KR101026724B1 - Making method for one-liquid type curable polyurethane resin composition for logo label for clothing - Google Patents

Abstract

The present invention relates to a method for producing a one-component curable polyurethane resin composition for logo labels used in footwear and clothing, and more particularly, by reacting a polyol and a diisocyanate, the molar ratio (NCO / OH) of the isocyanate group and the hydroxyl group is 1.2-. Isocyanate terminal prepolymer in the range of 3 is synthesized, and isocyanate is completely blocked using a blocking agent, and then, additives such as a curing agent, a plasticizer, and an antifoaming agent are mixed well to prepare a stable state. While maintaining a high temperature above a certain temperature is a method of producing a one-component curable polyurethane resin composition for environmentally friendly logo labels used in shoes and clothes that can be dissociated and react with the curing agent.

1 component, hardener, polyurethane

Description

Making method for one-liquid type curable polyurethane resin composition for logo label for clothing}

 The present invention relates to a method for producing a one-component curable polyurethane resin composition for logo labels used in shoes and clothes, and more particularly, one-component curable poly for logo labels used in shoes and clothes used as substitutes for silicone rubber. It relates to a method for producing a urethane resin composition.

The logo label is a decorative product used in various fields such as shoes, clothing, and sundries, and has many uses such as outsoles, bags, clothes, and home appliances, and its usage is gradually increasing due to the development of the industry. As a material for the logo label, soft PVC was initially used, but there were restrictions on use due to environmental problems, and recently, liquid silicone and TPU have replaced it.

However, in the case of silicone rubber, there is an advantage in that the texture is soft, but the physical properties are low, and there is a disadvantage in that it is difficult to bond between copper materials, and in the case of TPU, yellowing due to UV (ultraviolet), nitrogen oxide, heat, etc. It was not suitable for the following, and it was not easy to give ductility and the cutting surface was not clean.

Currently, it is manufactured and used using liquid silicone. The silicone rubber used here still suffers from poor mechanical properties and poor adhesion to different materials such as films, nonwoven fabrics, and fabrics to be attached, and has to undergo a separate pretreatment process, and the raw material itself is expensive. There has been a problem.

Polyurethane resin has excellent mechanical strength, good feel, and has higher surface energy than silicone rubber, so it has superior adhesiveness and printing characteristics with dissimilar materials and lower price than liquid silicone. Although it is researched as a material, the liquid polyurethane for application to the logo label manufacturing process is a two-component curing type (the applicant's patent: Korean Patent No. 0541869) that separates the main material and the curing agent, and it is difficult to control and control the curing speed. Lack of penetration in the mold has limited use.

In order to solve this problem, there is an example of applying a UV curable liquid urethane (Korea Patent, 10-0637384), but it is not suitable for application to a mold mold.

 The present invention is to solve the above problems, the object of the present invention has a good texture, such as a logo label using a liquid-friendly liquid silicone without using a soft PVC, excellent workability and physical properties, and adhesiveness with the heterogeneous parts It is to provide a method for producing a one-component curable polyurethane resin composition for logo labels used in this excellent shoes and clothes.

The present invention is to achieve the above object, the method for producing a one-component curable polyurethane resin composition for logo labels used in the shoes and clothing of the present invention

Isocyanate terminal prepolymer manufacturing step by diisocyanate reaction by adding polyol and isocyanate;

A blocking step of blocking by adding a blocking agent to the isocyanate terminal prepolymer; And

Including the additive input step of adding a curing agent, plasticizer and antifoaming agent to the blocked polyurethane resin prepared in the blocking step,

The molar ratio (NCO / OH) of the isocyanate group of the isocyanate group and the hydroxyl group of the polyol is in the range of 1.2 to 3, and the blocked isocyanate is in the range of 5-25% of the weight of the prepolymer.

