JP2013181130A - Amphiphilic cationic polymer composition having reactive group - Google Patents

Abstract

An amphiphilic cationic polymer composition having a reactive group is provided.
A monoallyl compound and / or a diallyl compound and a triallyl compound and / or a tetraallyl compound are copolymerized, and a monoallyl compound and / or a diallyl compound and a triallyl compound and / or a tetraallyl compound are unsaturatedly bonded to the terminal. An amphiphilic cationic polymer composition having a reactive group was obtained by copolymerizing with a polyalkylene glycol compound having the following formula.
[Selection figure] None

Description

The present invention relates to an amphiphilic cationic polymer composition having a reactive group, and the molecular weight of the polymer, the number of pendant double bonds, the polymer structure, etc. can be designed in any way according to the purpose of use. An object of the present invention is to provide a polymer composition that can be used for copolymerization in both aqueous and solvent systems, and that can introduce a cationic polymer chain through a covalent bond into a polymer chain of another composition. is there.

  Polymers such as acrylamide polymer, diallyldimethylammonium chloride polymer and monoallyl ammonium chloride polymer are very important industrially and are used for various applications. For example, it is used as a flocculant and decoloring agent for water treatment, dye fixing agent and yield improver for paper making, and antibacterial agent and biocatalyst for medical and food related. It has been.

  Cationic polymers are strongly hydrophilic and only soluble in highly polar solvents such as water and methanol. By overcoming this drawback and designing and synthesizing novel amphiphilic cationic polymers that are widely soluble in organic solvents as well as polar solvents, new applications in various fields will be developed. Although few cationic polymers are soluble in nonpolar solvents, there are some reports. For example, cationic associative polyurethane is a cationic polymer that can be dissolved and dispersed in water and also soluble in an organic solvent (Patent Document 1). However, the cationic polymer described in Patent Document 1 cannot be introduced into a polymer chain composed of other components via a covalent bond. The cationic polymer compound described in Patent Document 2 can be dissolved in various organic solvents, but cannot be introduced into a polymer chain composed of other components via a covalent bond. In the method using a polymer crosslinking agent containing a tertiary amine and / or quaternary ammonium salt described in Patent Document 3, reactive groups are left only at both ends of the polymer chain, and the mechanism for increasing the molecular weight is methylenebis. It is equivalent to a low molecular weight crosslinking agent such as acrylamide and can only be used in aqueous systems. In any case, the cationic property can be dissolved in water or an organic solvent, and the cationic polymer chain can be introduced into the polymer chain composed of other components via a covalent bond. There is no polymer.

JP 2002-105161 A JP-A-5-194671 JP 2002-105138 A

The object of the present invention is to be able to design the molecular weight of the polymer, the number of pendant double bonds, the polymer structure, etc. according to the purpose of use, and can be used for copolymerization in both aqueous and solvent systems. It is an object of the present invention to provide a novel amphiphilic cationic polymer composition having a reactive group capable of introducing a cationic polymer chain into a polymer chain having another composition via a covalent bond.

As a result of intensive studies, the present inventor has copolymerized a monoallyl compound and / or a diallyl compound and a triallyl compound and / or a tetraallyl compound, and also has a monoallyl compound and / or a diallyl compound and a triallyl compound and / or A novel amphiphilic cationic polymer composition having a reactive group can be obtained by copolymerizing a tetraallyl compound and a polyalkylene glycol compound having an unsaturated bond at the terminal, and the present invention has been completed. It came to do.

