Organopolysiloxane having tertiary amino group in molecular chain, and production method of the same

Abstract

To provide an organopolysiloxane which is an intermediate compound for providing a silicone macromer introduced with (meth)acrylic groups to both terminals in a high rate, and including a quaternary ammonium cation part in a molecular chain.SOLUTION: There is provided an organopolysiloxane having a tertiary amino group in a molecular chain, which expressed by the following general formula (1). In the general formula (1), R is mutually independently a group selected from the group consisting of a 1-10C alkyl group, a 6-10C aryl group, and a 7-10C aralkyl group, R1 is mutually independently a group selected from the group consisting of a 1-10 alkyl group, a 6-10 aryl group, and a 7-10 aralkyl group, Q1 and Q2 are each mutually independently a group including a polyethylene glycol unit or a specific amino group, a is an integer of 1-400, and b is an integer of 1-50.SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to an organopolysiloxane having a tertiary amino group in the molecular chain and a method for producing the same. [Background technology]

[0002] Silicone is widely used as a contact lens material due to its high oxygen permeability. However, since silicone is hydrophobic, the introduction of hydrophilic groups has been studied to hydrophilize the contact lens surface. Among them, the introduction of quaternary ammonium cation moieties into silicone chains has been reported (Patent Documents 1 to 4). In particular, Patent Document 1 describes a method for synthesizing a silicone macromer having polymerizable groups at both ends and a quaternary ammonium cation moiety in the molecular chain. [Prior art documents] [Patent documents]

[0003] [Patent Document 1] Special Publication No. 2009-542855 [Patent Document 2] Special Publication No. 2009-533532 [Patent Document 3] Special Publication No. 2010-516873 [Patent Document 4] Special Publication No. 2009-521547 Summary of the Invention [Problem to be solved by the invention]

[0004] However, it is presumed that the manufacturing method described in Patent Document 1 contains a certain amount of silicone without polymerizable groups as an impurity. It is generally not preferable for silicones used as contact lens materials to contain a large amount of compounds without polymerizable groups. Therefore, it is desirable to establish a manufacturing method for silicone macromers that contain quaternary ammonium cation moieties in the molecular chain and that can introduce a high proportion of (meth)acrylic groups to both ends.

[0005] An object of the present invention is to provide an organopolysiloxane that is an intermediate compound for providing a silicone macromer having a high proportion of (meth)acrylic groups at both ends and containing a quaternary ammonium cation moiety in the molecular chain. [Means for solving the problem]

[0006] As a result of intensive research conducted by the inventors in order to achieve the above object, they discovered a method for synthesizing a silicone macromer having a quaternary ammonium cation moiety in the molecular chain and having a high proportion of (meth)acrylic groups introduced at both ends. The inventors then synthesized a novel tertiary amino group-containing organopolysiloxane to be used as an intermediate compound in the manufacturing method, thereby completing the present invention.

[0007] That is, the present invention provides an organopolysiloxane having a tertiary amino group in the molecular chain, represented by the following general formula (1). [ka] (In the general formula (1), R is, independently of each other, a group selected from an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, and an aralkyl group having 7 to 10 carbon atoms; R 1 are each independently a group selected from an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, and an aralkyl group having 7 to 10 carbon atoms; Q 1 and Q 2 are each independently a group represented by the following formula (2) or (3), a is an integer of 1 to 400, and b is an integer of 1 to 50. [ka] (In formula (2), n1 is an integer from 2 to 10, and n2 is an integer from 0 to 10.) [ka] (In formula (3), R 1is a group selected from an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, and an aralkyl group having 7 to 10 carbon atoms).

[0008] Preferably, the organopolysiloxane further has the following constituent feature [1], [2] or [3]. [1] In the above general formula (1), Q 1 and Q 2 and are both groups represented by the above formula (2). [2] In the above general formula (1), Q 1 and Q 2 is a group represented by the above formula (2), and Q 1 and Q 2 the other of which is a group represented by the above formula (3). [3] In the above general formula (1), Q 1 and Q 2 and are both groups represented by the above formula (3).

