# US 8,785,513 B2 · Fiber-reinforced composites and method for the manufacture thereof

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- Number: US 8,785,513 B2
- Document ID: US8785513B2
- Status: Granted
- Kind: B2
- Application number: 12/306,673
- Filed: 2007-06-29
- Published: 2009-10-15
- Granted: 2014-07-22
- Earliest claimed: 2006-06-30
- Assignees: Stick Tech Oy
- Applicants: Lippo V. J. Lassila; Pekka K. Vallittu; Sufyan Garoushi; Karri Airola
- Inventors: Lippo V. J. Lassila; Pekka K. Vallittu; Sufyan Garoushi; Karri Airola
- Web page: https://patentgrep.com/patent/US8785513B2

## CPC

- A61K 6/30: Compositions for temporarily or permanently fixing teeth or palates, e.g. primers for dental adhesives
- A61K 6/50: Preparations specially adapted for dental root treatment
- A61K 6/54: Filling; Sealing
- A61K 6/887: Compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- A61K 6/891: Compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- A61L 27/46: with phosphorus-containing inorganic fillers
- A61L 27/48: with macromolecular fillers
- A61P 1/02: Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61L: METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES (preservation of bodies or disinfecting characterised by the agents employed A01N; preserving, e.g. sterilising, food or foodstuffs A23; preparations for medical, dental or toiletry purposes A61K)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

The present invention relates to fiber-reinforced composites, particularly application-oriented composites useful in dental and medical applications/appliances, such as fiber reinforced dental composites, and to a method for the manufacture thereof. Particularly the invention concerns random glass fiber-reinforced restorative composite resins with semi-interpenetrating polymer network matrix and their use in dental applications like cavity fillings, core composites, provisional and semi-permanent crown and bridge composite, cements and adhesives.

## Claims

### Claim 1

A curable fiber-reinforced composite for direct restoration, said composite comprising:
(a) 10-60 wt-% of a monomer system comprising at least one curable monomer selected from dimethacrylates, acrylates, methacylates, epoxides, dimethacrylates of polyethyleneglycols, and light curable biodegradable resins;
(b) 40-90 wt-% of a filler system comprising (i) at least one prepreg comprising highly viscous bundles of fibers, selected from the group consisting of fibers of bioactive glass, glass fibers, alumina fibers, zirconia fibers, metallic fibers, ceramic fibers, carbon/graphite fibers, polymeric fibers, self-reinforced polymer fibers, fibers based on polyphenols, degradable and biodegradable fibers, sol-gel derived silica fibers, and mixtures thereof, said fibers having fiber diameters of 0.05-100 μm and fiber lengths of 0.5-100 mm in a polymer matrix having a viscosity of at least 500 Pa·s, wherein the prepreg is in the form of pieces having a length of 3-20 mm, (ii) 0-80 wt-% of at least one particulate filler selected from conventional particulate fillers having a particle size of 0.1-100 μm and nanoscale particulate fillers having a particle size of less than 0.1 μm, and (iii) polymeric matrix; and
(c) a polymerization initiator(s) and/or a polymerization accelerator(s),
wherein said components (a), (b), and (c) are compounded together, thereby forming an application-orientated curable material which provides reduced polymerization shrinkage in direct composite restorations.

### Claim 2 (depends on 1)

The curable fiber-reinforced composite according to claim 1, characterized in that it comprises (a) 15-30 wt-% of the monomer system and (b) 70-85 wt-% of the filler system.

### Claim 3 (depends on 1)

The curable fiber-reinforced composite according to claim 1, characterized in that the curable monomers of the monomer system are selected from bisphenol A-glycidyl dimethacrylate, bisphenol A polyethyleneglycol diether, triethyleneglycol dimethacrylate, tetraethyleneglycol dimethacrylate, neopentylglycol dimethacrylate, hydroxyethyl methacrylate, methyl methacrylate and acrylate, urethane dimethacrylate, 1,3- and 1,4-butanediol dimethacrylate, 1,6-hexanediol dimethacrylate, methylmethacrylate and 2-hydroxyethanol methacrylate.

### Claim 4 (depends on 1)

The curable fiber-reinforced composite according to claim 1, characterized in that the conventional particulate filler is selected from color pigments, inert ceramics, xerogels, inorganic salts, bioactive or bio-soluble glasses and combinations thereof and the nanoscale particulate fillers are selected from inorganic fillers, organic polymer fillers and organic-inorganic silsesquioxane based fillers.

### Claim 5 (depends on 1)

The curable fiber-reinforced composite according to claim 1, characterized in that the conventional particulate filler is selected from phosphates and oxides of Si, Ba, AL, Ca, P, Ba, Zr, Al, Mg, K, Na, and Ti.

### Claim 6 (depends on 1)

A dental or medical composition comprising the curable fiber-reinforced composite according to claim 1.

### Claim 7 (depends on 6)

The dental or medical composition use according to claim 6, wherein the dental composition is a component of a restorative prosthodontic material, a core composite, an adhesive, a liner, a cementing and luting material, a cavity filling material, a root canal post-cementing material, a provisional and semi-permanent crown and bridge composite material or a CAD/CAM block, and the medical composition is a component of an orthopedic bone cement, a bone support device for maxillofacial, head and neck surgery or an implant.

### Claim 8 (depends on 1)

The curable fiber-reinforced composite according to claim 1, characterized in that the conventional particulate filler is selected from fumed silica, colloidal silica, amorphous silica, quartz, alumina silicate, barium silicate glass, fluorosilicate glass, zirconia, calcium oxides, hydroxyapatites, titania, and calcium phosphate.

### Claim 9 (depends on 1)

The curable fiber-reinforced composite according to claim 1, characterized in that the fibers are selected from fibers having a diameter of 1-25 μm.