Hydrogel material based on cross-linked polyvinyl alcohol

FIELD: medicine.

SUBSTANCE: invention relates to medicine, namely to medicinal hydrogel polymer materials, used as a base for the creation of polymer implants and products, contacting with blood. Described is a non-porous hydrogel material based on a modified polyvinyl alcohol, which contains unsaturated radicals in side chains, obtained by polymerisation at 0-250°C in a solution or in polymer powder sintering at 100-180°C. Also described is a combined material, containing a matrix of the porous hydrogel polymer material and reinforcing filler, filling the matrix, of the non-porous hydrogel material obtained by the said method.

EFFECT: materials are liquid-impermeable, possess biocompatibility, high strength characteristics and high stability at heating.

3 cl, 3 ex

 

The technical field

The present invention relates to medicine, namely to medical hydrogel polymeric materials and products on their basis, including, for creating polymeric implants and articles in contact with blood.

Prior art

Materials based on polyvinyl alcohol are widely used in medical fields. A typical example of that can be attributed to the analogues of the material, is the material described in the monograph SATHE R. D. Design And Development of a Novel Implantable Prosthetic Vein Valve // A Thesis Presented to The Academic Faculty, Georgia Institute of Technology, May, 2006.

In this case, a material traditionally obtained on the basis of physical hydrogels of high molecular weight polyvinyl alcohol formed in the cycles of thawing-freezing" [cryogels).

A significant disadvantage of this technical solution is the relatively low thermal stability of this material [HASSAN, S. M., STEWART J. E., PEPPAS N. A. Diffusional characteristics of freeze/thawed poly(vinyl alcohol) hydrogels: Applications to protein controlled release from multilaminate devices // European Journal of Pharmaceutics and Biopharmaceutics, 2000, V. 49, p.161 to 165), soluble at temperatures close to the boiling temperature of water. The consequence of this is the need for fixing structure using cross-linking agents and/or radiation hard. This greatly complicates the technology which increases the risk of complications in the practical application of the material, associated with the possibility of incomplete cleaning material from the cross-linking agents and products of radiation-induced destruction of polyvinyl alcohol.

The closest analogue of the present invention is a gel material on the basis of modified polyvinyl alcohol containing in the side chain double bond (patent RU 2328313, "Macroporous gel material and products on its basis", published 10.07.2008). Cross-linking of molecules in obtaining polymeric material is in this case not due to hydrogen bonds, and by chemical crosslinking by free radical mechanism. Therefore, this material does not require additional fixing structure and high stability when heated. However, the known polymeric material on the basis of modified polyvinyl alcohol is formed in the water-frozen solutions that require very specific hardware design, in addition, the resulting material has a porous structure and is permeable to liquids, which does not allow to use it as a structural material, for example, to create products for cardiovascular surgery.

Disclosure of inventions

Object of the present invention is to provide a hydrogel material suitable for use as design the frame in cardiovascular surgery, including, to create a polymeric implants and articles in contact with blood.

The technical result of the invention is to provide a non-porous hydrogel material based on polyvinyl alcohol, which is impervious to liquids, possessing biocompatibility, high mechanical strength and high stability when heated.

This technical result is achieved by obtaining non-porous hydrogel material based on the modified polyvinyl alcohol of General formula (I)

,

where

R represents H,

R1HE

R2-O-CO-R4,

R3represents an unsaturated group selected from CH2=CH-CO-O-,

CH2=C(CH3)-CO-O-,

CH3-CH=CH-CH=CH-CO-O-,

CH3-CH=CH-CO-O-,

C6H5-CH=CH-CO-O-,

CH2=C(CH3)-CO-O-CH2-CH(OH)-CH2-O-,

CH2=CH-CO-O-CH2-CH(OH)-CH2-O-,

CH2=CH-O-,

CH2=CH-CH2-O-,

CH2=CH-O-CH2-CH2-O - or

CH2=CH-CH2-O-CH2-CH(OH)-CH2-O-,

R4-CH3or the residue of another acid, polyvinyl ether which was obtained polyvinyl alcohol,

n=75-99,5 molar percent (mol.%),

m=0-12 mol.%,

k=0.5 to 25 mol.%,

when carrying out the polymerization at a temperature 0-250°C in solution or when is pecunia powder polymer at a temperature of 100-180°C.

The use of the modified polyvinyl alcohol of General formula (I) containing in the side chain double bond, as the basis for obtaining hydrogel material allows to obtain a hydrogel material that does not require additional fixing structure, which eliminates the risk of toxicity due to the presence of cross-linking agents. This material also has a high stability when heated.

