IP Library Granted Patent US 10,494,473
Granted Patent B2
US 10,494,473 · App. 15/457,251 · Granted Dec 3, 2019

Hybrid novolac polyurea/polyurethane

Inventors: William E. Ishmael, Jr. (Tulsa, OK); David L. Stanley (Tulsa, OK); David J. Dunn (Aurora, OH)
Assignee: Raven Lining Systems, Inc.
C08G18/6685C08G18/0885C08G18/227C08G18/242C08G18/3203C08G18/324C08G18/3215C08G18/3225C08G18/3284C08G18/4027C08G18/4804C08G18/4841C08G18/4879C08G18/4895C08G18/542C08G18/546C08G18/6688C08G18/7664C09D175/02C09D175/04C09D175/08C08G2150/90
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Quick Facts
Patent No.
US 10,494,473
App. No.
15/457,251
Granted
Dec 3, 2019
Kind
B2
Abstract

A hybrid polyurethane/polyurea polymer suitable for forming a coating on a structure which is in contact with water includes the reaction product of a polyol component consisting of one or more polyols, a polyamine, and a curing agent, such as a polyisocyanate. The polyol component includes a Novolac-type polyether polyol.

Claims (31)

1. A hybrid polyurethane/polyurea polymer comprising the reaction product of: a polyol component, a polyamine, and a curing agent, the polyol component comprising a Novolac-type polyol having the general formula of Formula I:

where each R is independently selected from hydrocarbyl groups;

each R1 is independently selected from H and hydrocarbyl groups;

each R2 is independently selected from poly alkylene oxide groups; and

x is at least 1.

2. The hybrid polyurethane/polyurea polymer of claim 1 , wherein the reaction is carried out in the presence of a catalyst.

3. The hybrid polyurethane/polyurea polymer of claim 1 , wherein the reaction is carried out at a temperature of at least 100° C.

4. The hybrid polyurethane/polyurea polymer of claim 1 , wherein a molar ratio of the polyol component to polyamine is from 1:100 to 100:1.

5. The hybrid polyurethane/polyurea polymer of claim 1 , wherein a ratio by weight of the polyol component to polyamine is from 20:1 to 1:5.

6. The hybrid polyurethane/polyurea polymer of claim 1 , wherein the polyol component further comprises at least a second polyether polyol other than the Novolac-type polyol.

7. The hybrid polyurethane/polyurea polymer of claim 6 , wherein the second polyether polyol is selected from a glycerine and propylene oxide based polyether triol, a polyether triol, and mixtures thereof.

8. The hybrid polyurethane/polyurea polymer of claim 6 , wherein the at least a second polyether polyol includes at least one of a propylene glycol-based diol, a glycerine-initiated propylene oxide-based triol with an ethylene oxide cap, an amine-based polyol, a glycerine and sucrose-based polyol, and a Mannich-based polyol.

9. The hybrid polyurethane/polyurea polymer of claim 1 , wherein the Novolac-type polyol is derived from Cashew Nut Shell Liquid (CNSL).

10. The hybrid polyurethane/polyurea of claim 1 , wherein the Novolac-type polyol is derived from greater than 50 wt. % anacardic acid and less than 50 wt. % cardol or its methyl derivatives.

11. The hybrid polyurethane/polyurea of claim 1 , wherein the curing agent is a polyisocyanate is selected from diisocyanates and triisocyanates, and mixtures thereof.

12. The hybrid polyurethane/polyurea of claim 1 , wherein the polyamine is selected from diamines, triamines and tetramines, and mixtures thereof.

13. The hybrid polyurethane/polyurea polymer of claim 1 , wherein a ratio of moles isocyanate groups:moles of hydroxyl and amine groups is from 1.5:1 to 1:1.5.

14. A structure coated with a formulation comprising the hybrid polyurethane/polyurea polymer of claim 1 .

15. A coating formulation comprising the hybrid polyurethane/polyurea polymer of claim 1 .

16. A two component formulation for preparing a coating comprising the hybrid polyurethane/polyurea polymer of claim 1 , wherein the two component formulation includes a first component which includes the curing agent and a second component which includes the polyol component and polyamine.

