IP Library Granted Patent US 11,697,706
Granted Patent B2
US 11,697,706 · App. 17/049,046 · Granted Jul 11, 2023

Sealed isocyanates

Inventors: Benjamin R. Lund (Plano, TX); Walter Voit (Richardson, TX)
Assignees: Adaptive 3D Technologies; Board of Regents, The University of Texas System
C08G18/80B29C64/153B33Y10/00B33Y70/00C08F220/12C08G18/3855C08G18/672
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Quick Facts
Patent No.
US 11,697,706
App. No.
17/049,046
Granted
Jul 11, 2023
Kind
B2
Abstract

The present disclosure relates to sealed isocyanate resin compositions. The resin compositions may be used for additive manufacturing. One embodiment of the invention includes a photopolymerizable resin for additive manufacturing, the resin comprising: a blocked isocyanate; at least one monomer or oligomer; and a multifunctional nucleophile.

Claims (21)

1. A photopolymerizable resin for additive manufacturing, the resin comprising:

a blocked isocyanate;

30-90% by weight of one or more acrylic monomers; and

a multifunctional nucleophile;

wherein the resin is configured to react by exposure to light to form a cured material, and

wherein, after a post-cure heat treatment, the cured material has a strain capacity of between about 10% and about 500%.

2. The photopolymerizable resin according to claim 1 , further comprising one or more includes an a thiol monomers or -ene monomers.

3. The photopolymerizable resin according to claim 1 , wherein the multifunctional nucleophile includes at least one of a multifunctional alcohol, a multifunctional thiol, or a multifunctional amine.

4. The photopolymerizable resin according to claim 3 , wherein the multifunctional nucleophile includes a multifunctional thiol.

5. The photopolymerizable resin according to claim 4 , wherein the multifunctional thiol has a molecular weight greater than about 100 daltons.

6. The photopolymerizable resin according to claim 4 , wherein the resin includes about 1-20% of a multifunctional thiol.

7. The photopolymerizable resin according to claim 4 , wherein the multifunctional thiol includes a difunctional thiol.

8. The photopolymerizable resin according to claim 4 , wherein the multifunctional thiol includes a secondary thiol.

9. The photopolymerizable resin according to claim 8 , wherein the secondary thiol includes at least one of Pentaerythritol tetrakis (3-mercaptobutylate); 1,4-bis (3-mercaptobutylyloxy) butane; or 1,3,5-Tris(3-mercaptobutyloxethyl)-1,3,5,-triazine.

10. The photopolymerizable resin according to claim 1 , wherein the resin includes 1-70% of a blocked isocyanate.

11. The photopolymerizable resin according to claim 1 , wherein the blocked isocyanate includes at least one of a uretdione, a biuret, an allophanate, an isocyanaurate, methylene dicyclohexyl diisocyanate (MDI), or toluene diisocyanate (TDI).

12. The photopolymerizable resin according to claim 8 , wherein the uretdione is a uretdione of hexamethylene diisocyanate (HDI), a uretdione of isophorone diisocyanate (IDI), a uretdione of methylene dicyclohexyl diisocyanate (MDI), a uretdione of hydrogenated methylene dicyclohexyl diisocyanate (HMDI), or a uretdione of toluene diisocyanate (TDI).

13. The photopolymerizable resin according to claim 11 , wherein the isocyanaurate is an isocyanaurate of hexamethylene diisocyanate (HDI), an isocyanaurate of isophorone diisocyanate (IDI), an isocyanaurate of methylene dicyclohexyl diisocyanate (MDI), an isocyanaurate of hydrogenated methylene dicyclohexyl diisocyanate (HMDI), or an isocyanaurate of toluene diisocyanate (TDI).

14. The photopolymerizable resin according to claim 11 , wherein the biuret is a biuret of hexamethylene diisocyanate (HDI), a biuret of isophorone diisocyanate (IDI), a biuret of methylene dicyclohexyl diisocyanate (MDI), a biuret of hydrogenated methylene dicyclohexyl diisocyanate (HMDI), or a biuret of toluene diisocyanate (TDI).

15. The photopolymerizable resin according to claim 1 , wherein the blocked isocyanate includes an isocyanate and a blocking agent.

16. The photopolymerizable resin according to claim 15 , wherein the blocking agent includes at least one of a nucleophile, a derivative of an alcohol, a hindered amine, a caprolactam, a phenol, an oxime, or a pyrazole malonate.

Assignments (3)
SECURITY INTEREST Recorded Apr 24, 2026
From: ARC IMPACT ACQUISITION CORPORATION
To: IRON HORSE CREDIT LLC
Reel/Frame 075458/0351 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 19, 2023
From: LUND, BENJAMIN R.
To: ADAPTIVE 3D TECHNOLOGIES
Reel/Frame 062424/0765 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 27, 2022
From: VOIT, WALTER
To: BOARD OF REGENTS, THE UNIVERSITY OF TEXAS SYSTEM
Reel/Frame 061562/0916 →
Continuity (2)
Provisional Application 62660894 · Apr 20, 2018
Related Publication 20210189033A1 · Jun 24, 2021