KR20180113778A - Pressure sensitive adhesive composition and film dressing material comprising cured product thereof - Google Patents

Abstract

The present invention relates to a pressure-sensitive adhesive composition comprising: alkyl (meth)acrylate ester monomers; alkoxy (meth)acrylate ester monomers; and (meth)acrylate ester monomer containing polar functional groups. The content of the alkyl (meth)acrylate ester monomer is 50 wt% or more and 75 wt% or less based on the pressure-sensitive adhesive composition, the content of the alkoxy (meth)acrylate ester monomer is 10 wt% % or more and 27 wt% or less based on the pressure-sensitive adhesive composition, and the content of the (meth)acrylic acid ester monomer containing the polar functional group is 5 wt% or more and 30 wt% or less based on the pressure-sensitive adhesive composition.

Description

TECHNICAL FIELD [0001] The present invention relates to a pressure-sensitive adhesive composition and a film dressing material containing the same,

The present invention relates to a pressure-sensitive adhesive composition and a film dressing material comprising the cured product.

Wound healing with dressing should be performed in order to speed up the healing of the wound on the skin and minimize the secondary side effects. Since 1962 Winter was announced that wound healing under humid conditions had an excellent effect, many results have been reported to verify this. As a method of wound healing, a gauze method of a conventional drying environment is used, but in recent years, a dressing method for creating a wet environment has been used.

Among various dressing methods, film dressing is used for secondary layer dressing which is used for partial skin damage with few exudates, can prevent the pressure ulcer due to friction, and fixes the dressing contacting the wound base.

The film dressing can prevent the external damage of the wound and prevent the occurrence of dry skin, thereby creating a wet healing environment. However, there is a problem in the treatment of a wound site having a large amount of exudate due to insufficient absorption power.

Adhesion to skin, fixability and breathability correspond to important physical properties required for film dressing. Particularly, when the air permeability is low, there is a problem that the dressing is desorbed due to the wetting between the skin and the dressing, causing the itch in the wound area.

Therefore, there is a need for research on film dressing which can simultaneously enhance adhesion to skin, fixation property and breathability, and minimize irritation to skin.

KR 10-2016-0077754 A

The present specification intends to provide a film dressing material comprising a pressure-sensitive adhesive composition and a cured product thereof.

One embodiment of the present invention is to provide a pressure-sensitive adhesive composition.

Specifically, one embodiment of the present invention relates to a pressure-sensitive adhesive composition comprising an alkyl (meth) acrylate-based monomer; Alkoxy (meth) acrylate ester monomers; Wherein the content of the alkyl (meth) acrylate monomer is 50 wt% or more and 75 wt% or less based on the pressure-sensitive adhesive composition, and the content of the alkoxy (meth) acrylate monomer (Meth) acrylic ester monomer is 10% by weight or more and 27% by weight or less based on the pressure-sensitive adhesive composition, and the content of the (meth) acrylate monomer containing the polar functional group is 5 By weight to 30% by weight or less based on the total weight of the pressure-sensitive adhesive composition.

Another embodiment of the present invention is a method of manufacturing a semiconductor device, comprising: a substrate; And a pressure-sensitive adhesive layer formed on the substrate and including a cured product of the pressure-sensitive adhesive composition.

The pressure-sensitive adhesive composition according to one embodiment of the present invention can provide a film dressing material having a high water vapor transmission rate.

The film dressing material according to one embodiment of the present invention has an advantage that it is possible to prevent desorption due to wetting between the skin and the dressing material due to a high water vapor permeability and to prevent itching of the skin.

When a member is referred to herein as being "on " another member, it includes not only a member in contact with another member but also another member between the two members.

Whenever a component is referred to as "comprising ", it is understood that it may include other components as well, without departing from the other components unless specifically stated otherwise.

Hereinafter, the present invention will be described in more detail.