That is, the novel amphiphilic cationic polymer composition having a reactive group of the present invention is a compound represented by the following general formula (1):

[Wherein, R ₁ and R ₂ are the same or different and each represents a hydrogen atom, a linear or branched alkyl group having 1 to 3 carbon atoms, a methoxyethyl group, a methoxypropyl group, or an ethoxyethyl group, and R ₃ represents hydrogen It represents an atom, a linear or branched alkyl group having 1 to 3 carbon atoms, a branched or cyclic alkyl group, a methoxyethyl group, a methoxypropyl group, an ethoxyethyl group, or a phenyl group. X ₁ represents a halide ion, a hydroxide ion or an anion of an organic acid or an inorganic acid. ]

And a compound represented by the following general formula (2):

[Wherein, R ₄ and R ₅ are the same or different and each represents a hydrogen atom, a linear or branched alkyl group having 1 to 3 carbon atoms, a methoxyethyl group, a methoxypropyl group, an ethoxyethyl group, or a phenyl group. X ₂ represents a halide ion, a hydroxide ion or an anion of an organic acid or an inorganic acid. ]

At least one selected from among the compounds represented by the following general formula (3),

[Wherein, R ₆ represents a hydrogen atom, a linear or branched alkyl group having 1 to 3 carbon atoms, a methoxyethyl group, a methoxypropyl group, an ethoxyethyl group, or a phenyl group. X ₃ represents a halide ion, a hydroxide ion or an anion of an organic acid or an inorganic acid. ]

And a compound represented by the following general formula (4):

[X ₄ represents a halide ion, a hydroxide ion or an anion of an organic acid or an inorganic acid. ]

At least one selected from among the compounds represented by the following general formula (5),

[Wherein, R ₇ and R ₈ are the same or different and each represents a hydrogen atom, a linear, branched or cyclic alkyl group having 4 to 18 carbon atoms, a benzyl group, or a phenylethyl group, and R ₉ represents 4 to 4 carbon atoms] 18 linear, branched or cyclic alkyl groups, benzyl groups or phenylethyl groups are represented. X ₅ represents a halide ion, a hydroxide ion or an anion of an organic acid or an inorganic acid. ]

And a compound represented by the following general formula (6):

[Wherein R ₁₀ represents a hydrogen atom, a linear, branched or cyclic alkyl group having 4 to 18 carbon atoms, a benzyl group or a phenylethyl group, and R ₁₁ represents a linear, branched and cyclic group having 4 to 18 carbon atoms. Represents an alkyl group, a benzyl group or a phenylethyl group. X ₆ represents a halide ion, a hydroxide ion or an anion of an organic acid or an inorganic acid. ]

And a compound represented by the following general formula (7):

[Wherein, R ₁₂ represents a linear, branched or cyclic alkyl group having 4 to 18 carbon atoms, a benzyl group or a phenylethyl group. X ₇ represents a halide ion, a hydroxide ion or an anion of an organic acid or an inorganic acid. ]

At least one selected from the group consisting of 1 to 98/1 to 98/1 to 98 mol%, and a polymer obtained by performing multi-component copolymerization, wherein a pendant allyl group is formed in the polymer chain. It contains 1 or more.

  In addition, at least one of the compounds represented by the general formulas (1), (2), (5), and (6), and the general formulas (3), (4), and (7) according to claim 1 At least one of the compounds represented,

A compound represented by the following general formula (8):

[Wherein, the repeating unit of the ethylene glycol unit represents 1 = 0 to 30, the repeating unit of the propylene glycol unit represents m = 0 to 13, and the repeating unit of the butylene glycol unit represents n = 0 to 6 (l + m + n ≠ 0). R ₁₃ represents a hydrogen atom, a linear, branched and cyclic alkyl group having 1 to 18 carbon atoms, a benzyl group or a phenylethyl group. R ₁₄ represents a hydrogen atom or a methyl group. ]

At least one selected from the group consisting of 1 to 98/1 to 98/1 to 98 mol%, and a polymer obtained by performing multi-component copolymerization, wherein a pendant allyl group is formed in the polymer chain. It contains 1 or more.

The novel amphiphilic cationic polymer composition having a reactive group of the present invention can freely design the molecular weight of the polymer, the structure of the polymer, and the number of pendant double bonds. A cationic polymer chain can be introduced through a covalent bond into a polymer chain having another composition, which can be subjected to polymerization.

  Hereinafter, the present invention will be described in detail.

