SURFACE-TREATING AGENT AND ARTICLE COMPRISING LAYER FORMED FROM SURFACE-TREATING AGENT

Abstract

An article including a base material and a layer formed from a compound represented by the following formula (1) or from a surface-treating agent comprising the compound:

##STR00001##

wherein each of symbols is as defined in the description.

Claims

1-20. (canceled)

21. An article comprising a base material and a layer formed from a compound represented by the following formula (1) or from a surface-treating agent comprising the compound: ##STR00043## wherein X.sup.1 to X.sup.5 each independently represent a hydrogen atom, a halogen atom, a hydrocarbon group, a nitro group, a hydroxy group, or an Rf group, provided that at least one of X.sup.1 to X.sup.5 is the Rf group; the Rf group represents R.sup.15R.sup.16; R.sup.15 represents a fluorine-containing hydrocarbon group optionally having an ether bond; R.sup.16 represents a single bond or a divalent organic group; R.sup.1 each independently in each occurrence represents a hydroxy group, a hydrolyzable group, or a halogen atom; R.sup.2 each independently in each occurrence represents a hydrogen atom, an alkyl group, or an aryl group; and n is an integer of 1 to 3.

22. The article according to claim 21, wherein X.sup.1 is the Rf group.

23. The article according to claim 21, wherein X.sup.1 is the Rf group, and X.sup.2 to X.sup.5 are each a hydrogen atom.

24. The article according to claim 21, wherein R.sup.15 is a perfluorohydrocarbon group optionally having an ether bond.

25. The article according to claim 21, wherein R.sup.15 is FC.sub.pF.sub.2p, wherein p is an integer of 1 to 100, and R.sup.16 is a single bond.

26. The article according to claim 21, wherein R.sup.15 is a group represented by the following formula:
R.sup.3PFPE- wherein R.sup.3 independently in each occurrence represents an alkyl group having 1 to 16 carbon atoms optionally substituted with one or more fluorine atoms; and PFPE is a group represented by (OC.sub.6F.sub.12).sub.a(OC.sub.5F.sub.10).sub.b(OC.sub.4F.sub.8).sub.c(OC.sub.3F.sub.6).sub.d(OC.sub.2F.sub.4).sub.e(OCF.sub.2).sub.f, wherein a, b, c, d, e, and f are each independently an integer of 0 or more and 200 or less, provided that the summation of a, b, c, d, e, and f is at least 1, and the order of the repeating units with parentheses accompanied by a subscript of a, b, c, d, e, or f is arbitrary in the formula, and R.sup.16 is a single bond or an alkyl group having 1-4 carbon atoms.

27. The article according to claim 21, further comprising a binder layer between the base material and the layer formed from the compound represented by the formula (1) or from the surface-treating agent comprising the compound, wherein the binder layer is formed from a silicon-containing compound.

28. The article according to claim 27, wherein the silicon-containing compound is one or more compounds selected from the group consisting of a SiH compound, a SiN compound, a SiO compound, halogenosilane, a Si(C).sub.4 compound, a SiSi compound, vinylsilane, allylsilane, and ethynylsilane.

29. The article according to claim 27, wherein the silicon-containing compound is at least one compound represented by formula (3) or formula (4):
SiR.sup.5.sub.4 (3) wherein R.sup.5 each independently represents a halogen atom or a hydrolyzable group,
Si.sub.yO.sub.zR.sup.6.sub.4y2z (4) wherein R.sup.6 each independently represents a halogen atom or a hydrolyzable group; y is 2 or more; z is 1 or more; and 4y2z is more than 0.

30. The article according to claim 21, wherein the surface-treating agent further comprises a silicon-containing compound.

31. The article according to claim 21, wherein the base material is glass, sapphire glass, resin, metal, ceramic, semiconductor, fiber, fur, leather, or wood.

