Novel compound

Abstract

To provide a novel zwitterionic monomer, and a novel compound serving as an ingredient for producing the novel zwitterionic monomer.SOLUTION: The invention provides a compound represented by the formula (1), R1-(O)p-(CH2)m-(OR2)n-NR3R4, and a compound represented by the formula (2), R5-(O)q-(CH2)r-(OR6)S-N+R7R8-(CH2)t-X, where details of the formulas (1) and (2) are described in the specification.SELECTED DRAWING: None

Description

[Technical field]

[0001] The present disclosure relates to novel compounds. [Background technology]

[0002] Zwitterionic polymers are polymers that contain both anionic and cationic groups in one molecule. In recent years, zwitterionic polymers are expected to be used in a variety of fields.

[0003] For example, Non-Patent Document 1 describes a zwitterionic polymer composed of zwitterionic monomers having a (meth)acrylic acid ester and a metha(acryl)amide structure. [Prior art documents] [Non-patent literature]

[0004] [Non-Patent Document 1] Polymer, 2009, Vol. 58, February, pp. 74-77 Summary of the Invention [Problem to be solved by the invention]

[0005] An object of the present invention is to provide a novel zwitterionic monomer and a novel compound that can be used as a raw material for producing the novel zwitterionic monomer. [Means for solving the problem]

[0006] Specific means for solving the above problems include the following aspects. <1> A compound represented by the following formula (1): R 1 -(O) p -(CH 2 ) m -(OR 2 ) n -NR 3 R 4 (1) In formula (1), R 1 is CH2 =CH-, CH 2 =CHCH 2 - or CH 3 CH=CH-, R 2 are each independently -CH 2 CH 2 -, -CH 2 CH 2 CH 2 -or-CH 2 CH(CH 3 )-, R 3 and R 4 each independently represents an alkyl group having 1 to 6 carbon atoms, p represents 0 or 1, m represents an integer of 0 to 4, and n represents an integer of 1 to 3, provided that when m is 0, p is 0. <2> In formula (1), R 1 is CH 2 =CH- and R 2 Ha-CH 2 CH 2 -It is <1> The compound according to claim 1, <3> A compound represented by the following formula (2): R 5 -(O) q -(CH 2 ) r -(OR 6 ) S -N + R 7 R 8 -(CH 2 ) t -X (2) In formula (2), R 5 is CH 2 =CH-, CH 2 =CHCH 2 - or CH 3 CH=CH-, R 6 are each independently -CH 2 CH 2 -, -CH 2 CH 2 CH 2 -or-CH 2 CH(CH 3 )-, R 7 and R 8each independently represents an alkyl group having 1 to 6 carbon atoms, q represents 0 or 1, r represents an integer of 0 to 4, s represents an integer of 1 to 3, t represents an integer of 1 to 4, and X is SO 3 - or CO 2 - However, if r is 0, then q is 0. <4> In formula (2), R 5 is CH 2 =CH- and R 6 Ha-CH 2 CH 2 -It is <3> The compound according to claim 1, Effect of the Invention

[0007] According to the present invention, there are provided novel zwitterionic monomers and novel compounds that serve as raw materials for producing the novel zwitterionic monomers. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0008] The novel compound of the present invention will be described in detail below.

[0009] In this specification, a numerical range indicated using "to" means a range that includes the numerical values ​​before and after "to" as the minimum and maximum values, respectively. In the numerical ranges described in this specification, the upper or lower limit value described in a certain numerical range may be replaced with the upper or lower limit value of another numerical range described in a certain numerical range. In addition, in the numerical ranges described in this specification, the upper or lower limit value described in a certain numerical range may be replaced with a value shown in the examples.

[0010] In this specification, the amount of each component in a composition means the total amount of the multiple substances present in the composition when multiple substances corresponding to each component are present in the composition, unless otherwise specified. As used herein, a combination of two or more preferred embodiments is a more preferred embodiment. In this specification, the term "process" includes not only an independent process but also a process that cannot be clearly distinguished from other processes, as long as the intended purpose of the process is achieved.

[0011] [Compound represented by formula (1)] The compound of the present disclosure is a compound represented by the following formula (1).

