US20060035997A1 - Curable acrylate polymer compositions featuring improved flexural characteristics - Google Patents

Curable acrylate polymer compositions featuring improved flexural characteristics Download PDF

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Publication number
US20060035997A1
US20060035997A1 US10/914,972 US91497204A US2006035997A1 US 20060035997 A1 US20060035997 A1 US 20060035997A1 US 91497204 A US91497204 A US 91497204A US 2006035997 A1 US2006035997 A1 US 2006035997A1
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composition
acrylic monomers
methacrylate
weight
monomers
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US10/914,972
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Jan Orlowski
David Butler
Alice Chin
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Scientific Pharmaceuticals Inc
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Scientific Pharmaceuticals Inc
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Priority to US10/914,972 priority Critical patent/US20060035997A1/en
Assigned to SCIENTIFIC PHARMACEUTICALS, INC. reassignment SCIENTIFIC PHARMACEUTICALS, INC. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: BUTLER, DAVID V., CHIN, ALICE, ORLOWSKI, JAN A.
Priority to GB0515911A priority patent/GB2427864B/en
Priority to DE102005036637.6A priority patent/DE102005036637B4/de
Priority to JP2005229259A priority patent/JP4344946B2/ja
Publication of US20060035997A1 publication Critical patent/US20060035997A1/en
Priority to US12/476,918 priority patent/US20090239969A1/en
Priority to US13/941,370 priority patent/US9028254B2/en
Abandoned legal-status Critical Current

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K6/00—Preparations for dentistry
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K6/00—Preparations for dentistry
    • A61K6/80—Preparations for artificial teeth, for filling teeth or for capping teeth
    • A61K6/884—Preparations for artificial teeth, for filling teeth or for capping teeth comprising natural or synthetic resins
    • A61K6/891—Compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • A61K6/893—Polyurethanes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61C—DENTISTRY; APPARATUS OR METHODS FOR ORAL OR DENTAL HYGIENE
    • A61C19/00—Dental auxiliary appliances
    • A61C19/003—Apparatus for curing resins by radiation
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K6/00—Preparations for dentistry
    • A61K6/20—Protective coatings for natural or artificial teeth, e.g. sealings, dye coatings or varnish
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K6/00—Preparations for dentistry
    • A61K6/30—Compositions for temporarily or permanently fixing teeth or palates, e.g. primers for dental adhesives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K6/00—Preparations for dentistry
    • A61K6/80—Preparations for artificial teeth, for filling teeth or for capping teeth
    • A61K6/884—Preparations for artificial teeth, for filling teeth or for capping teeth comprising natural or synthetic resins
    • A61K6/887—Compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • 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
    • A61L24/00—Surgical adhesives or cements; Adhesives for colostomy devices
    • A61L24/04—Surgical adhesives or cements; Adhesives for colostomy devices containing macromolecular materials
    • A61L24/046—Surgical adhesives or cements; Adhesives for colostomy devices containing macromolecular materials obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
    • C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
    • C08F20/10—Esters
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
    • C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
    • C08F20/10—Esters
    • C08F20/12—Esters of monohydric alcohols or phenols
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F22/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides or nitriles thereof
    • C08F22/10—Esters
    • C08F22/12—Esters of phenols or saturated alcohols
    • C08F22/14—Esters having no free carboxylic acid groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
    • C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
    • C08L23/26—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers modified by chemical after-treatment
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/04—Homopolymers or copolymers of esters
    • C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
    • C08L33/10—Homopolymers or copolymers of methacrylic acid esters
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L35/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical, and containing at least one other carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L35/02—Homopolymers or copolymers of esters
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L9/00—Compositions of homopolymers or copolymers of conjugated diene hydrocarbons

