Polysiloxazane compound, method for producing the same, and composition containing the same and cured product thereof

Patent metadata

Field	Value
Publication number	US-11339252-B2
Application number	US-202016749819-A
Country	US
Kind code	B2
Filing date	Jan 22, 2020
Priority date	Jan 29, 2019
Publication date	May 24, 2022
Grant date	May 24, 2022

Abstract

A polysiloxazane compound including a repeating unit of the following general formula (1), and having a number average molecular weight of 500 to 100,000 as measured by gel permeation chromatography versus polystyrene standards,wherein R1 and R2 each independently represent a substituted or unsubstituted C1-C50 monovalent hydrocarbon group optionally containing a hetero atom, Xs each independently represent a methyl group, an oxygen atom, NH—SiX2, or (NH)(3-r)/2—SiR1R2r (R1 and R2 have the same meaning as provided above), or Xs are joined to one another to represent an oxygen atom, n is an integer of 0 to 8, when the number of NH—SiX2 is denoted by p, p satisfies 0≤p/(2n+4)≤0.5, r is an integer of 0, 1, or 2, and a and b are numbers satisfying 0<a≤1, 0≤b<1, and a+b=1.

First claim

The invention claimed is:

1. A polysiloxazane compound comprising a repeating unit of the following general formula (1), and having a number average molecular weight of 500 to 100,000 as measured by gel permeation chromatography versus polystyrene standards,

wherein R 1 and R 2 each independently represent a substituted or unsubstituted C 1 -C 50 monovalent hydrocarbon group optionally containing a hetero atom, Xs each independently represent a methyl group, an oxygen atom , NH—SiX 2 , or (NH) (3-r)/2 —SiR 1 R 2 r (R 1 and R 2 have the same meaning as provided above), or Xs are joined to one another to represent an oxygen atom, n is an integer of 2 to 4, when the number of NH—SiX 2 is denoted by p, p satisfies 0<p/(2n+4)≤0.5, r is an integer of 0, 1, or 2, and a and b are numbers satisfying 0<a≤1, 0≤b<1, and a+b=1.

2. The polysiloxazane compound according to claim 1 , wherein the repeating unit has the following general formula (2):

wherein R 1 , R 2 , a, b, n, and r have the same meaning as provided above, Xs each independently represent a methyl group, NH—SiX 2 , or (NH) (3-r)/2 —SiR 1 R 2 r (R 1 and R 2 have the same meaning as provided above), and when the number of NH—SiX 2 is denoted by p, p satisfies 0<p/(2n+2)≤0.5.

3. The polysiloxazane compound according to claim 1 , wherein the repeating unit has the following general formula (3):

wherein R 1 , R 2 , a, b, n, and r have the same meaning as provided above, Xs each independently represent a methyl group or NH—SiX 2 , when the number of NH—SiX 2 is denoted by p, p satisfies 0<p/(2n+4)≤0.5.

4. The polysiloxazane compound according to claim 2 , wherein n in the general formula (2) is 2.

5. The polysiloxazane compound according to claim 3 , wherein n in the general formula (3) is 2.

6. A method for producing the polysiloxazane compound according to claim 1 , the method comprising:
a step of performing ammonolysis homopolymerization of a chlorosiloxane compound of the following general formula (4):

wherein n has the same meaning as provided above, Ys each independently represent a methyl group, a chlorine atom, or an oxygen atom, or Ys are joined to one another to represent an oxygen atom, and when the number of chlorine atoms is denoted by q, q satisfies 0<q/(2n+2)≤0.5, or
a step of mixing a chlorosiloxane compound of the general formula (4) and a chlorosilane compound of the following general formula (5):

wherein R 1 , R 2 , and r have the same meaning as provided above, and performing ammonolysis polymerization.

7. The method for producing a polysiloxazane compound according to claim 6 , further comprising a step of adding an alkaline aqueous solution and performing liquid-liquid separation after the ammonolysis polymerization.

8. The method for producing a polysiloxazane compound according to claim 6 , wherein the chlorosiloxane compound has the following general formula (6):

wherein n has the same meaning as provided above, Ys each independently represent a methyl group or a chlorine atom, and when the number of chlorine atoms is denoted by q, q satisfies 0<q/(2n+2)≤0.5.

9. The method for producing a polysiloxazane compound according to claim 6 , wherein the chlorosiloxane compound has the following general formula (7):

wherein n has the same meaning as provided above, Ys each independently represent a methyl group or a chlorine atom, and when the number of chlorine atoms is denoted by q, q satisfies 0<q/(2n+2)≤0.5.

10. The method for producing a polysiloxazane compound according to claim 8 , wherein n in the general formula (6) is 2.

11. The method for producing a polysiloxazane compound according to claim 9 , wherein n in the general formula (7) is 2.

12. A composition comprising the polysiloxazane compound according to claim 1 , and a solvent.

13. The composition according to claim 12 , wherein the composition is a primer.

14. A curable composition comprising the composition according to claim 13 , and at least one metal selected from the group consisting of titanium, aluminum, zinc, and tin.

15. A cured product obtaining by curing the curable composition according to claim 14 .

Assignees

• Shinetsu Chemical Co

Inventors

• Kawakami Masato
• Aoki Shotaro
• Kiyomori Ayumu

Classifications

• C08K2003/0812

  Aluminium · CPC title

• C08K2003/0881

  Titanium · CPC title

• C08K3/011

  Crosslinking or vulcanising agents, e.g. accelerators · CPC title

• C09D183/10

  Block or graft copolymers containing polysiloxane sequences (obtained by polymerising a compound having a carbon-to-carbon double bond on to a polysiloxane C09D151/08, C09D153/00) · CPC title

• C08G77/26 Primary

  nitrogen-containing groups · CPC title