Conducting polymerization under conditions of high temperatures, i.e., without the step of freezing the polymer solution, was suddenly possible to obtain on the basis of modified polyvinyl alcohol of General formula (I) hydrogel material having the desired characteristics: non-porous, biocompatible, high strength, impermeable to liquids and heat stable, i.e., a material suitable for use as structural in cardiovascular surgery, including, for creating polymeric implants and articles in contact with blood.

As the basis for the hydrogel material used modified polyvinyl alcohol of General formula (I), which is a water-soluble derivatives of polyvinyl alcohol with a molecular weight Mw=5000-1000000.

Introduced into a side chain unsaturated radicals R3contains one or two unsaturated communication and which allows the formation of spatial patterns in radical polymerization and copolymerization. The radical R3may contain the residue of an unsaturated acid, for example, acrylic, methacrylic, sorbic, crotonic, cinnamic:

CH2=CH-CO-O-,

CH2=C(CH3)-CO-O-,

CH3-CH=CH-CH=CH-CO-O-,

CH3-CH=CH-CO-O-,

C6H5-CH=CH-CO-O-,

CH2=C(CH3)-CO-O-CH2-CH(OH)-CH2-O-,

CH2=CH-CO-O-CH2-CH(OH)-CH2-O-,

or alanovoy group, for example,

CH2=CH-O-,

CH2=CH-CH2-O-,

CH2=CH-O-CH2-CH2-O-

or CH2=CH-CH2-O-CH2-CH(OH)-CH2-O-.

The number of groups with multiple bonds contained in the side chain of the polymer, can vary (k=0.5 to 25 mol.%), however, it should be sufficient to achieve the desired degree of crosslinking of polyvinyl alcohol in accordance with the desired physical and functional properties of a material, such as, for example, the hardness of the resulting gel (from soft to hard). Therefore, the number of such groups may be different depending on the destination of the material. So, for example, to increase the strength of the material, the number of such groups in the polymer composition can be large, while for increasing the ductility of the material can be used a polymer with a lower degree of substitution.

Synthesis of hydrogels can be carried out in a solution of modified polyvinyl alcohol, during sintering of the powder of the polymer. The solvent can act as water and organic solvents (for example, formamide, dimethylformamide, a solution of dimethyl sulfoxide, dimethylacetamide, etc. and their mixtures. The concentration of the solution may be in the range from 0.5 to 30 wt.%. The process can be carried out in the presence of radical polymerization initiators (for example, organic and inorganic peroxides), and in their absence - by thermal initiation. Temperature of synthesis (0÷250°C) is determined experimentally and is caused by the type of solvent and/or initiator. The sintering powder of the polymer is conducted at a temperature of 100-180°C.

In addition, this method allows you to enter in the composition of the material at the stage of formation of additional functional groups, which allows to obtain composite materials based on polyvinyl alcohol. The receipt of such materials is possible by adding at the stage of joining to the modified polyvinyl alcohol of General formula (I) various low molecular weight unsaturated comonomers, such as acrylamide, isopropylacrylamide, etilenglikolevykh, acrylic methacrylic, sorbic, crotonic, cinnamic acid, dimethylaminoethylacrylate, diethylaminoacetate, etc. may be entered, p is at least one of the additional functional groups. The introduction of additional functional groups allows you to expand the range of characteristics of the final product, for example, makes it possible to adsorption on the material surface proteins or drugs due to electrostatic interactions between the carrier and the surface groups of the adsorbed substances in that case, if the composition of the material entered the charged group.

The proposed method can also be applied to obtain a composite material containing a matrix of a porous hydrogel polymer material obtained by conducting polymerization of the modified polyvinyl alcohol of General formula (I) in water frozen solutions, as described in more detail in the patent RU 2328313, and a reinforcing filler, representing non-porous hydrogel material based on the modified polyvinyl alcohol of General formula (I) obtained by conducting polymerization in solution. Receiving the combined material is carried out by modifying and filling the matrix of the porous hydrogel polymeric material is a non-porous hydrogel of polyvinyl alcohol. Thus, to obtain a combined material polymerization macromer [modified polyvinyl alcohol General the formula (I) in solution (water, based and organic solvent) is performed on lyophilized porous film, placed on a Teflon substrate.

The obtained composite material has better mechanical properties.

The implementation of the invention

1) Example of a film material.

A portion of the modified polymer based on polyvinyl alcohol composition

(m=94,4 mol.%; n=4,3 mol.%, k=l,3 mol.%, Mw=25 000) weighing 1 g was dissolved by heating in 25 ml of distilled water, cooled to room temperature, was added 0.06 g of potassium persulfate in 1.5 ml of distilled water, the mixture was evacuated to remove dissolved air. Then poured in a Teflon shape so that the thickness of the water layer does not exceed 1 mm Uniform was placed in a heat chamber and was heated at 80°C for 1 h, then was dried to constant weight at a temperature of 90°C. At the end of the process the resulting film was washed in 200 ml of hot distilled water, and then dried at a temperature of 80°C to constant weight.