[0009] The present invention further provides a method for producing an organopolysiloxane having a tertiary amino group in the molecular chain, represented by the following general formula (1): [ka] (In the general formula (1), R is, independently of each other, a group selected from an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, and an aralkyl group having 7 to 10 carbon atoms; R 1 are each independently a group selected from an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, and an aralkyl group having 7 to 10 carbon atoms; Q 1 and Q 2 are each independently a group represented by the following formula (2) or (3), a is an integer of 1 to 400, and b is an integer of 1 to 50. [ka] (In formula (2), n1 is an integer from 2 to 10, and n2 is an integer from 0 to 10.) [ka] (In formula (3), R 1 is a group selected from an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, and an aralkyl group having 7 to 10 carbon atoms. The present invention provides a method for producing an organopolysiloxane having a tertiary amino group in the molecular chain and represented by the following general formula (4), characterized by comprising a step of reacting (A) an organopolysiloxane having a tertiary amino group in the molecular chain and represented by the following general formula (4) with (B) a (poly)ethylene glycol monoalkenyl ether represented by the following general formula (6) in the presence of a platinum catalyst to obtain an organopolysiloxane having a tertiary amino group in the molecular chain and represented by the above general formula (1). [ka] (In general formula (4), R, R 1 , a and b are as above, and Q 3 are each independently a hydrogen atom or a group represented by the following formula (3) or (5), and at least one Q 3 is a hydrogen atom) [ka] [ka] (In formulas (5) and (3), R 1 is as above) [ka] (In the general formula (6), n3 is an integer of 0 to 8, and n4 is an integer of 0 to 10).

[0010] The present invention further provides a method for producing an organopolysiloxane having a tertiary amino group in the molecular chain, represented by the above general formula (1), which further comprises a step of reacting an organohydrogenpolysiloxane containing hydrosilyl groups at both ends with a tertiary amine having two allyl groups in the presence of a platinum catalyst to obtain an organopolysiloxane represented by the above general formula (4). The present invention further provides the above-mentioned production method, wherein the organopolysiloxane represented by the above general formula (1) has, on average, 0.5 to 2 groups represented by the above formula (2) per molecule. Effect of the Invention

[0011] The tertiary amino group-containing organopolysiloxane of the present invention is suitable as an intermediate compound for producing a silicone macromer having a quaternary ammonium cation site in the molecular chain with a high proportion of (meth)acrylic groups introduced at both ends. In addition, the production method of the present invention can efficiently produce the tertiary amino group-containing organopolysiloxane. Furthermore, the tertiary amino group-containing organopolysiloxane of the present invention is useful not only as the above silicone macromer, but also as an intermediate that can be easily derived into organopolysiloxanes having various reactive functional groups. [Brief description of the drawings]

[0012] [Figure 1] FIG. 1 is a 1H-NMR spectrum chart of the organopolysiloxane having a tertiary amino group in the molecular chain synthesized in Example 1. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0013] The present invention will be described in detail below. [Organopolysiloxane with tertiary amino groups in the molecular chain] The organopolysiloxane having a tertiary amino group of the present invention is represented by the following general formula (1). [ka] In the above general formula (1), R is, independently of each other, a group selected from an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, and an aralkyl group having 7 to 10 carbon atoms; R 1 are each independently a group selected from an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, and an aralkyl group having 7 to 10 carbon atoms; Q 1 and Q 2are each independently a group represented by the following formula (2) or (3), a is an integer of 1 to 400, and b is an integer of 1 to 50. [ka] In the above formula (2), n1 is an integer from 2 to 10, and n2 is an integer from 0 to 10. [ka] In the above formula (3), R 1 is a group selected from an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, and an aralkyl group having 7 to 10 carbon atoms.

[0014] In the above general formula (1), R is independently a group selected from an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, and an aralkyl group having 7 to 10 carbon atoms. Examples of the alkyl group having 1 to 10 carbon atoms include alkyl groups such as methyl group, ethyl group, propyl group, butyl group, and octyl group; and cycloalkyl groups such as cyclopentyl group and cyclohexyl group. Examples of the aryl group having 6 to 10 carbon atoms include a phenyl group, a methylphenyl group, and an ethylphenyl group. Examples of the aralkyl group having 7 to 10 carbon atoms include a phenylmethyl group and a phenylethyl group. R is preferably a methyl group or a phenyl group, and more preferably a methyl group.