One embodiment of the present invention is a pressure-sensitive adhesive composition comprising: an alkyl (meth) acrylate-based monomer; Alkoxy (meth) acrylate ester monomers; Wherein the content of the alkyl (meth) acrylate monomer is 50 wt% or more and 75 wt% or less based on the pressure-sensitive adhesive composition, and the content of the alkoxy (meth) acrylate monomer (Meth) acrylic ester monomer is 10% by weight or more and 27% by weight or less based on the pressure-sensitive adhesive composition, and the content of the (meth) acrylate monomer containing the polar functional group is 5 By weight to 30% by weight or less based on the weight of the pressure-sensitive adhesive composition.

According to one embodiment of the present invention, the alkyl (meth) acrylate-based monomer may mean a (meth) acrylic acid ester-based monomer having an alkyl group having 1 to 14 carbon atoms in a straight chain or branched chain. By having an alkyl group having a carbon number within the above range, it is possible to prevent the excessive long chain of the alkyl group contained in the monomer, improve the cohesion of the pressure-sensitive adhesive composition, and facilitate the control of the glass transition temperature (Tg) and the tackiness.

According to one embodiment of the present invention, the alkyl (meth) acrylate monomer is at least one monomer selected from the group consisting of methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, (meth) acrylate, 2-ethylhexyl (meth) acrylate, 2-ethylbutyl (meth) acrylate, (Meth) acrylate, n-octyl (meth) acrylate, isooctyl (meth) acrylate, isobornyl (meth) acrylate and isononyl have.

According to one embodiment of the present invention, the alkoxy (meth) acrylate monomer is selected from the group consisting of 2-ethoxyethoxyethyl acrylate, 2-ethoxyethoxyethyl methacrylate, methoxyethyl acrylate and methoxyethyl methacrylate Acrylate, and the like.

According to one embodiment of the present invention, the (meth) acrylic acid ester monomer containing the polar functional group is at least one monomer selected from the group consisting of a hydroxy group-containing (meth) acrylate ester monomer, a carboxyl group-containing (meth) Based monomers and ester-based monomers.

According to one embodiment of the present invention, the hydroxy group-containing (meth) acrylate monomer is at least one selected from the group consisting of 2-hydroxyethyl (meth) acrylate, 2- hydroxypropyl (meth) (Meth) acrylate, 6-hydroxyhexyl (meth) acrylate, 8-hydroxyoctyl (meth) acrylate, 2-hydroxyethylene glycol (meth) acrylate and 2-hydroxypropylene glycol , And the like.

According to one embodiment of the present invention, the carboxyl group-containing (meth) acrylate monomer is at least one selected from the group consisting of acrylic acid, methacrylic acid, 2- (meth) acryloyloxyacetic acid, 3- - (meth) acryloyloxybutyric acid, acrylic acid dimer, itaconic acid, and maleic acid.

According to one embodiment of the present invention, the nitrogen-containing (meth) acrylate-based monomer is at least one selected from the group consisting of hydroxyethyl (meth) acrylamide, N, N-dialkyl (meth) acrylamide, (Meth) acrylamide, N-hydroxyalkyl (meth) acrylamide, N-hydroxyalkyl (meth) acrylamide, N-hydroxyalkyl - (2-aminoethyl) acrylamide hydrochloride, N- (3-aminopropyl) methacrylamide hydrochloride, N- (t-butoxycarbonyl- aminopropyl) methacrylamide, N, (Meth) acrylamide, N-vinylpyrrolidone, N-vinylcaprolactam, and (meth) acryloylmorpholine.

According to an embodiment of the present invention, the content of the alkyl (meth) acrylate monomer may be 50% by weight or more and 75% by weight or less, specifically 60% by weight or more and 70% by weight or less based on the pressure-sensitive adhesive composition. By including the alkyl (meth) acrylate-based monomer in the above range, the film dressing material can ensure high wettability due to a low glass transition temperature and can adhere to the wound site due to proper adhesive force and then peel off It can alleviate the pain of the time.

