KR20150117915A - A novel compound, a method for preparing the same and a curing agent comprising the same - Google Patents

Abstract

The present invention relates to a novel compound, a producing method thereof and a curing agent comprising the same. Disclosed are a compound comprising an amide bond and an aziridin group in a molecule by reacting a compound having one or more isocyanate groups with a compound comprising an aziridin group, and a curing agent comprising the same. According to the present invention, provided is a curing agent having a long pot life and a short aging time when being mixed with a main agent.

Description

TECHNICAL FIELD The present invention relates to a novel compound, a process for producing the same, and a curing agent containing the same.

The present invention relates to a novel compound, a process for producing the same, and a curing agent containing the same. More particularly, the present invention relates to a compound containing an amide bond and an aziridine group in a molecule, a process for producing the same, and a curing agent containing the same.

Generally, the hardener is difficult to work because it is limited in use time (or also called "pot life") after it is mixed with the main agent. Such hardener is completely hardened even after coating on the substrate The time required for aging, that is, the aging time is required. The aging time for a long time is a factor for lowering the productivity.

In the prior art, various thermosetting products have been proposed in order to shorten the aging time which is directly related to productivity. However, the conventional curing agent is shortened in aging time by shortening the aging time, which is inconvenient to use in actual work, and accordingly, there is a disadvantage that consumption of the curing agent is increased.

Korean Patent Laid-Open No. 10-2008-0039740 discloses an acrylic adhesive in which an alkyl (meth) acrylic acid ester monomer and a photoinitiator-containing monomer are copolymerized. However, since a photo initiator-containing monomer is contained in the polymerization reaction, There is a problem that occurs.

Korean Patent Laid-Open No. 10-2008-0062642 discloses an acrylic copolymerized binder derived from a monomer having a carboxyl group and a hydroxyl group by reacting glycidyl methacrylate and reacting isocyanato (meth) acrylate with a hydroxyl group to form an adhesive And a method for producing the same.

Korean Patent Publication No. 10-2010-0003717 and Korean Patent Publication No. 10-2010-0008748 disclose a photopolymerizable group having an isocyanate terminal, a silane terminal, or a glycidyl terminal terminal after a functional group such as a hydroxyl group or a carboxy group is added to the polymer main chain or And a second reaction with a radiation-polymerizable group-containing compound.

However, these prior art documents require an additional reaction time of about 2 to 4 hours at 60 캜 when the acrylic copolymer is reacted with the photopolymerizable group or the radiation polymerizable group-containing compound, resulting in poor processability.

Korean Patent No. 10-2011-0125480 discloses an adhesive composition in which a photopolymerizable group-containing compound containing an aziridine group and a double bond in a molecule and an acrylic copolymer having a polar functional group are mixed. However, this prior art has difficulty in the process to be irradiated with UV, and the crosslinking density after curing is formed to be low. Such cross-linking density affects the adhesive strength, re-peeling property, heat resistance and durability of the adhesive, so that the adhesive which is not sufficiently crosslinked has a problem of deteriorating the physical properties.

SUMMARY OF THE INVENTION The present invention has the following objectives to solve the above problems.

A first object of the present invention is to provide a novel compound comprising an amide bond (-NHCO-) and an aziridine group in a molecule.

A second object of the present invention is to provide a process for preparing the novel compound by reacting a compound having at least one isocyanate group in the molecule with a compound having an aziridine group in the molecule.

A third object of the present invention is to provide a curing agent comprising the novel compound.

