Hydrocarbon terminal group-containing compound, surface treatment agent, and article

Abstract

A hydrocarbon terminal group-containing compound represented by formula (1) has excellent solubility in various solvents. When the hydrocarbon terminal group-containing compound is used as a surface treatment agent for a non-fluorine-based material, intermolecular interaction and molecular chain mobility are improved. A surface treatment agent containing the compound can form a cured coating film having excellent water repellency and wear resistance, particularly excellent steel wool wear resistance. (R represents a C1-10 monovalent hydrocarbon group, Z represents a divalent linking functional group containing at least one selected from O, N, S, and Si, Y represents a C1-30 divalent hydrocarbon group, W represents a single bond, C, Si, N, or a trivalent to pentavalent organic group, A represents a monovalent reactive group, k1 represents 1-3, k2 represents 1-4, and k3 and k4 represent 0 or 1.)

Description

Hydrocarbon-terminated compounds, surface treatment agents, and articles

[0001] The present invention relates to hydrocarbon-terminated compound materials, and more particularly to non-fluorinated hydrocarbon-terminated compound materials that form a coating with excellent solvent solubility, water repellency, and abrasion resistance, a surface treatment agent containing the compound, and an article surface-treated with the surface treatment agent.

[0002] In recent years, the use of touch panels in displays such as smartphones and in-car displays has accelerated. However, because touch panels have exposed screens, they are frequently in direct contact with fingers and cheeks, making them prone to dirt and grime. Therefore, there is a growing demand for technologies that make the display surface less prone to fingerprints and easier to clean, in order to improve appearance and visibility. The development of materials that can meet these demands is highly desirable. In particular, since the surface of touch panel displays is prone to fingerprint smudges, there is a desire to provide a water- and oil-repellent layer. However, conventional water- and oil-repellent layers have the problem that while they have high water- and oil-repellent properties and are excellent at wiping away dirt, they do not have sufficient abrasion resistance.

[0003] Generally, fluoropolyether group-containing compounds have very low surface free energy, resulting in properties such as water and oil repellency, chemical resistance, lubricity, mold release, and antifouling. These properties are utilized industrially in a wide range of applications, including water, oil, and stain repellents for paper and textiles, lubricants for magnetic recording media, oil inhibitors and mold release agents for precision equipment, cosmetics, and protective films. However, these properties also mean non-stickiness and poor adhesion to other substrates; while they can be applied to substrate surfaces, achieving a strong bond between the film and the substrate is difficult.

[0004] Silane coupling agents are well-known for bonding organic compounds to substrate surfaces such as glass and cloth, and are widely used as coating agents for various substrate surfaces. A silane coupling agent has an organic functional group and a reactive silyl group (generally a hydrolyzable silyl group such as an alkoxysilyl group) in one molecule. The hydrolyzable silyl group undergoes a self-condensation reaction with moisture in the air to form a film. This film becomes a strong and durable coating because the hydrolyzable silyl group chemically and physically bonds with the surface of glass, metal, etc.

[0005] Therefore, compositions have been disclosed that use a fluoropolyether group-containing polymer obtained by introducing a hydrolyzable silyl group into a fluoropolyether group-containing compound, which can easily adhere to the substrate surface and form a coating on the substrate surface that has water-repellent and oil-repellent properties, chemical resistance, lubricity, mold release properties, and antifouling properties (Patent Documents 1 to 6: Japanese Patent Publication No. 2008-534696, Japanese Patent Publication No. 2008-537557, Japanese Unexamined Patent Publication No. 2012-072272, Japanese Unexamined Patent Publication No. 2012-157856, Japanese Unexamined Patent Publication No. 2013-136833, Japanese Unexamined Patent Publication No. 2015-199906).

[0006] However, fluorine-based compounds have the characteristic of being difficult to decompose in nature and tend to accumulate in the environment, which has led to a demand for the development of surface treatment agents for non-fluorine-based materials.

[0007] Therefore, International Publication No. 2019 / 82583 (Patent Document 7) proposes a surface treatment agent that does not use fluorine groups. However, there is a growing demand for coatings formed by such surface treatment agents that can withstand harsher operating environments, and improved wear resistance is desired.

[0008] Furthermore, compounds with linear alkyl groups that generally have a large number of carbon atoms sometimes exhibit poor solubility in certain solvents, such as alcohols.

[0009] Japanese Patent Publication No. 2008-534696, Japanese Patent Publication No. 2008-537557, Japanese Unexamined Patent Publication No. 2012-072272, Japanese Unexamined Patent Publication No. 2012-157856, Japanese Unexamined Patent Publication No. 2013-136833, Japanese Unexamined Patent Publication No. 2015-199906, International Publication No. 2019 / 82583

[0010] The present invention has been made in view of the above circumstances, and aims to provide a non-fluorine-based (i.e., one that does not contain fluorine atoms in its molecule) hydrocarbon-terminated compound that exhibits excellent solubility in various solvents, particularly polar solvents, and can form a cured film with excellent water repellency and abrasion resistance, as well as a non-fluorine-based surface treatment agent containing the compound, and an article surface-treated with the surface treatment agent.

[0011] The inventors diligently studied to solve the above objective and found that compounds having alkyl groups with a large number of carbon atoms may have poor solubility in polar solvents such as alcohols because the polarity of the long alkyl groups is low. Furthermore, intermolecular interactions, including van der Waals forces, act between the long alkyl groups, which tends to worsen solubility. Therefore, the inventors conducted further studies and found that a hydrocarbon terminal group-containing compound represented by the general formula (1) described later, which has a monovalent hydrocarbon group having 1 to 10 carbon atoms and 1 to 4 reactive groups at the end of the molecular chain, and has 1 to 3 linking functional groups in the linking group (molecular chain) between the monovalent hydrocarbon group and the 1 to 4 reactive groups, exhibits excellent solubility in various solvents by reducing the number of carbon atoms in the monovalent hydrocarbon group from the molecular tip to the first linking functional group to 10 or less. Furthermore, we have discovered that when a hydrocarbon-terminated compound represented by the general formula (1) is used as a surface treatment agent for the above-mentioned non-fluorinated material, intermolecular interactions and molecular chain mobility are improved, and the surface treatment agent containing the compound can form a hardened film with excellent water repellency, abrasion resistance, and especially resistance to steel wool abrasion, thus leading to the present invention.

[0012] Accordingly, the present invention provides the following hydrocarbon terminal group-containing compounds, surface treatment agents and articles. [1] The following general formula (1) A hydrocarbon terminal group-containing compound represented by the formula (wherein R is a monovalent hydrocarbon group having 1 to 10 carbon atoms, Z is a divalent linking functional group containing at least one independently selected from an oxygen atom, a nitrogen atom, a sulfur atom, and a silicon atom, Y is independently a divalent hydrocarbon group having 1 to 30 carbon atoms, W is a single bond, a carbon atom, a silicon atom, a nitrogen atom, or a 3 to 5 valent organic group, A is a monovalent reactive group, k1 is an integer from 1 to 3, k2 is an integer from 1 to 4, k3 is 0 or 1, and k4 is 0 or 1.) [2] In the above formula (1), A is a cyclic ether group, the following general formula (2) (In the formula, R 1 ) is an alkyl group or phenyl group having 1 to 4 carbon atoms independently, X is an alkyl group or hydrolyzable group independently, and n is an integer from 1 to 3. ) A hydroxyl group-containing silyl group or hydrolyzable silyl group represented by the following general formula (3) A hydrocarbon terminal group-containing compound according to [1], wherein the silazane group is represented by (wherein n'' is a number from 0 to 3, and n' is (3-n'') / 2). [3] A hydrocarbon terminal group-containing compound according to [2], wherein in formula (2) above, X is selected from the group consisting of a hydroxyl group, an alkoxy group having 1 to 10 carbon atoms, an alkoxyalkoxy 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 group, and a dialkylamino group having 2 to 10 carbon atoms. [4] A hydrocarbon terminal group-containing compound according to any one of [1] to [3] above, wherein in formula (1) above, R is a monovalent hydrocarbon group having 3 to 10 carbon atoms, which may be linear, branched, cyclic, or a combination thereof. [5] A hydrocarbon terminal group-containing compound according to any one of [1] to [4], wherein Z is independently an ether group, carbonyl (ketone) group, ester group, carbonate group, thioether group, sulfinyl group, sulfonyl group, thioester group, thiocarbonate group, thiocarbamate group, amino group, amide group, carbamate group, urea group, divalent nitrogen-containing heterocyclic group, diorganosilylene group, and a divalent organopolysiloxane residue having 2 to 10 silicon atoms in a linear chain or 3 to 10 silicon atoms in a branched or cyclic configuration. [6] A hydrocarbon terminal group-containing compound according to any one of [1] to [4], wherein Y is independently the following general formula (4) (In the formula, R 2 R is an independent monovalent hydrocarbon group having 1 to 10 carbon atoms. 3 is a divalent cyclic hydrocarbon group having 3 to 9 carbon atoms, which may independently have substituents. a is an integer from 0 to 30, b is an integer from 0 to 15, c is an integer from 0 to 10, and d is an integer from 0 to 6, and the sum of a, b, c, and d is an integer such that the sum of carbon atoms in formula (4) is 1 to 30. Each repeating unit shown in the parentheses with a, b, c, and d may be randomly bonded.) A hydrocarbon terminal group-containing compound according to any one of [1] to [5], which is a group represented by ). [7] In the above formula (1), W is a single bond, a carbon atom, a silicon atom, a nitrogen atom, a trivalent or tetravalent cyclic hydrocarbon group having 6 to 8 carbon atoms, -SiR 8 = (R 8is a trivalent group represented by a hydroxyl group, an alkyl group having 1 to 3 carbon atoms, or an alkoxy group having 1 to 3 carbon atoms), -CR 9 = (R 9 is a trivalent group represented by a hydrogen atom, a hydroxyl group, or an alkyl group having 1 to 3 carbon atoms), a linear organopolysiloxane residue having 2 to 10 silicon atoms or a branched or cyclic trivalent to pentavalent organopolysiloxane residue having 3 to 10 silicon atoms, a trivalent amide group, a trivalent carbamate group, a trivalent or tetravalent urea group, and a trivalent or tetravalent nitrogen-containing heterocyclic group-containing group, which is a trivalent to pentavalent group selected from the group consisting of [1] to [6]. [8] In the above formula (1), k1 is 1 and R is represented by the following general formula (5) (wherein R 4 is a methyl group, a cyclic alkyl group or a phenyl group. R 3 is a divalent cyclic hydrocarbon group having 3 to 9 carbon atoms, which may independently have a substituent. y is an integer of 0 or more, h is an integer of 0 to 3, and the sum of y and h is an integer such that the total number of carbon atoms in formula ( (5) is 10 or less. Each repeating unit shown in the parentheses to which y and h are attached may be randomly bonded.). It is a hydrocarbon terminal group-containing compound according to any one of [1] to [7]. [9] In the above formula (1), k1 is 2 or 3.

[10] A surface treatment agent containing the hydrocarbon terminal group-containing compound according to any one of [1] to [9].

[11] An article surface-treated with the surface treatment agent according to

[10] .

[0013] The hydrocarbon terminal group-containing compound of the present invention is excellent in solubility in various solvents, and an article surface-treated with a surface treatment agent containing this hydrocarbon terminal group-containing compound is excellent in water repellency and abrasion resistance.

[0014] [Hydrocarbon terminal group-containing compound] The hydrocarbon terminal group-containing compound of the present invention is represented by the following general formula (1). (In the formula, R is a monovalent hydrocarbon group having 1 to 10 carbon atoms, Z is a divalent linking functional group independently comprising at least one atom selected from oxygen, nitrogen, sulfur, and silicon, Y is independently a divalent hydrocarbon group having 1 to 30 carbon atoms, W is a single bond, a carbon atom, a silicon atom, a nitrogen atom, or a 3 to 5 valent organic group, A is a monovalent reactive group, k1 is an integer from 1 to 3, k2 is an integer from 1 to 4, k3 is 0 or 1, and k4 is 0 or 1.)

[0015] The hydrocarbon-terminated compound of the present invention has a monovalent hydrocarbon group (hydrocarbon terminator, R in formula (1)) having 1 to 10 carbon atoms, preferably 3 to 10 carbon atoms, more preferably 8 to 10 carbon atoms, at the end of the molecular chain, and has 1 to 4 reactive groups (substrate-adhering groups, A in formula (1)) that exhibit substrate adhesion at the other end of the molecular chain, and the linking group connecting the hydrocarbon terminator and the substrate-adhering group is a divalent linking functional group (Z in formula (1)) containing at least one selected from an oxygen atom, a nitrogen atom, a sulfur atom, and a silicon atom (-(Z-Y in formula (1)) k1 -W(-{(Y-Z) k4 -Y} k3 -) k2 The compound is characterized by the following: The introduction of the linking functional group improves the molecular mobility of the compound, starting from the linking functional group. Furthermore, the orientation of the monovalent hydrocarbon group (hereinafter also referred to as hydrocarbon chain) is determined by the linking functional group, and due to intermolecular interactions between hydrocarbon chains and between linking functional groups, the hydrocarbon chains on the surface of the cured film tend to be oriented in one direction, so that the cured film of the surface treatment agent containing the compound has excellent water repellency and abrasion resistance. Moreover, because the number of carbon atoms in the hydrocarbon terminal group is 10 or less, the compound has excellent solubility in various solvents.

[0016] In formula (1) above, R is a monovalent hydrocarbon group having 1 to 10 carbon atoms, preferably 3 to 10 carbon atoms, and more preferably 8 to 10 carbon atoms. When R has 3 or more carbon atoms, it may be linear, branched, cyclic, or a combination thereof. Examples of R include the following: (In the formula, x is an integer between 0 and 9, preferably between 2 and 9, more preferably between 7 and 9, and y and y' are integers greater than or equal to 0 such that the sum of the number of carbon atoms in each structure is 10 or less.)

[0017] R is more preferably a monovalent hydrocarbon group represented by the following general formula (5), and particularly preferably an alkyl group. (In the formula, R 4 R is a methyl group, a cyclic alkyl group, or a phenyl group. 3 is a divalent cyclic hydrocarbon group having 3 to 9 carbon atoms, which may independently have substituents. y is an integer greater than or equal to 0, h is an integer from 0 to 3, preferably 0 or 1, more preferably 0, and the sum of y and h is an integer such that the total number of carbon atoms in formula (5) is 10 or less, preferably 3 to 10, more preferably 8 to 10. Each repeating unit shown in parentheses with y and h may be randomly bonded.

[0018] In the above formula (5), R 4 The group is a cyclic alkyl group such as a methyl group, cyclopentyl group, or cyclohexyl group, or a phenyl group, with a methyl group being preferred.

[0019] In the above formula (5), R 3 R is a divalent cyclic hydrocarbon group having 3 to 9 carbon atoms, which may independently have substituents. 3 Examples of divalent cyclic hydrocarbon groups represented by the formula are listed below. (In the formula, R 6 (These are alkyl groups having 1 to 3 carbon atoms, such as methyl and ethyl groups.)

[0020] In formula (1) above, Z is a linking group that, together with Y and W, links the hydrocarbon chain at the end of the molecular chain (R in formula (1)) to the reactive group (A in formula (1)). It is a divalent linking functional group containing at least one atom independently selected from oxygen, nitrogen, sulfur, and silicon, and is a characteristic component of the present invention. The divalent linking functional group containing at least one selected from oxygen, nitrogen, sulfur, and silicon atoms is preferably an ether group, carbonyl (ketone) group, ester group, carbonate group, thioether group, sulfinyl group, sulfonyl group, thioester group, thiocarbonate group, thiocarbamate group, amino group, amide group, carbamate group, urea group, divalent nitrogen-containing heterocyclic group (such as a divalent oxazole group, divalent imidazole group, or divalent triazole group), diorganosilylene group, or a linear or branched or cyclic divalent organopolysiloxane residue with 2 to 10 silicon atoms. Particularly preferred are ether groups, thioether groups, carbamate groups, and urea groups.