[0015] In the above general formulas (1) and (3), R 1 are each independently a group selected from an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, and an aralkyl group having 7 to 10 carbon atoms. Examples of the alkyl group having 1 to 10 carbon atoms include alkyl groups such as a methyl group, an ethyl group, a propyl group, a butyl group, and an octyl group; and cycloalkyl groups such as a cyclopentyl group and a cyclohexyl group. Examples of the aryl group having 6 to 10 carbon atoms include a phenyl group, a methylphenyl group, and an ethylphenyl group. Examples of the aralkyl group having 7 to 10 carbon atoms include a phenylmethyl group and a phenylethyl group. In the above general formulas (1) and (3), R 1is preferably a methyl group or an ethyl group, more preferably a methyl group.

[0016] In the above general formula (1), Q 1 and Q 2 are each independently a group represented by the above formula (2) or (3).

[0017] In the above general formula (1), a is an integer of 1 to 400, preferably an integer of 1 to 100, and more preferably an integer of 5 to 50. b is an integer of 1 to 50, preferably an integer of 1 to 30, and more preferably an integer of 1 to 10.

[0018] In the above formula (2), n1 is an integer of 2 to 10, and preferably an integer of 2 to 4, and n2 is an integer of 0 to 10, and preferably an integer of 1 to 6.

[0019] [Method for producing organopolysiloxane having tertiary amino groups in the molecular chain] The method for producing the organopolysiloxane having tertiary amino groups in the molecular chain represented by the above general formula (1) is described in detail below. The production method is characterized by comprising the step of reacting (A) an organopolysiloxane having a tertiary amino group in the molecular chain represented by the following general formula (4) with (B) a (poly)ethylene glycol monoalkenyl ether represented by the following general formula (6) in the presence of a platinum catalyst to obtain a compound represented by the above general formula (1). [ka] [ka]

[0020] In the above general formula (4), Q 3 are each independently a hydrogen atom or a group represented by the following formula (3) or (5), and at least one Q 3 is a hydrogen atom. [ka] [ka]

[0021] In the above general formula (4), R is independently a group selected from an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, and an aralkyl group having 7 to 10 carbon atoms. Examples of the alkyl group having 1 to 10 carbon atoms include alkyl groups such as methyl group, ethyl group, propyl group, butyl group, and octyl group; and cycloalkyl groups such as cyclopentyl group and cyclohexyl group. Examples of the aryl group having 6 to 10 carbon atoms include a phenyl group, a methylphenyl group, and an ethylphenyl group. Examples of the aralkyl group having 7 to 10 carbon atoms include a phenylmethyl group and a phenylethyl group. R is preferably a methyl group or a phenyl group, and more preferably a methyl group.

[0022] In the above general formulas (4), (3) and (5), R 1 are each independently a group selected from an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, and an aralkyl group having 7 to 10 carbon atoms. Examples of the alkyl group having 1 to 10 carbon atoms include alkyl groups such as a methyl group, an ethyl group, a propyl group, a butyl group, and an octyl group; and cycloalkyl groups such as a cyclopentyl group and a cyclohexyl group. Examples of the aryl group having 6 to 10 carbon atoms include a phenyl group, a methylphenyl group, and an ethylphenyl group. Examples of the aralkyl group having 7 to 10 carbon atoms include a phenylmethyl group and a phenylethyl group. In the above general formulas (4), (3), and (5), R 1 is preferably a methyl group or an ethyl group, more preferably a methyl group.

[0023] In the above general formula (4), a is an integer of 1 to 400, preferably an integer of 1 to 100, and more preferably an integer of 5 to 50. b is an integer of 1 to 50, preferably an integer of 1 to 30, and more preferably an integer of 1 to 10.

[0024] In the above general formula (6), n3 is an integer of 0 to 8, and preferably an integer of 0 to 2. n4 is an integer of 0 to 10, and preferably an integer of 1 to 6.

[0025] The organopolysiloxane represented by the above general formula (4) preferably has the following structure: [ka] The hydrosilyl groups of the organopolysiloxane react with the (poly)ethylene glycol monoalkenyl ether represented by the general formula (6) to give an organopolysiloxane of the general formula (1) having a structure represented by formula (2) at its terminal.