In order to accomplish the above first object, a first aspect of the present invention provides a compound represented by the following formula 1:

≪ Formula 1 >

In Formula 1,

R is a substituted or unsubstituted C1-C20 aliphatic hydrocarbon, a substituted or unsubstituted C6-C20 aromatic hydrocarbon, or a substituted or unsubstituted C3-C20 aliphatic hydrocarbon ring or a combination thereof, and the aliphatic hydrocarbon and the aliphatic hydrocarbon ring Containing or not containing a nitrogen atom, further comprising or not including a ketone group or an ether group,

A is independently a hydrogen atom or a substituted or unsubstituted C1-C12 alkyl group,

n is an integer of 1 to 4;

In one embodiment according to the first aspect of the present invention, in Formula 1, R may be an unsubstituted C1-C20 aliphatic hydrocarbon, an unsubstituted C3-C20 aliphatic hydrocarbon ring or a combination thereof, And the aliphatic hydrocarbon ring may contain a nitrogen atom and a ketone group; And n may be an integer of 2 to 4.

In another embodiment according to the first aspect of the present invention, in the R and A described in the above-mentioned Formula 1, the aliphatic hydrocarbon, the aromatic hydrocarbon, and the aliphatic hydrocarbon ring and the substituent when the alkyl group is substituted are each independently A C1-C6 alkyl group and a C1-C6 alkoxy group.

In order to achieve the second object, a second aspect of the present invention is a process for producing a compound represented by the formula (1), comprising reacting an isocyanate group-containing compound represented by the following formula (2) with an aziridine group- Lt; / RTI >

In the above scheme, R, A and n are as defined above.

In one embodiment according to the second aspect of the present invention, the compound of Formula 2 is selected from the group consisting of ethyl isocyanate, propyl isocyanate, butyl isocyanate, pentyl isocyanate, hexyl isocyanate, heptyl isocyanate, octyl isocyanate, nonyl isocyanate, decyl isocyanate, undecyl isocyanate, Examples of the isocyanate compound include at least one selected from the group consisting of dodecyl isocyanate, tridecyl isocyanate, tetradecyl isocyanate, pentadecyl isocyanate, hexadecyl isocyanate, heptadecyl isocyanate, octadecyl isocyanate, dimethylene diisocyanate, trimethylene diisocyanate, tetramethylene diisocyanate, Diisocyanate, heptamethylene diisocyanate, octamethylene diisocyanate, nonamethylene diisocyanate, decamethylene diisocyanate But are not limited to, ethylene glycol diisocyanate, hexamethylene diisocyanate, hexamethylene diisocyanate, undecamethylene diisocyanate, dodecamethylene diisocyanate, tridecamethylene diisocyanate, tetradecamethylene diisocyanate, pentadecamethylene diisocyanate, hexadecamethylene diisocyanate, heptadecamethylene diisocyanate, 2-phenylenediisocyanate, 1,3-phenylene diisocyanate, 1,4-phenylene diisocyanate, o-xylylene diisocyanate, m-xylylene diisocyanate, p-xylylene diisocyanate, Toluene diisocyanate, 2,6-toluene diisocyanate, poly (hexamethylene diisocyanate), isophorone diisocyanate, 2-isocyanatoethyl methacrylate, trans-1, 4-cyclohexylene diisocyanate, 3,3'-dimethoxy-4,4'-biphenylene di (Isocyanato-1-methylethyl) benzene, 3,3'-dimethyldiphenylmethane-4,4'-diisocyanate, 4,4'-methylenebis Isocyanate), and (2,4,6-trioxotriazine-1,3,5 (2H, 4H, 6H) -triyl) tris (hexamethylene) isocyanate.

In another embodiment according to the second aspect of the present invention, the compound of formula 3 described in the above scheme may be ethyleneimine or propyleneimine.

In order to achieve the third object, a third aspect of the present invention provides a curing agent comprising a compound represented by the following general formula (1).

≪ Formula 1 >

In Formula 1, R, A, and n are as defined above.

In one embodiment of the present invention, the mixing ratio of the compound of Formula 1 to the solvent may be 5 to 75% by weight.

In another embodiment according to the third aspect of the present invention, the mixing ratio of the compound of Formula 1 to the solvent may be 10 to 50% by weight.