[0021] Examples of such Z include those shown below. In the structure below, the left-hand connector connects to R or Y, and the right-hand connector connects to Y. (In the formula, R 5 (E is an integer from 1 to 9.)

[0022] Here, R 5 R is independently a hydrogen atom or a monovalent hydrocarbon group having 1 to 10 carbon atoms. Examples of monovalent hydrocarbon groups having 1 to 10 carbon atoms include alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, neopentyl, cyclopentyl, hexyl, cyclohexyl, octyl, nonyl, and decyl groups; aryl groups such as phenyl, tolyl, xylyl, and naphthyl groups; aralkyl groups such as benzyl, phenylethyl, and phenylpropyl groups; and combinations thereof. 5If the number of carbon atoms is 3 or more, it may be linear, branched, cyclic, or a combination thereof. 5 Preferably, the elements are a hydrogen atom, a methyl group, or a phenyl group.

[0023] In formula (1) above, Y is a linking group that, together with Z and W, connects the hydrocarbon chain at the end of the molecular chain (R in formula (1)) to the reactive group (A in formula (1)), and is independently a divalent hydrocarbon group having 1 to 30 carbon atoms, preferably 1 to 20 carbon atoms, more preferably 1 to 11 carbon atoms, and even more preferably 1 to 4 carbon atoms. When Y has 3 or more carbon atoms, it may be linear, branched, cyclic, or a combination thereof. Examples of Y include the group represented by the following formula (4). (In the formula, R 2 R is an independent monovalent hydrocarbon group having 1 to 10 carbon atoms. 3 is a divalent cyclic hydrocarbon group having 3 to 9 carbon atoms, which may independently have substituents. a is an integer from 0 to 30, b is an integer from 0 to 15, c is an integer from 0 to 10, and d is an integer from 0 to 6, where the sum of a, b, c, and d is an integer such that the total number of carbon atoms in formula (4) is 1 to 30. The repeating units shown in the parentheses of a, b, c, and d may be randomly combined.

[0024] In the above formula (4), R 2 R is an independent monovalent hydrocarbon group having 1 to 10 carbon atoms. 2 If the carbon number is three or more, it may be linear, branched, cyclic, or a combination thereof. Specific examples of monovalent hydrocarbon groups include alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, neopentyl, hexyl, cyclohexyl, octyl, nonyl, and decyl groups; aryl groups such as phenyl, tolyl, xylyl, and naphthyl groups; aralkyl groups such as benzyl, phenylethyl, and phenylpropyl groups; and combinations thereof. 2 The following formula is preferred. (In the formula, g is an integer between 0 and 4.)

[0025] In the above formula (4), R3 R is a divalent cyclic hydrocarbon group having 3 to 9 carbon atoms, which may independently have substituents, and is the R in formula (5) described above. 3 It is the same as, and examples similar to those exemplified above can be given.

[0026] In formula (4) above, a is an integer from 0 to 30, preferably from 0 to 20; b is an integer from 0 to 15, preferably from 0 to 5; c is an integer from 0 to 10, preferably from 0 to 5; and d is an integer from 0 to 6, preferably 0 or 1. The sum of a, b, c, and d is an integer such that the total number of carbon atoms in formula (4) is 1 to 30, preferably from 1 to 10. Furthermore, the repeating units shown in the parentheses of a, b, c, and d may be combined randomly.

[0027] Examples of Y include those shown below. In the structure below, the left-hand connector connects to Z or W, and the right-hand connector connects to W, A, or Z. (In the formula, a1 is an integer between 1 and 30, a2 is an integer greater than or equal to 1, b1 is an integer between 1 and 15, c1 is an integer between 1 and 10, and g is an integer between 0 and 4, provided that the total number of carbon atoms in each structure is 30 or less.)

[0028] In formula (1) above, W is a single bond, a carbon atom, a silicon atom, a nitrogen atom, or a 3- to 5-valent organic group, and the 3- to 5-valent organic group is a 6- to 8 carbon atom trivalent or tetravalent cyclic hydrocarbon group, -SiR 8 = (R 8 (A trivalent group represented by a hydroxyl group, an alkyl group having 1 to 3 carbon atoms, or an alkoxy group having 1 to 3 carbon atoms), -CR 9 = (R 9Examples of trivalent groups include trivalent groups represented by a hydrogen atom, a hydroxyl group, or an alkyl group having 1 to 3 carbon atoms; linear trivalent to pentavalent organopolysiloxane residues having 2 to 10 silicon atoms, particularly 2 to 8 silicon atoms, or branched or cyclic trivalent to 3 to 10 silicon atoms, particularly 3 to 8 silicon atoms; trivalent amide groups; trivalent carbamate groups; trivalent or tetravalent urea groups; and trivalent or tetravalent nitrogen-containing heterocyclic groups (such as trivalent cyanurate groups, trivalent isocyanurate groups, and trivalent or tetravalent triazine ring-containing groups).

[0029] The organopolysiloxane residue may have an alkyl group such as a methyl group, ethyl group, propyl group, or butyl group, or a phenyl group, having 1 to 8 carbon atoms, more preferably 1 to 4 carbon atoms. The organopolysiloxane residue may also contain a sylalkylene structure in which two silicon atoms are linked by an alkylene group such as an ethylene group or a propylene group.

[0030] Examples of such W include, in addition to single bonds, those shown below. In the structure below, the leftmost bond connects to the Y enclosed in the brackets k1, and the other bond connects to the Y enclosed in the brackets k2. (In the formula, f is an integer between 2 and 4.)

[0031] In formula (1) above, A is a monovalent reactive group, preferably a functional group that has adhesion (bonding) reactivity to the surface of a substrate made of various materials such as paper, cloth, metal and its oxides, glass, plastic (resin), ceramic, and quartz, which is the target of surface treatment. Examples of monovalent reactive groups include monovalent groups selected from carbon-carbon double bond-containing groups (however, excluding alkenyl groups (groups that undergo hydrosilylation addition polymerization), and limited to groups involved in ionic addition polymerization or curing reactions by active energy rays (light)), carbon-carbon triple bond-containing groups, cyclic ether groups, hydroxyl group-containing groups, thiol groups, amino groups, azide groups, nitrogen-containing heterocyclic groups, phosphoric acid-containing groups, hydroxyl group-containing silyl groups (silanol groups), and hydrolyzable silyl groups.

[0032] Examples of A include carbon-carbon double bond-containing groups such as cinnamic acid group, sorbic acid group, acryloyl group, methacryloyl group, acryloyloxy group, methacryloyloxy group, acrylamide group, methacrylamide group, vinyl ether group; carbon-carbon triple bond-containing groups such as ethynyl group, propargyl group, 2-methyl-2-propynyl group, 3-butynyl group, 4-pentynyl group, and 5-hexynyl group, which have 2 to 20 carbon atoms, and alkynyloxy groups such as propargyloxy group, 2-methyl-2-propynyloxy group, 3-butynyloxy group, 4-pentynyloxy group, and 5-hexynyloxy group, which have 2 to 20 carbon atoms; cyclic A Examples of monovalent groups include tel groups such as epoxy groups, glycidyl groups, glycidyloxy groups, alicyclic epoxy groups, and oxetanyl groups; hydroxyl group-containing groups such as carboxyl groups and catechol groups; thiol groups; amino groups, alkylamino groups, and dialkylamino groups; azide groups; nitrogen-containing heterocyclic groups such as imidazolyl groups, triazolyl groups, benzotriazolyl groups, tetrazolyl groups, and isocyanate groups; phosphate-containing groups such as phosphate groups, phosphate ester groups, alkyl phosphate groups, and alkyl phosphate ester groups; phosphonic acid-containing groups such as phosphonic acid groups and phosphonic acid ester groups; and monovalent groups such as hydroxyl group-containing silyl groups (silanol groups), hydrolyzable silyl groups, and silazane groups. Among these, cyclic ether groups, hydroxyl group-containing silyl groups (silanol groups), hydrolyzable silyl groups, and silazane groups are preferred.

[0033] The following general formula (2) is used for hydroxyl group-containing silyl groups and hydrolyzable silyl groups. (In the formula, R 1 ) 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 from 1 to 3. The silazane group is represented by the following general formula (3) A base represented by (wherein n'' is a number from 0 to 3, and n' is (3 - n'') / 2) is preferred.

[0034] In the above equation (2), R 1 These are independently alkyl groups such as methyl, ethyl, propyl, and butyl groups having 1 to 4 carbon atoms, or phenyl groups, with methyl groups being preferred among them.

[0035] In formula (2) above, X is independently a hydroxyl group or a hydrolyzable group. Examples of such X include: hydroxyl groups; C1-C10 alkoxy groups such as methoxy, ethoxy, propoxy, isopropoxy, and butoxy groups; C2-C10 alkoxyalkoxy groups such as methoxymethoxy and methoxyethoxy groups; C3-C10 alkoxyalkoxy groups such as methoxyethoxyethoxy and ethoxyethoxymethoxy groups; C1-C10 acyloxy groups such as acetoxy groups; C2-C10 alkenyloxy groups such as isopropenoxy and cyclopentenyloxy groups; halogen groups, preferably without a fluorine atom, such as chlorine, bromo, and iodine groups; and C2-C10 dialkylamino groups such as dimethylamino and diethylamino groups. Among these, methoxy, ethoxy, isopropenoxy, and chlorine groups are preferred. X may be the same or different.

[0036] In the above formula (2), n is an integer between 1 and 3, preferably 3.

[0037] In formula (3) above, n'' is a number from 0 to 3 (a positive number less than or equal to 3), preferably n'' < 3, and more preferably n'' is 0. When n'' is 3 in formula (3) above, general formula (1) above represents the molecular formula (structural formula) of the hydrocarbon terminal group-containing compound (monomer monomer), and when n'' < 3 in formula (3) above, general formula (1) above represents the compositional formula of the hydrocarbon terminal group-containing compound (polysilazane compound). In formula (3) above, n' is (3 - n'') / 2, preferably 1.5.

[0038] In formula (1) above, k1 is a number indicating the number of repetitions of -Z-Y- and is an integer from 1 to 3. When k1 is 1 or greater, molecular mobility is improved by the linking functional group, and when k1 is 3 or less, the intermolecular interactions are large, making it easier for the molecular chains of the cured film to orient in one direction, while also maintaining molecular mobility. Furthermore, from the viewpoint of molecular mobility, it is preferable that k1 be 2 or 3, and when k1 is 1, it is more preferable that R in formula (1) above is the following formula (5). (In the formula, R 3 , R4 (The sum of y, h, and y and h is the same as above.)

[0039] In formula (1) above, k2 is an integer from 1 to 4, preferably an integer from 1 to 3. k3 is 0 or 1, preferably 0 when W is a single bond, and preferably 1 when W is not a single bond. Also, k4 is 0 or 1, preferably 0.

[0040] The following structures are examples of hydrocarbon terminal group-containing compounds represented by the above formula (1). By changing the combination of R, Z, Y, W, A, k1, k2, k3, and k4 in the above formula (1), several different hydrocarbon terminal group-containing compounds can be obtained.

[0041] (In the formula, x, y, a1, a2, b1, c1, and g are each independently the same as above. The total number of carbon atoms in the part corresponding to R in formula (1) is 10 or less, and the total number of carbon atoms in the part corresponding to Y is between 1 and 30.)

[0042] [Method for preparing hydrocarbon-terminated compound] Examples of methods for preparing the hydrocarbon-terminated compound represented by the general formula (1) of the present invention include the following: [Preparation method 1] A hydrocarbon-terminated compound having an alkenyl group at the terminal end and a compound having an SiH group and a hydrolyzable silyl group are mixed and subjected to a hydrosilylation addition reaction in the presence of a hydrosilylation catalyst to produce a hydrocarbon-terminated compound represented by formula (1) (particularly a compound having a hydrolyzable silyl group at the terminal end). If a compound having an SiH group and a hydrolyzable silyl group has a halogen group as the hydrolyzable group, the compound can then be produced by converting the substituent (halogen atom) on the silyl group to another hydrolyzable group.

[0043] Examples of hydrocarbon terminal group-containing compounds having an alkenyl group at the terminal include compounds represented by the following formulas (1A-1) or (1A-2). (In the formula, R, Z, Y, k1, k2, and k4 are the same as above. Y 1 is a monovalent hydrocarbon group having an alkenyl group with 2 to 30 carbon atoms, preferably 2 to 20 carbon atoms, W 2 (where p is a carbon atom, silicon atom, nitrogen atom, or a 3- to 5-valent organic group; p is an integer from 0 to 2.)

[0044] In the above equations (1A-1) and (1A-2), Y 1 Y is a monovalent hydrocarbon group having an alkenyl group with 2 to 30 carbon atoms, preferably 2 to 20 carbon atoms. 1 If the number of carbon atoms is three or more, it may be linear, branched, cyclic, or a combination thereof. 1 Examples include those having the terminals shown below. (In the formula, R 7 These are independently hydrogen atoms, or each Y 1 (A monovalent hydrocarbon group whose total number of carbon atoms in its structure is 30 or less.)

[0045] Y 1 The following are preferred. (In the formula, g is the same as above, a' is an independent integer of 0 or more, and the total number of carbon atoms in each of the above structures is 30 or less.)

[0046] In the above formula (1A-2), W 2 These are carbon atoms, silicon atoms, nitrogen atoms, or 3- to 5-valent organic groups, and examples include those similar to those in the above-mentioned W, but without the single bond.

[0047] Examples of compounds represented by formula (1A-1) are listed below. (In the formula, x, a1, and a' are the same as above.)

[0048] Examples of compounds represented by formula (1A-2) are listed below. (In the formula, x, y, a1, and a' are independently the same as above.)

[0049] The following methods can be used to prepare compounds represented by formula (1A-1) or (1A-2) (compounds containing hydrocarbon terminal groups having an alkenyl group at the terminal end). [Method for preparing compounds represented by formula (1A-1) or (1A-2) (1)] Compounds represented by formula (1A-1) or (1A-2) (compounds containing hydrocarbon terminal groups having an alkenyl group at the terminal end) can be produced by mixing a hydrocarbon terminal group containing a hydroxyl group at the terminal end with a base, adding a leaving group and a compound having an alkenyl group at the terminal end, and carrying out a nucleophilic substitution reaction.

[0050] Examples of hydrocarbon terminal group-containing compounds having a hydroxyl group at the terminal include compounds represented by the following formulas (1a-1) and (1a-2). (In the formula, R, Z, Y, W 2 k1, k2, and k4 are the same as above. p is an integer from 0 to 2. However, if k4 is 0, W 2 This is a 3- to 5-valent organic group, and the hydrogen atom enclosed in k2 bonds with the oxygen atom in W.

[0051] Examples of compounds represented by formula (1a-1) are listed below. (In the equation, x, y, and a1 are independently the same as above.)

[0052] Examples of compounds represented by formula (1a-2) are listed below. (In the formula, x and a1 are the same as above.)

[0053] Methods for preparing compounds represented by formula (1a-1) or (1a-2) include: a method of obtaining the target compound by reacting a compound having a hydroxyl group and a functional group other than a hydroxyl group with a hydrocarbon terminal group containing a functional group, without the hydroxyl group acting as an active group, by reacting the other functional groups with each other; a method of obtaining the target compound by reacting the functional groups of a compound having a protected hydroxyl group and a functional group with a hydrocarbon terminal group containing a functional group, thereby obtaining a hydrocarbon terminal group containing a protected hydroxyl group, and then deprotecting the group that protected the hydroxyl group; and other methods of obtaining the target compound by reduction of a carbonyl compound or hydroboration reaction.

