ger. Offen. DE 19830760 (Jan. 13, 2000) (to SKW Trostberg AG).
- 117Rom. Pat. 100582 (Oct. 28, 1991) (to Intreprinderea Chimica Risnov).
- 118U.S. Pat. 5854177 (Dec. 29, 1998) (to Donlar Corp.).
- 119Eur. Pats. Appl. EP 812888 (Dec. 17, 1997) and EP 908496 (Apr. 14, 1999) (both to Seiko Epson Corp.).
- 120AU 613925 (Aug. 15, 1991) (to Ciba-Geigy AG).
- 121U.S. Pats. 5726267 (Mar. 10, 1998) and 5880237 (Mar. 9, 1999) (both to Nalco Corp.).
- 122Eur. Pat. Appl. EP 737656 (Oct. 16, 1996) (to Rohm and Haas Co.).
- 123World Pat. WO 9718271 (May 22, 1997) (to Allied Colloids Ltd.).
- 124Eur. Pat. Appl. EP 796876 (Sept. 24, 1997) (to National Starch and Chemical Investments Holding Corp.).
- 125Eur. Appl. EP 649864 (Apr. 26, 1995) (to Wolff Walsrode AG).
- 126CN 1152587 (June 25, 1997) (to Sichuan University).
- 127Ger. Pat. DE 3418397 (Dec. 6, 1984) (to Sanyo Chemicals Industries Ltd.).
- 128Eur. Pat. Appl. EP 483638 (May 6, 1992) (to Hoechst AG).
- 129U.S. Pat. 4728445 (Mar. 1, 1988) (to Pony Industries, Inc.).
- 130CA 1176049 (Oct. 16, 1984) (to Katayama Chemical Works).
- 131U.S. Pat. 4756881 (July 12, 1988) (to Nalco Chemical Co.).
- 132AU 595599 (Apr. 5, 1990) (to Betz International, Inc.).
- 133Eur. Pat. Appl. EP 526786 (Feb. 10, 1993) (to Nalco Chemical Co.).
- 134U.S. Pat. 5308498 (May 3, 1994) (to Nalco Chemical Co.).
- 135Eur. Pat. Appl. EP 674022 (Sept. 27, 1995) (to Betz Europe, Inc.).
- 136GB 2299331 (Oct. 2, 1996) (to Nalco Chemical Co.).
- 137Eur. Appl. EP 713890 (May 29, 1996) (to Hercules, Inc.).
- 138U.S. Pat. 4828713 (May 9, 1989) (to Betz Laboratories, Inc.).
- 139U.S. Pat. 5271847 (Dec. 21, 1993) (to Betz Laboratories, Inc.).
- 140U.S. Pat. 5078891 (Jan. 7, 1992) (to Betz Laboratories, Inc.).
- 141Eur. Pat. Appl. EP 459661 (Dec. 4, 1991) (to Rohm and Haas Co.).
- 142U.S. Pat. 5783200 (July 21, 1998) (to The Procter & Gamble Co.).
- 143CA 1204361 (May 13, 1986) (to Bristol Myers Co.).
- 144World Pat. WO 9426858 (Nov. 24, 1994) (to Unilever PLC).
- 145U.S. Pat. 4869934 (Sept. 26, 1989) (to Sterling Drug, Inc.).
- 146U.S. Pat. 4861511 (Aug. 29, 1989) (to Nalco Chemical Co.).
- 147World Pat. WO 9830251 (July 16, 1998) (to Damar Holdings SA).
- 148U.S. Pat. 5256303 (Jan. 26, 1993) (to Nalco Chemical Co.).
- 149U.S. Pat. 5643462 (July 1, 1997) (to BetzDearborn, Inc.).
- 150Eur. Pat. Appl. EP 415141 (Mar. 6, 1991) (to Chemie Linz GmbH).
- 151Ger. Offen. DE 3713348 (Nov. 10, 1988) (to BASF AG).
- 152 R. J. Larson and co-workers, J. Environ. Polym. Degrad. 5(1), 41–48 (1997).
- 153Eur. Pat. Appl. EP 785431 (July 23, 1997) (to Rohm and Haas Co.).
- 154World Pat. WO 9735192 (Sept. 25, 1997) (to Nalco Chemical Co.).
- 155U.S. Pats. 4628071 (Dec. 9, 1986), 5073591 (Dec. 17, 1991), and 5093396 (Mar. 3, 1992) (all to S. C. Johnson and Sons, Inc.).
- 156Ger. Offen. DE 19617633 (Nov. 6, 1997) (to BASF AG).
- 157Eur. Pat. Appl. EP 317662 (May 31, 1989) (to Goodyear Tire and Rubber).
- 158U.S. Pat. 4728696 (Mar. 1, 1988) (to The Dow Chemical Company).
- 159U.S. Pat. 4514552 (Apr. 30, 1985) (to DeSoto, Inc.).
