Coating Composition

Abstract

A coating composition is provided. The coating composition of the present application has excellent compatibility between the components. In addition, there is an advantage that the release layer formed from the coating composition of the present application has low transmittance for light having a wavelength of 380 nm or more.

Claims

1. A coating composition comprising a release agent; a solvent having a boiling point in a range of 79° C. to 115° C.; and a compound of Formula 1 below: ##STR00011## wherein, R.sup.1 to R.sup.5 are each independently hydrogen, an alkyl group, —OX.sup.1 or —NX.sup.1.sub.2, and one to two of R.sup.1 to R.sup.5 are —OX.sup.1 or —NX.sup.1.sub.2, where X.sup.1 is hydrogen or an alkyl group, and R.sup.6 or R.sup.7 is hydrogen, a cyano group, —C(═O)—X.sup.2, —C(═O)—O—X.sup.2, —O—C(═O)—X.sup.2, or —NO.sub.2, where X.sup.2 is an alkyl group or an aryl group.

2. The coating composition according to claim 1, wherein R.sup.3 is —OX.sup.1 or —NX.sup.1.sub.2.

3. The coating composition according to claim 2, wherein any one of R.sup.1 to R.sup.2 and R.sup.4 to R.sup.5 is —OX.sup.1.

4. The coating composition according to claim 1, wherein R.sup.6 or R.sup.7 is a cyano group, —C(═O)—X.sup.2, —C(═O)—O—X.sup.2, or —O—C(═O)—X.sup.2, where X.sup.2 is an alkyl group.

5. The coating composition according to claim 4, wherein R.sup.6 or R.sup.7 is a cyano group or —C(═O)—O—X.sup.2.

6. The coating composition according to claim 1, wherein the compound of Formula 1 is a reaction product of a compound of Formula 2 below and a compound of Formula 3 below: ##STR00012## wherein, R.sup.8 to R.sup.12 are each independently hydrogen, an alkyl group, —OX.sup.3, or —NX.sup.3.sub.2, and one to two of R.sup.8 to R.sup.12 are —OX.sup.3 or —NX.sup.3.sub.2, where X.sup.3 is hydrogen or an alkyl group; ##STR00013## wherein, R.sup.13 to R.sup.16 are each independently hydrogen, an alkyl group, a cyano group, —C(═O)—X.sup.4, —C(═O)—O—X.sup.4, —O—C(═O)—X.sup.4, or —NO.sub.2, and at least two of R.sup.13 to R.sup.16 are hydrogen, where X.sup.4 is an alkyl group or an aryl group.

7.-10. (canceled)

11. The coating composition according to claim 6, wherein the compound of Formula 1 is a reaction product, wherein the compound of Formula 3 is reacted in a range of 0.5 mol to 1.5 mol per mole of the compound of Formula 2.

12. The coating composition according to claim 1, wherein the release agent comprises a silicone resin.

13. The coating composition according to claim 12, wherein the silicone resin is an addition-curable silicone resin, a condensation-curable silicone resin or an ultraviolet-curable silicone resin.

14. The coating composition according to claim 1, wherein the release agent is included in an amount within a range of 1 wt % to 20 wt %.

15. The coating composition according to claim 1, wherein the solvent has a density in a range of 0.5 g/cm.sup.3 to 1.5 g/cm.sup.3.

16. The coating composition according to claim 1, wherein the solvent has a room temperature dielectric constant in a range of 1 to 25.

17. The coating composition according to claim 1, wherein the solvent is a mixed solvent comprising a first solvent having a boiling point of more than 100° C. and 115° C. or less.

18. The coating composition according to claim 17, wherein the mixed solvent comprises the first solvent in an amount of 50 wt % or more.

19. The coating composition according to claim 18, wherein the mixed solvent further comprises a second solvent having a boiling point of more than 85° C. and 100° C. or less in a ratio within a range of 50 parts by weight to 200 parts by weight relative to 100 parts by weight of the first solvent.

