COMPOUND FOR RELEASE AGENT AND METHOD FOR PREPARING THE SAME

Abstract

The present invention relates to a compound for release agent and method for preparing the same, and more specifically, to a compound for a release agent that can be coated in an ultra-thin form without thermal deformation even when heat is continuously or discontinuously applied in a continuous evaporator, and a method for preparing the same.

Claims

1. A compound represented by Formula 1: ##STR00014## In Formula 1, L is an aliphatic derivative or an aromatic derivative having 1 to 20 carbon atoms; each of m and n is 0 or 1; each of R.sub.1 and R.sub.2 is independently a hydrogen atom or a derivative having 1 to 40 carbon atoms and a substituted or unsubstituted aliphatic hydrocarbon group or a perfluoro alkyl group; each of B.sub.1 and B.sub.2 is independently —O—, —COO—, —NHCOO— or a combination thereof; each of G.sub.1 and G.sub.2 is independently H, CH.sub.3, CH.sub.2A (wherein A is F, Cl, Br or I) or is omitted; and each of Y and Z is independently an alkyl group having 1 to 6 carbon atoms.

2. The compound according to claim 1, wherein the total molecular weight is 300 to 4,000 g/mol.

3. A compound represented by Formula 2: ##STR00015## In Formula 2, each of L.sub.1 and L.sub.2 is independently an aliphatic derivative or an aromatic derivative having 1 to 20 carbon atoms; each of m, n, o and p is 0 or 1; each of R.sub.1, R.sub.2, R.sub.3 and R.sub.4 is independently a hydrogen atom or a derivative having 1 to 40 carbon atoms and a substituted or unsubstituted aliphatic hydrocarbon group or a perfluoro alkyl group; each of B.sub.1, B.sub.2, B.sub.3 and B.sub.4 is independently —O—, —COO—, —NHCOO— or a combination thereof; each of G.sub.1 and G.sub.2 is independently H, CH.sub.3, CH.sub.2A (wherein A is F, Cl, Br or I) or is omitted; each of Y and Z is independently an alkyl group having 1 to 6 carbon atoms; and X is —CH.sub.2— or —O—.

4. The compound according to claim 3, wherein the total molecular weight is 300 to 4,000 g/mol.

5. A release agent comprising the compound for a release agent according to claim 1.

6. A coating method for vacuum-evaporating a release agent, comprising: continuously or discontinuously vacuum-evaporating the release agent of claim 5.

7. The coating method according to claim 6, wherein the release agent is a single compound.

8. The coating method according to claim 6, wherein the vacuum-evaporated release agent is removed using alcohols or other organic solvents having 1 to 10 carbon atoms.

9. A release agent comprising the compound for a release agent according to claim 3.

Description

BRIEF DESCRIPTION OF THE DRAWINGS

[0029] FIG. 1 is a graph showing temperature stability in a crucible, a change in thickness, and a change in a degree of vacuum in an evaporator according to time that occurs during deposition in a vacuum evaporator for Example 1 of the present invention.

[0030] FIG. 2 is a result showing a change in a material state, a contact angle of a coating surface and haze after coating during deposition by heating repeatedly several times.

DETAILED DESCRIPTION

[0031] The present invention is explained in more detail below.

[0032] The compound for a release agent of the present invention comprises a structure represented by the following Formula 1 or Formula 2:

##STR00003##

[0033] In Formula 1,

[0034] L is an aliphatic derivative or an aromatic derivative having 1 to 20 carbon atoms;

[0035] each of m and n is 0 or 1;

[0036] each of R.sub.1 and R.sub.2 is independently a hydrogen atom or a derivative having 1 to 40 carbon atoms and a substituted or unsubstituted aliphatic hydrocarbon group or a perfluoro alkyl group;

[0037] each of B.sub.1 and B.sub.2 is independently —O—, —COO—, —NHCOO— or a combination thereof;

[0038] each of G.sub.1 and G.sub.2 is independently H, CH.sub.3, CH.sub.2A (wherein A is F, Cl, Br or I) or is omitted; and

[0039] each of Y and Z is independently an alkyl group having 1 to 6 carbon atoms.