[0012] R 1 -(O) p -(CH 2 ) m -(OR 2 ) n -NR 3 R 4 (1)

[0013] In formula (1), R 1 is CH 2 =CH-, CH 2 =CHCH 2 - or CH 3 It stands for CH=CH-. 2 are each independently -CH 2 CH 2 -, -CH 2 CH 2 CH 2 -or-CH 2 CH(CH 3 )-. R 3 and R 4 each independently represents an alkyl group having 1 to 6 carbon atoms. p represents 0 or 1, m represents an integer of 0 to 4, and n represents an integer of 1 to 3. However, when m is 0, p is 0.

[0014] Examples of the compound represented by formula (1) include the following compounds.

[0015] CH 2 =CH-OCH 2 CH 2 -N(CH 3 ) 2 CH 2 =CH-(OCH 2 CH 2 )2 -N(CH 3 ) 2 CH 2 =CH-(OCH 2 CH 2 ) 2 -N(CH 2 CH 3 ) 2 CH 2 =CH-(OCH 2 CH 2 CH 2 ) 2 -N(CH 3 ) 2 CH 2 =CH-(OCH 2 CH(CH 3 )) 2 -N(CH 3 ) 2 CH 2 =CH-(CH 2 ) 2 -(AND 2 CH 2 ) 2 -N(CH 3 ) 2 CH 2 =CH-(CH 2 ) 4 -(AND 2 CH 2 ) 2 -N(CH 3 ) 2 CH 2 =CH-O-(CH 2 ) 2 -(AND 2 CH 2 ) 2 -N(CH 3 ) 2 CH 2 =CHCH 2 -(AND 2 CH 2 ) 2 -N(CH 3 ) 2 CH 3 CH=CH-(OCH2 CH 2 ) 2 -N(CH 3 ) 2

[0016] Among them, in formula (1), R 1 is CH 2 =CH- and R 2 Ha-CH 2 CH 2 - is preferred.

[0017] In addition, in formula (1), R 3 and R 4 The alkyl group having 1 to 6 carbon atoms represented by the formula (I) may be a linear alkyl group, a branched alkyl group, or a cyclic alkyl group. Examples of the alkyl group having 1 to 6 carbon atoms include a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, a t-butyl group, a pentyl group, and a hexyl group. Among them, R 3 and R 4 are each independently preferably an alkyl group having 1 to 3 carbon atoms, and more preferably a methyl group or an ethyl group.

[0018] The method for producing the compound represented by formula (1) is not particularly limited. The compound represented by formula (1) can be produced, for example, by the following method.

[0019] A method for producing a compound represented by formula (1) includes, for example, step A of obtaining a reaction solution by reacting a compound represented by the following formula (11) with a base, and step B of mixing the reaction solution with a compound represented by the following formula (12). H(OR 2 ) n -NR 3 R 4 (11) R 1 -(O) p -(CH 2 ) m R 10 (12)

[0020] In step A, a compound represented by formula (11) is reacted with a base. 2 , R 3 , R 4 and n is R in formula (1). 2 , R 3 , R 4 and n are the same as R in formula (12). 1 , p and m are R in formula (1). 1 , p and m. R 10 represents a halogen atom, preferably a chlorine atom or a bromine atom, and more preferably a chlorine atom.

[0021] Examples of the compound represented by formula (11) include the following compounds. H(OCH 2 CH 2 ) 2 -N(CH 3 ) 2 H(OCH 2 CH 2 ) 2 -N(CH 2 CH 3 ) 2 HOCH 2 CH 2 -N(CH 3 ) 2 H(OCH 2 CH 2 CH 2 ) 2 -N(CH 3 ) 2 H(OCH 2 CH(CH 3 )) 2 -N(CH 3 ) 2

[0022] Examples of the compound represented by formula (12) include the following compounds. CH 2 =CH-(CH 2 ) 2 -Cl CH 2 =CH-(CH2 ) 4 -Cl CH 2 =CH-O-(CH 2 ) 2 -Cl CH 2 =CHCH 2 -Cl CH 3 CH=CH-Cl

[0023] In addition, in the compound represented by formula (1), when n is 1, that is, R 1 -(O) p -(CH 2 ) m -OR 2 -NR 3 R 4 It can also be produced by the following method.

