WO2019027118A1

WO2019027118A1 - Composition for preparing artificial skin, containing fibrous polymer, and method for preparing artificial skin by using same

Info

Publication number: WO2019027118A1
Application number: PCT/KR2018/002697
Authority: WO
Inventors: 정석균; 김선화
Original assignee: 주식회사 메가코스
Priority date: 2017-07-31
Filing date: 2018-03-07
Publication date: 2019-02-07
Also published as: CN110997025A; JP2020530804A; KR101840254B1

Abstract

The present invention relates to a composition for preparing artificial skin, containing a fibrous polymer, and a method for preparing artificial skin by using the same, the composition comprising: a first composition comprising a fibrous polymer, a solvent and a first compound, which comprises a vinyl terminal group and a backbone composed of a repeating unit comprising a silicon element; and a second composition comprising a catalyst, a solvent and a second compound, which comprises a hydrogen terminal group and a backbone composed of a repeating unit comprising a silicon element.

Description

Compositions for making artificial skin containing fibrous polymer and method for manufacturing artificial skin using the same

More particularly, the present invention relates to a composition for forming a synthetic skin within a short time at a low temperature and a method for producing a synthetic skin using the composition.

At present, artificial skin related technology is attracting great interest in various industrial fields such as biopharmaceuticals, electric / electronic fields, and robotics fields. Especially, it is difficult to estimate the application to medical and cosmetic fields such as therapeutic agents for skin damaged by burns and ulcers, medicines and cosmetics, and functional products that give elasticity to aged skin.

Prior art literature

(Patent Document 1) Korean Patent No. 10-0861980

(Patent Document 2) Korean Patent Laid-Open No. 10-2009-0119878

An object of the present invention is to provide a composition capable of forming artificial skin within a short time at a low temperature when applied to skin, and a method for producing artificial skin using the composition.

It is another object of the present invention to provide a composition capable of forming artificial skin having excellent physical properties such as tensile strength and a method for producing artificial skin using the same.

The object of the present invention is not limited to the above-mentioned object. The objects of the present invention will become more apparent from the following description, which will be realized by means of the appended claims and their combinations.

The composition for making artificial skin according to an embodiment of the present invention comprises a first composition comprising a first polymer comprising a skeleton composed of repeating units represented by formula (1) and a vinyl end group, a fibrous polymer, and a solvent; And a second composition comprising a skeleton composed of repeating units represented by formula (1) and a hydrogen terminal group, a catalyst and a solvent.

[Chemical Formula 1]

The first composition may include 15 wt% to 30 wt% of the first compound, 1 wt% to 10 wt% of the fibrous polymer, and the remaining amount of the solvent.

The second composition may comprise from 15 wt% to 30 wt% of the second compound, from 0.01 wt% to 1.00 wt% of catalyst, and balance of solvent.

The first compound may be represented by the following formula (2).

(2)

Here, n is 0 to 10,000.

The second compound may be represented by the following formula (3).

(3)

Here, n is 0 to 10,000.

The fibrous polymer may be selected from the group consisting of cellulose, carboxymethyl cellulose, pectin, dextrose, fibrin, ethyl cellulose, hydroxypropylmethyl cellulose, Hydroxypropyl cellulose, and combinations thereof. &Lt; Desc / Clms Page number 7 >

The fibrous polymer may have a length of 100 nm to 500 nm.

The catalyst may be selected from the group consisting of a platinum (Pt) catalyst, a rubidium catalyst, and combinations thereof.

The first and second compositions further comprise additives selected from the group consisting of chelating agents, emulsifiers, pH adjusting agents, preservatives, skin conditioning agents, wetting agents, fragrances, and combinations thereof can do.

The method of manufacturing a synthetic skin according to an embodiment of the present invention includes the steps of providing the first composition to the skin, providing the second composition to be mixed with the first composition, and applying heat to the first composition, And reacting the compound with the second compound.

The method of manufacturing a synthetic skin according to an embodiment of the present invention comprises the steps of: providing the second composition to the skin; providing the first composition to be mixed with the second composition; And reacting the compound with the second compound.

The first composition and the second composition may be applied to the skin or the skin in contact with the skin.

The first compound and the second compound are crosslinked through a hydrosilylation reaction to form a thin film of artificial skin, and the fibrous polymer can be distributed in the thin film of the artificial skin.

