NZ773678B2 - Self-lubricating medical articles - Google Patents
Self-lubricating medical articlesInfo
- Publication number
- NZ773678B2 NZ773678B2 NZ773678A NZ77367819A NZ773678B2 NZ 773678 B2 NZ773678 B2 NZ 773678B2 NZ 773678 A NZ773678 A NZ 773678A NZ 77367819 A NZ77367819 A NZ 77367819A NZ 773678 B2 NZ773678 B2 NZ 773678B2
- Authority
- NZ
- New Zealand
- Prior art keywords
- medical article
- diisocyanate
- polyurethane
- based resin
- glycol
- Prior art date
Links
- 239000011347 resin Substances 0.000 claims abstract 13
- 229920005989 resin Polymers 0.000 claims abstract 13
- 239000004814 polyurethane Substances 0.000 claims abstract 11
- 229920002635 polyurethane Polymers 0.000 claims abstract 11
- 150000002009 diols Chemical group 0.000 claims abstract 10
- 125000005442 diisocyanate group Chemical group 0.000 claims abstract 7
- 229920000151 polyglycol Polymers 0.000 claims abstract 7
- 239000010695 polyglycol Substances 0.000 claims abstract 7
- 239000004970 Chain extender Substances 0.000 claims abstract 6
- -1 polysiloxane Polymers 0.000 claims abstract 5
- 239000010702 perfluoropolyether Substances 0.000 claims abstract 4
- 229920001296 polysiloxane Polymers 0.000 claims abstract 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 7
- 239000004615 ingredient Substances 0.000 claims 4
- 229920001515 polyalkylene glycol Polymers 0.000 claims 4
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 claims 2
- 239000002202 Polyethylene glycol Substances 0.000 claims 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims 2
- 239000007795 chemical reaction product Substances 0.000 claims 2
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 claims 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 2
- 229920001223 polyethylene glycol Polymers 0.000 claims 2
- 229920000909 polytetrahydrofuran Polymers 0.000 claims 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims 2
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims 2
- 238000009827 uniform distribution Methods 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 1
- 229920001774 Perfluoroether Polymers 0.000 claims 1
- 229920001030 Polyethylene Glycol 4000 Polymers 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims 1
- 229920000515 polycarbonate Polymers 0.000 claims 1
- 239000004417 polycarbonate Substances 0.000 claims 1
- 229920000728 polyester Polymers 0.000 claims 1
- 229920005604 random copolymer Polymers 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 229910014033 C-OH Inorganic materials 0.000 abstract 1
- 229910014570 C—OH Inorganic materials 0.000 abstract 1
- 125000003158 alcohol group Chemical group 0.000 abstract 1
- 230000003373 anti-fouling effect Effects 0.000 abstract 1
- 239000004205 dimethyl polysiloxane Substances 0.000 abstract 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 abstract 1
Classifications
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- A61L2400/00—Materials characterised by their function or physical properties
- A61L2400/10—Materials for lubricating medical devices
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- A61L29/00—Materials for catheters, medical tubing, cannulae, or endoscopes or for coating catheters
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- A61L29/00—Materials for catheters, medical tubing, cannulae, or endoscopes or for coating catheters
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- 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
-
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- A61M25/00—Catheters; Hollow probes
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M157/00—Lubricating compositions characterised by the additive being a mixture of two or more macromolecular compounds covered by more than one of the main groups C10M143/00 - C10M155/00, each of these compounds being essential
- C10M157/04—Lubricating compositions characterised by the additive being a mixture of two or more macromolecular compounds covered by more than one of the main groups C10M143/00 - C10M155/00, each of these compounds being essential at least one of them being a nitrogen-containing compound
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M157/00—Lubricating compositions characterised by the additive being a mixture of two or more macromolecular compounds covered by more than one of the main groups C10M143/00 - C10M155/00, each of these compounds being essential
- C10M157/10—Lubricating compositions characterised by the additive being a mixture of two or more macromolecular compounds covered by more than one of the main groups C10M143/00 - C10M155/00, each of these compounds being essential at least one of them being a compound containing atoms of elements not provided for in groups C10M157/02 - C10M157/08
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M171/00—Lubricating compositions characterised by purely physical criteria, e.g. containing as base-material, thickener or additive, ingredients which are characterised exclusively by their numerically specified physical properties, i.e. containing ingredients which are physically well-defined but for which the chemical nature is either unspecified or only very vaguely indicated
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
- C10M2209/104—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing two carbon atoms only
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2213/00—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2213/06—Perfluoro polymers
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2217/045—Polyureas; Polyurethanes
- C10M2217/0453—Polyureas; Polyurethanes used as base material
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
- C10M2229/02—Unspecified siloxanes; Silicones
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/06—Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/50—Medical uses
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2050/00—Form in which the lubricant is applied to the material being lubricated
- C10N2050/023—Multi-layer lubricant coatings
Abstract
Medical articles formed from a polyurethane-based resin including a modifying oligomer provide enhanced properties. A modifying oligomer incorporated into a backbone, as a side chain, or both of the polyurethane-based resin formed by a diisocyanate, a polyglycol, and a diol chain extender has at least one, preferably two, alcohol moieties (C-OH) and a functional moiety. Exemplary modifying oligomers are: a diol-containing perfluoropolyether incorporated into the backbone, a monofunctional polysiloxane (e.g., monodialcoholterminated polydimethylsiloxane) incorporated as the side chain, and combinations thereof. Medical articles herein are self-lubricating and/or anti-fouling.