[0054] Furthermore, examples of compounds having a leaving group and an alkenyl group at the terminal include compounds represented by the following formulas (1a-3) or (1a-4) as compounds to be reacted with the compound represented by the above formula (1a-1), and examples of compounds to be reacted with the compound represented by the above formula (1a-2) include the compound represented by (1a-3). (In the formula, Z, Y, Y 1 , W 2 k2 and k4 are the same as above. L is a halogen atom such as fluorine, chlorine, bromine, or iodine, or a leaving group such as mesylate or trilate. q is an integer between 0 and 2, and the sum of p and q is between 0 and 2.

[0055] Examples of compounds represented by the above formula (1a-3) include allyl bromide, 2-methylallyl bromide, and 11-bromo-1-undecene.

[0056] Examples of compounds represented by the above formula (1a-4) include those represented by the following formulas.

[0057] In the method (1) for preparing the compound represented by formula (1A-1) or (1A-2), the amount of compound having a leaving group and an alkenyl group at the terminal is preferably 1 to 5 mol, particularly 1 to 2 mol, per 1 mol of hydroxyl group in the hydrocarbon terminal group-containing compound having a hydroxyl group at the terminal.

[0058] In the method (1) for preparing the compound represented by formula (1A-1) or (1A-2), the base is not particularly limited, but examples include lithium hydroxide, sodium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, potassium tert-butoxide, etc. The amount of base used is preferably 1 to 3 mol, particularly 1 to 2 mol, per 1 mol of hydroxyl groups in the hydrocarbon terminal group-containing compound having a hydroxyl group at the terminal.

[0059] In the method (1) for preparing the compound represented by formula (1A-1) or (1A-2), a solvent can be used when carrying out the reaction. Examples of solvents include aromatic hydrocarbons such as toluene and xylene, aliphatic or alicyclic hydrocarbons such as n-pentane, n-hexane, and cyclohexane, cyclic ether compounds such as tetrahydrofuran and dioxane, and ketones such as acetone and methyl ethyl ketone. The amount of solvent used is preferably 0 to 2,000 parts by mass, particularly 50 to 1,500 parts by mass, per 100 parts by mass of the hydrocarbon terminal group-containing compound having a hydroxyl group at the terminal end.

[0060] In the method (1) for preparing the compound represented by formula (1A-1) or (1A-2), a catalyst can be added to convert the leaving group and the leaving group in the compound having an alkenyl group at the terminal end to one with higher leaving ability and to promote the reaction. The catalyst that promotes the reaction is not particularly limited, but examples include tetramethylammonium iodide, tetraethylammonium iodide, tetrapropylammonium iodide, tetrabutylammonium iodide, sodium iodide, potassium iodide, rubidium iodide, and cesium iodide. The amount of catalyst used is preferably 0.001 to 1 mol, particularly 0.005 to 0.25 mol, per 1 mol of hydroxyl group in the hydrocarbon terminal group-containing compound having a hydroxyl group at the terminal end.

[0061] In the method (1) for preparing the compound represented by formula (1A-1) or (1A-2), the reaction conditions are preferably a temperature of 20 to 100°C, particularly 30 to 60°C, for 0.5 to 72 hours, and especially 1 to 36 hours.

[0062] Further methods for preparing the compound represented by formula (1A-1) or (1A-2) (a hydrocarbon terminal group-containing compound having an alkenyl group at the terminal) include the following: [Method for preparing the compound represented by formula (1A-1) or (1A-2) (2)] A hydrocarbon terminal group-containing compound having a leaving group at the terminal and a compound having a hydroxyl group and an alkenyl group at the terminal can be mixed to produce the compound represented by formula (1A-1) or (1A-2) (a hydrocarbon terminal group-containing compound having an alkenyl group at the terminal).

[0063] Examples of hydrocarbon terminal group-containing compounds having a leaving group at its terminal include compounds represented by the following formula (1a-5). (In the formula, R, Z, Y, and L are the same as above. p1 is an integer between 0 and 3.)

[0064] The compounds represented by formula (1a-5) are not particularly limited, but examples include 1-bromooctane, 1-bromodecane, and compounds represented by the following formula. (In the formula, x and a1 are independently the same as above.)

[0065] Furthermore, examples of compounds having a hydroxyl group and an alkenyl group at their terminals include compounds represented by the following formulas (1a-6) or (1a-7). (In the formula, Z, Y, Y 1 , W 2 k2 and k4 are the same as above. q1 is an integer between 0 and 2, and the sum of p1 and q1 is between 0 and 2.

[0066] Examples of compounds represented by formula (1a-6) are listed below. (In the formula, a' is the same as above.)

[0067] Examples of compounds represented by formula (1a-7) are listed below. (In the formula, a1 and a' are independently the same as above.)

[0068] In the method (2) for preparing the compound represented by formula (1A-1) or (1A-2), the amount of hydrocarbon terminal group-containing compound having a leaving group at its terminal is preferably 1 to 5 mol, particularly 1 to 2 mol, per 1 mol of hydroxyl group in the compound having a hydroxyl group and an alkenyl group at its terminal.

[0069] In the method (2) for preparing the compound represented by formula (1A-1) or (1A-2), the base is not particularly limited, but examples include lithium hydroxide, sodium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, potassium tert-butoxide, etc. The amount of base used is preferably 1 to 3 mol, particularly 1 to 1.5 mol, per 1 mol of hydroxyl group in the compound having a terminal hydroxyl group and an alkenyl group.

[0070] In the method (2) for preparing the compound represented by formula (1A-1) or (1A-2), a solvent can be used when carrying out the reaction. Examples of solvents include aromatic hydrocarbons such as toluene and xylene, aliphatic or alicyclic hydrocarbons such as n-pentane, n-hexane, and cyclohexane, cyclic ether compounds such as tetrahydrofuran and dioxane, and ketones such as acetone and methyl ethyl ketone. The amount of solvent used is preferably 0 to 2,000 parts by mass, particularly 50 to 1,500 parts by mass, per 100 parts by mass of the hydrocarbon terminal group-containing compound having a leaving group at its terminal end.

[0071] In the method (2) for preparing the compound represented by formula (1A-1) or (1A-2), a catalyst can be added to convert the leaving group in the compound having a leaving group and an alkenyl group at its terminus to one with higher leaving ability and to promote the reaction. The catalyst that promotes the reaction is not particularly limited, but examples include tetramethylammonium iodide, tetraethylammonium iodide, tetrapropylammonium iodide, tetrabutylammonium iodide, sodium iodide, potassium iodide, rubidium iodide, and cesium iodide. The amount of catalyst used is preferably 0.001 to 1 mol, particularly 0.005 to 0.15 mol, per 1 mol of leaving group in the hydrocarbon terminal group-containing compound having a leaving group at its terminus.

[0072] In the method (2) for preparing the compound represented by formula (1A-1) or (1A-2), the reaction conditions are preferably a temperature of 20 to 100°C, particularly 25 to 60°C, for 0.5 to 72 hours, and especially 1 to 36 hours.

[0073] Further methods for preparing the compound represented by formula (1A-2) (a hydrocarbon terminal group-containing compound having an alkenyl group at the terminal) include the following: [Method for preparing the compound represented by formula (1A-2) (3)] A hydrocarbon terminal group-containing compound having an ester group at the terminal and an organometallic compound having an alkenyl group at the terminal can be mixed to produce the compound represented by formula (1A-2) (a hydrocarbon terminal group-containing compound having an alkenyl group at the terminal).

[0074] Here, examples of hydrocarbon terminal group-containing compounds having an ester group at the terminal include compounds represented by the following formula (1a-8). (In the formula, R, Z, Y, and k1 are the same as above. R 10 (This is a monovalent hydrocarbon group having 1 to 20 carbon atoms, preferably a methyl group or an ethyl group.)

[0075] The compounds represented by formula (1a-8) are not particularly limited, but examples include compounds represented by the following formulas. (In the formula, x, a1, R 10 (This is independently the same as above.)

[0076] Furthermore, examples of organometallic compounds having an alkenyl group at the terminal include vinyl magnesium bromide, allyl magnesium bromide, 3-butenyl magnesium bromide, and allyl magnesium chloride, although these are not particularly limited.

[0077] In the method (3) for preparing the compound represented by formula (1A-2), the amount of organometallic compound having an alkenyl group at the terminal is preferably 2 to 10 mol, particularly 2 to 5 mol, per 1 mol of hydrocarbon terminal group-containing compound having an ester group at the terminal.

[0078] In the method for preparing the compound represented by formula (1A-2) (3), a solvent can be used when carrying out the reaction. Examples of solvents include aromatic hydrocarbons such as toluene and xylene, aliphatic or alicyclic hydrocarbons such as n-pentane, n-hexane, and cyclohexane, cyclic ether compounds such as tetrahydrofuran and dioxane, dichloromethane, and 1,2-dichloroethane. The amount of solvent used is preferably 100 to 10,000 parts by mass, and more preferably 200 to 2,000 parts by mass, per 100 parts by mass of the hydrocarbon terminal group-containing compound having an ester group at the terminal end.

[0079] In the method (3) for preparing the compound represented by formula (1A-2), the reaction conditions are preferably a temperature of -78 to 100°C, particularly -20 to 50°C, for 0.5 to 72 hours, and especially 1 to 24 hours.

[0080] Further methods for preparing the compound represented by formula (1A-2) (a hydrocarbon terminal group-containing compound having an alkenyl group at its terminus) include the following: [Method for preparing the compound represented by formula (1A-2) (4)] A hydrocarbon terminal group-containing compound having a hydrolyzable silyl group at its terminus and an organometallic compound having an alkenyl group at its terminus can be mixed to produce the compound represented by formula (1A-2) (a hydrocarbon terminal group-containing compound having an alkenyl group at its terminus).

[0081] Examples of hydrocarbon-terminal group-containing compounds having a hydrolyzable silyl group at the terminal include compounds represented by the following formula (1a-9). (In the formula, R, R 1 Z, Y, and k1 are the same as above. X a n''' is an alkoxy group having 1 to 10 carbon atoms, an alkoxyalkoxy group having 2 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, or a halogen group.

[0082] The compounds represented by formula (1a-9) are not particularly limited, but examples include compounds represented by the following formulas. (In the formula, x, a1, R 1 , X a (n''' is independently the same as above.)

[0083] Furthermore, examples of organometallic compounds having an alkenyl group at the terminal include vinyl magnesium bromide, allyl magnesium bromide, 3-butenyl magnesium bromide, and allyl magnesium chloride, although these are not particularly limited.

[0084] In the method (4) for preparing the compound represented by formula (1A-2), the amount of organometallic compound having an alkenyl group at the terminal is preferably 3 to 10 mol, particularly 3 to 5 mol, per 1 mol of hydrocarbon-terminal compound having a hydrolyzable silyl group at the terminal.

[0085] In the method for preparing the compound represented by formula (1A-2) (4), a solvent can be used when carrying out the reaction. Examples of solvents include aromatic hydrocarbons such as toluene and xylene, aliphatic or alicyclic hydrocarbons such as n-pentane, n-hexane, and cyclohexane, cyclic ether compounds such as tetrahydrofuran and dioxane, dichloromethane, and 1,2-dichloroethane. The amount of solvent used is preferably 100 to 10,000 parts by mass, and more preferably 300 to 2,000 parts by mass, per 100 parts by mass of the hydrocarbon terminal group-containing compound having a hydrolyzable silyl group at the terminal end.

[0086] In the method (4) for preparing the compound represented by formula (1A-2), the reaction conditions are preferably a temperature of -78 to 100°C, particularly -20 to 50°C, for 0.5 to 72 hours, and especially 1 to 24 hours.

[0087] Further methods for preparing compounds represented by formula (1A-1) or (1A-2) (hydrocarbon end group-containing compounds having an alkenyl group at the terminal) include the following: [Method for preparing compounds represented by formula (1A-1) or (1A-2) (5)] Compounds represented by formula (1A-1) or (1A-2) (hydrocarbon end group-containing compounds having an alkenyl group at the terminal) can be produced by reacting a hydrocarbon end group-containing compound having an NH group at the terminal with a compound having an acid halide and an alkenyl group at the terminal.

[0088] Here, examples of hydrocarbon terminal group-containing compounds having an NH group at the terminal include compounds represented by the following formula (1a-10). (In the formula, R, R 5 Z and Y are the same as above. p is an integer between 0 and 2.

[0089] The compound represented by formula (1a-10) is not particularly limited, but examples include 1-aminooctane and 1-aminodecane.

[0090] Furthermore, examples of compounds having acid halide and alkenyl groups at their terminals include compounds represented by the following formulas (1a-11) or (1a-12). (In the formula, Z, Y, Y 1 , W 2 k2 and k4 are the same as above. X 1 (where p is a halogen atom, preferably a chlorine atom; q is an integer between 0 and 2, and the sum of p and q is between 0 and 2.)

[0091] The compounds represented by formulas (1a-11) and (1a-12) are not particularly limited, but examples include 10-undecenoyl chloride.

[0092] In the method (5) for preparing the compound represented by formula (1A-1) or (1A-2), the amount of hydrocarbon terminal group-containing compound having an NH group at the terminal is preferably 0.5 to 5 mol, particularly 0.8 to 3 mol, per 1 mol of the compound having an acid halide and an alkenyl group at the terminal.

[0093] In the method (5) for preparing the compound represented by formula (1A-1) or (1A-2), a base may be added to neutralize the hydrogen chloride generated during the reaction. The base is not particularly limited, but examples include triethylamine, tributylamine, 4-dimethylaminopyridine, N-ethyldiisopropylamine, 1,4-diazabicyclo[2.2.2]octane, and 1,8-diazabicyclo[5.4.0]-7-undecene. The amount of base used is preferably 1 to 3 mol, particularly 1 to 1.5 mol, per 1 mol of the compound having an acid halide and an alkenyl group at the terminals.

[0094] In addition, in the method for preparing the compound represented by formula (1A-1) or (1A-2) (5), a solvent can be used when carrying out the reaction. Examples of solvents include those similar to those exemplified in the solvent for the method for preparing the compound represented by formula (1A-1) or (1A-2) (1). The amount of solvent used is preferably 0 to 1,000 parts by mass, and more preferably 50 to 400 parts by mass, per 100 parts by mass of the compound having an acid halide and an alkenyl group at the terminals.

[0095] In the method (5) for preparing the compound represented by formula (1A-1) or (1A-2), the reaction conditions are preferably a temperature of 20 to 100°C, particularly 20 to 70°C, for 0.5 to 72 hours, particularly 1 to 36 hours.

[0096] Further methods for preparing the compound represented by formula (1A-1) or (1A-2) (a hydrocarbon terminal group-containing compound having an alkenyl group at its terminus) include the following: [Method for preparing the compound represented by formula (1A-1) or (1A-2) (6)] A hydrocarbon terminal group-containing compound having a leaving group at its terminus can be mixed with a base to produce the compound represented by formula (1A-1) or (1A-2) (a hydrocarbon terminal group-containing compound having an alkenyl group at its terminus).

[0097] Here, examples of hydrocarbon terminal group-containing compounds having a leaving group at the terminal include the compound represented by formula (1a-5) below, as described in method (2) for preparing the compound represented by formula (1A-1) or (1A-2). (In the formula, R, Z, Y, and L are the same as above. p1 is an integer between 0 and 3.)

[0098] The compounds represented by formula (1a-5) are not particularly limited, but examples include 1-bromooctane, 1-bromodecane, and compounds represented by the following formula. (In the formula, x and a1 are independently the same as above.)

