Surface treated optical components

Abstract

An optical component that is surface-treated with a surface treatment agent, preferably a surface treatment agent comprising an organosilane or organosiloxane compound having a lipophilic group and a functional group having adhesion to a substrate, and in which the oleic acid contact angle of the surface treatment agent layer is 20° or less has excellent lipophilicity and does not lose transparency even when oil stains adhere.

Description

Technical Field

[0001] The present invention relates to an optical member whose surface is treated with a surface treating agent containing an organosilane or organosiloxane compound having a functional group having adhesion to a substrate and a lipophilic group in its molecule. Background Art

[0002] Generally, optical components such as camera lenses and other photographic devices have water droplets and oil stains attached to their surfaces due to weather and surrounding environment, which can cause them to lose transparency and sometimes make the captured images unclear. Therefore, in order to improve the appearance and transparency, the demand for technologies that make it difficult for dirt to adhere to optical components and technologies that make dirt less noticeable is increasing year by year, and it is desired to develop materials that can meet these requirements.

[0003] Generally, as a surface modifier for substrates such as glass and resin, it is well known that silane coupling agents have been widely used as coating agents for the surfaces of various substrates. Silane coupling agents have an organic functional group and a reactive silyl group (generally a hydrolyzable silyl group such as an alkoxysilyl group) in one molecule, and the hydrolyzable silyl group undergoes a self-condensation reaction using moisture in the air to form a film. The film is chemically / physically bonded to the surface of glass, metal, etc. through the hydrolyzable silyl group, thereby forming a durable and firm film.

[0004] Therefore, a large number of compositions have been disclosed that can form a coating having antifouling properties on the surface of a substrate by using a fluoropolyether group-containing polymer in which a hydrolyzable silyl group is introduced into a fluoropolyether group-containing compound (Patent Documents 1 to 6: JP-A-2008-534696, JP-A-2008-537557, JP-A-2012-072272, JP-A-2012-157856, JP-A-2013-136833, JP-A-2015-199906).

[0005] However, although the coating layer made of the existing fluoropolyether group-containing polymer has excellent antifouling property due to its high water and oil repellency, the attached liquid is repelled by the surface to form fine droplets, which causes blurring due to light scattering and reduces transparency.

[0006] Prior art literature

[0007] Patent Literature

[0008] Patent Document 1: Japanese Patent Application No. 2008-534696

[0009] Patent Document 2: Japanese Patent Application No. 2008-537557

[0010] Patent Document 3: Japanese Patent Application Publication No. 2012-072272

[0011] Patent Document 4: Japanese Patent Application Publication No. 2012-157856

[0012] Patent Document 5: Japanese Patent Application Publication No. 2013-136833

[0013] Patent Document 6: Japanese Patent Application Publication No. 2015-199906 Summary of the invention

[0014] Problems to be solved by the invention

[0015] In view of the above-mentioned circumstances, an object of the present invention is to provide an optical member surface-treated with a surface treating agent containing an organosilane compound or an organosiloxane compound capable of forming a cured film exhibiting lipophilicity.

[0016] Means for solving problems

[0017] The present inventors have conducted intensive studies to achieve the above-mentioned object and have found that an optical component which is surface-treated with a surface treatment agent, preferably a surface treatment agent comprising an organosilane or organosiloxane compound having a lipophilic group and a functional group having adhesion to a substrate, and in which the oleic acid contact angle of the surface treatment agent layer is 20° or less, has excellent lipophilicity and maintains transparency even when oil stains adhere, thereby completing the present invention.

[0018] Therefore, the present invention provides the following optical member.

[0019] [1] An optical member having a surface treated with a surface treatment agent, wherein the surface treatment agent layer has an oleic acid contact angle of 20° or less.

[0020] [2] The optical member described in [1], wherein the surface treatment agent layer has a film thickness of 2 nm to 100 nm.

[0021] [3] The optical member according to [1] or [2], wherein the haze after being immersed in oleic acid for one minute and then pulled up is 1.5% or less.

[0022] [4] The optical member according to any one of [1] to [3], wherein the surface treatment agent comprises an organosilane or organosiloxane compound having a lipophilic group and a functional group having adhesion to a substrate.

[0023] [5] The optical member described in [4], wherein the surface treatment agent comprises one or more selected from an organic silane compound, an organic siloxane compound, and a partial (hydrolyzed) condensate thereof containing a lipophilic group and a hydroxyl group or a hydrolyzable group.

[0024] [6] The optical member described in [5], wherein the surface treatment agent contains an organosilane compound represented by the following general formula (1) and / or a partial (hydrolyzed) condensate thereof.

[0025] [Chemistry 1]

[0026]

[0027] (where A is -C(=O)OR 1 、-C(=O)NR 1 2. -C(=O)SR 1 and -P(=O)(OR 1 )2, R 1 is a hydrogen atom, an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, or an aralkyl group having 7 to 30 carbon atoms, Y is independently a divalent organic group, R is independently an alkyl group having 1 to 4 carbon atoms or a phenyl group, X is independently a hydroxyl group or a hydrolyzable group, and n is an integer of 1 to 3.

[0028] [7] The optical component described in [6], wherein in the general formula (1), Y is an alkylene group having 2 to 30 carbon atoms, which may include a divalent group selected from -O-, -S-, -NR-, -C(=O)-, -C(=O)O-, -C(=O)NR-, -OC(=O)NR- (R is an alkyl group having 1 to 4 carbon atoms or a phenyl group), a silylene group, a silylene group, and a linear, branched or cyclic divalent organic (poly)siloxane residue having 2 to 10 silicon atoms, and may also include an arylene group having 6 to 20 carbon atoms.

[0029] [8] The optical member according to [6] or [7], wherein the surface treatment agent comprises an organosilane compound represented by the following general formula (2) and / or a partial (hydrolyzed) condensate thereof.

[0030] [Chemistry 2]

[0031]

[0032] (Where R 2 is an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an aralkyl group having 7 to 20 carbon atoms, m is each independently an integer of 2 to 20, and X is independently a hydroxyl group or a hydrolyzable group.

[0033] [9] The optical component described in any one of [6] to [8], wherein in the general formula (1) or (2), X is independently a group selected from a hydroxyl group, an alkoxy group having 1 to 10 carbon atoms, an alkoxy-substituted alkoxy group having 2 to 10 carbon atoms, an acyloxy group having 1 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, a halogen atom, an oxime group, an isocyanate group, and a cyanate group.

[0034]

[10] The optical member described in [5], wherein the surface treatment agent contains an organosiloxane compound represented by the following general formula (3) and / or a partial (hydrolyzed) condensate thereof.

[0035] [Chemistry 3]

[0036]

[0037] (wherein A' is -CH3, -C(=O)OR 1 、-C(=O)NR 1 2. -C(=O)SR 1 and -P(=O)(OR 1 )2, R 1 is a hydrogen atom, an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, or an aralkyl group having 7 to 30 carbon atoms, Y' is independently a divalent organic group, W is independently an alkyl group having 1 to 4 carbon atoms, a phenyl group, a hydroxyl group, or a hydrolyzable group, R is independently an alkyl group having 1 to 4 carbon atoms or a phenyl group, X is independently a hydroxyl group or a hydrolyzable group, n is an integer of 1 to 3, and q is an integer of 1 to 3.)

[0038]

[11] The optical component described in

[10] , wherein in the general formula (3), Y' is an alkylene group having 2 to 30 carbon atoms, which may include a divalent group selected from -O-, -S-, -NR-, -C(=O)-, -C(=O)O-, -C(=O)NR-, -OC(=O)NR- (R is an alkyl group having 1 to 4 carbon atoms or a phenyl group), a silylene group, a silylene group, and a linear, branched or cyclic divalent organic (poly)siloxane residue having 2 to 10 silicon atoms, and may also include an arylene group having 6 to 20 carbon atoms.

[0039]

[12] The optical component described in

[10] or

[11] , wherein in the general formula (3), W is independently a group selected from an alkyl group having 1 to 4 carbon atoms, a phenyl group, a hydroxyl group, an alkoxy group having 1 to 10 carbon atoms, an alkoxy-substituted alkoxy group having 2 to 10 carbon atoms, an acyloxy group having 1 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, a halogen atom, an oxime group, an isocyanate group and a cyanate group.

[0040]

[13] The optical member according to any one of

[10] to

[12] , wherein the surface treatment agent comprises an organosiloxane compound represented by the following general formula (4) and / or a partial (hydrolyzed) condensate thereof.

[0041] [Chemistry 4]

[0042]

[0043] (Where R 3 is an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an aralkyl group having 7 to 20 carbon atoms, Q is a single bond, or a divalent group selected from a silylene group, a silylene group, and a linear, branched, or cyclic divalent organic (poly)siloxane residue having 2 to 10 silicon atoms, m' is independently an integer of 1 to 20, m" is an integer of 2 to 20, and X is independently a hydroxyl group or a hydrolyzable group.)

[0044]

[14] An optical component according to any one of

[10] to

[13] , wherein in the general formula (3) or (4), X is independently a group selected from a hydroxyl group, an alkoxy group having 1 to 10 carbon atoms, an alkoxy-substituted alkoxy group having 2 to 10 carbon atoms, an acyloxy group having 1 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, a halogen atom, an oxime group, an isocyanate group, and a cyanate group.

[0045]

[15] The optical component according to any one of [1] to

[14] , wherein the optical component is a spectacle lens.

[0046]

[16] The optical component according to any one of [1] to

[14] , wherein the optical component is a camera lens or a lens cover.

[0047] Furthermore, the present invention provides the following optical component.

[0048] [1'] An optical component, wherein the optical component has a surface treatment agent layer having a film thickness of 2 nm or more and less than 5 nm, which is a room temperature curing film or a heat curing film formed by surface treatment with a surface treatment agent, and the oleic acid contact angle of the surface treatment agent layer is 20° or less,

[0049] The surface treatment agent comprises an organosilane or organosiloxane compound containing a lipophilic group and a hydrolyzable group, but does not include a surface treatment agent containing a coating composition comprising:

[0050] The hydrolyzable group is a group selected from an alkoxy group having 1 to 10 carbon atoms, an alkoxy-substituted alkoxy group having 2 to 10 carbon atoms, an acyloxy group having 1 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, a halogen atom, an oxime group, and a cyanate group.

[0051] The coating composition contains (A) one or more organic silane or siloxane compounds represented by the following general formula (1') and their partial (hydrolyzed) condensates and (B) one or more silane or siloxane compounds represented by the following general formula (2') and their partial (hydrolyzed) condensates in a mass ratio of 50:50 to 90:10, wherein the total of the components (A) and (B) is 100.

[0052]

[0053] In the formula, A is -C(=O)OR 1 、-C(=O)NR 1 2. -C(=O)SR 1 and -P(=O)(OR 1 )2, R 1 is a hydrogen atom, an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, or an aralkyl group having 7 to 30 carbon atoms, Y is independently a divalent organic group which may have an organopolysiloxane residue, R is independently an alkyl group having 1 to 4 carbon atoms or a phenyl group, X is independently a hydroxyl group or a hydrolyzable group, and n is an integer of 1 to 3,

[0054]

[0055] In the formula, Rf is a perfluoroalkylene group or a divalent perfluoropolyether group, and Y, R, X, and n are the same as described above.

[0056] [2']. The optical component according to [1'], wherein the camera lens or lens cover is immersed in oleic acid for 1 minute and then pulled up, and the haze is 1.5% or less.

[0057] [3'] The optical component according to [1'], wherein the organosilane compound is an organosilane compound represented by the following general formula (1),

[0058]

[0059] In the formula, A is -C(=O)OR 1 、-C(=O)NR 1 2. -C(=O)SR 1 and -P(=O)(OR 1 )2, R 1is a hydrogen atom, an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, or an aralkyl group having 7 to 30 carbon atoms, Y is independently a divalent organic group, R is independently an alkyl group having 1 to 4 carbon atoms or a phenyl group, X is independently a group selected from an alkoxy group having 1 to 10 carbon atoms, an alkoxy-substituted alkoxy group having 2 to 10 carbon atoms, an acyloxy group having 1 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, a halogen atom, an oxime group, and a cyanate group, and n is an integer of 1 to 3.

[0060] [4'] The optical component according to [3'], wherein in the general formula (1), Y is an alkylene group having 2 to 30 carbon atoms, which may include a divalent group selected from -O-, -S-, -NR-, -C(=O)-, -C(=O)O-, -C(=O)NR-, -OC(=O)NR-, a silylene group, a silylene group, and a linear, branched or cyclic divalent organic (poly)siloxane residue having 2 to 10 silicon atoms, and may also include an arylene group having 6 to 20 carbon atoms;

[0061] Here, R is an alkyl group having 1 to 4 carbon atoms or a phenyl group.

[0062] [5'] The optical component according to [3'], wherein the organosilane compound is an organosilane compound represented by the following general formula (2),

[0063]

[0064] In the formula, R 2 is an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an aralkyl group having 7 to 20 carbon atoms, m is each independently an integer of 2 to 20, and X is independently a group selected from an alkoxy group having 1 to 10 carbon atoms, an alkoxy-substituted alkoxy group having 2 to 10 carbon atoms, an acyloxy group having 1 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, a halogen atom, an oxime group, and a cyanate group.

[0065] [6'] The optical component according to [1'], wherein the organosiloxane compound is an organosiloxane compound represented by the following general formula (3),

[0066]

[0067] In the formula, A' is -CH3, -C(=O)OR 1 、-C(=O)NR 1 2. -C(=O)SR 1 and -P(=O)(OR 1 )2, R 1is a hydrogen atom, an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, or an aralkyl group having 7 to 30 carbon atoms, Y' is independently a divalent organic group, W is independently an alkyl group having 1 to 4 carbon atoms, a phenyl group, a hydroxyl group, or a hydrolyzable group, R is independently an alkyl group having 1 to 4 carbon atoms or a phenyl group, X is independently a group selected from an alkoxy group having 1 to 10 carbon atoms, an alkoxy-substituted alkoxy group having 2 to 10 carbon atoms, an acyloxy group having 1 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, a halogen atom, an oxime group, and a cyanate group, n is an integer of 1 to 3, and q is an integer of 1 to 3.

[0068] [7'] The optical component according to [6'], wherein in the general formula (3), Y' is an alkylene group having 2 to 30 carbon atoms, which may include a divalent group selected from -O-, -S-, -NR-, -C(=O)-, -C(=O)O-, -C(=O)NR-, -OC(=O)NR-, silylene groups, silylene groups, and divalent organic (poly)siloxane residues having 2 to 10 silicon atoms in a linear, branched or cyclic form, and may also include an arylene group having 6 to 20 carbon atoms;

[0069] Here, R is an alkyl group having 1 to 4 carbon atoms or a phenyl group.