The heat can be applied by heat of the skin.

According to one embodiment of the present invention, artificial skin can be formed within a time of 200 seconds or less when heat of 25 ° C to 30 ° C is applied.

According to an embodiment of the present invention, artificial skin can be formed within a time of less than 180 seconds when heat of 30 ° C to 35 ° C is applied.

According to one embodiment of the present invention, artificial skin can be formed within a time of less than 160 seconds when heat of 35 ° C to 40 ° C is applied.

The artificial skin composition can be formed within a short time at a low temperature by using the artificial skin composition according to an embodiment of the present invention.

Also, when the composition for artificial skin preparation according to an embodiment of the present invention is used, artificial skin having excellent physical properties such as tensile strength can be formed.

The effects of the present invention are not limited to the effects mentioned above. It should be understood that the effects of the present invention include all reasonably possible effects in the following description.

FIG. 1 shows the results of measuring tensile strength of artificial skin formed according to an embodiment of the present invention.

BRIEF DESCRIPTION OF THE DRAWINGS The above and other objects, features, and advantages of the present invention will become more readily apparent from the following description of preferred embodiments with reference to the accompanying drawings. However, the present invention is not limited to the embodiments described herein but may be embodied in other forms. Rather, the embodiments disclosed herein are provided so that this disclosure will be thorough and complete, and will fully convey the concept of the invention to those skilled in the art.

Like reference numerals are used for like elements in describing each drawing. In the accompanying drawings, the dimensions of the structures are shown enlarged from the actual for the sake of clarity of the present invention. The terms first, second, etc. may be used to describe various components, but the components should not be limited by the terms. The terms are used only for the purpose of distinguishing one component from another. For example, without departing from the scope of the present invention, the first component may be referred to as a second component, and similarly, the second component may also be referred to as a first component. The singular expressions include plural expressions unless the context clearly dictates otherwise.

In the present application, the terms "comprises" or "having" and the like are used to specify that there is a feature, a number, a step, an operation, an element, a component or a combination thereof described in the specification, But do not preclude the presence or addition of one or more other features, integers, steps, operations, components, parts, or combinations thereof. Also, where a portion such as a layer, film, region, plate, or the like is referred to as being "on" another portion, this includes not only the case where it is "directly on" another portion, but also the case where there is another portion in between. On the contrary, when a part such as a layer, film, region, plate or the like is referred to as being "under" another part, it includes not only the case where it is "directly underneath" another part but also another part in the middle.

In the present specification, the term "artificial skin" refers to a thin film that is artificially made as close as possible to actual skin texture, feel, texture, and the like, which physical and physical properties of actual skin are satisfied equally or similarly. However, the term " thin film " refers not to a thin film prepared by culturing a living tissue, a cell, or the like, but a thin film made of a material such as a polymer.

The term " composition for making artificial skin " means a composition capable of forming the artificial skin when applied to the body.

A composition for making artificial skin according to an embodiment of the present invention comprises a first composition comprising a first compound, a fibrous polymer and a solvent, and a second compound comprising a second compound, a catalyst and a solvent. The first and second compositions may further comprise additives selected from the group consisting of a chelating agent, an emulsifier, a pH adjuster, a preservative, a skin conditioning agent, a wetting agent, a flavoring, .

The first composition comprises a first compound comprising a skeleton composed of repeating units represented by the following formula (1) and a vinyl end group, a fibrous polymer, and a solvent.

[Chemical Formula 1]

In the above formula (1), n is a molar ratio of 1 to 10,000.

The first compound forms a thin film of artificial skin by performing a special crosslinking reaction with the second compound to be described later. Specifically, the first compound may be a compound represented by the following formula (2).

(2)

Here, n may be 0 to 10,000, or 0 to 8,000, or 0 to 6,000.

In particular, the viscosity of the first compound may range from 0.1 cP to 5,000,000 cP.

The fibrous polymer improves the physical properties such as the tensile strength of the artificial skin and shortens the formation time of the artificial skin.

The fibrous polymer may be selected from the group consisting of cellulose, carboxymethyl cellulose, pectin, dextrose, fibrin, ethyl cellulose, hydroxypropylmethyl cellulose, Hydroxypropyl cellulose, and a combination thereof. It may be preferable to use a natural polymer selected from the group consisting of hydroxypropyl cellulose and a combination thereof.