[0026] As described above, the organopolysiloxane of the present invention contains a structure having a secondary amino group at its terminal, as represented by the above formula (3). This is because, in the production of the organohydrogenpolysiloxane represented by the above general formula (4), the terminal having a tertiary amino group, which has undergone internal rearrangement of the double bond by a platinum catalyst, is hydrolyzed during post-treatment after the hydrosilylation reaction, as shown in the following formula, to give a structure having a secondary amino group at its terminal, as represented by the above formula (3). [ka] Therefore, the organopolysiloxane represented by the above general formula (4) may be a compound having the following structure, or may be a mixture of a compound having a group represented by the above formula (5) at its terminal and a compound having a group represented by the above formula (3) at its terminal. [ka]

[0027] The organopolysiloxane represented by the general formula (4) may be one or a mixture of two or more compounds selected from the above organopolysiloxanes. Preferably, the organopolysiloxane has an average of 0 to 2 hydrogen atoms bonded to silicon atoms in one molecule, more preferably 1 to 2 hydrogen atoms, and even more preferably 1.5 to 2 hydrogen atoms bonded to silicon atoms in one molecule.

[0028] The organopolysiloxane represented by the above general formula (1) is preferably 1 and Q 2 are both groups represented by the above formula (2), 1 and Q 2 are both groups represented by the above formula (3), and 1 and Q 2 One of the groups represented by the formula (2) and the other by the formula (3) may be a compound, or a mixture of two or more selected from these compounds. More preferably, the organopolysiloxane may be an organopolysiloxane having, on average, 0 to 2, preferably 0.5 to 2, more preferably 1 to 2, and even more preferably 1.5 to 2 groups represented by the formula (2) in one molecule, and 0 to 2, preferably 0 to 1.5, more preferably 0 to 1, and even more preferably 0 to 0.5 groups represented by the formula (3) in one molecule.

[0029] In the production method of the present invention, the (poly)ethylene glycol monoalkenyl ether is used in an excess amount over the organopolysiloxane, and the mixing ratio of the (poly)ethylene glycol monoalkenyl ether is preferably 1.05 to 1.4 times the number of moles of terminal hydrosilyl groups contained in the organopolysiloxane.

[0030] The (poly)ethylene glycol monoalkenyl ether used in the production method of the present invention may be a commercially available product, such as allyl glycol, diethylene glycol monoallyl ether, or polyethylene glycol allyl ether (trade names: UNIOX PKA-5001 (average molecular weight: 200), UNIOX PKA-5002 (average molecular weight: 400), UNIOX PKA-5003 (average molecular weight: 450), UNIOX PKA-5004 (average molecular weight: 750), or UNIOX PKA-5005 (average molecular weight: 1,500), all manufactured by NOF Corporation).

[0031] The catalyst used in the production method of the present invention may be a known platinum catalyst. In particular, a chloroplatinic acid neutralized with sodium bicarbonate·vinylsiloxane complex (Karstedt's Catalyst) is more preferable. The amount of catalyst is not particularly limited as long as it is a catalytic amount, but is preferably 10 to 1,000 ppm based on the mass of the organohydrogenpolysiloxane containing hydrosilyl groups at both ends.

[0032] In the production method of the present invention, the reaction conditions such as the reaction time and the solvent used are not particularly limited. The reaction time is preferably 1 to 24 hours, more preferably 1 to 12 hours, and most preferably 1 to 6 hours. The solvent is preferably an aromatic hydrocarbon solvent such as toluene or xylene.

[0033] The method for producing the organopolysiloxane represented by the above general formula (4) is not particularly limited, but for example, it can be obtained by reacting an organohydrogenpolysiloxane containing hydrosilyl groups at both ends with a tertiary amine having two allyl groups in the presence of a platinum catalyst. In this production method, the reaction conditions such as the reaction time and the solvent used are not particularly limited and may be set appropriately.

[0034] Preferably, the organopolysiloxane having hydrosilyl groups at both ends is reacted with a tertiary amine having two allyl groups in the presence of a platinum catalyst in an excess equivalent amount of hydrosilyl groups to obtain an organopolysiloxane having the general formula (4) as an intermediate, and then the (poly)ethylene glycol monoalkenyl ether having the general formula (6) is added to the reaction system and reacted to produce the organopolysiloxane having the general formula (1). The organohydrogenpolysiloxane having hydrosilyl groups at both ends is used in an excess equivalent amount relative to the tertiary amine having two allyl groups. The molar ratio determines b in the general formula (1), which is the number of repetitions of the silicone chain and the tertiary amino group-containing portion. The blending ratio of the organopolysiloxane is preferably 1.05 to 2 times the number of moles of the tertiary amine.

