CA2327730A1 - Synthesis of poly(propylene fumarate) by acylation of propylene glycol in the presence of a proton scavenger - Google Patents
Synthesis of poly(propylene fumarate) by acylation of propylene glycol in the presence of a proton scavenger Download PDFInfo
- Publication number
- CA2327730A1 CA2327730A1 CA002327730A CA2327730A CA2327730A1 CA 2327730 A1 CA2327730 A1 CA 2327730A1 CA 002327730 A CA002327730 A CA 002327730A CA 2327730 A CA2327730 A CA 2327730A CA 2327730 A1 CA2327730 A1 CA 2327730A1
- Authority
- CA
- Canada
- Prior art keywords
- fumarate
- molecular weight
- poly
- polydispersity index
- average molecular
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- -1 poly(propylene fumarate) Polymers 0.000 title claims abstract description 40
- 229920001299 polypropylene fumarate Polymers 0.000 title claims abstract description 23
- 239000002516 radical scavenger Substances 0.000 title claims description 14
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 title abstract description 63
- 230000015572 biosynthetic process Effects 0.000 title description 10
- 230000010933 acylation Effects 0.000 title description 7
- 238000005917 acylation reaction Methods 0.000 title description 7
- 238000003786 synthesis reaction Methods 0.000 title description 7
- 238000000034 method Methods 0.000 claims abstract description 36
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims abstract description 30
- 229910000027 potassium carbonate Inorganic materials 0.000 claims abstract description 15
- ZLYYJUJDFKGVKB-OWOJBTEDSA-N (e)-but-2-enedioyl dichloride Chemical compound ClC(=O)\C=C\C(Cl)=O ZLYYJUJDFKGVKB-OWOJBTEDSA-N 0.000 claims abstract description 13
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000000203 mixture Substances 0.000 claims description 16
- 239000000178 monomer Substances 0.000 claims description 9
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 6
- 239000003999 initiator Substances 0.000 claims description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 4
- ZQMIGQNCOMNODD-UHFFFAOYSA-N diacetyl peroxide Chemical compound CC(=O)OOC(C)=O ZQMIGQNCOMNODD-UHFFFAOYSA-N 0.000 claims description 4
- 230000002194 synthesizing effect Effects 0.000 claims description 4
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 3
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical group C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 3
- 239000011256 inorganic filler Substances 0.000 claims description 3
- 229910003475 inorganic filler Inorganic materials 0.000 claims description 3
- 239000011780 sodium chloride Substances 0.000 claims description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 2
- 239000004342 Benzoyl peroxide Substances 0.000 claims description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 2
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 2
- 238000012644 addition polymerization Methods 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 claims description 2
- 239000000872 buffer Substances 0.000 claims description 2
- 229920001577 copolymer Polymers 0.000 claims description 2
- 229910052588 hydroxylapatite Inorganic materials 0.000 claims description 2
- XYJRXVWERLGGKC-UHFFFAOYSA-D pentacalcium;hydroxide;triphosphate Chemical compound [OH-].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O XYJRXVWERLGGKC-UHFFFAOYSA-D 0.000 claims description 2
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical group [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 claims description 2
- CTEFDDZVRLFMNT-NSCUHMNNSA-N (e)-4-(3-hydroxypropoxy)-4-oxobut-2-enoic acid Chemical compound OCCCOC(=O)\C=C\C(O)=O CTEFDDZVRLFMNT-NSCUHMNNSA-N 0.000 claims 3
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 claims 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims 2
- 150000008041 alkali metal carbonates Chemical class 0.000 claims 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 2
