Oxazolidinedione-terminated prepolymer

Patent metadata

Field	Value
Publication number	US-12065530-B2
Application number	US-201917273193-A
Country	US
Kind code	B2
Filing date	Sep 5, 2019
Priority date	Sep 10, 2018
Publication date	Aug 20, 2024
Grant date	Aug 20, 2024

Abstract

The present invention relates to a compound obtained by a process comprising the following steps: (i) Reacting at least one isocyanate containing compound, in stoichiometric excess, with at least one isocyanate-reactive compound having a number average molecular weight equal to or higher than 400, resulting in the formation of at least one prepolymer having soft blocks and hard blocks in its structure, which prepolymer contains unreacted isocyanate monomer, (ii) Reacting said at least one prepolymer with a hydroxyl-ester compound or a hydroxyl-acid compound with the formation of hydroxyl-ester terminated prepolymer or hydroxyl-acid terminated prepolymer, and Ring-closing said hydroxyl-ester terminated prepolymer or hydroxyl-acid terminated prepolymer; (iii) Formation of said compound made of oxazolidinedione-terminated prepolymer and oxazolidinedione-terminated monomer, which is soluble in said oxazolidinedione-terminated prepolymer.

First claim

The invention claimed is:

1. A compound obtained by a process comprising the following steps:
(i) Reacting at least one isocyanate containing compound, in stoichiometric excess, with at least one isocyanate-reactive compound having a number average molecular weight equal to or higher than 400, resulting in the formation of at least one prepolymer having soft blocks and hard blocks in its structure, which prepolymer contains unreacted isocyanate monomer,
(ii) Reacting said at least one prepolymer with a hydroxyl-ester compound or a hydroxyl-acid compound to form a hydroxyl-ester terminated prepolymer or hydroxyl-acid terminated prepolymer, wherein the hydroxyl-ester terminated prepolymer contains hydroxyl-ester terminated monomer and the hydroxyl-acid terminated prepolymer contains hydroxyl-acid terminated monomer, and
(iii) Ring-closing said hydroxyl-ester terminated prepolymer or hydroxyl-acid terminated prepolymer by processing said hydroxyl-ester terminated prepolymer or hydroxyl-acid terminated prepolymer in the presence of at least one catalyst to form a compound made of oxazolidinedione-terminated prepolymer and oxazolidinedione-terminated monomer, wherein the oxazolidinedione-terminated monomer is soluble in the oxazolidinedione-terminated prepolymer.

2. The compound according to claim 1 , having a non-Newtonian viscosity.

3. The compound according to claim 1 , wherein said at least one prepolymer of step (i) has a non-Newtonian viscosity.

4. The compound according to claim 1 , wherein said at least one isocyanate containing compound and said at least one isocyanate-reactive compound are reacted at a molar ratio (NCO:OH) ranging from 1.05 to 15.

5. The compound according to claim 1 , wherein said at least one prepolymer and said at least one hydroxyl-ester compound or said hydroxyl-acid compound are reacted at a molar ratio (NCO:OH) ranging from 0.5 to 1.2.

6. The compound according to claim 1 , wherein said at least one prepolymer has an NCO value ranging from 0.8 to 10%, before performing step (ii).

7. The compound according to claim 1 , wherein step (ii) is performed at a first temperature, resulting in the formation of said hydroxyl-ester terminated prepolymer or a hydroxyl-acid terminated prepolymer.

8. The compound according to claim 7 , wherein step (ii) is carried out, at said first temperature, in a catalyst free condition.

9. The compound according to claim 7 , wherein said ring-closure step is carried out at a second temperature.

10. The compound according to claim 9 , wherein said catalyst is selected from the group consisting of 1,4-Diazabicyclo[2.2.2]octane (DABCO); 1,8-Diazabicyclo(5.4.0)undec-7-ene (DBU); Triazabicyclodecene (TBD); triethylamine; and potassium t-butanoate, or combination thereof.

11. The compound according to claim 1 , wherein said hydroxyl-ester compound is selected from the group consisting of alpha-hydroxy ester compounds, beta-hydroxy ester compounds, hydroxyl containing esters derived from fatty acids, natural oils containing hydroxyl groups, or combinations thereof.

12. The compound according to claim 1 , wherein said at least one prepolymer of step (i) has a hard block content ranging from 20 to 35 wt. %, based on the total weight of said at least one prepolymer.

13. The compound according to claim 1 , having a hard block content ranging from 30 to 55 wt. %, based on the total weight of the compound.

14. A poly(urethane-amide) compound obtained by reacting a compound obtained according to claim 1 , with at least one amine having a functionality of at least 1.8 and a hard block content ranging from at least 15% to 85%.

15. A product comprising poly(urethane-amide) compound according to claim 14 .

Assignees

• Huntsman Int Llc

Inventors

• Chuang Ya-Mi
• Marini Giulio
• Phanopoulos Christopher

Classifications

• C08G18/7671 Primary

  containing only one alkylene bisphenyl group · CPC title

• C08G18/4825

  Polyethers containing two hydroxy groups (C08G18/4833 - C08G18/5096 take precedence) · CPC title

• C08G18/325

  containing secondary or tertiary amino groups (C08G18/3228, C08G18/3234, C08G18/3246 take precedence) · CPC title

• C08G18/284

  Compounds containing ester groups, e.g. oxyalkylated monocarboxylic acids · CPC title

• C08G18/2081

  containing at least two non-condensed heterocyclic rings · CPC title