JP3001695B2 - Wound dressing - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a wound dressing, and more particularly to a wound dressing using a polyvinyl alcohol derivative having a specific structure.

[0002]

2. Description of the Related Art One of so-called hydrogels has been developed as a wound dressing. This is a gel containing water, and has excellent properties such as relief of pain by giving a cool feeling, absorptivity of exudate, and relief of pain when peeled from a wound site. In addition, it has been reported that wound healing is promoted by placing the wound site in a moderately moist environment (RGGeronemus, et al., J. Dermatol. Surg.
ncol., 8 ( 10 ), 850 (1982)), and it is extremely effective to use hydrogel as a wound dressing.

As such a hydrogel, for example, US Pat. Nos. 3,419,006 and 399,355
No. 1 and JP-A-59-82864 propose a wound hydrogel material obtained by irradiating an aqueous solution of polyether or aqueous solution of polyvinylpyrrolidone with radiation. Although this gel material has a high water content and is flexible, it requires enormous equipment and cost for irradiation.

Japanese Patent Application Laid-Open Nos. 58-92359 and 58-206751 disclose a wound dressing obtained by cooling and solidifying a polyvinyl alcohol aqueous solution to a temperature lower than -6 ° C., and then dehydrating in vacuum. Proposed. This wound dressing material is rich in mechanical strength, elasticity and flexibility, and has good touch, but has a problem that the manufacturing process is complicated.

[0005]

SUMMARY OF THE INVENTION As described above, the present invention has been found as a result of repeated studies to obtain a hydrogel exhibiting an excellent effect as a wound dressing material in a simple manufacturing process. By providing a photosensitive polyvinyl alcohol derivative having a specific structure as a constituent component, a wound dressing material that is soft and comfortable to the touch and can appropriately absorb exudate is provided.

[0006]

That is, the present invention relates to a method for preparing a polyvinyl alcohol derivative having a structural unit represented by the following structural formula (Formula 2) having a stilbazolium group bonded thereto in an amount of 0.5 to 3 mol%, and water. The present invention relates to a wound dressing material contained as an essential component.

[0007]

Embedded image

The polyvinyl alcohol derivative having the structural unit represented by the above formula (2) used in the present invention is disclosed in JP-B-56-5761, K. Ichimura, J. Polym. Sci.
ymerChemistry Edition, 20 , 1411 (1982), K. Ichimura, e
t al., J. Polym. Sci. Polymer Chemistry Edition, 20 , 1419
(1982), K. Ichimura, Macromol.Chem., 188, 2973 (198
7), Kunihiro Ichimura, Surface, 28 (9), 686 (1990).

The derivative is preferably prepared by acetalizing a styrylpyridium group having a formyl group to polyvinyl alcohol (hereinafter referred to as PVA), preferably 0.5 to 0.5%.
３3 mol%, particularly 0.8 to 2 mol%, that is, a polyvinyl alcohol having a stilbazolium group, which has water-soluble and photofunctional properties. This aqueous solution has a diameter of 410 nm or less, preferably 345 to 345 nm.
A gelation reaction occurs upon irradiation with light having a wavelength of 405 nm.
If the amount of the styrylpyridium group having a formyl group is less than 0.5 mol%, the mechanical strength of the wound dressing material becomes inferior, and if it exceeds 3 mol%, the flexibility is lowered. It becomes brittle and also becomes inferior in the liquid absorption of exudate.

The PVA derivative has a skeleton of polyvinyl alcohol, and has an average degree of polymerization of 500 or more, preferably 1000 or more, and more preferably 15 or more.
When it is about 00 to 2500, a decrease in mechanical strength when exudate from a wound site is absorbed can be suppressed. Therefore, it is possible to reduce the pain caused by the adhesiveness generated when the wound dressing of the present invention is peeled from the wound site. In addition, the degree of saponification is preferably at least 88 mol%, more preferably at least 99 mol%, from the viewpoint of exudate absorbability and mechanical strength.