Definitions

  • This invention relates to modified, acrylate polymer compositions featuring reduced brittleness, such polymers being particularly suitable as dental/medical cements and restorative materials and for manufacturing dental prosthetics.
  • acrylic resins due to a variety of available monomers, usually make it possible to compound a blend which, upon cure, will result in a polymer meeting the requirements of tissue biocompatibility, wear resistance, translucency, mechanical strength or hardness, they frequently fail or are less than satisfactory in applications requiring flexibility. It is especially true in situations where thin layers of polymers are exposed to flexural forces; for example, while placing or removing a well-fitted device. Another example of situations where the greater flexibility and impact resistance of acrylic polymers would be highly desirable are applications where the devices made of such polymeric materials are exposed to rapid or repetitiously applied forces. Especially vulnerable are thin areas of such objects.
  • cross-linked acrylic polymers are generally preferred over the linear ones. Consequently, in addition to monounsaturated monomers frequently used in such applications, exemplified by alkylmethacrylates, tetrahydrofurfuryl methacrylate and hydroxyalkyl methacrylates, di-, tri- or even higher polymethacrylates are employed.
  • Such polyfunctional monomers may be used in blends with monofunctionals serving as cross-linking agents, or in compositions where monofunctional monomers are absent.
  • Acrylic resins have unique features making them difficult to replace with other types of monomers, especially in particular or very demanding applications. These include ease of control of working and curing times, good biocompatibility, and a broad selection of available monomers, and relative ease of synthesizing new ones, having desirable molecular structures allows for modifying or controlling relevant characteristics of cured polymers such as water absorption, solubility, hydrophobicity, adhesive properties, compatibility with various additives, optical properties, mechanical strength, chemical resistance and resistance to heat and UV light. These properties allow for multiple ways of inducing polymerization, such as by chemical means, heat, or light.
  • compositions according to preferred embodiments in which olefinic polymers are used as additives to acrylic polymers, provide more flexible and impact-resistant acrylate polymers suitable for a variety of uses, particularly those related to medical and dental fields.
  • Preferred compositions also effectively address the reducing or eliminating of the oxygen-inhibited layer and/or reducing the exothermic effect of the polymerization process.
  • Another advantage of polymers in accordance with preferred embodiments, particularly important in medical and dental applications, is their general lack of toxicity as well as a low incidence or absence of allergenic reaction and tissue irritation.
  • a curable composition comprising about 10-90% by weight of one or more acrylic monomers; and about 1-60% by weight of an olefinic component comprising oligomers or polymers of one or more straight chain or branched C4-C6 monomers having one or two double bonds per monomer molecule.
  • the compositions may further comprise one or more additives selected from the group consisting of polymerization initiators, polymerization activators, stabilizers, UV light absorbers, colorants, fillers, therapeutic agents, flavoring agents and viscosity/rheological modifiers.
  • the compositions may exist as one part or component, or they may be in two parts that are mixed together prior to use.
  • the composition may be used in medical and/or dental applications as a medical device such as a restorative material, prosthesis, cement, cavity liner, varnish or sealer.
  • a method of performing a dental procedure comprising obtaining a curable composition comprising 10-90% by weight of one or more acrylic monomers and 1-60% by weight of an olefinic component comprising oligomers or polymers of one or more straight chain or branched C4-C6 monomers having one or two double bonds per monomer molecule; applying the composition to at least one surface of a tooth or dental appliance; and allowing the composition to cure.
  • the technology disclosed herein relates to heat, chemically (i.e. self-curable) or light (UV and/or visible) curable acrylate acrylic resin-based formulations as well as polymers or objects resulting from curing of such formulations.