The curing agent of the present invention can be prepared by mixing an acrylic copolymer having a polar functional group (for example, -OH or -COOH) at a room temperature with a long pot life of more than about 10 hours, It has excellent aging time and productivity. Also, since the curing agent of the present invention can be easily applied to an acrylic adhesive containing a carboxyl group and a hydroxy group, it is usefully applied to industrial double-sided tape, medical band and metal plate, surface protective film for plastic, display and mobile materials, And can be applied to a coating material for surface treatment.

1 shows infrared spectroscopic analysis data of (2,4,6-trioxotriazine-1,3,5 (2H, 4H, 6H) -triyl) tris (hexamethylene) isocyanate before synthesis in the production example .
Fig. 2 shows infrared spectrophotometric analysis data of the highly functional curing agent synthesized in Production Example.
Fig. 3 shows thermogravimetric analysis (TGA) data of the high-performance curing agent synthesized in Production Example.

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

The compound according to the first aspect of the present invention is represented by the following formula (1).

≪ Formula 1 >

In Formula 1,

R is a substituted or unsubstituted C1-C20 aliphatic hydrocarbon, a substituted or unsubstituted C6-C20 aromatic hydrocarbon, or a substituted or unsubstituted C3-C20 aliphatic hydrocarbon ring or a combination thereof, and the aliphatic hydrocarbon and the aliphatic hydrocarbon ring Containing or not containing a nitrogen atom, further comprising or not including a ketone group or an ether group,

A is independently a hydrogen atom or a substituted or unsubstituted C1-C12 alkyl group,

n is an integer of 1 to 4;

The "C1-C20 aliphatic hydrocarbon" described in this specification means a monovalent to tetravalent radical having 1 to 20 carbon atoms and being a linear or branched chain, preferably 1 to 10 carbon atoms. The aliphatic hydrocarbon is, for example, an alkyl, an alkenyl, an alkynyl, an alkylene, an alkenylene or the like and specifically denotes an alkyl group such as an ethyl, a propyl, a butyl, a pentyl, a hexyl, a heptyl, an octyl, a nonyl, a decyl, Tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, and the like, but are not limited thereto.

The "C6-C20 aromatic hydrocarbon" described in the present specification means a monovalent to tetravalent radical having 6 to 20 carbon atoms and an aromatic monocyclic ring or a fused ring, and is preferably 6 to 10 carbon atoms. The aromatic hydrocarbon may be, for example, aryl, arylene or the like, and specifically includes phenyl, biphenyl, phenylene, tolyl, tolylene, o-xylyl, m-xylyl, p- It is not limited.

"C3-C20 aliphatic hydrocarbon ring" as used herein means a monovalent to tetravalent radical of a single or multi-ring having 3 to 20 carbon atoms and is preferably 3 to 10 carbon atoms. The aliphatic hydrocarbon ring may be, for example, cycloalkyl, cycloalkylene, and the like, and specifically includes, but is not limited to, cyclopentyl, cyclohexyl, and the like.

The aliphatic hydrocarbon and aliphatic hydrocarbon rings described in this specification may contain a hetero atom, for example, a nitrogen atom, and may further include, for example, a ketone group or an ether group as a functional group.

As used herein, "C1-C12 alkyl" means straight or branched chain alkyl having 1 to 30 carbon atoms, preferably 1 to 6 carbon atoms.

In the above formula (1), R is preferably an unsubstituted C1-C20 aliphatic hydrocarbon and an unsubstituted C3-C20 aliphatic hydrocarbon ring or a combination thereof, more preferably an unsubstituted C1-C10 aliphatic hydrocarbon and an unsubstituted Lt; RTI ID = 0.0 > C3-C10 < / RTI > aliphatic hydrocarbon ring; The aliphatic hydrocarbon ring further includes a nitrogen atom and a ketone group.

In Formula 1, A is preferably a C1-C6 alkyl group.

In the above formula (1), n is preferably an integer of 2 to 4, more preferably 3.

