WO1998030617A1 - Hydrogels - Google Patents
Hydrogels Download PDFInfo
- Publication number
- WO1998030617A1 WO1998030617A1 PCT/GB1998/000068 GB9800068W WO9830617A1 WO 1998030617 A1 WO1998030617 A1 WO 1998030617A1 GB 9800068 W GB9800068 W GB 9800068W WO 9830617 A1 WO9830617 A1 WO 9830617A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- polyol
- polyester
- water
- polyesters
- reaction
- Prior art date
Links
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
- C08G63/66—Polyesters containing oxygen in the form of ether groups
- C08G63/668—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds
-
- 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
- A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
- A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
- A61L15/42—Use of materials characterised by their function or physical properties
- A61L15/60—Liquid-swellable gel-forming materials, e.g. super-absorbents
-
- 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
-
- 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
- A61L27/50—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
- A61L27/52—Hydrogels or hydrocolloids
-
- 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
- A61L31/00—Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
- A61L31/04—Macromolecular materials
- A61L31/06—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
- A61L31/00—Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
- A61L31/14—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
- A61L31/145—Hydrogels or hydrocolloids
-
- 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
Definitions
- the present invention relates to hydrogels.
- the present invention relates to polyester hydrogels.
- Polyesters of succinic acid are known from US Patent No.3, 883,901. Such polyesters are the reaction product of a succinate ester, such as diethyl succinate, and a glycol, such as polyethylene glycol.
- polyesters produced by reacting succinic anhydride with a polyol containing three or more hydroxy groups are novel and advantageous.
- polyester comprising residues of succinic acid and a polyol containing three or more hydroxy groups.
- a water swellable hydrogel comprising a polyester which polyester comprises residues of succinic acid and a polyol containing three or more hydroxy groups.
- a water swellable hydrogel a three- dimensional network of a super absorbent polymer which interacts with aqueous solutions by swelling and retains a significant proportion of water within its structure.
- a super absorbent polymer is understood to mean a polymer which is capable of having an equilibrium water content of at least 30% w/w.
- M n number average molecular weight
- the high molecular weight polyesters of the invention are also advantageous over prior art polyesters in that they exhibit crosslinking.
- cross-linked polyester of succinic anhydride and a polyol eg. a cross-linked polyester comprising residues of succinic acid and a polyol containing three or more hydroxy groups.
- Such cross-linked copolyesters generally act as hydrogels.
- poiyols containing three or more hydroxy groups known per se are suitable for use in the present invention.
- Such poiyols include, for example, polyether poiyols or polyhydroxyalkanes. It should be noted that the poiyols for use in the present invention should not be limited to the polyether poiyols or the polyhydroxyalkanes.
- n is a number from 3 to 6
- polyester of the invention are suitable for the preparation of the polyester of the invention and include, for example, glycerol, sorbitol, mannitol, adonite, ribite, dulcitol, erythritol and xylite.
- Poiyols such as triols which may be mentioned include trihydroxyaikanes such as glycerol.
- polyether poiyols examples include those sold under the range of TP30 by Perstorp.
- polyesters of the invention may be prepared using conventional methods known per se.
- the method of manufacturing a polyester according to the invention may optionally include the use of a catalyst.
- Preferred catalysts are acid catalysts and especially protic acid catalysts.
- Particular protic acid catalysts which may be mentioned include sulphuric acid, methane sulphonic acid and p-toluene sulphonic acid.
- the ratios of the succinic anhydride and the polyol in the polymerisation reaction will depend upon, inter alia, the functionality of the polyol, that is, the number of free hydroxy groups and the degree of cross-linking required in the resulting polyester.
- succinic anhydride has a functionality of 2
- glycerol which has two primary and one secondary hydroxy group is also considered to possess a functionality of 2 since the secondary hydroxy is less reactive than the primary hydroxy groups.
- the ratio of succinic anhydride to polyol should be from 0.7:1 to 1 :1.3, preferably 1 :1.
- a polyester of succinic anhydride and a trioi such as glycerol should comprise preferably 3 units of succinic anhydride to 2 units of glycerol, eg. giving a preferred functionality ratio of 1 :1.
- Polyesters according to the invention may be characterised using conventional techniques known per se, such as infra red spectroscopy, nmr, rheological measurements, glass transition measurements and water uptake.
- the polyesters according to the invention are particularly advantageous in that they are biodegradable.
- they may be useful in preparing biodegradable implants such as medical or surgical prostheses, supports for such prostheses, supports for cell cultures such as may be used in ligament, cartilage or tendon repair, supports for cell cultures in woundcare or as woundcare agents in their own right, eg. debnding agents, pharmaceutical carriers etc. or the copolyesters of the invention may be useful in imaging during interventional procedures.
- polyesters of the invention are also advantageous in that they are sterilisable. Any conventional form of sterilisation may be used, eg. steam sterilisation, but an especial benefit of the polyesters of the invention is that they may be sterilised without detrimental effect by x-radiation.
