KR101899407B1 - Manufacturing method of water-dispersion isocyanate using blocked reactive surfactant and water-dispersion isocyanate manufactured by thereof - Google Patents

Abstract

Disclosed is a process for the preparation of water-dispersed isocyanates and a water-dispersed isocyanate produced thereby. More specifically, the present invention relates to a process for producing a water-dispersed isocyanate, A second step of adding a blocking agent to the reactant in the first step to synthesize a blocked reactive surfactant; And a third step of water-dispersing the surfactant synthesized in the second step in the polyfunctional block isocyanate to thereby obtain an aqueous dispersion isocyanate having excellent adhesion even after curing and a water-dispersed isocyanate prepared thereby .

Description

TECHNICAL FIELD [0001] The present invention relates to a water-dispersed isocyanate and a water-dispersed isocyanate, and to a water-dispersed isocyanate using the blocked reactive surfactant,

Disclosed is a method for producing water-dispersed isocyanate, and more particularly, a method for producing water-dispersed isocyanate in which heat-sealability after curing is improved by dispersing water using a blocked reactive surfactant.

Early automotive tires were made of pure rubber but had a short life span. In order to solve this problem, the tire cord was the first to have durability by putting fiber material inside rubber. Generally, a tire cord made of a material such as nylon, polyester fiber or steel is used in order to reinforce the heat resistance and strength of a tire. Such a tire cord has almost no compatibility with rubber, have.

Accordingly, various adhesives have been used to properly bond or adhere rubber to tire cords that are not compatible. Typically, Resorcinol-Formaldehyde-latex (RFL), which is composed of resorcinol, formaldehyde and latex, is used. As the latex, a mixed latex such as styrene-butadiene copolymer latex, vinylpyridine-styrene-butadiene terpolymer latex or natural rubber latex is generally used. However, since resorcinol is a raw material obtained from petroleum resources, there is a problem of raising production cost due to an increase in price due to depletion of crude oil resources, and as an adhesive composition of a new material that can replace the resorcinol, the consumption amount of environmentally friendly type water- .

The adhesive used for the tire cord essentially uses a cross-linking agent to maintain a strong and stable adhesive force even in harsh environments such as high temperature resistance which is required to withstand high temperatures of 300 ° C or higher and fatigue resistance which must endure high-speed traveling for a long time. Crosslinking agents conventionally used for tire cords include isocyanate compounds, melamine resin compounds, glyoxal resin compounds and urea resin compounds, among which isocyanate compounds are mainly used.

In addition, isocyanates are widely used in various fields such as water repellent agents, coupling agents, and crosslinking agents in addition to crosslinking agents for tire cords, and are excellent in properties such as dispersibility, stability after dispersion, adhesion after curing, heat resistance after curing, It is required to develop an isocyanate having a new function without deterioration of the isocyanate.

In the industrial field, adhesives are prepared by adding additives such as dispersants, antifoaming agents and surfactants to block isocyanates using various blocking agents. However, such an additive remains as an uncured product in the water-dispersed isocyanate, so that there is a problem that the physical properties required as a tire cord adhesive have a bad influence on adhesion after curing and heat-resistant adhesion after curing.

KR 100385569 B1

Disclosed is a process for producing a water-dispersed isocyanate having excellent adhesion even after curing, and a water-dispersed isocyanate prepared by the process.

According to one aspect of the present invention, there is provided a method for producing a polyisocyanate compound, which comprises reacting an isocyanate with at least one compound selected from the group consisting of polyoxyethylene monomethyl ether, polyoxypropylene monomethyl ether, mixed polyoxyethylene / propylene monomethyl ether, polyoxyethylene cetyl ether, polyoxyethylene lauryl ether, Polyoxyethylene stearyl ether, polyoxyethylene tridecyl ether, polyoxyethylene decyl ether, polyoxyethylene phenyl ether, polyoxyethylene octyl ether, polyoxyethylene ester ether, polyoxyethylene stearyl ether, polyoxyethylene stearyl ether, Polyoxyethylene stearyl esters, polyoxyethylene stearyl esters, polyoxyethylene stearyl esters, polyoxyethylene stearyl esters, polyoxyethylene stearyl esters, polyoxyethylene stearyl esters, polyoxyethylene stearyl esters, polyoxyethylene stearyl esters, pole At least one selected from the group consisting of oxyethylene tridecyl ester, polyoxyethylene tridecyl ester, polyoxyethylene tridecyl ester, polyoxyethylene tridecyl ester, polyoxyethylene decyl ester, polyoxyethylene phenyl ester, polyoxyethylene octyl ester and polyoxyethylene caster ester is used at a ratio of 1: 0.3 to 0.7 The first step of the first step; A second step of synthesizing a blocked reactive surfactant by adding a blocking agent to the reactant prepared in the first step; And a third step of water-dispersing the polyfunctional block isocyanate by adding the surfactant synthesized in the second step to the water-dispersed isocyanate.