Specifically, in the formula (1), when n is an integer of 2 or more, two or more urea groups may be bonded to the same atom in R, or may be bonded to different atoms, respectively.

In the above formula (1), when the aliphatic hydrocarbon, the aromatic hydrocarbon, the aliphatic hydrocarbon ring, and the alkyl group are substituted, each substituent may independently be at least one selected from a C1-C6 alkyl group and a C1-C6 alkoxy group.

The process according to the second aspect of the present invention comprises reacting an isocyanate group-containing compound represented by the following general formula (2) with an aziridine group-containing compound represented by the following general formula (3).

In the above scheme, R, A and n are as defined above.

In the above reaction formula, specifically, when n is 1, the compound of the formula (2) is, for example, an isocyanate such as ethyl isocyanate, propyl isocyanate, butyl isocyanate, pentyl isocyanate, hexyl isocyanate, heptyl isocyanate, octyl isocyanate, nonyl isocyanate, decyl isocyanate Tetradecyl isocyanate, pentadecyl isocyanate, hexadecyl isocyanate, heptadecyl isocyanate, octadecyl isocyanate, and the like, but is not limited thereto.

In addition, when n is 2, the compound of formula (2) is, for example, selected from the group consisting of dimethylene diisocyanate, trimethylene diisocyanate, tetramethylene diisocyanate, pentamethylene diisocyanate, hexamethylene diisocyanate, heptamethylene diisocyanate, But are not limited to, isocyanate, isocyanate, nonamethylene diisocyanate, decamethylene diisocyanate, undecamethylene diisocyanate, dodecamethylene diisocyanate, tridecamethylene diisocyanate, tetradecamethylene diisocyanate, pentadecamethylene diisocyanate, hexadecamethylene diisocyanate, Methylene diisocyanate, octadecamethylene diisocyanate, and the like, but are not limited thereto.

In the above reaction formula, when n is 2 and R is a substituted or unsubstituted C6-C20 aromatic hydrocarbon, the compound of the formula (2) is, for example, 1,2-phenylene diisocyanate, 1,3-phenylene Diisocyanate, 1,4-phenylene diisocyanate, o-xylylene diisocyanate, m-xylylene diisocyanate, p-xylylene diisocyanate, 2,4-toluene diisocyanate, 2,5-toluene diisocyanate, 2 , 6-toluene diisocyanate, and the like, but are not limited thereto.

Compounds of formula (2) other than those described above include, for example, poly (hexamethylene diisocyanate), isophorone diisocyanate, 2-isocyanatoethyl methacrylate, trans-1,4- 3,3'-dimethoxy-4,4'-biphenylene diisocyanate, 1,3-bis (1-isocyanato-1-methylethyl) benzene, , 4'-diisocyanate, 4,4'-methylenebis (phenylisocyanate), (2,4,6-trioxotriazine-1,3,5 (2H, 4H, 6H) Methylene) isocyanate, and the like, but is not limited thereto.

Specifically, in the above scheme, the compound of formula (2) includes, but is not limited to, for example, a compound represented by the following formula:

In the above reaction formula, the compound of Formula 3 may be, for example, ethyleneimine, propyleneimine, or the like, but is not limited thereto.

In the above reaction formula, the synthesis temperature of the compound of formula (1) may be 0 to 20 ° C, preferably 10 to 15 ° C. At a temperature lower than 0 ° C, the reaction time is prolonged and productivity decreases. At a temperature higher than 20 ° C, the reaction temperature is lowered due to the heat of reaction due to the exothermic reaction occurring in the reaction, . Therefore, it is preferable that the reaction is carried out by flowing the refrigerant into the reactor and checking the reaction temperature since it is a suitable reaction at a temperature below room temperature.

Preferably, the reaction is carried out in a solvent. The order of introduction of the compound of Formula 2 and the compound of Formula 3 into the solvent is not particularly limited. In one specific embodiment, the isocyanate group-containing compound of formula (2) is added to the solvent and then the aziridine group-containing compound of formula (3) is slowly added dropwise to restrict the exothermic reaction. When the addition of the compound is completed, the reaction is terminated by further stirring for about 1 hour.