[0024] R 1 -(O) p -(CH 2 ) m -OR 2 -NR 3 R 4 The production method of includes, for example, a step C of obtaining a reaction solution by reacting a compound represented by the following formula (13) with a base, and a step D of mixing the reaction solution with a compound represented by the following formula (14). R 1 -(O) p -(CH 2 ) m OH (13) R 20 R 2 -NR 3 R 4 (14)

[0025] In step C, the compound represented by formula (13) is reacted with a base. 1 , p and m are R in formula (1). 1 , p and m are the same as those in formula (14). 2 , R 3 and R 4 is R in formula (1). 2 , R 3 and R 4is the same as R 20 represents a halogen atom, preferably a chlorine atom or a bromine atom, and more preferably a chlorine atom.

[0026] Examples of the compound represented by formula (13) include the following compounds. CH 2 =CH-(CH 2 ) 2 -OH CH 2 =CH-(CH 2 ) 4 -OH CH 2 =CH-O-(CH 2 ) 2 -OH CH 2 =CHCH 2 -OH CH 3 CH=CH-OH

[0027] Examples of the compound represented by formula (14) include the following compounds. ClCH 2 CH 2 -N(CH 3 ) 2 ClCH 2 CH 2 -N(CH 2 CH 3 ) 2 ClCH 2 CH 2 CH 2 -N(CH 3 ) 2 ClCH 2 CH(CH 3 )-N(CH 3 ) 2

[0028] The type of base is not particularly limited, but is preferably sodium hydroxide or potassium hydroxide. The type of solvent is not particularly limited, and can be appropriately selected depending on the type of compound represented by formula (11). Examples of the solvent include aliphatic hydrocarbons, aromatic hydrocarbons, halogenated hydrocarbons, alcohols, ketones, esters, and ethers. The reaction temperature in step A is preferably 105°C to 130°C.

[0029] In step B, the reaction solution obtained in step A is mixed with a compound represented by formula (12). 1 , m and p are R in formula (1). 1 , m and p.

[0030] In formula (12), R 10 is a halogen, preferably Cl or Br, and more preferably Cl.

[0031] The reaction temperature in step B is preferably 70°C to 100°C.

[0032] [Compound represented by formula (2)] The compound of the present disclosure is a compound represented by the following formula (2).

[0033] R 5 -(O) q -(CH 2 ) r -(OR 6 ) S -N + R 7 R 8 -(CH 2 ) t -X (2)

[0034] In formula (2), R 5 is CH 2 =CH-, CH 2 =CHCH 2 - or CH 3 It stands for CH=CH-. 6 are each independently -CH 2 CH2 -, -CH 2 CH 2 CH 2 -or-CH 2 CH(CH 3 )-. R 7 and R 8 each independently represents an alkyl group having 1 to 6 carbon atoms, q represents 0 or 1, r represents an integer of 0 to 4, s represents an integer of 1 to 3, and t represents an integer of 1 to 4. X is SO 3 - or CO 2 - However, if r is 0, then q is 0.

[0035] Examples of the compound represented by formula (2) include the following compounds.

[0036] CH 2 =CH-OCH 2 CH 2 -N + (CH 3 ) 2 -(CH 2 ) 3 -SO 3 - CH 2 =CH-(OCH 2 CH 2 ) 2 -N + (CH 3 ) 2 -CH 2 -SO 3 - CH 2 =CH-(OCH 2 CH 2 ) 2 -N + (CH 3 ) 2 -(CH 2 ) 3 -SO 3 - CH 2 =CH-(OCH 2 CH 2 ) 2 -N + (CH3 ) 2 -(CH 2 ) 3 -CO 2 - CH 2 =CH-(OCH 2 CH 2 ) 2 -N + (CH 2 CH 3 ) 2 -(CH 2 ) 3 -SO 3 - CH 2 =CH-(OCH 2 CH 2 CH 2 ) 2 -N + (CH 3 ) 2 -(CH 2 ) 3 -SO 3 - CH 2 =CH-(OCH 2 CH(CH 3 )) 2 -N + (CH 3 ) 2 -(CH 2 ) 3 -SO 3 - CH 2 =CH-(CH 2 ) 2 -(OCH 2 CH 2 ) 2 -N + (CH 3 ) 2 -(CH 2 ) 3 -SO 3 - CH 2 =CH-(CH 2 ) 4 -(OCH 2 CH 2 ) 2 -N+ (CH 3 ) 2 -(CH 2 ) 3 -SO 3 - CH 2 =CH-O-(CH 2 ) 2 -(OCH 2 CH 2 ) 2 -N + (CH 3 ) 2 -(CH 2 ) 3 -SO 3 - CH 2 =CHCH 2 -(OCH 2 CH 2 ) 2 -N + (CH 3 ) 2 -(CH 2 ) 3 -SO 3 - CH 3 CH=CH-(OCH 2 CH 2 ) 2 -N + (CH 3 ) 2 -(CH 2 ) 3 -SO 3 -