The novel amphiphilic cationic polymer composition having a reactive group of the present invention is at least selected from the compound represented by the general formula (1) and the compound represented by the general formula (2). At least one selected from one compound, a compound represented by the general formula (3) and a compound represented by the general formula (4), a compound represented by the general formula (5), and the above A compound represented by the general formula (6) and at least one selected from the compounds represented by the general formula (7) in a ratio of 1 to 98/1 to 98/1 to 98 mol%. It can be obtained by copolymerization.

Alternatively, among the compound represented by the general formula (1), the compound represented by the general formula (2), the compound represented by the general formula (5), and the compound represented by the general formula (6) And at least one of the compound represented by the general formula (3), the compound represented by the general formula (4) and the compound represented by the general formula (7), and the general formula ( It can be obtained by multi-copolymerizing at least one selected from the compounds represented by 8) at a ratio of 1 to 98/1 to 98/1 to 98 mol%.

Examples of the linear and branched alkyl group having 1 to 3 carbon atoms represented by R ₁ , R ₂ and R ₃ of the compound represented by the general formula (1) include a methyl group, an ethyl group, an n-propyl group, An isopropyl group etc. can be mentioned. Halide ions, organic acids represented by X _1, fluoride ion as an anion of an inorganic acid, a chloride ion, bromide ion, iodide ion, sulfate ion, nitrate ion, phosphate ion, formate ion, acetate ion, oxalic An acid ion etc. can be mentioned.

Examples of the compound represented by the general formula (1) include allyldimethylamine hydrochloride, allyltrimethylammonium chloride, allyldiethylamine hydrochloride, allyldimethylamine bromide, allyldimethylamine sulfate, allyldimethylamine nitrate, and the like. 1 type selected from these, or 2 or more types may be combined.

Examples of the linear and branched alkyl group having 1 to 3 carbon atoms represented by R ₄ and R ₅ of the compound represented by the general formula (2) include a methyl group, an ethyl group, an n-propyl group, and an isopropyl group. Can be mentioned. As anions of halide ion, organic acid and inorganic acid represented by X ₂ , fluoride ion, chloride ion, bromide ion, iodide ion, sulfate ion, nitrate ion, phosphate ion, formate ion, acetate ion, shu An acid ion etc. can be mentioned.

Examples of the compound represented by the general formula (2) include diallyldimethylammonium chloride (hereinafter abbreviated as DADMAC), diallyldiethylammonium chloride, diallyldimethylammonium bromide, diallyldimethylammonium sulfate, diallyldimethylammonium nitrate, and the like. 1 type selected from these, or 2 or more types may be combined.

Examples of the linear and branched alkyl group having 1 to 3 carbon atoms represented by R ₆ of the compound represented by the general formula (3) include a methyl group, an ethyl group, an n-propyl group, and an isopropyl group. Can do. Halide ions, organic acids represented by X _3, fluoride as an anion of an inorganic acid ion, chloride ion, bromide ion, iodide ion, sulfate ion, nitrate ion, phosphate ion, formate ion, acetate ion, oxalic An acid ion etc. can be mentioned.

Examples of the compound represented by the general formula (3) include triallylamine hydrochloride (hereinafter abbreviated as Tri-AAC), triallylmethylammonium chloride, triallylethylammonium chloride, triallylmethylammonium bromide, triallylmethylammonium sulfate. , Triallylmethylammonium nitrate and the like can be mentioned, and one kind selected from these may be used, or two or more kinds may be combined.

Halide ion represented by X ₄ in the compound represented by the general formula (4), an organic acid, fluoride as an anion of an inorganic acid ion, chloride ion, bromide ion, iodide ion, sulfate ion, nitrate ion , Phosphate ions, formate ions, acetate ions, oxalate ions, and the like.

Examples of the compound represented by the general formula (4) include tetraallylammonium chloride, tetraallylammonium sulfate, tetraallylammonium nitrate, tetraallylammonium acetate, tetraallylammonium oxalate, and the like. 1 type selected from may be used, or 2 or more types may be combined.