[0070] [8'] The optical component according to [6'], wherein the organosiloxane compound is an organosiloxane compound represented by the following general formula (4),

[0071]

[0072] In the formula, R 3 is an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an aralkyl group having 7 to 20 carbon atoms, Q is a single bond, or a divalent group selected from a silylene group, a silylene group, and a linear, branched, or cyclic divalent organic (poly)siloxane residue having 2 to 10 silicon atoms, m' is each independently an integer of 1 to 20, m" is an integer of 2 to 20, and X is independently a group selected from an alkoxy group having 1 to 10 carbon atoms, an alkoxy-substituted alkoxy group having 2 to 10 carbon atoms, an acyloxy group having 1 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, a halogen atom, an oxime group, and a cyanate group.

[0073] Effects of the Invention

[0074] The optical component of the present invention is surface treated with a surface treatment agent, preferably an organosilane or organosiloxane compound containing a lipophilic group and a functional group having adhesion to a substrate in the molecule, and the oleic acid contact angle of the surface treatment agent layer is 20° or less, so that attached oil stains and the like can be wetted and spread on the surface. Therefore, the optical component surface treated with the surface treatment agent of the present invention does not lose transparency even when oil stains and the like are attached. DETAILED DESCRIPTION

[0075] The optical component of the present invention is surface-treated with a surface treatment agent, and the oleic acid contact angle of the surface treatment agent layer is less than 20°. If the oleic acid contact angle is less than 20°, the lipophilicity and transparency when oil stains are attached are good. The oleic acid contact angle is less than 20°, preferably less than 15°, and more preferably less than 10°. There is no particular limitation on the lower limit of the oleic acid contact angle, for example, it is 2°. It should be noted that in the present invention, the oleic acid contact angle can be measured for the surface treatment agent layer using a contact angle meter Drop Master (manufactured by Kyowa Interface Science Co., Ltd.). More specifically, oleic acid is used to drop 2 μL of a droplet on a horizontal surface treatment agent layer at room temperature of 20°C, and the contact angle 40 seconds after the drop is measured at 10 locations, and the average value of the measurement results is taken as the contact angle.

[0076] In order to make the optical component of the present invention satisfy the above-mentioned contact angle range, it is preferred to use an organic silane compound or an organic silicone compound having a lipophilic group such as an alkyl group, ester group, amide group, sulfonic acid group or phosphonic acid group and a functional group such as an alkoxysilyl group that has adhesion to the substrate in the molecule to treat the surface of the optical component.

[0077] The film thickness of the surface treatment agent layer of the optical component of the present invention is preferably 2 nm or more and 100 nm or less. The lower limit of the film thickness is more preferably 2.5 nm or more, and more preferably 3 nm or more. The upper limit of the film thickness is more preferably 90 nm or less, and more preferably 50 nm or less. If the film thickness is thinner than 2 nm, the lipophilicity is sometimes damaged, and if it becomes thicker than 100 nm, the transparency of the optical component is sometimes damaged.

[0078] The optical component of the present invention is immersed in oleic acid for 1 minute and then pulled up, and the haze is 1.5% or less. If the haze is 1.5% or less, the transparency when oil stains adhere becomes good. The haze is preferably 1% or less, and more preferably 0.5% or less. There is no particular limitation on the lower limit of the haze, and for example, it is 0.01%. It should be noted that in the present invention, the haze can be measured using a haze meter NDH5000 (manufactured by Nippon Denshoku Industries Co., Ltd.) for the surface treatment agent layer.

[0079] In order to make the optical component of the present invention fall within the above-mentioned haze range, it is preferred that the surface of the optical component is surface-treated with an organic silane compound or an organic silicone compound having a lipophilic group such as an alkyl group, an ester group, an amide group, a sulfonic acid group or a phosphonic acid group and a functional group such as an alkoxysilyl group having adhesion to the substrate in the molecule, so that the oleic acid contact angle of the surface treatment agent layer is 20° or less.

[0080] The optical component of the present invention is preferably surface treated with a surface treating agent comprising an organosilane or organosiloxane compound having a lipophilic group and a functional group having adhesion to a substrate. If such a surface treating agent is used, the lipophilicity of the surface treated optical component and the transparency when oil stains adhere become good.

[0081] As the above-mentioned adhesion functional group, hydroxyl, hydrolyzable silyl, epoxy, vinyl, acryloyl, methacryloyl, amino, mercapto, imidazole, phosphoric acid, isocyanate, urea, styryl can be listed. Hydroxyl and hydrolyzable silyl are preferred. If such adhesion functional group is used, the surface treatment agent can form a film that is firmly adhered to the substrate.

[0082] As the above-mentioned surface treatment agent, it is preferred to include an organic silane compound containing a lipophilic group and a hydroxyl group or a hydrolyzable group, an organic siloxane compound and their partial (hydrolysis) condensation products, and it is more preferred to have an organic silane compound and / or its partial (hydrolysis) condensation product represented by the following general formula (1), or an organic siloxane compound and / or its partial (hydrolysis) condensation product represented by the following general formula (3).

[0083] [Chemistry 5]

[0084]

[0085] (where A is -C(=O)OR 1 、-C(=O)NR 1 2. -C(=O)SR 1 and -P(=O)(OR 1 )2, R 1 is a hydrogen atom, an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, or an aralkyl group having 7 to 30 carbon atoms, Y is independently a divalent organic group, R is independently an alkyl group having 1 to 4 carbon atoms or a phenyl group, X is independently a hydroxyl group or a hydrolyzable group, and n is an integer of 1 to 3.

[0086] [Chemistry 6]

[0087]

[0088] (wherein A' is -CH3, -C(=O)OR1 、-C(=O)NR 1 2. -C(=O)SR 1 and -P(=O)(OR 1 )2, R 1 is a hydrogen atom, an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, or an aralkyl group having 7 to 30 carbon atoms, Y' is independently a divalent organic group, W is independently an alkyl group having 1 to 4 carbon atoms, a phenyl group, a hydroxyl group, or a hydrolyzable group, R is independently an alkyl group having 1 to 4 carbon atoms or a phenyl group, X is independently a hydroxyl group or a hydrolyzable group, n is an integer of 1 to 3, and q is an integer of 1 to 3.)

[0089] An organosilane compound represented by the following general formula (1):

[0090] [Chemistry 7]

[0091]

[0092] (where A is -C(=O)OR 1 、-C(=O)NR 1 2. -C(=O)SR 1 and -P(=O)(OR 1 )2, R 1 is a hydrogen atom, an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, or an aralkyl group having 7 to 30 carbon atoms, Y is independently a divalent organic group, R is independently an alkyl group having 1 to 4 carbon atoms or a phenyl group, X is independently a hydroxyl group or a hydrolyzable group, and n is an integer of 1 to 3.

[0093] The lipophilic group-containing (hydrolyzable) organosilane compound represented by the above formula (1) has a structure in which a lipophilic terminal group is bonded to a hydrolyzable silyl group such as an alkoxysilyl group or a hydroxyl-containing silyl group via a silylene linking group, and has excellent adhesion to substrates and lipophilicity.

[0094] In the above formula (1), A is -C(=O)OR 1 An ester or carboxylic acid represented by -C(=O)NR 1 Amide represented by 2, -C(=O)SR 1 The thioester or thioacid represented by -P(=O)(OR 1 Any of the phosphonic acid ester or phosphonic acid represented by )2 is the lipophilic terminal group in the present invention.

[0095] Among them, R 1It is a hydrogen atom, an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, or an aralkyl group having 7 to 30 carbon atoms. The alkyl group may be linear, branched, or cyclic, and these may be combined. It is preferably a linear alkyl group having 1 to 8 carbon atoms, and more preferably a linear alkyl group having 2 to 4 carbon atoms.

[0096] As R 1 Specific examples include hydrogen atoms, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, tetradecyl, hexadecyl, octadecyl, isopropyl, isobutyl, tert-butyl, neopentyl, tert-hexyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclohexylmethyl, norbornyl, decahydronaphthyl, adamantyl, adamantylmethyl and other alkyl groups, phenyl, tolyl, naphthyl and other aryl groups, benzyl, phenylethyl, phenylpropyl and other aralkyl groups. 1 , preferably ethyl or octyl.

[0097] Examples of A include the following groups.

[0098] [Chemistry 8]

[0099]

[0100] [Chemistry 9]

[0101]

[0102] (CH3O)2OP-

[0103] (C2H5O)2OP-

[0104] In the above formula (1), X is a hydroxyl group or a hydrolyzable group which may be different from each other. Examples of such X include hydroxyl groups, methoxy groups, ethoxy groups, propoxy groups, isopropoxy groups, butoxy groups and other alkoxy groups having 1 to 10 carbon atoms, alkoxy-substituted alkoxy groups having 2 to 10 carbon atoms, such as methoxymethoxy groups and methoxyethoxy groups, acyloxy groups having 1 to 10 carbon atoms, such as acetoxy groups, alkenyloxy groups having 2 to 10 carbon atoms, such as isopropenyloxy groups, halogen atoms such as fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms, oxime groups, isocyanate groups, and cyanate groups. Among them, methoxy groups, ethoxy groups, isopropenyloxy groups, and chlorine atoms are preferred.

[0105] In the above formula (1), R is an alkyl group having 1 to 4 carbon atoms, such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, or phenyl, and methyl is preferred. n is an integer of 1 to 3, preferably 2 or 3, and more preferably 3 from the viewpoint of reactivity and adhesion to the substrate.

[0106] In the above formula (1), Y is a divalent organic group, which is a linking group between the A group and the silylene group, and between a hydrolyzable silyl group or a hydroxyl group-containing silyl group and the silylene group, and is preferably a divalent group selected from -O-, -S-, -NR-, -C(=O)-, -C(=O)O-, -C(=O)NR-, -OC(=O)NR- (R is the same as above), a silylene group, a silylene group and a linear, branched or cyclic divalent organic (poly)siloxane residue having 2 to 10 silicon atoms, and an alkylene group having 2 to 30 carbon atoms, particularly 2 to 20 carbon atoms, which may contain an arylene group having 6 to 20 carbon atoms, and is more preferably a divalent group represented by the following formula (5).

[0107] -R 4 -Z-(R 4 ) a -(5)

[0108] In the above formula (5), R 4 The independently divalent hydrocarbon group specifically includes alkylene groups having 2 to 30 carbon atoms such as ethylene, propylene, butylene, and hexamethylene, and alkylene groups having 7 to 30 carbon atoms including arylene groups having 6 to 20 carbon atoms such as phenylene, and alkylene groups having 2 to 20 carbon atoms are preferred.

[0109] In the above formula (5), Z is a single bond, or a divalent group selected from -O-, -S-, -NR-, -C(=O)-, -C(=O)O-, -C(=O)NR-, -OC(=O)NR-, silylene, silylene and a linear, branched or cyclic divalent organic (poly)siloxane residue having 2 to 10 silicon atoms, preferably 2 to 5 silicon atoms, and R is the same as above.

[0110] Among them, the following groups can be exemplified as the silanylene group and the silanylene group.

[0111] [Chemistry 10]

[0112]

[0113] (Where R 5 is an alkyl group having 1 to 4 carbon atoms such as methyl, ethyl, propyl, butyl, or an aryl group having 6 to 10 carbon atoms such as phenyl, 5 Can be the same or different. 6 It is an alkylene group having 1 to 4 carbon atoms such as methylene, ethylene, propylene (trimethylene, methylethylene), or an arylene group having 6 to 10 carbon atoms such as phenylene.

[0114] Examples of the linear, branched or cyclic divalent organo(poly)siloxane residue having 2 to 10 silicon atoms, preferably 2 to 5 silicon atoms include the following groups.

[0115] [Chemistry 11]

[0116]

[0117] (Where R 5 Same as above. g is an integer of 1 to 9, preferably an integer of 1 to 4, and h is an integer of 1 to 8, preferably an integer of 1 to 3.)

[0118] In the above formula (5), a is 0 or 1.

[0119] Specific examples of Y include the following groups.

[0120] [Chemistry 12]

[0121] -CH2CH2-

[0122] -CH2CH2CH2-

[0123] -CH2CH2CH2CH2-

[0124] -CH2CH2CH2CH2CH2CH2-

[0125] -CH2CH2CH2CH2CH2CH2CH2-

[0126] -CH2CH2CH2CH2CH C H2CH2-

[0127] -CH2CH2CH2CH2CH2CH2CH2CH2CH2-

[0128] -CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2-

[0129] -CH2CH2CH2CH2CH2CH2CH2CH2CH2CH22-

[0130] -CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2-

[0131]

[0132] [Chemistry 13]

[0133] -CH2CH2-O-CH2CH2-

[0134] -(CH2) 10 -O-CH2CH2-

[0135]

[0136] -CH2CH2-S-CH2CH2-

[0137]

[0138] [Chemistry 14]

[0139]

[0140] Examples of the lipophilic group-containing (hydrolyzable) organosilane compound represented by the above formula (1) include compounds represented by the following formulas.

[0141] [Chemistry 15]

[0142]

[0143] [Chemistry 16]

[0144]

[0145] [Chemistry 17]

[0146]

[0147] [Chemistry 18]

[0148]

[0149] [Chemistry 19]

[0150]

[0151] As the lipophilic group-containing (hydrolyzable) organosilane compound represented by the above formula (1), a compound represented by the following general formula (2) is more preferable.

[0152] [Chemistry 20]

[0153]

[0154] (Where R 2 is an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an aralkyl group having 7 to 20 carbon atoms, m is each independently an integer of 2 to 20, preferably an integer of 3 to 10, and X is the same as above. )

[0155] Among them, R 2 It is an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an aralkyl group having 7 to 20 carbon atoms, preferably a linear alkyl group having 1 to 8 carbon atoms, and more preferably a linear alkyl group having 2 to 4 carbon atoms.

[0156] As R 2Specific examples include alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, tetradecyl, hexadecyl, octadecyl, isopropyl, isobutyl, tert-butyl, neopentyl, tert-hexyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclohexylmethyl, norbornyl, decahydronaphthyl, adamantyl, and adamantylmethyl; aryl groups such as phenyl, tolyl, and naphthyl; and aralkyl groups such as benzyl, phenylethyl, and phenylpropyl. 2 , preferably ethyl or octyl.

[0157] Examples of the lipophilic group-containing (hydrolyzable) organosilane compound represented by the above formula (2) include compounds represented by the following formulas.

