IP Library Granted Patent US 10,683,424
Granted Patent B2
US 10,683,424 · App. 14/171,852 · Granted Jun 16, 2020

Low gloss, high solids polyurea coatings

Inventors: Shafiq Nisarali Fazel (Allentown, PA); Jared Denis Bender (Breinigsville, PA)
Assignee: Evonik Operations GmbH
C09D7/42C08G18/3814C08G18/3821C08G18/792C08K3/36C08K9/00C08K9/04C09D7/20C09D7/63C09D175/02
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Quick Facts
Patent No.
US 10,683,424
App. No.
14/171,852
Granted
Jun 16, 2020
Kind
B2
Abstract

A method of forming a low gloss, high solids polyurea coating containing very low volatile organic compounds (VOC) in the coating composition. The low volatile content not only makes the coating environmentally friendly but allows it to be applied at variable thickness levels and over a wide variety of environmental conditions. The coating composition is comprised of an isocyanate reactive agent containing a secondary diamine, a polyisocyanate, a gloss reducing agent and a viscosity modifier. The gloss reducing agent is generally pre-mixed into an isocyanate reactive agent containing a secondary diamine and/or polyisocyanate containing the viscosity modifier before mixing the two components together to form a low gloss polyurea coating.

Claims (29)

1. A one-coat film comprising an uncured non-aqueous polyurea coating composition comprising:

A) about 20 to about 70 wt % of the coating composition of an isocyanate reactive agent comprising at least one secondary diamine comprising the reaction product of bis(4-aminocyclohexyl)methane and ethyl ester of 2-butendioic acid;

B) about 10 to about 60 wt % of the coating composition of at least one polyisocyanate selected from the group consisting of hexamethylene diisocyanate biurets, hexamethylene diisocyanate trimers and hexamethylene diisocyanate dimers;

C) about 1 to about 25 wt % of the coating composition of at least one gloss reducing agent; and

D) about 2 to about 30 wt % of the coating composition of at least one viscosity modifier; wherein the gloss reducing agent comprises an organic treated precipitated silica; wherein the organic treated precipitated silica has a d50 particle size of about 3 um to about 7 um; wherein the composition comprises greater than about 70% by weight solids and less than about 1% by weight water; wherein the film is applied at one pass; wherein the film has a thickness of about 2 to about 25 mils and wherein a cured coating of the film has a 60 degree gloss value of <45.

2. The film of claim 1 , wherein the viscosity modifier comprises at least one member selected from the group consisting of hexane, heptane, xylene, toluene, cyclohexane; methyl acetate, ethyl acetate, t-butyl acetate, acetic acid ethylene glycol monomethyl ether, acetic acid diethylene glycol monomethyl ether, dibasic ester; isopropyl ether, ethylene glycol monomethyl ether, diethylene glycol monobutyl ether; methyl isobutyl ketone, methyl ethyl ketone, isophorone, acetophenone; propylene carbonate, dimethyl carbonate; n-methyl pyrollidone, n-ethyl pyrollidone; parachlorobenzotrifluoride, 1,1,2,2-Tetrachl oroethane, and 1,1-Dichloroethane.

3. The film of claim 1 , wherein the viscosity modifier comprises at least one member selected from the group consisting of bis(2-ethylhexyl) phthalate, diisononyl phthalate, butyl benzyl phthalate; dioctyl adipate, dibutyl sebacate, 1,2-Cyclohexane dicarboxylic acid diisononyl ester, 2,2,4-Trimethyl -1,3-pentanediol diisobutyrate, alkyl sulphonic acid phenyl ester; acetyl triethyl citrate, triethyl citrate; trimethyl trimellitate, tri-(2-ethylhexyl) trimellitate benzoates, sulfonamides, epoxidized vegetable oils, organophosphates, glycols, polyethers, and polybutene.

4. A one-coat film comprising an uncured non-aqueous polvurea coating composition comprising about 2 to about 30 wt % of the coating composition at least one viscosity modifier, about 10 to about 60 wt % of the coating composition of at least one polyisocyanate selected from the group consisting of hexamethylene diisocyanate biurets, hexamethylene diisocyanate trimers and hexamethylene diisocyanate dimers, about 20 to about 70 wt % of the coating composition of an isocyanate reactive agent comprising at least one secondary diamine comprising the reaction product of bis(4-amino-3-methylcyclohexyl)methane and ethyl ester of 2-butendioic acid, and about 1 to about 25 wt % of the coating composition of an organic treated precipitated silica; wherein the organic treated precipitated silica has a d50 particle size of about 3 um to about 7 um; wherein the composition comprises greater than about 70% by weight solids and less than about 1% by weight water; wherein the film is applied at one pass; wherein the film has a thickness of about 2 to about 25 mils and wherein a cured coating of the film has a 60 degree gloss value of <45.