The wound dressing of the present invention contains the above-mentioned PVA derivative, and its content is preferably 5 to 30% by weight, particularly preferably 7 to 15% by weight. When the content is less than 5% by weight, the mechanical strength of the coating material is not sufficient, and the handling property is poor, and the absorbability of exudate from the wound site may be poor. On the other hand, when the content is 30
If the amount is more than the weight percentage, the flexibility of the wound dressing tends to decrease, and the coating adhesion of the wound site may be poor.

Although the amount of water contained in the wound dressing of the present invention can be arbitrarily set, it is preferable to include as much water as possible in order to impart cool feeling and flexibility.
Usually, it is contained in the range of 70 to 95% by weight. Further, since the wound site is covered, it is preferable to use distilled water, particularly distilled water for injection, as much as possible.

The wound dressing of the present invention may contain, if necessary, a drug, a polyhydric alcohol, a water-soluble polymer, a water-absorbing resin, an inorganic filler, a preservative, etc. for the purpose of improving shape retention and imparting tackiness. Any amount can be included. As the polyhydric alcohol, glycerin, polyglycerin, ethylene glycol, diethylene glycol, polyethylene glycol, propylene glycol, dipropylene glycol, polypropylene glycol, ethylene / propylene glycol copolymer and the like can be used. Also,
Examples of the water-soluble polymer include polyvinyl alcohol, polyvinyl pyrrolidone, polyvinyl ether, vinyl ether / maleic anhydride copolymer, polyethylene oxide,
Polyacrylamide, polyethyleneimine, cellulose derivative, polyacrylic acid, sodium polyacrylate,
Polysaccharides and the like can be used. These polyhydric alcohols and water-soluble polymers may be used alone or in combination of two or more. Among the above-mentioned water-soluble polymers, wound healing ability is improved by appropriately increasing the water-absorbing ability using polyethylene oxide, a cellulose derivative, sodium polyacrylate or the like.

The drug which can be contained is not particularly limited. For example, popidone iodine, iodine, sulfadiazine, silver sulfadiazine as an antibacterial agent,
Benzalkonium chloride, cetalkonium chloride, methylbenzethonium, neomycin sulfate, hexachlorophen, eosin, penicillin G, cephalosin, cephaloridine, tetracycline, lincomycin, nystacin, kanamycin, penicillinase resistant penicillin, fradiomycin sulfate, silver lactate, etc. Drugs for haptics such as salicylic acid ester, menthol, camphor, peppermint, pepper extract, capsaicin as active substances, steroid drugs such as presonisolone, dexamethasone, hydrocortisone, nonsteroid drugs such as indomethacin, ketoprofen, diclofenac, ibuprofen, nitro Drugs for treating angina such as glycerin and isosorbide dinitrate, benzocaine, procaine, xyloca Local anesthetics, such as down, antihistamines such as diphenhydramine, alprenolol, propranolol, beta-blockers such pindolol, clonidine, antihypertensive agents such as nifedipine, methylephedrine, clorprenaline, salbutamol,
Contains one or more bronchodilators such as terbutamine, asthma drugs such as cromoglycic acid, plastaglandins, hormonal drugs, water-soluble collagen, aloe extract, loofah extract, various vitamins, and various Chinese herbs such as Toki and Shikon. Can be.

The wound dressing of the present invention has the above-mentioned constitution. Specifically, the following production method is given as an example.

That is, about 10% by weight of an aqueous solution of a PVA derivative is coated on a peelable film such as a polyester film to a final thickness of 10 to 3000 μm, preferably 10 to 3000 μm.
It is applied by casting so as to have a thickness of 0 to 2000 μm, and then covered with a transparent film.

After that, a UV of about 2 kW is output.
The wound dressing material of the present invention can be obtained by irradiating ultraviolet light with a lamp for an appropriate time to cause a gelling reaction.

In order to improve the shape-retaining property of the wound dressing material obtained as described above and to improve the handleability, for example, the wound dressing material may be laminated on a support in the above-mentioned production process, or a PVA derivative may be used. It is preferable that the aqueous solution is impregnated into a porous substrate such as a nonwoven fabric or a woven fabric, or the aqueous solution is cast on both surfaces of the substrate to gel.