[0099] In the method (6) for preparing the compound represented by formula (1A-1) or (1A-2), the base is not particularly limited, but examples include lithium hydroxide, sodium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, potassium tert-butoxide, etc. The amount of base used is preferably 1 to 3 mol, particularly 1 to 2 mol, per 1 mol of leaving group in the hydrocarbon terminal group-containing compound having a leaving group at its terminus.

[0100] In the method (6) for preparing the compound represented by formula (1A-1) or (1A-2), a solvent can be used when carrying out the reaction. Examples of solvents include aromatic hydrocarbons such as toluene and xylene, aliphatic or alicyclic hydrocarbons such as n-pentane, n-hexane, and cyclohexane, cyclic ether compounds such as tetrahydrofuran and dioxane, and ketones such as acetone and methyl ethyl ketone. The amount of solvent used is preferably 0 to 2,000 parts by mass, particularly 50 to 1,500 parts by mass, per 100 parts by mass of the hydrocarbon terminal group-containing compound having a leaving group at its terminal end.

[0101] In the method (6) for preparing the compound represented by formula (1A-1) or (1A-2), a catalyst can be added to convert the leaving group in the compound having a leaving group and an alkenyl group at its terminus to a more highly leaving group and to promote the reaction. The catalyst that promotes the reaction is not particularly limited, but examples include tetramethylammonium iodide, tetraethylammonium iodide, tetrapropylammonium iodide, tetrabutylammonium iodide, sodium iodide, potassium iodide, rubidium iodide, and cesium iodide. When adding the catalyst, the amount used is preferably 0.001 to 1 mol, particularly 0.005 to 0.15 mol, per 1 mol of leaving group in the hydrocarbon terminal group-containing compound having a leaving group at its terminus.

[0102] In the method (6) for preparing the compound represented by formula (1A-1) or (1A-2), the reaction conditions are preferably a temperature of 20 to 100°C, particularly 30 to 60°C, for 0.5 to 72 hours, and especially 1 to 36 hours.

[0103] Further methods for preparing the compound represented by formula (1A-1) or (1A-2) (a hydrocarbon-terminal group-containing compound having an alkenyl group at the terminal) include the following: [Method for preparing the compound represented by formula (1A-1) or (1A-2) (7)] By performing the oxazole synthesis described in reference [X] using a hydrocarbon-terminal group-containing compound having a hydroxyl group at the terminal, the compound represented by formula (1A-1) or (1A-2) (a hydrocarbon-terminal group-containing compound having a vinyl ether group at the terminal) can be produced. Reference [X] J. Am. Chem. Soc. 2002, 124, 8, 1590-1591

[0104] Examples of compounds having an SiH group and a hydrolyzable silyl group in preparation method 1 include trimethoxysilane, triethoxysilane, triacetoxysilane, and trichlorosilane.

[0105] In preparation method 1, the amount of compound having an SiH group and a hydrolyzable silyl group used is preferably 1 to 10 mol, particularly 5 to 10 mol, per 1 mol of alkenyl group in the hydrocarbon terminal group-containing compound having an alkenyl group at the terminal end.

[0106] In preparation method 1, examples of the hydrosilylation reaction catalyst include platinum black, chloroplatinic acid, alcohol-modified chloroplatinic acid, complexes of chloroplatinic acid with olefins, aldehydes, vinylsiloxanes, acetylene alcohols, etc., and platinum group metal catalysts such as tetrakis(triphenylphosphine)palladium and chlorotris(triphenylphosphine)rhodium. Preferably, it is a platinum-based compound such as a vinylsiloxane coordination compound. It is preferable to dissolve the platinum-based compound in a solvent such as toluene, lower alcohol, higher alcohol, or silicone-based solvent before use. The amount of hydrosilylation reaction catalyst used is preferably 0.001 to 1,000 ppm in terms of transition metal (mass) relative to the mass of the hydrocarbon terminal group-containing compound having an alkenyl group at the terminal, and more preferably 0.01 to 100 ppm.

[0107] In preparation method 1, a co-catalyst to activate the hydrosilylation reaction and a co-catalyst to prevent the conversion of alkenyl groups can be used. Examples of co-catalysts to activate the hydrosilylation reaction include acetic acid, formic acid, and propionic acid. Examples of co-catalysts to prevent the conversion of alkenyl groups include formamide, acetamide, and acetonitrile. When these co-catalysts are incorporated, the amount used is preferably 10 to 1,000,000 ppm by mass, and more preferably 100 to 10,000 ppm, relative to the mass of the hydrocarbon terminal group-containing compound having an alkenyl group at the terminal end.

[0108] In preparation method 1, a solvent can be used when carrying out the reaction. Examples of solvents include aromatic hydrocarbons such as toluene and xylene, aliphatic or alicyclic hydrocarbons such as n-pentane, n-hexane, and cyclohexane, cyclic ether compounds such as tetrahydrofuran and dioxane, and ketones such as acetone and methyl ethyl ketone. The amount of solvent used is preferably 0 to 1,000 parts by mass, and more preferably 50 to 500 parts by mass, per 100 parts by mass of the hydrocarbon terminal group-containing compound having an alkenyl group at the terminal end.

[0109] In preparation method 1, the reaction conditions for the hydrocarbon terminal group-containing compound having an alkenyl group at its terminus and the compound having an SiH group and a hydrolyzable silyl group are preferably a temperature of 20 to 120°C, particularly 60 to 100°C, for 0.5 to 72 hours, and especially 1 to 36 hours.

[0110] In preparation method 1, if a compound having a SiH group and a hydrolyzable silyl group is used, such as trichlorosilane, in which the hydrolyzable group is a halogen group (a compound containing an SiH group and a silyl halogen group), the substituent (halogen atom) on the silyl group can then be converted to another hydrolyzable group, such as an alkoxy group like a methoxy group. Examples of compounds that can be used to convert the substituent (halogen atom) on the silyl group to another hydrolyzable group include methanol, ethanol, isopropanol, ethylene glycol monomethyl ether, and trimethyl orthoformate. The amount used is preferably 3 to 9 mol, particularly 3 to 5 mol, per 1 mol of halogen atoms in the reaction product of the hydrocarbon terminal group-containing compound having an alkenyl group at the terminal and the SiH group and silyl halogen group-containing compound.

[0111] In preparation method 1, the reaction conditions for converting substituents (halogen atoms) on the silyl group to other hydrolyzable groups are preferably a temperature of 0 to 80°C, particularly 20 to 60°C, for 0.5 to 72 hours, and especially 1 to 36 hours.

[0112] Other methods for preparing hydrocarbon terminal group-containing compounds represented by the general formula (1) of the present invention include the following: [Preparation Method 2] A hydrocarbon terminal group-containing compound having an SiH group at the terminal end can be mixed with a compound having a reactive group such as an alkenyl group and a hydrolyzable silyl group, and a hydrosilylation addition reaction can be carried out in the presence of a hydrosilylation catalyst to produce a hydrocarbon terminal group-containing compound represented by formula (1) (particularly a compound having a hydrolyzable silyl group at the terminal end).

[0113] Here, examples of hydrocarbon terminal group-containing compounds having an SiH group at the terminal include compounds represented by the following formula (1B). (In the formula, R, Z, Y, k1, k2 are the same as above. W 1 These are linear or branched or cyclic organopolysiloxane residues with 2 to 10 silicon atoms, or with 3 to 10 silicon atoms, and are 3 to 5 valent.

[0114] In the above formula (1B), W 1These are linear organopolysiloxane residues with 2 to 10 silicon atoms, or branched or cyclic organopolysiloxane residues with 3 to 10 silicon atoms, particularly branched or cyclic organopolysiloxane residues with 3 to 8 silicon atoms, provided that the hydrogen atoms enclosed in k2 are bonded to silicon atoms. 1 Examples are shown below. In the structure below, the bond on the left bonds with Y, and the other bonds bond with hydrogen atoms.

[0115] Examples of compounds represented by formula (1B) are listed below. (In the formula, x and a1 are independently the same as above.)

[0116] Furthermore, among compounds having reactive groups such as alkenyl groups and hydrolyzable silyl groups, examples of compounds having alkenyl groups and hydrolyzable silyl groups include vinyltrimethoxysilane, allyltrimethoxysilane, allyltriethoxysilane, and octenyltrimethoxysilane. Examples of compounds having reactive groups other than alkenyl groups and hydrolyzable silyl groups include allylglycidyl ether.

[0117] In preparation method 2, the amount of compound having reactive groups such as alkenyl groups and hydrolyzable silyl groups used is preferably 1 to 10 mol, particularly 1 to 5 mol, per 1 mol of SiH groups in the hydrocarbon terminal group-containing compound having an SiH group at the terminal end.

[0118] In preparation method 2, the hydrosilylation reaction catalyst can be the same as that exemplified in the hydrosilylation reaction catalyst of preparation method 1 above. Preferably, it is a platinum-based compound such as a vinylsiloxane coordination compound. The platinum-based compound is preferably used dissolved in a solvent such as toluene, a lower alcohol, a higher alcohol, or a silicone-based solvent. The amount of hydrosilylation reaction catalyst used is preferably 0.001 to 1,000 ppm in terms of transition metal (mass) relative to the mass of the hydrocarbon-terminated compound having an SiH group at the terminal, and more preferably 0.01 to 100 ppm.

[0119] In preparation method 2, a co-catalyst to activate the hydrosilylation reaction and a co-catalyst to prevent the conversion of alkenyl groups can be used. Examples of co-catalysts to activate the hydrosilylation reaction include acetic acid, formic acid, and propionic acid. Examples of co-catalysts to prevent the conversion of alkenyl groups include formamide, acetamide, and acetonitrile. When these co-catalysts are incorporated, the amount used is preferably 10 to 1,000,000 ppm by mass, and more preferably 100 to 10,000 ppm, relative to the mass of the hydrocarbon-terminated compound having an SiH group at the terminal end.

[0120] In preparation method 2, a solvent can be used when carrying out the reaction. Examples of solvents are the same as those exemplified in the solvent for preparation method 1 above. The amount of solvent used is preferably 0 to 1,000 parts by mass, and more preferably 50 to 200 parts by mass, per 100 parts by mass of the hydrocarbon terminal group-containing compound having an SiH group at the terminal end.

[0121] In preparation method 2, the reaction conditions are preferably a temperature of 20 to 120°C, particularly 60 to 100°C, for 0.5 to 72 hours, and especially 1 to 36 hours.

[0122] Other methods for preparing the hydrocarbon terminal group-containing compound represented by the general formula (1) of the present invention include the following: [Preparation Method 3] A hydrocarbon terminal group-containing compound having an alkenyl group at the terminal and trichlorosilane are mixed and reacted in the presence of a hydrosilylation catalyst, and then the resulting compound is reacted with ammonia gas to produce a hydrocarbon terminal group-containing compound represented by formula (1) (particularly a compound having an amino group-containing silyl group at the terminal and / or a polysilazane compound which is a polymer thereof).

[0123] Here, the reaction product of the hydrocarbon-terminal group-containing compound having an alkenyl group at its terminus and trichlorosilane can be prepared in the same manner as in Preparation Method 1.

[0124] In preparation method 3, the amount of ammonia gas used is preferably 1 to 300 cc / min, and more preferably 30 to 200 cc / min.

[0125] In preparation method 3, a solvent can be used when reacting the reaction product of the hydrocarbon terminal group-containing compound having an alkenyl group at the terminal end and trichlorosilane with ammonia gas. Examples of solvents are the same as those exemplified in preparation method 1 above. The amount of solvent used is preferably 0 to 1,000 parts by mass, particularly 50 to 300 parts by mass, per 100 parts by mass of the reaction product of the hydrocarbon terminal group-containing compound having an alkenyl group at the terminal end and trichlorosilane.

[0126] In preparation method 3, the reaction conditions for the reaction product of the hydrocarbon terminal group-containing compound having an alkenyl group at the terminal end and trichlorosilane with ammonia gas are preferably at room temperature (23 ± 15°C, the same applies hereinafter), particularly 20 to 30°C, for 2 to 36 hours, and especially 4 to 12 hours.

[0127] Other methods for preparing the hydrocarbon terminal group-containing compound represented by the general formula (1) of the present invention include the following: [Preparation Method 4] A hydrocarbon terminal group-containing compound having a hydroxyl group at the terminal end can be mixed with phosphorus oxychloride and reacted, and then water can be added and reacted to produce a hydrocarbon terminal group-containing compound represented by formula (1) (particularly a compound having a reactive group such as a phosphate group at the terminal end).

[0128] Here, examples of hydrocarbon terminal group-containing compounds having a hydroxyl group at the terminal include the compounds represented by formulas (1a-1) and (1a-2) described in the preparation method (1) for the compound represented by formula (1A-1) or (1A-2).

[0129] In preparation method 4, the amount of phosphorus oxychloride used is preferably 1 to 4 mol, particularly 1 to 2 mol, per 1 mol of hydroxyl groups in the hydrocarbon-terminal group-containing compound having a hydroxyl group at the terminal end.

[0130] In preparation method 4, a solvent can be used when reacting a hydrocarbon end group-containing compound having a hydroxyl group at its terminal with phosphorus oxychloride. Examples of solvents are the same as those exemplified in preparation method 1 above. The amount of solvent used is preferably 0 to 1,000 parts by mass, particularly 50 to 500 parts by mass, per 100 parts by mass of the hydrocarbon end group-containing compound having a hydroxyl group at its terminal.

[0131] In preparation method 4, the reaction conditions for the hydrocarbon terminal group-containing compound having a hydroxyl group at its terminus and phosphorus oxychloride are preferably a temperature of 0 to 80°C, particularly 15 to 50°C, for 0.5 to 72 hours, and especially 1 to 36 hours.

[0132] In preparation method 4, the amount of water used is preferably 50 to 1,000 parts by mass, and particularly preferably 100 to 500 parts by mass, per 100 parts by mass of the hydrocarbon terminal group-containing compound having a hydroxyl group at its end.

[0133] In preparation method 4, the reaction conditions for the reaction product of a hydrocarbon terminal group-containing compound having a hydroxyl group at its terminus and phosphorus oxychloride with water are preferably a temperature of 0 to 80°C, particularly 15 to 50°C, for 0.5 to 72 hours, and especially 1 to 36 hours.

[0134] Other methods for preparing the hydrocarbon terminal group-containing compound represented by the general formula (1) of the present invention include the following: [Preparation Method 5] A hydrocarbon terminal group-containing compound having a hydroxyl group at its terminus and a compound having an isocyanate group and a reactive group (for example, a hydrolyzable silyl group or a (meth)acryloyloxy group, etc.) are mixed and reacted in the presence of a catalyst to produce a hydrocarbon terminal group-containing compound represented by formula (1) (in particular, a compound having a reactive group such as a hydrolyzable silyl group or a (meth)acryloyloxy group at its terminus via a urethane bond). In this invention, (meth)acryloyloxy group refers to an acryloyloxy group or a methacryloyloxy group.

[0135] Here, examples of hydrocarbon terminal group-containing compounds having a hydroxyl group at the terminal include compounds represented by the following formula (1C). (In the formula, R, Z, and Y are the same as above. p is an integer between 0 and 2.)

[0136] Examples of compounds represented by formula (1C) are listed below. (In the formula, x and a1 are independently the same as above.)

[0137] The following methods can be used to prepare the compound represented by formula (1C) (a hydrocarbon terminal group-containing compound having a hydroxyl group at its terminus). [Method for preparing the compound represented by formula (1C) (1)] A hydrocarbon terminal group-containing compound represented by formula (1C) can be produced by mixing a hydrocarbon terminal group-containing compound having a thiol group at its terminus with a compound having a hydroxyl group and an alkenyl group at its terminus and reacting them in the presence of a polymerization initiator.

[0138] Examples of hydrocarbon terminal group-containing compounds having a thiol group at the terminal include compounds represented by the following formula (1c-1). (In the formula, R, Z, and Y are the same as above. p2 is 0 or 1.)