According to a preferred embodiment, in addition to the catalyst in the additive addition step, the catalyst is used 0.05 to 1.5 parts by weight based on 100 parts by weight of polyol, triethylamine, N-methylmorpholine, N, N- Dimethylbenzylamine, N, N-dimethylethanolamine, tin chloride, antimony trichloride, bismuth nitrate, dibutyltin dilaurate, red (Pb) octoate, cobalt octoate and mixtures thereof.

According to a preferred embodiment, the blocking agent is from the group consisting of ethanol, isopropanol 1-chloro-2-butanol, phenol, 2-pyridinol, cresol, acetylacetone, oxime, phosgene, caprolactam, pyrrolidone and mixtures thereof Is selected.

According to a preferred embodiment, the curing agent is selected from a polyfunctional amine or a polyfunctional hydroxy compound as a compound containing active hydrogen reacting with isocyanate and having two or more functional groups, and the active hydrogen of the curing agent and the isocyanate group of isocyanate. The molar ratio of the molar ratio (active hydrogen / NCO) is in the range of 1 to 1.5.

According to a preferred embodiment, the plasticizer is used 5 to 50 parts by weight based on 100 parts by weight of the polyol, the plasticizer is phthalic acid, aliphatic acid, trimellitic acid, phosphoric acid-based, epoxy-based, low polymerization polyester Is selected.

According to a preferred embodiment, the defoaming agent is used 0.05 to 1.5 parts by weight based on 100 parts by weight of the polyol, the antifoaming agent is selected from polydimethylsiloxane, modified polydimethylsiloxane, non-silicone polymer solution, mineral oil.

According to a preferred embodiment, a stabilizer and a filler are additionally added in the additive input step, wherein the stabilizer is selected from a heat stabilizer and a UV absorber, and 0.05 to 2 parts by weight based on 100 parts by weight of polyol is used, and as the filler It is selected from calcium carbonate and silica, and 1 to 20 parts by weight based on 100 parts by weight of polyol is used.

The one-component curable polyurethane resin composition for logo label used in the shoes and clothes of the present invention by the above problem solving means has a good texture and excellent mechanical properties and adhesion.

In addition, the polyurethane resin composition of the present invention is a one-component polyurethane resin composition, unlike the two-component type that is difficult to work because the main body and the curing agent is separated, the operation is simple and has the effect of controlling the curing rate and strengthening penetration in the fine mold. .

Hereinafter, with reference to the accompanying drawings will be described in more detail with respect to the one-component curable polyurethane resin composition for logo labels used in shoes and clothes of the present invention.

First, a blocking agent is added to an isocyanate terminated prepolymer prepared by the reaction of a polyol and a diisocyanate, and then additives such as a curing agent, a plasticizer, a catalyst, and an antifoaming agent are added to the blocked polyurethane resin prepared by completely blocking the isocyanate, and then mixed well. do.

In more detail, first, the polyol to be used for the experiment was purified by distillation under reduced pressure at 100 to 110 ° C., and then the polyol and diisocyanate were put into a five-necked flask equipped with a stirrer, a cooler, and a nitrogen injector, and the temperature was raised to 60 to 100 ° C. to obtain nitrogen. The reaction is stirred while stirring at a speed of 100 to 300 rpm for 1 to 3 hours.

 Next, confirm that the NCO content of the isocyanate terminated prepolymer has reached the theoretical value, add a blocking agent, stir for 30 minutes to 2 hours, and then confirm that the isocyanate is completely blocked by IR analysis, and then hardener, plasticizer, and catalyst. And additives such as an antifoaming agent are mixed well to prepare a one-component polyurethane resin.

Polyols used in the polyurethane resin production of the present invention can be used polyether polyols, polyester polyols, phenolic polyols and the like, and those containing two or more hydroxyl groups in the number average molecular weight in the range of 1,000 ~ 4,000.