- Polyesters produced from succinic anhydride and diols are known in the prior art to be useful as bioresorbable sutures. Experimental results indicate that such polyesters, as well as the polyesters of the present invention may be especially useful in wound healing, eg. as a debriding agent.
- a polyester comprising residues of succinic anhydride and a polyol in the manufacture of a wound healing agent, eg. a debriding agent.
- a method of wound healing which comprises applying a polyester comprising residues of succinic acid and a polyol to the wound of a patient.
- the desiccator was heated in an oven at 80° for 5 to 15 mins with the tap open. It was then heated with the tap closed for a further 15 to 16 hrs at 80°. The resulting materials were heated in a vacuum oven at 70°.
- a second series of materials were prepared containing various levels of glycerol and TP30.
- the formulations are shown in Table IV.
- Table V shows the degrees of conversion p(CooH) for these materials, calculated using the method shown below.
- c) is assumed to be negligible since the anhydride is stored under nitrogen, though any water absorbed would convert the anhydride to succinic acid and would therefore manifest itself as an error in b). This water would in fact be liberated during the reaction, d) is assumed to be negligible since the reaction is carried out in a sealed system in the presence of a drying agent, followed by vacuum treatment.
- m a is the mass of the anhydride in the mixture (during the initial mixing procedure)
- m r is the total mass of mixture poured onto the release paper
- M a is the molecular mass of succinic anhydride.
- Figure 1 shows the percentage weight gain of the materials prepared without glycerol in both deionised water and phosphate buffered saline (PBS) as a function of time (batch number PC0695042, from Reaction 261/12, Table III)
- Figure 2 shows the percentage weight gain of the materials with 50% glycerol (based on mol % primary OH) in both deionised water and PBS as a function of time (batch number PC0695041 , from Reaction 261/13, Table IV)
- Figure 3 shows the percentage weight gain of the materials with 75% glycerol (based on mol % primary OH) in both deionised water and PBS as a function of time (Reaction 261/14, Table IV)
- Example 6 FTIR Spectroscopy
- Figure 4 shows the FTIR spectra of the polyester produced from reaction 261/7 from Example 3 (Table IV) and Figure 5 shows that of the reaction product from Reaction 261/10 of Example 3 (Table V).
Abstract
Description
Claims
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU55665/98A AU5566598A (en) | 1997-01-11 | 1998-01-09 | Hydrogels |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB9700508.6 | 1997-01-11 | ||
GBGB9700508.6A GB9700508D0 (en) | 1997-01-11 | 1997-01-11 | Hydrogels |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1998030617A1 true WO1998030617A1 (en) | 1998-07-16 |
Family
ID=10805842
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/GB1998/000068 WO1998030617A1 (en) | 1997-01-11 | 1998-01-09 | Hydrogels |
Country Status (4)
Country | Link |
---|---|
AU (1) | AU5566598A (en) |
GB (1) | GB9700508D0 (en) |
WO (1) | WO1998030617A1 (en) |
ZA (1) | ZA98167B (en) |
Cited By (34)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2003064496A2 (en) * | 2001-10-22 | 2003-08-07 | Massachusetts Institute Of Technology | Biodegradable polymer |
US7722894B2 (en) | 2001-10-22 | 2010-05-25 | Massachusetts Institute Of Technology | Biodegradable polymer |
USRE43282E1 (en) | 1998-09-14 | 2012-03-27 | The Board Of Trustees Of The Leland Stanford Junior University | Assessing the condition of a joint and devising treatment |
US8143042B2 (en) | 2006-01-12 | 2012-03-27 | Massachusetts Institute Of Technology | Biodegradable elastomers |
US8545569B2 (en) | 2001-05-25 | 2013-10-01 | Conformis, Inc. | Patient selectable knee arthroplasty devices |
US8862202B2 (en) | 1998-09-14 | 2014-10-14 | The Board Of Trustees Of The Leland Stanford Junior University | Assessing the condition of a joint and preventing damage |
US8882847B2 (en) | 2001-05-25 | 2014-11-11 | Conformis, Inc. | Patient selectable knee joint arthroplasty devices |
US8906107B2 (en) | 2001-05-25 | 2014-12-09 | Conformis, Inc. | Patient-adapted and improved orthopedic implants, designs and related tools |
US8912304B2 (en) | 2007-05-17 | 2014-12-16 | Massachusetts Institute Of Technology | Polyol-based polymers |
US8932363B2 (en) | 2002-11-07 | 2015-01-13 | Conformis, Inc. | Methods for determining meniscal size and shape and for devising treatment |