The fibrous polymer may be preferably of nano size. For example, those having a diameter of 0.1 nm to 1,000 nm and a length of 100 nm to 500 nm. The diameter and the length of the fibrous polymer should fall within the above-mentioned numerical range, so that a thin film of artificial skin having improved durability can be formed. If the diameter and the length are small, the degree of improvement of the physical properties of the artificial skin may be insignificant. If the diameter and length are too large, the crosslinking of the first compound and the second compound may not be properly performed and the thin film may not be formed.

Specifically, it is most preferable to use a nano-sized fibrous polymer composed of cellulose, which is a non-toxic material having excellent biocompatibility. In particular, it is effective to reduce wound pain and bacterial infection, Because it has efficacy, it can give functionality to artificial skin.

The second composition includes a second compound comprising a skeleton composed of the repeating unit represented by the formula (1) and a hydrogen terminal group, a catalyst and a solvent.

The second compound is combined with the first compound through a crosslinking reaction to form a thin film of artificial skin. Specifically, the second compound may be a compound represented by the following formula (3).

(3)

Here, n may be 0 to 10,000.

In particular, the viscosity of the second compound may be between 0.1 cP and 5,000,000 cP.

The catalyst accelerates crosslinking of the first compound and the second compound so that artificial skin can be formed within a short time even at a low temperature.

The catalyst may be selected from the group consisting of a platinum (Pt) catalyst, a rubidium (Rb) catalyst, and combinations thereof. However, it is preferable to use a platinum catalyst, because the effect of increasing the reaction rate is greater when the platinum catalyst is used.

The solvent is not particularly limited as long as it can dilute the first compound, the second polymer, the fibrous polymer, and the catalyst, and for example, water, alcohol, glycerol, and combinations thereof can be used. The first composition comprises 15 wt% to 30 wt% of the first compound, 1 wt% to 10 wt% of the fibrous polymer, and the remaining amount of the solvent.

If the content of the fibrous polymer is less than 1% by weight, the amount of the fibrous polymer to be added may be too small to improve the physical properties such as tensile strength. On the other hand, if the content exceeds 10% by weight, the flexibility of the synthetic skin may decrease, .

The second composition comprises 15 wt% to 30 wt% of the second compound, 0.01 wt% to 1.00 wt% of catalyst, and the balance solvent .

If the content of the second compound is less than 15% by weight, the amount of the second compound capable of crosslinking with the first compound is small, so that it may not be formed in the thin film of the artificial skin. If the content of the catalyst is less than 0.01 wt%, the reaction of the first compound and the second compound may not occur. If the content of the catalyst is more than 1.00 wt%, the effect of increasing the reaction rate may be insignificant.

The composition for making artificial skin according to an embodiment of the present invention may be selected from the group consisting of a chelating agent, an emulsifier, a pH adjusting agent, a preservative, a skin conditioning agent, a wetting agent and a perfume, and combinations thereof And the additive may be contained in only one of the first composition and the second composition, and may be contained in both the first composition and the second composition, respectively.

The chelating agent may block the activity of metal ions that may be incorporated into the first composition and / or the second composition, including but not limited to ethylenediamine tetraacetate (EDTA) , 0.02 wt% to 0.1 wt%.

The emulsifier may be a mixture of a first composition and a second composition such that the first composition and the second composition may be uniformly mixed. The emulsifier may be, for example, TR-1 (Acrylate / C10-30 Alkyl Acrylate Crosspolymer) . &Lt; / RTI >

The pH adjusting agent may be adjusted to adjust the pH of the first and second compositions so as to be suitable for the cross-linking reaction. For example, the pH adjusting agent may include tromethamine and may include 0.15 wt% to 0.5 wt% .

The preservative may be a composition for long-term storage of the first composition and / or the second composition, and may include, but is not limited to, phenoxyethanol, and may include 0.4 wt% to 1 wt%.

The skin conditioning agent is a composition for restoring the flexibility of the skin, and is not limited thereto. Ethylhexyl glycerin may be used, and the skin conditioning agent may include 0.1% to 0.5% by weight.

The wetting agent is a composition for increasing the moisture retention of the outer skin layer. The wetting agent may be, but is not limited to, glycerin, and may include 5.0 wt% to 8.0 wt%.