  • acrylic resins have the numerous possible advantages noted above, certain intrinsic characteristics of acrylic resins have limited their scope of application or have complicated their handling or reliability. Such characteristics include brittleness of cured polymers, oxygen-inhibited thin liquid layer remaining on the surface of the cured polymer that leaves a dull surface after being wiped off, and high exothermicity accompanying the polymerization process. Although the high exothermicity is observed primarily during rapid polymerization of unfilled or low-filled lower molecular weight acrylate monomers, such compositions and requirements of fast cure are considered highly desirable in certain clinical applications. Examples of applications raising concern with regard to exothermic effects generated during cure of acrylic monomers include cured or cemented in situ medical and dental devices such as hip prostheses, dental fissure sealers, temporary or permanent crowns and bridges and cemented orthodontic appliances.
  • a third attempt was to use inorganic particulate fillers, however, the cured material was brittle and very hard; although the exothermic effect of polymerization and oxygen-inhibited layer were significantly reduced.
  • Another attempt was to add phthalic acid esters and other polymers flexibilizing additives. It was found that such additives, although efficient when incorporated in other type polymers, were of little use in acrylic resin. In addition, concerns were raised about their safety when employed in dental/medical materials.
  • compositions and objects made of such compositions are modified, chemically-, heat- or light-curable acrylate compositions and objects made of such compositions.
  • temporary flexibility is herein defined as transient flexural characteristics of the material during a defined time, usually 1-5 minutes after initial cure.
  • Such materials also generally exhibit significant improvement over unmodified acrylic polymers in their resistance to breaking under stress.
  • oxygen-inhibited layer after polymerization is virtually or entirely eliminated and, if desired, so is the exothermic effect generated during the curing process of the formulations of this invention.
  • compositions and objects made of such compositions comprise:
  • polymers or oligomers of olefinic monomers having four to six carbon atoms and one or two double bonds per molecule such polymers preferably having molecular weight of 300-2500 and viscosity of 25-4500 cp.
  • ranges for components such as those above mean that if there is one recited component, it is present at a concentration within the stated range (as compared to the weight of the entire composition) and if there are two or more species of the recited component present, the total combined weight of all such species will fall within the stated range. Within the range is to be read as inclusive of the upper and lower limits.
  • the composition optionally comprises one or more of one or more of the following compounds and/or materials: polymerization activating agents, UV absorbers, stabilizers for preventing premature polymerization, organic and/or inorganic fillers, colorants, such as pigments and/or dyes (for aesthetic, diagnostic or use-facilitating purposes), and other desirable additives to enhance mechanical or visual/optical properties of the material.
  • Polymerization activators include, but are not limited to, amines, preferably tertiary amines, and/or peroxides.
  • Preferred polymerization activators include, but are not limited to, benzoyl peroxide, halogen substituted derivatives of benzoyl peroxide, N,N bis-(2-hydroxyethyl) p-toluidine, N,N diethyl-p-toluidine, camphoroquinone, tertiary aliphatic amines, trialkylamines, methacroylalkyl-dialkylamines, and combinations of the foregoing. If present, the one or more polymerization activators are preferably present at concentrations of about 0.5-2% by weight.
  • Stabilizers include, but are not limited to BHT, and, if stabilizers are present, they are preferably present at about 0.01-0.1% by weight, or in sufficient quantity to prevent premature polymerization of the material during storage and/or transport.
  • Preferred fillers include glass, silica (amorphous and/or fumed), quartz silica, aluminum oxide, zirconium oxide, barium sulfate, and mixtures thereof. If present, fillers preferably comprise about 10%-30% of the composition by weight, including about 15%-25%.
  • the composition may be produced and stored as a single part or it may be as two or more parts, each of which has some or all of the component chemicals and materials of the composition.
  • the two (or more) parts are mixed prior to application or use.
  • Two or more part formulations are preferred for those formulations of the composition which self-cure or chemically cure.
  • the constitution of the composition and the amounts of the component parts refer to the composition following mixing, i.e. the composition as it is used.