According to one embodiment of the present invention, the content of the alkoxy (meth) acrylate monomer may be 10 wt% or more and 27 wt% or less, specifically 15 wt% or more and 25 wt% or less based on the pressure-sensitive adhesive composition. By including the alkoxy (meth) acrylate-based monomer in the above-mentioned content range, the pressure-sensitive adhesive layer containing the cured product of the pressure-sensitive adhesive composition can realize high moisture permeability due to free rotation of the ether group contained therein.

According to one embodiment of the present invention, the content of the (meth) acrylic ester monomer containing a polar functional group is 5 wt% or more and 30 wt% or less, specifically 7 wt% or more and 25 wt% or less based on the pressure- More specifically, it may be 10 wt% or more and 20 wt% or less. By including the (meth) acrylate-based monomer containing the polar functional group in the above-mentioned content range, the film dressing material can have appropriate fixing force and adhesion to the skin.

According to one embodiment of the present invention, the pressure-sensitive adhesive composition may have a weight average molecular weight of 500,000 g / mol to 2,500,000 g / mol, specifically 1,000,000 g / mol to 2,000,000 g / mol. In the range of the weight average molecular weight within the above range, the pressure-sensitive adhesive composition can secure sufficient cohesion force between the acrylic monomers, and the film dressing material containing the cured product of the pressure-sensitive adhesive composition can prevent residue on the skin.

According to one embodiment of the present invention, the gel content of the pressure-sensitive adhesive composition may be 30% or more and 70% or less, specifically 35% or more and 60% or less. The film dressing can secure an appropriate cohesive force within a gel content range of the pressure-sensitive adhesive composition, and can be stably fixed without lifting the edges of the dressing material even when the film dressing material is adhered to the skin. After the film dressing material is removed, May not remain.

Another embodiment of the present invention is a method of manufacturing a semiconductor device, comprising: a substrate; And a pressure-sensitive adhesive layer formed on the substrate and including a cured product of the pressure-sensitive adhesive composition.

According to one embodiment of the present invention, the adhesive energy of the film dressing material may be 100 g · mm or more and 500 g · mm or less, specifically 200 g · mm or more and 300 g · mm or less. It is possible to provide a film dressing material having excellent wettability and sufficient peeling strength within the above range.

In the present specification, the adhesive energy of the film dressing material can mean the area below the graph in the graph of the adhesive force with time, as the ability of the adherend and the dressing material to adhere thereto.

According to one embodiment of the present invention, the substrate may be at least one selected from the group consisting of thermoplastic polyurethane, polyvinyl chloride, polyethylene, polypropylene, polybutene and polyvinyl alcohol, but the type is not limited thereto Any material that can be selected as a material having a waterproof function in the art can be freely applied.

According to one embodiment of the present invention, the thickness of the base material may be 5 占 퐉 or more and 35 占 퐉 or less, specifically 10 占 퐉 or more and 15 占 퐉 or less. It is possible to prevent the inconvenience of the user in adhering the skin of the film dressing material within the thickness range of the substrate and to easily operate the film dressing material.

According to an embodiment of the present invention, the thickness of the adhesive layer may be 5 占 퐉 or more and 30 占 퐉 or less. In the range of the above thickness, the film dressing material can secure an appropriate adhesive force that is easy to attach and detach to the wound site.

According to one embodiment of the present invention, the water vapor transmission rate of the film dressing material may be 3,000 g / m ² · day to 5,000 g / m ² · day at a temperature of 40 ° C. and a relative humidity of 20%. By having the water vapor transmission rate in the above range, the film dressing material can easily absorb the exudate at the wound site.

According to one embodiment of the present invention, the peeling force of the film dressing material may be 600 gf / 20 mm or more and 800 gf / 20 mm or less, specifically 650 gf / 20 mm or more and 760 gf / 20 mm or less. By having the peeling force in the above range, the film dressing material can be easily detached from the wound site.

In this specification, the peeling force of the film dressing material may mean a vertical tensile force per unit area required to separate the adherend and the dressing material.

According to an embodiment of the present invention, the adhesive force of the film dressing material may be 40 gf or more and 70 gf or less, specifically 45 gf or more and 65 gf or less. By having the adhesive force in the above range, the film dressing material can be easily attached to the wound site and can have a high exuding capacity.

