Monomers for double ring-opening polymerization with expansion

Details Monomers for double ring-opening polymerization with expansion Monomers for double ring-opening polymerization with expansion

1992-03-06

1994-11-08

Schofer, Joseph L.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D49310

Patent

active

053628896

ABSTRACT:
Spiromonomers with enhanced reactivity and ring-opening proficiency of the formulae: ##STR1## wherein R.sub.1 represents a C.sub.1 -C.sub.6 alkenyl, R.sub.2 represents hydrogen or C.sub.1 -C.sub.6 alkenyl, R.sub.3 represents a C.sub.1 -C.sub.6 alkyl or C.sub.3 -C.sub.8 cycloaliphatic unsubstituted, or substituted with halo, C.sub.1 -C.sub.6 alkyl, alkoxy, hydroxy, or one of one or more hetero atoms; and R.sub.4 represents a C.sub.1 -C.sub.6 alkyl or C.sub.3 -C.sub.8 cycloaliphatic unsubstituted, or substituted with halo, C.sub.1 -C.sub.6 alkyl, alkoxy, hydroxy, or one of one or more hetero atoms; formula (II) ##STR2## wherein R.sub.5 is a C.sub.1 -C.sub.6 alkenyl; R.sub.6 represents hydrogen or C.sub.1 -C.sub.6 alkenyl; R.sub.7 is a C.sub.1 -C.sub.6 alkenyl or C.sub.3 -C.sub.8 cycloaliphatic unsubstituted, or substituted with halo, C.sub.1 -C.sub.6 alkyl, alkoxy, hydroxy, or one of one or more hetero atoms; or aryl; and R.sub.8 is hydrogen or C.sub.1 -C.sub.6 alkyl or a C.sub.3 -C.sub.8 cycloaliphatic unsubstituted, or substituted with halo, C.sub.1 -C.sub.6 alkyl, alkoxy, hydroxy, or one of one or more hetero atoms; or aryl; and formula (III) ##STR3## wherein R.sub.9 is a C.sub.1 -C.sub.6 alkenyl and R.sub.10 is hydrogen or C.sub.1 -C.sub.6 alkyl; are used in compositions which, in the absence of the spiromonomers, normally undergo shrinkage, so that the resulting polymerizates exhibit substantially zero shrinkage or even slight positive expansion.

REFERENCES:
patent: 4387215 (1983-06-01), Bailey
patent: 4980109 (1990-12-01), Yamamoto et al.
H. Tagoshi and Ti Endo, Journal of Polymer Science: Part A: Polymer Chemiy 27, 1415-1418, 1989.
Jeffrey Wilson Stansbury, Dissertation Abstract for Ph.D., 1988.
J. W. Stansbury, J. Dent. Res. 71(7):1408-1412, Jul. 1992.
Jun-Ichi Sugiyama, Tsutomu Yokozawa, and Takeshi Endo Journal of Polymer Science: Part A: Polymer Chemistry, vol. 28, 3529-3532 (1990), John Wiley & Sons, Inc., "Preparation and Radical Polymerization of Spiroorthocarbonate Having 1,3-Dioxolane Skeleton".
Hirotaka Tagoshi and Takeshi Endo, Journal of Polymer Science: Part A: Polymer Chemistry, vol. 27, 1415-1418 (1989), John Wiley & Sons, Inc., "Radical Polymerization of Unsaturated Spiroorthocarbonate".
Dissertion of Jeffrey Wilson Stansbury, Ph.D., 1988, "Free Radical Ring-Opening Polymerization of Unsaturated, Asymmetric Spiro Orthocarbonates".
Journal of Polymer Science, Polymer Chemistry Ed. 20:1401-1409 (1982), Fukada et al., "Spontaneous Copolymerization of 4-Methylene-1,3-Dioxolanes with Maleic Anhydride".
Journal of Polymer Science, Polymer Chemistry Ed. 13:2525-2530 (1975), Endo et al., "Synthesis and Radical Ring-Opening Polymerization of Spiro-o-Carbonates".
Journal of Polymer Science, Part A, Polymer Chemistry, 27:1415-1418 (1989), Tagoshi et al., "Radical Polymerization of Unsaturated Spiroorthocarbonate".
J Dent Res 58(5):1522-1532, May 1979, Thompson et al., "Dental Resins with Reduced Shrinkage During Hardening".
ACS Polym. Prepr., vol. 31, No. 2, Aug. 1990, Washington, D.C., Wang et al., "Synthesis and Free Radical Ring-Opening Polymerization of 2-Alkyl-7-Methylene-1,4,6-Trioxapiro[4,4]Nonane".
J Dent Res 66(11):1636-1639, Nov. 1987, Feilzer et al., "Setting Stress in Composite Resin in Relation to Configuration of the Restoration".
Dent Mater 6:167-171, Jul. 1990, Feilzer et al., "Quantitative determination of stress reduction by flow in composite restorations".
Progress in Biomedical Polymers, Plenum Press, New York, 1990, Stansbury et al., "Evaluation of Spiro Orthocarbonate Monomers Capable of Polymerization with Expansion as Ingredients in Dental Composite Materials" pp. 133-139.
J Dent Res 66(3):716-721, Mar. 1987, Zidan et al., "A Comparative Study of the Effects of Dentinal Bonding Agents and Application Techniques on Marginal Caps in Class V Cavities".
J Dent Res 65:219 Abst. #452 (1986), Stansbury et al., "Synthesis of Monomers that Polymerize with Expansion in Volume".

Affiliated with

Also associated with

Rating

Monomers for double ring-opening polymerization with expansion does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Monomers for double ring-opening polymerization with expansion, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Monomers for double ring-opening polymerization with expansion will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-1784214