Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Polymers from only ethylenic monomers or processes of...
Patent
1997-04-10
2000-03-21
Lipman, Bernard
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
Polymers from only ethylenic monomers or processes of...
524560, 524561, 524562, C08F 1800
Patent
active
060404086
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to a class of polymeric materials exhibiting radiopacity due to the fact that molecules containing covalently-bound iodine were built-in during polymerisation. Fields of application of such radiopaque polymers include, but are not limited to: medical materials (e.g. bone cements, catheters, and implants such as blood vessel prostheses and endovascular stents); veterinary materials (e.g. implants, catheters), and toys, especially small objects with the associated danger of being swallowed. Due to the presence of covalently bound iodine in the polymer post-operative assessment of the fate of implants, using X-ray scanning, is possible.
In the literature some experiments have been described, dealing with the polymerization of iodine containing monomers. These experiments did not result in any suitable materials, as the polymerization did not proceed to a sufficient high molecular weight, or the resulting material did possess hemolytic properties, which makes the material unsuitable for biomedical applications,
The present invention relates to a class of radiopaque biomedical polymeric materials having a number average molecular weight of at least 7500. These radiopaque materials are either: (i) polymers of a monomer molecule that contains covalently-bound iodine, or (ii) copolymers in which at least one of the different monomers contains covalently-bound iodine, or (iii) terpolymers or polymers of even higher complexity, in which at least one of the different monomers contains covalently-linked iodine.
This group of polymers encompasses a wide variety of materials since a virtually unlimited variation is possible for iodine containing monomers. Furthermore, the composition of copolymers, terpolymers, and other polymers such as mentioned under (ii) and (iii) can be varied, both in terms of relative concentration, and in terms of molecular structure of the different constituents.
Radiopaque polymers according to this invention are clearly distinguished with respect to prior art ("Preparation and evaluation of radiopaque hydrogel microspheres based on pHEMA/iothalamic acid and pHEMA/iopanoic acid as particulate emboli" A. Jayakrishnan et al., Journal of Biomedical Materials Research, 24, 993-1004 (1990); "Synthesis and polymerization of some piodpine-containing monomers for biomedical applications" A. Jayakrishnan et al., Journal of Applied Polymer Science 44, 743-748 (1992)) in which it was reported that only low-molecular-weight products are obtained when acrylic derivatives of triiodophenyl or iodothalamic acidare copolymerised with methyl methacrylate (MMA) or 2-hydroxyethyl methacrylate (HEMA).
The invention is explained in detail in the following: Although radiopaque polymers of different structural types are subject to this invention, the most predominant ones are polyacrylates and derivatives thereof. Preparation of radiopaque polyacrylates starts with synthesis of a monomer in which iodine is covalently bound. Molecules of this type include, but are not limited to the group of structures represented in Scheme I, which is divided into three subgroups (a, b, and c). ##STR1## subgroup a.: iodine in group R'. R.dbd.H, CH.sub.3, C.sub.2 H.sub.5, or another organic substituent. H.sub.2 I.sub.3, NH--C.sub.6 H.sub.4 I, NH--C.sub.6 H.sub.3 I.sub.2, NH--C.sub.6 H.sub.2 I.sub.3, O--CH.sub.2 --CH.sub.2 --C(O)--C.sub.6 H.sub.4 I, O--CH.sub.2 --CH.sub.2 --O--C(O)--C.sub.6 H.sub.3 I.sub.2, O--CH.sub.2 --CH.sub.2 --O--C(O)--C.sub.6 H.sub.2 I.sub.3, NH--CH.sub.2 --CH.sub.2 --C(O)--C.sub.6 H.sub.4 I, NH--CH.sub.2 --CH.sub.2 --O--C(O)--C.sub.6 H.sub.3 I.sub.2, NH--CH.sub.2 --CH.sub.2 --O--C(O)--C.sub.6 H.sub.2 I.sub.3,or another organic iodine-containing substituent. iodine-containing substituent. O--C.sub.n H.sub.2n+1, or other organic groups. double bond and one or more covalently linked iodine atoms are present in the structure.
The first method of preparation of monomers in subgroup a. of Scheme I starts our with an acylic acid chloride., e.g. methacryloyl chloride. These reactive compoun
REFERENCES:
patent: 4644025 (1987-02-01), Sakagami et al.
patent: 4822721 (1989-04-01), Tsutsumi et al.
patent: 4997894 (1991-03-01), Telgarden
patent: 5271923 (1993-12-01), Kochi et al.
Answer 4 of 15, 1995:249908, Benzira et al "Strokes on a new radiopaque polymer biomaterial" Biomaterials, 15(14), 1122-8(English) 1994--in house abstract pp. 9-10.
Answer 5 of 15, 1995:132324, Dary et al "Novel aromatic dime thacrylate esters of dental resins" Mater. Med., 5(607), 350-2 (English) 1994--in house abstract pp. 10-11.
Answer 6 of 15 1994:708210, Kruft et al, "Two new radiopaque polymeric biomaterials" J. Biomed. Mater. Res., 28(11), 1259-66(English)1994--in house abstract pp. 11-13.
Answer 11 of 15, 1989:515854, Suzuki et al. Polym. Bull. (Berlin), 21(4), 415-20 (English) 1989. In house abstract pp. 21-24.
Hackh's Chemical Dictionary--May 27, 1981 p. 570.
Biomat B.V.
Lipman Bernard
LandOfFree
Radiopaque polymers and methods for preparation 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 Radiopaque polymers and methods for preparation thereof, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Radiopaque polymers and methods for preparation thereof will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-731274