[0158] [Chemistry 21]

[0159]

[0160] Examples of methods for producing the lipophilic group-containing (hydrolyzable) organosilane compound represented by the above formula (1), particularly the lipophilic group-containing (hydrolyzable) organosilane compound wherein Y in the formula (1) is independently an alkylene group having 2 to 20 carbon atoms and R is a methyl group, include the following methods.

[0161] A silane compound having A in the above formula (1) and a phenyldimethylsilyl moiety at the molecular chain end (e.g., dimethylsilane having A in the above formula (1) and a dimethylhydrogensilylphenyl group as a substituent bonded to a silicon atom) is heated and stirred at a temperature of 40 to 120° C., preferably 60 to 100° C., and more preferably about 80° C., and a hydrosilylation reaction catalyst such as a toluene solution of a chloroplatinic acid / vinylsiloxane complex is added. Next, a compound having a hydrolyzable silyl group and an olefin moiety (e.g., an alkenyl group) at the molecular chain end is added dropwise, and the mixture is aged at a temperature of 40 to 120° C., preferably 60 to 100° C., and more preferably about 80° C. for 10 minutes to 12 hours, preferably 1 to 6 hours, and more preferably 3 to 6 hours. In addition, the reaction may be diluted with an organic solvent.

[0162] Among them, examples of the silane compound having A in the above formula (1) and a phenyldimethylsilyl moiety at the molecular chain end include silane compounds represented by the following general formulae (6a), (6b), (6c) and (6d).

[0163] [Chemistry 22]

[0164]

[0165] (Where R 2 , m are the same as above.)

[0166] Specific examples of the silane compound represented by the formula (6a) include the following compounds.

[0167] [Chemistry 23]

[0168]

[0169] [Chemistry 24]

[0170]

[0171] [Chemistry 25]

[0172]

[0173] Specific examples of the silane compound represented by the formula (6b) include the following compounds.

[0174] [Chemistry 26]

[0175]

[0176] Specific examples of the silane compound represented by the formula (6c) include the following compounds.

[0177] [Chemistry 27]

[0178]

[0179] Specific examples of the silane compound represented by the formula (6d) include the following compounds.

[0180] [Chemistry 28]

[0181]

[0182] As a method for preparing the silane compound represented by the above formula (6a), (6b), (6c) and (6d), 1,4-bis(dimethylsilyl)benzene is heated and stirred at a temperature of 40 to 120°C, preferably 60 to 100°C, more preferably about 80°C, and a toluene solution of a hydrosilylation catalyst such as chloroplatinic acid / vinylsiloxane complex is added. Then, a compound having A in the above formula (1) and an olefin site (e.g., alkenyl) at the molecular chain end is slowly added dropwise over a period of time, and the mixture is aged at a temperature of 40 to 120°C, preferably 60 to 100°C, more preferably about 80°C for 10 minutes to 12 hours, preferably 1 to 6 hours. In addition, the reaction may be diluted with an organic solvent.

[0183] Among them, specific examples of the compound having A in the above formula (1) and an olefin site at the molecular chain terminal include the following compounds.

[0184] [Chemical formula 29]

[0185] C2H5OOC-(CH2)2-CH=CH2

[0186] C2H5OOC-(CH2)8-CH=CH2

[0187] C2H5OOC-(CH2) 11 -CH=CH2

[0188] H3COOC-(CH2)8-CH=CH2

[0189] C4H9OOC-(CH2)8-CH=CH2

[0190] C8H 17 OOC-(CH2)8-CH=CH2

[0191]

[0192] [Chemical formula 30]

[0193] (C2H5)2NOC-(CH2)2-CH=CH2

[0194] (C2H5)2NOC-(CH2)8-CH=CH2

[0195] (C4H9)2NOC-(CH2)2-CH=CH2

[0196] (C4H9)2NOC-(CH2)8-CH=CH2

[0197] C2H5SOC-(CH2)2-CH=CH2

[0198] C2H5SOC-(CH2)8-CH=CH2

[0199] C4H9SOC-(CH2)2-CH=CH2

[0200] C4H9SOC-(CH2)8-CH=CH2

[0201]

[0202] (CH3O)2OP-(CH2)2-CH=CH2

[0203] (CH3O)2OP-(CH2)8-CH=CH2

[0204] (C2H5O)2OP-(CH2)2-CH=CH2

[0205] The amount of the compound (C2H5O)2OP-(CH2)8-CH=CH2 having A in the above formula (1) and an olefin portion at the end of the molecular chain is 0.05 to 0.5 equivalents, more preferably 0.1 to 0.4 equivalents, relative to 1 equivalent of 1,4-bis(dimethylsilyl)benzene.

[0206] In the preparation of the silane compounds represented by the above formulae (6a), (6b), (6c) and (6d), as catalysts for the hydrosilylation reaction, platinum black, chloroplatinic acid, alcohol-modified chloroplatinic acid, complexes of chloroplatinic acid with olefins, aldehydes, vinyl siloxanes, acetylenic alcohols, etc., platinum group metal catalysts such as tetrakis(triphenylphosphine)palladium and tris(triphenylphosphine)rhodium chloride can be cited. Platinum compounds such as vinyl siloxane coordination compounds are preferred.

[0207] The amount of the hydrosilylation reaction catalyst used is 0.5 to 100 ppm, more preferably 0.5 to 50 ppm, in terms of transition metal (mass), relative to the total mass of 1,4-bis(dimethylsilyl)benzene and the compound having A in the above formula (1) and an olefin moiety at the molecular chain terminal.

[0208] An organic solvent can be used in the preparation of the silane compound represented by the above formula (6a), (6b), (6c) and (6d). Examples of the organic solvent used include ether solvents (dibutyl ether, diethyl ether, tetrahydrofuran, etc.) and hydrocarbon solvents (petroleum spirit, toluene, xylene, etc.). Among these, toluene is particularly preferred.

[0209] The amount of the solvent used when compounded is 10 to 300 parts by mass, preferably 50 to 150 parts by mass, based on 100 parts by mass of the compound having A in the above formula (1) and an olefin moiety at the molecular chain terminal.

[0210] Next, the reaction is stopped and the solvent is distilled off to obtain the silane compounds represented by the above formulae (6a), (6b), (6c) and (6d).

[0211] In the preparation of the lipophilic group-containing (hydrolyzable) organosilane compound represented by formula (1), the following compounds can be specifically exemplified as compounds having a hydrolyzable silyl group and an olefin moiety (eg, alkenyl group) at the molecular chain ends.

[0212] [Chemistry 31]

[0213] CH2=CH-Si(OCH3)3

[0214] CH2=CH-CH2-Si(OCH3)3

[0215] CH2=CH-(CH2)4-Si(OCH3)3

[0216] CH2=CH-(CH2)6-Si(OCH3)3

[0217] The amount of the compound having a hydrolyzable silyl group and an olefin moiety at the molecular chain end is 1 to 5 equivalents, more preferably 1 to 2.5 equivalents, and even more preferably 1.1 to 2 equivalents, relative to 1 equivalent of the silane compound having A in the above formula (1) and a phenyldimethylsilyl moiety at the molecular chain end.

[0218] In the preparation of the (hydrolyzable) organosilane compound containing a lipophilic group represented by the above formula (1), examples of the hydrosilylation reaction catalyst include platinum black, chloroplatinic acid, alcohol-modified chloroplatinic acid, complexes of chloroplatinic acid with olefins, aldehydes, vinyl siloxanes, acetylenic alcohols, etc., and platinum group metal catalysts such as tetrakis(triphenylphosphine)palladium and tris(triphenylphosphine)rhodium chloride. Platinum compounds such as vinyl siloxane coordination compounds are preferred.

[0219] The amount of the hydrosilylation reaction catalyst used is such that the amount is 0.5 to 100 ppm, more preferably 1 to 50 ppm, in terms of transition metal conversion (mass), relative to the total mass of the silane compound having A in the above formula (1) and a phenyldimethylsilyl moiety at the molecular chain end and the compound having a hydrolyzable silyl group and an olefin moiety at the molecular chain end.

[0220] An organic solvent may be used in the preparation of the (hydrolyzable) organosilane compound containing a lipophilic group represented by the formula (1). Examples of the organic solvent include ether solvents (dibutyl ether, diethyl ether, tetrahydrofuran, etc.) and hydrocarbon solvents (petroleum spirit, toluene, xylene, etc.). Among these, toluene is particularly preferred.

[0221] The amount of the solvent used when blended is 10 to 300 parts by mass, preferably 50 to 150 parts by mass, based on 100 parts by mass of the compound having A in the above formula (1) and a phenyldimethylsilyl moiety at a molecular chain terminal.

[0222] Next, the reaction is terminated, and the solvent and unreacted components are distilled off to obtain the lipophilic group-containing (hydrolyzable) organosilane compound represented by the above formula (1).

[0223] For example, when a compound represented by the following formula is used as a silane compound having A in the above formula (1) and a phenyldimethylsilyl moiety at the molecular chain end,

[0224] [Chemistry 32]

[0225]

[0226] When a compound represented by the following formula is used as the compound having a hydrolyzable silyl group and an olefin moiety at the molecular chain terminal, respectively,

[0227] [Chemistry 33]

[0228] CH2=CH-CH2-Si(OCH3)3

[0229] A compound represented by the following formula was obtained.

[0230] [Chemistry 34]

[0231]

[0232] The organosiloxane compound represented by the following general formula (3)

[0233] [Chemistry 35]

[0234]

[0235] (wherein A' is -CH3, -C(=O)OR 1 、-C(=O)NR 1 2. -C(=O)SR 1 and -P(=O)(OR 1 )2, R 1 is a hydrogen atom, an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, or an aralkyl group having 7 to 30 carbon atoms, Y' is independently a divalent organic group, W is independently an alkyl group having 1 to 4 carbon atoms, a phenyl group, a hydroxyl group, or a hydrolyzable group, R is independently an alkyl group having 1 to 4 carbon atoms or a phenyl group, X is independently a hydroxyl group or a hydrolyzable group, n is an integer of 1 to 3, and q is an integer of 1 to 3.)

[0236] The (hydrolyzable) organosiloxane compound containing a lipophilic group represented by the formula (3) has a lipophilic terminal group, a siloxane skeleton, and preferably a plurality of (i.e., 2 or more), more preferably 2 to 9, and further preferably 3 to 9 silanol groups, or one or more, preferably 2 or 3, and more preferably 3 hydrolyzable silyl groups (i.e., silyl groups each independently having 1 to 3, preferably 2 or 3 hydrolyzable groups), and is excellent in lipophilicity and cutting oil resistance.

[0237] In the above formula (3), A' is -CH3, -C(=O)OR 1 An ester or carboxylic acid represented by -C(=O)NR 1 Amide represented by 2, -C(=O)SR 1 The thioester or thioacid represented by -P(=O)(OR 1) Any of the phosphonate or phosphonic acid represented by )2 is the lipophilic terminal group in the present invention.

[0238] Among them, R 1 is a hydrogen atom, an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, or an aralkyl group having 7 to 30 carbon atoms, and examples thereof include 1 The same group is preferably an ethyl group or an octyl group.

[0239] As A' other than -CH3, for example, the following groups can be exemplified.

[0240] [Chemistry 36]

[0241]

[0242] [Chemistry 37]

[0243]

[0244] (CH3O)2OP-

[0245] (C2H5O)2OP-

[0246] In the above formula (3), W is an alkyl group having 1 to 4 carbon atoms which may be different from each other, a phenyl group, a hydroxyl group or a hydrolyzable group. Examples of such W include alkyl groups such as methyl, ethyl, propyl and butyl groups, phenyl groups, hydroxyl groups, alkoxy groups having 1 to 10 carbon atoms such as methoxy, ethoxy, propoxy, isopropoxy and butoxy groups, alkoxy-substituted alkoxy groups having 2 to 10 carbon atoms such as methoxymethoxy and methoxyethoxy groups, acyloxy groups having 1 to 10 carbon atoms such as acetoxy groups, alkenyloxy groups having 2 to 10 carbon atoms such as isopropenyloxy groups, halogen atoms such as fluorine atoms, chlorine atoms, bromine atoms and iodine atoms, oxime groups, isocyanate groups and cyanate groups. Among them, methyl, methoxy, ethoxy, isopropenyloxy and chlorine atoms are preferred.

[0247] In the above formula (3), X is a hydroxyl group or a hydrolyzable group which may be different from each other, and examples thereof include the same groups as those for X in formula (1), among which a methoxy group, an ethoxy group, an isopropenyloxy group, and a chlorine atom are preferred.

[0248] In the above formula (3), R is an alkyl group having 1 to 4 carbon atoms or a phenyl group, and may be the same group as R in formula (1), and is preferably a methyl group.

[0249] In the above formula (3), Y' is a divalent organic group, preferably a divalent group selected from -O-, -S-, -NR-, -C(=O)-, -C(=O)O-, -C(=O)NR-, -OC(=O)NR- (R is the same as above), a silylene group, a silylene group and a linear, branched or cyclic divalent organic (poly)siloxane residue having 2 to 10 silicon atoms, and an alkylene group having 2 to 30 carbon atoms, particularly 2 to 20 carbon atoms, which may contain an arylene group having 6 to 20 carbon atoms, and more preferably a divalent group represented by the following formula (7).

[0250] [Chemistry 38]

[0251] -R 7 -Z-(R 7 ) a - (7)

[0252] (where Z and a are the same as above, R 7 are independently divalent hydrocarbon groups. )

[0253] In the above formula (7), R 7 The independently divalent hydrocarbon group specifically includes alkylene groups having 1 to 30 carbon atoms such as methylene, ethylene, propylene, butylene, and hexamethylene, and alkylene groups having 7 to 30 carbon atoms including arylene groups having 6 to 20 carbon atoms such as phenylene, and preferably alkylene groups having 2 to 20 carbon atoms.

[0254] Specific examples of Y' include the following groups.

[0255] [Chemistry 39]

[0256] -CH2CH2-

[0257] -CH2CH2CH2-

[0258] -CH2CH2CH2CH2-

[0259] -CH2CH2CH2CH2CH2CH2-

[0260] -CH2CH2CH2CH2CH2CH2CH2-

[0261] -CH2CH2CH2CH2CH2CH2CH2CH2-

[0262] -CH2CH2CH2CH2CH2CH2CH2CH2CH2-

[0263] -CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2-

[0264] -CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2-

[0265] -CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2-

[0266]

[0267] [Chemistry 40]

[0268] -CH2CH2-O-CH2CH2-

[0269] -(CH2) 10 -O-CH2CH2-

[0270]

[0271] -CH2CH2-S-CH2CH2-

[0272]

[0273] [Chemistry 41]

[0274]

[0275] [Chemistry 42]

[0276]

[0277] In the above formula (3), n is an integer of 1 to 3, and q is an integer of 1 to 3. Preferably, n is 2 or 3, and q is 2 or 3. More preferably, n is 3, and q is 3.