The above-mentioned polyoxyethylene monomethyl ether, polyoxypropylene monomethyl ether, mixed polyoxyethylene / propylene monomethyl ether, polyoxyethylene cetyl ether, polyoxyethylene lauryl ether, polyoxyethylene oleyl ether, polyoxyethylene Polyoxyethylene stearyl ether, polyoxyethylene decyl ether, polyoxyethylene phenyl ether, polyoxyethylene octyl ether, polyoxyethylene chain ester ether, polyoxyethylene monomethyl ester, poly Polyoxyethylene oleyl ester, polyoxyethylene stearyl ester, polyoxyethylene tridecyl ester, polyoxyethylene stearyl ester, polyoxyethylene stearyl ester, polyoxyethylene stearyl ester, polyoxyethylene stearyl ester, polyoxyethylene stearyl ester, Poly At least one selected from the group consisting of oxyethylene tridecyl ester, polyoxyethylene decyl ester, polyoxyethylene phenyl ester, polyoxyethylene octyl ester and polyoxyethylene caster ester may have a weight average molecular weight of 300 to 5,000.

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In addition, the blocking agent may include at least one selected from the group consisting of epsilon caprolactam, delta valerolactam, butyl cellosolve, phenol, cresol, resorcinol, and emkeoloxime.

In the second step, the blocking agent may be added in an equivalent ratio of 1: 0.3 to 0.7 with respect to the isocyanate of the first step.

In the third step, the surfactant may be administered in an amount of 5 to 15% by weight based on 100% by weight of the total amount of the water-dispersed isocyanate to be produced.

According to another aspect of the present invention, there is provided a water-dispersed isocyanate, which is produced by the above production method.

The water-dispersed isocyanate produced by the production method according to one aspect of the present invention can remarkably improve the adhesion after curing and the heat-resistant adhesion after curing since unreacted materials do not remain after dispersion.

The water-dispersed isocyanate produced by the production method according to one aspect of the present invention is suitable for application to adhesives for tire cords because of its excellent dispersibility, stability, adhesion after curing and heat-resistant adhesion after curing.

The present invention relates to a process for producing an aqueous dispersion isocyanate and a water-dispersed isocyanate prepared thereby, and more particularly to a process for producing an aqueous dispersion of an isocyanate comprising a polyoxyethylene monomethyl ether, a polyoxypropylene monomethyl ether, a polyoxyethylene / propylene mixed monomethyl ether , Polyoxyethylene cetyl ether, polyoxyethylene lauryl ether, polyoxyethylene oleyl ether, polyoxyethylene stearyl ether, polyoxyethylene tridecyl ether, polyoxyethylene tridecyl ether, polyoxyethylene decyl ether, polyoxyethylene Polyoxyethylene oleyl ether, ethylene phenyl ether, polyoxyethylene octyl ether, polyoxyethylene castor ether, polyoxyethylene monomethyl ester, polyoxypropylene monomethyl ester, mixed polyoxyethylene / propylene monomethyl ester, polyoxyethylene cetyl ester, Polyoxyethylene stearyl esters, polyoxyethylene tridecyl esters, polyoxyethylene decyl esters, polyoxyethylene phenyl esters, polyoxyethylene octyl esters, polyoxyethylene stearyl esters, polyoxyethylene alkyl esters, polyoxyethylene stearyl esters, And polyoxyethylene caster ester at an equivalent ratio of 1: 0.3 to 0.7 to perform a first reaction; A second step of synthesizing a blocked reactive surfactant by adding a blocking agent to the reactant prepared in the first step; And a third step of water-dispersing the polyfunctional block isocyanate with the surfactant synthesized in the second step, and a water-dispersed isocyanate prepared by the method.

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

According to one aspect of the present invention, a process for producing an aqueous dispersion isocyanate is provided.