In the present specification, the adhesive force of the film dressing material may mean a vertical tensile force for adhering the adherend and the dressing material.

BEST MODE FOR CARRYING OUT THE INVENTION Hereinafter, the present invention will be described in detail with reference to examples. However, the embodiments according to the present invention can be modified into various other forms, and the scope of the present invention is not construed as being limited to the embodiments described below. Embodiments of the present disclosure are provided to enable those skilled in the art to more fully understand the present invention.

Example 1

(2-EHA), 25 wt% of 2-methoxyethyl acrylate (2-MEA) and 10 wt% of 2-hydroxyethyl acrylate Acrylate (2-HEA) was prepared.

The pressure-sensitive adhesive composition was dried at a temperature of 110 DEG C for 3 minutes, and then coated on a release film.

The pressure-sensitive adhesive composition coated on the release film was laminated to a polyurethane base material having a thickness of 10 탆. The lapped pressure-sensitive adhesive composition was aged in an atmosphere at 50 캜 for 24 hours to prepare a film dressing material containing an adhesive layer containing a cured product of the pressure-sensitive adhesive composition.

Example 2

A film dressing material was produced in the same manner as in Example 1, except that it contained 68 wt% of 2-ethylhexyl acrylate and 7 wt% of hydroxyethyl acrylamide (HEAA) instead of 2-hydroxyethyl acrylate Respectively.

Example 3

Except for containing 15 wt% of 2-methoxyethyl acrylate (2-MEA) and 20 wt% of 2-hydroxyethyl acrylate (2-HEA) .

Comparative Example 1

A film dressing material was prepared in the same manner as in Example 1, except that 25% by weight of vinyl acetate (VA) was used instead of 2-methoxyethyl acrylate.

Comparative Example 2

(2-methoxyethyl acrylate) (2-MEA) and 5% by weight of 2-hydroxyethyl acrylate (2-HEA) were prepared in the same manner as in Example 1, except that the film- .

Comparative Example 3

A film dressing material was prepared in the same manner as in Example 1, except that it contained 32% by weight of 2-methoxyethyl acrylate (2-MEA) and 3% by weight of hydroxyethyl acrylamide (HEAA).

The components and the contents of Examples 1 to 3 and Comparative Examples 1 to 3 are shown in Table 1 below.

2-EHA (wt%) 2-MEA (% by weight) VA (% by weight) 2-HEA (wt%) HEAA (wt%) Example 1 65 25 - 10 - Example 2 68 25 - - 7 Example 3 65 15 - 20 - Comparative Example 1 65 - 25 10 - Comparative Example 2 65 30 - 5 - Comparative Example 3 65 32 - - 3

Experimental Example

1. Moisture Vapor Transmission Rate (MVTR)

It was measured by the water method according to the conditions of ASTM E96. Specifically, each film dressing material was cut to prepare a circular sample having a diameter of 65 mm. The initial weight, which is the weight of each sample before the sample was placed in the constant temperature and humidity chamber, was measured, And 20% relative humidity for 24 hours, and the vapor permeability was calculated by the following formula (1).

[Formula 1]

Water vapor permeability (g / m ² · day) = (initial weight - late weight) / area

2. Peeling force measurement

The prepared film dressing prepared according to Examples 1 to 3 and Comparative Examples 1 to 3 was cut to a width of 25 mm and a length of 180 mm to prepare specimens. One surface of the specimen was fixed to stainless steel (SUS) by reciprocating 5 times with a 2 kg roller Respectively.

The specimen attached to the stainless steel was peeled off at a peeling speed of 300 mm / min using a peeling force measuring device at a temperature of 25 minutes at a temperature of 60 minutes, and the peeling force was measured at a peeling angle of 180 degrees.

3. Adhesion measurement and adhesive energy measurement

A Teflon plate with perforations about 300 mm in diameter was prepared.

On one side of the Teflon plate, the film dressing materials prepared according to Examples 1 to 3 and Comparative Examples 1 to 3 were attached.

