1,4-bis(isocyanatomethyl)cyclohexane, polyisocyanate composition, polyurethane resin, molded article, eyewear material, eyewear frame, and lens

Patent metadata

Field	Value
Publication number	US-9475903-B2
Application number	US-201414443774-A
Country	US
Kind code	B2
Filing date	Sep 25, 2014
Priority date	Sep 26, 2013
Publication date	Oct 25, 2016
Grant date	Oct 25, 2016

Abstract

1,4-bis(isocyanatomethyl)cyclohexane contains 70 mol % or more and 95 mol % or less of a trans isomer relative to a total amount of a cis isomer and the trans isomer, and 0.1 ppm or more and 300 ppm or less of the compound represented by formula (1) below:

First claim

The invention claimed is:

1. A 1,4-bis(isocyanatomethyl)cyclohexane composition comprising 1,4-bis(isocyanatomethyl)cyclohexane and a compound represented by formula (1) below, wherein:
the 1,4-bis(isocyanatomethyl)cyclohexane contains a trans isomer of 1,4-bis(isocyanatomethyl)cyclohexane and a cis isomer of 1,4-bis(isocyanatomethyl)cyclohexane, and comprises 70 mol % or more and 95 mol % or less of the trans isomer relative to a total amount of the cis isomer and the trans isomer, and
the 1,4-bis(isocyanatomethyl)cyclohexane composition contains 0.1 ppm or more and 300 ppm or less of the compound represented by formula (1) below:

2. The 1,4-bis(isocyanatomethyl)cyclohexane composition according to claim 1 , wherein the 1,4-bis(isocyanatomethyl)cyclohexane comprises 80 mol % or more and 93 mol % or less of the trans isomer relative to a total amount of the cis isomer and the trans isomer.

3. A polyisocyanate composition produced by modifying the 1,4-bis(isocyanatomethyl)cyclohexane composition according to claim 1 ,
and comprising at least one functional group of (a) to (e) below:
(a) an isocyanurate group obtained by trimerizing the 1,4-bis(isocyanatomethyl)cyclohexane,
(b) an allophanate group obtained by allowing the 1,4-bis(isocyanatomethyl)cyclohexane and a monoalcohol to react, and then further subjecting them to an allophanate-forming reaction,
(c) a biuret group obtained by allowing the 1,4-bis(isocyanatomethyl)cyclohexane to react with at least one selected from the group consisting of water, tertiary alcohol and secondary amine, and then further subjecting them to a biuretization reaction,
(d) a urethane group obtained by allowing the 1,4-bis(isocyanatomethyl)cyclohexane to react with a polyol component, and
(e) a urea group obtained by allowing the 1,4-bis(isocyanatomethyl)cyclohexane to react with water and/or a polyamine component.

4. A polyurethane resin produced by allowing a polyisocyanate component to react with an active hydrogen group-containing component, wherein the polyisocyanate component comprises the 1,4-bis(isocyanatomethyl)cyclohexane composition according to claim 1 ,
and/or
a polyisocyanate-modified composition produced by modifying the 1,4-bis(isocyanatomethyl)cyclohexane composition according to claim 1 , and comprising at least one functional group of (a) to (e) below:
(a) an isocyanurate group obtained by trimerizing the 1,4-bis(isocyanatomethyl)cyclohexane,
(b) an allophanate group obtained by allowing the 1,4-bis(isocyanatomethyl)cyclohexane and a monoalcohol to react, and then further subjecting them to an allophanate-forming reaction,
(c) a biuret group obtained by allowing the 1,4-bis(isocyanatomethyl)cyclohexane to react with at least one selected from the group consisting of water, tertiary alcohol and secondary amine, and then further subjecting them to a biuretization reaction,
(d) a urethane group obtained by allowing the 1,4-bis(isocyanatomethyl)cyclohexane to react with a polyol component, and
(e) a urea group obtained by allowing the 1,4-bis(isocyanatomethyl)cyclohexane to react with water and/or a polyamine component.

5. A molded article produced from the polyurethane resin according to claim 4 .

6. Fiber produced from the polyurethane resin according to claim 4 .

7. A fabric obtained by using the fiber according claim 6 in at least a part thereof.

8. Nonwoven fabric obtained by using the polyurethane resin according to claim 4 in at least a part thereof.

9. Film produced from the polyurethane resin according to claim 4 .

10. A sheet produced from the polyurethane resin according to claim 4 .

11. Apparel obtained by using the fiber according claim 6 in at least a part thereof.

12. Apparel obtained by using the fabric according claim 7 in at least a part thereof.

13. Apparel obtained by using the nonwoven fabric according claim 8 in at least a part thereof.

14. Apparel obtained by using the film according claim 9 in at least a part thereof.

15. Apparel obtained by using the sheet according claim 10 in at least a part thereof.

16. Apparel according to claim 11 , which is at least one selected from the group consisting of swimwear, compression wear, and underwear.

17. Apparel according to claim 12 , which is at least one selected from the group consisting of swimwear, compression wear, and underwear.

18. Apparel according to claim 13 , which is at least one selected from the group consisting of swimwear, compression wear, and underwear.

19. Apparel according to claim 14 , which is at least one selected from the group consisting of swimwear, compression wear, and underwear.

20. Apparel according to claim 15 , which is at least one selected from the group consisting of swimwear, compression wear, and underwear.

Assignees

• Mitsui Chemicals Inc

Inventors

• Yamasaki Satoshi
• Morita Hirokazu
• Kuwamura Goro
• Nishiguchi Daisuke
• Nakagawa Toshihiko
• Hasegawa Daisuke
• Hamada Tetsuya
• Kiyono Shinji
• Fukuda Takeshi
• Kosumi Kazuhiro
• Tsukada Hidetaka
• Goto Kenichi
• Ito Shinsuke
• Kakinuma Naoyuki

Classifications

• C08J2375/04

  Polyurethanes · CPC title

• Y10T442/60

  Nonwoven fabric [i.e., nonwoven strand or fiber material] · CPC title

• A47D1/00

  Children's chairs · CPC title

• C07D295/06

  substituted by halogen atoms or nitro radicals · CPC title

• G02C5/008

  Spectacles frames characterized by their material, material structure and material properties · CPC title