17. A method for coating a structure comprising applying a two component formulation as a heated mixture to a structure, the two component formulation comprising a first component which includes a curing agent and a second component which includes a polyol component and polyamine, the polyol component comprising a polyether polyol with a phenol-based backbone, the first and second components reacting to form the hybrid polyurethane/polyurea polymer of claim 1 .

18. A hybrid polyurethane/polyurea polymer comprising the reaction product of: a polyol component, a polyamine, and a curing agent, the polyol component comprising a Novolac-type polyol having the general formula of Formula I:

wherein each R is independently selected from C8 and higher fatty acids and mixtures thereof;

each R1 is independently selected from H and hydrocarbyl groups;

each R2 is independently selected from ether groups and poly alkylene oxide groups; and

x is at least 1.

19. A method for forming a hybrid polyurethane/polyurea polymer comprising reacting a polyisocyanate, a polyol component, and a polyamine in the presence of a catalyst, the polyol component comprising a Novolac-type polyol, wherein the Novolac-type polyol has the general formula of Formula I:

where each R is independently selected from hydrocarbyl groups;

each R 1 is independently selected from H and hydrocarbyl groups;

each R 2 is independently selected from poly alkylene oxide groups; and

x is at least 1.

Assignments (9)
CORRECTIVE ASSIGNMENT TO CORRECT THE REMOVE PATENT NO. 10612196 ADD PATENT NO. 10612198 PREVIOUSLY RECORDED AT REEL: 058696 FRAME: 0261. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Feb 10, 2022
From: VERSAFLEX, INC.
To: PPG INDUSTRIES OHIO, INC.
Reel/Frame 059002/0533 →
NUNC PRO TUNC ASSIGNMENT Recorded Jan 19, 2022
From: VERSAFLEX, INC.
To: PPG INDUSTRIES OHIO, INC.
Reel/Frame 058696/0261 →
NUNC PRO TUNC ASSIGNMENT Recorded Jan 11, 2022
From: RAVEN LINING SYSTEMS INC.
To: VERSAFLEX, INC.
Reel/Frame 058617/0195 →
RELEASE OF SECURITY INTEREST Recorded Mar 2, 2021
From: BMO HARRIS BANK N.A.
To: VERSAFLEX, INC.; RAVEN LINING SYSTEMS INC.; VF SPECIALTY PRODUCTS; MILAMAR COATINGS, L.L.C.
Reel/Frame 055455/0901 →
RELEASE OF SECURITY INTEREST Recorded Apr 25, 2019
From: TEXAS CAPITAL BANK (A NATIONAL BANKING INSTITUTION)
To: RAVEN LINING SYSTEMS, INC. (AN OKLAHOMA CORPORATION)
Reel/Frame 048993/0080 →
PATENT SECURITY AGREEMENT Recorded Apr 24, 2019
From: VERSAFLEX INC.; RAVEN LINING SYSTEM INC.; VF SPECIALTY PRODUCTS, LLC; MILAMAR COATINGS L.L.C.
To: BMO HARRIS BANK N.A. , AS ADMINISTRATIVE AGENT
Reel/Frame 048991/0375 →
SECURITY INTEREST Recorded Sep 17, 2018
From: RAVEN LINING SYSTEMS, INC. (AN OKLAHOMA CORPORATION)
To: TEXAS CAPITAL BANK (NATIONAL BANKING ASSOCIATION)
Reel/Frame 046889/0701 →
SECURITY INTEREST Recorded Jan 3, 2018
From: RAVEN LINING SYSTEMS, INC. (AN OKLAHOMA CORPORATION)
To: TEXAS CAPITAL BANK (A NATIONAL BANKING INSTITUTION)
Reel/Frame 044525/0625 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 13, 2017
From: ISHMAEL, WILLIAM E., JR; STANLEY, DAVID L.; DUNN, DAVID J.
To: RAVEN LINING SYSTEMS INC.
Reel/Frame 041559/0349 →
Continuity (2)
Provisional Application 62307899 · Mar 14, 2016
Related Publication 20170260319A1 · Sep 14, 2017