[0278] Examples of the lipophilic group-containing (hydrolyzable) organosiloxane compound represented by the above formula (3) include compounds represented by the following formulas.

[0279] [Chemistry 43]

[0280]

[0281] [Chemistry 44]

[0282]

[0283] [Chemistry 45]

[0284]

[0285] [Chemistry 46]

[0286]

[0287] [Chemistry 47]

[0288]

[0289] [Chemistry 48]

[0290]

[0291] [Chemistry 49]

[0292]

[0293] [Chemistry 50]

[0294]

[0295] [Chemistry 51]

[0296]

[0297] The lipophilic group-containing (hydrolyzable) organosiloxane compound represented by the above formula (3) is more preferably represented by the following general formula (4).

[0298] [Chemistry 52]

[0299]

[0300] (Where R 3 is an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an aralkyl group having 7 to 20 carbon atoms, Q is a single bond, or a divalent group selected from a silylene group, a silylene group, and a linear, branched, or cyclic divalent organic (poly)siloxane residue having 2 to 10 silicon atoms, m' is independently an integer of 1 to 20, preferably an integer of 2 to 10, m" is an integer of 2 to 20, preferably an integer of 2 to 10, and X is the same as above.)

[0301] In the above formula (4), R 3 It is an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an aralkyl group having 7 to 20 carbon atoms, and is preferably a linear alkyl group having 1 to 8 carbon atoms.

[0302] As R 3 Specific examples include alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, tetradecyl, hexadecyl, octadecyl, isopropyl, isobutyl, tert-butyl, neopentyl, tert-hexyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclohexylmethyl, norbornyl, decahydronaphthyl, adamantyl, and adamantylmethyl; aryl groups such as phenyl, tolyl, and naphthyl; and aralkyl groups such as benzyl, phenylethyl, and phenylpropyl. 3 , preferably methyl, ethyl, butyl, octyl.

[0303] In the above formula (4), Q is a single bond or a divalent group selected from silanylene groups, silanylene groups and linear, branched or cyclic divalent organo(poly)siloxane residues having 2 to 10 silicon atoms, preferably 2 to 5 silicon atoms.

[0304] Among them, examples of the silylene group, silylene group, and a linear, branched, or cyclic divalent organo(poly)siloxane residue having 2 to 10 silicon atoms, preferably 2 to 5 silicon atoms, can include the same groups as those exemplified as the silylene group, silylene group, or a linear, branched, or cyclic divalent organo(poly)siloxane residue having 2 to 10 silicon atoms, preferably 2 to 5 silicon atoms, in the above-mentioned formulas (5) and (7).

[0305] Examples of the lipophilic group-containing (hydrolyzable) organosiloxane compound represented by the above formula (4) include compounds represented by the following formulas.

[0306] [Chemistry 53]

[0307]

[0308] [Chemistry 54]

[0309]

[0310] Examples of methods for producing the lipophilic group-containing (hydrolyzable) organosiloxane compound represented by the above formula (3), particularly the lipophilic group-containing (hydrolyzable) organosiloxane compound wherein R is a methyl group, include the following methods.

[0311] A siloxane compound (organohydrogensiloxane compound) having A' in the above formula (3) and a plurality of SiH groups (hydrogen atoms bonded to silicon atoms) at the molecular chain ends is heated and stirred at 40 to 120°C, preferably 60 to 100°C, more preferably about 80°C, and a hydrosilylation reaction catalyst such as a toluene solution of a chloroplatinic acid / vinylsiloxane complex is added. Next, a silane compound having a hydrolyzable silyl group and an olefin moiety (e.g., an alkenyl group) at the molecular chain ends is added dropwise, and the mixture is aged at 40 to 120°C, preferably 60 to 100°C, more preferably about 80°C for 10 minutes to 12 hours, preferably 1 to 6 hours. In addition, the reaction may be diluted with an organic solvent.

[0312] Among them, examples of the siloxane compound (organohydrogensiloxane compound) having A′ in the above formula (3) and a plurality of SiH groups at the molecular chain ends thereof include siloxane compounds represented by the following general formula (8).

[0313] [Chemistry 55]

[0314]

[0315] (Wherein, A', Y', W, and q are the same as above.)

[0316] Specific examples of the siloxane compound represented by the formula (8) include organohydrogensiloxane compounds represented by the following general formulae (a) to (j).

[0317] [Chemistry 56]

[0318]

[0319] [Chemistry 57]

[0320]

[0321] [Chemistry 58]

[0322]

[0323] [Chemistry 59]

[0324]

[0325] [Chemistry 60]

[0326]

[0327] [Chemistry 61]

[0328]

[0329] [Chemistry 62]

[0330]

[0331] [Chemistry 63]

[0332]

[0333] [Chemistry 64]

[0334]

[0335] [Chemistry 65]

[0336]

[0337] (Where R 3 , W, m', m", q are the same as above. Q' is a divalent group selected from silylene groups, silylene groups and linear, branched or cyclic divalent organic (poly)siloxane residues having 2 to 10 silicon atoms.)

[0338] Specific examples of the organohydrogensiloxane compound represented by the formula (a) include the following compounds.

[0339] [Chemistry 66]

[0340]

[0341] [Chemistry 67]

[0342]

[0343] [Chemistry 68]

[0344]

[0345] Specific examples of the organohydrogensiloxane compound represented by the formula (b) include the following compounds.

[0346] [Chemistry 69]

[0347]

[0348] [Chemistry 70]

[0349]

[0350] Specific examples of the organohydrogensiloxane compound represented by the formula (c) include the following compounds.

[0351] [Chemistry 71]

[0352]

[0353] [Chemistry 72]

[0354]

[0355] Specific examples of the organohydrogensiloxane compound represented by the formula (d) include the following compounds.

[0356] [Chemistry 73]

[0357]

[0358] [Chemistry 74]

[0359]

[0360] Specific examples of the organohydrogensiloxane compound represented by the formula (e) include the following compounds.

[0361] [Chemistry 75]

[0362]

[0363] [Chemistry 76]

[0364]

[0365] Specific examples of the organohydrogensiloxane compound represented by the formula (f) include the following compounds.

[0366] [Chemistry 77]

[0367]

[0368] [Chemistry 78]

[0369]

[0370] Specific examples of the organohydrogensiloxane compound represented by the formula (g) include the following compounds.

[0371] [Chemistry 79]

[0372]

[0373] [Chemistry 80]

[0374]

[0375] Specific examples of the organohydrogensiloxane compound represented by the formula (h) include the following compounds.

[0376] [Chemistry 81]

[0377]

[0378] [Chemistry 82]

[0379]

[0380] Specific examples of the organohydrogensiloxane compound represented by the formula (i) include the following compounds.

[0381] [Chemistry 83]

[0382]

[0383] Specific examples of the organohydrogensiloxane compound represented by the formula (j) include the following compounds.

[0384] [Chemistry 84]

[0385]

[0386] [Chemistry 85]

[0387]

[0388] As a method for preparing an organohydrogensiloxane compound represented by the above formula (8), particularly formulas (a) to (j), a silane or siloxane compound having A' in the above formula (3) and a hydrolyzable silyl group at the molecular chain end is stirred at a temperature of -20 to 40°C, preferably -10 to 20°C, more preferably 0 to 10°C, a tetramethyldisiloxane (1,3-dihydro-1,1,3,3-tetramethyldisiloxane) or the like tetraorganodisiloxane (1,3-dihydro-1,1,3,3-tetraorganodisiloxane) and a co-hydrolysis reaction catalyst such as hydrochloric acid or sulfuric acid are added dropwise, and the mixture is aged at a temperature of -20 to 40°C, preferably -10 to 20°C, more preferably 0 to 10°C for 10 minutes to 12 hours, preferably 1 to 6 hours. In addition, the mixture may be diluted with an organic solvent during the reaction.

[0389] Among them, examples of the silane or siloxane compound having A′ in the above formula (3) and a hydrolyzable silyl group at the molecular chain end include silane or siloxane compounds represented by the following general formula (9).

[0390] [Chemistry 86]

[0391]

[0392] (Wherein, A', Y', W, and q are the same as above.)

[0393] Specific examples of the silane or siloxane compound represented by formula (9) include the following compounds: Furthermore, examples of the siloxane compound represented by formula (9) include the organosilane compound represented by formula (1) described above.

[0394] [Chemistry 87]

[0395] C2H5-OOC-(CH2)4-Si(OCH3)3

[0396] C2H5-OOC-(CH2) 10 -Si(OCH3)3

[0397] C2H5-OOC-(CH2) 13 -Si(OCH3)3

[0398] [Chemistry 88]

[0399] CH3-OOC-(CH2) 10 -Si(OCH3)3

[0400] C4H9-OOC-(CH2) 10 -Si(OCH3)3

[0401]

[0402] [Chemistry 89]

[0403]

[0404] [Chemistry 90]

[0405]

[0406] [Chemistry 91]

[0407] (C2H5)2-NOC-(CH2)4-Si(OCH3)3

[0408] (C2H5)2-NOC-(CH2) 10 -Si(OCH3)3

[0409] (C4H9)2-NOC-(CH2) 10 -Si(OCH3)3

[0410] [Chemistry 92]

[0411]

[0412] [Chemistry 93]

[0413]

[0414] [Chemistry 94]

[0415] CH3-SOC-(CH2) 10 -Si(OCH3)3

[0416] C2H5-SOC-(CH2)4-Si(OCH3)3

[0417] C2H5-SOC-(CH2) 10 -Si(OCH3)3

[0418] C4H9-SOC-(CH2) 10 -Si(OCH3)3

[0419]

[0420] [Chemistry 95]

[0421]

[0422] [Chemistry 96]

[0423]

[0424] [Chemistry 97]

[0425] (CH3O)2OP-(CH2)4-Si(OCH3)3

[0426] (CH3O)2OP-(CH2) 10 -Si(OCH3)3

[0427] (C2H5O)2OP-(CH2) 10 -Si(OCH3)3

[0428] [Chemistry 98]

[0429]

[0430] [Chemistry 99]

[0431]

[0432] [Chemical 100]

[0433] CH3-(CH2)4-Si(OCH3)3

[0434] CH3-(CH2) 10 -Si(OCH3)3

[0435] [Chemistry 101]

[0436]

[0437] [Chemistry 102]

[0438]

[0439] [Chemistry 103]

[0440]

[0441] [Chemistry 104]

[0442]

[0443] A silane or siloxane compound represented by formula (9) having A' in the above formula (3) and a hydrolyzable silyl group at the end of the molecular chain, in particular a silane compound in which Y' in formula (9) is an alkylene group containing a silylene group, can be obtained by the method exemplified in the above-mentioned method for preparing an organic silane compound represented by formula (1).

[0444] A method for preparing a silane or siloxane compound represented by formula (9) having A' in the above formula (3) and a hydrolyzable silyl group at the ends of the molecular chain, in particular, a silane or siloxane compound in which Y' in formula (9) is an alkylene group containing a divalent group selected from a silylene group and a linear, branched or cyclic divalent organic (poly)siloxane residue having 2 to 10 silicon atoms, comprising heating and stirring the compound having two SiH groups at the ends of the molecular chain at a temperature of 40 to 120° C., preferably 60 to 100° C., more preferably about 80° C., and adding a hydrosilylation reaction catalyst such as a toluene solution of a chloroplatinic acid / vinylsiloxane complex. Next, a compound having A' in the above formula (3) and an olefin part (e.g., alkenyl) at the end of the molecular chain is slowly dripped over a period of time, and ripened at a temperature of 40 to 120° C., preferably 60 to 100° C., for 10 minutes to 12 hours, preferably 30 minutes to 6 hours, thereby obtaining a silane or siloxane compound having A' in the above formula (3) and a terminal SiH group at the end of the molecular chain. In addition, the reaction may be diluted with an organic solvent.

[0445] Next, the silane or siloxane compound having A' in the above formula (3) and a terminal SiH group at the molecular chain end is heated and stirred at 40 to 120° C., preferably 60 to 100° C., and a hydrosilylation catalyst such as a toluene solution of a chloroplatinic acid / vinylsiloxane complex is added. Next, a silane compound having a hydrolyzable silyl group and an olefin moiety (e.g., an alkenyl group) at the molecular chain end is added dropwise, and the mixture is aged at 40 to 120° C., preferably 60 to 100° C. for 10 minutes to 12 hours, preferably 1 to 6 hours. In addition, the reaction may be diluted with an organic solvent.

[0446] Among them, specific examples of the compound having two SiH groups at the molecular chain terminals include the following compounds.

[0447] [Chemistry 105]

[0448]

[0449] Specific examples of the compound having A′ and an olefin moiety in the above formula (3) at the molecular chain end include the following compounds.

[0450] [Chemistry 106]

[0451] C2H5OOC-(CH2)2-CH=CH2

[0452] C2H5OOC-(CH2)8-CH=CH2

[0453] C2H5OOC-(CH2) 11-CH=CH2

[0454] H3COOC-(CH2)8-CH=CH2

[0455] C4H9OOC-(CH2)8-CH=CH2

[0456] C8H 17 OOC-(CH2)8-CH=CH2

[0457]

[0458] [Chemical formula 107]

[0459] (C2H5)2NOC-(CH2)2-CH=CH2

[0460] (C2H5)2NOC-(CH2)8-CH=CH2

[0461] (C4H9)2NOC-(CH2)2-CH=CH2

[0462] (C4H9)2NOC-(CH2)8-CH=CH2

[0463] C2H5SOC-(CH2)2-CH=CH2

[0464] C2H5SOC-(CH2)8-CH=CH2

[0465] C4H9SOC-(CH2)2-CH=CH2

[0466] C4H9SOC-(CH2)8-CH=CH2

[0467]

[0468] (CH3O)2OP-(CH2)2-CH=CH2

[0469] (CH3O)2OP-(CH2)8-CH=CH2

[0470] (C2H5O)OP-(CH2)2-CH=CH2

[0471] (C2H5O)2OP-(CH2)8-CH=CH2

[0472] CH3-(CH2)8-CH=CH2

[0473] CH3-(CH2)2-CH=CH2

[0474] The amount of the compound having A' and an olefin moiety in the formula (3) at the molecular chain ends is 0.05 to 0.5 equivalents, more preferably 0.1 to 0.4 equivalents, based on 1 equivalent of the compound having two SiH groups at the molecular chain ends.