- UOULCEYHQNCFFH-UHFFFAOYSA-M sodium;hydroxymethanesulfonate Chemical compound [Na+].OCS([O-])(=O)=O UOULCEYHQNCFFH-UHFFFAOYSA-M 0.000 claims 2
- 150000005323 carbonate salts Chemical class 0.000 claims 1
- 239000003431 cross linking reagent Substances 0.000 claims 1
- 230000000399 orthopedic effect Effects 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 19
- AYAUWVRAUCDBFR-ONEGZZNKSA-N (e)-4-oxo-4-propoxybut-2-enoic acid Chemical compound CCCOC(=O)\C=C\C(O)=O AYAUWVRAUCDBFR-ONEGZZNKSA-N 0.000 abstract description 7
- 239000002253 acid Substances 0.000 abstract description 7
- 239000006227 byproduct Substances 0.000 abstract description 6
- 238000012545 processing Methods 0.000 abstract description 2
- 229920000642 polymer Polymers 0.000 description 21
- 210000000988 bone and bone Anatomy 0.000 description 12
- 239000007943 implant Substances 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 238000005809 transesterification reaction Methods 0.000 description 9
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 8
- 238000001228 spectrum Methods 0.000 description 8
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 7
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 7
- 229910052799 carbon Inorganic materials 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 239000002131 composite material Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 238000001157 Fourier transform infrared spectrum Methods 0.000 description 4
- 238000004132 cross linking Methods 0.000 description 4
- 238000005755 formation reaction Methods 0.000 description 4
- 238000001727 in vivo Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 3
- 239000002639 bone cement Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 229920006158 high molecular weight polymer Polymers 0.000 description 3
- 238000002513 implantation Methods 0.000 description 3
- 229920001155 polypropylene Polymers 0.000 description 3
- 238000010189 synthetic method Methods 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 2
- 238000005452 bending Methods 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 230000036541 health Effects 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 230000004060 metabolic process Effects 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 239000003361 porogen Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 230000002028 premature Effects 0.000 description 2
- 150000003138 primary alcohols Chemical class 0.000 description 2
- 150000003333 secondary alcohols Chemical class 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000007039 two-step reaction Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- PFNQVRZLDWYSCW-UHFFFAOYSA-N (fluoren-9-ylideneamino) n-naphthalen-1-ylcarbamate Chemical compound C12=CC=CC=C2C2=CC=CC=C2C1=NOC(=O)NC1=CC=CC2=CC=CC=C12 PFNQVRZLDWYSCW-UHFFFAOYSA-N 0.000 description 1
- XILIYVSXLSWUAI-UHFFFAOYSA-N 2-(diethylamino)ethyl n'-phenylcarbamimidothioate;dihydrobromide Chemical compound Br.Br.CCN(CC)CCSC(N)=NC1=CC=CC=C1 XILIYVSXLSWUAI-UHFFFAOYSA-N 0.000 description 1
- 238000005084 2D-nuclear magnetic resonance Methods 0.000 description 1
- 206010003694 Atrophy Diseases 0.000 description 1
- 208000018084 Bone neoplasm Diseases 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 244000205754 Colocasia esculenta Species 0.000 description 1
- 235000006481 Colocasia esculenta Nutrition 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 238000007171 acid catalysis Methods 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000037444 atrophy Effects 0.000 description 1
- 238000005102 attenuated total reflection Methods 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 239000012620 biological material Substances 0.000 description 1