In the above reaction formula, the amount of the isocyanate group-containing compound of formula (2) and the aziridine group-containing compound of formula (3) corresponds to the number of isocyanate groups contained per molecule of the compound containing one mole of the isocyanate group- The mole number of the aziridine group-containing compound of formula (3) must be reacted. For example, when the isocyanate group-containing compound of the formula (2) is a diisocyanate containing two isocyanate groups per molecule, it is necessary to react two moles of the aziridine group-containing compound of the formula (3) per 1 mole of the diisocyanate compound. When the isocyanate group-containing compound of the formula (2) is triisocyanate containing three isocyanate groups per molecule, 3 moles of the aziridine group-containing compound of the formula (3) should be reacted per 1 mole of the triisocyanate compound.

The curing agent according to the third aspect of the present invention is a high-performance curing agent containing the compound of the formula (1).

The curing agent of the present invention may contain a compound of the formula (I) alone or in combination of a plurality of compounds of the formula (I), and may further include additives commonly used in addition to the compound of the formula (I). The kind of such additives is not particularly limited and may vary depending on the desired properties.

In the preparation of the highly functional curing agent of the present invention, the appropriate mixing ratio of the compound of formula (1) to the solvent may be 5 to 75% by weight. When the mixing ratio of the compound of the formula (1) is less than 5% by weight, the productivity of the curing agent is lowered and the production cost is increased. When the mixing ratio exceeds 75% by weight, the reaction heat is increased during the production of the curing agent, The purity is reduced. Preferably, the mixing ratio of the compound of the formula (1) to the solvent is 10 to 50% by weight.

Any solvent suitable for the above reaction can be used as long as it is a solvent capable of dissolving a highly functional curing agent synthesized with an isocyanate group-containing compound and an aziridine group-containing compound in a well-dissolved state. Solvents for the above reaction include, for example, acetone and ethyl acetate.

In the above reaction, the humidity in the air is also important. When the humidity in the air is high, the water content of the curing agent of the present invention increases, and a side reaction occurs during the crosslinking reaction with the subject, so that desired crosslinking reaction can not be obtained. Therefore, it is preferable to control the humidity in the air to a relative humidity of less than 50% by using a constant temperature and humidity chamber during the reaction.

The high-performance curing agent containing the compound of Formula 1 can be applied to any system capable of nucleophilic cross-linking reaction by ring opening of an aziridine group. For example, if the subject has a functional group such as an amino group (-NH ₂ ), a hydroxy group (-OH) and a carboxyl group (-COOH), it can easily perform a crosslinking reaction without a catalyst and can act as a curing agent.

Since the curing agent of the present invention has a long pot life and a short aging time, it is excellent in productivity and easily applied to an acrylic adhesive containing a carboxyl group and a hydroxyl group, so that the surface protection for industrial double-sided tape, medical band and metal plate, plastic, Film, film used for semiconductors, and the like, and can be applied to a coating material for surface treatment.

Hereinafter, the compound of the present invention, a method for producing the same, and a curing agent containing the same will be described in more detail in Examples, but the present invention is not limited to the following Examples.

* glue

R-118, R-040B, and R-080 of Aekyung Chemtech Co., Ltd., which are domestic manufacturers, were used as an adhesive agent in the embodiment of the present invention.

* Viscosity measurement

In the examples of the present invention, viscosity was measured by mixing a certain amount of a curing agent in a main adhesive agent, followed by measurement at regular time intervals at room temperature. A Brookfield viscometer (Model: Digital Viscometer DV-I Prime) was used as a measuring device.

* Adhesive strength measurement

In the embodiment of the present invention, the equipment used for measuring the adhesive force is 'K-OPC' model of 'Kyung Jin Hitech Co., Ltd.'.

