Polycarbodiimide composition, method for producing polycarbodiimide composition, aqueous dispersion composition, solution composition, resin composition, and cured resin

Patent metadata

Field	Value
Publication number	US-10011677-B2
Application number	US-201715576204-A
Country	US
Kind code	B2
Filing date	Jan 5, 2017
Priority date	Jan 5, 2016
Publication date	Jul 3, 2018
Grant date	Jul 3, 2018

Abstract

A polycarbodiimide composition is a reaction product of polyisocyanate having a primary isocyanate group and alcohols, wherein in an infrared absorption spectrum, the intensity ratio (IR CI /IR UI+U ) of absorbance IR CI at or near 2120 cm −1 due to stretching vibration of the carbodiimide group relative to absorbance IR UI+U at or near 1720 cm −1 due to stretching vibration of the uretonimine group and urethane group is 1.5 or more and 4.5 or less.

First claim

The invention claimed is:

1. A polycarbodiimide composition comprising:
a reaction product of polyisocyanate having a primary isocyanate group and alcohols,
wherein the polycarbodiimide composition includes a carbodiimide group and a uretonimine group,
in an infrared absorption spectrum, the intensity ratio (IR CI /IR UI+U ) of absorbance IR CI at or near 2120 cm −1 due to stretching vibration of the carbodiimide group relative to absorbance IR UI+U at or near 1720 cm −1 due to stretching vibration of the uretonimine group and urethane group is 1.5 or more and 4.5 or less, and
the equivalent ratio (NCO/OH) of the isocyanate group of polyisocyanate relative to the hydroxyl group of the alcohols is more than 2 and 16 or less.

2. The polycarbodiimide composition according to claim 1 , wherein in the polycarbodiimide composition, the proportion of the uretonimine group relative to a total mol of the carbodiimide group and the uretonimine group is 1.5 mol % or more and 15 mol % or less.

3. The polycarbodiimide composition according to claim 1 , wherein the alcohols contain an alcohol containing three or more consecutive oxyethylene groups, and 10 mass % or more and 40 mass % or less of the three or more consecutive oxyethylene groups is contained relative to the polycarbodiimide composition.

4. The polycarbodiimide composition according to claim 1 , wherein the alcohols contain an alcohol containing three or more consecutive oxyethylene groups, and 5 mol % or more and 50 mol % or less of the alcohol containing three or more consecutive oxyethylene groups is contained relative to a total mol of the alcohols.

5. The polycarbodiimide composition according to claim 1 , wherein the polyisocyanate is aliphatic polyisocyanate.

6. The polycarbodiimide composition according to claim 5 , wherein the aliphatic polyisocyanate is pentamethylene diisocyanate.

7. A method for producing the polycarbodiimide composition according to claim 1 , the method comprising the steps of:
a urethane-formation step, in which the polyisocyanate and the alcohols are subjected to urethane-forming reaction, and
a carbodiimide-formation step, in which the reaction product of the urethane-formation step is heated in the presence of a carbodiimide-formation catalyst to cause carbodiimide-formation reaction.

8. The method for producing a polycarbodiimide composition according to claim 7 , wherein the reaction temperature in the carbodiimide-formation reaction is 125° C. or more and 160° C. or less.

9. The method for producing a polycarbodiimide composition according to claim 7 , wherein the carbodiimide-formation reaction is performed while refluxing.

10. An aqueous dispersion composition, wherein the aqueous dispersion composition is an aqueous dispersion in which the polycarbodiimide composition according to claim 1 is dispersed in water at a ratio of a solid content concentration of 5 mass % or more and 90 mass % or less.

11. A solution composition, wherein the solution composition is a solution in which the polycarbodiimide composition according to claim 1 is dissolved in an organic solvent at a ratio of a solid content concentration of 5 mass % or more and 90 mass % or less.

12. A resin composition comprising a base component having a carboxyl group, and a curing agent including the polycarbodiimide composition according to claim 1 .

13. A cured resin, wherein the cured resin is a cured product of the resin composition according to claim 12 .

Assignees

• Mitsui Chemicals Inc

Inventors

• Yamashita Tatsuya
• Nakagawa Toshihiko
• Kiyono Shinji
• Nakagawa Aya
• Morita Hirokazu
• Mio Shigeru
• Yamasaki Satoshi
• Sakata Kazuki

Classifications

• C08G18/095 Primary

  oligomerisation to carbodiimide or uretone-imine groups · CPC title

• C09D175/04

  Polyurethanes · CPC title

• C07B61/00

  Other general methods · CPC title

• C08G18/168

  Organic compounds · CPC title

• C08G18/283

  Compounds containing ether groups, e.g. oxyalkylated monohydroxy compounds · CPC title