Examples of the linear, branched and cyclic alkyl groups having 4 to 18 carbon atoms represented by R ₇ , R ₈ and R ₉ of the compound represented by the general formula (5) include an n-butyl group and a t-butyl group. , Amyl group, n-hexyl group, n-octyl group, n-lauryl group, n-stearyl group and the like. Halide ion represented by X _5, organic acids, fluoride as an anion of an inorganic acid ion, chloride ion, bromide ion, iodide ion, sulfate ion, nitrate ion, phosphate ion, formate ion, acetate ion, oxalic An acid ion etc. can be mentioned.

Examples of the compound represented by the general formula (5) include allyl lauryl amine hydrochloride (hereinafter abbreviated as ALAC), allyl stearyl amine hydrochloride (hereinafter abbreviated as ASAC), allyl dibutyl amine hydrochloride, allyl trioctyl ammonium chloride, Examples include allyl trioctadecyl ammonium chloride, allyl dibenzylamine hydrochloride, allyl dicyclohexylamine hydrochloride, allyl tricyclohexyl ammonium chloride, and the like. One kind selected from these may be used, or two or more kinds may be combined. .

Examples of the linear, branched and cyclic alkyl groups having 4 to 18 carbon atoms represented by R ₁₀ and R ₁₁ of the compound represented by the general formula (6) include an n-butyl group, a t-butyl group, and an amyl group. , N-hexyl group, n-octyl group, n-dodecyl group, n-octadecyl group and the like. Halide ions, organic acids represented by X _6, fluoride ion as an anion of an inorganic acid, a chloride ion, bromide ion, iodide ion, sulfate ion, nitrate ion, phosphate ion, formate ion, acetate ion, oxalic An acid ion etc. can be mentioned.

Examples of the compound represented by the general formula (6) include diallyl dioctyl ammonium chloride, diallyl dioctadecyl ammonium chloride, diallyl benzylamine hydrochloride, diallyl cyclohexylamine hydrochloride, diallyl dicyclohexyl ammonium chloride, diallyl dioctadecyl ammonium bromide, diallyl dichloride. Examples include octadecyl ammonium sulfate, diallyl dioctadecyl ammonium nitrate, and the like. One of these may be selected, or two or more may be combined.

Examples of the linear, branched and cyclic alkyl group having 4 to 18 carbon atoms represented by R ₁₂ of the compound represented by the general formula (7) include an n-butyl group, a t-butyl group, an amyl group, an n- A hexyl group, n-octyl group, n-dodecyl group, n-octadecyl group, etc. can be mentioned. Halide ions, organic acids represented by X _7, fluoride ion as an anion of an inorganic acid, a chloride ion, bromide ion, iodide ion, sulfate ion, nitrate ion, phosphate ion, formate ion, acetate ion, oxalic An acid ion etc. can be mentioned.

Examples of the compound represented by the general formula (7) include triallyl dodecyl ammonium chloride, triallyl octadecyl ammonium chloride, triallyl dodecyl ammonium bromide, triallyl dodecyl ammonium sulfate, triallyl dodecyl ammonium nitrate and the like. , One selected from these may be used, or two or more may be combined.

Examples of the linear, branched and cyclic alkyl group having 1 to 18 carbon atoms represented by R ₁₃ of the compound represented by the general formula (8) include a methyl group, an ethyl group, a propyl group, an n-butyl group, t -Butyl group, amyl group, n-hexyl group, n-octyl group, n-dodecyl group, n-octadecyl group and the like can be mentioned.

Examples of the compound represented by the general formula (8) include polyethylene glycol monomethacrylate, polypropylene glycol monomethacrylate, polybutylene glycol monomethacrylate, poly (ethylene glycol / propylene glycol) monomethacrylate, ethylene glycol / polypropylene glycol monomethacrylate, methoxy Examples thereof include polyethylene glycol monomethacrylate, ethoxypolyethylene glycol monomethacrylate, lauroxypolyethylene glycol monomethacrylate, and phenoxypolyethyleneglycol monomethacrylate.

As a method for producing a novel amphiphilic cationic polymer composition having a reactive group, a radical polymerization reaction is preferably used. The radical polymerization reaction can be easily performed by a known method. For example, the radical polymerization reaction is represented by Tri-AAC which is one of the compounds represented by the general formula (3) and the general formula (5). An initiator such as 2,2′-azobis (2-methylpropionamidine) dihydrochloride in a water solvent at a ratio of 1-99 / 99 to 1 mol% with ALAC which is one of the compounds Can be carried out by reacting at a polymerization temperature of 25 to 90 ° C. for 1 to 48 hours.