[0019]

EXAMPLES Examples are shown below to specifically explain the wound dressing of the present invention.

Example 1 Stilbazolated polyvinyl alcohol (hereinafter referred to as PV)
A-Sbq; average polymerization degree 1700, saponification degree 88
(Mol%, Sbq introduction ratio 1.27 mol%) was cast into a 1 mm thick mold provided on a polyester film, and the above polyester film was covered from above.

Next, a UV lamp with an output of 2 kW is used for three sides of one side.
The wound dressing of the present invention was produced by irradiating both surfaces by 00 mJ / cm ² .

Example 2 PVA-Sbq (average degree of polymerization 1700, degree of saponification 99.
5 mol%, Sbq introduction rate 1.25 mol%) 10 wt%
A wound dressing of the present invention was produced in the same manner as in Example 1 except that an aqueous solution was used.

Example 3 The procedure of Example 1 was repeated, except that a 5% by weight aqueous solution of PVA-Sbq (average degree of polymerization 3000, saponification degree 88 mol%, Sbq introduction rate 1.30 mol%) was used. A wound dressing of the present invention was produced.

Example 4 The procedure of Example 1 was repeated, except that a 5% by weight aqueous solution of PVA-Sbq (average degree of polymerization: 1700, degree of saponification: 88 mol%, Sbq introduction rate: 2.90 mol%) was used. A wound dressing of the present invention was produced.

Example 5 The procedure of Example 1 was repeated, except that a 30% by weight aqueous solution of PVA-Sbq (average degree of polymerization: 500, degree of saponification: 88 mol%, Sbq introduction rate: 1.51 mol%) was used. A wound dressing of the present invention was produced.

Comparative Example 1 Wound was treated in the same manner as in Example 1 except that a 35% by weight aqueous solution of PVA-Sbq (average degree of polymerization: 500, saponification degree: 88 mol%, Sbq introduction rate: 0.3 mol%) was used. A coating material was produced.

Comparative Example 2 Wound was treated in the same manner as in Example 1 except that a 3% by weight aqueous solution of PVA-Sbq (average degree of polymerization 3000, saponification degree 88 mol%, Sbq introduction rate 3.5 mol%) was used. A coating material was produced.

Comparative Example 3 A 10% by weight aqueous solution of PVA (average degree of polymerization: 1700, saponification degree: 99.5 mol%) was cast on a polyester film in the same manner as in Example 1, and the polyester film was covered from above. Was.

After this was frozen at -20 ° C for 5 hours,
The gel was gradually melted at 5 ° C. for 10 hours to prepare a gel-like wound dressing.

The wound dressings obtained in Examples 1 to 5 and Comparative Examples 1 to 3 were subjected to the following tensile test and water absorption test, and the appearance at that time was also examined. FIG. 1 is a graph showing the results of the tensile test, and Table 1 shows the results of the water absorption test and the appearance after water absorption. In FIG. 1, the graph of Comparative Example 3 is a discontinuous line near the elongation of 300%, which is a so-called peak (yield point) in the stress near the elongation of 250%. Yield phenomenon occurs, further 300%
This indicates that sudden plastic strain occurred discontinuously in the vicinity, resulting in a temporary sudden decrease in stress.

<Tensile test> Each wound dressing was 1.5 cm
The sheet was cut into a size of × 5 cm, and a tensile test was carried out using an autograph (AG-2000) manufactured by Shimadzu Corporation while holding a position of 1 cm each from both ends of the long side. The distance between the chucks is 30m
m, and the pulling speed was 300 mm / min.

<Water Absorption Test> Each wound dressing was 1.5 cm
× 1.5cm, after measuring the weight before water absorption,
Each slice was placed in 150 ml of distilled water (32 ° C.) for 24 hours.
Dipped. After that, each cut piece was taken out, the surface moisture was wiped off, the weight after water absorption was measured, and the water absorption was calculated from the increased weight.

