KR102101773B1 - Gel nail polish composition comprising acrylate containing acetal group, photoradical initiator and photoacid generator as effective component and uses thereof - Google Patents

Abstract

The present invention relates to a gel nail polish composition comprising an acrylate containing an acetal group, a photoinitiator, and a photoacid generator as an active ingredient, and uses thereof. The gel nail polish composition of the present invention not only can be cured within a short time, but also contains an acetal structure that can be decomposed after use, so that photocured products can be easily decomposed under acidic conditions. Therefore, the composition of the present invention can be easily used in the gel nail related industry because it is possible to easily replace nail care products to suit consumer′s preferences while minimizing damage to the nails and surrounding skin compared to the prior art.

Description

Gel nail polish composition comprising acrylate containing acetal group, photoradical initiator and photoacid generator as effective component and uses thereof}

The present invention relates to a gel nail polish composition containing an acrylate containing an acetal group, a photoinitiator, and a photoacid generator as an active ingredient and uses thereof.

UV curable acrylate is a material that undergoes curing reaction by light at room temperature and does not require high temperature heat treatment, and is used in various fields such as coating, paint, print ink, adhesive, and functional film production due to its rapid completion of the reaction. have. In particular, the UV cured product by a polyfunctional acrylate monomer has excellent three-dimensional crosslinking in the substrate, thereby providing excellent insoluble and insoluble properties. However, these advantages serve to make chemical and physical removal of UV curable materials difficult after use. UV-curable gel nail is a cosmetic coating for nails with a variety of colors and excellent gloss, and is a cosmetic product that has recently increased in usage due to its easy curing process and excellent physical properties. However, considerable effort is required to remove insoluble and insoluble gel nails after a period of use. The most used soak-off method for removing UV curable gel nails is to remove the gel nails on the surface primarily through an electric machine and then put the nails in a solvent such as acetone to completely remove the gel nails. Will wait until. As a result, the soak-off method not only requires a long time, but can also cause damage to the nails and the skin around the nails by using an organic solvent. Therefore, even if 3D cross-linking proceeds, UV curable acrylate that can be decomposed by special chemical treatment has been developed and applied to gel nails.

Meanwhile, Korean Patent No. 1568704 discloses a composition for removing gel polish, and Korean Patent Publication No. 2017-0026283 discloses a 'gel nail polish and a method for manufacturing and using the same.' However, a gel nail polish composition containing an acrylate comprising the acetal group of the present invention, a photoinitiator, and a photoacid generator as an active ingredient and its use have not been disclosed.

The present invention was derived by the above-mentioned needs, the present invention provides a gel nail polish composition containing an acrylate containing an acetal group, a photoinitiator, and a photoacid generator as an active ingredient, and the gel nail polish composition of the present invention The present invention was completed by confirming that the photocuring reaction was excellent and that the resolution of the photocured product was significantly increased under acid catalyst conditions.

In order to solve the above problems, the present invention provides a gel nail polish composition containing an acrylate containing an acetal group, a photoinitiator, and a photoacid generator as an active ingredient.

In addition, the present invention comprises the steps of 1) synthesizing an acrylate containing an acetal group; And 2) adding a photoinitiator and a photo-acid generator to the acrylate synthesized in step 1), and then inducing a curing reaction by irradiating UV to provide a method of using a gel nail polish composition.

The present invention relates to a gel nail polish composition containing acrylate containing an acetal group, a photoinitiator, and a photoacid generator as an active ingredient and uses thereof, and the gel nail polish composition of the present invention is capable of curing within a short time, Since it contains an acetal structure that can be decomposed after use, it has a feature that photocurables can be easily decomposed under acidic conditions. Therefore, the composition of the present invention can be easily used in the gel nail industry because it can easily replace the nail care product to suit the consumer's preference while minimizing damage to the nail and surrounding skin compared to the prior art.

1 is a comparison of the curing reaction time and curing rate by UV according to the photoinitiator type (DMPA, TPO and Darocur 1173) of the TM (1,4-cyclohexanedimethanol di (1-acryloyloxy) ethyl ether) in which the acetal group of the present invention is introduced. One result.
Figure 2 is a photoacid generator (TPST; triphenylsulfonium triflate) in the cured product (resin) prepared through the curing reaction of TM (1,4-cyclohexanedimethanol di (1-acryloyloxy) ethyl ether) and the photoinitiator is introduced acetal group of the present invention It is a result of comparing the decomposition effect in the acid catalyst conditions according to the presence or absence of the.

In order to achieve the object of the present invention, the present invention provides a gel nail polish composition containing an acrylate containing an acetal group, a photoinitiator, and a photoacid generator as an active ingredient.

