IP Library › Granted Patent US 12,180,335
Granted Patent B2
US 12,180,335 · App. 17/614,772 · Granted Dec 31, 2024

Polycarbonate diol derived from ether diol of anhdrohexitol and preparation method thereof, and polyurethane prepared therefrom and adhesive comprising the same

Inventors: Jun Seop Im (Hwaseong-si, KR); Seung Hyun Yoo (Daejeon, KR); Hoon Ryu (Daejeon, KR); Won Hyun Jeon (Seoul, KR)
Assignee: SAMYANG CORPORATION
C08G64/30C08G18/10C08G18/44C08G18/7671C08G64/02C09D175/06C09J175/06
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Quick Facts
Patent No.
US 12,180,335
App. No.
17/614,772
Granted
Dec 31, 2024
Kind
B2
Abstract

A polycarbonate diol is derived from ether diol of anhydrohexitol, a preparation method thereof, a polyurethane prepared therefrom, and adhesive, etc. including the same. More specifically, the polycarbonate diol includes repeated units derived from ether diol of anhydrohexitol; and carbonate diester; and optionally anhydrohexitol; and thereby showing better effect of improving color as compared with conventional polycarbonate diol, and being capable of providing polyurethane prepared therefrom with remarkably improved adhesion strength (T-peel strength or shear strength), preparation method thereof, polyurethane prepared therefrom, and adhesive, paint and coating agent including the same.

Claims (46)

1. A polycarbonate diol comprising:

(1) repeated units derived from ether diol of anhydrohexitol; and

(2) repeated units derived from carbonate diester,

wherein the polycarbonate diol is prepared by reacting a mixture comprising the ether diol of anhydrohexitol and the carbonate diester in the presence of a transesterification catalyst, and

wherein the amount of the ether diol of anhydrohexitol in the mixture is 30 to 95% by weight, based on total 100% by weight of the mixture.

2. A polycarbonate diol comprising:

(1) repeated units derived from ether diol of anhydrohexitol;

(2) repeated units derived from carbonate diester; and

(3) repeated units derived from anhydrohexitol,

wherein the polycarbonate diol is prepared by reacting a mixture comprising the ether diol of anhydrohexitol, the carbonate diester and the anhydrohexitol in the presence of a transesterification catalyst, and

wherein the amount of the ether diol of anhydrohexitol in the mixture is 5 to 60% by weight and the amount of the anhydrohexitol in the mixture is 10 to 45% by weight, based on total 100% by weight of the mixture.

3. The polycarbonate diol of claim 1 , wherein the anhydrohexitol is selected from isosorbide (1,4:3,6-dianhydrosorbitol), isomannide (1,4:3,6-dianhydromannitol), isoidide (1,4:3,6-dianhydroiditol) or mixtures thereof.

4. The polycarbonate diol of claim 1 , wherein the ether diol of anhydrohexitol is a product obtained by reacting anhydrohexitol and alkylene oxide.

5. The polycarbonate diol of claim 1 , wherein the ether diol of anhydrohexitol is a product obtained by reacting anhydrohexitol and ethylene carbonate.

6. The polycarbonate diol of claim 1 , wherein the carbonate diester is selected from dialkyl carbonate, diaryl carbonate, alkylene carbonate or combinations thereof.

7. The polycarbonate diol of claim 1 , further comprising repeated units derived from aliphatic diol.

8. The polycarbonate diol of claim 1 , comprising repeated units having a structure of the following formula 1:

wherein each of R 1 and R 2 is independently a linear or branched alkylene group having 2 to 20 carbons, and R 1 and R 2 may be the same or different from each other.

9. The polycarbonate diol of claim 2 , comprising repeated units having a structure of the following formula 1; and repeated units having a structure of the following formula 2:

wherein each of R 1 and R 2 is independently a linear or branched alkylene group having 2 to 20 carbons, and R 1 and R 2 may be the same or different from each other;

10. The polycarbonate diol of claim 7 , comprising repeated units having a structure of the following formula 3:

wherein R 3 is a linear or branched alkylene group having 2 to 10 carbons.

11. A method for preparing a polycarbonate diol, comprising a step of reacting a mixture comprising (i) ether diol of anhydrohexitol and (ii) carbonate diester, in the presence of a transesterification catalyst,

wherein the amount of the ether diol of anhydrohexitol in the mixture is 30 to 95% by weight, based on total 100% by weight of the mixture.

12. A method for preparing a polycarbonate diol, comprising a step of reacting a mixture comprising (i) ether diol of anhydrohexitol, (ii) carbonate diester and (iii) anhydrohexitol, in the presence of a transesterification catalyst,

wherein the amount of the ether diol of anhydrohexitol in the mixture is 5 to 60% by weight and the amount of the anhydrohexitol in the mixture is 10 to 45% by weight, based on total 100% by weight of the mixture.

13. The method for preparing a polycarbonate diol of claim 11 , wherein the mixture further comprises aliphatic diol.

14. A polyurethane comprising repeated units derived from the polycarbonate diol of claim 1 .

15. A method for preparing a polyurethane, comprising the steps of:

reacting a polyol component and a polyisocyanate component to prepare a prepolymer;

and reacting the prepolymer with a chain extender; the method being characterized in that the polyol component comprises the polycarbonate diol of claim 1 .

16. An adhesive comprising the polyurethane of claim 14 .

17. A paint comprising the polyurethane of claim 14 .

18. A coating agent comprising the polyurethane of claim 14 .

19. The polycarbonate diol of claim 2 , comprising repeated units having a structure of the following formula 3:

wherein R 3 is a linear or branched alkylene group having 2 to 10 carbons.

20. The polycarbonate diol of claim 2 , wherein the anhydrohexitol is selected from isosorbide (1,4:3,6-dianhydrosorbitol), isomannide (1,4:3,6-dianhydromannitol), isoidide (1,4:3,6-dianhydroiditol) or mixtures thereof.

21. The polycarbonate diol of claim 2 , wherein the ether diol of anhydrohexitol is a product obtained by reacting anhydrohexitol and alkylene oxide.

22. The polycarbonate diol of claim 2 , wherein the ether diol of anhydrohexitol is a product obtained by reacting anhydrohexitol and ethylene carbonate.

23. The polycarbonate diol of claim 2 , further comprising repeated units derived from aliphatic diol.

24. The method for preparing a polycarbonate diol of claim 12 , wherein the mixture further comprises aliphatic diol.

25. A polyurethane comprising repeated units derived from the polycarbonate diol of claim 2 .

26. A method for preparing a polyurethane, comprising the steps of: reacting a polyol component and a polyisocyanate component to prepare a prepolymer; and reacting the prepolymer with a chain extender; the method being characterized in that the polyol component comprises the polycarbonate diol of claim 2 .

27. An adhesive comprising the polyurethane of claim 25 .

28. A paint comprising the polyurethane of claim 25 .

29. A coating agent comprising the polyurethane of claim 25 .

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 1, 2022
From: IM, JUN SEOP; YOO, SEUNG HYUN; RYU, HOON; JEON, WON HYUN
To: SAMYANG CORPORATION
Reel/Frame 060245/0258 →
Priority Claims (2)
KR 10-2019-0064191 · May 31, 2019 · national
KR 10-2019-0065442 · Jun 3, 2019 · national
Continuity (1)
Related Publication 20220227927A1 · Jul 21, 2022