Manufacturing example

Ethyl acetate was added to the reactor equipped with a stirrer and 1 equivalent of (2,4,6-trioxotriazine-1,3,5 (2H, 4H, 6H) -triyl) tris (hexamethylene) isocyanate was added to dissolve . Thereafter, the temperature in the reactor was maintained at 10 캜 and 3 equivalents of propyleneimine, which is an aziridine group-containing compound, was slowly added thereto using a dropper. After the addition was completed, the mixture was further stirred for about 1 hour to prepare a high-performance curing agent.

Data analyzed by an infrared spectrophotometer of (2,4,6-trioxotriazine-1,3,5 (2H, 4H, 6H) -triyl) tris (hexamethylene) isocyanate prior to synthesis in the preparation example The data analyzed by the infrared spectrophotometer of the highly functional curing agent after synthesis shown in FIG. 1 are shown in FIG. When the reaction is not completed and unreacted (2,4,6-trioxotriazine-1,3,5 (2H, 4H, 6H) -triyl) tris (hexamethylene) isocyanate is present, 2,200 A strong peak appears at ~ 2,300 wavenumbers, and this peak does not appear when the reaction is complete. FIG. 3 shows thermogravimetric analysis (TGA) data of the highly functional curing agent after synthesis.

The thermogravimetric analysis (TGA) was performed on a thermogravimetric analyzer (TA Instrument, model name: Q50) for the highly functional curing agent after synthesis. Specifically, the sample was subjected to a thermal analysis at room temperature and at a rate of 10 ° C / And the weight change was observed by heating to a final temperature of about 900 < 0 > C.

Referring to FIG. 3, it is confirmed that the curing agent is thermally stable to at least 200 ° C.

Example  One

The 'R-118' adhesive purchased from Aekyung Chemtech Co., Ltd. was mixed with ethyl acetate and diluted to a solid content of 10%. Then, 100 parts by weight of the curing agent prepared in Preparation Example 1 was mixed to 4.5 phr. Then, the viscosity of the mixture was measured at room temperature and the pot life was measured at intervals of 1 hour.

Example  2

The 'R-040B' adhesive purchased from Aekyung Chemtech Co., Ltd. was mixed with ethyl acetate and diluted to a solid content of 10%. Then, 100 parts by weight of the curing agent prepared in Preparation Example 1 was mixed to 4.5 phr. Then, the viscosity of the mixture was measured at room temperature and the pot life was measured at intervals of 1 hour.

Example  3

The 'R-080' adhesive purchased from Aekyung Chemtech Co., Ltd. was mixed with ethyl acetate and diluted to a solid content of 10%. Then, 100 parts by weight of the curing agent prepared in Preparation Example 1 was mixed to 4.5 phr. Then, the viscosity of the mixture was measured at room temperature and the pot life was measured at intervals of 1 hour.

Example  4

The adhesive composition prepared in Example 1 was dried on a PET film (thickness 50 탆) and coated to a thickness of 20 탆 to measure the adhesive strength.

Example  5

The adhesive composition prepared in Example 2 was dried on a PET film (thickness 50 탆) and coated to a thickness of 20 탆 to measure the adhesive strength.

Example  6

The adhesive composition prepared in Example 3 was dried on a PET film (thickness 50 탆) and coated to a thickness of 20 탆 to measure the adhesive strength.

Comparative Example  One

An adhesive mixture was prepared in the same manner as in Example 1 except that trimethylolpropane tris (2-methyl-1-aziridine propionate) (CAS. 64265-57-2) was used as a curing agent.

Comparative Example  2

An adhesive mixture was prepared in the same manner as in Example 2, except that trimethylolpropane tris (2-methyl-1-aziridine propionate) (CAS. 64265-57-2) was used as a curing agent.

Comparative Example  3

An adhesive mixture was prepared in the same manner as in Example 3, except that trimethylolpropane tris (2-methyl-1-aziridine propionate) (CAS. 64265-57-2) was used as a curing agent.

