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Segmented, epsilon-caprolactone-rich, poly(epsilon-caprolactone-co-p-dioxanone) copolymers for medical applications and devices therefrom

A technology of dioxanone and copolymer, which is applied in medical science, prosthesis, antibacterial drugs, etc.

Inactive Publication Date: 2014-09-24
CORDIS CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there has been very limited clinical success

Method used

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  • Segmented, epsilon-caprolactone-rich, poly(epsilon-caprolactone-co-p-dioxanone) copolymers for medical applications and devices therefrom
  • Segmented, epsilon-caprolactone-rich, poly(epsilon-caprolactone-co-p-dioxanone) copolymers for medical applications and devices therefrom
  • Segmented, epsilon-caprolactone-rich, poly(epsilon-caprolactone-co-p-dioxanone) copolymers for medical applications and devices therefrom

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0126] Example 1: Poly(ε-caprolactone-co- Synthesis of p-dioxanone) Triblock Copolymer

[0127] Using a 10 gallon stainless steel oil jacketed reactor equipped with agitation, 4,123 grams of ε-caprolactone was added along with 63.9 grams of diethylene glycol and 16.6 mL of a 0.33M stannous octoate solution in toluene. After the initial charge, a purge cycle was performed in an upward direction using agitation at a rotational speed of 6 RPM. The reactor was evacuated to a pressure of less than 550 mTorr, followed by introduction of nitrogen. The cycle is repeated one more time to ensure a dry atmosphere. At the end of the final nitrogen purge, the pressure was adjusted to slightly over one atmosphere. The vessel was heated at a rate of 180°C / hour by setting the oil controller at 195°C. The reaction lasted 6 hours and 10 minutes from the time the oil temperature reached 195°C.

[0128] In the next stage, the oil controller set point was lowered to 120°C and 20,877 grams ...

example 2

[0131] Example 2: Poly(ε-caprolactone-co-p Synthesis of Dioxanone) Triblock Copolymer (PDO-rich Cap / PDO Copolymer)

[0132] Using a 10 gallon stainless steel oil jacketed reactor equipped with agitation, 4,123 grams of ε-caprolactone was added along with 90.2 grams of diethylene glycol and 23.4 mL of a 0.33M stannous octoate solution in toluene. The reaction conditions in the first stage closely matched those in Example 1.

[0133] In the second copolymerization stage, the oil controller set point was lowered to 120°C and 32,089 grams of molten p-dioxanone monomer was added from the melt tank with stirring rotation at 7.5 RPM in a downward direction for 40 minutes . The oil controller was then set to 115°C for 20 minutes, then to 104°C for one hour and 45 minutes, and finally to 115°C for 15 minutes before draining. The post-curing phase (80°C / 4 days) and the grinding and sieving procedure were carried out according to Example 1. The ground and sieved polymer had a net ...

example 3

[0135] Example 3: Poly(ε-caprolactone-co-p-dioxa) enriched in ε-caprolactone in 91 / 9 molar segments Synthesis of cyclohexanone) triblock copolymer (Cap / PDO copolymer rich in Cap) [75 / 25 Initial feed charge for Cap / PDO]

[0136] Using a 10 gallon stainless steel oil jacketed reactor equipped with agitation, 18,492 grams of ε-caprolactone was added along with 19.1 grams of diethylene glycol and 26.2 mL of a 0.33M stannous octoate solution in toluene. After the initial charge, start the purge cycle in the down direction using agitation at a rotational speed of 10 RPM. The reactor was evacuated to a pressure of less than 500 mTorr, followed by introduction of nitrogen. The cycle is repeated one more time to ensure a dry atmosphere. At the end of the final nitrogen purge, the pressure was adjusted to slightly over one atmosphere. The rotational speed of the stirrer was reduced to 7 RPM in the downward direction. The vessel was heated at a rate of 180°C / hour by setting the ...

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Abstract

Novel semi-crystalline, epsilon-caprolactone-rich block copolymers of epsilon-caprolactone and p-dioxanone for long term absorbable medical applications are disclosed. The novel polymer compositions are useful for long term absorbable surgical sutures, and other medical devices. Also disclosed are compositions and methods of using tissue engineered blood vessels to repair and regenerate blood vessels of patients with vascular disease.

Description

technical field [0001] The present invention relates to novel semicrystalline, block copolymers of ε-caprolactone and p-dioxanone enriched in ε-caprolactone for long-term absorbable medical applications, especially surgical sutures and hernia meshes things. The invention also relates to tissue engineered blood vessels for treating vascular diseases. Background technique [0002] Synthetic absorbable polyesters are well known. The open patent literature describes inter alia the formation of glycolide, L(-)-lactide, D(+)-lactide, meso-lactide, ε-caprolactone, p-dioxane Polymers and copolymers of ketones and trimethylene carbonate. [0003] A very important application of absorbable polymers is their use as surgical sutures. Absorbable sutures generally come in two basic forms: multifilament braids and monofilament fibers. For a polymer to function as a monofilament, it must generally possess a glass transition temperature T below room temperature g . low T g Helps ensu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61L17/10A61L31/06C08G63/08C08G63/664A61L17/00
CPCA61L17/005A61L17/105A61L2300/202A61L27/507C08G63/664A61K31/09A61L31/06C08G63/08A61L31/16A61L27/54A61L17/12A61L27/3826A61L27/56A61L2300/404A61L27/18A61P31/04C08L67/04
Inventor D.D.贾米奥科维斯基S.安德杰里M.厄内特
Owner CORDIS CORP
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