20. The coating composition according to claim 18, wherein the mixed solvent further comprises a third solvent having a boiling point of 79° C. or more and 85° C. or less in a ratio within a range of 50 parts by weight to 200 parts by weight relative to 100 parts by weight of the first solvent.

21. The coating composition according to claim 18, wherein the mixed solvent further comprises a second solvent having a boiling point of more than 85° C. and 100° C. or less in a ratio within a range of 10 parts by weight to 100 parts by weight relative to 100 parts by weight of the first solvent, and further comprises a third solvent having a boiling point of 79° C. or more and 85° C. or less in a ratio within a range of 10 parts by weight to 100 parts by weight relative to 100 parts by weight of the first solvent.

22. The coating composition according to claim 1, wherein the solvent is included in a ratio within a range of 500 parts by weight to 2000 parts by weight relative to 100 parts by weight of the release agent.

23. The coating composition according to claim 1, wherein the compound of Formula 1 is included in an amount of 0.1 parts by weight or more relative to 100 parts by weight of the release agent.

24.-29. (canceled)

Description

BRIEF DESCRIPTION OF DRAWINGS

[0101] FIG. 2 shows the NMR analysis results of the ultraviolet absorber according to Preparation Example 1.

[0102] FIG. 3 shows the NMR analysis results of Ultraviolet Absorber B (Eutec's UV-1995).

[0103] FIG. 1 shows transmittance of the release layers prepared in Examples 1 to 2 and 19 to 21 and Comparative Example 9 for each wavelength.

BEST MODE

[0104] Hereinafter, the present application will be described in more detail with reference to Examples and Comparative Examples, but the scope of the present application is not limited to Examples above.

[0105] 1. Primary Compatibility Evaluation

[0106] Turbidity of the coating compositions of Examples 1 and 2 and Comparative Examples 1 and 2 was visually observed to evaluate compatibility between the components of the composition, and the evaluation criteria are as follows.

[0107] <Evaluation Criteria>

[0108] O: No emulsion is formed, transparent

[0109] Δ: A small amount of emulsion is formed, but there is no problem in commercial use.

[0110] X: A large amount of emulsion is formed to be opaque

[0111] 2. Secondary Compatibility Evaluation

[0112] Turbidity of the coating compositions of Examples 1 to 18 and Comparative Examples 3 to 8 was visually observed to evaluate compatibility between the components of the composition. Compatibility evaluation criteria are as follows.

[0113] <Evaluation Criteria>

[0114] O: No emulsion is formed, transparent

[0115] Δ: A small amount of emulsion is formed, but there is no problem in commercial use.

[0116] X: A large amount of emulsion is formed to be opaque

[0117] 3. Haze Measurement

[0118] The coating compositions of Examples 1 to 18 and Comparative Examples 3 to 8 were each applied on a PET (polyethylene terephthalate) base material having a thickness of about 38 μm and a size of 5 cm×5 cm (width×length) with a wire-wound rod (Meyer bar) #8 for coating, cured at a temperature of about 130° C. for about 1 minute, and subsequently aged at a temperature of about 50° C. for about 24 hours to produce a release film specimen in which a release layer having a thickness of about 0.1 μm was formed on the base material.

[0119] After storing the specimen at a temperature of 85° C. and 85% relative humidity for 100 hours, it was left to stand at a temperature of 25° C. and 50% relative humidity for 1 hour, and then the haze of the specimen was measured by ASTM D1003 standard using a spectrophotometer (NDH700SP, Nippon Denshoku).

[0120] 4. Transmittance Measurement

[0121] The coating compositions of Examples 1 to 2 and 19 to 21, and Comparative Example 9 were each applied on a PET (polyethylene terephthalate) base material having a thickness of about 38 μm and a size of 5 cm×5 cm (width×length) with a wire-wound rod (Meyer bar) #8 for coating, cured at a temperature of about 130° C. for about 1 minute, and subsequently aged at a temperature of about 50° C. for about 24 hours to produce a release film specimen in which a release layer having a thickness of about 0.1 μm was formed on the base material.