[0139] Examples of compounds represented by formula (1c-1) are listed below. (In the formula, x is the same as above.)

[0140] Examples of compounds having a hydroxyl group and an alkenyl group at their terminals include the compound represented by the following formula (1c-2). (In the formula, Y 1 Z, Y, and A are the same as above. q2 is 0 or 1, and the sum of p2 and q2 is 0 or 1.

[0141] Examples of compounds represented by formula (1c-2) are listed below. (In the formula, a' is the same as above.)

[0142] In the method (1) for preparing the compound represented by formula (1C), the amount of hydrocarbon terminal group-containing compound having a thiol group at the terminal is preferably 1 to 3 mol, particularly 1 to 1.5 mol, per 1 mol of compound having a hydroxyl group and an alkenyl group at the terminal.

[0143] In the method (1) for preparing the compound represented by formula (1C), examples of polymerization initiators include azo compounds such as 2,2'-azobisisobutyronitrile and 2,2'-azobis(isobutyrate)dimethyl, diacyl peroxides such as benzoyl peroxide and lauroyl peroxide, dialkyl peroxides such as dicumyl peroxide and di-tert-butyl peroxide, peroxycarbonates such as diisopropyl peroxydicarbonate and bis(4-tert-butylcyclohexyl) peroxydicarbonate, and alkyl peresters such as tert-butyl peroxyoctoate and tert-butyl peroxybenzoate. The amount of polymerization initiator used is preferably 0.01 to 3 mol, particularly 0.1 to 1.5 mol, per 1 mol of thiol groups in the hydrocarbon terminal group-containing compound having a thiol group at the terminal.

[0144] In addition, in the method (1) for preparing the compound represented by formula (1C), a solvent can be used when carrying out the reaction. Examples of solvents are the same as those exemplified in the solvent for preparation method 1 above. The amount of solvent used is preferably 0 to 1,000 parts by mass, particularly 50 to 800 parts by mass, per 100 parts by mass of the compound having a hydroxyl group and an alkenyl group at its terminals.

[0145] In the method (1) for preparing the compound represented by formula (1C), the reaction conditions are preferably a temperature of 20 to 100°C, particularly 40 to 80°C, for 0.5 to 72 hours, and especially 1 to 36 hours.

[0146] Furthermore, examples of compounds having an isocyanate group and a reactive group in preparation method 5 include 3-isocyanatopropyltrimethoxysilane, 3-isocyanatopropyltriethoxysilane, and 1,1-(bisacryloyloxymethyl)ethyl isocyanate.

[0147] In preparation method 5, the amount of compound having an isocyanate group and a reactive group used is preferably 1 to 3 mol, particularly 1 to 1.5 mol, per 1 mol of hydroxyl group in the hydrocarbon terminal group-containing compound having a hydroxyl group at the terminal end.

[0148] In preparation method 5, examples of catalysts include titanium compounds such as tetrakis(2-ethylhexyl) orthotitanate, tetra-n-butyl titanate, and tetra-n-propyl titanate; zirconium compounds such as tetra-n-butyl zirconate and tetra-n-propyl zirconate; tin compounds such as dibutyltin dimethoxide and dibutyltin dilaurate; bismuth compounds such as bismastris(2-ethylhexanoate); and amine catalysts such as diazabicycloundecene. The amount of catalyst used is 0.01 to 100 parts by mass, particularly preferably 0.1 to 20 parts by mass, per 100 parts by mass of the hydrocarbon-terminated compound having a hydroxyl group at its terminus.

[0149] In preparation method 5, a solvent can be used when carrying out the reaction. Examples of solvents are the same as those exemplified in the solvent for preparation method 1 above. The amount of solvent used is preferably 0 to 1,000 parts by mass, particularly 50 to 500 parts by mass, per 100 parts by mass of the hydrocarbon terminal group-containing compound having a hydroxyl group at the terminal end.

[0150] In preparation method 5, the reaction conditions are preferably a temperature of 20 to 100°C, particularly 30 to 60°C, for 0.5 to 72 hours, and especially 1 to 36 hours.

[0151] Other methods for preparing the hydrocarbon terminal group-containing compound represented by the general formula (1) of the present invention include the following: [Preparation Method 6] A hydrocarbon terminal group-containing compound represented by formula (1) can be produced by mixing a hydrocarbon terminal group-containing compound having an alkenyl group at the terminal with a compound having a thiol group and a reactive group (e.g., a hydrolyzable silyl group) at the terminal, or a hydrocarbon terminal group-containing compound having a thiol group at the terminal with a compound having an alkenyl group and a reactive group (e.g., a hydrolyzable silyl group) at the terminal, and reacting them in the presence of a polymerization initiator.

[0152] Examples of hydrocarbon terminal group-containing compounds having an alkenyl group at the terminal include compounds represented by the following formulas (1E-1) or (1E-2). (In the formula, R, Z, Y, Y 1 (p is the same as above. R' is a monovalent hydrocarbon group with 1 to 8 carbon atoms.)

[0153] In the above formula (1E-1), R' is a monovalent hydrocarbon group having 1 to 8 carbon atoms, and the following are examples. (In the formula, x' is an integer between 0 and 7.)

[0154] Examples of compounds represented by formula (1E-1) are listed below. (In the formula, x' is the same as above.)

[0155] Examples of compounds represented by formula (1E-2) are listed below. (In the formula, x, a1, and a' are independently the same as above.)

[0156] Here, the compound represented by formula (1E-2) can be prepared by the same method as the compound represented by formula (1A-1) described above.

[0157] Furthermore, examples of compounds having a thiol group and a reactive group at the terminal include compounds represented by the following formula (1F). (In the formula, Z, Y, and A are the same as above. q is an integer between 0 and 2, and the sum of p and q is between 0 and 2.)

[0158] Examples of compounds represented by formula (1F) are listed below. (In the formula, a1 is the same as above.)

[0159] Furthermore, examples of hydrocarbon terminal group-containing compounds having a thiol group at the terminal include compounds represented by the following formula (1G). (In the formula, R, Z, Y, and p are the same as above.)

[0160] Examples of compounds represented by formula (1G) are listed below. (In the formula, x is the same as above.)

[0161] Here, in the case of the compound represented by formula (1G) where p is 1 or 2, possible preparation methods include a method in which a compound having a thiol group and a functional group other than a thiol group reacts with a hydrocarbon terminal group containing a functional group, without the thiol group acting as an active group, to obtain the target compound by reacting the other functional groups with each other; a method in which a compound having a protected thiol group and a functional group reacts with the functional groups of a hydrocarbon terminal group containing a functional group to obtain a hydrocarbon terminal group containing a protected thiol group, and then deprotecting the group that protected the thiol group to obtain the target compound.

[0162] Furthermore, in preparation method 6, examples of compounds having an alkenyl group and a reactive group at the terminal include compounds represented by the following formula (1H). (In the formula, Y 1 (Z, Y, A, q, and p+q are the same as above.)

[0163] Examples of compounds represented by formula (1H) are listed below. (In the formula, a' is the same as above.)

[0164] In preparation method 6, the amount of compound having a thiol group and a reactive group at the terminal is preferably 1 to 5 mol, particularly 1 to 3 mol, per 1 mol of alkenyl group in the hydrocarbon terminal group-containing compound having an alkenyl group at the terminal.

[0165] In preparation method 6, examples of polymerization initiators include azo compounds such as 2,2'-azobisisobutyronitrile and 2,2'-azobis(isobutyrate)dimethyl, diacyl peroxides such as benzoyl peroxide and lauroyl peroxide, dialkyl peroxides such as dicumyl peroxide and di-tert-butyl peroxide, peroxycarbonates such as diisopropyl peroxydicarbonate and bis(4-tert-butylcyclohexyl) peroxydicarbonate, and alkyl peresters such as tert-butyl peroxyoctoate and tert-butyl peroxybenzoate. The amount of polymerization initiator used is preferably 0.01 to 3 mol, particularly 0.1 to 1.5 mol, per 1 mol of alkenyl group in the hydrocarbon terminal group-containing compound having an alkenyl group at the terminal or thiol group in the hydrocarbon terminal group-containing compound having a thiol group at the terminal.

[0166] In preparation method 6, a solvent can be used when carrying out the reaction. Examples of solvents are the same as those exemplified in the solvent for preparation method 1 above. The amount of solvent used is preferably 0 to 2,000 parts by mass, particularly 50 to 1,000 parts by mass, per 100 parts by mass of the hydrocarbon terminal group-containing compound having an alkenyl group at the terminal or the hydrocarbon terminal group-containing compound having a thiol group at the terminal.

[0167] In preparation method 6, the reaction conditions are preferably a temperature of 20 to 100°C, particularly 40 to 80°C, for 0.5 to 72 hours, and especially 1 to 36 hours.

[0168] [Surface Treatment Agent] The present invention further provides a non-fluorine surface treatment agent containing a hydrocarbon terminal group-containing compound represented by formula (1) above (i.e., a compound that does not have a fluorine atom in its molecule). The surface treatment agent only needs to contain the hydrocarbon terminal group-containing compound represented by formula (1), and may also contain unreacted raw materials and reaction intermediates before the introduction of the reactive group of the hydrocarbon terminal group-containing compound represented by formula (1). Furthermore, it is preferable to use a surface treatment agent in which the reactive group of the hydrocarbon terminal group-containing compound is a hydrolyzable silyl group, and in this case, the surface treatment agent may also contain a partially hydrolyzed condensate obtained by partially hydrolyzing and condensing the hydrolyzable silyl group by a known method.

[0169] When the reactive group of the hydrocarbon-terminal group-containing compound is a hydrolyzable silyl group, the surface treatment agent may optionally contain hydrolysis condensation catalysts, such as organotin compounds (e.g., dibutyltin dimethoxide, dibutyltin dilaurate), organotitanium compounds (e.g., tetra-n-butyl titanate, tetra-n-propyl titanate), organozirconium compounds (e.g., tetra-n-butyl zirconate, tetra-n-propyl zirconate), organic acids (e.g., acetic acid, methanesulfonic acid, carboxylic acid), inorganic acids (e.g., hydrochloric acid, sulfuric acid), or organic bases (e.g., amines, trialkylamines, nitrogen-containing cyclic compounds). Among these, acetic acid, tetra-n-butyl titanate, and dibutyltin dilaurate are particularly desirable. The amount of hydrolysis condensation catalyst added is a catalytic amount, usually 0.001 to 5 parts by mass, particularly 0.1 to 1 part by mass, per 100 parts by mass of the hydrocarbon-terminal group-containing compound (and / or its partially hydrolyzed condensate).

[0170] The surface treatment agent may contain a suitable solvent. Such solvents are preferably non-fluorinated solvents, and examples include hydrocarbon solvents (petroleum benzine, toluene, xylene, hexane, cyclohexane, methylcyclohexane, ethylcyclohexane, heptane, octane (n-octane, isooctane, etc.), nonane (n-nonane, isononane, etc.)), ketone solvents (acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclopentanone, cyclohexanone, etc.), ether solvents (tetrahydrofuran (THF), dipropyl ether, dibutyl ether, methylcyclopentyl ether, methyl tert-butyl ether, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, triethylene glycol dimethyl ether, propylene glycol dimethyl ether, etc.), alcohol solvents (propylene glycol monomethyl ether, butanol, isopropanol, etc.), and ester solvents (ethyl acetate, propyl acetate, butyl acetate, pentyl acetate, propylene glycol monomethyl ether acetate). Among these, toluene, hexane, heptane, isooctane, isononane, cyclopentanone, dipropyl ether, dibutyl ether, methylcyclopentyl ether, methyl tert-butyl ether, ethylene glycol dimethyl ether, propyl acetate, butyl acetate, and propylene glycol monomethyl ether acetate are preferred in terms of solubility, wettability, etc.

[0171] The above solvents may be mixed in two or more forms, and it is preferable to uniformly dissolve the hydrocarbon end group-containing compound. The optimal concentration of the hydrocarbon end group-containing compound to be dissolved in the solvent varies depending on the processing method, and any amount that is easy to weigh is acceptable. However, when direct coating, it is preferable to use 0.01 to 100 parts by mass, particularly 0.05 to 30 parts by mass, per 100 parts by mass of the total of the solvent and hydrocarbon end group-containing compound. When vapor deposition is performed, it is preferable to use 1 to 100 parts by mass, particularly 3 to 50 parts by mass, per 100 parts by mass of the total of the solvent and hydrocarbon end group-containing compound. In either coating case, 100 parts by mass refers to the case where no solvent is used and the coating is performed directly.

[0172] The surface treatment agent of the present invention can be applied to a substrate by known methods such as brush application, dipping, spraying, and vapor deposition. The heating method during vapor deposition can be either resistance heating or electron beam heating, and is not particularly limited. The curing conditions vary depending on the curing method, but for example, in the case of direct coating (brush application, dipping, spraying, etc.), it is preferable to use 25 to 200°C, particularly 25 to 150°C, for 30 minutes to 36 hours, and especially 1 to 24 hours, while in the case of application by vapor deposition, it is desirable to use a temperature range of 20 to 200°C for 1 to 24 hours. Curing may also be performed under humid conditions. Furthermore, for example, when using a hydrocarbon terminal group-containing compound having a hydrolyzable silyl group, in spray coating, diluting it in an organic solvent with water added beforehand and performing hydrolysis, i.e., generating Si-OH, before spray coating will result in faster curing after coating.

[0173] The thickness of the cured film is appropriately selected depending on the type of substrate, but is usually 0.1 to 100 nm, and particularly 1 to 20 nm. The film thickness can be measured by methods such as spectral reflectance measurement, X-ray reflectance measurement, spectral ellipsometry measurement, and X-ray fluorescence measurement.

[0174] The substrate to be treated with the surface treatment agent of the present invention is not particularly limited and may be made of various materials such as paper, cloth, metals and their oxides, glass, plastics, ceramics, and quartz. SiO2-treated glass and film are particularly preferred.

[0175] The surface treatment agent of the present invention can form a hardened film with a high level of water repellency and excellent abrasion resistance.

[0176] [Articles] Articles treated with the surface treatment agent of the present invention include car navigation systems, mobile phones, smartphones, digital cameras, digital video cameras, PDAs, portable audio players, car audio systems, game consoles, eyeglass lenses, camera lenses, lens filters, sunglasses, medical devices such as endoscopes, photocopiers, PCs, liquid crystal displays, organic EL displays, plasma displays, touch panel displays, protective films, anti-reflective films, and other optical articles and electronic components. The surface treatment agent of the present invention can impart scratch resistance to the above articles, and is therefore particularly useful as a water-repellent layer for touch panel displays, anti-reflective films, eyeglass lenses, and the like.

[0177] Furthermore, the surface treatment agent of the present invention is also useful as an anti-fouling coating for sanitary products such as bathtubs and washbasins, an anti-fouling coating for windows or tempered glass of automobiles, trains, and aircraft, headlamp covers, etc., a water-repellent coating for exterior wall building materials, a stain-preventing coating for kitchen building materials, an anti-fouling and anti-sticker / graffiti coating for telephone booths, a coating to prevent dirt from adhering to works of art, etc., and a stain-preventing coating for compact discs, DVDs, etc.

[0178] 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. In the following examples, the mol amount of the compound is, with respect to the measured mass of the target compound, 1 The value was calculated by dividing by the molecular weight of the polymer identified by 1H-NMR analysis. Furthermore, the film thickness was measured using spectroscopic ellipsometry with a spectroscopic ellipsometer. The room temperature was 25°C.