##STR00004##

[0040] In Formula 2,

[0041] each of L.sub.1 and L.sub.2 is independently an aliphatic derivative or an aromatic derivative having 1 to 20 carbon atoms;

[0042] each of m, n, o and p is 0 or 1;

[0043] each of R.sub.1, R.sub.2, R.sub.3 and R.sub.4 is independently a hydrogen atom or a derivative having 1 to 40 carbon atoms and a substituted or unsubstituted aliphatic hydrocarbon group or a perfluoro alkyl group;

[0044] each of B.sub.1, B.sub.2, B.sub.3 and B.sub.4 is independently —O—, —COO—, —NHCOO— or a combination thereof;

[0045] each of G.sub.1 and G.sub.2 is independently H, CH.sub.3, CH.sub.2A (wherein A is F, Cl, Br or I) or is omitted;

[0046] each of Y and Z is independently an alkyl group having 1 to 6 carbon atoms; and

[0047] X is —CH.sub.2— or —O—.

[0048] The compound for a release agent of the present invention may have a total molecular weight of 300 to 4,000 g/mol.

[0049] In another aspect, the present invention provides a release agent comprising the above compound for a release agent.

[0050] In still another aspect, the present invention provides a coating method for vacuum-evaporating the above release agent.

[0051] The compound for a release agent used in the present invention or the releasing agent comprising the same, should be a single compound, not a mixed phase, so that even when deposition is repeated continuously or discontinuously, the release property can be stably implemented without thermal deformation.

[0052] In addition, vacuum evaporation can be performed in a continuous or non-continuous process using the release agent prepared according to the present invention, and when the release process is performed after depositing or coating the function to be released, it can be removed using a solvent in addition to physical methods such as drying. Although not particularly limited, the release agent may be removed using alcohols having 1 to 10 carbon atoms including methyl alcohol, ethyl alcohol, propanol, butanol, pentanol, and hexanol, and other organic solvents.

[0053] The present invention is explained in more detail through the following Synthesis Examples and Examples. However, the scope of the present invention is not limited thereby in any manner.

EXAMPLES

1. Synthesis Example 1

[0054] 1,6-bis(perfluorohexylethyl urethane)hexane was prepared as follows.

[0055] In a 100 mL round bottom flask, 20 g of perfluorohexylethyl alcohol and 40 g of 1,3-bistrifluoromethylbenzene were added and stirred at room temperature for 30 minutes. 4.62 g of hexamethylene diisocyanate was added to this solution, the temperature was gradually raised to 75° C. with vigorous stirring, and a drop of dibutyl tin dilaurate catalyst was added thereto, followed by vigorous stirring for 20 hours. When it was confirmed that the isocyanate peak (2270˜2290 cm.sup.−1) disappeared from the FTIR spectrum, the mixture was cooled, the solvent and impurities were first removed using a rotary evaporator, and the solution was purified secondarily at 1 torr and 50° C. in a vacuum oven to obtain the solid content in the form of white powder. The NMR, FTIR and GC/MS spectra were consistent with the following structures.

##STR00005##

[0056] <1,6-bis(perfluorohexylethyl urethane)hexane>

2. Synthesis Example 2

[0057] 2,4-bis(perfluorohexylethylurethane)-toluene was prepared as follows.

[0058] In a 100 mL round bottom flask, 20 g of perfluorohexylethyl alcohol and 40 g of 1,3-bistrifluoromethylbenzene were added and stirred at room temperature for 30 minutes. To this solution, 4.78 g of tolylene-2-4-diisocyanate was added, the temperature was gradually raised to 75° C. with vigorous stirring, and a drop of dibutyl tin dilaurate catalyst was added thereto, followed by vigorous stirring for 20 hours. When it was confirmed that the isocyanate peak (2270˜2290 cm.sup.−1) disappeared from the FTIR spectrum, the mixture was cooled, the solvent and impurities were first removed using a rotary evaporator, and the solution was purified secondarily at 1 torr and 50° C. in a vacuum oven to obtain the solid content in the form of white powder. The NMR, FTIR and GC/MS spectra were consistent with the following structures.