 Polyether polyols are obtained by addition reaction of alkylene oxides such as ethylene oxide and propylene oxide to polyhydroxyalkane or amine compounds. As hydroxyalkane, glycols such as ethylene glycol and propylene glycol, glycerol, trimethylolpropane, etc. Triol is used, and as the amine compound, ammonia, triethanolamine, ethylenediamine and the like can be used. Polyester polyols are obtained by the reaction of dicarboxylic acids containing from 2 to 12 carbon atoms with at least one diol.

Examples of dicarboxylic acids include aliphatic divalent acids such as adipic acid, succinic acid, akelic acid, sebacic acid, suberic acid and glutaric acid, and aromatic acids such as phthalic acid, isophthalic acid, terephthalic acid and naphthenic acid. Included. Suitable diols of the present invention include glycols containing 2 to 8 carbon atoms, such as ethylene glycol, diethylene glycol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, and the like. And polyhydric alcohols such as glycerol, trimethylolpropane, pendaerythritol and the like.

Also included are lactone polyester polyols obtained by ring-opening polymerization of cyclic esters such as caprolactone. And a phenolic polyol prepared by reacting a noblock resin or a resol resin with an alkylene oxide may be used, and in the present invention, the polyol may be used alone or in combination of two or more.

 Isocyanates used in the present invention include aromatic, saturated or unsaturated cyclic compounds, aliphatic compounds, and the like, for example, toluene diisocyanate, 4,4'-diphenylmethane diisocyanate, xylene diisocyanate, hydrogenated diphenylmethane diisocyanate , Isophorone diisocyanate, cyclohexanediisocyanate, hexamethylene diisocyanate and the like.

And the molar ratio (NCO / OH) of isocyanate group and hydroxyl group is 1.2 ~ 3, and when the molar ratio is less than 1.2, overall physical properties including hardness are lowered. When it exceeds 3, the polyurethane resin's hardness is improved but it is too hard. Not suitable for use as logo labels used in shoes and clothing.

 The catalyst used in the synthesis of the polyurethane resin is 0.05 to 1.5 parts by weight based on 100 parts by weight of polyol and less than 0.05 parts by weight, the reaction rate is slow and unreacted substances may be left. Although the foaming speed is increased, low molecular weight oligomers are produced, which may lead to deterioration of mechanical properties.

Examples of such a catalyst include tertiary amines such as triethylamine, N-methylmorpholine, N, N-dimethylbenzylamine, N, N-dimethylethanolamine, acidic metal salts such as tin chloride, antimony trichloride, bismuth nitrate, Metal compounds, such as dibutyl tin dilaurate, red (Pb) octoate, and cobalt octoate, etc. can be used, and can be used individually or in combination.

 The blocking agent maintains a stable form at room temperature by reacting with isocyanate, but dissociates when it reaches a certain temperature, thereby making the isocyanate reactive. It is used as the isocyanate and equivalent ratio remaining after reacting with the hydroxyl group of polyol.

Such compounds include ethanol, butanol, 2-ethylhexyl alcohol, isopropanol, cyclohexyl alcohol, 2-ethoxyhexyl alcohol, N-morpholino alcohol, 3-oxazolidineethanol, 1-chloro-2-butanol, phenol , 2-pyridinol, cresol, 3-hydroxypyridine, 8-hydroxyquinoline, acetylacetone, hexylmercaptan, thiophenol, mercaptopyridine, methylacetamide, p-cresolformaldehyde, pyrazole, phosgene, capro Lactams, imidazolines, oximes, methylethylketoximes, pyrrolidones and the like can be used.

In addition, the content of blocked isocyanate is appropriate in the range of 5 to 25% of the weight of the prepolymer, and when the content of blocked isocyanate is less than 5%, the overall physical properties are deteriorated, and when the content of the blocked isocyanate is greater than 25%, the hardness is improved, but the hardness is good. It is brittle and unsuitable for logo labels.