[0179] [Synthesis Example 1] Synthesis Example 1-1 In a reaction vessel, 100.00 g (5.87 x 10) of 10-undecene-1-ol was added. -1 mol), tetrahydrofuran 500.00 g, tetrabutylammonium iodide 21.68 g (5.87 x 10 -2 mol), and potassium tert-butoxide 98.86 g (8.81 x 10⁻¹⁰) -1The mixture (mol) was aged at 50°C for 1 hour. Then, 186.00 g of 1-bromodecan (8.41 x 10) was added. -1 A mol (unit of volume) was added dropwise, and the mixture was aged at 25°C for 24 hours. 400.00 g of saturated ammonium chloride aqueous solution was added to the resulting solution, and the aqueous layer was extracted three times with toluene. The combined organic layers were washed with pure water and saturated brine, and dried over magnesium sulfate. Subsequently, the mixture was treated with activated carbon and Kyoward 500, and the solvent and unreacted materials were removed by vacuum distillation to obtain 81.55 g of product.

[0180] The resulting compound was 1 ¹H-NMR confirmed that the structure is represented by the following formula (A).

[0181] Synthesis Example 1-2 In the reaction vessel, the following formula (A) obtained in Synthesis Example 1-1 2.00 g (6.44 × 10) of the compound represented by -3 mol), toluene 2.00g, trimethoxysilane 3.93g (3.22 x 10 -2 mol), 2.60 × 10¹³ toluene solution of chloroplatinic acid / vinylsiloxane complex -3 g (8.05 × 10 as Pt alone) -9 (containing mol), and formamide 3.30 × 10 -3 g (7.33 × 10 -5 The mixture (mol) was aged at 80°C for 24 hours. After that, the solvent and unreacted materials were removed by vacuum distillation to obtain 2.71 g of product.

[0182] The resulting compound was 1 ¹H-NMR confirmed that the structure is represented by the following formula (B).

[0183] [Synthesis Example 2] In the reaction vessel, the following formula (A) obtained in the same manner as in Synthesis Example 1-1 65.00 g (2.09 × 10) of the compound represented by -1 mol), toluene 50.00g, 3-thiolpropyltrimethoxysilane 45.20g (2.30 x 10 -1 mol), and 4.81 g (2.09 x 10) of 2,2'-azobis(isobutyrate)dimethyl -2(mol) were mixed and aged at 75 °C for 3 hours. Then, the solvent and unreacted substances were distilled off under reduced pressure to obtain 105.91 g of the product.

[0184] The obtained compound 1 was confirmed to have the structure represented by the following formula (C) by 1H-NMR.

[0185] [Synthesis Example 3] Synthesis Example 3-1 In a reaction vessel, 3.56 g (2.04×10 -2 mol) of 1-decanethiol, 25.00 g of toluene, 5.00 g (2.14×10 -2 mol) of 11-bromo-1-undecene, and 4.81×10 -1 g (2.09×10 -3 mol) of 2,2'-azobis(isobutyric acid) dimethyl were mixed and aged at 75 °C for 1 hour. Then, the solvent and unreacted substances were distilled off under reduced pressure to obtain 7.97 g of the product.

[0186] The obtained compound 1 was confirmed to have the structure represented by the following formula (D) by 1H-NMR.

[0187] Synthesis Example 3-2 In a reaction vessel, 7.50 g (1.84×10 mol) of the compound represented by the following formula (D) obtained in Synthesis Example 3-1, 20.00 g of tetrahydrofuran, and 4.50 g (4.01×10 -2 mol) of potassium tert-butoxide were mixed and aged at 50 °C for 24 hours. 50.00 g of a saturated aqueous ammonium chloride solution was added to the obtained solution, and the aqueous layer was extracted 3 times with toluene. The combined organic layers were washed with pure water and saturated brine and dried over magnesium sulfate. Then, activated carbon treatment was performed, the solvent and unreacted substances were distilled off under reduced pressure, and purification by silica gel column chromatography was carried out to obtain 4.43 g of the product.

[0188] The obtained compound 1 was confirmed to have the structure represented by the following formula (E) by 1H-NMR.

[0189] Synthesis Example 3-3 In a reaction vessel, the following formula (E) obtained in Synthesis Example 3-2​​ 2.00 g (6.12×10 -3 mol) of the compound represented by, 2.00 g of toluene, 3.74 g (3.06×10 -2 mol) of trimethoxysilane, 2.60×10 -3 g of a toluene solution of chloroplatinic acid / vinylsiloxane complex (containing 8.05×10 -9 mol of elemental Pt), and 3.15×(10 -3 g (5.25×10 -5 mol) of acetic acid were mixed and aged at 80 °C for 24 hours. Then, the solvent and unreacted substances were distilled off under reduced pressure to obtain 2.39 g of the product.

[0190] The obtained compound was 1 confirmed to have a structure represented by the following formula (F) by 1H-NMR.

[0191] [Synthesis Example 4] In a reaction vessel, 2.00 g (6.12×10 mol) of the compound represented by the following formula (E) obtained in the same manner as in Synthesis Example 3-2, 2.00 g of toluene, 1.26 g (6.43×10 -3 mol) of 3-mercaptopropyltrimethoxysilane, and 1.41×(10 -3 g (6.12×10 -1 mol) of 2,2'-azobis(isobutyric acid) dimethyl were mixed and aged at 75 °C for 3 hours. Then, the solvent and unreacted substances were distilled off under reduced pressure to obtain 3.10 g of the product. -4 mol) were mixed and aged at 75 °C for 3 hours. Then, the solvent and unreacted substances were distilled off under reduced pressure to obtain 3.10 g of the product.

[0192] The obtained compound was 1 confirmed to have a structure represented by the following formula (G) by 1H-NMR. -2 mol) of the compound represented by, 20.00 g of tetrahydrofuran, 5.00 g (3. <0g of 1-aminodecane -2 mol), and 4.82 g (4.77×10 -2 ​​​The mixture (mol) was aged at 25°C for 24 hours. After that, the solvent and unreacted materials were removed by vacuum distillation to obtain 9.66 g of product.

[0194] The resulting compound was 1 ¹H-NMR confirmed that the structure is represented by the following formula (I).

[0195] Synthesis Example 5-2 In the reaction vessel, the following formula (I) obtained in Synthesis Example 5-1 2.00 g (6.18 × 10) of the compound represented by -3 mol), toluene 2.00g, trimethoxysilane 3.78g (3.09 x 10) -2 mol), 2.60 × 10¹³ toluene solution of chloroplatinic acid / vinylsiloxane complex -3 g (8.05 × 10 as Pt alone) -9 (containing mol), and acetic acid 3.15 × 10 -3 g (5.25 x 10 -5 The mixture (mol) was aged at 80°C for 24 hours. After that, the solvent and unreacted materials were removed by vacuum distillation to obtain 2.64 g of product.

[0196] The resulting compound was 1 ¹H-NMR confirmed that the structure is represented by the following formula (J).

[0197] [Synthesis Example 6] In the reaction vessel, the following formula (I) obtained in the same manner as in Synthesis Example 5-1 2.00 g (6.18 × 10) of the compound represented by -3 mol), toluene 16.00g, 3-thiolpropyltrimethoxysilane 1.33g (6.80 x 10 -3 mol), and 2,2'-Azobis(isobutyrate)dimethyl 1.42 × 10 -1 g (6.18 x 10 -4 The mixture (mol) was aged at 75°C for 7 hours. After that, the solvent and unreacted materials were removed by vacuum distillation to obtain 3.04 g of product.

[0198] The resulting compound was 1 ¹H-NMR confirmed that the structure is represented by the following formula (K).

[0199] [Synthesis Example 7] Synthesis Example 7-1 In a reaction vessel, the following formula (L) 15.72 g of the compound represented by (4.89 × 10) -2 mol), dimethylformamide 100.00 g, tert-butyldimethylsilyl trifluoromethanesulfonate 19.40 g (7.34 x 10 -2 mol), and imidazole 5.33 g (7.83 x 10 -2 The mixture (mol) was combined and aged at 25°C for 2 hours. 200.00 g of pure water was added to the resulting solution and extracted three times with hexane. The combined organic layer was washed with pure water and saturated brine and dried over magnesium sulfate. The solvent and unreacted materials were then removed by vacuum distillation to obtain 20.45 g of product.

[0200] The resulting compound was 1 ¹H-NMR confirmed that the structure is represented by the following formula (M).

[0201] Synthesis Example 7-2 Put 10.09 g of 1-decanol (6.37 × 10) into the reaction vessel. -2 mol), tetrahydrofuran 60.00 g, tetrabutylammonium iodide 3.14 g (8.50 x 10 -3 mol), and potassium tert-butoxide 8.58 g (7.64 x 10) -2 The mixture (mol) was aged at 50°C for 1 hour. Then, the following formula (M) obtained in Synthesis Example 7-1 was prepared. 18.51 g (4.25 × 10) of the compound represented by this compound -2 A mol (unit of ammonium chloride) was added dropwise, and the mixture was aged at 25°C for 48 hours. 300.00 g of saturated ammonium chloride aqueous solution was added to the resulting solution, and the aqueous layer was extracted three times with ethyl acetate. The combined organic layers were washed with pure water and saturated brine, and dried over magnesium sulfate. The solvent and unreacted materials were then removed by reduced pressure distillation, and the recovered material was separated and purified by silica gel column chromatography to obtain 7.56 g of product.

[0202] The resulting compound was 1 ¹H-NMR confirmed that the structure is represented by the following formula (N).

[0203] Synthesis Example 7-3: In a reaction vessel, 7.56 g (1.47×10 mol) of the compound represented by the following formula (N) obtained in Synthesis Example 7-2, 20.00 g of tetrahydrofuran, and 19 mL of tetrabutylammonium fluoride (about 1 mol / L tetrahydrofuran solution) were mixed and aged at 25°C for 1 hour. 20.00 g of a saturated aqueous ammonium chloride solution was added to the obtained solution, and the mixture was extracted three times with ethyl acetate. The combined organic layers were washed with pure water and saturated brine, and dried over magnesium sulfate. Then, the solvent and unreacted substances were distilled off under reduced pressure, and the product was obtained by washing with methanol. 4.17 g of the product was obtained.

[0204] The obtained compound 1 was confirmed to have the structure represented by the following formula (O) by 1H-NMR.

[0205] Synthesis Example 7-4: In a reaction vessel, 4.17 g (1.05×10 mol) of the compound represented by the following formula (O) obtained in Synthesis Example 7-3, 5.00 g of toluene, 6.66×10 -2 g (6.28×10 -1 mol) of sodium carbonate, 7.05×10 -3 g (6.28×10 -2 mol) of chloro(1,5-cyclooctadiene)iridium(I) (dimer), and 1.81 g (2.10×10 -3 mol) of vinyl acetate were mixed and aged at 100°C for 72 hours. The obtained solution was filtered to remove inorganic salts, the solvent and unreacted substances were distilled off under reduced pressure, and the recovered product was separated and purified by silica gel column chromatography to obtain 3.30 g of the product.

[0206] The obtained compound 1 was confirmed to have the structure represented by the following formula (P) by 1H-NMR.

[0207] Synthesis Example 7-5: In a reaction vessel, 2.00 g (4.71×10 mol) of the compound represented by the following formula (P) obtained in Synthesis Example 7-4 -3 ​​​​mol), toluene 2.00g, trimethoxysilane 2.88g (2.35 x 10 -2 mol), 2.60 × 10¹³ toluene solution of chloroplatinic acid / vinylsiloxane complex -3 g (8.05 × 10 as Pt alone) -9 (containing mol), and acetic acid 3.15 × 10 -3 g (5.25 x 10 -5 The mixture (mol) was aged at 80°C for 24 hours. After that, the solvent and unreacted materials were removed by vacuum distillation to obtain 2.37 g of product.

[0208] The resulting compound was 1 ¹H-NMR confirmed that the structure is represented by the following formula (Q).

[0209] [Synthesis Example 8] In the reaction vessel, the following formula (R) 1.00 g (2.35 × 10) of the compound represented by -3 mol), toluene 5.00 g, 3-thiolpropyltrimethoxysilane 4.85 x 10 -1 g (2.47 × 10 -3 mol), and 2,2'-Azobis(isobutyrate)dimethyl 5.42 × 10 -2 g (2.35 x 10 -4 The mixture (mol) was aged at 75°C for 1 hour. Then, the solvent and unreacted materials were removed by vacuum distillation to obtain 1.40 g of the product.

[0210] The resulting compound was 1 ¹H-NMR confirmed that the structure is represented by the following formula (S).

[0211] [Synthesis Example 9] Synthesis Example 9-1 Put 10.75 g of 1-decanethiol (6.17 × 10) into a reaction vessel. -2 mol), toluene 25.00g, 10-undecen-1-ol 10.00g (5.87 x 10 -2 mol), and 1.35 g of 2,2'-azobis(isobutyrate)dimethyl (5.87 x 10⁻¹⁰) -3 The mixture (mol) was aged at 75°C for 1 hour. Then, the solvent and unreacted materials were removed by vacuum distillation to obtain 20.18 g of the product.

[0212] The resulting compound was 1 ¹H-NMR confirmed that the structure is represented by the following formula (T).

[0213] Synthesis Example 9-2 In the reaction vessel, the following formula (T) obtained in Synthesis Example 9-1 7.00 g (2.03 × 10) of the compound represented by -2 mol), tetrahydrofuran 35.00 g, tetrabutylammonium iodide 7.50 x 10 -1 g (2.03 × 10 -3 mol), and potassium tert-butoxide 3.42 g (3.05 x 10) -2 The mixture (mol) was added and aged at 50°C for 1 hour. Then, 4.19 g of allyl bromide (4.06 x 10) was added. -2 A mol (unit of ammonium chloride) was added dropwise, and the mixture was aged at 25°C for 24 hours. 50.00 g of saturated ammonium chloride aqueous solution was added to the resulting solution and separated, and the aqueous layer was extracted three times with ethyl acetate. The combined organic layers were washed with pure water and saturated brine, and dried over magnesium sulfate. Subsequently, the mixture was treated with activated carbon and Kyoward 500, and the solvent and unreacted materials were removed by vacuum distillation to obtain 6.31 g of product.

[0214] The resulting compound was 1 ¹H-NMR confirmed that the structure is represented by the following formula (U).

[0215] Synthesis Example 9-3 In the reaction vessel, the following formula (U) obtained in Synthesis Example 9-2 1.00 g (2.60 × 10) of the compound represented by -3 mol), toluene 5.00 g, trimethoxysilane 1.59 g (1.30 x 10 -2 mol), 2.60 × 10¹³ toluene solution of chloroplatinic acid / vinylsiloxane complex -3 g (8.05 × 10 as Pt alone) -9 (containing mol), and acetic acid 3.15 × 10 -3 g (5.25 x 10 -5 The mixture (mol) was aged at 80°C for 24 hours. After that, the solvent and unreacted materials were removed by vacuum distillation to obtain 1.27 g of the product.

[0216] The resulting compound was1 ¹H-NMR confirmed that the structure is represented by the following formula (V).

[0217] [Synthesis Example 10] In the reaction vessel, the following formula (U) obtained in the same manner as in Synthesis Example 9-2 1.00 g (2.60 × 10) of the compound represented by -3 mol), toluene 5.00g, 3-thiolpropyltrimethoxysilane 5.36 x 10 -1 g (2.73 x 10 -3 mol), and 2,2'-Azobis(isobutyrate)dimethyl 5.99 × 10 -2 g (2.60 x 10 -4 The mixture (mol) was aged at 75°C for 1 hour. Then, the solvent and unreacted materials were removed by vacuum distillation to obtain 1.47 g of product.

[0218] The resulting compound was 1 H-NMR confirmed that the structure is represented by the following formula (W).