##STR00006##

[0059] <2,4-bis(perfluorohexylethylurethane)-toluene>

3. Synthesis Example 3

[0060] 1,4-bis(perfluorohexylethylurethane)benzene was prepared as follows.

[0061] In a 100 mL round bottom flask, 20 g of perfluorohexylethyl alcohol and 40 g of 1,3-bistrifluoromethylbenzene were added and stirred at room temperature for 30 minutes. To this solution, 4.41 g of 1,4-phenylenediisocyanate was added, the temperature was gradually raised to 75° C. with vigorous stirring, and a drop of dibutyl tin dilaurate catalyst was added and stirred vigorously for 20 hours. When it was confirmed that the isocyanate peak (2270˜2290 cm.sup.−1) disappeared from the FTIR spectrum, the mixture was cooled, the solvent and impurities were first removed using a rotary evaporator, and the solution was purified secondarily at 1 torr and 50° C. in a vacuum oven to obtain the solid content in the form of white powder. The NMR, FTIR and GC/MS spectra were consistent with the following structures.

##STR00007##

[0062] <1,4-bis(perfluorohexylethylurethane)benzene>

4. Synthesis Example 4

[0063] Bis(4-perfluorohexylethyl urethane phenyl) was prepared as follows.

[0064] In a 100 mL round bottom flask, 20 g of perfluorohexylethyl alcohol and 40 g of 1,3-bistrifluoromethylbenzene were added and stirred at room temperature for 30 minutes. To this solution, 6.87 g of methylenediphenyldiisocyanate was added, the temperature was gradually raised to 100° C. with vigorous stirring, and a drop of dibutyl tin dilaurate catalyst was added and stirred vigorously for 20 hours. When it was confirmed that the isocyanate peak (2270˜2290 cm.sup.−1) disappeared from the FTIR spectrum, the mixture was cooled, the solvent and impurities were first removed using a rotary evaporator, and the solution was purified secondarily at 1 torr and 75° C. in a vacuum oven to obtain the solid content in the form of white powder. The NMR, FTIR and GC/MS spectra were consistent with the following structures.

##STR00008##

[0065] <Bis(4-perfluorohexylethyl urethane phenyl)methane>

5. Synthesis Example 5

[0066] 2,4-bis(2-octyl urethane)-toluene was prepared as follows.

[0067] To a 100 mL round-bottom flask, 10 g of tolylene-2,4-diisocyanate and 20 g of toluene were added and stirred at room temperature for 30 minutes. To this solution, 10 g of 2-octane was added, the temperature was gradually raised to 75° C. with vigorous stirring, stirred for 4 hours, and the temperature was raised to 90° C., followed by vigorously stirring for 16 hours. When it was confirmed that the isocyanate peak (2270˜2290 cm.sup.−1) disappeared from the FTIR spectrum, the mixture was cooled, the solvent and impurities were first removed using a rotary evaporator, and the solution was purified secondarily at 1 torr and 90° C. in a vacuum oven to obtain the solid content in the form of white powder. The NMR, FTIR and GC/MS spectra were consistent with the following structures.

##STR00009##

[0068] <2,4-bis(2-octyl urethane)-toluene>

6. Synthesis Example 6

[0069] 2,4-bis(1-dodecyl urethane) toluene was prepared as follows.

[0070] To a 100 mL round-bottom flask, 10 g of tolylene-2-4-diisocyanate and 20 g of toluene were added and stirred at room temperature for 30 minutes. To this solution, 21.40 g of 1-dodecanol was added, the temperature was gradually raised to 75° C. with vigorous stirring, and a drop of dibutyl tin dilaurate catalyst was added and stirred vigorously for 20 hours. When it was confirmed that the isocyanate peak (2270˜2290 cm.sup.−1) disappeared from the FTIR spectrum, the mixture was cooled, the solvent and impurities were first removed using a rotary evaporator, and the solution was purified secondarily at 1 torr and 75° C. in a vacuum oven to obtain the solid content in the form of white powder. The NMR, FTIR and GC/MS spectra were consistent with the following structures.