[0475] In the preparation of the silane or siloxane compound represented by the above formula (9), examples of the hydrosilylation reaction catalyst include platinum black, chloroplatinic acid, alcohol-modified chloroplatinic acid, complexes of chloroplatinic acid with olefins, aldehydes, vinyl siloxanes, acetylenic alcohols, etc., and platinum group metal catalysts such as tetrakis(triphenylphosphine)palladium and tris(triphenylphosphine)rhodium chloride. Platinum compounds such as vinyl siloxane coordination compounds are preferred.

[0476] Regarding the amount of the hydrosilylation catalyst used in the reaction of the compound having two SiH groups at the ends of the molecular chain and the compound having A' in the above formula (3) and an olefin portion at the ends of the molecular chain, the amount used is 0.1 to 100 ppm, more preferably 0.5 to 50 ppm, in terms of transition metal conversion (mass), relative to the total mass of the compound having two SiH groups at the ends of the molecular chain and the compound having A' in the above formula (3) and an olefin portion at the ends of the molecular chain.

[0477] In the preparation of the silane or siloxane compound represented by the above formula (9), an organic solvent can be used. As the organic solvent used, ether solvents (dibutyl ether, diethyl ether, tetrahydrofuran, etc.) and hydrocarbon solvents (petroleum spirit, toluene, xylene, etc.) can be exemplified. Among these, toluene is particularly preferred.

[0478] The amount of the organic solvent used in the reaction of the compound having two SiH groups at the ends of the molecular chain and the compound having A' and an olefin portion in the above formula (3) at the ends of the molecular chain, respectively, is 10 to 300 parts by mass, preferably 50 to 150 parts by mass, relative to 100 parts by mass of the compound having A' and an olefin portion in the above formula (3) at the ends of the molecular chain, respectively.

[0479] Next, the reaction is stopped and the organic solvent is distilled off to obtain a silane or siloxane compound having A′ in the above formula (3) and a terminal SiH group at the molecular chain terminal.

[0480] In the preparation of the silane or siloxane compound represented by the above formula (9), specific examples of the silane compound having a hydrolyzable silyl group and an olefin moiety (eg, alkenyl group) at the molecular chain end include the following compounds.

[0481] [Chemistry 108]

[0482] CH2=CH-Si(OCH3)3

[0483] CH2=CH-CH2-Si(OCH3)3

[0484] CH2=CH-(CH2)4-Si(OCH3)3

[0485] CH2=CH-(CH2)6-Si(OCH3)3

[0486]

[0487] The amount of the silane compound having a hydrolyzable silyl group and an olefin moiety at the molecular chain terminal is 1 to 5 equivalents, more preferably 1.1 to 2.5 equivalents, based on 1 equivalent of the silane or siloxane compound having A' in the above formula (3) and a terminal SiH group at the molecular chain terminal obtained above.

[0488] In the preparation of the silane or siloxane compound represented by the above formula (9), the amount of the hydrosilylation catalyst used in the reaction of the silane or siloxane compound having A' in the above formula (3) and a terminal SiH group at the molecular chain end and the silane compound having a hydrolyzable silyl group and an olefin moiety at the molecular chain end is 0.1 to 100 ppm, more preferably 0.5 to 50 ppm, in terms of transition metal conversion (mass), relative to the total mass of the silane or siloxane compound having A' in the above formula (3) and a terminal SiH group at the molecular chain end and the silane compound having a hydrolyzable silyl group and an olefin moiety at the molecular chain end.

[0489] In the preparation of the silane or siloxane compound represented by the above formula (9), when an organic solvent is used in the reaction of the silane or siloxane compound having A' in the above formula (3) and a terminal SiH group at the molecular chain end obtained above and the silane compound having a hydrolyzable silyl group and an olefin portion at the molecular chain end, as the organic solvent, the same organic solvent as mentioned above can be exemplified, and the amount of the organic solvent used is 10 to 300 parts by mass, preferably 50 to 150 parts by mass, relative to 100 parts by mass of the silane or siloxane compound having A' in the above formula (3) and a terminal SiH group at the molecular chain end obtained above.

[0490] Next, the reaction is stopped and the organic solvent and unreacted components are distilled off to obtain a silane or siloxane compound represented by the above formula (9), particularly a silane or siloxane compound in which Y' in the formula (9) is an alkylene group containing a divalent group selected from a silylene group and a linear, branched or cyclic divalent organic (poly)siloxane residue having 2 to 10 silicon atoms.

[0491] In addition, as a method for preparing a silane or siloxane compound represented by formula (9) having A' in the above formula (3) and a hydrolyzable silyl group at the end of the molecular chain, in particular, a silane compound in which Y' in formula (9) is an alkylene group, the above-mentioned compound having A' in the above formula (3) and an olefin part (for example, an alkenyl group) at the end of the molecular chain is heated and stirred at a temperature of 40 to 120°C, preferably 60 to 100°C, and more preferably about 80°C, and a toluene solution of a hydrosilylation reaction catalyst such as a chloroplatinic acid / vinylsiloxane complex is added. Next, a silane compound having a hydrolyzable silyl group and a SiH group at the molecular chain end is slowly added dropwise over a period of time, and aged at a temperature of 40 to 120° C., preferably 60 to 100° C., more preferably about 80° C. for 10 minutes to 12 hours, preferably 30 minutes to 6 hours, thereby obtaining a silane or siloxane compound having A′ in the above formula (3) and a hydrolyzable silyl group, particularly a silane compound in which Y′ in the formula (9) is an alkylene group. In addition, the reaction may be diluted with an organic solvent.

[0492] Among them, specific examples of the silane compound having a hydrolyzable silyl group and a SiH group at the molecular chain terminal include the following compounds.

[0493] [Chemistry 109]

[0494] H-Si(OCH3)3

[0495]

[0496] The amount of the compound having A' in the above formula (3) and an olefin moiety (eg, alkenyl) at the molecular chain end is 0.2 to 1 equivalent, more preferably 0.4 to 0.8 equivalent, based on 1 equivalent of the silane compound having a hydrolyzable silyl group and a SiH group at the molecular chain end.

[0497] In the preparation of the silane compound in which Y' in the above formula (9) is an alkylene group, the same catalyst as mentioned above can be exemplified as a hydrosilylation reaction catalyst, and the amount of the hydrosilylation reaction catalyst used is an amount that satisfies 0.1 to 100 ppm, more preferably 0.5 to 50 ppm, in terms of transition metal conversion (mass), relative to the total mass of the compound having A' and an olefin portion in the above formula (3) at the end of the molecular chain and the silane compound having a hydrolyzable silyl group and a SiH group at the end of the molecular chain.

[0498] In the preparation of the silane compound in which Y' in the above formula (9) is an alkylene group, when an organic solvent is used, the same organic solvent as mentioned above can be exemplified as the organic solvent, and the amount of the organic solvent used is 10 to 300 parts by mass, preferably 50 to 150 parts by mass, relative to 100 parts by mass of the compound having A' and an olefin portion in the above formula (3) at the end of the molecular chain.

[0499] In the preparation of the organohydrogensiloxane compounds represented by the above formula (8), especially formulas (a) to (j), the amount of silane or siloxane compound having A' in the above formula (3) and a hydrolyzable silyl group at the end of the molecular chain is 0.2 to 0.6 equivalents, more preferably 0.3 to 0.5 equivalents, relative to 1 equivalent of tetraorganodisiloxane.

[0500] In the preparation of the organohydrogensiloxane compound represented by the above formula (8), especially formulas (a) to (j), examples of the co-hydrolysis reaction catalyst include organotin compounds (dibutyl dimethoxytin, dibutyl tin dilaurate, etc.), organotitanium compounds (tetra-n-butyl titanate, etc.), organic acids (acetic acid, methanesulfonic acid, etc.), and inorganic acids (hydrochloric acid, sulfuric acid, phosphoric acid, etc.). Among these, hydrochloric acid and sulfuric acid are preferred.

[0501] The amount of the co-hydrolysis reaction catalyst used is 1 to 5 equivalents, more preferably 2 to 4 equivalents, based on 1 equivalent of the silane or siloxane compound having A′ in the above formula (3) and a hydrolyzable silyl group at the molecular chain terminal.

[0502] An organic solvent may be used in the preparation of the organohydrogensiloxane compound represented by the above formula (8), especially formulas (a) to (j). Examples of the organic solvent used include ether solvents (dibutyl ether, diethyl ether, tetrahydrofuran, etc.), hydrocarbon solvents (petroleum spirit, toluene, xylene, etc.), and fluorine solvents (perfluorohexane, 1,4-bis(trifluoromethyl)benzene, etc.). Among these, toluene and 1,4-bis(trifluoromethyl)benzene are particularly preferred.

[0503] The amount of the organic solvent used is 10 to 300 parts by mass, preferably 50 to 150 parts by mass, based on 100 parts by mass of the silane or siloxane compound having A′ in the above formula (3) and a hydrolyzable silyl group at a molecular chain terminal.

[0504] Next, the reaction is stopped and the organic solvent is distilled off to obtain the organohydrogensiloxane compound represented by the above formula (8), particularly formulas (a) to (j).

[0505] In the preparation of the lipophilic group-containing (hydrolyzable) organosiloxane compound represented by formula (3), specific examples of the silane compound having a hydrolyzable silyl group and an olefin moiety (eg, alkenyl group) at the molecular chain ends thereof include the following compounds.

[0506] [Chemistry 110]

[0507] CH2=CH-Si(OCH3)3

[0508] CH2=CH-CH2-Si(OCH3)3

[0509] CH2=CH-(CH2)4-Si(OCH3)3

[0510] CH2=CH-(CH2)6-Si(OCH3)3

[0511]

[0512] The amount of the silane compound having a hydrolyzable silyl group and an olefin moiety at the molecular chain terminal is 3 to 5 equivalents, more preferably 3.5 to 4.5 equivalents, based on 1 equivalent of the organohydrogensiloxane compound having A' in the above formula (3) and a plurality of SiH groups at the molecular chain terminal.

[0513] In the preparation of the (hydrolyzable) organosiloxane compound containing a lipophilic group represented by the above formula (3), examples of the hydrosilylation reaction catalyst include platinum black, chloroplatinic acid, alcohol-modified chloroplatinic acid, complexes of chloroplatinic acid with olefins, aldehydes, vinyl siloxanes, acetylenic alcohols, etc., and platinum group metal catalysts such as tetrakis(triphenylphosphine)palladium and tris(triphenylphosphine)rhodium chloride. Platinum compounds such as vinyl siloxane coordination compounds are preferred.

[0514] The amount of the hydrosilylation reaction catalyst used is an amount that satisfies 0.1 to 100 ppm, more preferably 0.2 to 50 ppm, in terms of transition metal conversion (mass), relative to the total mass of the organohydrogensiloxane compound having A' in the above formula (3) and multiple SiH groups at the ends of the molecular chain and the silane compound having a hydrolyzable silyl group and an olefin moiety at the ends of the molecular chain.

[0515] An organic solvent may be used in the preparation of the (hydrolyzable) organosiloxane compound containing a lipophilic group represented by the above formula (3). Examples of the organic solvent used include ether solvents (dibutyl ether, diethyl ether, tetrahydrofuran, etc.) and hydrocarbon solvents (petroleum spirit, toluene, xylene, etc.). Of these, toluene is particularly preferred.

[0516] The amount of the organic solvent used is 10 to 300 parts by mass, preferably 50 to 150 parts by mass, based on 100 parts by mass of the organohydrogensiloxane compound having A′ in the formula (3) and a plurality of SiH groups at molecular chain ends.

[0517] Next, the reaction is terminated, and the organic solvent and unreacted components are distilled off to obtain the lipophilic group-containing (hydrolyzable) organosiloxane compound represented by the above formula (3).

[0518] For example, when a compound represented by the following formula is used as an organohydrogensiloxane compound having A′ in the above formula (3) and a plurality of SiH groups at the molecular chain ends,

[0519] [Chemistry 111]

[0520]

[0521] As the silane compound having a hydrolyzable silyl group and an olefin moiety at the molecular chain end, a compound represented by the following formula is used:

[0522] [Chemistry 112]

[0523] CH2=CH-(CH2)6-Si(OCH3)3

[0524] In the case of , a siloxane compound represented by the following formula is obtained.

[0525] [Chemistry 113]

[0526]

[0527] The (hydrolyzable) organosilane compound containing a lipophilic group represented by the general formula (1) or the (hydrolyzable) organosiloxane compound containing a lipophilic group represented by the general formula (3) obtained by the above reaction is subjected to purification and separation operations such as concentration, column purification, distillation, extraction, etc., and the reaction solution can be used as a mixture containing the (hydrolyzable) organosilane compound containing a lipophilic group represented by the general formula (1) or the (hydrolyzable) organosiloxane compound containing a lipophilic group represented by the general formula (3) as it is, or it can be further diluted with an organic solvent and used.

[0528] By using the (hydrolyzable) organosilane or organosiloxane compound containing a lipophilic group obtained above as a surface treatment agent for various optical components, high lipophilicity can be imparted to the substrate surface, thereby preventing the transparency of the optical component from decreasing even when oil stains adhere to the surface.

[0529] The surface treatment agent of the present invention may be used alone or in combination of two or more of the above-mentioned (hydrolyzable) organosilane or organosiloxane compound containing a lipophilic group. In addition, the surface treatment agent may include a partial condensate obtained by partially condensing the hydroxyl groups of the organosilane or organosiloxane compound containing a lipophilic group, or a partial hydrolysis-condensation product obtained by condensing the hydroxyl groups of the terminal hydrolyzable organosilane or organosiloxane compound containing a lipophilic group in advance by partially hydrolyzing the terminal hydrolyzable groups by a known method.

[0530] The surface treatment agent may contain an appropriate solvent. Examples of such solvents include alcohol solvents (propylene glycol monomethyl ether, butanol, isopropyl alcohol, etc.), ether solvents (dibutyl ether, ethyl ether, tetrahydrofuran, etc.), hydrocarbon solvents (petroleum spirit, toluene, xylene, etc.), and ketone solvents (acetone, methyl ethyl ketone, methyl isobutyl ketone, etc.). Among these, alcohol solvents and ether solvents are preferred in terms of solubility, wettability, etc., and propylene glycol monomethyl ether and dibutyl ether are particularly preferred.