As radical polymerization initiators, inorganic or organic peroxides such as potassium persulfate, ammonium persulfate, and t-butyl hydroperoxide, 2,2′-azobis [2- (2-imidazolin-2-yl) propane] Disulfate dihydrochloride, 2,2′-azobis [N- (2-carboxyl) -2-methylpropionamidine] hydrate, 2,2′-azobis {2- [1- (2-hydroxyethyl) -2-imidazolin-2-yl] propane} dihydrochloride, 2,2′-azobis [2- (2-imidazolin-2-yl) propane], 2,2′-azobis (1-imino-1-pyrrolidino An azo compound such as 2-methylpropane) dihydrochloride may be mentioned, but is not particularly limited.

The polymerization temperature is suitably 25 to 90 ° C. and may be heated to control the molecular weight of the novel amphiphilic cationic polymer composition having the desired reactive group.

As the charged amount of general formulas (3), (4), and (7) increases, gelation occurs at a lower polymerization rate, and an insoluble / infusible network polymer is formed. It is a novel amphiphilic cationic polymer composition in which the separated sol has a target reactive group.

  A novel amphiphilic cationic polymer composition having a reactive group according to the present invention is provided with a polymer having a molecular structure that has not been obtained by a conventional crosslinking agent, and includes a flocculant and decoloring agent related to water treatment, Industrial utility value of paper-related dye fixing agents and yield improvers is high.

EXAMPLES The present invention will be specifically described below with reference to examples, but the present invention is not limited to these examples.

Examples 1-2
A separable flask was equipped with a stirrer, N ₂ gas introduction pipe, and gas trap, and the molar ratio of DADMAC, Tri-AAC and ALAC (DADMAC / Tri-AAC / ALAC) was 76.5 / 8.5 / 15 (Examples). 1), 45/5/50 (Example 2), water was used as a solvent, [total monomer concentration] (hereinafter abbreviated as [M]) = 2 mol / L, 2,2 as an initiator '-Azobis (2-methylpropionamidine) dihydrochloride (manufactured by Wako Pure Chemical Industries, Ltd., hereinafter abbreviated as V-50) was used, and [initiator concentration] (hereinafter abbreviated as [I]) = 0.015 mol / L The copolymerization was carried out under conditions of a polymerization temperature of 50 ° C. The polymerization solution in the middle of the polymerization was poured into acetone to precipitate the polymer, and the resulting white solid was purified by repeated reprecipitation with acetone. In the result of proton nuclear magnetic resonance spectroscopy (hereinafter abbreviated as ¹ H-NMR) measurement of the obtained white solid, a signal attributed to methylene proton at 5.5 ppm and a signal attributed to methine proton at 5.8 ppm As a result, it was confirmed that a pendant allyl group remained in the polymer.

Example 3
A separable flask was equipped with a stirrer, N ₂ gas inlet tube, and gas trap and charged so that Tri-AAC / allyl octylamine hydrochloride = 10/90. Water was used as the solvent, and [M] = 4 mol / L. Then, V-50 was used as an initiator, and copolymerization was performed under the conditions of [I] = 0.06 mol / L and a polymerization temperature of 65 ° C. The polymerization solution in the middle of the polymerization was poured into acetone to precipitate the polymer, and the resulting white solid was purified by repeated reprecipitation with acetone. In the result of ¹ H-NMR measurement of the obtained white solid, a signal attributed to methylene proton was detected at 5.5 ppm, and a signal attributed to methine proton was detected at 5.8 ppm. It was confirmed that the allyl group was a residue.

