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US-12617902-B2 - Composition and siloxane-based thermoplastic resin using same, and methods for producing same

US12617902B2US 12617902 B2US12617902 B2US 12617902B2US-12617902-B2

Abstract

To provide a composition containing a siloxane block-containing diol compound that is easy to manufacture industrially. A composition containing a siloxane block-containing diol compound, wherein the siloxane block-containing diol compound is represented by the following formula (I): wherein R 1 and R 2 are each independently an alkyl group having 1 to 20 carbon atoms which may have a substituent, or an aryl group having 6 to 30 carbon atoms which may have a substituent, m is an integer of 1 to 25, n is an integer of 3 to 200, and Xs each independently represent any of the following formulae (I 1 ) to (I 6 ):

Inventors

  • Kazuyoshi Uera
  • Kohei Kamatani
  • Hisato AKIMOTO
  • Daisuke Taguchi

Assignees

  • MITSUBISHI GAS CHEMICAL COMPANY, INC.

Dates

Publication Date
20260505
Application Date
20210922
Priority Date
20200923

Claims (4)

  1. 1 . A composition comprising a siloxane block-containing diol compound, wherein the siloxane block-containing diol compound is represented by the following formula (I): wherein R 1 and R 2 are each independently an alkyl group having 1 to 20 carbon atoms which may have a substituent, or an aryl group having 6 to 30 carbon atoms which may have a substituent, m is an integer of 1 to 25, n is an integer of 3 to 200, the Xs each independently represent any of the following formulae (I 1 ) to (I 5 ): A 1 and A 2 are each independently —(CR 6A R 6B ) q1 — or —(O—(CR 6A R 6B ) q2 ) q3 —, wherein R 6A and R 6B are each independently H or an alkyl group having 1 to 6 carbon atoms, q1 is an integer of 0 to 10, q2 is an integer of 0 to 10, and q3 is an integer of 0 to 10, R 3 and R 4 each independently represent a halogen atom, an aliphatic hydrocarbon group having 1 to 20 carbon atoms, an alkoxyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, an aralkyl group having 7 to 20 carbon atoms, an aromatic hydrocarbon-oxy group having 6 to 20 carbon atoms, or a cycloalkoxyl group having 3 to 20 carbon atoms, p1 and p2 are each independently an integer of 0 to 4, R 5 s each independently represent H or an alkyl group having 1 to 6 carbon atoms, X 1 and X 2 are each independently a single bond or a group shown below: wherein R 7 and R 8 are each independently H, a halogen atom, an aliphatic hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, an alkoxyl group having 1 to 20 carbon atoms which may have a substituent, or an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent, or R 7 and R 8 may be bonded to each other to form a carbocyclic ring having 3 to 20 carbon atoms or a 5 to 12 membered heterocycle, R 9 and R 10 each independently represent H or an alkyl group having 1 to 6 carbon atoms, R 11 to R 16 each independently represent a halogen atom, an aliphatic hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, an alkoxyl group having 1 to 20 carbon atoms which may have a substituent, or an aromatic hydrocarbon group having 6 to 12 carbon atoms which may have a substituent, r1 is an integer of 2 to 20, the X 3 s each independently represent a divalent aromatic hydrocarbon group having 15 to 32 carbon atoms, the X 4 s each independently represent a divalent group containing one or more hydrocarbon rings or heterocycles, wherein the divalent group containing one or more hydrocarbon rngs or heterocycles is selected from the group consisting of the following structures: X 5 s each independently represent a divalent saturated heterocyclic group.
  2. 2 . A siloxane-based thermoplastic resin comprising a constituent unit derived from the siloxane block-containing diol compound according to claim 1 .
  3. 3 . A method for producing the composition according to claim 1 , comprising reacting (A) a cyclic siloxane compound represented by the following formula (1): wherein R 1 and R 2 are each independently an alkyl group which may have a substituent, an alkenyl group which may have a substituent, or an aryl group which may have a substituent, and n is an integer of 3 to 30, and/or a linear siloxane compound represented by the following formula (2): wherein R 3 and R 4 are each independently an alkyl group which may have a substituent, an alkenyl group which may have a substituent, or an aryl group which may have a substituent, the Xs each independently represent a hydrogen atom, a hydroxyl group, an alkoxy group having 1 to 10 carbon atoms which may have a substituent, a siloxy group having 1 to 10 carbon atoms which may have a substituent, a hydrocarbon group having 1 to 10 carbon atoms which may have a substituent, an oxygen atom-containing group having 1 to 10 carbon atoms which may have a substituent, a nitrogen atom-containing group having 1 to 10 carbon atoms which may have a substituent, or an amino group which may have a substituent, and m is an integer of 2 to 10000, and (B) a diol compound represented by the following formulae (J 1 ) to (J 5 ): wherein A 1 and A 2, X 1 to X 5 , R 3 to R 5, and p1 to p2, are the same as defined in claim 1 , and (C) a basic compound catalyst.
  4. 4 . A method for producing a siloxane-based thermoplastic resin, comprising a reacting the composition according to claim 1 with a thermoplastic resin at 160 to 400° C. in the presence of a catalyst.