  • the individual parts may comprise varying amounts of materials and may be mixed in any proportion such as from 1:20 (v/v) to 20:1 (v/v), provided that the final composition is according to the description herein.
  • the two parts (Part A and Part B) are mixed in a 1:1 (v/v) ratio by hand or static mixer.
  • compositions came as a total surprise, as polyolefins were known only as modifiers of thermoplastic polymers and elastomers, and not for thermosetting polymers, to which category acrylate polymers belong. Furthermore, it was surprising to find that such olefinic polymers are compatible with a large variety of acrylate monomers and/or their blends, and are useful in a broad range of their molecular weights.
  • Blends comprising olefinic polymers or oligomers, preferably liquid polymers having molecular weights in the range of approximately 100-700, and aliphatic or aromatic acrylate monomers were found to be particularly advantageous in certain aspects.
  • methacrylic acid esters are preferred over acrylic acid ones.
  • the acrylate component of preferred compositions preferably comprises about 10-90% by weight of an acrylic monomer or a blend of acrylic monomers, including about 50-80%, about 60-80%, about 50-70%, about 60-80%, about 70-80%, and about 50-60% by weight.
  • a composition comprising a monomer may be purely monomers, or it may contain some or all of dimers, trimers or other oligomers.
  • the acryate component comprises esters of acrylic or methacrylic acid containing one or more acrylate or methacrylate moieties per molecule.
  • acrylate monomers suitable for use in formulations of this invention include, but are not limited to: ethylene and propylene glycol dimethacrylates, di-, tri- and polyethylene and propylene glycol dimethacrylates (including, but not limited to, di-polyethylene glycol dimethacrylate, tri-polyethylene glycol dimethacrylate, di-propylene glycol dimethacrylate, and tri-propylene glycol dimethacrylate), tri-methylolopropane trimethacrylate, hydroxyethyl methacrylate, hydroxypropyl methacrylate, tetrahydrofurfuryl methacrylate, 1,6-hexanediol dimethacrylate 7,7,9-trimethyl-4,13-dioxo-3,14-dioxa- -5,12-diazahexadecane-1,16-diol dimethacrylate (commonly known as diurethane dimethacrylate), 2,2-
  • aliphatic monomethacrylate monomers preferably in mixtures with di- or poly-dimethacrylates is desirable: C 1 -C 12 alkyl methacrylates, cyclohexyl methacrylate, hydroxy-(C 2 -C 4 ) alkyl methacrylates and glycerol methacrylates.
  • the olefinic component of preferred compositions preferably comprise about 1-60% by weight of polymers or oligomers of olefinic monomers having four to six carbon atoms, including about 1-10%, about 1-20%, about 10-20%, about 10-30%, about 1-40%, and about 10-40% by weight.
  • suitable olefinic polymers or oligomers include various olefinic polymers or oligomers derived from C 4 -C 6 mono- or bi-unsaturated monomers, preferably those originated or derived from monomers having four carbon atoms in their lineal chain such as butene, butadiene or methyl butadiene (isoprene). In most applications polybutene is preferred, being inexpensive and commercially available in a desirable range of molecular weights.
  • compositions disclosed herein may be formed or molded into medical devices or used as a cement in a medical application, such as a bone cement in orthopedic surgical procedures.
  • the materials may also be molded or formed to create a prosthesis or dental restorative, or it may be applied to a tooth and/or a dental appliance (including but not limited to crowns, bridges, whether permanent or temporary), thereby being used as a cement, cavity liner, varnish, sealer, veneer or a “bonding” material to fill in dental imperfections or a missing portion of a tooth.
  • a method of performing a dental procedure comprising obtaining a curable composition as disclosed herein in various embodiments; applying the composition to at least one surface of a tooth or dental appliance; and allowing the composition to cure.
  • this disclosure also includes the use of a curable composition as disclosed herein as a cement, cavity liner, varnish, sealer, veneer, bonding material, prosthesis or dental restorative in the treatment of a diseased tooth (such as a tooth having a cavity or decay (caries)), broken tooth, or discolored tooth.
  • a heat curable composition consisted of: % (by weight) Diurethane dimethacrylate 73.58 Polybutene 9.68 BHT 0.05 Benzoyl peroxide 1.06 Silica 15.63
  • the components were mixed and the material composition was cured in the oven at 100° C. for 1 hour.
  • the properties of cured material are: Barcol hardness: 25-30; Flexural strength: 71 Mpa.