Disclosed is a process for producing an aqueous dispersion isocyanate according to one aspect of the present invention, comprising reacting an isocyanate with a polyoxyethylene monomethyl ether, a polyoxypropylene monomethyl ether, a polyoxyethylene / propylene mixed monomethyl ether, a polyoxyethylene cetyl ether, Polyoxyethylene oleyl ether, polyoxyethylene stearyl ether, polyoxyethylene tridecyl ether, polyoxyethylene tridecyl ether, polyoxyethylene decyl ether, polyoxyethylene phenyl ether, polyoxyethylene octyl ether, poly Polyoxyethylene oleyl ester, polyoxyethylene oleyl ester, polyoxyethylene oleyl ester, polyoxyethylene oleyl ester, polyoxyethylene oleyl ester, polyoxyethylene oleyl ester, polyoxyethylene oleyl ester, polyoxyethylene sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, At least one selected from the group consisting of oxyethylene stearyl ester, polyoxyethylene tridecyl ester, polyoxyethylene tridecyl ester, polyoxyethylene decyl ester, polyoxyethylene phenyl ester, polyoxyethylene octyl ester and polyoxyethylene ester ester And a first step in which one is added to perform a first reaction.

The above polyoxyethylene monomethyl ether, polyoxypropylene monomethyl ether, polyoxyethylene / propylene mixed type monomethyl ether, polyoxyethylene cetyl ether, polyoxyethylene lauryl ether, polyoxyethylene oleyl ether, polyoxyethylene stearyl But are not limited to, ether, polyoxyethylene tridecyl ether, polyoxyethylene tridecyl ether, polyoxyethylene decyl ether, polyoxyethylene phenyl ether, polyoxyethylene octyl ether, polyoxyethylene ester ether, polyoxyethylene monomethyl ester, polyoxypropylene Polyoxyethylene oleyl ester, polyoxyethylene stearyl ester, polyoxyethylene tridecyl ester, polyoxyethylene lauryl ester, polyoxyethylene lauryl ester, polyoxyethylene stearyl ester, polyoxyethylene stearyl ester, polyoxyethylene stearyl ester, At least one selected from the group consisting of tylene tridecyl ester, polyoxyethylene decyl ester, polyoxyethylene phenyl ester, polyoxyethylene octyl ester and polyoxyethylene caster ester has excellent dispersibility and has a weight average molecular weight of 300 to 5,000 . When the weight-average molecular weight is less than 300, it is difficult to disperse the polyfunctional isocyanate in a water-dispersible manner so that it is difficult to disperse water. When the weight average molecular weight is more than 5,000, the heat-resistant adhesiveness of the tire cord is remarkably deteriorated May occur.

In the present invention, the isocyanate and the polyoxyethylene monomethyl ether, polyoxypropylene monomethyl ether, mixed polyoxyethylene / propylene monomethyl ether, polyoxyethylene cetyl ether, polyoxyethylene lauryl ether, polyoxyethylene oleyl ether , Polyoxyethylene stearyl ether, polyoxyethylene tridecyl ether, polyoxyethylene tridecyl ether, polyoxyethylene decyl ether, polyoxyethylene phenyl ether, polyoxyethylene octyl ether, polyoxyethylene caster ether, polyoxyethylene mono Methyl ester, polyoxypropylene monomethyl ester, mixed polyoxyethylene / propylene monomethyl ester, polyoxyethylene cetyl ester, polyoxyethylene lauryl ester, polyoxyethylene oleyl ester, polyoxyethylene stearyl ester, polyoxyethylene At least one selected from the group consisting of ethylene tridecyl ester, polyoxyethylene tridecyl ester, polyoxyethylene decyl ester, polyoxyethylene phenyl ester, polyoxyethylene octyl ester and polyoxyethylene ester ester is preferably used in an amount of from 1: 0.3 to 0.7 Equivalent ratio. The above polyoxyethylene monomethyl ether, polyoxypropylene monomethyl ether, polyoxyethylene / propylene mixed type monomethyl ether, polyoxyethylene cetyl ether, polyoxyethylene lauryl ether, polyoxyethylene oleyl ether, polyoxyethylene stearyl But are not limited to, ether, polyoxyethylene tridecyl ether, polyoxyethylene tridecyl ether, polyoxyethylene decyl ether, polyoxyethylene phenyl ether, polyoxyethylene octyl ether, polyoxyethylene ester ether, polyoxyethylene monomethyl ester, polyoxypropylene Polyoxyethylene oleyl ester, polyoxyethylene stearyl ester, polyoxyethylene tridecyl ester, polyoxyethylene lauryl ester, polyoxyethylene lauryl ester, polyoxyethylene stearyl ester, polyoxyethylene stearyl ester, polyoxyethylene stearyl ester, When the content of at least one selected from the group consisting of tylene tridecyl ester, polyoxyethylene decyl ester, polyoxyethylene phenyl ester, polyoxyethylene octyl ester and polyoxyethylene caster ester is less than 0.3 relative to the isocyanate, the polyfunctional isocyanate It is difficult to disperse water and the stability after water dispersion is lowered. If it exceeds 0.7, the content of isocyanate in the first reaction is lowered to lower the degree of curing with water-soluble epoxy, which may result in deterioration of adhesion with tire rubber.