Example 4
A separable flask is equipped with a stirrer, N ₂ gas inlet tube, and gas trap, and the molar ratio of DADMAC, Tri-AAC and ASAC is (DADMAC / Tri-AAC / ASAC) 85.5 / 9.5 / 5. And using a mixed solvent of water / methanol as the solvent, [M] = 2 mol / L, using V-50 as the initiator, and [I] = 0.015 mol / L at a polymerization temperature of 60 ° C. Copolymerization was performed. The polymerization solution in the middle of the polymerization was poured into acetone to precipitate the polymer, and the resulting white solid was purified by repeated reprecipitation with acetone. In the result of ¹ H-NMR measurement of the obtained white solid, a signal attributed to methylene proton was detected at 5.5 ppm, and a signal attributed to methine proton was detected at 5.8 ppm. It was confirmed that the allyl group was a residue.

Examples 5-6
A separable flask is equipped with a stirrer, N ₂ gas inlet tube, and gas trap, DADMAC, Tri-AAC, Blemmer PE-350 (polyethylene glycol monomethacrylate, the number of repeating units of oxyethylene group is about 8, solid content 100%, (Made by Oil Co., Ltd.) with a molar ratio (DADMAC / Tri-AAC / Blemmer PE-350) of 63/7/30 (Example 5) and 27/3/70 (Example 6), and the solvent Copolymerization was performed using [M] = 2 mol / L, V-50 as an initiator, [I] = 0.015 mol / L, and a polymerization temperature of 60 ° C. It was. After completion of the reaction, the mixture was poured into acetone to precipitate a polymer, and the resulting white solid was purified by repeated reprecipitation with acetone. In the result of ¹ H-NMR measurement of the obtained white solid, a signal attributed to methylene proton was detected at 5.5 ppm, and a signal attributed to methine proton was detected at 5.8 ppm. It was confirmed that the allyl group was a residue.

Comparative Example 1
A separable flask was equipped with a stirrer, N ₂ gas inlet tube, and gas trap, and the molar ratio of DADMAC and Tri-AAC was charged to 90/10 (Comparative Example 1), water was used as the solvent, and [M] = 2 mol / L, V-50 was used as an initiator, and copolymerization was performed under the conditions of [I] = 0.015 mol / L and a polymerization temperature of 50 ° C. The polymerization solution in the middle of polymerization was poured into 2-propanol (hereinafter abbreviated as IPA) to precipitate a polymer, and the resulting white solid was purified by repeated reprecipitation with IPA. In the measurement result of the obtained white solid by ¹ H-NMR, a signal attributed to methylene proton was detected at 5.5 ppm and a signal attributed to methine proton was detected at 5.8 ppm. It was confirmed that the pendant allyl group remained.

Comparative Example 2
A separable flask was equipped with a stirrer, N ₂ gas inlet tube, and gas trap, and the molar ratio of DADMAC and ALAC was set to 85/15 (Comparative Example 2), water was used as the solvent, and [M] = 2 mol / L, V-50 was used as an initiator, and copolymerization was performed under the conditions of [I] = 0.015 mol / L and a polymerization temperature of 60 ° C. The polymerization solution in the middle of the polymerization was poured into a mixture of acetone / IPA to precipitate the polymer, and the resulting white solid was purified by repeated reprecipitation with a mixture of acetone / IPA. In the measurement result of the obtained white solid by ¹ H-NMR, signals attributable to methylene protons and methine protons of the allyl group were not detected at 5.5 to 5.8 ppm.

  The solubility of the prepared novel amphiphilic cationic polymer composition having a reactive group is shown in Table 1 below. As a method for confirming solubility, the test was conducted by adding the polymer to 5 wt% with respect to various solvents.

○: soluble, ×: insoluble, Δ: emulsification / dispersion A: water, B: methanol, C: ethanol, D: n-propanol, E: n-butanol, F: n-hexanol, G: n-heptanol, H: n-octanol, I: chloroform, J: tetrahydrofuran, K: N, N-dimethylformamide, L: N-methyl-2-pyrrolidone

(Figure 1)


¹ H-NMR spectrum of the polymer obtained in Example 2

(Figure 2)
¹ H-NMR spectrum of the polymer obtained in Comparative Example 1

In Examples 1 to 6, the polymer chain had a pendant allyl group and could be dissolved in various solvents, but in Comparative Example 1, the polymer chain had a pendant allyl group but was very polar such as water. In Comparative Example 2, although the solubility was improved, the pendant allyl group was not present in the polymer chain.

