Polycarbonate polyol and polyurethane

Patent metadata

Field	Value
Publication number	US-11608405-B2
Application number	US-201916448007-A
Country	US
Kind code	B2
Filing date	Jun 21, 2019
Priority date	Dec 22, 2016
Publication date	Mar 21, 2023
Grant date	Mar 21, 2023

Abstract

Provided is a polycarbonate polyol used as a raw material of a polyurethane that has an excellent balance of flexibility, mechanical strength and solvent resistance. The polycarbonate polyol includes structural units derived from a polyhydric alcohol and has a hydroxyl value of 20 to 450 mg KOH/g. The polyhydric alcohol includes: a diol (A) containing not less than 70% by weight of a specific oxyalkylene glycol (A1); and a trihydric to hexahydric branched alcohol (B) having 3 to 12 carbon atoms. In the polycarbonate polyol, structural units derived from the branched alcohol (B) is contained in an amount of 0.005 to 5.0% by mole in the structural units derived from the polyhydric alcohol. A ratio of a structural unit (X1) represented by the following Formula (X1) in the structural units derived from the branched alcohol (B) is not higher than 50% by mole.

First claim

What is claimed is:

1. A polycarbonate polyol comprising structural units derived from a polyhydric alcohol and having a hydroxyl value of 20 mg KOH/g to 450 mg KOH/g, wherein
the polycarbonate polyol is produced by a transesterification reaction of the polyhydric alcohol with a carbonate compound,
the polyhydric alcohol comprises a diol (A) and a trihydric to hexahydric branched alcohol (B), comprising a partial structure (B2) represented by the following Formula (B2), having 4 to 12 carbon atoms,
the diol (A) comprises an oxyalkylene glycol (A1) represented by the following Formula (A1) in an amount of 70% by weight or higher based on total weight of diol (A),
a ratio of structural units derived from the branched alcohol (B) is 0.005% by mole to 5.0% by mole with respect to a total amount of the structural units derived from the polyhydric alcohol, and
a ratio of a structural unit (X2) represented by the following Formula (X2) in the structural units derived from the branched alcohol (B) is not higher than 50% by mole based on the total moles of structural units derived from the branched alcohol (B):

wherein, m represents an integer of 2 to 4; R A1 represents a carbon chain optionally containing a branch having 2 to 5 carbon atoms; and m R A1 s contained in Formula (A1) are the same or different

2. The polycarbonate polyol according to claim 1 , wherein the branched alcohol (B) is a trihydric alcohol.

3. The polycarbonate polyol according to claim 2 , wherein the trihydric alcohol is trimethylolpropane.

4. The polycarbonate polyol according to claim 1 , wherein the oxyalkylene glycol (A1) comprises at least one selected from the group consisting of diethylene glycol, triethylene glycol, tetraethylene glycol, and dipropylene glycol.

5. The polycarbonate polyol according to claim 4 , wherein the oxyalkylene glycol (A1) comprises diethylene glycol and/or triethylene glycol.

6. The polycarbonate polyol according to claim 5 , wherein a total content ratio of diethylene glycol and triethylene glycol in the diol (A) is not less than 70% by weight.

7. The polycarbonate polyol according to claim 5 , wherein a weight ratio of diethylene glycol and triethylene glycol in the oxyalkylene glycol (A1) is 10:90 to 90:10 (diethylene glycol:triethylene glycol).

8. A polyurethane obtainable by reacting the polycarbonate polyol according to claim 1 with a compound comprising isocyanate groups.

9. A polyurethane, obtainable by reacting a polycarbonate polyol with a compound comprising isocyanate groups, wherein
the polycarbonate polyol comprises structural units derived from a polyhydric alcohol and has a hydroxyl value of 20 mg KOH/g to 450 mg KOH/g,
the polycarbonate polyol is produced by a transesterification reaction of the polyhydric alcohol with a carbonate compound,
the polyhydric alcohol comprises a diol (A) and a trihydric to hexahydric branched alcohol (B), comprising a partial structure (B2) represented by the following Formula (B2), having 4 to 12 carbon atoms,
the diol (A1) comprises an oxyalkylene glycol (A1) represented by the following Formula (A1) and a content ratio of the oxyalkylene glycol (A1) in the diol (A) is 70% by weight or higher,
a ratio of structural units derived from the branched alcohol (B) in the polycarbonate polyol is 0.005% by mole to 5.0% by mole, the ratio being with respect to a total amount of the structural units derived from the polyhydric alcohol in the polycarbonate polyol, and
a ratio of a structural unit (X2) represented by the following Formula (X2) in the structural units derived from the branched alcohol (B) is not higher than 50% by mole based on the total moles of structural units derived from the branched alcohol (B:

wherein, in represents an integer of 2 to 4; R A1 represents a carbon chain optionally containing a branch having 2 to 5 carbon atoms; and in R A1 s contained in Formula (A1) are the same or different

10. The polyurethane according to claim 9 , which is obtainable by reacting the polycarbonate polyol, an organic polyisocyanate compound, and a chain extender.

Assignees

• Mitsubishi Chem Corp

Inventors

• Hioki Yuta
• Kanamori Yoshikazu
• Kusano Kazunao
• Wakabayashi Kazuki
• Yamashita Ryo
• Yamanaka Takayuki

Classifications

• C08G18/3206

  aliphatic · CPC title

• C07C31/20

  Dihydroxylic alcohols · CPC title

• C08G18/6637

  with compounds of group C08G18/32 or polyamines of C08G18/38 · CPC title

• C08G64/02

  Aliphatic polycarbonates · CPC title

• C08G18/7671

  containing only one alkylene bisphenyl group · CPC title