The term “gel” includes photoinitiators, carbon-carbon double bond unsaturated monomers and / or oligomers, has a viscosity suitable for coating natural or artificial nails, or forms artificial nails and extensions, and decorates nails Refers to an ultraviolet-curable composition.

In the gel nail polish composition of the present invention, the acrylate containing the acetal group is 1,4-cyclohexanedimethanol divinyl ether (1,4-cyclohexanedimethanol divinyl ether); Tri (ethylene glycol) divinyl ether; And 1,4-butanediol di (1-acryloyloxy) ethyl ether (1,4-butanediol di (1-acryloyloxy) ethyl ether), and any one selected from the group consisting of acrylic acid (acrylic acid) is reacted and synthesized It may be, 1,4-cyclohexanedimethanol divinyl ether (1,4-cyclohexanedimethanol divinyl ether) and acrylic acid, TM (1,4-cyclohexanedimethanol di (1-acryloyloxy) ethyl ether) synthesis When tri (ethylene glycol) divinyl ether (tri (ethylene glycol) divinyl ether) and acrylic acid are reacted, SM (tri (ethylene glycol) -di (1-acryloyloxy) ethyl ether) is synthesized, and 1,4 -When reacting butanediol di (1-acryloyloxy) ethyl ether (1,4-butanediol di (1-acryloyloxy) ethyl ether) and acrylic acid, UM (1,4-butanediol di (1-acryloyloxy) ethyl ether ) May be synthesized, but is not limited thereto.

In addition, the synthesized TM (1,4-cyclohexanedimethanol di (1-acryloyloxy) ethyl ether), SM (tri (ethylene glycol) -di (1-acryloyloxy) ethyl ether) and UM (1,4-butanediol di (1) -acryloyloxy) ethyl ether) may be represented by the following Chemical Formulas 1 to 3, but is not limited thereto.

In addition, the photoinitiator is DMPA (2,2-dimethoxy-2-phenyl acetophenone), TPO (bis (2,4,6-trimethylbenzoyl) phenyl phosphine oxide) and 2-hydroxy-2-methyl-1-phenyl-1 -Propan-1-one (2-hydroxy-2-methyl-1-phenyl-propane-1-one; Darocur 1173) may be any one selected from the group consisting of, preferably DMPA, but is not limited thereto Does not. The photoinitiator serves to initiate a polymerization reaction of monomers that can be cured by visible light, ultraviolet light, or the like.

In addition, the photoacid generator may be triphenylsulfonium triflate (TPST), but is not limited thereto.

Further, the gel nail polish composition may include 1 to 10 parts by weight of a photoinitiator and 1 to 10 parts by weight of a photoinitiator, and preferably 1 to 5 parts by weight of a photoinitiator, based on 100 parts by weight of acrylate containing an acetal group. And 1 to 7 parts by weight of a photoacid generator, more preferably 3 parts by weight of a photoinitiator and 5 parts by weight of a photoacid generator, but is not limited thereto.

When 4 parts by weight or less of the photoacid generator is added to 100 parts by weight of the acrylate, the decomposition effect of the cured product is lowered, and when more than 6 parts by weight of the photoacid generator is added, the photoacid generator for the resin before the curing reaction Solubility may be reduced, thereby inhibiting the decomposition effect of the cured product. Therefore, it is preferable to add 5 parts by weight of a photoacid generator with respect to 100 parts by weight of acrylate.

The gel nail polish composition of the present invention may be applied to human nails or toenails as a coating agent, or may be applied to artificial nails. The UV curing step can be performed using all conventional UV curing devices and curing conditions known for use in nail applications such as nail coating. As the ultraviolet curing device, for example, a UV lamp, an LED lamp, or the like can be used. The coating layer cured with the gel polish composition by ultraviolet curing may have a thickness of 1 μm to 0.5 mm.

In addition, the present invention

1) synthesizing an acrylate containing an acetal group; And

2) adding a photoinitiator and a photo-acid generator to the acrylate synthesized in step 1), and then inducing a curing reaction by irradiating UV to provide a method of using a gel nail polish composition comprising the same.

In the method of using the gel nail polish composition of the present invention, after the curing reaction of step 2), after irradiating the cured product with UV of 300 nm, in an aqueous solution of citric acid or acetic acid for 10 to 20 minutes under conditions of 25 to 35 ° C It may be to further include the step of decomposing by impregnation, preferably after the curing reaction of step 2), after irradiating the cured product with UV of 300nm, 10 to 20 minutes in an aqueous solution of citric acid under the conditions of 25 ~ 35 ℃ It may be further comprising the step of decomposing during impregnation, but is not limited thereto.

The UV range of 300 nm irradiated to decompose the cured product is a UV range capable of effectively increasing the activity of a photoacid generator that imparts acid catalyst conditions without adversely affecting the human body.