The resulting material has porosity and looks like a translucent film that is stable at temperatures close to the boiling temperature of water, over an indefinite period of time.

2) an Example of obtaining a combined material containing a matrix of porous geroge is avago polymer material.

To obtain a combined material use a matrix of porous hydrogel (porosity 10-90%, the average pore size of 0.1-100 μm), obtained in the following way: a portion of the modified polymer based on polyvinyl alcohol composition, similar to that specified in example 1, weighing 1 g was dissolved by heating in 25 ml of distilled water, cooled to room temperature, was added 0.06 g of potassium persulfate in 1.5 ml of distilled water, the mixture was evacuated to remove dissolved air. The mixture is then cooled to a temperature of 5°C was added 30 μl of N,N,N',N'-tetramethylethylenediamine. The mixture was poured into pre-cooled glass shape so that the thickness of the water layer was not more than ~0.5 mm, were frozen and kept for 6 hours at a temperature of -15°C. after the reaction form was unfrozen, the resulting macroporous hydrogel was washed in 200 ml of hot distilled water, and then freeze-dried.

Then, for reinforcement of the material and give it better mechanical properties, the resulting matrix is additionally modify and fill isotropic porous gel of polyvinyl alcohol as follows:

lyophilized porous film was placed on a Teflon substrate and applied to it a solution of macromer containing persulfate received similar is the rule example 1, then placed in a heat chamber and heated at 80°C for 1 h, the resulting film was washed with 300 ml of hot distilled water and dried to constant weight at 90°C.

3) Example of a film material, optionally containing charged groups

A portion of the modified polymer based on polyvinyl alcohol composition

(m=94,4 mol.%; n=4,3 mol.%, k=l,3 mol.%, Mw=25 000) weighing 1 g was dissolved by heating in 25 ml of distilled water, cooled to room temperature, was added 0.2 g of acrylic acid, and then 0.15 ml of 3% hydrogen peroxide solution and 0.3 ml of 15% solution of ascorbic acid, the mixture was evacuated to remove dissolved air. Then poured in a Teflon shape so that the thickness of the water layer does not exceed 1 mm, and kept for 4 hours at room temperature. Then the form was placed in a heat chamber and dried to constant weight at a temperature of 90°C. At the end of the process the resulting film was washed in 200 ml of hot distilled water, and then dried at a temperature of 80°C to constant weight.

The resulting material has porosity and looks like a translucent film, heat stable, and in addition, contains up to 10 mol.% the charged parts of acrylic acid.

1. A method of obtaining a non-porous hydrogel material on the again of the modified polyvinyl alcohol of General formula (I)
,
where
R represents H,
R1HE,
R2-O-CO-R4,
R3represents an unsaturated group selected from
CH2=CH-CO-O-,
CH2=C(CH3)-CO-O-,
CH3-CH=CH-CH=CH-CO-O-,
CH3-CH=CH-CO-O-,
C6H5-CH=CH-CO-O-,
CH2=C(CH3)-CO-O-CH2-CH(OH)-CH2-O-,
CH2=CH-CO-O-CH2-CH(OH)-CH2-O-,
CH2=CH-O-,
CH2=CH-CH2-O-,
CH2=CH-O-CH2-CH2-O - or
CH2=CH-CH2-O-CH2-CH(OH)-CH2-O-,
R4-CH3or the residue of another acid, polyvinyl ether which was obtained polyvinyl alcohol,
n=75-99,5 mol.%,
m=0-12 mol.%,
k=0.5 to 25 mol.%,
by conducting the polymerization at a temperature 0-250°C in solution or during sintering powder of the polymer at a temperature of 100-180°C.

2. The method according to p. 1, characterized in that at the stage of carrying out polymerization to the modified polyvinyl alcohol of General formula (I) optionally introducing at least one low molecular weight unsaturated comonomer selected from acrylamide, isopropylacrylamide, etilenglikolevykh, acrylic, methacrylic, sorbic, crotonic, cinnamic acid, dimethylaminoethylacrylate and diethylaminoacetate.

3. Composite material for use as structural in cardiovascular surgery, containing the s matrix of a porous hydrogel polymer material, obtained by carrying out polymerization of the modified polyvinyl alcohol of General formula (I) in water frozen solutions, and a reinforcing filler that fills the matrix, and represents a non-porous hydrogel material obtained by conducting polymerization in the solution method under item 1.



 

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