- 229910001417 caesium ion Inorganic materials 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 238000011088 calibration curve Methods 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- PBAYDYUZOSNJGU-UHFFFAOYSA-N chelidonic acid Natural products OC(=O)C1=CC(=O)C=C(C(O)=O)O1 PBAYDYUZOSNJGU-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000010265 fast atom bombardment Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 238000012933 kinetic analysis Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- JDEJGVSZUIJWBM-UHFFFAOYSA-N n,n,2-trimethylaniline Chemical compound CN(C)C1=CC=CC=C1C JDEJGVSZUIJWBM-UHFFFAOYSA-N 0.000 description 1
- XUZLXCQFXTZASF-UHFFFAOYSA-N nitro(phenyl)methanol Chemical compound [O-][N+](=O)C(O)C1=CC=CC=C1 XUZLXCQFXTZASF-UHFFFAOYSA-N 0.000 description 1
- 230000002188 osteogenic effect Effects 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 231100001055 skeletal defect Toxicity 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 238000012549 training Methods 0.000 description 1
- 229940078499 tricalcium phosphate Drugs 0.000 description 1
- 229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/52—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
- C08G63/56—Polyesters derived from ester-forming derivatives of polycarboxylic acids or of polyhydroxy compounds other than from esters thereof
-
- 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
- A61L24/0047—Composite materials, i.e. containing one material dispersed in a matrix of the same or different material
- A61L24/0073—Composite materials, i.e. containing one material dispersed in a matrix of the same or different material with a macromolecular matrix
- A61L24/0084—Composite materials, i.e. containing one material dispersed in a matrix of the same or different material with a macromolecular matrix containing fillers of phosphorus-containing inorganic compounds, e.g. apatite
-
- 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
-
- 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
- A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
- A61L27/14—Macromolecular materials
- A61L27/18—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
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/52—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Surgery (AREA)
- Medicinal Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Composite Materials (AREA)
- Dermatology (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Transplantation (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Polymers & Plastics (AREA)
- Materials Engineering (AREA)
- Polyesters Or Polycarbonates (AREA)
- Materials For Medical Uses (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8130898P | 1998-04-10 | 1998-04-10 | |
| US8140598P | 1998-04-10 | 1998-04-10 | |
| US60/081,308 | 1998-04-10 | ||
| US60/081,405 | 1998-04-10 | ||
| US8218298P | 1998-04-16 | 1998-04-16 | |
| US60/082,182 | 1998-04-16 | ||
| PCT/US1999/007912 WO1999052469A1 (en) | 1998-04-10 | 1999-04-09 | Synthesis of poly(propylene fumarate) by acylation of propylene glycol in the presence of a proton scavenger |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2327730A1 true CA2327730A1 (en) | 1999-10-21 |
Family
ID=27373944
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002327730A Abandoned CA2327730A1 (en) | 1998-04-10 | 1999-04-09 | Synthesis of poly(propylene fumarate) by acylation of propylene glycol in the presence of a proton scavenger |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US6124373A (https=) |
| EP (1) | EP1079869B1 (https=) |
| JP (1) | JP2002539275A (https=) |
| AT (1) | ATE291444T1 (https=) |
| CA (1) | CA2327730A1 (https=) |
| DE (1) | DE69924369D1 (https=) |
| WO (1) | WO1999052469A1 (https=) |
Families Citing this family (46)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6486232B1 (en) * | 1997-04-18 | 2002-11-26 | Cambridge Scientific, Inc. | Bioerodible polymeric semi-interpenetrating network alloys for internal fixation devices and bone cements |