The perfume may be used in various kinds depending on the purpose, and may include from 0.2 wt% to 1 wt%.

The method of manufacturing a synthetic skin according to an embodiment of the present invention includes the steps of providing the first composition or the second composition to the skin, providing the second composition or the first composition to be mixed with the first composition or the second composition And reacting the first compound with the second compound by applying heat to the mixture.

For convenience of explanation, the method of providing the first composition to the skin and then providing the second composition will be mainly described. However, it should be understood that the present invention is not limited thereto, and that the first composition is provided first and then the first composition is also provided as an embodiment of the present invention.

First, providing the first composition to the skin may mean applying the first composition directly to the skin, or applying the first composition to another substrate such as a sheet in contact with the skin. However, it is also possible to provide a method of adhering a substrate, such as a sheet impregnated with the first composition, to the skin, away from the application method.

The step of providing the second composition to be mixed with the first composition may mean that the second composition is applied to another substrate such as a sheet or the sheet in contact with the skin or the skin to which the first composition is applied. However, the second composition may also be provided in such a manner that the substrate such as the sheet impregnated with the first composition is adhered to the skin by deviating from the application method. It is not always necessary to apply the second composition to the skin to which the first composition is applied, but it is also possible to apply the second composition to the peripheral portion of the surface to which the first composition is applied and then mix.

After mixing the first composition and the second composition as described above, heat is applied to the mixture to react the first compound and the second compound to form a synthetic skin.

Specifically, the mixture contains a first compound, a second compound and a catalyst. When heat is applied to the mixture, a hydrosilylation reaction occurs as shown in Formula 4 below, and the first compound and the second compound are cross- Is formed. That is, hydrogen silylation reaction occurs between the vinyl end group of the first compound and the hydrogen end group of the second compound, thereby crosslinking the first compound and the second compound.

[Chemical Formula 4]

Since the mixture contains a fibrous polymer, the first compound and the second compound are crosslinked by the chemical formula 4, and when the thin film of artificial skin is formed, the fibrous polymer is distributed in the thin film and the tensile strength of the artificial skin Physical properties are improved.

The heat application method for causing the hydrogen saccharification reaction is not particularly limited. For example, heat applied to the skin to which the first composition and the second composition are applied may be applied.

The artificial skin according to an embodiment of the present invention can be formed within a short time even at a low temperature such as a temperature range of skin, which can be clearly understood by the following embodiments.

Hereinafter, the present invention will be described in more detail with reference to examples and comparative examples. However, these examples are for illustrating the present invention and the scope of the present invention is not limited thereto.

제1 조성물의 준비Preparation of first composition

The first composition was prepared with the composition shown in Table 1 below. Specifically, the first compound, the fibrous polymer, and the additive were all put into a solvent and stirred until they were completely dissolved.

제2 조성물의 준비Preparation of second composition

A second composition was prepared with the composition shown in Table 1 below. Specifically, the second compound, the catalyst and the additive were all put into a solvent and stirred until they were completely dissolved.

Note 1) Table 1 EDTA 2Na, Daebong LS

Note 2) Vinyl dimethicone, molecular weight 10,000 g / mol, viscosity 160,000 cP, KCC,

Note 3) Hydrogen dimethicone, molecular weight 10,000 g / mol, viscosity 160,000 cP, KCC

Note 4) Platinum catalyst

Note 5) TR-1, Lubrizol

Note 6) Tromethamine, aT lab

Note 7) Phenoxyethanol, Galaxy

Note 8) Ethylhexylglycerin, Schuelke & Mayr

Note 9) Glycerin, ACID CHEM

Note 10) Cellulose nanofibers with a diameter of about 10 nm and a length of about 10 nm,

인조피부의 형성Formation of artificial skin

The first composition was applied onto a substrate maintained at a constant temperature. The second composition was applied to the side to which the first composition was applied. The first composition and the second composition were rubbed at a constant speed so as to be uniformly mixed, and then heat of the temperature shown in Table 2 was added to the mixture to form a synthetic skin. The time taken until the formation of artificial skin was confirmed with the naked eye was measured.

Referring to Table 2, when artificial skin is formed through crosslinking of the first compound and the second compound, artificial skin is formed in a very short time of about 220 seconds or less at a low temperature condition of 25 ° C to 40 ° C .