[0033]

[Table 1]

Example 6 PVA-Sbq (average degree of polymerization 2300, degree of saponification 99.
13 mol% of 5 mol%, Sbq introduction ratio 0.85 mol%)
Aqueous solution, 2mm thick provided on polyester film
And cast the polyester film from above. Then, both sides were irradiated by a UV lamp of 2 kW at 700 mJ / cm ^{2 on} each side to prepare a wound dressing of the present invention.

Example 7 PVA-Sbq (average polymerization degree 2300, saponification degree 99.
13 mol% of 5 mol%, Sbq introduction ratio 0.85 mol%)
To 90 parts by weight of the aqueous solution, 10 parts by weight of a 13% by weight aqueous solution of sodium polyacrylate (average molecular weight: 1,000,000) was added, and after defoaming, light irradiation was carried out in the same manner as in Example 6 to give the wound dressing material of the present invention. Was prepared.

Example 8 PVA-Sbq (average polymerization degree 2300, saponification degree 99.
13 mol% of 5 mol%, Sbq introduction ratio 0.85 mol%)
To 90 parts by weight of the aqueous solution, 10 parts by weight of a 13% by weight aqueous solution of polyethylene oxide (average molecular weight: 150,000 to 400,000) was added, and after defoaming, light irradiation was carried out in the same manner as in Example 6 to provide the wound dressing material of the present invention. Was prepared.

Example 9 PVA-Sbq (average polymerization degree 2300, saponification degree 99.
13 mol% of 5 mol%, Sbq introduction ratio 0.85 mol%)
30 parts by weight of a 13% by weight aqueous solution of sodium carboxymethylcellulose (average molecular weight of 100,000 to 110,000) was added to 70 parts by weight of the aqueous solution, and after defoaming, light irradiation was carried out in the same manner as in Example 6 to cover the wound of the present invention. Materials were produced.

Example 10 After light irradiation in Example 7, the water content was reduced to 75%.
The wound dressing material of the present invention was prepared by adjusting the weight%.

Example 11 After irradiation with light in Example 8, similarly to Example 10, the moisture content was adjusted to 75% by weight to prepare a wound dressing of the present invention.

Example 12 After irradiating light in Example 9, similarly to Example 10, the moisture content was adjusted to 75% by weight to prepare a wound dressing of the present invention.

With respect to the wound dressings prepared in Example 2 and Examples 6 to 12, distilled water in the above-described water absorption test was replaced with phosphate buffered saline (pH 7.4, 32).
° C), and the water absorption and the appearance after water absorption were observed. Table 2 shows the results.

[0042]

[Table 2]

[0043]

As described above, since the wound dressing of the present invention is a hydrogel obtained by irradiating an aqueous solution using a polyvinyl alcohol derivative having a specific structure with light, the production is extremely simple. Moreover, it has high mechanical strength, and is excellent in liquid absorbability of exudate from a wound site and shape retention after liquid absorption.

[Brief description of the drawings]

FIG. 1 is a graph showing the results of a tensile test performed on wound dressings obtained in Examples and Comparative Examples.

──────────────────────────────────────────────────の Continued on the front page (51) Int.Cl. ⁷ Identification symbol FI C08L 29/14 A61L 15/03 (72) Inventor Tetsuji Sugii 1-1-2 Shimohozumi, Ibaraki-shi, Osaka Nitto Denko Corporation (72) Inventor Masanori Sukunami 2--10-10 Hiyoshi, Kohoku-ku, Yokohama-shi, Kanagawa Prefecture Inspector Toshiko Nakata (58) Field surveyed (Int.Cl. ⁷ , DB name) A61L 15/16-15 / 24 A61L 15/44 A61F 13/00

Claims (3)

(57) [Claims] 1. A stilbazolium group having a content of 0.5 to 3 mol%.
A wound dressing material comprising, as essential components, a polyvinyl alcohol derivative having a structural unit represented by the following structural formula (Formula 1) and water bonded thereto. Embedded image 2. A wound dressing according to claim 1, further comprising a drug. 3. The wound dressing according to claim 1, which is irradiated with light.