| WO1999052469A1 (en) | 1998-04-10 | 1999-10-21 | Wm. Marsh Rice University | Synthesis of poly(propylene fumarate) by acylation of propylene glycol in the presence of a proton scavenger |
| JP2002542349A (ja) * | 1999-04-16 | 2002-12-10 | ダブリューエム・マーシュ・ライス・ユニバーシティー | ポリ（プロピレンフマラート）−ジアクリレートマクロマーで交差結合された生体分解性のポリ（プロピレンフマラート）ネットワーク |
| US6884778B2 (en) * | 2000-04-14 | 2005-04-26 | William Marsh Rice University | Biocompatible macromers |
| DE10032220A1 (de) | 2000-07-03 | 2002-01-24 | Sanatis Gmbh | Magnesium-ammonium-phosphat-Zemente, deren Herstellung und Verwendung |
| US6849223B2 (en) * | 2001-04-19 | 2005-02-01 | Case Western Reserve University | Fabrication of a polymeric prosthetic implant |
| DE60226242T2 (de) * | 2001-06-28 | 2009-05-28 | William Marsh Rice University, Houston | Photoquervernetzung von biologischen materialien aus fumarsäurediethylester/poly(propylenfumarat) |
| US7629388B2 (en) | 2001-11-20 | 2009-12-08 | William Marsh Rice University | Synthesis and characterization of biodegradable cationic poly(propylene fumarate-co-ethylene glycol) copolymer hydrogels modified with agmatine for enhanced cell adhesion |
| WO2003065996A2 (en) | 2002-02-05 | 2003-08-14 | Cambridge Scientific, Inc. | Bioresorbable osteoconductive compositions for bone regeneration |
| US6884432B2 (en) * | 2002-04-25 | 2005-04-26 | Mayo Foundation For Medical Education And Research | Blend, cross-linkable poly(propylene fumarate) for immobilization and controlled drug delivery |
| US7273523B2 (en) * | 2002-06-07 | 2007-09-25 | Kyphon Inc. | Strontium-apatite-cement-preparations, cements formed therefrom, and uses thereof |
| US20070065652A1 (en) * | 2003-03-13 | 2007-03-22 | Willaim Marsh Rice University | Composite injectable and pre-fabricated bone replacement material and method for the production of such bone replacement material |
| AU2003214708A1 (en) | 2003-03-14 | 2004-09-30 | Roque Humberto Ferreyro Irigoyen | Hydraulic device for the injection of bone cement in percutaneous vertebroplasty |
| US8066713B2 (en) | 2003-03-31 | 2011-11-29 | Depuy Spine, Inc. | Remotely-activated vertebroplasty injection device |
| US8415407B2 (en) | 2004-03-21 | 2013-04-09 | Depuy Spine, Inc. | Methods, materials, and apparatus for treating bone and other tissue |
| WO2006011152A2 (en) * | 2004-06-17 | 2006-02-02 | Disc-O-Tech Medical Technologies, Ltd. | Methods for treating bone and other tissue |
| US20070043202A1 (en) * | 2003-07-01 | 2007-02-22 | Yaszemski Michael J | Self-crosslinkable poly(caprolactone fumarate) |
| US7252686B2 (en) * | 2003-08-13 | 2007-08-07 | Boston Scientific Scimed | Methods for reducing bone compression fractures using wedges |
| WO2005030034A2 (en) | 2003-09-26 | 2005-04-07 | Depuy Spine, Inc. | Device for delivering viscous material |
| US20060018949A1 (en) * | 2004-04-07 | 2006-01-26 | Bausch & Lomb Incorporated | Injectable biodegradable drug delivery system |
| KR20060134223A (ko) | 2004-04-27 | 2006-12-27 | 키폰 인크. | 뼈 대체 조성물 및 사용 방법 |
| WO2006053031A2 (en) * | 2004-11-12 | 2006-05-18 | Mayo Foundation For Medical Education And Research | Photocrosslinkable poly(caprolactone fumarate) |
| JP4897699B2 (ja) * | 2004-11-18 | 2012-03-14 | メイヨ フオンデーシヨン フオー メデイカル エジユケーシヨン アンド リサーチ | ポリカプロラクトンとポリ（プロピレンフマレート）とのブロックコポリマー |
| ATE511439T1 (de) * | 2005-04-29 | 2011-06-15 | Mayo Foundation | Hydrophile/hydrophobe polymernetze auf der basis von poly(caprolactonfumarat), poly(ethylenglycolfumarat) und copolymere davon |
| US9381024B2 (en) | 2005-07-31 | 2016-07-05 | DePuy Synthes Products, Inc. | Marked tools |
| US9918767B2 (en) | 2005-08-01 | 2018-03-20 | DePuy Synthes Products, Inc. | Temperature control system |
| US7651701B2 (en) * | 2005-08-29 | 2010-01-26 | Sanatis Gmbh | Bone cement composition and method of making the same |