[0035] In the method for producing organopolysiloxane represented by the above general formula (1), intermediate product (4) may be isolated in the first step before proceeding to the next step, or after the reaction in the first step, intermediate product (4) may be left untreated or may be removed by distillation only, without isolating intermediate product (4), before proceeding to the next step. As a method for producing organopolysiloxane represented by the above general formula (1) without isolating intermediate product (4), for example, an organohydrogenpolysiloxane containing hydrosilyl groups at both ends is reacted with a tertiary amine having two allyl groups in the presence of a platinum catalyst, and after confirming that no tertiary amine raw material remains, a (poly)ethylene glycol allyl ether and a platinum catalyst are added to the reaction solution, which is heated and stirred. After the reaction is completed, low boiling fractions are removed and the mixture is washed to obtain organopolysiloxane having tertiary amino groups in the molecular chain represented by the above general formula (1). EXAMPLES

[0036] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to the following examples. In the following 1 H-NMR measurements were performed using an ULTRASHIELD400 PLUS (BRUKER).

[0037] [Synthesis Example 1] In a three-neck flask equipped with a thermometer, a stirrer, and a reflux condenser, add [ka] 50.0 g of organohydrogenpolysiloxane containing hydrosilyl groups at both ends represented by the formula (I), 0.2 g of a toluene solution of chloroplatinic acid neutralized with sodium bicarbonate and vinylsiloxane complex (platinum content 0.5 wt%), and 17 g of toluene were charged and heated to 70°C. 5.3 g of diallylmethylamine was added dropwise over 30 minutes, and the mixture was heated and stirred at 75°C for 2 hours. After the reaction was completed, low boiling point fractions were removed at 100°C for 1 hour under a reduced pressure of 0.2 kPa. Next, 25 g of acetonitrile and 6.3 g of water were added, stirred, washed, and then allowed to stand to separate the silicone layer. This separation and washing operation was repeated three times. Low boiling point fractions were removed at 85°C for 1.5 hours under a reduced pressure of 0.3 kPa, and 24 g of organopolysiloxane represented by the formula (a) was obtained. [ka] In formula (a), each A is independently a hydrogen atom bonded to a silicon atom or a group represented by the following formula: The organopolysiloxane is a mixture of two or more compounds in which As are different, and has an average of 1.8 hydrogen atoms bonded to silicon atoms per molecule, and an average of 0.2 groups represented by formula (b) per molecule. [ka]

[0038] [Example 1] Production of organopolysiloxane having tertiary amino groups in the molecular chain represented by the above general formula (1) In a three-neck flask equipped with a thermometer, a stirrer, and a reflux condenser, 250.0 g of the organopolysiloxane represented by formula (a) obtained in Synthesis Example 1 above, 1.0 g of a toluene solution of chloroplatinic acid neutralized with sodium bicarbonate and vinylsiloxane complex (platinum content 0.5 wt%), and 83 g of toluene were charged and heated to 70 ° C. 24.3 g of allyl glycol and 0.5 g of a toluene solution of chloroplatinic acid neutralized with sodium bicarbonate and vinylsiloxane complex (platinum content 0.5 wt%) were added and heated and stirred at 75 ° C. for 1.5 hours. After the reaction was completed, the low boiling point fraction was removed at 90 ° C. for 1 hour under a reduced pressure of 0.3 kPa. Next, 125 g of acetonitrile and 31 g of water were added, stirred, washed, and then allowed to stand to separate the silicone layer. This separation and washing operation was repeated three times. The low boiling fraction was removed under reduced pressure of 0.9 kPa at 100° C. for 1.5 hours, yielding 247 g of an organopolysiloxane represented by the following formula (c). [ka] In the above formula (c), Q 1 are each independently a group represented by the following formula (d) or the above formula (b). 1 It is a mixture of two or more compounds having different structures, and has an average of 1.8 groups represented by the following formula (d) per molecule and an average of 0.2 groups represented by the above formula (b) per molecule. [ka]