The curing agent used in the present invention is selected from a polyfunctional amine or a polyfunctional hydroxy compound as a compound containing active hydrogen reacting with an isocyanate and having two or more functional groups, and a molar ratio of the active hydrogen of the curing agent to the isocyanate group of the isocyanate. The molar ratio of (active hydrogen / NCO) is in the range of 1 to 1.5, and the mechanical properties of the cured resin can be controlled by controlling the type and content of the curing agent.

When using a curing agent, when the molar ratio of active hydrogen / NCO is less than 1, the hardness of the logo label decreases, and when used above 1.5, the hardness becomes too high, making it unsuitable for logo labels used in shoes or clothing, and remains unreacted. Hardeners present can lead to other mechanical properties deterioration.

Such crosslinkers include diethanolamine, triethanolamine, diisopropanolamine, tetraethylenepentamine, diethylenetriamine, xylenediamine, 1,3-diaminopropane, isophoronediamine, 1,3-cyclohexanebis (methyl Amines), polyethyleneamine, ethylene glycol, butanediol, 1,6-hexanetriol, glycerin, trimethylolpropane, melamine and the like, various low molecular weight multifunctional hydroxy or amine compounds can be used.

 In the present invention, the plasticizer improves the workability and flexibility of the product and lowers the dissociation temperature of the blocked isocyanate and may be used as a compound such as dibutyl phthalate, dioctyl phthalate, diisodecyl phthalate, diisononyl phthalate, and the like. Aliphatic acids such as phthalic acid, di-2-ethylhexyl adipate, di-2-ethylhexyl azelate, trimellitic acid such as triethylhexyl trimellitate, triisononyl trimellitate, and tricresyl phosphate Phosphoric acid-based compounds such as tri-2-ethylhexyl phosphate, epoxidized linseed oil epoxidized double bonds of unsaturated fatty acid glycerol esters with hydrogen peroxide or peracetic acid, and low-polymerization polyesters having an average molecular weight of 1,000 to 8,000. The compound is present in an amount of 5 to 50 parts by weight based on 100 parts by weight of the polyol, depending on the intended use. If the plasticizer is used in less than 5 parts by weight, the workability is inferior, and if it is used in excess of 50 parts by weight, the workability is excellent and the dissociation temperature of the block isocyanate is lowered, but the mechanical properties are greatly reduced.

 Antifoaming agent of the present invention is used to remove bubbles generated during curing of the polyurethane resin, polydimethylsiloxane-based, modified polydimethylsiloxane-based, non-silicone-based polymer solution, mineral oil-based antifoaming agent, and the like, 100 parts by weight of polyol Use 0.05 to 1.5 parts by weight. If the antifoaming agent is used less than 0.05 parts by weight, bubbles are not completely removed when preparing the cured resin. If the antifoaming agent is used in excess of 1.5 parts by weight, the excessive antifoaming agent may act as an impurity, thereby deteriorating mechanical properties.

 According to other needs, stabilizers and fillers can be used as additives, and heat stabilizers and ultraviolet absorbers can be used as stabilizers, and 0.05 ~ 2 parts by weight can be used relative to 100 parts by weight of polyol. This is used may be used 1 to 20 parts by weight relative to 100 parts by weight of polyol.

The one-component curable polyurethane resin composition for a logo label manufactured by the manufacturing method of the present invention is a liquid one-component type, so that the logo label used for shoes or clothes can be easily produced by a mold casting method. That is, it is injected into a mold for a logo label by a mold casting method, and is manufactured by heat treatment at 110 to 180 ° C. for 5 to 10 minutes. In the case of manufacturing a logo label using silicone, the production of the logo label is complicated, such as pressing a press, the resin composition of the present invention can be produced simply and simply by the mold casting method.

Hereinafter, the present invention will be described in detail with reference to Examples, but the present invention is not limited to Examples.

(Example 1)

 100 g of polyester polyol (product name: DT-1040, molecular weight: 1,000, Daewon polymer) and 50 g of methylene diphenyl diisocyanate were added to a five-necked separate flask equipped with a stirrer, a cooler, and a nitrogen injector. While reacting, the reaction was stirred at a speed of 100 to 150 rpm for about 3 hours.