US8951259B2 (en) | 2001-05-25 | 2015-02-10 | Conformis, Inc. | Patient selectable joint arthroplasty devices and surgical tools |
US8951260B2 (en) | 2001-05-25 | 2015-02-10 | Conformis, Inc. | Surgical cutting guide |
US8998915B2 (en) | 2001-05-25 | 2015-04-07 | Conformis, Inc. | Joint arthroplasty devices and surgical tools |
US9020788B2 (en) | 1997-01-08 | 2015-04-28 | Conformis, Inc. | Patient-adapted and improved articular implants, designs and related guide tools |
US9017334B2 (en) | 2009-02-24 | 2015-04-28 | Microport Orthopedics Holdings Inc. | Patient specific surgical guide locator and mount |
US9023050B2 (en) | 2001-05-25 | 2015-05-05 | Conformis, Inc. | Surgical tools for arthroplasty |
US9055953B2 (en) | 2001-05-25 | 2015-06-16 | Conformis, Inc. | Methods and compositions for articular repair |
US9066728B2 (en) | 2001-05-25 | 2015-06-30 | Conformis, Inc. | Surgical tools facilitating increased accuracy, speed and simplicity in performing joint arthroplasty |
US9180015B2 (en) | 2008-03-05 | 2015-11-10 | Conformis, Inc. | Implants for altering wear patterns of articular surfaces |
CN105358185A (en) * | 2013-04-10 | 2016-02-24 | 墨尔本大学 | Biodegradable network polymers for regenerative medicine and tissue engineering |
US9286686B2 (en) | 1998-09-14 | 2016-03-15 | The Board Of Trustees Of The Leland Stanford Junior University | Assessing the condition of a joint and assessing cartilage loss |
US9308091B2 (en) | 2001-05-25 | 2016-04-12 | Conformis, Inc. | Devices and methods for treatment of facet and other joints |
US9308053B2 (en) | 2006-02-06 | 2016-04-12 | Conformis, Inc. | Patient-specific joint arthroplasty devices for ligament repair |
US9326780B2 (en) | 2006-02-06 | 2016-05-03 | Conformis, Inc. | Patient selectable joint arthroplasty devices and surgical tools incorporating anatomical relief |
US9387079B2 (en) | 2001-05-25 | 2016-07-12 | Conformis, Inc. | Patient-adapted and improved articular implants, designs and related guide tools |
US9486226B2 (en) | 2012-04-18 | 2016-11-08 | Conformis, Inc. | Tibial guides, tools, and techniques for resecting the tibial plateau |
US9495483B2 (en) | 2001-05-25 | 2016-11-15 | Conformis, Inc. | Automated Systems for manufacturing patient-specific orthopedic implants and instrumentation |
US9579110B2 (en) | 2001-05-25 | 2017-02-28 | Conformis, Inc. | Patient selectable joint arthroplasty devices and surgical tools |
US9603711B2 (en) | 2001-05-25 | 2017-03-28 | Conformis, Inc. | Patient-adapted and improved articular implants, designs and related guide tools |
US9642632B2 (en) | 2009-02-24 | 2017-05-09 | Microport Orthopedics Holdings Inc. | Orthopedic surgical guide |
US9649117B2 (en) | 2009-02-24 | 2017-05-16 | Microport Orthopedics Holdings, Inc. | Orthopedic surgical guide |
US9675471B2 (en) | 2012-06-11 | 2017-06-13 | Conformis, Inc. | Devices, techniques and methods for assessing joint spacing, balancing soft tissues and obtaining desired kinematics for joint implant components |
US9700971B2 (en) | 2001-05-25 | 2017-07-11 | Conformis, Inc. | Implant device and method for manufacture |
US10085839B2 (en) | 2004-01-05 | 2018-10-02 | Conformis, Inc. | Patient-specific and patient-engineered orthopedic implants |
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-
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- 1997-01-11 GB GBGB9700508.6A patent/GB9700508D0/en active Pending
-
1998
- 1998-01-09 WO PCT/GB1998/000068 patent/WO1998030617A1/en active Application Filing
- 1998-01-09 AU AU55665/98A patent/AU5566598A/en not_active Abandoned
- 1998-01-09 ZA ZA98167A patent/ZA98167B/en unknown
Patent Citations (1)
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JPS6031802B2 (en) * | 1978-03-22 | 1985-07-24 | 日清製油株式会社 | cosmetics |
Non-Patent Citations (2)
Title |
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CHEMICAL ABSTRACTS, vol. 104, no. 12, 24 March 1986, Columbus, Ohio, US; abstract no. 95260, HIGAKI ET AL.: "Novel, hydrophilic polyol esters for hair preparations" XP002061206 * |
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US8862202B2 (en) | 1998-09-14 | 2014-10-14 | The Board Of Trustees Of The Leland Stanford Junior University | Assessing the condition of a joint and preventing damage |
US9286686B2 (en) | 1998-09-14 | 2016-03-15 | The Board Of Trustees Of The Leland Stanford Junior University | Assessing the condition of a joint and assessing cartilage loss |
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Also Published As
Publication number | Publication date |
---|---|
ZA98167B (en) | 1998-07-13 |
AU5566598A (en) | 1998-08-03 |
GB9700508D0 (en) | 1997-02-26 |
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