Polycarbodiimide composition, method for producing a polycarbodiimide composition, water-dispersed composition, solution composition, resin composition, and cured resin

Patent metadata

Field	Value
Publication number	US-11390751-B2
Application number	US-201716485811-A
Country	US
Kind code	B2
Filing date	Jun 20, 2017
Priority date	Feb 16, 2017
Publication date	Jul 19, 2022
Grant date	Jul 19, 2022

Abstract

The polycarbodiimide composition is a reaction product of polyisocyanate having a primary isocyanate group with alcohol, wherein the alcohol contains at least one oxyethylene-containing alcohol containing an oxyethylene group, and at least one oxyethylene-noncontaining alcohol containing no oxyethylene group, the at least one oxyethylene-noncontaining alcohol has a solubility parameter of 11.20 (cal/cm3)1/2 or less.

First claim

The invention claimed is:

1. A polycarbodiimide composition of
a reaction product of polyisocyanate having a primary isocyanate group with alcohol,
wherein the alcohol contains
at least one oxyethylene-containing alcohol containing an oxyethylene group, and
at least one oxyethylene-noncontaining alcohol containing no oxyethylene group,
the at least one oxyethylene-noncontaining alcohol has a solubility parameter of 11.20 (cal/cm 3 ) 1/2 or less, and
the oxyethylene-noncontaining alcohol having the solubility parameter of 11.20 (cal/cm 3 ) 1/2 or less is
at least one selected from the group consisting of isobutanol, 2-butanol, 2-methyl-1-butanol, 2,2-dimethyl-1-propanol, 3-methoxy-1-butanol, 1-octanol, 2-ethyl-1-hexanol, and 1-dodecanol.

2. The polycarbodiimide composition according to claim 1 , wherein
the oxyethylene group content relative to the polycarbodiimide composition is 10 mass % or more and 35 mass % or less.

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

4. The polycarbodiimide composition according to claim 1 , wherein
the polyisocyanate is pentamethylene diisocyanate.

5. A method for producing a polycarbodiimide composition, the method including the steps of:
a urethane-forming step, in which polyisocyanate having a primary isocyanate group and alcohol are subjected to urethane-forming reaction, and
a carbodiimide-forming step, in which the reaction product in the urethane-forming step is heated in the presence of a carbodiimide-forming catalyst to cause carbodiimide-forming reaction,
wherein
the alcohol contains
at least one oxyethylene-containing alcohol containing an oxyethylene group, and
at least one oxyethylene-noncontaining alcohol containing no oxyethylene group,
the at least one oxyethylene-noncontaining alcohol has a solubility parameter of 11.20 (cal/cm 3 ) 1/2 or less, and
the oxyethylene-noncontaining alcohol having the solubility parameter of 11.20 (cal/cm 3 ) 1/2 or less is
at least one selected from the group consisting of isobutanol, 2-butanol, 2-methyl-1-butanol, 2,2-dimethyl-1-propanol, 3-methoxy-1-butanol, 1-octanol, 2-ethyl-1-hexanol, and 1-dodecanol.

6. The method for producing a polycarbodiimide composition according to claim 5 , wherein
the equivalent ratio (NCO/OH) of the isocyanate group in the polyisocyanate relative to the hydroxyl group in the alcohol is more than 2 and 10 or less.

7. A water-dispersed composition, being
an dispersion in which the polycarbodiimide composition according to claim 1 is dispersed in water with a solid content concentration of 5 mass % or more and 90 mass % or less.

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

9. A resin composition comprising
a first agent having a carboxyl group, and
a second agent containing the polycarbodiimide composition according to claim 1 .

10. A cured resin, being
a cured product of the resin composition according to claim 9 .

Assignees

• Mitsui Chemicals Inc

Inventors

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

Classifications

• C08K5/29

  Compounds containing {one or more} carbon-to-nitrogen double bonds · CPC title

• C08G18/282 Primary

  Alkanols, cycloalkanols or arylalkanols including terpenealcohols · CPC title

• C08G18/28

  characterised by the compounds used containing active hydrogen · CPC title

• C08G18/73

  acyclic · CPC title

• C08G18/095 Primary

  oligomerisation to carbodiimide or uretone-imine groups · CPC title