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Method for making a polysaccharide dialdehyde having high purity

A polysaccharide and dialdehyde technology, which is applied in the field of preparing high-purity polysaccharide dialdehyde, can solve the problems of slow, not very suitable for large-scale preparation of polysaccharide dialdehyde, etc.

Inactive Publication Date: 2010-03-03
EI DU PONT DE NEMOURS & CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, dialysis is a slow process requiring many days and is therefore not well suited for the large-scale production of polysaccharide dialdehydes

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0062] Preparation of dextran dialdehydes having an average molecular weight of 8,500 to 11,5000

[0063] The purpose of this example was to prepare a dextran dialdehyde having an average molecular weight of 8,500 to 11,500 Daltons and a total iodine content of less than 0.03% by weight.

[0064] In a 1 L glass reaction vessel equipped with a mechanical stirrer and addition funnel, 37.5 g of sodium periodate and 350 mL of deionized water were added. The reactor contents were stirred until all solids were dissolved. The reactor was cooled to 20 °C. Using an addition funnel, to the periodate solution was added a solution containing 37.5 g of dextran (average molecular weight 8,500 to 11,500; Sigma Chemical Co, St Louis, MO, catalog number D9260) dissolved in 300 mL of deionized water. After the addition was complete, the reactor contents were stirred at 20 °C for 5 h. At the end of the reaction time, the reactor contents were transferred to a beaker and the beaker was coole...

Embodiment 2

[0067] Preparation of dextran dialdehyde having an average molecular weight of 60,000 to 90,000

[0068] The purpose of this example was to prepare a dextran dialdehyde having an average molecular weight of 60,000 to 90,000 Daltons and a total iodine content of less than 0.03% by weight.

[0069] Using the method described in Example 1, except that the dextran has an average molecular weight of 60,000 to 90,000 Daltons (Sigma Chemical Co, St Louis, MO, catalog number D3759), and the amount of sodium periodate is 18.75g.

[0070] Using proton nuclear magnetic resonance, the dialdehyde content of the product was determined to be 28%. The solid product was analyzed using X-ray fluorescence spectroscopy and found to contain 0.225% by weight chlorine, 0.019% by weight iodine, 0.0475% by weight calcium, and 0.185% by weight potassium, with an overall purity of 99.98% by weight.

Embodiment 3

[0072] Without the optional initial cooling step, the preparation has an average molecular weight of 60,000 to 90,000 and about 27% oxidation degree of dextran dialdehyde

[0073] The purpose of this example was to prepare a dextran dialdehyde having an average molecular weight of 60,000 to 90,000 Daltons and a degree of oxidation of about 27% and a total iodine content of less than 0.03% by weight. The purification method does not involve optional cooling to a crystallization temperature below about 5°C to form a precipitate comprising at least one periodate.

[0074] Into a 20 L reactor equipped with a mechanical stirrer, addition funnel, built-in thermocouple and nitrogen purge, 1.00 kg of dextran and 9.00 L of water were added. The mixture was stirred at ambient temperature to dissolve the dextran, and the solution was cooled to 10 to 15°C. A solution of 500 g of sodium periodate in 9.00 L of water was added to the reactor over about 1 hour while maintaining the tempe...

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Abstract

A method for making polysaccharide dialdehydes is disclosed, which uses a combination of precipitation and separation steps to purify the polysaccharide dialdehyde formed by oxidation of a polysaccharide with periodate. The method is simple, rapid, and provides a polysaccharide dialdehyde having very low levels of iodine-containing species. The polysaccharide dialdehyde is particularly suitable for preparing hydrogel adhesives for medical applications.

Description

[0001] Cross References to Related Applications [0002] This patent application claims priority to US Provisional Application Serial No. 60 / 925,948 (filed April 20, 2007), the disclosure of which is incorporated herein by reference for all purposes as if fully set forth herein. field of invention [0003] The present invention relates to the field of medical adhesives. More specifically, the present invention relates to a process for the preparation of high purity forms of polysaccharide dialdehydes useful in the preparation of hydrogel adhesives for medical applications. Background of the invention [0004] Tissue adhesives have many potential medical applications, including closing wounds, assisting or replacing sutures or staples in medical and surgical procedures, adhering synthetic coverings or inlays to the cornea, drug delivery devices, and as preventive surgery Post-adhesive anti-stick barrier. Conventional tissue adhesives are generally not suitable for a wide r...

Claims

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Application Information

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IPC IPC(8): C08B37/00
CPCC08B37/0021C08B37/00
Inventor J·D·科亨H·K·舍诺R·S·希菲诺
Owner EI DU PONT DE NEMOURS & CO
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