[0219] [Synthesis Example 11] Synthesis Example 11-1 The following formula (A), obtained in the same manner as in Synthesis Example 1-1, was used in the reaction vessel. 5.00 g (1.61 × 10) of the compound represented by -2 mol), toluene 83.56 g, formula (X) below 38.72 g (1.61 × 10) of the compound represented by this expression. -1 mol), 2.60 × 10¹³ toluene solution of chloroplatinic acid / vinylsiloxane complex -3 g (8.05 × 10 as Pt alone) -9 (containing mol), and formamide 3.30 × 10 -3 g (7.33 × 10 -5 The mixture (mol) was aged at 80°C for 24 hours. After that, the solvent and unreacted materials were removed by vacuum distillation to obtain 8.52 g of the product.

[0220] The resulting compound was 1 H-NMR confirmed that the structure is represented by the following formula (Y).

[0221] Synthesis Example 11-2 In the reaction vessel, the following formula (Y) obtained in Synthesis Example 11-1 5.00 g (9.07 × 10) of the compound represented by -3 mol), toluene 5.00g, allyltrimethoxysilane 22.08g (1.36 x 10) -1 mol), 2.60 × 10¹³ toluene solution of chloroplatinic acid / vinylsiloxane complex -3 g (8.05 × 10 as Pt alone) -9 (containing mol), and acetic acid 3.15 × 10 -3 g (5.25 x 10 -5 The mixture (mol) was aged at 80°C for 24 hours. After that, the solvent and unreacted materials were removed by vacuum distillation to obtain 8.86 g of the product.

[0222] The resulting compound was 1 H-NMR confirmed that the structure is represented by the following formula (Z).

[0223] [Synthesis Example 12] Synthesis Example 12-1 The following formula (E), obtained in the same manner as in Synthesis Example 3-2, was used in the reaction vessel. 1.00 g (3.06 × 10) of the compound represented by -3 mol), toluene 2.00 g, trichlorosilane 11.17 g (8.25 x 10 -2 mol), 2.60 × 10¹³ toluene solution of chloroplatinic acid / vinylsiloxane complex -3 g (8.05 × 10 as Pt alone) -9 (containing mol), and acetic acid 3.15 × 10 -3 g (5.25 x 10 -5 The mixture (mol) was aged at 80°C for 24 hours. After that, the solvent and unreacted materials were removed by vacuum distillation to obtain 1.37 g of product.

[0224] The resulting compound was 1 ¹H-NMR confirmed that the structure is represented by the following formula (AA).

[0225] Synthesis Example 12-2 Add 1.45 g of bis(dimethylsilyl) ether (1.08 × 10⁻⁶) to the reaction vessel. -2(mol), 10.0 g of tetrahydrofuran, and 10.0 g of 1.2 M hydrochloric acid were mixed and stirred at 0 °C for 1 hour. Then, 1.00 g (2.16×10 mol) of the compound represented by the following formula (AA) obtained in Synthesis Example 12-1 was added dropwise over 1 hour while maintaining the internal temperature at 0 °C to 5 °C. After completion of the dropwise addition, the mixture was stirred at 0 °C for 2 hours. 50.00 g of pure water was added to the resulting solution, and the aqueous layer was extracted 3 times with toluene. The combined organic layers were washed with pure water and saturated brine, and dried over magnesium sulfate. Then, the solvent and unreacted substances were distilled off under reduced pressure to obtain 1.21 g of the product.

[0226] The obtained compound was 1 confirmed by 1H-NMR to have a structure represented by the following formula (AB).

[0227] Synthesis Example 12-3 In a reaction vessel, 1.00 g (1.72×10 mol) of the compound represented by the following formula (AB) obtained in Synthesis Example 12-2, 2.00 g of toluene, 3.16 g (1.55×10 -3 mol) of allyltriethoxysilane, 2.60×10 -2 g of a toluene solution of chloroplatinic acid / vinylsiloxane complex (containing 8.05×10 -3 mol of Pt as a simple substance), and 3.30×10 -9 g (7.33×10 -3 mol) of formamide were mixed and aged at 80 °C for 24 hours. Then, the solvent and unreacted substances were distilled off under reduced pressure to obtain 1.93 g of the product.

[0228] The obtained compound was 1 confirmed by 1H-NMR to have a structure represented by the following formula (AC).

[0229] [Synthesis Example 13] Synthesis Example 13-1 In a reaction vessel, 2.00 g (6.18×10 mol) of the compound represented by the following formula (I) obtained in the same manner as in Synthesis Example 5-1, 32.08 g of toluene, and the following formula (X) 14.87 g (6.18×10​​​​​​-2 mol), 2.60 × 10¹³ toluene solution of chloroplatinic acid / vinylsiloxane complex -3 g (8.05 × 10 as Pt alone) -9 (containing mol), and formamide 3.30 × 10 -3 g (7.33 × 10 -5 The mixture (mol) was aged at 80°C for 24 hours. After that, the solvent and unreacted materials were removed by vacuum distillation to obtain 3.21 g of product.

[0230] The resulting compound was 1 ¹H-NMR confirmed that the structure is represented by the following formula (AD).

[0231] Synthesis Example 13-2 In the reaction vessel, the following formula (AD) obtained in Synthesis Example 13-1 3.00 g (5.32 × 10) of the compound represented by -3 mol), toluene 5.00g, allyl glycidyl ether 9.11g (7.98 x 10 -2 mol), 2.60 × 10¹³ toluene solution of chloroplatinic acid / vinylsiloxane complex -3 g (8.05 × 10 as Pt alone) -9 (containing mol), and formamide 3.30 × 10 -3 g (7.33 × 10 -5 The mixture (mol) was aged at 80°C for 24 hours. After that, the solvent and unreacted materials were removed by reduced pressure distillation to obtain 4.37 g of product.

[0232] The resulting compound was 1 ¹H-NMR confirmed that the structure is represented by the following formula (AE).

[0233] [Synthesis Example 14] Synthesis Example 14-1 The following formula (U), obtained in the same manner as in Synthesis Example 9-2, was used in the reaction vessel. 3.00 g (7.80 x 10) of the compound represented by -3 mol), toluene 6.00g, trichlorosilane 1.16g (8.58 x 10) -3 mol), 2.60 × 10¹³ toluene solution of chloroplatinic acid / vinylsiloxane complex -3 g (8.05 × 10 as Pt alone) -9(containing mol), and formamide 3.30 × 10 -3 g (7.33 × 10 -5 The mixture (mol) was aged at 80°C for 24 hours. After that, the solvent and unreacted materials were removed by vacuum distillation to obtain 3.85 g of the product.

[0234] The resulting compound was 1 ¹H-NMR confirmed that the structure is represented by the following formula (AF).

[0235] Synthesis Example 14-2 In the reaction vessel, the following formula (AF) obtained in Synthesis Example 14-1 3.00 g of the compound represented by (5.77 × 10) -3 Mix mol) and 10.00 g of tetrahydrofuran and stir at 0°C. Then add 14.4 mL (2.88 × 10) of allyl magnesium chloride (2.0 M tetrahydrofuran solution). -2 A mol (hydrochloric acid) was added dropwise, and the mixture was aged at 25°C for 24 hours. 10.00 g of 2 M hydrochloric acid was added to the resulting solution, and the aqueous layer was extracted three times with toluene. The combined organic layers were washed with pure water and saturated brine, and dried over magnesium sulfate. Subsequently, the mixture was treated with activated carbon, and the solvent and unreacted materials were removed by vacuum distillation to obtain 2.48 g of product.

[0236] The resulting compound was 1 ¹H-NMR confirmed that the structure is represented by the following formula (AG).

[0237] Synthesis Example 14-3 In the reaction vessel, the following formula (AG) obtained in Synthesis Example 14-2 2.00 g (3.72 × 10) of the compound represented by -3 mol), toluene 4.00g, trimethoxysilane 6.83g (5.59 x 10 -2 mol), 2.60 × 10¹³ toluene solution of chloroplatinic acid / vinylsiloxane complex -3 g (8.05 × 10 as Pt alone) -9 (containing mol), and formamide 3.30 × 10 -3 g (7.33 × 10 -5 The mixture (mol) was aged at 80°C for 24 hours. After that, the solvent and unreacted materials were removed by reduced pressure distillation to obtain 3.23 g of product.

[0238] The resulting compound was 1 ¹H-NMR confirmed that the structure is represented by the following formula (AH).

[0239] [Synthesis Example 15] In the reaction vessel, the following formula (T) obtained in the same manner as in Synthesis Example 9-1 2.00 g (5.80 × 10) of the compound represented by -3 mol), tetrahydrofuran 10.00 g, 3-isocyanatepropyltrimethoxysilane 1.19 g (5.80 x 10 -3 mol), and tetrakis(2-ethylhexyl) orthotitanate 1.03 × 10 -2 g (1.82 × 10 -5 The mixture (mol) was aged at 50°C for 2 hours. After that, the solvent and unreacted materials were removed by vacuum distillation to obtain 2.93 g of the product.

[0240] The resulting compound was 1 1H-NMR confirmed that the structure is represented by the following formula (AI).

[0241] [Synthesis Example 16] Synthesis Example 16-1 The following formula (T) obtained in the same manner as in Synthesis Example 9-1 was used in the reaction vessel. 5.68 g of the compound represented by (1.65 × 10) -2 mol), tetrahydrofuran 45.00 g, tetrabutylammonium iodide 1.52 g (4.13 x 10 -3 mol), and potassium tert-butoxide 3.42 g (3.05 x 10) -2 The mixture (mol) was added and aged at 50°C for 1 hour. Then 5.00 g of 11-bromo-1-undecene (2.14 x 10) was added. -2 A mol of ammonium chloride was added dropwise, and the mixture was aged at 25°C for 24 hours. 100.00 g of saturated ammonium chloride aqueous solution was added to the resulting solution and separated, and the aqueous layer was extracted three times with ethyl acetate. The combined organic layers were washed with pure water and saturated brine, and dried over magnesium sulfate. After that, the mixture was treated with activated carbon, and the solvent and unreacted materials were removed by vacuum distillation to obtain 5.74 g of product.

[0242] The resulting compound was 1¹H-NMR confirmed that the structure is represented by the following formula (AJ).

[0243] Synthesis Example 16-2 In the reaction vessel, the following formula (AJ) obtained in Synthesis Example 16-1 2.00 g (4.02 × 10) of the compound represented by -3 mol), toluene 2.00 g, trimethoxysilane 2.46 g (2.01 x 10 -2 mol), 2.60 × 10¹³ toluene solution of chloroplatinic acid / vinylsiloxane complex -3 g (8.05 × 10 as Pt alone) -9 (containing mol), and formamide 3.30 × 10 -3 g (7.33 × 10 -5 The mixture (mol) was aged at 80°C for 24 hours. After that, the solvent and unreacted materials were removed by reduced pressure distillation to obtain 2.34 g of product.

[0244] The resulting compound was 1 ¹H-NMR confirmed that the structure is represented by the following formula (AK).

[0245] [Synthesis Example 17] In the reaction vessel, the following formula (AJ) obtained in the same manner as in Synthesis Example 16-1 2.00 g (4.02 × 10) of the compound represented by -3 mol), Toluene 20.00g, 3-thiolpropyltrimethoxysilane 8.30 x 10 -1 g (4.23 x 10 -3 mol), and 2,2'-Azobis(isobutyrate)dimethyl 9.26 × 10 -2 g (4.02 x 10 -4 The mixture (mol) was aged at 75°C for 3 hours. After that, the solvent and unreacted materials were removed by vacuum distillation to obtain 2.73 g of product.

[0246] The resulting compound was 1 ¹H-NMR confirmed that the structure is represented by the following formula (AL).

[0247] [Synthesis Example 18] Synthesis Example 18-1 The following formula (T), obtained in the same manner as in Synthesis Example 9-1, was used in the reaction vessel. 5.00 g (1.45 x 10) of the compound represented by -2 mol), tetrahydrofuran 50.00 g, tetrabutylammonium iodide 5.36 x 10 -1 g (1.45 x 10 -3 mol), and potassium tert-butoxide 2.44 g (2.18 x 10) -2 The mixture (mol) was added and aged at 50°C for 1 hour. Then, 4.84 g of ethyl bromoethyl (2.90 x 10) was added. -2 A mol (unit of volume) was added dropwise, and the mixture was aged at 50°C for 24 hours. 30.00 g of 2 M hydrochloric acid was added to the resulting solution, and the aqueous layer was extracted three times with toluene. The combined organic layers were washed with pure water and saturated brine, and dried over magnesium sulfate. Subsequently, the mixture was treated with activated carbon, and the solvent and unreacted materials were removed by vacuum distillation to obtain 5.12 g of product.

[0248] The resulting compound was 1 ¹H-NMR confirmed that the structure is represented by the following formula (AM).

[0249] Synthesis Example 18-2 In the reaction vessel, the following formula (AM) obtained in Synthesis Example 18-1 5.00 g (1.16 × 10) of the compound represented by -2 Mix mol) and 10.00 g of tetrahydrofuran and stir at 0°C. Then add 20.3 mL (4.06 × 10) of allyl magnesium chloride (2.0 M tetrahydrofuran solution). -2 A mol (unit of volume) was added dropwise, and the mixture was aged at 25°C for 24 hours. 30.00 g of 2 M hydrochloric acid was added to the resulting solution, and the aqueous layer was extracted three times with toluene. The combined organic layers were washed with pure water and saturated brine, and dried over magnesium sulfate. Subsequently, the mixture was treated with activated carbon, and the solvent and unreacted materials were removed by vacuum distillation to obtain 4.08 g of product.

[0250] The resulting compound was 1 ¹H-NMR confirmed that the structure is represented by the following formula (AN).

[0251] Synthesis Example 18-3 In the reaction vessel, the following formula (AN) obtained in Synthesis Example 18-2 2.00 g (4.27 × 10) of the compound represented by -3mol), toluene 2.00g, trimethoxysilane 5.21g (4.27 x 10) -2 mol), 2.60 × 10¹³ toluene solution of chloroplatinic acid / vinylsiloxane complex -3 g (8.05 × 10 as Pt alone) -9 (containing mol), and formamide 3.30 × 10 -3 g (7.33 × 10 -5 The mixture (mol) was aged at 80°C for 24 hours. After that, the solvent and unreacted materials were removed by vacuum distillation to obtain 2.86 g of the product.

[0252] The resulting compound was 1 ¹H-NMR confirmed that the structure is represented by the following formula (AO).

[0253] [Synthesis Example 19] In the reaction vessel, the following formula (AN) obtained in the same manner as in Synthesis Example 18-2 2.00 g (4.27 × 10) of the compound represented by -3 mol), toluene 20.00 g, 3-thiolpropyltrimethoxysilane 1.76 g (8.97 x 10 -3 mol), and 2,2'-Azobis(isobutyrate)dimethyl 1.96 × 10 -2 g (8.53 x 10 -4 The mixture (mol) was aged at 75°C for 3 hours. After that, the solvent and unreacted materials were removed by vacuum distillation to obtain 3.53 g of product.

[0254] The resulting compound was 1 ¹H-NMR confirmed that the structure is represented by the following formula (AP).

[0255] [Synthesis Example 20] Synthesis Example 20-1 Put 10.00 g of octyl isocyanate (6.44 x 10) into a reaction vessel. -2 mol), tetrahydrofuran 100.00 g, and 6-amino-1-hexanol 7.93 g (6.76 x 10) -2 The mixture (mol) was aged at 50°C for 1 hour. After that, the solvent was removed by vacuum distillation, and methanol washing was performed to obtain 16.52 g of the product.

[0256] The resulting compound was 1¹H-NMR confirmed that the structure is represented by the following formula (AQ).