Then, it was confirmed that the NCO content of the isocyanate prepolymer having isocyanate group at the end reached the theoretical value, 9 g of dimethylethanolamine was added as a blocking agent and stirred for 2 hours, and then the IR analysis confirmed that the isocyanate was completely blocked. After dibutyltin dilaurate 0.1g, dibutylphthalate 20g, polysiloxane antifoaming agent (BYK 201, BYK chemie) 0.1g, amine-based curing agent (KH-240, kukdo epoxy) 10g well mixed and a one-component curable polyurethane resin Prepared.

 A certain amount of one-component curable polyurethane prepared in a Teflon mold was poured and cured in a 150 ° C. oven for 10 minutes to prepare a urethane film having a constant thickness, and then evaluated mechanical properties.

(Example 2)

 A one-component curable polyurethane resin was prepared in the same manner as in Example 1 except that 8.7 g of methyl ethyl ketoxime was used instead of dimethylethanolamine as the blocking agent in Example 1, and mechanical properties thereof were evaluated.

(Example 3)

A 1-liquid curable polyurethane resin was prepared in the same manner as in Example 1, except that NCO / OH was adjusted to 1.5 using 37.5 g of methylenediphenyl diisocyanate in Example 1 and 4.5 g of dimethylethanolamine was used. And mechanical properties were evaluated.

(Comparative Example 1)

 A 1-liquid curable polyurethane resin was prepared in the same manner as in Example 1, except that NCO / OH was adjusted to 1.1 using 27.5 g of methylenediphenyl diisocyanate in Example 1, and 0.9 g of dimethylethanolamine was used. And mechanical properties were evaluated.

In Comparative Example 1, unlike the examples, the molar ratio (NCO / OH) of the isocyanate group and the hydroxy is approximately 1.1, which is outside the range of the molar ratio (NCO / OH) 1.2-3 mentioned in the examples.

(Comparative Example 2)

 To 100 g of polyester polyol (product name: DT-1040, molecular weight: 1,000, Daewon polymer) 34 g of block isocyanate resin (hexamethylene diisocyanate, Desmodur-BL3175, Bayer Germany) 34 g, dibutyl tin dilaurate 0.1 g, dibutyl phthalate 20 g 0.1 g of polysiloxane antifoaming agent (BYK 201, BYK chemie) and 10 g of amine curing agent (KH-240, kukdo epoxy) were mixed well to prepare a one-component polyurethane resin using block isocyanate and mechanically Physical properties were evaluated.

In Comparative Example 2, unlike the examples, the polyol and the isocyanate are not reacted to prepare an isocyanate terminal prepolymer, but using a blocked block isocyanate and a separate blocking agent is not used.

(Comparative Example 3)

 100 g of polyester polyol (product name: DT-1040, molecular weight: 1,000, Daewon polymer) was reacted with 50 g of methylene diphenyl diisocyanate to prepare isocyanate terminal prepolymer (topic), 0.1 g of dibutyl tin dilaurate, 20 g of dibutyl phthalate , 0.1g polysiloxane antifoaming agent (BYK 201, BYK chemie), 1g amine curing agent (KH-240, kukdo epoxy) were mixed well to prepare a curing agent mixture (curing agent), and then mixed with the main agent and the curing agent immediately before the polyurethane casting Mechanical properties were evaluated in the same manner as in Example 1.

In Comparative Example 3, the molar ratio (NCO / OH) of the isocyanate group and hydroxy is approximately 2, which is in the range of the molar ratio (NCO / OH) 1.2-3 mentioned in the examples, but Comparative Example 3 is different from the examples. This is the case when no blocking agent is used.

(Comparative Example 4)

 Silicone labels used for logo labels used in shoes or clothing were evaluated for mechanical properties under the same evaluation conditions as in Example 1.

 Comparative Example 4 was experimented using the logo label of the silicone rubber material generally used in the past.