Claims (2)

A compound represented by the following general formula (1):
[Wherein, R ₁ and R ₂ are the same or different and each represents a hydrogen atom, a linear or branched alkyl group having 1 to 3 carbon atoms, a methoxyethyl group, a methoxypropyl group, or an ethoxyethyl group, and R ₃ represents hydrogen It represents an atom, a linear or branched alkyl group having 1 to 3 carbon atoms, a methoxyethyl group, a methoxypropyl group, an ethoxyethyl group, or a phenyl group. X ₁ represents a halide ion, a hydroxide ion or an anion of an organic acid or an inorganic acid. And a compound represented by the following general formula (2):
[Wherein, R ₄ and R ₅ are the same or different and each represents a hydrogen atom, a linear or branched alkyl group having 1 to 3 carbon atoms, a methoxyethyl group, a methoxypropyl group, an ethoxyethyl group, or a phenyl group. X ₂ represents a halide ion, a hydroxide ion or an anion of an organic acid or an inorganic acid. A compound represented by the following general formula (3):
[Wherein, R ₆ represents a hydrogen atom, a linear or branched alkyl group having 1 to 3 carbon atoms, a methoxyethyl group, a methoxypropyl group, an ethoxyethyl group, or a phenyl group. X ₃ represents a halide ion, a hydroxide ion or an anion of an organic acid or an inorganic acid. And a compound represented by the following general formula (4),
[X ₄ represents a halide ion, a hydroxide ion or an anion of an organic acid or an inorganic acid. A compound represented by the following general formula (5):
[Wherein, R ₇ and R ₈ are the same or different and each represents a hydrogen atom, a linear, branched or cyclic alkyl group having 4 to 18 carbon atoms, a benzyl group, or a phenylethyl group, and R ₉ represents 4 to 4 carbon atoms] 18 linear, branched or cyclic alkyl groups, benzyl groups or phenylethyl groups are represented. X ₅ represents a halide ion, a hydroxide ion or an anion of an organic acid or an inorganic acid. And a compound represented by the following general formula (6):
[Wherein R ₁₀ represents a hydrogen atom, a linear, branched or cyclic alkyl group having 4 to 18 carbon atoms, a benzyl group or a phenylethyl group, and R ₁₁ represents a linear, branched or cyclic group having 4 to 18 carbon atoms. Represents an alkyl group, a benzyl group or a phenylethyl group. X ₆ represents a halide ion, a hydroxide ion or an anion of an organic acid or an inorganic acid. And a compound represented by the following general formula (7):
[Wherein, R ₁₂ represents a linear, branched or cyclic alkyl group having 4 to 18 carbon atoms, a benzyl group or a phenylethyl group. X ₇ represents a halide ion, a hydroxide ion or an anion of an organic acid or an inorganic acid. At least one selected from the group consisting of 1 to 98/1 to 98/1 to 98 mol%, and a pendant allyl group in the polymer chain. A novel amphiphilic cationic polymer composition having a reactive group, characterized by containing at least one compound. At least one of the compounds represented by the general formulas (1), (2), (5) and (6) according to claim 1, and the general formulas (3), (4) and (7) according to claim 1. ) And at least one compound represented by the following general formula (8):
[Wherein, the repeating unit of the ethylene glycol unit represents 1 = 0 to 30, the repeating unit of the propylene glycol unit represents m = 0 to 13, and the repeating unit of the butylene glycol unit represents n = 0 to 6 (l + m + n ≠ 0). R ₁₃ represents a hydrogen atom, a linear, branched or cyclic alkyl group having 1 to 18 carbon atoms, a benzyl group, or a phenylethyl group. R ₁₄ represents a hydrogen atom or a methyl group. At least one selected from the group consisting of 1 to 98/1 to 98/1 to 98 mol%, and a pendant allyl group in the polymer chain. A novel amphiphilic cationic polymer composition having a reactive group, characterized in that it contains one or more.