  • the product was judged suitable for intended use, such as for a temporary crown and bridge material.
  • a light curable composition consisted of: % (by weight) Diurethane dimethacrylate 73.75 Polybutene 8.38 Camphoroquinone 0.26 Methacroyl ethyl diethylamine 0.75 Silica 16.86
  • the material was mixed and then cured for 20 seconds using an Optilux® dental curing device (light curing). The product was judged suitable for intended use.
  • a chemically curable composition consisted of a 1:1 (v/v) mixture of Parts A and B: % (by weight) Part A Diurethane dimethacrylate 78.96 N,N bis(2-hydroxyethyl)-p-toluidine 0.39 Silica 20.65 Part B Diurethane dimethacrylate 73.58 Polybutene 9.68 BHT 0.05 Benzoyl peroxide 1.06 Silica 15.63
  • the material was soft cured in 110 seconds and hard cured in 150 seconds at 23° C. (soft cure is defined as a stage at which the material becomes solid but exhibits flexibility).
  • the properties of cured material are: Barcol hardness: 42-45; Flexural strength: 61 Mpa. The product was judged suitable for use.
  • a self curable composition consisted of a 1:1 (v/v) mixture of Parts A and B: % (by weight) Part A EBA 17.29 Triethylene glycol dimethacrylate 20.47 Bis-GMA 14.09 Polybutene 30.18 BHT 0.01 N,N bis(2-hydroxyethyl)-p-toluidine 1.87 Silica 16.09 Part B EBA 18.61 Triethylene glycol dimethacrylate 21.7 Bis-GMA 14.88 Polybutene 16.28 BHT 0.08 Benzoyl peroxide 0.77 Silica 27.68
  • the material reached soft curing stage in 175 seconds and hard cured in 210 seconds at 23° C.
  • the product was judged suitable for use, but was somewhat inferior to the product of Example 3.
  • the cured material had similar properties to that of Example 3.
  • the material reached soft curing stage in 85 seconds and hard cured in 140 seconds at 23° C. The product was judged suitable for use.
  • the properties of cured material are: Barcol hardness: 50-55; Flexural strength: 83 Mpa. The cured product was judged not suitable as a temporary crown and bridge material because of lack of flexibility.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • Plastic & Reconstructive Surgery (AREA)
  • General Chemical & Material Sciences (AREA)
  • Surgery (AREA)
  • Dentistry (AREA)
  • Dental Preparations (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Graft Or Block Polymers (AREA)
US10/914,972 2004-08-10 2004-08-10 Curable acrylate polymer compositions featuring improved flexural characteristics Abandoned US20060035997A1 (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
US10/914,972 US20060035997A1 (en) 2004-08-10 2004-08-10 Curable acrylate polymer compositions featuring improved flexural characteristics
GB0515911A GB2427864B (en) 2004-08-10 2005-08-02 Curable acrylate polymer compositions featuring improved flexural characteristics
DE102005036637.6A DE102005036637B4 (de) 2004-08-10 2005-08-04 Härtbare Acrylat-Polymer-Zusammmensetzung mit verbesserten Biegungseigenschaften sowie deren Verwendung
JP2005229259A JP4344946B2 (ja) 2004-08-10 2005-08-08 改良された曲げ特性を特徴とする硬化性アクリレートポリマー組成物
US12/476,918 US20090239969A1 (en) 2004-08-10 2009-06-02 Dental prosthetics comprising curable acrylate polymer compositions and methods of their use
US13/941,370 US9028254B2 (en) 2004-08-10 2013-07-12 Dental prosthetics comprising curable acrylate polymer compositions and methods of their use

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US12/476,918 Abandoned US20090239969A1 (en) 2004-08-10 2009-06-02 Dental prosthetics comprising curable acrylate polymer compositions and methods of their use
US13/941,370 Expired - Lifetime US9028254B2 (en) 2004-08-10 2013-07-12 Dental prosthetics comprising curable acrylate polymer compositions and methods of their use

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US13/941,370 Expired - Lifetime US9028254B2 (en) 2004-08-10 2013-07-12 Dental prosthetics comprising curable acrylate polymer compositions and methods of their use

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Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20050070915A1 (en) * 2003-09-26 2005-03-31 Depuy Spine, Inc. Device for delivering viscous material
US20060079905A1 (en) * 2003-06-17 2006-04-13 Disc-O-Tech Medical Technologies Ltd. Methods, materials and apparatus for treating bone and other tissue
US20060264967A1 (en) * 2003-03-14 2006-11-23 Ferreyro Roque H Hydraulic device for the injection of bone cement in percutaneous vertebroplasty
US20070027230A1 (en) * 2004-03-21 2007-02-01 Disc-O-Tech Medical Technologies Ltd. Methods, materials, and apparatus for treating bone and other tissue
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US20130302513A1 (en) 2013-11-14
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US9028254B2 (en) 2015-05-12

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