The method for preparing water-dispersed isocyanate according to one aspect of the present invention includes a second step of synthesizing a blocked reactive surfactant by adding a blocking agent to the reactant prepared in the first step.

The blocking agent may include at least one selected from the group consisting of epsilon caprolactam, delta valerolactam, butyl cellosolve, phenol, cresol, resorcinol, and emkeoxime, but is not limited thereto.

In the present invention, the addition amount of the blocking agent may be mixed in an equivalent ratio of 1: 0.3 to 0.7 based on the isocyanate content of the first step. If the content of the blocking agent is less than 0.3 based on the isocyanate, the degree of curing with the water-soluble epoxy is lowered so that the adhesion with the tire rubber is deteriorated. When the amount exceeds 0.7, the water- May occur.

The method for preparing water-dispersed isocyanate according to one aspect of the present invention includes a third step of administering the reactive surfactant synthesized in the second step to the polyfunctional block isocyanate and dispersing the water.

The polyfunctional block isocyanate, the reactive surfactant, and the water-soluble solvent may be mixed and dispersed in water. In this step, the polyfunctional block isocyanate is dispersed in water through administration of the reactive surfactant synthesized in the second step, and the reactive surfactant does not remain as an unreacted material after dispersion, It is possible to remarkably improve the adhesiveness after curing and the heat-resistant adhesion after curing.

The polyfunctional block isocyanate may be included in an amount of 45 to 55% by weight based on 100% by weight of the total amount of the water-dispersed isocyanate to be produced.

The reactive surfactant may be administered in an amount of 5 to 15% by weight based on 100% by weight of the water-dispersed isocyanate to be produced. If the content of the reactive surfactant is less than 5% by weight, it is difficult to disperse the polyfunctional block isocyanate and the stability of the polyfunctional block isocyanate is lowered after the water dispersion. If the amount exceeds 15% by weight, the content of the polyfunctional block isocyanate, The degree of curing with the tire cord is lowered and the adhesion with the tire cord may be deteriorated.

According to another aspect of the present invention, there is provided a water-dispersed isocyanate produced by the manufacturing method comprising the first to third steps.

The water-dispersed isocyanate provided in the present invention is prepared by water-dispersing the blocked isocyanate using a reactive surfactant in the production step. As a result, unreacted materials do not exist after dispersing, and the adhesiveness after curing and the heat-resistant adhesion after curing can be remarkably improved while maintaining excellent dispersibility, stability and adhesion. The water-dispersed isocyanate provided in the present invention contains nonvolatile matter in an amount of 50 to 70% by weight and can be used as a curing agent suitable for an adhesive for a tire cord.

It is to be understood that both the foregoing general description and the following detailed description of the present invention are exemplary and explanatory and are intended to be illustrative of the invention and are not intended to limit the scope of the claims. It will be apparent to those skilled in the art that such variations and modifications are within the scope of the appended claims.

Example

[Production Example 1]

A thermometer, a condenser, a stirrer, a condenser and a temperature raising device were attached to a 2 liter four-necked flask. 500 g of EMK and 125 g of methylenedipetyldiisocyanate were mixed and the mixture was heated to 70 DEG C with gentle stirring. After the mixture was heated to 70 ° C, 225 g of polyoxyethylene monomethyl ether (molecular weight: 450) was mixed and maintained for 2 hours. 57 g of epsilon caprolactam was added and reacted for 2 hours. The emke was volatilized in a drying oven A 99.8% brown liquid type blocked reactive surfactant was prepared.

[Production Example 2]

A thermometer, a condenser, a stirrer, a condenser and a temperature raising device were attached to a 2 liter four-necked flask. 350 g of EMK and 87 g of toluene diisocyanate were mixed and the mixture was heated to 70 DEG C with gentle stirring. 165 g of polyoxyethylene lauryl ether (molecular weight 550) was added and kept at this temperature for 2 hours. 80 g of dessicone caprolactam was added and reacted for 2 hours. The emulsion was volatilized in a drying oven to give 99.7 % Of a brown liquid type blocked reactive surfactant was prepared.