[0039] The organopolysiloxane 1 The H-NMR spectrum is shown. 1 H-NMR(400MHz, CDCl3):δ -0.14~0.22(m,264H),0.41~0.56(m,16H),1.37~1.66(m,16H),2.06~2.58(m,21 .4H),3.42(t,J=7.0Hz,3.6H),3.51(t,J=4.6Hz,3.6H),3.70(t,J=4.4Hz,3.6H)

[0040] According to the production method of the present invention, tertiary amino group-containing organopolysiloxanes can be efficiently produced. The tertiary amino group-containing organopolysiloxanes of the present invention are suitable as intermediate compounds for producing silicone macromers having quaternary ammonium cation sites in the molecular chain, with (meth)acrylic groups being introduced at a high rate at both ends. Furthermore, the tertiary amino group-containing organopolysiloxanes of the present invention are useful not only as the above silicone macromers, but also as intermediates that can be easily derived into organopolysiloxanes having various reactive functional groups.

Claims

1. An organopolysiloxane having a tertiary amino group in the molecular chain, represented by the following general formula (1): 【Chemistry 1】 (In general formula (1), R is, independently of each other, a group selected from an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, and an aralkyl group having 7 to 10 carbon atoms; R １ are each independently a group selected from an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, and an aralkyl group having 7 to 10 carbon atoms; Q １ and Q. ２ are each independently a group represented by the following formula (2) or (3), a is an integer of 1 to 400, and b is an integer of 1 to 50. 【Chemistry 2】 (In formula (2), n1 is an integer from 2 to 10, and n2 is an integer from 0 to 10.) 【Chemistry 3】 (In formula (3), R １ is a group selected from an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, and an aralkyl group having 7 to 10 carbon atoms).

2. In the above general formula (1), Q １ and Q. ２ The organopolysiloxane according to claim 1, wherein both are groups represented by the above formula (2).

3. In the above general formula (1), Q １ and Q. ２ is a group represented by the above formula (2), and Q １ and Q. ２ The organopolysiloxane according to claim 1, wherein the other of said groups is a group represented by the above formula (3).

4. In the above general formula (1), Q １ and Q. ２ The organopolysiloxane according to claim 1, wherein both are groups represented by the above formula (3).

5. A method for producing an organopolysiloxane having a tertiary amino group in the molecular chain, represented by the following general formula (1), comprising the steps of: 【Chemistry 4】 (In general formula (1), R is, independently of each other, a group selected from an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, and an aralkyl group having 7 to 10 carbon atoms; R １ are each independently a group selected from an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, and an aralkyl group having 7 to 10 carbon atoms; Q １ and Q. ２ are each independently a group represented by the following formula (2) or (3), a is an integer of 1 to 400, and b is an integer of 1 to 50. 【Chemistry 5】 (In formula (2), n1 is an integer from 2 to 10, and n2 is an integer from 0 to 10.) 【Chemistry 6】 (In formula (3), R １ is a group selected from an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, and an aralkyl group having 7 to 10 carbon atoms. The above-mentioned production method comprises a step of reacting (A) an organopolysiloxane having a tertiary amino group in the molecular chain, represented by the following general formula (4), with (B) a (poly)ethylene glycol monoalkenyl ether represented by the following general formula (6), in the presence of a platinum catalyst, to obtain an organopolysiloxane having a tertiary amino group in the molecular chain, represented by the above general formula (1). 【Chemistry 7】 (In general formula (4), R, R １ , a and b are as defined above, and Q ３ are each independently a hydrogen atom or a group represented by the following formula (3) or (5), and at least one Q ３ is a hydrogen atom) 【Chemistry 8】 【Chemistry 9】 (In formulas (5) and (3), R １ is as above) 【Chemistry 10】 (In general formula (6), n3 is an integer from 0 to 8, and n4 is an integer from 0 to 10).

6. 6. The method for producing an organopolysiloxane having a tertiary amino group in the molecular chain according to claim 5, further comprising a step of reacting an organohydrogenpolysiloxane containing hydrosilyl groups at both ends with a tertiary amine having two allyl groups in the presence of a platinum catalyst to obtain an organopolysiloxane represented by general formula (4).

7. 7. The method according to claim 5, wherein the organopolysiloxane represented by the general formula (1) has an average of 0.5 to 2 groups represented by the formula (2) per molecule.

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