[0037] Among them, in formula (2), R 5 is CH 2 =CH- and R 6 Ha-CH 2 CH 2 - is preferred.

[0038] In addition, in formula (2), R 7 and R 8The alkyl group having 1 to 6 carbon atoms represented by the formula (I) may be a linear alkyl group, a branched alkyl group, or a cyclic alkyl group. Examples of the alkyl group having 1 to 6 carbon atoms include a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, a t-butyl group, a pentyl group, and a hexyl group. Among them, R 7 and R 8 are each independently preferably an alkyl group having 1 to 3 carbon atoms, and more preferably a methyl group or an ethyl group.

[0039] In addition, in formula (2), t is preferably 3 or 4 from the viewpoint of ease of production.

[0040] The method for producing the compound represented by formula (2) is not particularly limited. In formula (2), t is 3 and X is SO 3 - The manufacturing method will be described taking the above case as an example.

[0041] The compound represented by formula (2) can be produced, for example, by reacting the compound represented by formula (1) with 1,3-propane sultone. First, the compound represented by formula (1) is dissolved in a solvent. The type of solvent may be appropriately selected depending on the type of the compound represented by formula (1) and is not particularly limited, but an anhydrous solvent is preferable. The reaction is also preferably carried out under an inert gas atmosphere. Examples of the inert gas include nitrogen and argon. Next, 1,3-propane sultone is added to the solution of the compound represented by formula (1). This results in the formation of R 5 -(O) q -(CH 2 ) r -(OR 6 ) S -N + R 7 R 8 -(CH 2 ) 3 -SO 3 - is obtained.

[0042] In formula (2), t is 4 and X is SO3 - The compound represented by the formula (2) can be produced by the same method as above, except that 1,4-butane sultone or the like is used instead of 1,3-propane sultone. 2 - The compound represented by the formula (I) can be produced by a method similar to the above-mentioned production method, except that a lactone compound such as β-propiolactone, γ-butyrolactone, or δ-valerolactone is used in place of a sultone compound such as 1,3-propane sultone.

[0043] The compound represented by formula (2) does not have a carbonyl group, and is therefore considered to be more resistant to hydrolysis and more stable than conventional zwitterionic monomers having a (meth)acrylic acid ester or (meth)acrylamide structure. In addition, the compound represented by formula (2) is considered to be more resistant to self-polymerization and more stable.

[0044] The compound represented by formula (2) is advantageous because it is highly soluble and various solvents can be used in its preparation.

[0045] The compound represented by formula (1) is suitable for producing the compound represented by formula (2), and the compound represented by formula (2) can be easily produced.

[0046] The compound represented by formula (1) is R 1 But, CH 2 =CH-, CH 2 =CHCH 2 - or CH 3 CH=CH-, and the compound represented by formula (2) is R 5 But, CH 2 =CH-, CH 2 =CHCH 2 - or CH 3CH=CH-. Therefore, since the compound represented by formula (1) and the compound represented by formula (2) have a polymerizable group, a novel polymer can be produced by using the compound represented by formula (1) and the compound represented by formula (2). In particular, a novel zwitterionic polymer can be produced by using the compound represented by formula (2). The compound represented by formula (1) and the compound represented by formula (2) are expected to be applied to applications such as inks, coating agents, adhesives, and medical materials. EXAMPLES

[0047] Hereinafter, the present disclosure will be described more specifically with reference to examples. However, the present disclosure is not limited to the following examples as long as it does not depart from the gist of the disclosure.