[0257] Synthesis Example 20-2 In the reaction vessel, the following formula (AQ) obtained in Synthesis Example 20-1 10.00 g (3.67 × 10) of the compound represented by -2 mol), tetrahydrofuran 100.00 g, tetrabutylammonium iodide 2.71 g (7.34 x 10 -3 mol), and potassium tert-butoxide 4.94 g (4.40 x 10) -2 The mixture (mol) was aged at 50°C for 1 hour. Then, 12.84 g of 11-bromo-1-undecene (5.51 x 10) was added. -2 A mol (unit of volume) was added dropwise, and the mixture was aged at 50°C for 24 hours. 100.00 g of 2 M hydrochloric acid was added to the resulting solution, and the aqueous layer was extracted three times with toluene. The combined organic layers were washed with pure water and saturated brine, and dried over magnesium sulfate. Subsequently, the mixture was treated with activated carbon, and the solvent and unreacted materials were removed by vacuum distillation to obtain 12.47 g of product.

[0258] The resulting compound was 1 ¹H-NMR confirmed that the structure is represented by the following formula (AR).

[0259] Synthesis Example 20-3 In the reaction vessel, the following formula (AR) obtained in Synthesis Example 20-2 2.00 g of the compound represented by (4.71 × 10) -3 mol), toluene 2.00g, trimethoxysilane 2.88g (2.35 x 10 -2 mol), 2.60 × 10¹³ toluene solution of chloroplatinic acid / vinylsiloxane complex -3 g (8.05 × 10 as Pt alone) -9 (containing mol), and formamide 3.30 × 10 -3 g (7.33 × 10 -5 The mixture (mol) was aged at 80°C for 24 hours. After that, the solvent and unreacted materials were removed by reduced pressure distillation to obtain 2.42 g of product.

[0260] The resulting compound was 1 ¹H-NMR confirmed that the structure is represented by the following formula (AS).

[0261] [Synthesis Example 21] In the reaction vessel, the following formula (AR) obtained in the same manner as in Synthesis Example 20-2 2.00 g of the compound represented by (4.71 × 10) -3 mol), Toluene 20.00g, 3-thiolpropyltrimethoxysilane 9.71 x 10 -1 g (4.95 x 10 -3 mol), and 2,2'-Azobis(isobutyrate)dimethyl 1.08 × 10 -1 g (4.71 x 10 -4 The mixture (mol) was aged at 75°C for 3 hours. After that, the solvent and unreacted materials were removed by vacuum distillation to obtain 2.84 g of product.

[0262] The resulting compound was 1 H-NMR confirmed that the structure is represented by the following formula (AT).

[0263] Solubility Evaluation The solubility of the compounds synthesized in the above synthesis examples (final compounds) and comparative compounds 1 to 4 below was evaluated. Specifically, each compound and the solvents shown in Table 1 were placed in vials so that each compound was present at 30% by mass, and the mixture was stirred. The vials were kept at 25°C, and the solubility was evaluated according to the evaluation criteria below. Only propylene glycol methyl ether (hereinafter PGME) was prepared so that each compound was present at 0.2% by mass. The results are shown in Table 1. [Solubility Evaluation Criteria] ○: Dissolves completely and becomes a clear liquid △: Dissolves completely after stirring, but precipitate forms over time ×: The synthesized compound remains undissolved and precipitate is observed

[0264] [Comparative Compound 1] Compound represented by the following formula (A')

[0265] [Comparative Compound 2] Compound represented by the following formula (B')

[0266] [Comparative Compound 3] Compound represented by the following formula (C')

[0267] [Comparative Compound 4] Compound represented by the following formula (D')

[0268]

[0269] The compounds obtained in Synthesis Examples 1 (Synthesis Examples 1-2) to 21, as described in Table 1 above, exhibited good solubility in a wide range of solvents, from highly polar acetone to PGME, dibutyl ether, and even less polar toluene. Therefore, the hydrocarbon-end group-containing compounds of the present invention have fewer solvent restrictions when producing cured films, and a wide range of solvents can be used. Furthermore, because they dissolve in low-volatility solvents, the drying process after coating can be shortened. In addition, safer solvents can be selected and used, reducing the environmental burden.

[0270] [Examples 1-15, Comparative Examples 1-4] Preparation of surface treatment agents and formation of cured films The compounds (final compounds) obtained in the synthesis examples shown in Table 2 below and comparative compounds were dissolved in PGME so that each compound was present in an amount of 0.2% by mass to prepare surface treatment agents. Each surface treatment agent was spray-coated onto glass (Corning Gorilla) with a 10 nm thick layer of SiO2 on its outermost surface, and cured for 1 hour at 80°C and 80% relative humidity, and then for 12 hours at 25°C and 50% relative humidity to form a cured film with a thickness of 3-5 nm.

[0271] The water repellency and abrasion resistance of the glass with a hardened coating were evaluated using the method described below.

[0272] Evaluation of Water Repellency: The contact angle (water repellency) of the hardened film formed on the glass prepared as described above was measured using a Drop Master contact angle meter (manufactured by Kyowa Interface Science Co., Ltd.) (droplet: 2 μl, temperature: 25°C, relative humidity: 40%). A contact angle (water repellency) of 85° or higher was considered good. The results (water contact angle) are shown in Table 2.

[0273] Abrasion Resistance Evaluation The glass with the hardened coating prepared as described above was rubbed every 500 times using a rubbing tester (manufactured by Shinto Kagaku Co., Ltd.) under the following conditions. The contact angle (water repellency) of the hardened coating with water was measured in the same manner as described above, and the number of times the contact angle fell below 80° was recorded to evaluate abrasion resistance. The test environment conditions were 25°C and 40% relative humidity. A result of 2,000 or more times the contact angle fell below 80° was considered good. The results (number of times the water contact angle fell below 80°) are shown in Table 2. [Steel Wool Abrasion Resistance Test Conditions] Steel wool: Bonster #0000 Contact area: 1 cm 2 Distance traveled (one way): 40 mm; Speed: 4,800 mm / min; Load: 500 gf / cm 2

[0274]

[0275] The cured coatings of the surface treatment agents in Examples 1 to 15, using the compounds obtained in Synthesis Example 1 (Synthesis Example 1-2) to Synthesis Example 21 as described in Table 2 above, exhibited water repellency because the mobility of the molecular chain was improved by having a monovalent hydrocarbon group with a specific number of carbon atoms via a linking group. Furthermore, the presence of 1 to 3 linking functional groups in the molecular chain of the compound used improved intermolecular interactions and molecular mobility, resulting in good abrasion resistance. Moreover, the compounds obtained in Synthesis Example 1 (Synthesis Example 1-2) to Synthesis Example 21 as described in Table 2 above dissolve well in PGME, suggesting that the compounds adhered sufficiently to the substrate during spray coating, resulting in excellent water repellency and abrasion resistance. The cured coating of the surface treatment agent in Comparative Example 1, using Comparative Compound 1, exhibited water repellency due to the presence of a hydrocarbon chain with 18 carbon atoms at the end of the molecular chain of the compound used, but the abrasion resistance was inferior because the molecular chain of the compound used did not contain a linking functional group. The cured film of the surface treatment agent in Comparative Example 2, using comparative compound 2, exhibited high water repellency due to the presence of fluorinated hydrocarbon chains at the molecular chain ends of the compound used. However, it showed poor abrasion resistance because the molecular chain of the compound used did not contain linking functional groups. Comparative compounds 3 and 4 were insoluble in PGME, and therefore, surface treatment agents and cured films for Comparative Examples 3 and 4 could not be obtained. As described above, the surface treatment agents in the examples were able to produce a cured film that achieved a high level of both water repellency and abrasion resistance in spray coating.

[0276] [Examples 16-32, Comparative Examples 5-8] Preparation of surface treatment agents and formation of cured films The compounds (final compounds) obtained in the synthesis examples shown in Table 3 below and comparative compounds were dissolved in PGME so that each compound was present in 30% by mass to prepare surface treatment agents. Each surface treatment agent was vacuum deposited onto glass (Corning Gorilla) coated with SiO2 to a thickness of 10 nm on the outermost surface (processing conditions: pressure: 2.0 × 10⁻⁶). -2 A cured film with a thickness of 3-5 nm was formed by curing in an atmosphere of Pa, heating temperature: 700°C, 80°C, and relative humidity for 1 hour, and then in an atmosphere of 25°C and relative humidity for 12 hours.

[0277] The water repellency and abrasion resistance of the glass with a hardened coating were evaluated using the method described below.

[0278] Evaluation of Water Repellency The contact angle (water repellency) of the hardened film formed on the glass prepared as described above was measured using a Drop Master contact angle meter (manufactured by Kyowa Interface Science Co., Ltd.) (droplet: 2 μl, temperature: 25°C, relative humidity: 40%). A contact angle (water repellency) of 85° or higher was considered good. The results (water contact angle) are shown in Table 3.

[0279] Abrasion Resistance Evaluation The glass with the hardened coating prepared as described above was rubbed every 500 times using a rubbing tester (manufactured by Shinto Kagaku Co., Ltd.) under the following conditions. The contact angle (water repellency) of the hardened coating with water was measured in the same manner as described above, and the number of times the contact angle fell below 80° was recorded to evaluate abrasion resistance. The test environment conditions were 25°C and 40% relative humidity. A result of 2,000 or more times the contact angle fell below 80° was considered good. The results (number of times the water contact angle fell below 80°) are shown in Table 3. [Steel Wool Abrasion Resistance Test Conditions] Steel wool: Bonster #0000 Contact area: 1 cm 2 Distance traveled (one way): 40 mm; Speed: 4,800 mm / min; Load: 500 gf / cm 2

[0280]

[0281] The cured coatings of the surface treatment agents in Examples 16 to 32, using the compounds obtained in Synthesis Example 1 (Synthesis Example 1-2) to Synthesis Example 20 (Synthesis Example 20-3) as described in Table 3 above, exhibited water repellency because the mobility of the molecular chain was improved by having a monovalent hydrocarbon group with a specific number of carbon atoms via a linking group. Furthermore, the presence of 1 to 3 linking functional groups in the molecular chain of the compound used improved intermolecular interactions and molecular mobility, resulting in good abrasion resistance. Moreover, the compounds obtained in Synthesis Example 1 (Synthesis Example 1-2) to Synthesis Example 20 (Synthesis Example 20-3) as described in Table 3 above dissolve well in PGME, suggesting that the compounds adhered sufficiently to the substrate during vapor deposition coating, resulting in excellent water repellency and abrasion resistance. The cured coating of the surface treatment agent in Comparative Example 5, using Comparative Compound 1, exhibited water repellency due to the presence of a hydrocarbon chain with 18 carbon atoms at the end of the molecular chain of the compound used, but the lack of a linking functional group in the molecular chain of the compound used resulted in poor abrasion resistance. The cured film of the surface treatment agent in Comparative Example 6, using comparative compound 2, exhibited high water repellency due to the presence of fluorinated hydrocarbon chains at the molecular chain ends of the compound used. However, it showed poor abrasion resistance because the molecular chain of the compound used did not contain linking functional groups. Comparative compounds 3 and 4 were insoluble in PGME, and therefore, surface treatment agents and cured films for Comparative Examples 7 and 8 could not be obtained. As described above, the surface treatment agents in the examples were able to produce cured films that achieved a high level of both water repellency and abrasion resistance, even in vapor deposition coating.

Claims

1. The following general formula (1) A hydrocarbon terminal group-containing compound represented by the formula: (wherein R is a monovalent hydrocarbon group having 1 to 10 carbon atoms, Z is a divalent linking functional group independently comprising at least one selected from an oxygen atom, a nitrogen atom, a sulfur atom, and a silicon atom, Y is independently a divalent hydrocarbon group having 1 to 30 carbon atoms, W is a single bond, a carbon atom, a silicon atom, a nitrogen atom, or a 3 to 5 valent organic group, A is a monovalent reactive group, k1 is an integer from 1 to 3, k2 is an integer from 1 to 4, k3 is 0 or 1, and k4 is 0 or 1.) 2. In the above formula (1), A is a cyclic ether group, and the following general formula (2) (In the formula, R 1 ) is an alkyl group or phenyl group having 1 to 4 carbon atoms independently, X is an alkyl group or hydrolyzable group independently, and n is an integer from 1 to 3. ) A hydroxyl group-containing silyl group or hydrolyzable silyl group represented by the following general formula (3) The hydrocarbon terminal group-containing compound according to claim 1, wherein the silazane group is represented by (wherein n'' is a number from 0 to 3, and n' is (3 - n'') / 2).

3. The hydrocarbon terminal group-containing compound according to claim 2, wherein in formula (2) above, X is selected from the group consisting of a hydroxyl group, an alkoxy group having 1 to 10 carbon atoms, an alkoxyalkoxy 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 group, and a dialkylamino group having 2 to 10 carbon atoms.

4. The hydrocarbon terminal group-containing compound according to claim 1, wherein R in formula (1) above is a monovalent hydrocarbon group having 3 to 10 carbon atoms, which may be linear, branched, cyclic, or a combination thereof.

5. The hydrocarbon terminal group-containing compound according to claim 1, wherein Z is independently a divalent group selected from ether group, carbonyl (ketone) group, ester group, carbonate group, thioether group, sulfinyl group, sulfonyl group, thioester group, thiocarbonate group, thiocarbamate group, amino group, amide group, carbamate group, urea group, divalent nitrogen-containing heterocyclic group, diorganosilylene group, and divalent organopolysiloxane residues having 2 to 10 silicon atoms in a linear chain or 3 to 10 silicon atoms in a branched or cyclic configuration.

6. In the above equation (1), Y independently gives the following general equation (4) (In the formula, R 2 R is an independent monovalent hydrocarbon group having 1 to 10 carbon atoms. 3 A is a divalent cyclic hydrocarbon group having 3 to 9 carbon atoms, which may independently have substituents. a is an integer from 0 to 30, b is an integer from 0 to 15, c is an integer from 0 to 10, and d is an integer from 0 to 6, and the sum of a, b, c, and d is an integer such that the sum of carbon atoms in formula (4) is from 1 to 30. Each repeating unit shown in the parentheses with a, b, c, and d may be randomly bonded.) The hydrocarbon terminal group-containing compound according to claim 1, which is a group represented by ).

7. In formula (1) above, W is a single bond, a carbon atom, a silicon atom, a nitrogen atom, a trivalent or tetravalent cyclic hydrocarbon group having 6 to 8 carbon atoms, -SiR 8 = (R 8 (A trivalent group represented by a hydroxyl group, an alkyl group having 1 to 3 carbon atoms, or an alkoxy group having 1 to 3 carbon atoms), -CR 9 = (R 9 The hydrocarbon terminal group-containing compound according to claim 1, wherein the group is a trivalent group (represented by a hydrogen atom, a hydroxyl group, or an alkyl group having 1 to 3 carbon atoms), a linear or branched or cyclic trivalent to pentavalent organopolysiloxane residue having 2 to 10 silicon atoms, a trivalent amide group, a trivalent carbamate group, a trivalent or tetravalent urea group, and a trivalent or tetravalent nitrogen-containing heterocyclic group.

8. In the above formula (1), k1 is 1, and R is the following general formula (5) (wherein, R 4 is a methyl group, a cyclic alkyl group or a phenyl group. R 3 is independently a divalent cyclic hydrocarbon group having 3 to 9 carbon atoms which may have a substituent. y is an integer of 0 or more, h is an integer of 0 to 3, and the sum of y and h is an integer such that the total number of carbon atoms in formula (5) is 10 or less. Each repeating unit shown in parentheses with y and h attached may be randomly bonded.) is a monovalent hydrocarbon group represented by the hydrocarbon terminal group-containing compound according to claim 1.

9. The hydrocarbon terminal group-containing compound according to claim 1, wherein k1 is 2 or 3 in formula (1) above.

10. A surface treatment agent comprising a hydrocarbon terminal group-containing compound according to any one of claims 1 to 9.

11. An article surface-treated with the surface treatment agent described in claim 10.

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