Claims (14)
1. A medical article formed from a polyurethane-based resin, which is a random copolymer of a reaction product of the following ingredients: a diisocyanate; a diol chain extender; a polyglycol; and a modifying oligomer incorporated into a backbone of the polyurethane-based resin formed by the diisocyanate, the polyglycol, and the diol chain extender, the modifying oligomer comprising a diol-containing perfluoropolyether incorporated into the backbone, the diol-containing perfluoropolyether having a structure of HO(CH CH O) CH CF O(CF CF O) (CF O) CF CH (OCH2CH2) OH 2 2 p 2 2 2 2 q 2 r 2 2 p wherein p+q+r provide a fluorine content in a range of 55% to 60% by weight and the average molecular weight of the modifying oligomer is in the range of 1500 to 2200 g/mol wherein a hard segment content is in the range of from 25% to 75% by weight and a soft segment content of the resin is in the range of from 75% to 25% by weight; and wherein a concentration of the modifying oligomer of the polyurethane-based resin at a surface of the medical article is higher than a theoretical concentration based on uniform distribution of ingredients of the polyurethane-based resin, and the medical article is effective as a self-lubricating and/or self-anti-fouling medical article.
2. The medical article of claim 1, wherein the modifying oligomer further comprises a monofunctional polysiloxane incorporated as the side chain.
3. The medical article of claim 1, wherein the modifying oligomer is present in an amount ranging from about 0.1 to about 10 weight percent of the overall composition of the polyurethane-based resin.
4. The medical article of claim 1, wherein the diisocyanate is selected from the group consisting of: an aliphatic diisocyanate, alicyclic diisocyanate and an aromatic diisocyanate.
5. The medical article of claim 4, wherein the diisocyanate is selected from the group consisting of: 4,4’-diphenylmethane diisocyanate (MDI), toluene diisocyanate (TDI), isophorone diisocyanate (IPDI), and methylene-bis(4-cyclohexylisocyanate) (HMDI), and combinations thereof.
6. The medical article of claim 1, wherein the diol chain extender is selected from the group consisting of: ethylene glycol, 1,3-propylene glycol, 1,4-butanediol, neopentyl glycol, and alicyclic glycols having up to 10 carbon atoms.
7. The medical article of claim 1, wherein the polyglycol is selected from the group consisting of: polyalkylene glycol, polyester glycol, polycarbonate glycol, and combinations thereof.
8. The medical article of claim 1, wherein the polyglycol comprises the polyalkylene glycol.
9. The medical article of claim 1, wherein the polyalkylene glycol comprises one or both of: a polytetramethylene ether glycol and a polyethylene glycol.
10. The medical article of claim 1, wherein the polyalkylene glycol comprises a polytetramethylene ether glycol, and a polyethylene glycol that comprises PEG4000.
11. A medical article formed from a polyurethane-based resin, which is a reaction product of the following ingredients: a diisocyanate; a diol chain extender; a polyglycol; and a modifying oligomer incorporated into a backbone, as a side chain, or both of the polyurethane-based resin formed by the diisocyanate, the polyglycol, and the diol chain extender, the modifying oligomer comprising a diol-containing perfluoropolyether incorporated into the backbone, a monofunctional polysiloxane incorporated as the side chain; wherein a hard segment content is in the range of from 25% to 75% by weight and a soft segment content of the resin is in the range of from 75% to 25% by weight; and wherein the medical article has a contact angle with water that is 90° or greater.
12. The medical article of claim 11, wherein the modifying oligomer has an alcohol (C- OH) moiety and a functional moiety.
13. The medical article of claim 12, wherein the functional moiety comprises a fluoroether, a silicone, or a combination thereof.
14. The medical article of claim 11 comprising a concentration of the modifying oligomer of the polyurethane-based resin at a surface of the medical article is higher than a theoretical concentration based on uniform distribution of ingredients of the polyurethane-based resin.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201862735332P | 2018-09-24 | 2018-09-24 | |
US16/577,824 US11613719B2 (en) | 2018-09-24 | 2019-09-20 | Self-lubricating medical articles |
PCT/US2019/052351 WO2020068617A1 (en) | 2018-09-24 | 2019-09-23 | Self-lubricating medical articles |
Publications (2)
Publication Number | Publication Date |
---|---|
NZ773678A NZ773678A (en) | 2024-01-26 |
NZ773678B2 true NZ773678B2 (en) | 2024-04-30 |
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