32. The article according to claim 21, which is an optical member or a building member.

33. A surface-treating agent comprising: (A) a compound represented by the following formula (1): ##STR00044## wherein X.sup.1 to X.sup.5 each independently represent a hydrogen atom, a halogen atom, a hydrocarbon group, a nitro group, a hydroxy group, or an Rf group, provided that at least one of X.sup.1 to X.sup.5 is the Rf group; the Rf group represents R.sup.15R.sup.16; R.sup.15 represents a fluorine-containing hydrocarbon group optionally having an ether bond; R.sup.16 represents a single bond or a divalent organic group; R.sup.1 each independently in each occurrence represents a hydroxy group, a hydrolyzable group, or a halogen atom; R.sup.2 each independently in each occurrence represents a hydrogen atom, an alkyl group, or an aryl group; and n is an integer of 1 to 3; and (B) one or more additional components selected from a silicon-containing compound, a fluorine-containing oil, a silicone oil, and a solvent.

34. The surface-treating agent according to claim 33, wherein the additional component includes a silicon-containing compound.

35. The surface-treating agent according to claim 33, wherein the silicon-containing compound is one or more compounds selected from the group consisting of a SiH compound, a SiN compound, a SiO compound, halogenosilane, a Si(C).sub.4 compound, a SiSi compound, vinylsilane, allylsilane, and ethynylsilane.

36. The surface-treating agent according to claim 33, wherein the silicon-containing compound is at least one compound represented by formula (3) or formula (4):
SiR.sup.5.sub.4 (3) wherein R.sup.5 each independently represents a halogen atom or a hydrolyzable group,
Si.sub.yO.sub.zR.sup.6.sub.4y2z (4) wherein R.sup.6 each independently represents a halogen atom or a hydrolyzable group; y is 2 or more; z is 1 or more; and 4y2z is more than 0.

37. The surface-treating agent according to claim 33, wherein the fluorine-containing oil is one or more compounds represented by the following formula (5):
R.sup.21(OC.sub.4F.sub.8).sub.a(OC.sub.3F.sub.6).sub.b(OC.sub.2F.sub.4).sub.c(OCF.sub.2).sub.dR.sup.22 (5) wherein R.sup.21 represents a C.sub.1-16 alkyl group optionally substituted with one or more fluorine atoms; R.sup.22 represents a C.sub.1-16 alkyl group optionally substituted with one or more fluorine atoms; a, b, c, and d are each independently an integer of 0 or more and 300 or less, provided that the summation of a, b, c, and d is at least 1, and the order of the repeating units with parentheses accompanied by a subscript of a, b, c, or d is arbitrary in the formula.

38. The surface-treating agent according to claim 33, wherein the silicone oil is a linear or cyclic silicone oil having 2,000 or less siloxane bonds.

39. The surface-treating agent according to claim 33, wherein the solvent is one or more solvents selected from a hydrocarbon solvent, a chlorinated hydrocarbon solvent, an ether-based solvent, an ester-based solvent, a propylene glycol-based solvent, a ketone-based solvent, an alcohol-based solvent, an aromatic hydrocarbon, a C.sub.5-12 perfluoroaliphatic hydrocarbon, a polyfluoroaromatic hydrocarbon, a polyfluoroaliphatic hydrocarbon, a hydrofluoroether, a hydrochlorofluorocarbon, and a cellosolve-based solvent.

40. The surface-treating agent according to claim 33, which is used as an antifouling coating agent or a water-proof coating agent.

Description

EXAMPLES

Example 1

[0170] (4-tridecafluorohexylphenyl)trimethoxysilane was dissolved in perfluorobutyl ethyl ether such that the concentration was 2 wt % to prepare a surface-treating agent 1. The surface-treating agent 1 prepared was then applied onto a chemically toughened glass sheet by spin coating. Thereafter, the chemically toughened glass sheet with the surface-treating agent was left to stand at a temperature of 65 C. and a humidity of 90% for 14 hours to form a surface-treating layer of Example 1.

Comparative Example 1

[0171] A surface-treating agent 2 was prepared in the same manner as in Example 1 except that (3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)trimethoxysilane was used instead of (4-tridecafluorohexylphenyl)trimethoxysilane. Subsequently, a surface-treating layer of Example 2 was formed in the same manner as in Example 1 except that the surface-treating agent 2 prepared was used.

