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Low-temperature curing coating compositions

a technology of coating compositions and curing temperatures, applied in the direction of coatings, adhesive types, electricly conductive paints, etc., can solve the problems of tin and lead catalysts being tin and lead catalysts have been subject to a number of regulatory restrictions, and previous blocked polyisocyanates that unblock at relatively low temperatures have been difficult to make,

Pending Publication Date: 2019-11-28
PPG IND OHIO INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This patent is about a coating composition that includes a special polymer, a blocked polyisocyanate curing agent, and a curing catalyst. The coating composition does not contain any harmful substances like tin, lead, iron, zinc, or manganese. The technical effect of this composition is that it can be applied to a substrate to create a durable and high-quality coating that is safe and effective. The coating can be used for a variety of purposes such as protective or decorative coatings.

Problems solved by technology

Heating requires significant energy costs.
Previous blocked polyisocyanates that unblock at relatively low temperatures have been difficult to make, are toxic, or are crystalline and difficult to handle.
Additionally, while catalyst may be used to reduce the curing temperature of the coating composition, tin and lead catalysts have been subjected to a number of regulatory restrictions by various countries due to environmental concerns.

Method used

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  • Low-temperature curing coating compositions
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Examples

Experimental program
Comparison scheme
Effect test

example 1

Preparation of Dibutylglycolamide (“DBGA”) Blocked Polyisocyanate Curing Agent (Ratio of Isocyanato Groups from Toluene Diisocyanate to Blocking Groups from Trimethylol Propane and DBGA: TDI / TMP / DBGA=10 / 5 / 5)

[0146]

Amount#MateriallbsKg1Toluene diisocyanate7568.803433.152Methyl isobutyl ketone4249.601927.583Dibutyltin dilaurate1773.60 gm1773.60 gm4Trimethylol propane2000.00907.185Methyl isobutyl ketone1000.00453.596Dibutyl glycolamide18816.003998.877Methyl isobutyl ketone1000.00453.598Bisphenol A polyol2137.50969.559DOWANOL PPH22850.001292.7410Methyl isobutyl ketone2205.001000.171Prepared according to Example 1 of U.S. Pat. No. 4,452,9302Available from DOW Chemicals

[0147]A dibutylglycolamide blocked polyisocyanate curing agent was prepared as follows: Charges 1, 2 and 3 were combined in a flask set up for total reflux with stirring under nitrogen and heated to 35° C. Charge 4 was then added in four equal portions with a 30-minute hold following each addition. Following addition of char...

example 2

Preparation of a Cationic Amine-Functionalized Resinous Dispersion using the DBGA Blocked Polyisocyanate Curing Agent of Example 1

[0148]

Amount#MateriallbsKg1EPON 82819660.004381.702Bisphenol A4237.001921.873Methyl isobutyl ketone (“MIBK”)1161.00526.624Ethyl triphenyl phosphonium bromide9.704.405Dowanol PPh21435.00650.906Methyl isobutyl diketimine of diethylene1015.00460.40triamine (72.7% solids in MIBK)37Methyl ethanol amine866.00392.818DBGA Blocked Crosslinker418060.008191.87990% Formic acid606.00274.8810DI Water13184.005980.1611DI Water32090.0014555.771Difunctional bisphenol A / epichlorohydrin derived liquid epoxy resin2 Available from DOW chemical company3Reaction product of diethylene triamine and methyl isobutyl ketone produced by combining diethyelen triamine and excess methyl isobutyl ketone in a reactor equipped with a mechanical stirrer, temperature probe, and a condenser with a Dean Stark trap filled with methyl isobutyl keton attached and heating the mixture to reflux. Wat...

example 3

Synthesis of N-Butyl Glycolamide Blocking Agent

[0150]An N-butyl glycolamide blocking agent was prepared according to the following procedure: 1,000.43 g of glycolide (commercially available from AK Scientific, Inc.) was charged into a 3000-mL, 4-necked round bottom flask equipped with a stirrer, a condenser, a nitrogen inlet, and a thermocouple. Agitation and a nitrogen flow of 0.2 standard cubic feet (scft) / minute were started. 1,266.59 g of Mono-N-butylamine (commercially available from Eastman Chemical Company) was added to the flask over 4.5 hours at a rate such that the reactor temperature did not exceed 65° C. An ice bath was also placed under the flask during the addition to control the reaction temperature. After completion of the addition, the reaction mixture was heated to 80° C. and held for 4 hours until the MEQ amine is less than 0.2 as measured by titration using a Metrohm 751 PGPD Titrino with 0.1 N Perchloric acid in glacial acetic acid as the titration reagent. A sl...

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Abstract

The present invention is directed towards a coating composition comprising a film-forming polymer comprising active hydrogen-containing functional groups; a blocked polyisocyanate curing agent comprising a blocking group derived from a blocking agent comprising an alpha-hydroxy amide, ester or thioester; and a curing catalyst that does not contain tin, lead, iron, zinc or manganese. Also disclosed are coatings, coated substrates, and methods of coating a substrate.

Description

CROSS-REFERENCE TO RELATED APPLICATIONS[0001]This application claims the benefit of U.S. Provisional Patent Application Ser. No. 62 / 455,778, filed on Feb. 7, 2017, incorporated herein by reference.FIELD OF THE INVENTION[0002]The present invention relates to coating compositions, methods for making such coating compositions, methods of coating substrates, coatings and coated substrates.BACKGROUND INFORMATION[0003]Blocked polyisocyanate curing agents are utilized in a wide variety of coating systems. Upon the application of external energy, such as heating, the blocking agent used to “block” the isocyanato groups is removed allowing the isocyanato groups to react with a polymeric binder resin and cure the coating. Heating is often employed to remove blocking agents from a blocked polyisocyanate curing agent. Heating requires significant energy costs. Previous blocked polyisocyanates that unblock at relatively low temperatures have been difficult to make, are toxic, or are crystalline ...

Claims

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Application Information

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IPC IPC(8): C09J175/00C08G18/20C08G18/22C08G18/58C08G18/76C08G18/80C08G18/28C08G18/32C09D5/24
CPCC08G18/8029C08G18/58C08G18/8074C08G18/2855C09D5/24C08G18/3271C08G18/3215C08G18/7621C08G18/227C08G18/2072C08G18/3256C08G18/3206C08G18/7671C09J175/00C09D201/02C08G18/32C08G18/50C08G18/76C08G18/80C09D5/44C09D175/00C08G18/0814C08G18/10C08G18/12C08G18/643C08G18/78C08G18/8061C08G18/807C09J175/06C08L2207/53C09J11/08C09J163/00
Inventor ESWARAKRISHNAN, VENKATACHALAMZHOU, HONGYINGSANDALA, MICHAEL G.NOVAK, CAROLYN A.K.BICE, JO-ANN E.DACKO, CHRISTOPHER A.RO, HYUN WOOKSYPUT, RICHARD F.PUODZIUKYNAITE, EGLEWILSON, CRAIG A.JONES, JUSTIN M.TILLMAN, HERBERT
Owner PPG IND OHIO INC