[0531] The above solvents may be a mixture of two or more thereof, preferably allowing the (hydrolyzable) organosilane or organosiloxane compound containing a lipophilic group and a functional group having adhesion to a substrate, such as a lipophilic group-containing (hydrolyzable) organosilane or organosiloxane compound and a partial (hydrolyzed) condensate thereof, to be uniformly dissolved. The optimum concentration of the organosilane or organosiloxane compound containing a lipophilic group and a functional group having adhesion to a substrate dissolved in the solvent varies depending on the treatment method, and any concentration that can be easily weighed may be used. In the case of direct coating, the concentration is preferably 0.01 to 10 parts by mass, and particularly preferably 0.05 to 5 parts by mass, relative to 100 parts by mass of the total of the solvent and the organosilane or organosiloxane compound containing a lipophilic group and a functional group having adhesion to a substrate. In the case of vapor deposition treatment, the concentration is preferably 1 to 100 parts by mass, and particularly preferably 3 to 30 parts by mass, relative to 100 parts by mass of the total of the solvent and the organosilane or organosiloxane compound containing a lipophilic group and a functional group having adhesion to a substrate. In the case of wet treatment, the concentration is preferably 0.01 to 10 parts by mass, and particularly preferably 0.05 to 1 part by mass, relative to 100 parts by mass of the total of the solvent and the organosilane or organosiloxane compound containing a lipophilic group and a functional group having adhesion to a substrate.

[0532] A hydrolysis condensation catalyst may be added to the surface treatment agent, such as an organic tin compound (dibutyl dimethoxytin, dibutyl tin dilaurate, etc.), an organic titanium compound (tetra-n-butyl titanate, etc.), an organic acid (acetic acid, methanesulfonic acid, etc.), an inorganic acid (hydrochloric acid, sulfuric acid, phosphoric acid, etc.). Among these, acetic acid, tetra-n-butyl titanate, dibutyl tin dilaurate, etc. are particularly preferred.

[0533] The amount of the hydrolysis condensation catalyst added is preferably 0.1 to 150 parts by mass, particularly preferably 25 to 125 parts by mass, and further preferably 50 to 110 parts by mass, based on 100 parts by mass of the organosilane or organosiloxane compound containing a lipophilic group and a functional group having adhesion to a substrate.

[0534] The surface treatment agent can be applied to the optical component by known methods such as brush coating, dipping, spraying, and evaporation. The heating method during the evaporation treatment may be a resistance heating method or an electron beam heating method, and is not particularly limited. In addition, the curing temperature varies depending on the curing method. For example, in the case of direct coating (brush coating, dipping, spraying, etc.), it is preferably 25 to 200°C, especially 25 to 150°C for 15 minutes to 36 hours, especially 30 minutes to 24 hours. It can be cured under humidification. In addition, in the case of applying by evaporation treatment, the range of 20 to 200°C is preferred. It can be cured under humidification. The film thickness of the cured film is appropriately selected according to the type of substrate, preferably more than 2nm and less than 100nm. The lower limit of the film thickness is more preferably more than 2.5nm, and more preferably more than 3nm. The upper limit of the film thickness is more preferably less than 90nm, and more preferably less than 50nm. In addition, for example, in the case of spray coating, if the material is diluted in a solvent to which water has been added in advance and hydrolyzed, that is, Si-OH is generated before spray coating, curing after coating will be rapid.

[0535] The substrate treated with the surface treatment agent is not particularly limited as long as it is a substrate for optical components, and may be a substrate of various materials such as glass, plastic, ceramic, quartz, etc. The surface treatment agent can form a cured film having excellent lipophilicity on the above substrate.

[0536] As optical components treated with the surface treatment agent of the present invention, there can be listed car navigation, mobile phones, smart phones, digital cameras, digital video cameras, PDAs, portable audio players, car audio, game consoles, eyeglass lenses, camera lenses, lens covers, lens filters, sunglasses, medical devices such as gastroscopes, copiers, PCs, liquid crystal displays, organic EL displays, plasma displays, touch panel displays, protective films, anti-reflection films, etc. In the present invention, it is particularly preferred to use eyeglass lenses, camera lenses, and lens covers from the aspect of imparting transparency when oil stains adhere.

[0537] Example

[0538] The present invention will be described in more detail below with reference to synthesis examples, examples and comparative examples, but the present invention is not limited to the following examples.

[0539] [Synthesis example 1]

[0540] 45.7 g (2.35 × 10 -1 mol) was heated to 80°C. Then, 1.0×10 -2 g (calculated as Pt single substance, containing 3.0×10 -7 mol), 10.0 g (4.71 × 10 -2 mol), heated and stirred for 1 hour. Then, the solvent and unreacted products were removed under reduced pressure to obtain the following formula (A):

[0541] [Chemistry 114]

[0542]

[0543] The product represented was 18.0 g.

[0544] 1 H-NMR

[0545] δ0.2-0.4(-Si-C H3 )12H

[0546] δ0.7(-(CH2)7CH2-Si-)2H

[0547] δ1.2-1.5(-(C H2 )7-,-OCH2C H3 )17H

[0548] δ1.6(-OOC-CH2C H2 (CH2)7CH2-Si-)2H

[0549] δ2.3(-OOC-C H2 -)2H

[0550] δ4.1(-OC H2 CH3)2H

[0551] δ4.4(-Si-H)1H

[0552] δ7.5(-Si-C6 H4 -Si-)4H

[0553] The above-obtained

[0554] [Chemistry 115]

[0555]

[0556] The compound represented by 10.0 g (2.46 × 10-2 mol) was heated to 80°C. Then, 1.0×10 -2 g (calculated as Pt single substance, containing 3.0×10 -7 mol), then 8.00 g (4.92 × 10 -2 mol), heated and stirred for 3 hours. Then, the solvent and unreacted products were removed under reduced pressure to obtain the following formula (B):

[0557] [Chemistry 116]

[0558]

[0559] The expressed product (Compound 1) was 13.1 g.

[0560] 1 H-NMR

[0561] δ0.2-0.3(-Si-C H3 )12H

[0562] δ0.7(-(CH2)7C H2 -Si-, -SiC H2 CH2CH2-Si(OCH3)3)4H

[0563] δ0.8(-SiCH2CH2CH2-Si(OCH3)3)2H

[0564] δ1.2-1.4(-(C H2 )7-,-OCH2CH3)17H

[0565] δ1.5(-SiCH2C H2 CH2-Si(OCH3)3)2H

[0566] δ1.6(-OOC-CH2C H2 (CH2)7CH2-Si-)2H

[0567] δ2.3(-OOC-C H2 -)2H

[0568] δ3.5(-SiCH2CH2CH2-Si(OC H3 )3)9H

[0569] δ4.1(-OC H2 CH3)2H

[0570] δ7.5(-Si-C6 H4 -Si-)4H

[0571] [Synthesis example 2]

[0572] 10.0 g (4.71 × 10 -2 mol) was heated to 80°C. Then, 1.0×10 -2 g (calculated as Pt single substance, containing 3.0×10 -7 mol), 8.6 g (7.06 × 10 -2 mol), heated and stirred for 1 hour. Then, the solvent and unreacted products were removed under reduced pressure to obtain the following formula (C):

[0573] [Chemistry 117]

[0574] C2H5-OOC-(CH2) 10 -Si(OCH3)3 (C)

[0575] The expressed compound was 12.1 g.

[0576] 1 H-NMR

[0577] δ0.8(-(CH2)7C H2 -Si(OCH3)3)2H

[0578] δ1.2-1.4(-(C H2 )7-,-OCH2C H3 )17H

[0579] δ1.6(-OOC-CH2C H2 (CH2)7CH2-Si-)2H

[0580] δ2.3(-OOC-C H2 -)2H

[0581] δ3.5(-Si(OC H3 )3)9H

[0582] δ4.1(-OC H2 CH3)2H

[0583] 4.5 g (3.4 × 10 -2 mol), 3.6 g of 12N hydrochloric acid solution (4.3 × 10 -2 mol) and 2.5 g of 1,4-bis(trifluoromethyl)benzene were cooled to 0°C. Then, the above-synthesized product of the following formula (C) was added dropwise.

[0584] [Chemistry 118]

[0585] C2H5-OOC-(CH2) 10 -Si(OCH3)3 (C)

[0586] The compound represented by 5.0g (1.5×10 -2 mol), and aged at 0°C for 6 hours. Then, the lower layer was recovered by liquid separation operation, and the solvent and unreacted products were removed by reduced pressure distillation to obtain the following formula (D):

[0587] [Chemistry 119]

[0588]

[0589] The product weight was 5.8 g.

[0590] 1 H-NMR

[0591] δ0.1-0.2(-Si-C H3 )18H

[0592] δ0.5(-(CH2)7C H2 -Si(O-Si(CH3)2-)3)2H

[0593] δ1.2-1.5(-(C H2 )7-,-OCH2C H3 )17H

[0594] δ1.6(-OOC-CH2C H2 (CH2)7CH2-Si-)2H

[0595] δ2.3(-OOC-C H2 -)2H

[0596] δ4.1(-OC H2 CH3)2H

[0597] δ4.7(-Si-H)3H

[0598] The above-obtained

[0599] [Chemistry 120]

[0600]

[0601] The compound represented by 5.0g (1.1×10 -2 mol) was heated to 80°C. Then, 5.0×10 -3 g (calculated as Pt single substance, containing 1.5×10-7 mol), then 7.3 g (4.5 × 10 -2 mol), heated and stirred for 3 hours. Then, the solvent and unreacted products were removed under reduced pressure to obtain the following formula (E):

[0602] [Chemistry 121]

[0603]

[0604] The expressed product (Compound 2) was 8.8 g.

[0605] 1 H-NMR

[0606] δ0.1-0.2(-Si-C H3 )18H

[0607] δ0.5(-(CH2)7C H2 -Si(O-Si(CH3)2-)3)2H

[0608] δ0.6-0.8(-SiCH2CH2C H2 -Si(OCH3)3, -SiC H2 CH2CH2-Si(OCH3)3)12H

[0609] δ1.2-1.4(-(C H2 )7-,-OCH2C H3 )17H

[0610] δ1.5(-SiCH2C H2 CH2-Si(OCH3)3)6H

[0611] δ1.6(-OOC-CH2C H2 (CH2)7CH2-Si-)2H

[0612] δ2.3(-OOC-C H2 -)2H

[0613] δ3.5(-SiCH2CH2CH2-Si(OC H3 )3)27H

[0614] δ4.1(-OC H2 CH3)2H

[0615] [Synthesis example 3]

[0616] 5.3 g (4.0 × 10 -2 mol), 4.3 g (5.2 × 10-2 mol) and 5.0 g of 1,4-bis(trifluoromethyl)benzene were cooled to 0°C. Then, the above-synthesized product of the following formula (B) was added dropwise.

[0617] [Chemistry 122]

[0618]

[0619] The compound represented by 10.0 g (1.8 × 10 -2 mol), and aged at 0°C for 6 hours. Then, the lower layer was recovered by liquid separation operation, and the solvent and unreacted products were removed by reduced pressure distillation to obtain the following formula (F):

[0620] [Chemistry 123]

[0621]

[0622] The product weight was 8.2 g.

[0623] 1 H-NMR

[0624] δ0.1-0.2(-Si-C H3 )30H

[0625] δ0.5(-(CH2)7C H2 -Si(O-Si(CH3)2-)3)2H

[0626] δ0.7-0.8(-C6H4-Si-C H2 -)4H

[0627] δ1.2-1.5(-(C H2 )7-,-OCH2C H3 , -Si-CH2C H2 CH2-Si-)19H

[0628] δ1.6(-OOC-CH2C H2 (CH2)7CH2-Si-)2H

[0629] δ2.3(-OOC-C H2 -)2H

[0630] δ4.1(-OC H2 CH3)2H

[0631] δ4.7(-Si-H)3H

[0632] δ7.5(-Si-C6 H4 -Si-)4H

[0633] The above-obtained compound of the following formula (F) is placed in a reaction container.

[0634] [Chemistry 124]

[0635]

[0636] The compound represented by 6.0g (8.6×10 -3 mol) was heated to 80°C. Then, 5.0×10 -3 g (calculated as Pt single substance, containing 1.5×10 -7 mol), then 5.8 g (3.6 × 10 -2 mol), heated and stirred for 3 hours. Then, the solvent and unreacted products were removed under reduced pressure to obtain the following formula (G):

[0637] [Chemistry 125]

[0638]

[0639] The expressed product (Compound 3) was 9.4 g.

[0640] 1 H-NMR

[0641] δ0.1-0.2(-Si-C H3 )30H

[0642] δ0.5(-(CH2)7C H2 -Si(O-Si(CH3)2-)3)2H

[0643] δ0.6-0.8(-C6H4-Si-C H2 -,-SiCH2CH2C H2 -Si(OCH3)3, -SiC H2 CH2CH2-Si(OCH3)3)16H

[0644] δ1.2-1.4(-(C H2 )7-,-OCH2C H3 , -Si-CH2C H2 CH2-Si-)19H

[0645] δ1.5(-SiCH2C H2 CH2-Si(OCH3)3)6H

[0646] δ1.6(-OOC-CH2C H2 (CH2)7CH2-Si-)2H

[0647] δ2.3(-OOC-C H2 -)2H

[0648] δ3.5(-SiCH2CH2CH2-Si(OC H3 )3)27H

[0649] δ4.1(-OC H2 CH3)2H

[0650] δ7.5(-Si-C6 H4 -Si-)4H

[0651] [Synthesis Example 4]

[0652] The above-obtained

[0653] [Chemistry 126]

[0654]

[0655] The compound represented by 10.0 g (2.46 × 10 -2 mol) was heated to 80°C. Then, 1.0×10 -2 g (calculated as Pt single substance, containing 3.0×10 -7 mol), 9.10 g (3.94 × 10 -2 mol), heated and stirred for 4 hours. Then, the solvent and unreacted products were removed under reduced pressure to obtain the following formula (H):

[0656] [Chemistry 127]

[0657]

[0658] The expressed compound was 14.0 g.