[0172] Evaluation of Weatherability

[0173] A static water contact angle after light irradiation was measured for the surface-treating layers formed on the surface of the base material in Example 1 and Comparative Example 1. The light irradiation was by a SUPER XENON TESTER (XER-W75 from IWASAKI ELECTRIC CO., LTD., irradiance: 2.23 W/m.sup.2 at 420 nm), and the measurement of the static water contact angles was by a contact angle meter (from Kyowa Interface Science Co., Ltd.) with 2 L of water. First, as initial evaluation, a static water contact angle of a surface-treating layer of which the surface had not still contacted with anything after formation thereof was measured (exposure time is zero hour). Thereafter, the static water contact angle (degree) was measured for each defined time until a cumulative exposure time of 400 hours. The results are shown in Table 1.

TABLE-US-00001 TABLE 1 Contact angle (degree) Exposure time Comparative (hour) Example 1 Example 1 0 110 106 100 110 105 200 110 103 300 110 101 400 109 100

[0174] As can be understood from the results, the silane compound having a phenyl group according to the present invention was confirmed that the weatherability was improved as compared with Comparative Example 1 which did not have such structure.

Example 2

[0175] A polysilazane compound (NL120A, Merck KGaA) was dissolved in dibutyl ether such that the concentration was 3 wt % to prepare a binder-treatment agent 1. The binder-treatment agent 1 prepared was then applied onto a chemically toughened glass sheet by spin coating. Thereafter, the chemically toughened glass sheet was left to stand at room temperature for 30 minutes to form a binder layer, and then the surface-treating agent 1 prepared in Example 1 was applied thereto by spin coating under the same conditions. Thereafter, the chemically toughened glass sheet with the surface-treating agent was left to stand at a temperature of 65 C. and a humidity of 90% for 14 hours to form a surface-treating layer of Example 2.

Comparative Example 2

[0176] A surface-treating layer of Comparative Example 2 was formed in the same manner as in Example 2 except that the surface-treating agent 2 was used instead of the surface-treating agent 1.

[0177] Evaluation of Acid Resistance

[0178] First, as initial evaluation, a static water contact angle of a surface-treating layer of which the surface had not still contacted with anything after formation thereof was measured. Thereafter, each of the treated glass sheets in Example 2 and Comparative Example 2 was dipped in 0.1 mol % nitric acid aqueous solution, and the static water contact angle (degree) was measured for each defined time until a cumulative dipping time of 7 days. The results are shown in Table 2.

TABLE-US-00002 TABLE 2 Contact angle (degree) Exposure time Comparative (day) Example 2 Example 2 0 108 106 3 108 100 7 105 98

[0179] Evaluation of Alkali Resistance

[0180] First, as initial evaluation, a static water contact angle of a surface-treating layer of which the surface had not still contacted with anything after formation thereof was measured. Thereafter, each of the treated glass sheets in Examples 1 and 2 and Comparative Examples 1 and 2 was dipped in 1 mol % NaOH aqueous solution, and the static water contact angle (degree) was measured for each defined time. The evaluation was terminated when the measured value of a contact angle was smaller than 50 degrees, and otherwise continued until a cumulative dipping time of 24 hours at the longest. The results are shown in Table 3 (wherein the symbol - represents no measurement).

TABLE-US-00003 TABLE 3 Contact angle (degree) Exposure time Example Example Comparative Comparative (hour) 1 2 Example 1 Example 2 0 106 108 107 104 1 100 101 44 77 4 97 100 41 24 50 92

[0181] As can be understood from the results, the silane compound having a phenyl group according to the present invention was confirmed that the chemical resistance was improved as compared with Comparative Examples 1 and 2 which did not have such structure. In addition, it was confirmed that a higher effect was obtained in combination with a binder layer.

Industrial Applicability

[0182] The surface-treating agent according to the present invention can be suitably used to form a surface-treating layer on the surface of a wide variety of base materials, in particular, base materials requiring weatherability. The article according to the present invention can be suitably used under environments in which weatherability is required.