[0048] Example 1 <CH 2 =CH-(OCH 2 CH 2 ) 2 -N(CH 3 ) 2 Synthesis of > 50.2 g of toluene, 25.4 g (284 mmol) of 2-(dimethylamino)ethanol, and 85.5 g (1,470 mmol, 5.0 equivalents) of sodium hydroxide were added to a 500 mL four-neck flask and refluxed for 90 minutes. After that, it was cooled to 100°C, and 60.2 g (565 mmol, 1.9 equivalents) of 2-chloroethyl vinyl ether was added dropwise over 22 hours. After stirring at 95°C for 24 hours, 253.2 g of water and 172.1 g of toluene were added, and a separation operation was performed to separate the toluene layer. 157.2 g of toluene was added to the water layer, and a separation operation was performed to separate the toluene layer. The two toluene layers were combined, and then 22.2 g of anhydrous sodium sulfate was added and dried.

[0049] After filtering off the anhydrous sodium sulfate, the mixture was concentrated under reduced pressure to obtain 9.9 g of a crude product, which was then distilled under reduced pressure to obtain 4.8 g (yield: 11%) of the desired product, 2-(dimethylamino)ethoxyethyl vinyl ether, with a purity of 98%.

[0050] CH 2 =CH-(OCH 2 CH 2 ) 2 -N(CH 3 ) 2 The structure was confirmed by the following NMR data.

[0051] [ka]

[0052] [Table 1]

[0053] Example 2 50 mL of toluene, 17.1 g (194 mmol, 1.9 equivalents), 22.2 g (376 mmol, 3.8 equivalents) of 95% potassium hydroxide were added to a 200 mL four-neck flask, and 14.4 g (100 mmol) of 2-(dimethylamino)ethyl chloride hydrochloride was added and refluxed for 4 hours. After cooling to room temperature, 60 mL of water was added, and a separation operation was performed to separate the toluene layer. The toluene layer was washed with 40 mL of water and then concentrated under reduced pressure to obtain 17.3 g of crude product. Distillation under reduced pressure was performed to obtain 7.4 g (yield: 45%) of the target product, 2-(dimethylamino)ethoxyethyl vinyl ether, with a purity of 97%. Example 3 <CH 2 =CH-(OCH 2 CH 2 ) 2 -N + (CH 3 ) 2 -(CH 2 ) 3 -SO 3 - Synthesis of > In a 50 mL two-neck flask, 3.9 g (24.4 mmol) of 2-(dimethylamino)ethoxyethyl vinyl ether obtained in Example 1 was charged and purged with argon. Dehydrated acetone (11.0 g) was charged, and 1,3-propane sultone (3.2 g) was slowly added dropwise while stirring. The mixture was then stirred at 30°C or less for 24 hours, and the precipitated white solid was filtered off. The filtered white solid was dried to obtain the target product. The yield of the target product, the zwitterionic monomer, was 6.5 g (23.1 mmol), and the yield was 95%.

[0054] CH 2 =CH-(OCH 2 CH 2 ) 2 -N + (CH 3 ) 2 -(CH 2 ) 3 -SO 3 - The structure was confirmed by the following NMR data.

[0055] [ka]

[0056] [Table 2]

Claims

1. A compound represented by the following formula (2): R ５ -(O) ｑ -(CH ２ ) ｒ -(OR ６ ) Ｓ -N ＋ R ７ R ８ -(CH ２ ) ｔ -X ・・・(2) In formula (2), R ５ is CH ２ ═CH—, R ６ Each independently represents -CH ２ CH ２ --, --CH ２ CH ２ CH ２ -or-CH ２ CH (CH ３ )-, R ７ and R ８ each independently represents an alkyl group having 1 to 6 carbon atoms, q represents 1, r represents an integer of 1 to 4, s represents an integer of 1 to 3, t represents an integer of 1 to 4, and X is SO ３ － Or CO ２ － Represents.

2. In the formula (2), R 6 is —CH ２ CH ２ The compound according to claim 1, wherein

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