Comparative Example  4

The adhesive composition prepared in Comparative Example 1 was dried on a PET film (thickness 50 탆) and coated to a thickness of 20 탆 to measure the adhesive strength.

Comparative Example  5

The adhesive composition prepared in Comparative Example 2 was dried on a PET film (thickness 50 탆) and coated to a thickness of 20 탆 to measure the adhesive strength.

Comparative Example  6

The adhesive composition prepared in Comparative Example 3 was dried on a PET film (thickness 50 탆) and coated to a thickness of 20 탆 to measure the adhesive strength.

The results of viscosity measurements of Examples 1-3 and Comparative Examples 1-3 are shown in Table 1 below, and the results of adhesion measurements of Examples 4-6 and 4-6 are shown in Table 2 below.

No . Example 1 Comparative Example 1 Example 2 Comparative Example 2 Example 3 Comparative Example 3 glue
(PSA) Solids
(%) 10 10 10 10 10 10 Hardener
ratio phr 4.5 4.5 4.5 4.5 4.5 4.5 Time Viscosity( cps )
1 hours
1,230
1,263
1,222
1,238
1,243     1,269
2 hours     1,246     1,354     1,227     1,250     1,252     1,291
3 hours     1,265     1,479     1,234     1,265     1,262     1,345
4 hours     1,287     1,632     1,244     1,285     1,273     1,440
5 hours     1,314     1,846     1,258     1,311     1,287     1,645
6 hours     1,348     2,234     1,277     1,346     1,305     1,904
7 hours     1,391     2,752     1,301     1,394     1,330     2,347
8 hours     1,449     3,566     1,331     1,459     1,366     2,885
9 hours     1,526     4,538     1,368     1,547     1,415     3,459
10 hours     1,628
Gel     1,413     1,670     1,479     4,332
11 hours     1,770     1,467     1,859     1,574
Gel
12 hours     1,920     1,531     2,152     1,710
24 hours
Gel     3,560
Gel     4,837

No . Example 1 Comparative Example 1 Example 2 Comparative Example 2 Example 3 Comparative Example 3 glue
(PSA) Solids
(%) 10 10 10 10 10 10 Hardener
ratio phr 4.5 4.5 1.0 1.0 4.5 4.5 Time Adhesion ( gf / 25 mm ) 30 minutes 47 43 13 14 11 10 1 day 80 62 17 16 13 12 2 days 81 78 17 18 13 14 3 days 81 81 17 19 13 14

In Table 1, when the viscosity measurement results of Example 1, Comparative Example 1, and Example 3 and Comparative Example 3 were compared, in Example 1, the gel was formed after 24 hours from the production of the adhesive composition, 3 did not form a gel after 24 hours from the preparation of the adhesive composition. On the other hand, in Comparative Example 1, the gel was formed 10 hours after the preparation of the adhesive composition, and in Comparative Examples 2 and 3, the gel was formed only 24 hours and 11 hours after the preparation of the adhesive composition, As a result of 7 to 8 hours after the preparation, the viscosity was much higher than those of Examples 1 to 3 and the productivity was lowered. Thus, Examples 1 to 3 have a longer pot life of more than 10 hours, which exceeds the working time of one day, but Comparative Examples 1 to 3 have a pot life of only about half of Examples 1 to 3.

In Table 2, when the results of the adhesion measurements of Examples 1 to 3 and Comparative Examples 1 to 3 were compared, all of Examples 1 to 3 showed stable adhesion within one day, but Comparative Example 3 required stable adhesion And Comparative Examples 1 and 2 did not exhibit stable adhesion even after 3 days from the measurement. Thus, Examples 1 to 3 according to the present invention have an aging time within 24 hours, while Comparative Examples 1 to 3 have aging times twice or more of the aging time of Examples 1 to 3.