Description

TECHNICAL FIELD The present invention relates to a composition and a siloxane-based thermoplastic resin using the same, and a method for producing the same. BACKGROUND ART Conventionally, it has been known that a siloxane block-containing diol compound is effective as various resin raw materials containing a silicon block in a structure, and for example, the siloxane block-containing diol compound is used for applications such as a release layer in photocopying, a photoresist material, a plasticizer for polycarbonate, a component of a powder surface coating system, and the like. When the siloxane block-containing diol compound having a hydroxy group at the terminal is copolymerized with poly carbonate, for example, the siloxane block-containing diol compound can impart functions such as chemical resistance, low-temperature impact resistance, weather resistance, flame retardancy, and the like to polycarbonate. As such a siloxane block-containing diol compound, Patent Document 1 describes that siloxane block-containing diol compounds (hydroxyaryl-terminated polysiloxanes) represented by the following formulas (a) to (c) are preferable. Patent Document 1 describes that a polydiorganosiloxane-polyorganoblock copolymer is produced by a solvent-free melting method by adding a predetermined inorganic salt and/or organic salt to the siloxane block-containing diol compound as described above, thereby improving the melt stability, decomposition stability to a solvent and water, and low-temperature impact resistance of the resulting copolymer, and the like. PRIOR ART DOCUMENTS Patent Document 1: JP 2016-538362 A SUMMARY OF INVENTION Problems to Be Solved by the Invention However, it has been found that the siloxane block-containing diol compound described in Patent Document 1 as described above has low reactivity between a siloxane compound and a diol compound as a raw material, and may be difficult to industrially produce. Therefore, the present invention provides a composition containing a siloxane block-containing diol compound that is easy to industrially produce. Means for Solving the Problems The present inventors have conducted intensive studies to solve the above problem. As a result, the present inventors have found that the above problem can be solved by forming a siloxane block-containing diol compound into a predetermined structure, and have completed the present invention. That is, the present invention is, for example, as follows. [1] A composition comprising a siloxane block-containing diol compound, whereinthe siloxane block-containing diol compound is represented by the following formula (I): whereinR1 and R2 are each independently an alkyl group having 1 to 20 carbon atoms which may have a substituent, or an aryl group having 6 to 30 carbon atoms which may have a substituent,m is an integer of 1 to 25,n is an integer of 3 to 200,Xs each independently represent any of the following formulae (I1) to (I6): whereinA1 and A2 are each independently —(CR6AR6B)q1— or —(O—(CR6AR6B)q2)q3—, wherein R6A and R6B are each independently H or an alkyl group having 1 to 6 carbon atoms, q1 is an integer of 0 to 10, q2 is an integer of 0 to 10, and q3 is an integer of 0 to 10,R3 and R4 each independently represent a halogen atom, an aliphatic hydrocarbon group having 1 to 20 carbon atoms, an alkoxyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, an aralkyl group having 7 to 20 carbon atoms, an aromatic hydrocarbon-oxy group having 6 to 20 carbon atoms, or a cycloalkoxyl group having 3 to 20 carbon atoms,p1 and p2 are each independently an integer of 0 to 4,R5s each independently represent H or an alkyl group having 1 to 6 carbon atoms,X1 and X2 are each independently a single bond or a group shown below: wherein R7 and R8 are each independently H, a halogen atom, an aliphatic hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, an alkoxyl group having 1 to 20 carbon atoms which may have a substituent, or an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent, or R7 and R8 may be bonded to each other to form a carbocyclic ring having 3 to 20 carbon atoms or a 5 to 12 membered heterocycle, R9 and R10 each independently represent H or an alkyl group having 1 to 6 carbon atoms, R11 to R16 each independently represent a halogen atom, an aliphatic hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, an alkoxyl group having 1 to 20 carbon atoms which may have a substituent, or an aromatic hydrocarbon group having 6 to 12 carbon atoms which may have a substituent, r1 is an integer of 2 to 20,X3s each independently represent a divalent aromatic hydrocarbon group having 15 to 32 carbon atoms,X4s each independently represent a divalent group containing one or more hydrocarbon rings or heterocycles, wherein the divalent group containing one or more hydrocarbon