| US8360629B2 (en) | 2005-11-22 | 2013-01-29 | Depuy Spine, Inc. | Mixing apparatus having central and planetary mixing elements |
| US7754005B2 (en) * | 2006-05-02 | 2010-07-13 | Kyphon Sarl | Bone cement compositions comprising an indicator agent and related methods thereof |
| US7507286B2 (en) * | 2006-06-08 | 2009-03-24 | Sanatis Gmbh | Self-foaming cement for void filling and/or delivery systems |
| WO2008001385A2 (en) * | 2006-06-29 | 2008-01-03 | Depuy Spine, Inc. | Integrated bone biopsy and therapy apparatus |
| CA2663447A1 (en) | 2006-09-14 | 2008-03-20 | Depuy Spine, Inc. | Polymeric bone cement and methods of use thereof |
| ES2389784T3 (es) * | 2006-09-21 | 2012-10-31 | Kyphon SÀRL | Fosfato de diamonio y otras sales de amonio y su uso para prevenir la coagulación de la sangre |
| CA2665995C (en) * | 2006-10-19 | 2011-11-29 | Oren Globerman | Fluid delivery system |
| US20080195223A1 (en) * | 2006-11-03 | 2008-08-14 | Avram Allan Eddin | Materials and Methods and Systems for Delivering Localized Medical Treatments |
| ATE551967T1 (de) * | 2007-07-30 | 2012-04-15 | Purzer Pharmaceutical Co Ltd | Biologisch abbaubarer knochenzement und herstellungsverfahren dafür |
| US20090286907A1 (en) * | 2008-01-23 | 2009-11-19 | Beltz Mark W | Fumaric Acid/Diol Polyesters and Their Manufacture and Use |
| US7968616B2 (en) * | 2008-04-22 | 2011-06-28 | Kyphon Sarl | Bone cement composition and method |
| EP2590605A1 (en) | 2010-07-09 | 2013-05-15 | Board of Regents of the University of Texas System | Biodegradable scaffolds |
| EP2605805B1 (en) | 2010-08-20 | 2019-01-09 | Case Western Reserve University | Continuous digital light processing additive manufacturing of implants |
| US11865785B2 (en) * | 2010-08-20 | 2024-01-09 | H. David Dean | Continuous digital light processing additive manufacturing of implants |
| EP3139962B1 (en) | 2014-05-05 | 2020-12-23 | Advanced Medical Solutions Israel (Sealantis) Ltd | Biological adhesives and sealants and methods of using the same |
| BR112017010057B1 (pt) * | 2014-11-18 | 2022-11-29 | The Ohio State University | Método para produzir um polímero de polipropileno fumarato para uso em impressão 3d |
| US11499008B2 (en) | 2017-02-02 | 2022-11-15 | University Of Akron | Functionalized poly (propylene fumarate) polymers made by ring opening polymerization using magnesium catalysts |
| GB2594243A (en) * | 2020-04-15 | 2021-10-27 | Arterius Ltd | A bone cement |
| WO2022015989A1 (en) * | 2020-07-15 | 2022-01-20 | The University Of Akron | Synthesis of poly (propylene maleate-co-succinate) by the time-dependent reduction of poly (propylene maleate) double bonds mediated by zinc and acetic acid |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3701748A (en) | 1966-07-20 | 1972-10-31 | Rohm & Haas | Unsaturated polyester resinous compositions |
| GB1225803A (https=) * | 1967-06-02 | 1971-03-24 | ||
| US5286763A (en) * | 1983-03-22 | 1994-02-15 | Massachusetts Institute Of Technology | Bioerodible polymers for drug delivery in bone |
| US4722948A (en) * | 1984-03-16 | 1988-02-02 | Dynatech Corporation | Bone replacement and repair putty material from unsaturated polyester resin and vinyl pyrrolidone |
| US5989579A (en) | 1986-10-02 | 1999-11-23 | Escalon Medical Corp. | Ocular insert with anchoring protrusions |
| US4843112A (en) * | 1987-03-12 | 1989-06-27 | The Beth Israel Hospital Association | Bioerodable implant composition |
| US4888413A (en) | 1988-01-11 | 1989-12-19 | Domb Abraham J | Poly(propylene glycol fumarate) compositions for biomedical applications |
| FI904598A7 (fi) | 1989-10-10 | 1991-04-11 | Wrigley W M Jun Co | Kuidunkehruutekniikalla valmistetut ainetta vähitellen vapauttavat rakenteet |
| FR2661682B1 (fr) | 1990-05-04 | 1993-12-10 | Norsolor | Nouvelles compositions resineuses a base de resines polyesters non saturees et de nouveaux additifs anti-retrait. |