[0122] The transmittance of the specimens for the transmitted light wavelength was measured using a colorimeter (SA5500, Nippon Denshoku), and the results were shown in FIG. 1. Here, when the incident amount of the total light is set to 100, the transmittance is expressed in a % ratio of the transmitted amount of the light therefrom.

[0123] 5. Release Peel Force Measurement

[0124] The coating compositions of Examples 1 to 18 and Comparative Examples 3 to 8 were each applied on a PET (polyethylene terephthalate) base material having a thickness of about 38 μm and a size of 5 cm×5 cm (width×length) with a wire-wound rod (Meyer bar) #8 for coating, cured at a temperature of about 130° C. for about 1 minute, and subsequently aged at a temperature of about 50° C. for about 24 hours to produce a release film specimen in which a release layer having a thickness of about 0.1 μm was formed on the base material.

[0125] The release layer of the specimen was attached to a standard adhesive tape (Tesa 7475, Tesa AG) to be in contact with each other and stored at a temperature of about 25° C. for 24 hours, and then the release peel force of the release layer on the standard pressure-sensitive adhesive tape was measured, while peeling the release film specimen with a peel angle of 180 degrees and a peel rate of 300 cm/min under conditions of a temperature of 25° C. and 50% relative humidity. Cheminstruments' AR-1000 was used as a measuring instrument, and Final Test Method No. 10 was applied as a measurement standard.

[0126] 6. Surface Energy Measurement

[0127] The coating compositions of Examples 1 to 18 and Comparative Examples 3 to 8 were each applied on a PET (polyethylene terephthalate) base material having a thickness of about 38 μm and a size of 5 cm×5 cm (width×length) with a wire-wound rod (Meyer bar) #8 for coating, cured at a temperature of about 130° C. for about 1 minute, and subsequently aged at a temperature of about 50° C. for about 24 hours to produce a release film specimen in which a release layer having a thickness of about 0.1 μm was formed on the base material.

[0128] The process of dropping the deionized water whose surface tension is known on the release layer of the specimen, and obtaining the contact angle thereof is repeated five times to obtain an average value of the obtained five contact angle values, and identically, the process of dropping the diiodomethane whose surface tension is known thereon and obtaining the contact angle thereof is repeated five times to obtain an average value of the obtained five contact angle values. Then, the surface energy was obtained by substituting the value (Strom value) regarding the solvent surface tension by the Owens-Wendt-Rabel-Kaelble method using the obtained average values of the contact angles for the deionized water and diiodomethane. Dataphysics' OCA 20 instrument was used as an instrument to measure the contact angle.

Preparation Example 1—Synthesis of Ultraviolet Absorber (A)

[0129] An ultraviolet absorber (A) as a compound of Formula C-1 below was prepared according to the following order.

[0130] 1) A compound of Formula A-1 below and a compound of Formula B-1 below (pKa value for dimethyl sulfoxide: 13.1) are placed in a reactor containing ethanol in a molar ratio of 1:1 and stirred.

[0131] 2) DBU (1,8-diazabicyclo(5.4.0)undec-7-ene) is slowly introduced into the reactor in an equivalent of 0.1 times the input of the compound of Formula A-1.

[0132] 3) It is stirred at a temperature of about 25° C. for 12 hours.

[0133] 4) Hydrochloric acid (HCl) is added in the same mole number as that of ethanol added in Step 2).

[0134] 5) After completion of the reaction, the resultant of Step 4) is filtered to yield a final product in a solid state.

##STR00005##

[0135] The NMR analysis results of the compound of Formula C-1 were shown in FIG. 1.

Preparation Example 2—Synthesis of Ultraviolet Absorber (C)

[0136] An ultraviolet absorber (C) as a compound of Formula C-2 below was prepared in the same method as in Preparation Example 1, except that a compound of Formula A-2 below and the compound of Formula B-1 (pKa value for dimethyl sulfoxide: 13.1) were placed in a reactor containing ethanol in a molar ratio of 1:1 and stirred.

