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EP-4741443-A1 - ORGANOPOLYSILOXANE HAVING TERTIARY AMINO GROUP IN MOLECULAR CHAIN AND METHOD FOR PRODUCING SAME

EP4741443A1EP 4741443 A1EP4741443 A1EP 4741443A1EP-4741443-A1

Abstract

[Object] One of the purposes of the present invention is to provide an organopolysiloxane that is an intermediate compound for providing a silicone macromer having a quaternary ammonium cation site in a molecular chain in which a (meth)acrylic group is introduced in a high percentage at both terminals. [Solution] The present invention provides an organopolysiloxane having a tertiary amino group in a molecular chain represented by the following general formula (1): wherein, 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 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; Q 1 and Q 2 are, independently of each other, a group represented by the following formula (2) or the following formula (3); "a" is an integer of 1 to 400; and "b" is an integer of 1 to 50; wherein, in formula (2), "n1" is an integer of 2 to 10, and "n2" is an integer of 0 to 10; wherein, 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.

Inventors

  • WATANABE TAKUMA

Assignees

  • SHIN-ETSU CHEMICAL CO., LTD.

Dates

Publication Date
20260513
Application Date
20240702

Claims (7)

  1. An organopolysiloxane having a tertiary amino group in a molecular chain represented by the following general formula (1): wherein, 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 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; Q 1 and Q 2 are, independently of each other, a group represented by the following formula (2) or the following formula (3); "a" is an integer of 1 to 400; and "b" is an integer of 1 to 50; wherein, in formula (2), "n1" is an integer of 2 to 10, and "n2" is an integer of 0 to 10; wherein, 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. The organopolysiloxane according to claim 1, wherein, in said general formula (1), Q 1 and Q 2 both are a group represented by said formula (2).
  3. The organopolysiloxane according to claim 1, wherein, in said general formula (1), one of Q 1 and Q 2 is a group represented by said formula (2), and the other of Q 1 and Q 2 is a group represented by said formula (3).
  4. The organopolysiloxane according to claim 1, wherein, in said general formula (1), Q 1 and Q 2 both are a group represented by said formula (3).
  5. A method for producing an organopolysiloxane having a tertiary amino group in a molecular chain represented by the following general formula (1): wherein, 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 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; Q 1 and Q 2 are, independently of each other, a group represented by the following formula (2) or the following formula (3); "a" is an integer of 1 to 400; and "b" is an integer of 1 to 50; wherein, in formula (2), "n1" is an integer of 2 to 10, and "n2" is an integer of 0 to 10; wherein, 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, wherein the production method comprises a step of subjecting (A) an organopolysiloxane having a tertiary amino group in a molecular chain represented by the following general formula (4) to a reaction 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 said general formula (1): wherein, in general formula (4), R, R 1 ,"a", and "b" are as defined above; Q 3 is, independently of each other, a hydrogen atom or a group represented by the following formula (3) or (5), and at least one Q 3 per molecule is a hydrogen atom; wherein, in formulas (5) and (3), R 1 is as defined above; wherein, in general formula (6), "n3" is an integer of 0 to 8, and "n4" is an integer of 0 to 10.
  6. The method for producing the organopolysiloxane having a tertiary amino group in the molecular chain according to claim 5, further comprising a step of reacting a double-terminal hydrosilyl group-containing organohydrogen polysiloxane and a tertiary amine having two allyl groups in the presence of a platinum catalyst to obtain the organopolysiloxane represented by said general formula (4).
  7. The production method according to claim 5 or 6, wherein the organopolysiloxane represented by said general formula (1) has 0.5 to 2 groups represented by said formula (2) as the average number of groups per molecule.

Description

TECHNICAL FIELD The present invention relates to an organopolysiloxane having a tertiary amino group in a molecular chain, and a method for producing the same. BACKGROUND ART 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 is being considered to make the contact lens surface hydrophilic. Among such considerations, the introduction of quaternary ammonium cation sites in silicone chains has been reported (Patent Literature 1 to 4). Among such reports, Patent Literature 1 describes a method for synthesizing a silicone macromer having a polymerizable group at both terminals and having a quaternary ammonium cation site in a molecular chain. PRIOR LITERATURE PATENT LITERATURE Patent Literature 1: JP National Phase Laid-Open No. 2009-542855Patent Literature 2: JP National Phase Laid-Open No. 2009-533532Patent Literature 3: JP National Phase Laid-Open No. 2010-516873Patent Literature 4: JP National Phase Laid-Open No. 2009-521547 SUMMARY OF THE INVENTION PROBLEM TO BE SOLVED BY THE INVENTION However, it is inferred that in a production method according to Patent Literature 1, a certain amount of silicone without polymerizable groups is contained as an impurity. It is unfavorable for silicone that is typically used as a contact lens material to contain a large amount of compounds without polymerizable groups. It is therefore desirable to establish a method for producing a silicone macromer having a quaternary ammonium cation site in a molecular chain in which a (meth)acrylic group is introduced in a high percentage at both terminals. One of the purposes of the present invention is to provide an organopolysiloxane that is an intermediate compound for providing a silicone macromer having a quaternary ammonium cation site in a molecular chain in which a (meth)acrylic group is introduced in a high percentage at both terminals. MEANS FOR SOLVING THE PROBLEMS As a result of diligent research to achieve the aforementioned purpose, the inventor found a production method to synthesize a silicone macromer having a quaternary ammonium cation site in a molecular chain in which a (meth)acrylic group is introduced in a high percentage at both terminals. The inventor synthesized a novel tertiary amino group-containing organopolysiloxane to be used as an intermediate compound of the production method, thereby completing the present invention. That is, the present invention provides an organopolysiloxane having a tertiary amino group in a molecular chain represented by the following general formula (1): wherein, 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; R1 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; Q1 and Q2 are, independently of each other, a group represented by the following formula (2) or the following formula (3); "a" is an integer of 1 to 400; and "b" is an integer of 1 to 50; wherein, in formula (2), "n1" is an integer of 2 to 10, and "n2" is an integer of 0 to 10; wherein, in formula (3), R1 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. Preferably, the organopolysiloxane further comprises the constituent features of the following items [1], [2], or [3]. [1] The organopolysiloxane, wherein, in said general formula (1), Q1 and Q2 both are a group represented by said formula (2).[2] The organopolysiloxane, wherein, in said general formula (1), one of Q1 and Q2 is a group represented by said formula (2), and the other of Q1 and Q2 is a group represented by said formula (3).[3] The organopolysiloxane, wherein, in said general formula (1), Q1 and Q2 both are a group represented by said formula (3). The present invention further provides a method for producing an organopolysiloxane having a tertiary amino group in a molecular chain represented by the following general formula (1): wherein, 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; R1 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; Q1 and Q2 are, independently of each other, a group represented by the following formula (2) or the following formula (3); "a" is an integer of 1 to 400; and "b" is an integer of 1 to 50; wherein, in formula (2), "n1" is an integer of 2 to 10, and "n2" is an integer of 0 to 10; wherein, in