##STR00010##

[0071] <2,4-bis(1-dodecyl urethane) toluene>

7. Synthesis Example 7

[0072] 1,8-bis(perfluorohexylethyl ester) octane was prepared as follows.

[0073] To a 100 mL round bottom flask, 20 g of sebacic acid and 72.01 g of perfluorohexylethyl alcohol were added, the temperature was gradually raised to 130° C. with vigorous stirring, and 11.1 ml of concentrated sulfuric acid was added thereto and stirred vigorously for 20 hours. At this time, it was equipped to condense and remove water under a nitrogen atmosphere. After cooling to room temperature, 2 g of hydrotalcite was added to remove the acid and filtered to obtain a clear solution. Solvents and impurities were firstly removed from this clear solution using a rotary evaporator, and the solution was secondarily purified in a vacuum oven at 75° C. to obtain a white/light brown powdery solid. NMR, FTIR and GC/MS spectra were consistent with the following structures.

##STR00011##

[0074] <1,8-bis(perfluorohexylethyl ester) octane>

8. Synthesis Example 8

[0075] 1,2,3,4-tetra(perfluorohexylethyl ester) butane was prepared as follows.

[0076] In a 100 mL round bottom flask, 20 g of perfluorohexylethyl alcohol and 40 g of 1,3-bistrifluoromethylbenzene were added and stirred at room temperature for 30 minutes. To this solution, 3.21 g of 1,2,3,4-butanetetracarboxylic acid was added, the temperature was gradually raised to 110° C. with strong stirring, and 0.5 ml of concentrated sulfuric acid was added and stirred vigorously for 20 hours. At this time, a device capable of condensing and removing water under a nitrogen atmosphere was prepared. After cooling to room temperature, 2 g of hydrotalcite was added to remove the acid and filtered to obtain a clear solution. Solvents and impurities were firstly removed from this clear solution using a rotary evaporator, and the solution was secondarily purified in a vacuum oven at 75° C. to obtain a white/light brown powdery solid. NMR, FTIR and GC/MS spectra were consistent with the following structures.

##STR00012##

[0077] <1,2,3,4-tetra(perfluorohexylethyl ester) butane>

9. Synthesis Example 9

[0078] 2-Perfluorohexylethyletherethyl benzene was prepared as follows.

[0079] In a 100 mL round bottom flask, 20 g of perfluorohexylethyl alcohol and 40 g of 1,3-bistrifluoromethylbenzene were added and stirred at room temperature for 30 minutes. To this solution, 4.39 g of sodium hydroxide was added, the temperature was gradually raised to 65° C. with vigorous stirring, and the mixture was stirred vigorously for 4 hours. Then, 11.18 g of (2-bromoethyl) benzene was added, the temperature was raised to 75° C., and the mixture was vigorously stirred for 5 hours. Then, it was transferred to a separatory funnel, and 100 g of hydrochloric acid having a concentration of 3 mole was added thereto, followed by addition of 100 g of acetone, followed by washing and filtering to obtain a clear solution. Solvents and impurities were firstly removed from this clear solution using a rotary evaporator, and the solution was secondarily purified in a vacuum oven at 75° C. to obtain a white/light brown powdery solid. NMR, FTIR and GC/MS spectra were consistent with the following structures.

##STR00013##

[0080] <2-Perfluorohexylethyletherethyl benzene>

Example 1

Evaluation of Dry Vacuum Evaporation Process

[0081] Vacuum evaporation was performed using the powder prepared in Synthesis Example 2 of the above Synthesis Examples. FIG. 1 shows the relationship among a process of increasing the temperature, the change in the degree of vacuum in the vacuum evaporator during the evaporation process and the corresponding thickness increase over time by loading the powder prepared in the Synthesis Example into an effusion cell of a vacuum evaporator.

Example 2

Evaluation of Vacuum Evaporation Characteristics

[0082] Using the powder prepared in Synthesis Example 2, the process of Example 1 was repeated several times. In the process of depositing by repeated heating and cooling, the temperature at the deposition rate of 0.1 Å/sec and 4.0 Å/sec, the state before/after deposition, and the contact angle and haze at the thickness of 100 nm and 200 nm were measured and are shown in FIG. 2.