Modified polyaryletherketone (PAEK) polymer and method for obtaining the same

A polyaryletherketone and polymer technology, applied in the field of modified polyaryletherketone polymer and its obtaining, can solve the problems of reduced serum concentration, inactivation, inactivation of RGD peptide and the like

Inactive Publication Date: 2016-04-06
UNIV DEL PAIS VASCO EUSKAL HERRIKO UNIBERTSITATEA +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] However, RGD peptides and OGP peptides or their cyclic surrogates are prone to rapid inactivation by proteolytic cleavage, resulting in reduced serum concentrations in systemic applications or surface inactivation when grafted onto biomaterials

Method used

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  • Modified polyaryletherketone (PAEK) polymer and method for obtaining the same
  • Modified polyaryletherketone (PAEK) polymer and method for obtaining the same
  • Modified polyaryletherketone (PAEK) polymer and method for obtaining the same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0109] Example 1: Dense PEEK, Porous PEEK and PEEK Surface Modified to Oxime

[0110] The pristine dense PEEK-A exhibited a contact angle of 84.1°±5.0 (Table 2) and a fluorescence of 192 (Table 3). The surface XPS analysis recorded at room temperature was C86.4%, O13.6% for pristine dense PEEK-A and C84.3%, O15.7% for mechanically polished dense PEEK-M (Table 4).

[0111] PEEK porous samples (PEEK-P) were prepared having a trimodal pore distribution with an average pore diameter of 120 μm to 180 μm interconnected by voids between adjacent pores of about 5 μm to 70 μm and exhibiting a mean diameter of 5 μm to 10 μm or Surface with smaller pore distribution. For this PEEK-P material, the measured contact angle value was 117.8°±1.0 (Table 2), and the fluorescence was 129.2 (Table 3). Surface XPS analysis: C78.2%, O21.8% (Table 4).

[0112] Densified PEEK materials and porous PEEK materials surface-modified with oximes were prepared according to the method described in Macrom...

Embodiment 2

[0116] Example 2: PEEK surface modified to azide. According to the material of the first aspect of the present invention, wherein R 1 ＝- CH 2 CH 2 -;X=N 3

[0117] 2-(p-Toluenesulfonyloxy)ethylazide: 2-Azidoethanol (2.5 g, 28.8 mmol) was added to pyridine ( 15 mL) and the mixture was stirred at this temperature for 24 hours. Then, add CH 2 Cl 2 (30mL) with NH 4 Cl and water wash solution. The organic phase was separated and dried (MgSO 4 ) and evaporated to give a colorless oil (5.6 g yield, 78%).

[0118] 1 H-RMN (500MHz, CDCl 3 ): δ7, 80 (d, 2H, Ar), 7, 40 (d, 2H, Ar), 4, 25 (t, 2H, OCH 2 ), 3, 50(t, 2H, NCH 2 ), 2, 50 (s, 3H, CH 3 ).

[0119] Under a nitrogen atmosphere, the dense PEEK-A oxime sample and the porous PEEK-P oxime sample (n=10 in each group) prepared as described in Example 1 were introduced into a mixture containing potassium carbonate (1.38 g, 10 mmol), 2-(p-toluene A mixture of sulfonyloxy)ethyl azide (1 g, 4 mmol) and acet...

Embodiment 3

[0122] Example 3: PEEK surface modified to maleimide. According to the material of the first aspect of the present invention, wherein R 1 ＝- CH 2 CH 2 -; X = N-maleimide

[0123] N-(2-p-toluenesulfonyloxyethyl)maleimide-furan ring adduct: N-(2-hydroxyethyl)maleimide furan ring adduct (0.5 g, 2.4 mmol) and p-toluenesulfonyl chloride (0.72 g, 3.8 mmol) were introduced into a spherical flask and dissolved in dichloromethane (40 mL). Then, pyridine (1.5 mL, 18 mmol) was added and the mixture was stirred at room temperature for 24 hours. Then, the solvent was evaporated and washed with NaHCO 3 The product was washed with saturated solution (20 mL×2) and HCl 1M solution (20 mL×2). Then, the product was dissolved in dichloromethane and allowed to evaporate. Yield: 587 mg, (67%).

[0124] 1 H-RMN (500MHz, CDCl 3 ): δ7, 79 (d, 2H, Ar-CH), 7, 36 (d, 2H, Ar-CH), 6, 54 (s, 2H, CH=CH), 5, 27 (s, 2H, CH ), 4, 22(t, 2H, CH 2 ), 3, 77 (t, 2H, CH 2 ), 2, 88 (s, 2H, ...

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Abstract

The invention relates to a modified polyaryletherketone (PAEK) polymer having surfaces chemically modified with azides, alkynes, thiols, maleimides, sulphonyl azides or thio acids, suitable for click reactions, and to a method for obtaining it. The invention further concerns conjugated biomaterials derived therefrom, PAEK-type materials having surfaces modified with an RGD (Arg-Gly-Asp) and / or OGP 10-14 (Tyr-Gly-Phe-Gly-Gly) peptidomimetic, and to a method for obtaining it. These materials are particularly useful for manufacturing medical devices. Finally, the invention also relates to a fluorescent PAEK material.

Description

technical field [0001] The present invention relates to modified polyaryletherketone polymers (PAEK) having azide, alkyne, Surfaces chemically modified with thiols, maleimides, sulfonyl azides, or thioacids. [0002] The present invention also relates to conjugated biomaterials derived therefrom, and methods for obtaining them, said conjugated biomaterials having undergone RGD (Arg-Gly-Asp) and / or OGP 10-14 (Tyr-Gly-Phe-Gly-Gly) Peptidomimetic modified surface PAEK type material. [0003] These materials are particularly useful in the manufacture of medical devices or tissue engineering or cell culture matrices. [0004] Finally, the invention also relates to fluorescent PAEK materials. Background technique [0005] PAEK is a thermoplastic material with acceptable biocompatibility that can be processed into fibers, films, coatings, matrices or porous materials and used to make implants and prosthetic devices. [0006] However, because PAEK exhibits poor tissue integratio...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61L27/18A61L31/06C08G65/48C08L71/12
CPCA61L27/18A61L27/56C08G65/48A61L2300/25A61L2300/412A61L2400/18A61L2430/02A61L2430/24A61L2430/38C08G2650/40C09K11/06C08L71/00C08G8/28C08J9/36C08J2361/16C09K2211/1416C09K2211/1466
Inventor 赫苏斯·马里亚·艾斯普鲁亚伊帕拉吉雷马伊亚伦·沙加特扎祖艾斯普鲁亚伊尼戈·布拉塞拉斯伊萨吉雷弗朗西斯科·哈维尔·阿斯皮罗斯多龙索罗乔斯巴·奥亚维德维库纳
Owner UNIV DEL PAIS VASCO EUSKAL HERRIKO UNIBERTSITATEA
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