[0659] 1 H-NMR

[0660] δ0.2(-Si-C H3 )12H

[0661] δ0.6(-SiC H2 (CH2)6CH2-Si(OCH3)3)4H

[0662] δ0.7(-(CH2)7C H2 -Si-, -SiCH2(CH2)6C H2 -Si(OCH3)3)2H

[0663] δ1.2-1.4(-(C H2 )7-,-(C H2 )6-,-OCH2C H3 )31H

[0664] δ1.6(-OOC-CH2C H2 (CH2)7CH2-Si-)2H

[0665] δ2.3(-OOC-C H2 -)2H

[0666] δ3.5(-SiCH2(CH2)6CH2-Si(OC H3 )3)9H

[0667] δ4.1(-OC H2 CH3)2H

[0668] δ7.5(-Si-C6 H4 -Si-)4H

[0669] 3.3 g (2.5 × 10 -2 mol), 12N hydrochloric acid aqueous solution 2.6g (3.1×10 -2 mol) and 3.5 g of 1,4-bis(trifluoromethyl)benzene were cooled to 0°C. Then, the above-synthesized product of the following formula (H) was added dropwise.

[0670] [Chemistry 128]

[0671]

[0672] The compound represented by 7.0 g (1.1 × 10 -2 mol), and aged at 0°C for 6 hours. Then, the lower layer was recovered by liquid separation operation, and the solvent and unreacted products were removed by reduced pressure distillation to obtain the following formula (I):

[0673] [Chemistry 129]

[0674]

[0675] The product weight was 5.6 g.

[0676] 1 H-NMR

[0677] δ0.1-0.2(-Si-C H3 )30H

[0678] δ0.5(-(CH2)7C H2 -Si(O-Si(CH3)2-)3)2H

[0679] δ0.7-0.8(-C6H4-Si-CH2-)4H

[0680] δ1.2-1.5(-(C H2 )7-,-OCH2C H3 ,-Si-CH2(C H2 )6CH2-Si-)29H

[0681] δ1.6(-OOC-CH2C H2 (CH2)7CH2-Si-)2H

[0682] δ2.3(-OOC-C H2 -)2H

[0683] δ4.1(-OC H2 CH3)2H

[0684] δ4.7(-Si-H)3H

[0685] δ7.5(-Si-C6 H4 -Si-)4H

[0686] The above-obtained

[0687] [Chemistry 130]

[0688]

[0689] The compound represented by 3.0g (3.9×10 -3 mol) was heated to 80°C. Then, 2.5×10 -3 g (calculated as Pt single substance, containing 7.5×10 -8 mol), then 2.6 g (1.6 × 10 -2 mol), heated and stirred for 3 hours. Then, the solvent and unreacted products were removed under reduced pressure to obtain the following formula (J):

[0690] [Chemistry 131]

[0691]

[0692] The expressed product (Compound 4) was 4.2 g.

[0693] 1 H-NMR

[0694] δ0.1-0.2(-Si-C H3 )3OH

[0695] δ0.5(-(CH2)7C H2 -Si(O-Si(CH3)2-)3)2H

[0696] δ0.6-0.8(-C6H4-Si-C H2 -,-SiCH2CH2C H2 -Si(OCH3)3, -SiC H2 CH2CH2-Si(OCH3)3)16H

[0697] δ1.2-1.4(-(C H2 )7-,-OCH2C H3 ,-Si-CH2(C H2 )6CH2-Si-)29H

[0698] δ1.5(-SiCH2C H2 CH2-Si(OCH3)3)6H

[0699] δ1.6(-OOC-CH2C H2 (CH2)7CH2-Si-)2H

[0700] δ2.3(-OOC-C H2 -)2H

[0701] δ3.5(-SiCH2CH2CH2-Si(OC H3 )3)27H

[0702] δ4.1(-OC H2 CH3)2H

[0703] δ7.5(-Si-C6 H4 -Si-)4H

[0704] [Synthesis example 5]

[0705] 31.6 g (2.35 × 10 -1 mol) was heated to 80°C. Then, 1.0×10 -2 g (calculated as Pt single substance, containing 3.0×10 -7 mol), 10.0 g (4.71 × 10 -2 mol), heated and stirred for 1 hour. Then, the solvent and unreacted products were removed under reduced pressure to obtain the following formula (K):

[0706] [Chemistry 132]

[0707]

[0708] The product weight was 16.4 g.

[0709] 1 H-NMR

[0710] δ0.2-0.4(-Si-C H3 )12H

[0711] δ0.7(-(CH2)7C H2 -Si-)2H

[0712] δ1.2-1.5(-(C H2 )7-,-OCH2C H3 )17H

[0713] δ1.6(-OOC-CH2C H2 (CH2)7CH2-Si-)2H

[0714] δ2.3(-OOC-C H2 -)2H

[0715] δ4.1(-OC H2 CH3)2H

[0716] δ4.4(-Si-H)1H

[0717] The above-obtained

[0718] [Chemistry 133]

[0719]

[0720] The compound represented by 10.0 g (2.88 × 10 -2 mol) was heated to 80°C. Then, 1.0×10 -2 g (calculated as Pt single substance, containing 3.0×10 -7 mol), 9.4 g (4.04 × 10 -2 mol), heated and stirred for 3 hours. Then, the solvent and unreacted products were removed under reduced pressure to obtain the following formula (L):

[0721] [Chemistry 134]

[0722]

[0723] The represented compound was 15.1 g.

[0724] 1H-NMR

[0725] δ0.2-0.3(-Si-C H3 )12H

[0726] δ0.7(-(CH2)7C H2 -Si-, -SiC H2 (CH2)6CH2-Si(OCH3)3)4H

[0727] δ0.8(-SiCH2(CH2)6C H2 -Si(OCH3)3)2H

[0728] δ1.2-1.4(-(C H2 )7-,-SiCH2(C H2 )6CH2-Si(OCH3)3,-OCH2C H3 )29H

[0729] δ1.6(-OOC-CH2C H2 (CH2)7CH2-Si-)2H

[0730] δ2.3(-OOC-C H2 -)2H

[0731] δ3.5(-SiCH2(CH2)6CH2-Si(OC H3 )3)9H

[0732] δ4.1(-OC H2 CH3)2H

[0733] 5.1 g (3.8 × 10 -2 mol), 4.1 g (4.9 × 10 -2 mol) and 5.0 g of 1,4-bis(trifluoromethyl)benzene were cooled to 0°C. Then, the above-synthesized product of the following formula (L) was added dropwise.

[0734] [Chemistry 135]

[0735]

[0736] The compound represented by 10.0 g (1.7 × 10 -2 mol), and aged at 0°C for 6 hours. Then, the lower layer was recovered by liquid separation operation, and the solvent and unreacted products were removed by reduced pressure distillation to obtain the following formula (M):

[0737] [Chemistry 136]

[0738]

[0739] The product represented was 8.6 g.

[0740] 1 H-NMR

[0741] δ0.1-0.2(-Si-C H3 )30H

[0742] δ0.5-0.6(-O-Si(CH3)2-C H2 -)6H

[0743] δ1.2-1.5(-(C H2 )7-,-OCH2C H3 ,-Si-CH2(C H2 )6CH2-Si-)29H

[0744] δ1.6(-OOC-CH2C H2 (CH2)7CH2-Si-)2H

[0745] δ2.3(-OOC-C H2 -)2H

[0746] δ4.1(-OC H2 CH3)2H

[0747] δ4.7(-Si-H)3H

[0748] The above obtained compound of the following formula (M) is placed in a reaction container.

[0749] [Chemistry 137]

[0750]

[0751] The compound represented by 5.0g (7.0×10 -3 mol) was heated to 80°C. Then, 5.0×10 -3 g (calculated as Pt single substance, containing 1.5×10 -7 mol), then 4.6 g (2.8 × 10 -2 mol), heated and stirred for 3 hours. Then, the solvent and unreacted products were removed under reduced pressure to obtain the following formula (N):

[0752] [Chemistry 138]

[0753]

[0754] The product (Compound 5) was 6.7 g.

[0755] 1 H-NMR

[0756] δ0.1-0.22(-Si-C H3 )30H

[0757] δ0.5-0.7(-O-Si(CH3)2-C H2 , -SiCH2CH2C H2 -Si(OCH3)3, -SiC H2 CH2CH2-Si(OCH3)3)18H

[0758] δ1.2-1.4(-(C H2 )7-,-OCH2C H3 ,-Si-CH2(C H2 )6CH2-Si-)29H

[0759] δ1.5(-SiCH2C H2 CH2-Si(OCH3)3)6H

[0760] δ1.6(-OOC-CH2C H2 (CH2)7CH2-Si-)2H

[0761] δ2.3(-OOC-C H2 -)2H

[0762] δ3.5(-SiCH2CH2CH2-Si(OC H3 )3)27H

[0763] δ4.1(-OC H2 CH3)2H

[0764] [Synthesis example 6]

[0765] The compound represented by the following formula (D) obtained in Synthesis Example 2 was placed in a reaction container.

[0766] [Chemistry 139]

[0767]

[0768] The compound represented by 5.0g (1.1×10 -2 mol) was heated to 80°C. Then, 5.0×10 -3 g (calculated as Pt single substance, containing 1.5×10 -7 mol), 10.0 g (4.3 × 10 -2mol), heated and stirred for 3 hours. Then, the solvent and unreacted products were removed under reduced pressure to obtain the following formula (0):

[0769] [Chemistry 140]

[0770]

[0771] The expressed product (Compound 6) was 11.0 g.

[0772] 1 H-NMR

[0773] δ0.1-0.2(-Si-C H3 )18H

[0774] δ0.5(-(CH2)7C H2 -Si(O-Si(CH3)2-)3)2H

[0775] δ0.6-0.8(-SiCH2(C H2 )6C H2 -Si(OCH3)3, -SiC H2 (C H2 )6CH2-Si(OCH3)3)12H

[0776] δ1.2-1.4(-(C H2 )7-,-OCH2C H3 )17H

[0777] δ1.5(-SiCH2(C H2 )6CH2-Si(OCH3)3)36H

[0778] δ1.6(-OOC-CH2C H2 (CH2)7CH2-Si-)2H

[0779] δ2.3(-OOC-C H2 -)2H

[0780] δ3.5(-SiCH2CH2CH2-Si(OC H3 )3)27H

[0781] δ4.1(-OC H2 CH3)2H

[0782] [Synthesis Example 7]

[0783] The compound of the following formula (F) obtained in Synthesis Example 3 was placed in a reaction container.

[0784] [Chemistry 141]

[0785]

[0786] The compound represented by 10.0 g (1.4 × 10 -2 mol) was heated to 80°C. Then, 1.0×10 chloroplatinic acid / vinylsiloxane complex toluene solution was added. -2 g (calculated as Pt single substance, containing 3.0×10 -7 mol), 13.4 g (5.8 × 10 -2 mol), heated and stirred for 3 hours. Then, the solvent and unreacted products were removed under reduced pressure to obtain the following formula (P):

[0787] [Chemistry 142]

[0788]

[0789] The expressed product (Compound 7) was 15.4 g.

[0790] 1 H-NMR

[0791] δ0.1-0.2(-Si-C H3 )30H

[0792] δ0.5(-(CH2)7C H2 -Si(O-Si(CH3)2-)3)2H

[0793] δ0.6-0.8(-C6H4-Si-C H2 -,-SiCH2(C H2 )6C H2 -Si(OCH3)3, -SiC H 2(C H2 )6CH2-Si(OCH3)3)16H

[0794] δ1.2-1.4(-(C H2 )7--OCH2C H3 )17H

[0795] δ1.5(-SiCH2(C H2 )6CH2-Si(OCH3)3)36H

[0796] δ1.6(-OOC-CH2C H2 (CH2)7CH2-Si-)2H

[0797] δ2.3(-OOC-C H2 -)2H

[0798] δ3.5(-SiCH2CH2CH2-Si(OC H3 )3)27H

[0799] δ4.1(-OC H2 CH3)2H

[0800] δ7.5(-Si-C6 H4 -Si-)4H

[0801] [Synthesis example 8]

[0802] The compound of the following formula (I) obtained in Synthesis Example 4 was placed in a reaction container.

[0803] [Chemistry 143]

[0804]

[0805] The compound represented was 1.8 g (2.3 × 10 -3 mol) was heated to 80°C. Then, 2.0×10 -3 g (calculated as Pt single substance, containing 6.0×10 -8 mol), 2.3 g (9.8 × 10 -3 mol), heated and stirred for 3 hours. Then, the solvent and unreacted products were removed under reduced pressure to obtain the following formula (Q):

[0806] [Chemistry 144]

[0807]

[0808] The obtained product (Compound 8) was 2.7 g.

[0809] 1 H-NMR

[0810] δ0.1-0.2(-Si-C H3 )30H

[0811] δ0.5(-(CH2)7C H2 -Si(O-Si(CH3)2-)3)2H

[0812] δ0.6-0.8(-C6H4-Si-C H2 -,-SiCH2(C H2 )6C H2 -Si(OCH3)3, -SiC H2 (C H2 )6CH2-Si(OCH3)3)16H

[0813] δ1.2-1.4(-(C H2 )7-,-OCH2CH3)17H

[0814] δ1.5(-SiCH2(C H2 )6CH2-Si(OCH3)3)36H

[0815] δ1.6(-OOC-CH2C H2 (CH2)7CH2-Si-)2H

[0816] δ2.3(-OOC-C H2 -)2H

[0817] δ3.5(-SiCH2CH2CH2-Si(OC H3 )3)27H

[0818] δ4.1(-OC H2 CH3)2H

[0819] δ7.5(-Si-C6 H4 -Si-)4H

[0820] [Synthesis Example 9]

[0821] The compound of the following formula (M) obtained in Synthesis Example 5 was placed in a reaction container.

[0822] [Chemistry 145]

[0823]

[0824] The compound represented by 5.0g (7.0×10 -3 mol) was heated to 80°C. Then, 5.0×10 chloroplatinic acid / vinylsiloxane complex toluene solution was added. -3 g (calculated as Pt single substance, containing 1.5×10 -7 mol), 6.5 g (2.8 × 10 -2 mol), heated and stirred for 3 hours. Then, the solvent and unreacted products were removed under reduced pressure to obtain the following formula (R):

[0825] [Chemistry 146]

[0826]

[0827] The obtained product (Compound 9) was 7.6 g.

[0828] 1 H-NMR

[0829] δ0.1-0.2(-Si-CH3 )3OH

[0830] δ0.5-0.7(-O-Si(CH3)2-C H2 -,-SiCH2(C H2 )6C H2 -Si(OCH3)3, -SiC H2 (C H2 )6CH2-Si(OCH3)3)18H

[0831] δ1.2-1.4(-(C H2 )7-,-OCH2C H3 )17H

[0832] δ1.5(-SiCH2(C H2 )6CH2-Si(OCH3)3)36H

[0833] δ1.6(-OOC-CH2C H2 (CH2)7CH2-Si-)2H

[0834] δ2.3(-OOC-C H2 -)2H

[0835] δ3.5(-SiCH2CH2CH2-Si(OC H3 )3)27H

[0836] δ4.1(-OC H2 CH3)2H

[0837] [Synthesis Example 10]

[0838] 40.6 g (2.09 × 10 -1 mol) was heated to 80°C. Then, 1.0×10 -2 g (calculated as Pt single substance, containing 3.0×10 -7 mol), and then the following formula (S) was added dropwise over 3 hours.