- 160U.S. Pat. 5292828 (Mar. 8, 1994) and World Pat. WO 9965958 (Dec. 23, 1999) (both to Union Carbide Chemicals and Plastics Technology Corp.).
- 161Eur. Pat. Appl. EP 896027 (Feb. 10, 1999) (to Rohm and Haas Co.).
- 162 G. D. Shay and A. F. Rich, J. Coat. Technol. 58(732), 42–53, 1986.
- 163 B. J. Van Rooden and T. M. S. Annen, Wochenbl. Papierfabr. 124, 854–861, (1996).
- 164 J. S. Berg, D. J. Lundberg, and E. J. Glass, Prog. Org. Coat. 17(2), 155–173 (1989).
- 165 A. Karunasena, S. K. Jongewaard, and E. J. Glass, Polym. Mater. Sci. Eng. 57, 632–636 (1987).
- 166 A. Karunesa and E. J. Glass, Polym. Mater. Sci. Eng. 56, 624–628 (1987).
- 167 S. K. Jongewaard, R. H. Fernando, and E. J. Glass, Polym. Mater. Sci. Eng. 54, 166–169 (1986).
- 168 C. W. Frank, D. J. Hemker, and H. T. Oyama, ACS Symposium Series, Vol. 467: Water-Soluble Polymers, American Chemical Society, New York, 1991, pp. 303–319.
- 169
K. C. Tam and co-workers,
J. Polym. Sci., Part B: Polym. Phys.
36,
2275–2290
(1998).
10.1002/(SICI)1099-0488(19980930)36:13<2275::AID-POLB4>3.0.CO;2-S CAS Web of Science® Google Scholar
- 170 D. Hourdet, F. L'Alloret, and R. Audebert, Polymer 38, 2535–2547 (1997).
- 171 F. L'Alloret, D. Hourdet, and R. Audebert, Colloid Polym. Sci. 273, 1163–1173 (1995).
- 172U.S. Pat. 4656222 (Apr. 7, 1987) (to Celanese Corp.).
- 173World Pat. WO 9736941 (Oct. 9, 1997) (to Cytec Technology Corp.).
- 174World Pat. WO 9929745 (June 17, 1999) (to Cytec Technology Corp.).
- 175Eur. Pat. Appl. EP 566930 (Jan. 27, 1993) (to BASF AG).
- 176 K. D. Branham and co-workders, Macromolecules 25, 1201–1206 (1992); Macromolecules 27, 5123–5128 (1994); Macromolecules 29, 254–262 (1996).
- 177World Pat. WO 9903895 (Jan. 28, 1999) (to Rhodia Chimie).
- 178Eur. Pat. Appl. EP 143935 (June 12, 1985) (to Belland AG).
- 179CA 2084851 (June 10, 1993) (to Hercules, Inc.).
- 180U.S. Pat. 4734205 (Mar. 29, 1988) (to Exxon Research and Engineering Co.).
- 181CA 1236939 (May 17, 1988) (to Nalco Chemical Co.).
- 182 D. Y. Lee, J. H. Kim, and T. I. Min, Colloid Surf. 153(1–3), 89–97 (1999).
- 183U.S. Pat. 4735981 (Apr. 5, 1988) (to DeSoto, Inc.).
- 184Eur. Pat. Appl. EP 644207 (Mar. 22, 1995) (to Nalco Chemical Co.).
- 185Eur. Pat. Appl. EP 522570 (Jan. 13, 1993) (to Mitsubishi Petrochemical Co., Ltd.).
- 186Eur. Pat. Appl. EP 530438 (Mar. 10, 1993) (to Hoechst Celanese Corp.).
- 187Ger. Offen. DE 4127814 (Mar. 12, 1992) and DE 4123889 (Mar. 12, 1992) (both to Sanyo Chemical Industries.).
- 188Eur. Pat. Appl. EP 409136 (Jan. 23, 1991), World Pat. WO 9008789 (Aug. 9, 1990), and Eur. Pat. Appl. EP 312952 (Apr. 26, 1989) (all to The Dow Chemical Company).
- 189U.S. Pat. 4921904 (May 1, 1990) (to Nalco Chemical Co.).
- 190Eur. Pat. Appl. EP 632068 (Jan. 4, 1995) (to Nippon Shokubai Co., Ltd.).
- 191U.S. Pat. 4698404 (Oct. 6, 1987) (to Nalco Chemical Co.).
- 192U.S. Pat. 4645789 (Feb. 24, 1987) (to Personal Products Co.).
- 193Eur. Pats. Appl. EP 827753 (Mar. 11, 1998) and EP 811636 (Dec. 10, 1997) (both to Nippon Shokubai Co., Ltd.).
- 194Ger. Offen. DE 19628863 (Jan. 23, 1997), DE 19637190 (Mar. 20, 1997), and GB 2313124 (Nov. 19, 1997) (all to Sanyo Chemical Industries).
- 195U.S. Pat. 5731387 (Mar. 24, 1998) (to Adhesives Research, Inc.).