Thus, it was confirmed that the adhesive composition using the compound according to the present invention as a curing agent has a longer pot life and shorter aging time than the conventional adhesive composition, and thus shows excellent productivity.

Claims (9)

A compound represented by the following formula (1):
≪ Formula 1 >

In Formula 1,
R is a substituted or unsubstituted C1-C20 aliphatic hydrocarbon, a substituted or unsubstituted C6-C20 aromatic hydrocarbon, or a substituted or unsubstituted C3-C20 aliphatic hydrocarbon ring or a combination thereof, and the aliphatic hydrocarbon and the aliphatic hydrocarbon ring Containing or not containing a nitrogen atom, further comprising or not including a ketone group or an ether group,
A is independently a hydrogen atom or a substituted or unsubstituted C1-C12 alkyl group,
n is an integer of 1 to 4; 2. The method of claim 1, wherein R is an unsubstituted C1-C20 aliphatic hydrocarbon, an unsubstituted C3-C20 aliphatic hydrocarbon ring, or a combination thereof, wherein the aliphatic hydrocarbon and the aliphatic hydrocarbon ring comprise a nitrogen atom and a ketone group; Wherein n is an integer of 2 to 4. The compound according to claim 1, wherein the aliphatic hydrocarbon, the aromatic hydrocarbon, the aliphatic hydrocarbon ring, and the substituent when the alkyl group is substituted are each independently at least one selected from a C1-C6 alkyl group and a C1-C6 alkoxy group. Comprising reacting an isocyanate group-containing compound represented by the following formula (2) with an aziridine group-containing compound represented by the following formula (3).

Wherein R, A and n are as defined in claim 1. 5. The composition of claim 4, wherein the compound of Formula 2 is selected from the group consisting of ethyl isocyanate, propyl isocyanate, butyl isocyanate, pentyl isocyanate, hexyl isocyanate, heptyl isocyanate, octyl isocyanate, nonyl isocyanate, decyl isocyanate, undecyl isocyanate, dodecyl isocyanate, , Tetradecylisocyanate, pentadecylisocyanate, hexadecylisocyanate, heptadecylisocyanate, octadecylisocyanate, dimethylene diisocyanate, trimethylene diisocyanate, tetramethylene diisocyanate, pentamethylene diisocyanate, hexamethylene diisocyanate, heptamethylene diisocyanate , Octamethylene diisocyanate, nonamethylene diisocyanate, decamethylene diisocyanate, undecamethylene di There may be mentioned isocyanate compounds such as isocyanate, dodecamethylene diisocyanate, tridecamethylene diisocyanate, tetradecamethylene diisocyanate, pentadecamethylene diisocyanate, hexadecamethylene diisocyanate, heptadecamethylene diisocyanate, octadecamethylene diisocyanate, 1,2-phenyl Phenylene diisocyanate, 1,4-phenylene diisocyanate, o-xylylene diisocyanate, m-xylylene diisocyanate, p-xylylene diisocyanate, 2,4-toluene diisocyanate , 2,5-toluene diisocyanate, 2,6-toluene diisocyanate, poly (hexamethylene diisocyanate), isophorone diisocyanate, 2-isocyanatoethyl methacrylate, trans-1,4-cyclohexylene Diisocyanate, 3,3'-dimethoxy-4,4'-biphenylene diisocyanate, 1,3-bis (1- 1-methylethyl) benzene, 3,3'-dimethyldiphenylmethane-4,4'-diisocyanate, 4,4'-methylenebis (phenylisocyanate), and 2,4,6- Triazine-1,3,5 (2H, 4H, 6H) -triyl) tris (hexamethylene) isocyanate. The process according to claim 4, wherein the compound of Formula 3 is ethyleneimine or propyleneimine. The process according to claim 4, wherein the reaction is carried out at a temperature of from 0 to 20 ° C. 5. The process according to claim 4, wherein the reaction is carried out at a temperature of from 10 to 15 占 폚. A curing agent comprising a compound according to any one of claims 1 to 3.

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