The SUS probe was peeled off at a speed of 6 mm / min toward the adhesive layer side of the film dressing material, and the adhesive strength was measured.

The adhesive energy was measured by the area of the graph plotted against the time of adhesion.

4. Measurement of gel content

Gel content (% by weight) = B / A x 100

In the above, A represents the mass of the pressure-sensitive adhesive composition of Examples 1 to 3 and Comparative Examples 1 to 3, and B represents the mass of the pressure-sensitive adhesive composition after immersing the pressure-sensitive adhesive composition at 60 for 24 hours in ethyl acetate (200 mesh ), And shows the dry mass of the insoluble component of the pressure-sensitive adhesive composition that has not passed through the net.

<Evaluation>

The evaluation results of the physical property measurement of the film dressing material produced according to Examples 1 to 3 and Comparative Examples 1 to 3 are shown in Table 2 below.

unit Example 1 Example 2 Example 3 Comparative Example 1 Comparative Example 2 Comparative Example 3 MVTR g / m ² · day 3,862 3,023 3,966 2,112 1,988 1,698 Peel force gf / 20mm 689 760 702 684 380 708 adhesiveness gf 55 48 65 50 48 86 Adhesive energy g · mm 248 211 280 143 102 228 Gel content % 55 39 60 69 25 0

According to Table 2, the peel strength, adhesive strength, adhesive energy and gel content of the film dressing materials according to Examples 1 to 3 were not greatly different from those of the film dressing materials according to Comparative Examples 1 to 3, 1 &lt; / RTI &gt; to 3 &lt; RTI ID = 0.0 &gt;. &Lt; / RTI &gt; As a result, it has been confirmed that the water vapor permeability can be increased by containing the alkoxy (meth) acrylate monomer and the content of each component in the content range of the present invention.

Claims (11)

In the pressure-sensitive adhesive composition,
Alkyl (meth) acrylate-based monomers;
Alkoxy (meth) acrylate ester monomers; And
(Meth) acrylic acid ester-based monomer containing a polar functional group,
The content of the alkyl (meth) acrylate monomer is 50% by weight or more and 75% by weight or less based on the pressure-sensitive adhesive composition,
The content of the alkoxy (meth) acrylate monomer is 10% by weight or more and 27% by weight or less based on the pressure-sensitive adhesive composition,
Wherein the content of the (meth) acrylic acid ester-based monomer containing the polar functional group is 5% by weight or more and 30% by weight or less based on the pressure-sensitive adhesive composition.
The method according to claim 1,
Wherein the pressure-sensitive adhesive composition has a weight-average molecular weight of 500,000 g / mol or more and 2,500,000 g / mol or less.
The method according to claim 1,
Wherein the pressure-sensitive adhesive composition has a gel content of 30% or more and 70% or less.
materials; And
And a pressure-sensitive adhesive layer formed on the substrate, wherein the pressure-sensitive adhesive layer comprises a cured product of the pressure-sensitive adhesive composition according to claim 1.
5. The method of claim 4,
Wherein an adhesive energy of the film dressing material is 100 g · mm or more and 500 g · mm or less.
5. The method of claim 4,
Wherein the base material is at least one selected from the group consisting of thermoplastic polyurethane, polyvinyl chloride, polyethylene, polypropylene, polybutene, and polyvinyl alcohol.
5. The method of claim 4,
Wherein the thickness of the base material is 5 占 퐉 or more and 35 占 퐉 or less.
5. The method of claim 4,
Wherein the thickness of the adhesive layer is 5 占 퐉 or more and 30 占 퐉 or less.
5. The method of claim 4,
Wherein the film dressing material has a vapor permeability of not less than 3,000 g / m ² · day and not more than 5,000 g / m ² · day under conditions of a temperature of 40 ° C. and a relative humidity of 20%.
5. The method of claim 4,
Wherein the film dressing material has a peeling force of 600 gf / 20 mm or more and 800 gf / 20 mm or less.
5. The method of claim 4,
Wherein the film dressing material has an adhesive force of 40 gf or more and 70 gf or less.