(Test Methods)

The polyurethanes prepared in Examples and Comparative Examples were evaluated for mechanical properties by the following method.

Hardness

Hardness was measured using a C type hardness meter according to ASTM D2240. The measurement was performed ten times or more at any point of the specimen and used the average value.

The tensile strength, Elongation rate  ( Tensile strength  & Elongation )

After the polyurethane elastomer obtained was about 5 mm thick, test specimens were prepared with a B-type cutter according to KS M 6518 to measure tensile strength and elongation. At this time, five test pieces were used for the same test.

Tear strength ( Tear strength )

After making the obtained polyurethane elastomer about 5mm thick, the test piece was produced with the B type cutter based on KS M 6518, and the tear strength was measured. At this time, five test pieces were used for the same test.

Adhesion

 The polyurethane resin was coated on the thermoplastic polyurethane (TPU) adherend without any primer treatment, and then cured at 150 ° C. for 10 minutes, and then evaluated by using a universal tensile tester.

Resilience

 The resilience was measured using a rebound resilience tester manufactured by Wallace, England, to prepare a 15 mm thick specimen.

The results for this experiment are shown in the following table.

Table 1. Formulation Table (Examples 1 to 3, Comparative Examples 1 to 4)

ingredient Example 1 Example
2 Example 3 Comparative Example 1 Comparative example
2 Comparative example
3 Comparative Example 4
Polyol Polyester polyol
(DT-1040, molecular weight: 1.000) 100 100 100 100 100 100


Original silicone logo label








Diisocyanate Methylenediphenyl
Diisocyanate 50 50 37.5 27.5 - 50 Block Isocyanate Resin (Desmodur-BL3175,
Bayer Germany) - - - - 34 - Blocking
agent Dimethylethanolamine 9 - 4.5 0.9 - - Methyl ethyl ketoxime - 8.7 - - - - catalyst Dibutyl tin dilaurate 0.1 0.1 0.1 0.1 0.1 0.1 Plasticizer Dibutyl phthalate 20 20 20 20 20 20 Antifoam Polysiloxane Defoamer
(BYK201, BYK chemie) 0.1 0.1 0.1 0.1 0.1 0.1 Hardener Amine Curing Agent
(KH-240, kukdo epoxy) 10 10 10 10 10 10

Table 2. Physical Properties (Examples 1 to 3, Comparative Examples 1 to 4)

Example 1 Example 2 Example 3 Comparative Example 1 Comparative Example 2 Comparative Example 3 Comparative Example 4 Curing form 1 component 1 component 1 component 1 component 1 component 2-part

silicon
Zhejiang
(60 ℃ .300 hours)
Good
Good
Good
Good
Good
20 minutes later Hardness
(Ctype,
23 ℃)
79-81
80-82
72-73
66-67
74-75
80-81
72-73 The tensile strength
(kgf / cm ² )
180
192
150
70
85
190
103 Phosphorus strength
kgf / cm)
61
66
52
20
32
62
39 Elongation (%) 270 260 335 300 200 260 190 Resilience (%) 35 34 31 20 29 35 33 Adhesion
(gf / 2cm)
900
700
750
500
370
800 Delami-nation

Adhesion ^* : Adhesion to thermoplastic polyurethane (TPU).

Examining the experimental results, in Examples 1-3, hardness, tensile strength, tear strength, elongation rate, and resilient elastic adhesive force were further increased in comparison with the case of using the silicon of Comparative Example 4, which is currently widely used for logo labels. great.

That is, in Examples 1, 2, and 3, physical properties such as hardness, tensile strength, tear strength, elongation rate, rebound elasticity, and the like are superior to or similar to those of silicon, and have substantially similar physical properties. In the present invention, there is a problem in that peeling occurs, whereas in Example 1-3, it can be confirmed that it has excellent adhesion.