[Production Example 3]

A thermometer, a condenser, a stirrer, a condenser and a temperature raising device were attached to a 2 liter four-necked flask. 500 g of EMK, and 333 g of hexamethylene diisocyanate trimer desmodern 3300 (isocyanate%: 21.8, manufactured by Bayer AG) were mixed and the mixture was heated to 70 ° C with gentle stirring. 180 g of polyoxyethylene monomethyl ether (molecular weight: 450) was mixed and kept for 2 hours, then 53 g of emkeoxime was added and reacted for 2 hours. The emke was volatilized in a drying furnace to obtain nonvolatile matter To obtain a 99.8% blocked liquid surfactant in the form of a blocked reactive surfactant.

[Production Example 4]

A thermometer, a condenser, a stirrer, a condenser and a temperature raising device were attached to a 2 liter four-necked flask. 500 g of EMK, and 333 g of hexamethylene diisocyanate trimer desmodern 3300 (isocyanate%: 21.8, manufactured by Bayer AG) were mixed and the mixture was heated to 70 ° C with gentle stirring. After the temperature reached 70 占 폚, 225 g of polyoxyethylene / propylene mixed monomethyl ether (molecular weight: 750) was mixed and maintained for 2 hours, then 80 g of epsilon caprolactam was added and reacted for 2 hours and the emke was volatilized in a drying oven A blocked liquid type surfactant with a nonvolatile content of 99.8% was prepared.

[Examples 1 to 8 and Comparative Example]

Dispersion of the polyfunctional block isocyanate using a surfactant in the weight part composition shown in Table 1 below was performed to prepare an aqueous dispersion isocyanate. Blocked methylene diphenyl diisocyanate (100%) blocked with epsilon caprolactam was used as the water-dispersed polyfunctional block isocyanate. Comparative Examples were prepared by adding water-dispersed polyoxyethylene / propylene mixed monomethyl ether (molecular weight: 750) as a non-reactive nonionic surfactant in place of the blocked reactive surfactants of Production Examples 1 to 4.

division Polyfunctional block isocyanate Distilled water Production Example 1 Production Example 2 Production Example 3 Production Example 4 Non-reactive nonionic surfactant Example 1 50 40 10 - - - Example 2 52 40 4 - - 4 - Example 3 53 40 - 4 3 - - Example 4 52 40 8 - - - - Example 5 52 40 - - - 8 - Example 6 53 40 - 7 - - - Example 7 53 40 - - 7 - - Example 8 50 40 - 10 - - - Comparative Example 57 40 - - - - 3

Test Example

≪ Preparation of Composition for Adhesion and Tire Cord >

In order to confirm the physical properties of Examples 1 to 8 and Comparative Examples, a bonding composition and a tire cord using the same were prepared. 20 parts by weight of an epoxy resin containing 5 parts by weight of an aqueous dispersion isocyanate compound of each of the Examples and Comparative Examples and 100 parts by weight of an RFL adhesive were mixed to prepare a bonding composition for a tire cord, To produce a polyester tire cord. The results of measuring the physical properties of the water-dispersed isocyanates of Examples 1 to 8 and Comparative Examples and tire cords prepared using the same are shown in Table 2 below. For reference, in Table 2, " & cir & is very good, " is good, "

division Dispersibility Dispersion stability Initial adhesion Heat-resistant adhesion Example 1 ◎ ◎ ◎ ○ Example 2 ◎ ◎ ◎ ◎ Example 3 ◎ ○ ◎ ○ Example 4 ◎ ○ ◎ ○ Example 5 ◎ ◎ ◎ ◎ Example 6 ◎ ○ ◎ ○ Example 7 ◎ ○ ◎ ○ Example 8 ◎ ◎ ◎ ○ Comparative Example ◎ ○ ○ X

<Evaluation Method and Evaluation Standard>

1. DISTRIBUTION: DYNO-MILL is used to measure the time it takes for the particle size to reach 2.5 microseconds. Very good for less than 2 hours, better than 2 hours to less than 3 hours, better than 3 hours to less than 4 hours , And more than 4 hours were judged as bad.

2. Dispersion Stability: Very good for more than 30 days by measuring the time taken to separate and precipitate by water-dispersed block isocyanate at normal temperature, good range from 20 days to less than 30 days, range from 10 days to less than 20 days , And less than 10 days were judged as bad.

