IP Library Granted Patent US 10,324,978
Granted Patent B2
US 10,324,978 · App. 15/917,019 · Granted Jun 18, 2019

Composites formed from an absorptive filler and a polyurethane

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Quick Facts
Patent No.
US 10,324,978
App. No.
15/917,019
Granted
Jun 18, 2019
Kind
B2
Abstract

Composite materials and methods for their preparation are described herein. The composite materials can comprise a polyurethane and an absorptive filler. The polyurethane can be formed from the reaction of at least one isocyanate selected from the group consisting of diisocyanates, polyisocyanates, and combinations thereof, and one or more isocyanate-reactive monomers. The one or more isocyanate-reactive monomers can comprise at least one polyol and a first isocyanate-reactive monomer which includes one or more isocyanate-reactive functional groups and a moiety configured to associate with the absorptive filler.

Claims (36)

1. A continuous process for preparing a composite product, comprising:

mixing:

(1) an absorptive filler comprising at least 0.1%, by weight of the composite product, of organic carbon;

(2) at least one isocyanate selected from the group consisting of diisocyanates, polyisocyanates, and combinations thereof;

(3) one or more isocyanate-reactive monomers comprising 5% to 50% by weight of a Mannich polyol, based on the total weight of the isocyanate-reactive monomers; and

(4) an amine catalyst;

wherein the at least one isocyanate and the one or more isocyanate-reactive monomers react in the presence of the absorptive filler and the amine catalyst to form the composite product, the Mannich polyol associating with at least a portion of the organic carbon of the absorptive filler, such that a tack-free time of the composite product is less than 100 seconds.

2. The continuous process of claim 1 , wherein the tack-free time is within 10% of a tack-free time of a composite product prepared using glass beads in place of the absorptive filler.

3. The continuous process of claim 1 , wherein the composite product is formed on a belt molding system.

4. The continuous process of claim 1 , wherein the tack-free time of the composite product is within 5% of a tack-free time of a composite product prepared using glass beads in place of the absorptive filler.

5. The continuous process of claim 1 , wherein the tack-free time of the composite product is less than 90 seconds.

6. The continuous process of claim 1 , wherein the Mannich polyol is in an amount from 10% to 50% by weight, based on the total weight of the one or more isocyanate-reactive monomers of the composite product.

7. The continuous process of claim 1 , wherein the Mannich polyol comprises an alkanolamine.

8. The continuous process of claim 7 , wherein the alkanolamine comprises a dialkanolamine which includes two hydroxy-substituted C1-C12 alkyl groups, or a trialkanolamine which includes three hydroxy-substituted C1-C12 alkyl groups.

9. The continuous process of claim 1 , wherein the isocyanate-reactive monomers further comprise 10% to 40% by weight, with respect to the isocyanate-reactive monomers, of a polyol having a primary hydroxyl number greater than 250.

10. The continuous process of claim 1 , wherein the isocyanate-reactive monomers further comprise a polyester polyol, a polyether polyol, or a combination thereof.

11. The continuous process of claim 10 , wherein the isocyanate-reactive monomers further comprise an aromatic polyester polyol.

12. A method for reducing the absorption of a catalyst onto an absorptive filler during the preparation of a filled polyurethane composite, the method comprising:

preparing a mixture comprising:

(1) fly ash having at least 5.0%, by weight organic carbon, based on the total weight of the filled polyurethane composite;

(2) at least one isocyanate selected from the group consisting of diisocyanates, polyisocyanates, and combinations thereof;

(3) one or more isocyanate-reactive monomers comprising at least 30% by weight of a Mannich polyol or an alkoxylated polyamine, based on the total weight of the one or more isocyanate-reactive monomers; and

(4) an amine catalyst;

wherein the at least one isocyanate and the one or more isocyanate-reactive monomers react in the presence of the fly ash and the amine catalyst to form the filled polyurethane composite, the Mannich polyol or the alkoxylated polyamine associating with at least a portion of the organic carbon of the fly ash, such that a tack-free time of the filled polyurethane composite is less than 100 seconds.

13. The method of claim 12 , wherein a tack-free time of the filled polyurethane is less than 90 seconds.

14. The method of claim 12 , wherein the tack-free time varies less than 10% of a tack-free time of a filled polyurethane composite prepared using glass beads in place of the fly ash.

15. The method of claim 12 , wherein a cream time of the filled polyurethane composite is 5 seconds to 30 seconds.

16. A process for preparing a composite product comprising:

preparing a mixture comprising:

(1) 50% to 90% by weight of an absorptive filler, based on a total weight of the composite product, wherein the absorptive filler comprises organic carbon and has a loss on ignition value of 0.20% to 10%;

(2) at least one isocyanate selected from the group consisting of diisocyanates, polyisocyanates, and combinations thereof;

(3) one or more isocyanate-reactive monomers comprising at least 30% by weight of a Mannich polyol, based on the total weight of the one or more isocyanate-reactive monomers; and

(4) 0.05 wt % to 0.5 wt % of an amine catalyst, based on the total weight of the composite product;

introducing the mixture into a belt molding system, wherein the at least one isocyanate and the one or more isocyanate-reactive monomers react in the presence of the absorptive filler and the amine catalyst to form the composite product within the belt molding system, the Mannich polyol associating with at least a portion of the organic carbon of the absorptive filler to prevent the portion of the organic carbon from reacting with the amine catalyst;

wherein the composite product has a tack-free time within 10% of a tack-free time of a composite product prepared using glass beads in place of the absorptive filler.

17. The process of claim 16 , wherein the composite product has a tack-free time less than 100 seconds.

Assignments (7)
RELEASE OF SECURITY INTEREST IN PATENTS RECORDED AT R/F 059002/0270 Recorded Feb 12, 2025
From: UMB BANK, N.A.
To: EM RESOURCES LLC (F/K/A BORAL RESOURCES LLC)
Reel/Frame 070191/0325 →
RELEASE OF SECURITY INTEREST Recorded Jun 20, 2024
From: MUFG BANK, LTD
To: EM RESOURCES LLC (FORMERLY KNOWN AS BORAL RESOURCES LLC)
Reel/Frame 067799/0395 →
CHANGE OF NAME Recorded Mar 23, 2022
From: BORAL RESOURCES LLC
To: EM RESOURCES LLC
Reel/Frame 059482/0239 →
SECURITY INTEREST Recorded Feb 10, 2022
From: BORAL RESOURCES LLC
To: MUFG BANK, LTD.
Reel/Frame 059003/0211 →
SECURITY INTEREST Recorded Feb 10, 2022
From: BORAL RESOURCES LLC
To: UMB BANK, N.A.
Reel/Frame 059002/0270 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 11, 2022
From: BORAL INDUSTRIES INC.
To: BORAL RESOURCES LLC
Reel/Frame 058614/0959 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 11, 2022
From: BORAL IP HOLDINGS (AUSTRALIA) PTY LIMITED
To: BORAL INDUSTRIES INC.
Reel/Frame 058614/0909 →