Hereinafter, the present invention will be described in more detail using examples. It is apparent to those skilled in the art that these examples are only intended to illustrate the present invention in more detail and that the scope of the present invention is not limited by them.

Example  One. Acetal group  Containing Bisensory Acrylate  Synthesis of monomer

After 0.2 g of TBC (4-tert-butylcatechol), a polymerization inhibitor, was completely dissolved in 7 g of 1,4-cyclohexanedimethanol divinyl ether, the reactor was installed in a silicon bath. Then, in the presence of nitrogen, 21 g of acrylic acid was added, and then reacted at 70 ° C. for 12 hours. After the reaction, the excess acrylic acid was removed through an evaporator, dissolved in dichloromethane, and then a polymerization inhibitor was removed using a silica column. After that, dichloromethane was removed and 94% yield of acrylate monomer TM (1,4-cyclohexanedimethanol di (1-acryloyloxy) ethyl ether) was obtained.

Example  2. Photoinitiator  And curing of monomers by UV

DMPA (2,2-dimethoxy-2-phenyl acetophenone), TPO (bis (2,4,6-) according to the type of photoinitiator with respect to 100 parts by weight of the acrylate (TM) containing the acetal group synthesized in Example 1 trimethylbenzoyl) phenyl phosphine oxide) and 2-hydroxy-2-methyl-1-phenyl-1-propane-1-one (2-hydroxy-2-methyl-1-phenyl-propane-1-one; Darocur 1173) Each was added in 3 parts by weight, and it is not related to the UV curing reaction of the current step, but after adding TPST (triphenylsulfonium triflate), a photo-acid generator, to 5 parts by weight for the decomposition reaction in the next step, irradiate UV at 370 nm for 1 minute. The reaction proceeded. As a result, when DMPA was used as a photoinitiator in DMPA, TPO, and Darocur 1173 as disclosed in FIG. 1, the highest crosslinking rate (UV irradiation 20 seconds; 75%) was exhibited. For acrylate synthesis, it was confirmed that DMPA is the most suitable photoinitiator.

Example  3. Under acidic catalyst Acetal  Decomposition and 3D network Solubilization

In Example 2, a crosslinked film obtained through a photocuring reaction of acrylate (TM) containing an acetal group and DMPA, a photoinitiator, was added with a photoacid generator TPST, and was irradiated with UV at 370 nm. Remains as Therefore, in Example 3, the photocured product of Example 2 was irradiated with UV of 300 nm for 5 minutes to activate TPST, and a decomposition reaction was induced by impregnating an aqueous solution of citric acid (30 wt%) at a temperature of 35 ° C for 20 minutes. . As a result, as shown in Figure 2, in the case of TM resin (45.0%) added with TPSP under the acid catalyst conditions, it was confirmed that the film thickness is significantly reduced compared to TM resin (98.8%) without added TPSP. Did.

Claims (7)

1,4-cyclohexanedimethanol divinyl ether, tri (ethylene glycol) divinyl ether and 1,4-butanediol di (1-acrylo Acetyl group-containing acrylate, photoinitiator, synthesized by reacting any one selected from the group consisting of 1,4-butanediol di (1-acryloyloxy) ethyl ether with acrylic acid Gel nail polish composition containing a photoacid generator as an active ingredient. delete The method according to claim 1, wherein the photoinitiator is DMPA (2,2-dimethoxy-2-phenyl acetophenone), TPO (bis (2,4,6-trimethylbenzoyl) phenyl phosphine oxide) and 2-hydroxy-2-methyl-1. -Phenyl-1-propan-1-one (2-hydroxy-2-methyl-1-phenyl-propane-1-one) gel nail polish composition, characterized in that any one selected from the group consisting of. The gel nail polish composition of claim 1, wherein the photoacid generator is triphenylsulfonium triflate (TPST). The gel nail polish composition of claim 1, comprising 1 to 10 parts by weight of a photoinitiator and 1 to 10 parts by weight of a photoacid generator based on 100 parts by weight of the acrylate. 1) 1,4-cyclohexanedimethanol divinyl ether, tri (ethylene glycol) divinyl ether and 1,4-butanediol di (1- Acrylate containing acetal is synthesized by reacting any one selected from the group consisting of acryloyloxy) ethyl ether (1,4-butanediol di (1-acryloyloxy) ethyl ether) with acrylic acid. To do; And
2) After adding the photoinitiator and photoacid generator to the acrylate synthesized in step 1), inducing a curing reaction by irradiating UV; a method of using a gel nail polish composition comprising a. The method of claim 6, after the curing reaction of step 2), after irradiating the cured product with UV of 300nm, decomposing by impregnating a citric acid aqueous solution or acetic acid aqueous solution for 10 to 20 minutes under conditions of 25 to 35 ° C. Method of using a gel nail polish composition characterized in that it further comprises.

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