Dental compositions comprising bisacrylamides and use thereof

Details Dental compositions comprising bisacrylamides and use thereof Dental compositions comprising bisacrylamides and use thereof

2002-12-03

2004-07-27

Yoon, Tae H. (Department: 1714)

Synthetic resins or natural rubbers -- part of the class 520 ser

Synthetic resins

Processes of preparing a desired or intentional composition...

C523S109000, C523S113000, C523S115000, C523S116000, C523S118000, C522S047000, C524S323000

Reexamination Certificate

active

06767936

ABSTRACT:

TECHNICAL BACKGROUND
Since decades the free-radical polymerization used in electrotechnics, electronics, dental industry, is combined with remarkable advantages in these fields. The frequently used acrylates and methacrylates are applied in combination with pigments and fillers or as pure polymerizable resins. It is well-known that during free-radical polymerization some side-reactions take place. One of them is the inhibition of the outer layer of the polymerizable material due to the influence of oxygen. The thickness of this layer depends on the viscosity of the polymerizable material, the degree of filling, the applied temperature and the time of polymerization. Frequently, the oxygen inhibited layer is disadvantageous due to the mechanical properties in this part are insufficient, the abrasion is higher and the toxicological/allergic potential is increased. The polymerization of very small layers is limited due to the oxygen inhibition, for example in case of covering electronic circuits by screen printing or for dental sealing materials or varnishes.
Furthermore, the conventional methacrylates that were used for dental applications are ester compound. Consequently, they hydrolysis under acidic or basic conditions that frequently leads to a long-term failure.
In order to reduce the oxygen inhibited layer different possibilities were suggested. One of them is the today well-known use of carbonyl/amine initiator systems for photochemical polymerization (R. S. Davison, J. W. Goodin, Eur.Polym.J 18 (1982) 597). Dekker used special color initiators that change triplet-oxygen into singulet-oxygen (C. Dekker, Makromol. Chem. 180 (1979) 2027). Furthermore, surface active additives were used (C. R. Morgan, A. D. Ketley, J. Radiat.Curing 7 (1980) 10) or the photochemical SH-En-Addition was applied (C. R. Morgan, F. Magnotta, A. D. Ketley, J.Polym.Sci., Polym. Ed. 15 (1977), 627).
The photochemical polymerization of monoacrylamides was studied by Smets (G. Smets, Bull.Soc.Chim.Belges 71 (1962) 857, G. Oster, J.Amer.Chem.Soc. 79 (1957) 595). A large number of bisacrylamides were described by Ferrutti (P. Ferrutti et al., Polymer 26 (1985) 1336). These bisacrylamides are solids that are soluble in water due to the secondary amide group or they comprises a piperidine group.
A combination of free-radical and Michael addition polymerization was suggest for encapsulation of electronic circuits (DD 295645; invs.: J. Klee, H.-H. Hörhold, I. Scherlitz-Hofmann).
The new synthesized bisacrylamides should be liquids in order to polymerized them without of solvents and furthermore they and the resulting polymers should be insoluble in water.