5. The film of claim 1 , further comprising at least one member selected from the group consisting of leveling agents, defoamers, air release agents, antioxidants, UV stabilizers, rheology modifier, pigments, dispersants, plasticizers, diluents, fillers and combinations thereof.

6. The film of claim 5 , wherein the amount of said member ranges from about 1 to about 5 wt %.

7. The film of claim 1 , wherein the gloss reducing agent comprises a wax treated precipitated silica.

8. The film of claim 1 , wherein the gloss reducing agent comprises a polymer treated precipitated silica.

9. A one-coat film comprising an uncured non-aqueous polyurea coating composition comprising:

A) a reaction product of bis(4-aminocyclohexyl)methane and an ethyl ester of 2-butendioic acid;

B) a reaction product of bis(4-amino-3-methylcyclohexyl)methane and an ethyl ester of 2-butendioic acid;

C) an organic treated silica;

D) at least one solvent; and

E) at least one polyisocyanate selected from the group consisting of hexamethylene diisocyanate biurets, hexamethylene diisocyanate trimers and hexamethylene diisocyanate dimers;

wherein the composition comprises greater than about 70% by weight solids and less than about 1% by weight water; wherein the organic treated silica has a d50 particle size of about 3 um to about 7 um; wherein the film is applied at one pass; wherein the film has a thickness of about 2 to about 25 mils and wherein a cured coating of the film has a 60 degree gloss value of <45.

10. The film of claim 9 , wherein the solvent comprises at least one dibasic ester solvent.

11. The film of claim 10 , wherein the silica comprises a wax treated precipitated silica having a d50 particle size of about 3 um to about 7 um.

12. The film of claim 10 , wherein the silica comprises a polymer treated precipitated silica having a d50 particle size of about 3 um to about 7 um.

13. The film of claim 1 wherein the viscosity modifier comprises at least one member selected from the group consisting of propylene carbonate, dimethyl carbonate; n-methyl pyrollidone and butyl diglyme.

14. The film of claim 4 , wherein the viscosity modifier comprises at least one member selected from the group consisting of hexane, heptane, xylene, toluene, cyclohexane; methyl acetate, ethyl acetate, t-butyl acetate, acetic acid ethylene glycol monomethyl ether, acetic acid diethylene glycol monomethyl ether, dibasic ester; isopropyl ether, ethylene glycol monomethyl ether, diethylene glycol monobutyl ether; methyl isobutyl ketone, methyl ethyl ketone, isophorone, acetophenone; propylene carbonate, dimethyl carbonate; n-methyl pyrollidone, n-ethyl pyrollidone; parachlorobenzotrifluoride, 1,1,2,2-Tetrachl oroethane, and 1,1-Dichloroethane.

15. The film of claim 4 , wherein the viscosity modifier comprises at least one member selected from the group consisting of bis(2-ethylhexyl) phthalate, diisononyl phthalate, butyl benzyl phthalate; dioctyl adipate, dibutyl sebacate, 1,2- Cyclohexane dicarboxylic acid diisononyl ester, 2,2,4-Trimethyl-1,3-pentanediol diisobutyrate, alkyl sulphonic acid phenyl ester; acetyl triethyl citrate, triethyl citrate; trimethyl trimellitate, tri-(2-ethylhexyl) trimellitate benzoates, sulfonamides, epoxidized vegetable oils, organophosphates, glycols, polyethers, and polybutene.

16. The film of claim 4 , further comprising at least one member selected from the group consisting of leveling agents, defoamers, air release agents, antioxidants, UV stabilizers, rheology modifier, pigments, dispersants, plasticizers, diluents, fillers and combinations thereof.

17. The film of claim 16 , wherein the amount of said member ranges from about 1 to about 5 wt %.

18. The film of claim 4 , wherein the gloss reducing agent comprises a wax treated precipitated silica.

19. The film of claim 4 , wherein the gloss reducing agent comprises a polymer treated precipitated silica.

Assignments (3)
CHANGE OF NAME Recorded Nov 26, 2019
From: EVONIK DEGUSSA GMBH
To: EVONIK OPERATIONS GMBH
Reel/Frame 051135/0315 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 5, 2017
From: AIR PRODUCTS AND CHEMICALS, INC.
To: EVONIK DEGUSSA GMBH
Reel/Frame 042160/0594 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 20, 2014
From: FAZEL, SHAFIQ NISARALI; BENDER, JARED DENIS
To: AIR PRODUCTS AND CHEMICALS, INC.
Reel/Frame 032483/0452 →