##STR00006##

Example 1—Preparation of Coating Composition

[0137] About 100 parts by weight of an addition-curable silicone resin (KS847H, Shinetsu) as a release agent, about 1000 parts by weight of toluene as a solvent and about 2.5 parts by weight of a platinum-based catalyst (PL-50T, Shinetsu) were mixed and then about 30 parts by weight of the ultraviolet absorber (A) was added thereto to prepare a coating composition.

Examples 2 to 21 and Comparative Examples 1 to 9—Preparation of Coating Composition

[0138] Coating compositions were prepared in the same method as in Example 1 except for employing the compositions according to Tables 1 to 5 below.

TABLE-US-00001 TABLE 1 Example 1 2 3 4 5 6 Release Kind KS847H KS847H KS847H KS847H KS847H KS847H Agent Content 100 100 100 100 100 100 Solvent Kind 1 1 2 2 3 3 Content 1000 1000 1000 1000 1000 1000 Ultraviolet Kind A B A B A B Absorber Content 30 30 30 30 30 30 Catalyst Kind PL-50T PL-50T PL-50T PL-50T PL-50T PL-50T Content 2.5 2.5 2.5 2.5 2.5 2.5

TABLE-US-00002 TABLE 2 Example 7 8 9 10 11 12 Release Kind KS847H KS847H KS847H KS847H KS847H KS847H Agent Content 100 100 100 100 100 100 Solvent Kind MIX1 MIX1 MIX2 MIX2 MIX3 MIX3 Content 1000 1000 1000 1000 1000 1000 Ultraviolet Kind A B A B A B Absorber Content 30 30 30 30 30 30 Catalyst Kind PL-50T PL-50T PL-50T PL-50T PL-50T PL-50T Content 2.5 2.5 2.5 2.5 2.5 2.5

TABLE-US-00003 TABLE 3 Example 13 14 15 16 17 18 Release Kind KS847H KS847H KS847H KS847H KS847H KS847H Agent Content 100 100 100 100 100 100 Solvent Kind MIX4 MIX4 MIX5 MIX5 MIX6 MIX6 Content 1000 1000 1000 1000 1000 1000 Ultraviolet Kind A B A B A B Absorber Content 30 30 30 30 30 30 Catalyst Kind PL-50T PL-50T PL-50T PL-50T PL-50T PL-50T Content 2.5 2.5 2.5 2.5 2.5 2.5

TABLE-US-00004 TABLE 4 Example Comparative Example 19 20 21 1 2 3 Release Kind KS847H KS847H KS847H KS847H KS847H KS847H Agent Content 100 100 100 100 100 100 Solvent Kind 1 1 1 1 1 4 Content 1000 1000 1000 1000 1000 1000 Ultraviolet Kind A A A C D A Absorber Content 0.5 2 10 30 30 30 Catalyst Kind PL-50T PL-50T PL-50T PL-50T PL-50T PL-50T Content 2.5 2.5 2.5 2.5 2.5 2.5

TABLE-US-00005 TABLE 5 Comparative Example 4 5 6 7 8 9 Release Kind KS847H KS847H KS847H KS847H KS847H KS847H Agent Content 100 100 100 100 100 100 Solvent Kind 5 6 4 5 6 1 Content 1000 1000 1000 1000 1000 1000 Ultraviolet Kind A A B B B — Absorber Content 30 30 30 30 30 0 Catalyst Kind PL-50T PL-50T PL-50T PL-50T PL-50T PL-50T Content 2.5 2.5 2.5 2.5 2.5 2.5

[0139] In Tables 1 to 5 above, the unit of the respective component contents was parts by weight, and the meanings of the abbreviations described in Tables 1 to 5 above were summarized in Table 6 below.