REFERENCES:
patent: 3787213 (1974-01-01), Gervay et al.
patent: 3997504 (1976-12-01), Plymale
patent: 4089763 (1978-05-01), Dart et al.
patent: 4297266 (1981-10-01), Ibsen et al.
patent: 4323348 (1982-04-01), Schmitz-Josten et al.
patent: 4386912 (1983-06-01), Nagase et al.
patent: 4457818 (1984-07-01), Denyer et al.
patent: 4525256 (1985-06-01), Martin
patent: 4558120 (1985-12-01), Tomalia et al.
patent: 4587329 (1986-05-01), Tomalia et al.
patent: 4674980 (1987-06-01), Ibsen et al.
patent: 4746686 (1988-05-01), Waller
patent: 4857599 (1989-08-01), Tomalia et al.
patent: 4952241 (1990-08-01), Reiners et al.
patent: 5274064 (1993-12-01), Sarkar
patent: 5308886 (1994-05-01), Masuhara et al.
patent: 5395883 (1995-03-01), Yates, III et al.
patent: 5418301 (1995-05-01), Hult et al.
patent: 5468789 (1995-11-01), Lewis et al.
patent: 5486548 (1996-01-01), Podszun et al.
patent: 5530092 (1996-06-01), Meijer et al.
patent: 5545676 (1996-08-01), Palazzotto et al.
patent: 5624976 (1997-04-01), Klee
patent: 5679794 (1997-10-01), Suhadolnik et al.
patent: 5709548 (1998-01-01), Oxman et al.
patent: 5767170 (1998-06-01), Ibsen et al.
patent: 5814681 (1998-09-01), Hino et al.
patent: 5834118 (1998-11-01), Ranby et al.
patent: 5847020 (1998-12-01), Ibsen et al.
patent: 5847025 (1998-12-01), Moszner et al.
patent: 5886064 (1999-03-01), Rheinberger et al.
patent: 5914379 (1999-06-01), Sutoris et al.
patent: 5969000 (1999-10-01), Yang et al.
patent: 5985958 (1999-11-01), Moszner et al.
patent: 6025114 (2000-02-01), Popat et al.
patent: 6030606 (2000-02-01), Holmes
patent: 6031016 (2000-02-01), Ibsen et al.
patent: 6121344 (2000-09-01), Angeletakis et al.
patent: 6136885 (2000-10-01), Rusin et al.
patent: 6184339 (2001-02-01), Stansbury et al.
patent: 22 11 128 (1973-09-01), None
patent: 3 703 080 (1988-01-01), None
patent: 3 703 120 (1988-01-01), None
patent: 295 645 (1990-07-01), None
patent: 023 686 (1980-07-01), None
patent: 049 599 (1981-09-01), None
patent: 059 649 (1982-03-01), None
patent: 102 199 (1983-08-01), None
patent: 140 140 (1984-09-01), None
patent: 254 950 (1987-07-01), None
patent: 630 640 (1994-12-01), None
patent: 673 637 (1995-09-01), None
patent: 765 856 (1995-09-01), None
patent: 716 103 (1995-11-01), None
patent: 995 421 (1999-10-01), None
patent: 334 845 (1984-01-01), None
patent: 92/21314 (1992-12-01), None
patent: 93/10176 (1993-05-01), None
patent: 93/12759 (1993-07-01), None
patent: 96/07688 (1996-03-01), None
patent: 97/02328 (1997-01-01), None
patent: 97/47272 (1997-12-01), None
Standish et al; “Cure of Resin Based Restorative Materials; I. Self Cure Resins”; Australian Dental Journal; Apr. 1983; vol. 28; No. 2; pp. 82-86.
Cook et al; “Cure of Resin Based Restorative Materials; II. White Light Photopolymerizable Resins”; Australian Dental Journal; Oct. 1983; vol. 28; No. 5;. pp. 307-311.
Standish et al; “Polymerization Kinetics of Resin-Based Restorative Materials”; Journal of Biomedical Materials Research; vol. 17, pp. 275-282 (1983).
Liso et al; “Analysis of the Leaching and Toxicity of New Amine Activators for the Curing of Acrylic Bone Cements and Composites”; Biomaterials 18 (1997) pp. 15-20; 1996 Elsevier Science Limited.
Kannurpatti et al; “Polymerization Behavior and Properties of Networks Formed by Dimethacrylate Dental Resins”; Division of Polymer Chemistry, Inc.; American Chemical Society; vol. 38; No. 2; Sep. 1997; pp. 106-107.
Cook et al; “A Simple Method for the Measurement of Polumerixation Shrinkage Dental Composites” Dental Materials 15 (1999); pp. 447-449.
NCBI National Liberty of Medicine; Br J Nutr 1998 Aug; 80 Suppl 1; S77-112; “Functional Food Science and Defence Against Reactive Oxidative Species”; 2 pgs.
NCBI National Library of Medicine; Crit Rev Food Sci Nutr 1994; 34(5-6): 47-97; “Antioxidants and Hormone-Mediated Health Benefits of Whole Grains”; 1 page.
NCBI National Liberty of Medicine; Santorro; Effect of Filler Content on the Profile of Released Biodegradation Products in Micro-Filled bis-GMA/TEGDMA Dental Composite Resins; Biomaterials Oct. 1999; 20(20); 1897-908; 1 pg.
NCBI National Library of Medicine; Crit Rev Oral Biol Med 1996; 7(2): 172-9; Bioavailability of Components of Resin-Based Materials Which are Applied to Teeth; 1 pg.
R.S. Davidson, J.W. Goodin, Eur. Polym. J. 18 (1982) pp. 597-606.
C. Dekker, Makromol. Chem. 180 (1979) pp. 2027-2030.
C.R. Morgan, A.D. Ketley, J. Radiat.Curing 7 (1980) pp. 10-13.
C.R. Morgan, F. Magnotta, A.D. Ketley, J. Polym. Sci., Polym. Ed. 15 (1977) pp. 627-645.
G. Smets, Bull. Soc. Chim. Belges 71 (1962) pp. 857-858.
G. Oster, J. Amer. Chem. Soc. 79 (1957) pp. 595-598.
P. Ferruti et al., Polymer 26 (1985) pp. 1336-1348.
H.G. Elais, Makromolekule, Huttig & Wepf, Basel 1990, p. 555.
Do Thi Bich Loan, I.m. Panayotov, Eur. Polym. J. 32 (1996) pp. 957-962.
Japanese Patent Abstract; vol. 010, No. 262 (c-371) Sep. 6, 1986.
Ferruti P. et al; “Recent Results on Functional Polymers and Macromonomers of Interestas Biomaterials or for Biomaterial Modification”.
Hill I. R. C. et al; “In vitro cytotoxicity of poly (amidoamine)s: relevance to DNA delivery” BBA-General Subjects, Elsevier Science Publishers, NL, vol. 1427, No. 2; Apr. 19, 1999, pp. 161-174.
Huang, et al; “The biocompatibility evaluation of epoxy resin-based root canal sealers in vitro”; Biomaterials, Elsevier Science Publishers BV., Barking, GB; vol. 23, No. 1, Jan. 1, 2002, pp. 77-83, XP004322622.

Affiliated with

Also associated with

Rating

Dental compositions comprising bisacrylamides and use 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 Dental compositions comprising bisacrylamides and use thereof, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Dental compositions comprising bisacrylamides and use thereof will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-3234649