In particular, in Examples 1 to 5 including 1 wt% to 10 wt% of the fibrous polymer as in the example of the present invention, it is understood that the time required for forming the artificial skin is further shortened. Specifically, when heat of 25 ° C to 30 ° C is applied, heat is applied for 200 seconds or less, when heat of 30 ° C to 35 ° C is applied for less than 180 seconds, and when heat of 35 ° C to 40 ° C is applied, It can be confirmed that the skin is formed.

박막강도의 측정Measurement of Thin Film Strength

The tensile strength of the artificial skin formed by the above-mentioned method was measured. Specifically, using a tensile compression tester (Universal Testing Machine, Instron, 4485 TIC960203-97B1A) under the conditions of 0 ° C, 20 ° C, 30 ° C, 40 ° C, 50 ° C, 60 ° C and 80 ° C, tensile strength Were measured . The results are shown in Fig.

Referring to FIG. 1, Examples 1 to 5 containing 1 wt% to 10 wt% of a fibrous polymer according to an embodiment of the present invention have significantly higher tensile strengths than Comparative Example 1 that does not include a fibrous polymer It can be seen that it has durability suitable for use as an artificial skin.

While the present invention has been particularly shown and described with reference to exemplary embodiments thereof, it is to be understood that the scope of the present invention is not limited to the disclosed exemplary embodiments. Various modifications and improvements of those skilled in the art are also within the scope of the present invention.

Claims

A first composition comprising a first compound comprising a skeleton composed of repeating units represented by formula (1) and a vinyl end group, a fibrous polymer, and a solvent; And

And a second composition comprising a second compound comprising a skeleton composed of repeating units represented by formula (1) and a hydrogen terminal group, a catalyst and a solvent,

The fibrous polymer may be selected from the group consisting of cellulose, carboxymethyl cellulose, pectin, dextrose, fibrin, ethyl cellulose, hydroxypropylmethyl cellulose, Hydroxypropyl cellulose, and a combination thereof, and has a length of 100 nm to 500 nm,

Wherein the first composition and the second composition are mixed.

[Chemical Formula 1]
The method according to claim 1,

Wherein the first composition comprises 15 wt% to 30 wt% of the first compound, 1 wt% to 10 wt% of the fibrous polymer, and the remaining amount of the solvent.
The method according to claim 1,

Wherein the second composition comprises 15 wt% to 30 wt% of the second compound, 0.01 wt% to 1.00 wt% of catalyst, and the balance solvent.
The method according to claim 1,

Wherein the first compound is represented by the following formula (2).

(2)

Here, n is 0 to 10,000.
The method according to claim 1,

Wherein the second compound is represented by the following formula (3).

(3)

Here, n is 0 to 10,000.
The method according to claim 1,

Wherein the catalyst is selected from the group consisting of a platinum (Pt) catalyst, a rubidium (Rb) catalyst, and combinations thereof.
The method according to claim 1,

The first and second compositions further comprise additives selected from the group consisting of chelating agents, emulsifiers, pH adjusting agents, preservatives, skin conditioning agents, wetting agents, fragrances, and combinations thereof Wherein said composition is a composition for the manufacture of artificial skin.
Use of the composition of claim 1,

Providing a first composition;

Providing the second composition to be mixed with the first composition; And

And applying heat to the mixture to react the first compound with the second compound.
Use of the composition of claim 1,

Providing a second composition;

Providing the first composition to be mixed with the second composition; And

And applying heat to the mixture to react the first compound with the second compound.
10. The method according to claim 8 or 9,

Wherein the first compound and the second compound are crosslinked through a hydrosilylation reaction to form a thin film of artificial skin,

Wherein the fibrous polymer is distributed in the thin film of the artificial skin.
10. The method according to claim 8 or 9,

Wherein artificial skin is formed within a time of 200 seconds or less when heat of 25 to 30 占 폚 is applied.
10. The method according to claim 8 or 9,

Wherein artificial skin is formed within a time period of less than 180 seconds when heat of 30 占 폚 to 35 占 폚 is applied.
10. The method according to claim 8 or 9,

Wherein artificial skin is formed within a time period of less than 160 seconds when heat of 35 DEG C to 40 DEG C is applied.