Multifunctional acrylates and the synthesis thereof

Organic compounds -- part of the class 532-570 series – Organic compounds – Silicon containing

Patent

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

560144, 560254, 560261, C07F 708

Patent

active

053809017

ABSTRACT:
The present invention provides a process for converting a hydrophobic siloxane diacrylate, an aromatic fluorinated diacrylate and a hydrophilic polyethylene glycol diacrylate to their respective multifunctional oligomers. Bis(4-acryloxybutyl)tetramethyldisiloxane, prepared from the corresponding diol, is converted to relatively low viscosity, multifunctional oligomers with the use of DMSO. The hydrophilic monomer, polyethylene glycol 400 diacrylate, formed more viscous, water soluble oligomeric products without the need for a solvent. Characterization of these oligomers by infrared spectroscopy and .sup.1 H NMR supports the assigned structures. Because of the predominant 1,6-arrangement of double bonds in these oligomers, they have a propensity to undergo cyclopolymerization as well as the usual crosslinking associated with the free radical polymerization of multifunctional monomers and oligomers. These novel oligomeric monomers have potential use in dental composites, sealants, adhesives, dentures, contact lenses, biomedical prostheses, cements, drug delivery systems, coatings and caulks.

REFERENCES:
patent: 3066165 (1962-11-01), Rosenthal et al.
patent: 3288883 (1966-11-01), Temin et al.
patent: 3743669 (1973-07-01), Hillman et al.
patent: 3810938 (1974-05-01), Schmitt et al.
patent: 3835090 (1974-06-01), Gander et al.
patent: 3923740 (1975-12-01), Schmitt et al.
patent: 4041061 (1977-08-01), Buck
patent: 4041062 (1977-08-01), Buck
patent: 4041063 (1977-08-01), Buck
patent: 4067853 (1978-01-01), Schmitt et al.
patent: 4308014 (1981-12-01), Kawahara et al.
patent: 4330283 (1982-05-01), Michl et al.
patent: 4406625 (1983-09-01), Orlowski et al.
patent: 4433958 (1984-02-01), Fellmen et al.
patent: 4458087 (1984-07-01), McAlister
patent: 4572920 (1986-02-01), Rawls et al.
patent: 4692537 (1987-09-01), McAlister
patent: 4760122 (1988-07-01), Nakos et al.
patent: 4778915 (1988-10-01), Lina et al.
patent: 4843136 (1989-06-01), Reiners et al.
patent: 4889948 (1989-12-01), Mathias
patent: 4940766 (1990-07-01), Gay et al.
patent: 4946977 (1990-08-01), Bernhardt et al.
patent: 4981903 (1991-01-01), Garbe et al.
patent: 5010141 (1991-04-01), Mueller
patent: 5039761 (1991-08-01), Ono et al.
patent: 5117027 (1992-05-01), Bernhardt et al.
patent: 5145374 (1992-09-01), Stansbury
Mathias et al., (Mathias, L. J.; Kusefoglu, S. H.), Macromolecules, 1987, , pp. 2039-2041.
Mathias et al., (Mathias, L. J.; Kusefoglu, S. H., Ingram, J. E.), Macromolecules, 1988, 21, pp. 545-546.
"Synthesis of Novel Polyfluorinated Acrylic Monomers and Oligomers", J. M. Antonucci and J. W. Stansbury, published in Polymer Preprints 34, Mar. 5, 1993.
Stansbury, J. W., J. Dent Red. 1990, 69, pp. 844-848.
Mathias, L. J.; Dickerson, C. W., J. Polym, Sci., Polym, Lett., 1990, 28, p. 175.
Butler, G. B., In: Proceedings of the International Symposium on Macromolecules, E. B. Mano, Ed., New York: Elsevier Scientific Publishing Company, 1975 pp. 57-76.
"A Facile Synthesis of Novel Fluorinated Multifunctional Acrylates", Antonucci, J. M., Stansbury J. W., and Cheng, G. W.; NIST Polymer Division, Gaithersburg, Md. 20899.
Antonucci, J. M.; Stansbury, J. W. Cheng, G. W., Polym. Prepr. 1990, 31(1), p. 320.
Antonucci, J. M.; Stansbury, J. W. Cheng, G. W., "A Facile Synthesis of Novel Fluorinated Multifunctional Acrylates"; 199th mtg. Amer. Chem. Soc.; Boston Mass.; Apr. 24, 1990.
"Synthesis of Novel Highly Fluorinated Multifunctional Vinyl Monomers and Oligomers"; 68th General Session of the International Assoc. for Dental Research; Cincinnati Ohio; Mar. 10, 1990; Polym. Prepr., 1990, 31(1).
Marvel, C. S., "Intramolecular-IntermolecularPolymerization of Nonconjugated Diolefins"; J. Of Polymer Science 1960 vol. XLVIII, pp. 101-108.
Stansbury, J. W., "Synthesis and Evaluation of New Oxaspero Monomer for Double Ring Opening Polymerization"; J. Dent Res., 1992 (71), pp. 1408-1412.
Colletti, R. I. et al. "Merchanism Study of the Base Catalyzed Ether Formation Involving .alpha.-(Hydroxymethyl)Acrylates"; Macromolecules, 1991, 24, pp. 2043-2047.
Drewes L. et al., Synth. Commun., 1987, 17(3) pp. 291-298.
Amri et al., "Hydroxyalkylation de la MethylvinylcentoneetDe L'Acrylonitrile en Presence de Diazo-1,4 Bicyclo [2.2.2]. Octane," 27 Tetrahedron Letters, 1982, pp. 924-926.
Villieras et al., "An easy synthesis of Ethyl .alpha.-Halomethylacrylates Using Formaldehyde in Water", Synthesis, Wittig-Horner Reaction in Heterogeneous Media:1, 1982, pp. 924-926.
D. Breslow, "A Polymer That Fights Cancer", Chemtech, 1985, pp. 302-307.
J. W. Cheng, et al., Abstract #994 "Synthesis of Novel Highly Fluorinated Multifunctional Vinyl Monomers and Oligomers", J. Denkes, 1990, 69, p. 233.

LandOfFree

Say what you really think

Search LandOfFree.com for the USA inventors and patents. Rate them and share your experience with other people.

Rating

Multifunctional acrylates and the synthesis thereof does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Multifunctional acrylates and the synthesis thereof, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Multifunctional acrylates and the synthesis thereof will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-852107

  Search
All data on this website is collected from public sources. Our data reflects the most accurate information available at the time of publication.