Hybrid polyurethane-polyhydroxyurethane composition

Patent metadata

Field	Value
Publication number	US-12012477-B2
Application number	US-201917281766-A
Country	US
Kind code	B2
Filing date	Sep 27, 2019
Priority date	Oct 4, 2018
Publication date	Jun 18, 2024
Grant date	Jun 18, 2024

Abstract

The present invention relates to a hybrid polyurethane-polyhydroxyurethane (PU-PHU) composition 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, resulting in the formation of at least one prepolymer, (ii) Reacting said at least one prepolymer with at least one cyclic carbonate functional group containing compound, leading to the formation of a cyclic carbonate-terminated prepolymer, (iii) Ring-opening reaction of said cyclic carbonate-terminated prepolymer with at least one amine functional group containing compound resulting in said hybrid PU-PHU composition,

characterised in that said ring-opening reaction step is carried out above room temperature, preferably above 20° C., more preferably above 25° C.

First claim

The invention claimed is:

1. A method of making a hybrid polyurethane-polyhydroxyurethane (PU-PHU) composition 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, resulting in the formation of at least one prepolymer,
(ii) reacting said at least one prepolymer with at least one cyclic carbonate functional group containing compound, leading to the formation of a cyclic carbonate-terminated prepolymer, wherein the at least one cyclic carbonate functional group containing compound comprises one or more of: 4-(mercaptomethyl)-1,3-dioxolan-2-one, 4-((methylamino)methyl)-1,3-dioxolan-2-one, 4-(aminomethyl)-1,3-dioxolan-2-one, and 2-(2-oxo-1,3-dioxolan-4-yl)acetic acid, and
(iii) performing a ring-opening reaction of said cyclic carbonate-terminated prepolymer with at least one amine functional group containing compound above room temperature resulting in said hybrid PU-PHU composition.

2. The method according to claim 1 , wherein the amine of said at least one amine functional group containing compound has a functionality of at least 1.8.

3. The method according to claim 1 , wherein the temperature at which said ring-opening reaction step is carried out ranges from 25° C. to 160° C.

4. The method according to claim 1 , wherein said at least one isocyanate-reactive compound has a number average molecular weight equal to or higher than 62.

5. The method according to claim 1 , wherein step (ii) is carried out at a molar ratio of said at least one prepolymer to said at least one cyclic carbonate functional group containing compound (NCO:OH) ranging from 0.5 to 1.05.

6. The method according to claim 1 , wherein said at least one prepolymer has an NCO value ranging from 0.8 to 25%.

7. The method according to claim 1 , wherein step (ii) is performed at a temperature ranging from 50° C. to 150° C.

8. The method according to claim 1 , wherein step (ii) is carried out in a solvent free condition.

9. The method according to claim 1 , wherein step (ii) and/or step (iii) is carried out in presence of a catalyst 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, and mixtures thereof.

10. The method according to claim 1 , wherein said at least one cyclic carbonate functional group containing compound further comprises glycerol carbonate.

11. The method according to claim 1 , wherein step (iii) is achieved in a period of time of up to 3 hours.

12. The method according to claim 1 , wherein the conversion of the cyclic carbonate-terminated prepolymer of step (iii) is of at least 90.

13. A product comprising a PU-PHU composition made according to claim 1 .

14. A method for processing a thermoset hybrid PU-PHU product, wherein the method comprises the following steps:
providing a cured thermoset hybrid PU-PHU product made by the process according to claim 1 , which product has an outer surface;
processing said cured thermoset hybrid PU-PHU product by applying at least one stimulus, onto said outer surface, at a predetermined temperature and/or for a predetermined period of time; and
obtaining a processed hybrid PU-PHU product.

15. A method of making a hybrid polyurethane-polyhydroxyurethane (PU-PHU) composition 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, resulting in the formation of at least one prepolymer, the
(ii) reacting said at least one prepolymer with at least one cyclic carbonate functional group containing compound, leading to the formation of a cyclic carbonate-terminated prepolymer, wherein the at least one cyclic carbonate functional group containing compound comprises a 4-membered cyclic carbonate and/or a 6-membered cyclic carbonate, and
(iii) performing a ring-opening reaction of said cyclic carbonate-terminated prepolymer with at least one amine functional group containing compound above room temperature resulting in said hybrid PU-PHU composition.

16. The method according to claim 15 , wherein said at least one cyclic carbonate functional group containing compound further comprises glycerol carbonate.

17. The method according to claim 1 , wherein the temperature at which said ring-opening reaction step is carried out ranges from 100° C. to 160° C.

Assignees

• Huntsman Int Llc

Inventors

• Chuang Ya-Mi
• Martini Giulio
• Phanopoulos Christopher

Classifications

• C08G18/7671

  containing only one alkylene bisphenyl group · CPC title

• C08G18/4825 Primary

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

• C08G18/3819

  having nitrogen · CPC title

• C08G18/284

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

• C08G71/04

  Polyurethanes · CPC title