[0839] [Chemistry 147]

[0840]

[0841] The compound represented by 10.0 g (4.18 × 10 -2 mol), heated and stirred for 6 hours. Then, the solvent and unreacted products were removed under reduced pressure to obtain the following formula (T):

[0842] [Chemistry 148]

[0843]

[0844] The product represented was 17.1 g.

[0845] 1 H-NMR

[0846] δ0.2-0.4(-Si-C H3 )12H

[0847] δ0.7(-(CH2)7C H2 -Si-)2H

[0848] δ1.0-1.2(-N(CH2C H3 )2)6H

[0849] δ1.2-1.5(-(C H2 )7-)14H

[0850] δ1.6(-NOC-CH2C H2 (CH2)7CH2-Si-)2H

[0851] δ2.3(-NOC-C H2 -)2H

[0852] δ3.2-3.4(-N(C H2 CH3)2)4H

[0853] δ4.4(-Si-H)1H

[0854] δ7.5(-Si-C6 H4 -Si-)4 H

[0855] The above-obtained compound of the following formula (T) is placed in a reaction container.

[0856] [Chemistry 149]

[0857]

[0858] The compound represented by 10.0 g (2.31 × 10 -2 mol) was heated to 80°C. Then, 1.0×10 chloroplatinic acid / vinylsiloxane complex toluene solution was added. -2 g (calculated as Pt single substance, containing 3.0×10 -7 mol), 7.5 g (3.23 × 10 -2 mol), heated and stirred for 6 hours. Then, the solvent and unreacted products were distilled off under reduced pressure to obtain the following formula (U):

[0859] [Chemistry 150]

[0860]

[0861] The expressed compound was 12.6 g.

[0862] 1 H-NMR

[0863] δ0.2-0.3(-Si-C H3 )12H

[0864] δ0.7(-(CH2)7C H2 -Si-, -SiC H2 CH2CH2-Si(OCH3)3)4H

[0865] δ0.8(-SiCH2CH2C H2 -Si(OCH3)3)2H

[0866] δ1.0-1.2(-N(CH2CH3)2)6H

[0867] δ1.2-1.4(-(C H2 )7-)14H

[0868] δ1.5(-SiCH2C H2 CH2-Si(OCH3)3)2H

[0869] δ1.6(-NOC-CH2C H2 (CH2)7CH2-Si-)2H

[0870] δ2.3(-NOC-C H2 -)2H

[0871] δ3.2-3.4(-N(C H2 CH3)2)4H

[0872] δ3.5(-SiCH2CH2CH2-Si(OC H3 )3)9H

[0873] δ7.5(-Si-C6 H4 -Si-)4H

[0874] 4.5 g (3.4 × 10 -2 mol), 3.6 g of 12N hydrochloric acid solution (4.3 × 10 -2 mol) and 5.0 g of 1,4-bis(trifluoromethyl)benzene were cooled to 0°C. Then, the above-obtained

[0875] [Chemistry 151]

[0876]

[0877] The compound represented by 10.0 g (1.5 × 10 -2 mol), and aged at 0°C for 6 hours. Then, the lower layer was recovered by liquid separation operation, and the solvent and unreacted products were removed by reduced pressure distillation to obtain the following formula (V):

[0878] [Chemistry 152]

[0879]

[0880] The product weight was 8.6 g.

[0881] 1 H-NMR

[0882] δ0.1-0.2(-Si-C H3 )30H

[0883] δ0.5(-(CH2)7C H2 -Si(O-Si(CH3)2-)3)2H

[0884] δ0.7-0.8(-C6H4-Si-C H2 -)4H

[0885] δ1.0-1.2(-N(CH2C H3 )2)6H

[0886] δ1.2-1.5(-(C H2 )7-,-Si-CH2(C H2 )6CH2-Si-)26H

[0887] δ1.6(-NOC-CH2C H2 (CH2)7CH2-Si-)2H

[0888] δ2.3(-NOC-C H2 -)2H

[0889] δ3.2-3.4(-N(C H2 CH3)2)4H

[0890] δ4.7(-Si-H)3H

[0891] δ7.5(-Si-C6 H4 -Si-)4H

[0892] The above-obtained compound of the following formula (V) is placed in a reaction container.

[0893] [Chemistry 153]

[0894]

[0895] The compound represented by 5.0 g (6.3 × 10 -3 mol) was heated to 80°C. Then, 5.0×10 chloroplatinic acid / vinylsiloxane complex toluene solution was added. -3 g (calculated as Pt single substance, containing 1.5×10 -7 mol), 5.9 g (2.5 × 10 -2 mol), heated and stirred for 3 hours. Then, the solvent and unreacted products were removed under reduced pressure to obtain the following formula (W):

[0896] [Chemistry 154]

[0897]

[0898] The obtained product (Compound 10) was 8.1 g.

[0899] 1 H-NMR

[0900] δ0.1-0.2(-Si-C H3 )30H

[0901] δ0.5(-(CH2)7C H2 -Si(O-Si(CH3)2-)3)2H

[0902] δ0.6-0.8(-C6H4-Si-C H2 -,-SiCH2CH2C H2 -Si(OCH3)3, -SiC H2 CH2CH2-Si(OCH3)3)16H

[0903] δ1.0-1.2(-N(CH2C H3 )2)6H

[0904] δ1.2-1.4(-(C H2 )7-,-Si-CH2(C H2 )6CH2-Si-)26H

[0905] δ1.5(-SiCH2C H2 CH2-Si(OCH3)3)6H

[0906] δ1.6(-NOC-CH2C H 2(CH2)7CH2-Si-)2H

[0907] δ2.3(-NOC-C H2 -)2H

[0908] δ3.2-3.4(-N(C H2 CH3)2)4H

[0909] δ3.5(-SiCH2CH2CH2-Si(OC H3 )3)27H

[0910] δ7.5(-Si-C6 H4 -Si-)4H

[0911] As comparative compounds, the following compounds were used.

[0912] Compound 11 represented by the following formula (X)

[0913] [Chemistry 155]

[0914]

[0915] Preparation of surface treatment agent and formation of cured film

[0916] [Examples 1 to 10]

[0917] The hydrolyzable organosilane or organosiloxane compounds 1 to 10 containing lipophilic groups represented by formulas (B), (E), (G), (J), (N), (O), (P), (Q), (R), and (W) obtained in Synthesis Examples 1 to 10 were dissolved in propylene glycol monomethyl ether at a concentration of 0.1 mass %, and acetic acid was further dissolved in a concentration of 0.1 mass %, thereby preparing a surface treatment agent. Then, the surface treatment agent was dip-coated on Gorilla glass manufactured by Corning Incorporated and cured at 120° C. for 30 minutes to prepare cured films having the film thicknesses shown in Table 1.

[0918] [Comparative Example 1]

[0919] The hydrolyzable organosilane compound 11 represented by the formula (X) was dissolved in Novec 7200 (3M Co., ethyl perfluorobutyl ether) at a concentration of 0.1 mass % to prepare a surface treatment agent. The surface treatment agent was then dip-coated on Gorilla glass manufactured by Corning Incorporated and cured at 120° C. for 30 minutes to produce a cured film having the thickness described in Table 1.

[0920] [Comparative Example 2]

[0921] As Comparative Example 2 (blank), Gorilla Glass manufactured by Corning Incorporated was used without any coating.

[0922] [Evaluation of film thickness]

[0923] The film thickness of the glass formed with the cured film prepared above was measured using a transmission electron microscope H-9500 (manufactured by Hitachi High-Technologies Corporation). The sample was sliced ​​by the FIB method, and the cross section was observed at an accelerating voltage of 200 kV. The results are shown in Table 1.

[0924] [Evaluation of haze]

[0925] The glass having the cured film formed thereon was immersed in oleic acid for 1 minute, and then pulled up, and the haze (haze) was measured using a haze meter NDH5000 (manufactured by Nippon Denshoku Industries Co., Ltd.).

[0926] [Evaluation of lipophilicity]

[0927] The contact angle (lipophilicity) of the cured film on the glass formed with the cured film was measured using a contact angle meter Drop Master (manufactured by Kyowa Interface Science Co., Ltd.) for oleic acid (droplet: 2 μl, temperature: 25°C, humidity (RH): 40%). The results (oleic acid contact angle) are shown in Table 1.

[0928] [Table 1]

[0929]

[0930] All Examples 1 to 10 had low haze values ​​after oleic acid immersion, confirming high transparency. On the other hand, Comparative Example 1 using Compound 11 as an oil-repellent surface treatment agent and Comparative Example 2 without surface treatment had high haze values, indicating blurring.

Claims

1. An optical component, wherein: A surface treatment agent layer having a room temperature curing film or a heat curing film formed by surface treatment with a surface treatment agent and having a film thickness of 2 nm or more and less than 5 nm, wherein the oleic acid contact angle of the surface treatment agent layer is 20° or less, The surface treatment agent comprises an organosilane or organosiloxane compound containing a lipophilic group and a hydrolyzable group, but does not include a surface treatment agent containing a coating composition comprising: The hydrolyzable group is a group selected from an alkoxy group having 1 to 10 carbon atoms, an alkoxy-substituted alkoxy group having 2 to 10 carbon atoms, an acyloxy group having 1 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, a halogen atom, an oxime group, and a cyanate group. The coating composition contains (A) one or more organic silane or siloxane compounds represented by the following general formula (1') and their partial (hydrolyzed) condensates and (B) one or more silane or siloxane compounds represented by the following general formula (2') and their partial (hydrolyzed) condensates in a mass ratio of 50:50 to 90:10, wherein the total of the components (A) and (B) is 100. In the formula, A is -C(=O)OR 1 、-C(=O)NR 1 2. -C(=O)SR 1 and -P(=O)(OR 1 )2, R 1 is a hydrogen atom, an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, or an aralkyl group having 7 to 30 carbon atoms, Y is independently a divalent organic group which may have an organopolysiloxane residue, R is independently an alkyl group having 1 to 4 carbon atoms or a phenyl group, X is independently a hydroxyl group or a hydrolyzable group, and n is an integer of 1 to 3, In the formula, Rf is a perfluoroalkylene group or a divalent perfluoropolyether group, and Y, R, X, and n are the same as described above. 2 . The optical member according to claim 1 , wherein the haze of the optical member after being immersed in oleic acid for 1 minute and then pulled up is 1.5% or less.

3. The optical component according to claim 1, wherein The organosilane compound is an organosilane compound represented by the following general formula (1): In the formula, A is -C(=O)OR 1 、-C(=O)NR 1 2. -C(=O)SR 1 and -P(=O)(OR 1 )2, R 1 is a hydrogen atom, an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, or an aralkyl group having 7 to 30 carbon atoms, Y is independently a divalent organic group, R is independently an alkyl group having 1 to 4 carbon atoms or a phenyl group, X is independently a group selected from an alkoxy group having 1 to 10 carbon atoms, an alkoxy-substituted alkoxy group having 2 to 10 carbon atoms, an acyloxy group having 1 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, a halogen atom, an oxime group, and a cyanate group, and n is an integer of 1 to 3.

4. The optical component according to claim 3, wherein In the general formula (1), Y is an alkylene group having 2 to 30 carbon atoms, which may include a divalent group selected from -O-, -S-, -NR-, -C(=O)-, -C(=O)O-, -C(=O)NR-, -OC(=O)NR-, a silylene group, a silylene group, and a linear, branched or cyclic divalent organic (poly)siloxane residue having 2 to 10 silicon atoms, and may also include an arylene group having 6 to 20 carbon atoms; Here, R is an alkyl group having 1 to 4 carbon atoms or a phenyl group.

5. The optical component according to claim 3, wherein The organosilane compound is an organosilane compound represented by the following general formula (2): In the formula, R 2 is an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an aralkyl group having 7 to 20 carbon atoms, m is each independently an integer of 2 to 20, and X is independently a group selected from an alkoxy group having 1 to 10 carbon atoms, an alkoxy-substituted alkoxy group having 2 to 10 carbon atoms, an acyloxy group having 1 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, a halogen atom, an oxime group, and a cyanate group.

6. The optical component according to claim 1, wherein The organosiloxane compound is an organosiloxane compound represented by the following general formula (3): In the formula, A' is -CH3, -C(=O)OR 1 、-C(=O)NR 1 2. -C(=O)SR 1 and -P(=O)(OR 1 )2, R 1 is a hydrogen atom, an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, or an aralkyl group having 7 to 30 carbon atoms, Y' is independently a divalent organic group, W is independently an alkyl group having 1 to 4 carbon atoms, a phenyl group, a hydroxyl group, or a hydrolyzable group, R is independently an alkyl group having 1 to 4 carbon atoms or a phenyl group, X is independently a group selected from an alkoxy group having 1 to 10 carbon atoms, an alkoxy-substituted alkoxy group having 2 to 10 carbon atoms, an acyloxy group having 1 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, a halogen atom, an oxime group, and a cyanate group, n is an integer of 1 to 3, and q is an integer of 1 to 3.

7. The optical component according to claim 6, wherein In the general formula (3), Y' is an alkylene group having 2 to 30 carbon atoms, which may include a divalent group selected from -O-, -S-, -NR-, -C(=O)-, -C(=O)O-, -C(=O)NR-, -OC(=O)NR-, silylene groups, silylene groups, and divalent organic (poly)siloxane residues having 2 to 10 silicon atoms in a linear, branched or cyclic form, and may also include an arylene group having 6 to 20 carbon atoms; Here, R is an alkyl group having 1 to 4 carbon atoms or a phenyl group.

8. The optical component according to claim 6, wherein The organosiloxane compound is an organosiloxane compound represented by the following general formula (4): In the formula, R 3 is an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an aralkyl group having 7 to 20 carbon atoms, Q is a single bond, or a divalent group selected from a silylene group, a silylene group, and a linear, branched, or cyclic divalent organic (poly)siloxane residue having 2 to 10 silicon atoms, m' is each independently an integer of 1 to 20, m" is an integer of 2 to 20, and X is independently a group selected from an alkoxy group having 1 to 10 carbon atoms, an alkoxy-substituted alkoxy group having 2 to 10 carbon atoms, an acyloxy group having 1 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, a halogen atom, an oxime group, and a cyanate group.

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