On the contrary, Comparative Example 1, in which the molar ratio (NCO / OH) of the isocyanate group and the hydroxy key is about 1.1, is not only poor in physical properties compared to the Examples, but also compared to silicone (Comparative Example 1) currently used for logo labels. It can be seen that the physical properties are poor.

On the other hand, in Comparative Example 2 using a block isocyanate resin without using a blocking agent, the hardness is similar to that of silicon, but the tensile strength, tear strength, elongation rate, and resilience properties are inferior.

Comparative 3, which does not use a blocking agent, has superior physical properties compared to silicone (Comparative Example 4), but has a fatal disadvantage of poor gelling due to gelation after 20 minutes at 60 ° C.

The present invention described above is not limited to the above-described embodiment and the accompanying drawings, and in the technical field to which the present invention pertains that substitutions, modifications, and conversions can be made without departing from the technical spirit of the present invention. It will be evident to those who have knowledge of.

Claims (7)

In the method of manufacturing a one-component curable polyurethane resin composition for logo labels used in shoes and clothes, Isocyanate terminal prepolymer manufacturing step by diisocyanate reaction by adding polyol and isocyanate; A blocking step of blocking by adding a blocking agent to the isocyanate terminal prepolymer; And Including the additive input step of adding a curing agent, plasticizer and antifoaming agent to the blocked polyurethane resin prepared in the blocking step, The molar ratio (NCO / OH) of the isocyanate group of the isocyanate group and the hydroxy group of the polyol is in the range of 1.2 to 3, Blocked isocyanate is a method for producing a one-component curable polyurethane resin composition for a logo label, characterized in that in the range of 5-25% of the weight of the prepolymer. The method of claim 1, The catalyst is further added to the additive input step, The catalyst is used 0.05-1.5 parts by weight based on 100 parts by weight of polyol, Triethylamine, N-methylmorpholine, N, N-dimethylbenzylamine, N, N-dimethylethanolamine, Preparation of a one-component curable polyurethane resin composition for logo label, characterized in that selected from the group consisting of tin chloride, antimony trichloride, bismuth nitrate, dibutyl tin dilaurate, red (Pb) octoate, cobalt octoate and mixtures thereof Way. The method of claim 1, The blocking agent is selected from the group consisting of ethanol, isopropanol 1-chloro-2-butanol, phenol, 2-pyridinol, cresol, acetylacetone, oxime, phosgene, caprolactam, pyrrolidone and mixtures thereof. Method for producing a one-component curable polyurethane resin composition for logo labels. The method of claim 1, The hardener is selected from a polyfunctional amine or a polyfunctional hydroxy compound as a compound containing active hydrogen reacting with isocyanate and having two or more functional groups, The molar ratio of the molar ratio (active hydrogen / NCO) of the active hydrogen of the said hardening | curing agent and the isocyanate group of isocyanate is 1-1.5 range, The 1-component curable polyurethane resin composition manufacturing method for logo labels. The method of claim 1, The plasticizer is used 5 to 50 parts by weight based on 100 parts by weight of polyol, The plasticizer is a method of producing a one-component curable polyurethane resin composition for a logo label, characterized in that selected from phthalic acid, aliphatic acid, trimellitic acid, posopolic acid, epoxy clock, low-polymerization polyester. The method of claim 1, The antifoaming agent is used 0.05-1.5 parts by weight based on 100 parts by weight of polyol, The antifoaming agent is a method for producing a one-component curable polyurethane resin composition for a logo label, characterized in that selected from polydimethylsiloxane, modified polydimethylsiloxane, non-silicone polymer solution, mineral oil. The method of claim 1, In addition to the stabilizer, the filler is added in the additive input step, The stabilizer is selected from thermal stabilizers, ultraviolet absorbers, 0.05 to 2 parts by weight based on 100 parts by weight of polyol, The filler is selected from calcium carbonate and silica and 1 to 20 parts by weight based on 100 parts by weight of polyol is used for producing a one-component curable polyurethane resin composition for a logo label.