3. Initial Adhesion: The rubber was arranged on the upper layer of the cord in the middle of the lower layer rubber in the mold, and the layer was vulcanized at a temperature of 120 ° C and then tensile strength was measured. More detailed methods were measured according to ASTM D885 H test. The evaluation criteria were as follows: good at more than 15 kgf / cm 2, good at 13 to 15 kgf / cm 2, less than 11 kgf / cm 2 at 13 kgf / cm 2 and less than 11 kgf / cm 2.

4. Thermal Adhesion: The initial adhesion was measured in the same manner as above, but the vulcanization temperature and time were 170 ° C and 40 minutes. The evaluation criteria are as follows: 90% or more of the initial adhesion is very good, 80% to less than 90% is good, 70% to less than 80% is usually evaluated, and less than 70% is poor.

In Table 2, it can be seen that Examples 1 to 8, which were water-dispersed using the surfactant according to the present invention, had a superior adhesive force and a remarkably improved heat-resistant adhesive force as compared with Comparative Examples.

Claims (7)

Isocyanate, polyoxyethylene monomethyl ether, polyoxypropylene monomethyl ether, polyoxyethylene / propylene mixed type monomethyl ether, polyoxyethylene cetyl ether, polyoxyethylene lauryl ether, polyoxyethylene oleyl ether, polyoxyethylene stearate But are not limited to, alkyl ethers, aryl ethers, polyoxyethylene tridecyl ethers, polyoxyethylene decyl ether, polyoxyethylene phenyl ether, polyoxyethylene octyl ether, polyoxyethylene caster ether, polyoxyethylene monomethyl ester, polyoxypropylene monomethyl ester, Ethylene / propylene mixed monomethyl esters, polyoxyethylene cetyl esters, polyoxyethylene lauryl esters, polyoxyethylene oleyl esters, polyoxyethylene stearyl esters, polyoxyethylene tridecyl esters, polyoxyethylene decyl esters, A first step of adding at least one selected from the group consisting of polyoxyethylene phenyl ester, polyoxyethylene octyl ester and polyoxyethylene caster ester at an equivalent ratio of 1: 0.3 to 0.7 to effect a first reaction;
A second step of synthesizing a blocked reactive surfactant by adding a blocking agent to the reactant prepared in the first step; And
And a third step of water-dispersing the surfactant synthesized in the second step in the multifunctional block isocyanate, wherein the water-dispersed isocyanate has excellent heat-
In the third step, the polyfunctional block isocyanate is contained in an amount of 45 to 55% by weight based on 100% by weight of the total amount of the water-dispersed isocyanate to be produced,
Wherein the surfactant is administered in an amount of 5 to 15% by weight based on 100% by weight of the total amount of the water-dispersed isocyanate to be produced.
The process according to claim 1, wherein the polyoxyethylene monomethyl ether, polyoxypropylene monomethyl ether, mixed polyoxyethylene / propylene monomethyl ether, polyoxyethylene cetyl ether, polyoxyethylene lauryl ether, polyoxyethylene oleyl ether , Polyoxyethylene stearyl ether, polyoxyethylene tridecyl ether, polyoxyethylene tridecyl ether, polyoxyethylene decyl ether, polyoxyethylene phenyl ether, polyoxyethylene octyl ether, polyoxyethylene caster ether, polyoxyethylene mono Methyl esters, polyoxypropylene monomethyl esters, polyoxyethylene / propylene mixed monomethyl esters, polyoxyethylene cetyl esters, polyoxyethylene lauryl esters, polyoxyethylene oleyl esters, polyoxyethylene stearyl esters, polyoxyethylene Tridecyl At least one selected from the group consisting of terpol, polyoxyethylene tridecyl ester, polyoxyethylene decyl ester, polyoxyethylene phenyl ester, polyoxyethylene octyl ester and polyoxyethylene caster ester has a weight average molecular weight of 300 to 5,000 Wherein the water-dispersed isocyanate has excellent heat-resistant adhesiveness.
delete The method according to claim 1, wherein the blocking agent comprises at least one selected from the group consisting of epsilon caprolactam, delta valerolactam, butyl cellosolve, phenol, cresol, resorcinol and emkeoloxime Dispersible isocyanate having excellent heat-resistant adhesiveness.
The method for producing water-dispersed isocyanate according to claim 1, wherein the blocking agent in the second step is added in an equivalent ratio of 1: 0.3 to 0.7 to the isocyanate of the first step.
delete A water-dispersed isocyanate excellent in heat-resistant adhesiveness, which is produced by the production method of any one of claims 1, 2, 4 and 5.