TABLE-US-00006 TABLE 6 Applied Abbreviation Meaning KS847H: Addition-curable silicone resin, Shinetsu Solvent 1 Toluene (boiling point: 110.6° C.) Solvent 2 n-heptane (boiling point: 98.42° C.) Solvent 3 Methyl ethyl ketone (boiling point: 79.64° C.) Solvent 4 Methyl isobutyl ketone (boiling point: 116.5° C.) Solvent 5 Ethyl acetate (boiling point: 77.1° C.) Solvent 6 Ethanol (boiling point: 78.37° C.) Solvent MIX1 Mixed solvent of toluene: n-heptane = 50:50 (weight ratio) Solvent MIX2 Mixed solvent of toluene: methyl ethyl ketone = 50:50 (weight ratio) Solvent MIX3 Mixed solvent of toluene: n-heptane: methyl ethyl ketone = 50:40:10 (weight ratio) Solvent MIX4 Mixed solvent of toluene: n-heptane: methyl ethyl ketone = 50:10:40 (weight ratio) Solvent MIX5 Mixed solvent of toluene: n-heptane: methyl ethyl ketone = 50:30:20 (weight ratio) Solvent MIX6 Mixed solvent of toluene: n-heptane: methyl ethyl ketone = 50:20:30 (weight ratio) Ultraviolet Absorber A: Ultraviolet absorber of Preparation Example 1 Structural formula of ultraviolet absorber A   [00007] Ultraviolet Absorber B: Eutec's UV-1995 Structural formula of ultraviolet absorber B   [00008] Ultraviolet Absorber C: Ultraviolet absorber of Preparation Example 2 Structural formula of ultraviolet absorber C   [00009] Ultraviolet Absorber D CarboProtect (Registered Trademark Tinuvin, CAS. 945857- 19-2, BASF) Structural formula of ultraviolet absorber D   [00010]

[0140] The primary compatibility evaluation results for the coating compositions of Examples 1 to 2 and Comparative Examples 1 to 2 were described in Table 7 below.

TABLE-US-00007 TABLE 7 Target Evaluation Result Example 1 Δ 2 Δ Comparative 1 X Example 2 X

[0141] Through Table 7, it can be seen that when the ultraviolet absorber A or the ultraviolet absorber B, which is a compound included in the category of the structure defined in Formula 1 of the present application, is applied, sufficient compatibility with the release agent in the coating composition is ensured. Through this, it can be seen that it is appropriate to mix at least a compound within the category of the structure defined in Formula 1 with a release agent applied to the coating composition.

[0142] The secondary compatibility evaluation results of the coating compositions prepared in Examples 1 to 18 and Comparative Examples 2 to 8, the haze measurement results of the release layer specimens, and the measurement results of the release peel force and the surface energy were shown in Table 8 below.

TABLE-US-00008 TABLE 8 Secondary Compatibility Haze Release Peel Force Surface Energy Target Evaluation Result (%) (gf/in) (mN/m) Example 1 Δ 7.31 19.9 25.5 2 Δ 8.82 21.3 24.3 3 ◯~Δ 5.36 15.5 23.1 4 ◯~Δ 6.88 15.1 22.4 5 Δ 6.22 31.1 27.7 6 Δ 7.71 27.7 28.9 7 ◯~Δ 5.93 21 26.6 8 ◯~Δ 6.71 23.3 26.7 9 ◯~Δ 4.78 19.8 24 10 ◯~Δ 6.33 18.3 23.3 11 ◯ 3.74 15.7 21.4 12 ◯ 4.88 16.1 23.1 13 ◯ 4.22 17.7 22.8 14 ◯ 5.23 16.1 21.9 15 ◯ 4.05 18.8 24.4 16 ◯ 5.23 19.1 22.1 17 ◯ 4.33 16.4 23.1 18 ◯ 4.99 17 23 Comparative 3 Δ~X 8.88 43.2 31.1 Example 4 Δ~X 10.01 48.8 34.4 5 X 15.55 88.1 29.9 6 X 15.87 93.3 31.1 7 X 13.43 65.1 34.4 8 X 14.44 78.1 36.7

[0143] Through Table 8, it can be confirmed that in order to ensure compatibility of the release agent and the ultraviolet absorber in the coating composition, to ensure appropriate optical characteristics (haze), as the cured product (release layer) blocks the ultraviolet rays having the wavelengths to be blocked in the present application, and to have appropriate release peel force and surface energy, it is appropriate to apply a solvent having a boiling point within the range defined in the present application.