- 196U.S. Pat. 5726250 (Mar. 10, 1998) (to Adhesives Research, Inc.).
- 197Eur. Pat. Appl. EP 283090 (Sept. 21, 1988) (to Shell International Research).
- 198U.S. Pats. 5338766 (Aug. 16, 1994) and 5328935 (July 12, 1994) (both to The Procter & Gamble Co.).
- 199Eur. Pat. Appl. EP 955086 (Nov. 10, 1999) (to Nippon Shokubai Co., Ltd.).
- 200Eur. Pat. Appl. EP 476263 (Mar. 25, 1992) (to American Cyanamid Co.).
- 201ZA 9104649 (Jan. 28, 1992) (to Chemical Services Ltd.).
- 202Ger. Offen. DE 4435425 (Apr. 11, 1996) (to BASF AG).
- 203World Pat. WO 9717055 (May 15, 1997) (to L'Oreal).
- 204U.S. Pat. 4671267 (June 9, 1987) (to E. I. Stout).
- 205Eur. Pat. Appl. EP 335653 (Oct. 4, 1989) (to Altalanos Iparfejlesztesi).
- 206U.S. Pat. 6011075 (Jan. 4, 2000) (to Schlumberger Technology Corp.).
- 207Eur. Pat. Appl. EP EP 970707 (Jan. 12, 2000) S. Morikane and D. Morikane (to Daiya Pharmaceutical Co., Ltd.).
- 208Eur. Pat. Appl. EP 429307 (May 29, 1991) (to Rohm and Haas Co.).
- 209Eur. Pat. Appl. 639592 (Feb. 22, 1995) (to Nippon Shokubai Co., Ltd.).
- 210World Pat. WO 2000002938 (Jan. 20, 2000) (to Rhodia Chimie).
- 211Ger. Offen. DE 4343993 (June 29, 1995) (to Stockhausen).
- 212Eur. Pat. Appl. EP 725093 (Aug. 7, 1996) (to BASF Corp.).
- 213Eur. Pat. Appl. EP 321913 (June 28, 1989) (to S. C. Johnson and Sons, Inc.).
- 214World Pat. WO 9619512 (June 27, 1996) (to Zeneca).
- 215Eur. Pat. Appl. EP 465287 (Jan. 8, 1992) (to Rhone-Poulenc Chimie).
- 216Eur. Appl. EP 725131 (Aug. 7, 1996) (to BASF Corp.).
- 217World Pat. WO 9321244 (Jan. 28, 1993) (to Raision Tehtaat Oy AB).
- 218Ger. Offen. DE 4201452 (July 22, 1993) (to BASF AG).
- 219Ger. Offen. DE 4038908 (June 11, 1992) (to BASF AG).
- 220Eur. Pat. Appl. EP 356241 (Feb. 28, 1990) (to Allied Colloids Ltd.).
- 221DE 3613309 (Jan. 22, 1987) (to Huels AG).
- 222 M. Yoshinobu, M. Morita, and I. Sakata, Sen'i Gakkaishi 47(2), 102–108 (1991).
- 223 L. Zhang and A. F. Johnson, China J. Polym. Sci. 11(2), 144–152 (1993).
- 224 Y. Tsukahara and co-workders, J. Polym. Sci., Part A: Polym. Chem. 27, 1099–1114 (1989).
- 225Eur. Pat. Appl. EP 851012 (July 1, 1998) (to E. I. du Pont de Nemours & Co., Inc.).
- 226 R. Xiong, G. Wei, and Y. Zhang, Gongye Shuichuli 18(6), 11–13 (1998).
- 227Ger. Offen. DE 19634328 (Apr. 1, 1997) (to Elf Atochem).
- 228 L. Zhang, R. Barlow, and A. Eisenberg, Macromolecules 28, 6055–6066 (1995).
- 229 C. S. Patrickios and co-workders, Langmuir 15, 1613–1620 (1999).
- 230CN 1152053 (June 18, 1997), S. Yu and X. Li.
- 231U.S. Pat. 4753981 (June 28, 1988) (to Phillips Petroleum Co.).
- 232U.S. Pat. 4745154 (May 17, 1988) (to Alco Chemical Corp.).
- 233Eur. Pat. Appl. EP 153506 (Sept. 4, 1985) and U.S. Pat. 4524175 (June 18, 1985) (both to The Dow Chemical Company).
- 234U.S. Pats. 6011089 (Jan. 4, 2000), 5869542 (Feb. 9, 1999), and 5849862 (Dec. 15, 1998) (all to Cytec).
“Acrylic Acid Polymers” in EPST 1st ed., Vol. 1, pp. 197–226, by M. L. Miller, American Cyanamid Co.; “Acrylic and Methacrylic Acid Polymers” in EPSE 2nd ed., Vol. 1, pp. 211–234, by J. W. Nemec and W. Bauer Jr., Rohm and Haas Co.