| KR100266912B1 (ko) | 1992-02-28 | 2000-12-01 | 파라비 레이 | 조직접촉물질이며 방출조절운반체인 광중합성 생분해성 하이드로겔 |
| US5733951A (en) * | 1994-04-28 | 1998-03-31 | Yaszemski; Michael J. | Poly(propylene fumarate) |
| US5527864A (en) * | 1995-08-08 | 1996-06-18 | Suggs; Laura J. | Poly(propylene fumarate-co-ethylene oxide) |
| EP0782326B1 (en) | 1995-12-25 | 2001-10-10 | Sharp Kabushiki Kaisha | Image-forming system |
| US5998362A (en) | 1996-09-12 | 1999-12-07 | Merck & Co., Inc. | Conjugates useful in the treatment of prostate cancer |
| US6071982A (en) | 1997-04-18 | 2000-06-06 | Cambridge Scientific, Inc. | Bioerodible polymeric semi-interpenetrating network alloys for surgical plates and bone cements, and method for making same |
| US5854382A (en) | 1997-08-18 | 1998-12-29 | Meadox Medicals, Inc. | Bioresorbable compositions for implantable prostheses |
| WO1999052469A1 (en) | 1998-04-10 | 1999-10-21 | Wm. Marsh Rice University | Synthesis of poly(propylene fumarate) by acylation of propylene glycol in the presence of a proton scavenger |
-
1999
- 1999-04-09 WO PCT/US1999/007912 patent/WO1999052469A1/en not_active Ceased
- 1999-04-09 JP JP2000543082A patent/JP2002539275A/ja active Pending
- 1999-04-09 DE DE69924369T patent/DE69924369D1/de not_active Expired - Fee Related
- 1999-04-09 AT AT99915349T patent/ATE291444T1/de not_active IP Right Cessation
- 1999-04-09 US US09/289,361 patent/US6124373A/en not_active Expired - Lifetime
- 1999-04-09 CA CA002327730A patent/CA2327730A1/en not_active Abandoned
- 1999-04-09 EP EP99915349A patent/EP1079869B1/en not_active Expired - Lifetime
-
2000
- 2000-10-04 US US09/678,816 patent/US6355755B1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| WO1999052469A1 (en) | 1999-10-21 |
| US6355755B1 (en) | 2002-03-12 |
| WO1999052469A9 (en) | 2000-03-23 |
| EP1079869B1 (en) | 2005-03-23 |
| JP2002539275A (ja) | 2002-11-19 |
| ATE291444T1 (de) | 2005-04-15 |
| EP1079869A1 (en) | 2001-03-07 |
| DE69924369D1 (de) | 2005-04-28 |
| US6124373A (en) | 2000-09-26 |
| EP1079869A4 (en) | 2002-08-07 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US6355755B1 (en) | Synthesis of poly(propylene fumarate) by acylation of propylene glycol in the presence of a proton scavenger | |
| JP3161729B2 (ja) | ラクチドとε−カプロラクトンとの共重合体から医療に応用できる物品を製造する方法 | |
| KR100696407B1 (ko) | 폴리(프로필렌 푸마레이트)-디아크릴레이트 마크로머와가교결합된 생분해성 폴리(프로필렌 푸마레이트) 네트워크 | |
| JP3481762B2 (ja) | ポリ（アルキレンジグリコレート）、コポリマー、ブレンド、それらの製造方法及びそれらを用いた医療器具 | |
| Kharas et al. | Synthesis and characterization of fumarate‐based polyesters for use in bioresorbable bone cement composites | |
| US8962786B2 (en) | Chain extenders | |
| AU2001262159B2 (en) | Compositions of crosslinkable prepolymers for biodegradable implants | |
| JP2986509B2 (ja) | 変性ポリエステル樹脂組成物、その製造方法、およびその用途 | |
| US5688900A (en) | Absorbable polyalkylene diglycolates | |
| EP0617712B1 (en) | Copolymer of lactone and carbonate and process for the preparation of such a copolymer | |
| JP5527968B2 (ja) | ポリ（カプロラクトンフマレート）、ポリ（エチレングリコールフマレート）およびそれらのコポリマーに基づく親水性／疎水性ポリマーネットワーク | |
| US6602963B2 (en) | Polyesters containing (meth)acrylate end groups | |
| KR102614952B1 (ko) | 몰딩 특성을 가지는 형상 기억 고분자 기반 치과용 멤브레인 및 이의 제조방법 | |
| AU2006294414B2 (en) | Chain extenders | |
| Peter | Injectable, in situ polymerizable, biodegradable scaffolds based on poly (propylene fumarate) for guided bone regeneration | |
| AU2005219452B2 (en) | Biocompatible polymer compositions for dual or multistaged curing | |
| Ho | Injectable biodegradable poly (ester-co-ether) methacrylate monomers for bone tissue engineering and drug delivery applications | |
| CN112646142A (zh) | 共聚物、共聚物的制备方法以及手术器械 | |
| Herath | Synthesis and characterization of novel biodegradable crosslinked polyesters | |
| MXPA97003652A (en) | Absalbib polyalykylene diglycollates |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |