Polyurethane dispersion, method of producing the same, coated articles, and method for coating articles

Patent metadata

Field	Value
Publication number	US-9512262-B2
Application number	US-201013262572-A
Country	US
Kind code	B2
Filing date	Feb 8, 2010
Priority date	Mar 31, 2009
Publication date	Dec 6, 2016
Grant date	Dec 6, 2016

Abstract

The instant invention is a polyurethane dispersion, method of producing the same, coated articles, and method for coating articles. The polyurethane dispersion according to the present inventions includes (a) one or more polyurethane units derived from one or more prepolymers wherein the one or more prepolymers comprise the reaction product of a mixture dissolved in dipropylene glycol dimethyl ether in the presence of one or more first surfactants with one or more isocyanates, wherein the mixture comprises one or more natural oil based polyols, and one or more adipate polyols, and optionally one or more short diols; and (b) water.

First claim

We claim:

1. A polyurethane dispersion comprising:
one or more polyurethanes derived from one or more prepolymers wherein said one or more prepolymers comprise the reaction product of a mixture dissolved in dipropylene glycol dimethyl ether in the presence of one or more first surfactants with one or more isocyanates, wherein said mixture comprises one or more natural oil based polyols, and one or more adipate polyols, and optionally one or more short chain diols, wherein short chain diols are diols which have a molecular weight from 50 to 500 g/mole, the one or more natural oil based polyols are obtained by hydroformylating fatty acid methyl esters derived from one or more natural oils to aldehyde intermediates, hydrogenating the aldehyde intermediates to monomers having an average hydroxyl functionality of above 1.5 and not higher than 6, and transesterifying the monomers with a glycol initiator, thereby obtaining the one or more natural oil based polyols by a combination of condensation of a portion of the monomers with the glycol initiator and self-condensation of another portion of the monomers, the natural oil based polyols containing primary hydroxyl groups and no unsaturation; and
water
wherein a film derived from the polyurethane dispersion as a coating on a metal substrate has a Konig Hardness in the range of greater than 125 seconds to equal to and less than 159 seconds according to ASTM D-4366, and a rating of Water Resistance in the range of 0 on a scale of 0 to 5, wherein 0 is no swelling or blemish and wherein 5 is disintegrated, according to the ASTM D-870.

2. A process for producing a polyurethane dispersion comprising the steps of:
providing a first stream comprising one or more prepolymers, wherein said one or more prepolymers comprise the reaction product of a mixture dissolved in dipropylene glycol dimethyl ether in the presence of one or more first surfactants with one or more isocyanates, wherein said mixture comprises one or more natural oil based polyols, and one or more adipate polyols, and optionally one or more short chain diols, wherein short chain diols are diols which have a molecular weight from 50 to 500 g/mole, and wherein said one or more prepolymers are optionally neutralized with one or more neutralizing agents, the one or more natural oil based polyols are obtained by hydroformylating fatty acid methyl esters derived from one or more natural oils to aldehyde intermediates, hydrogenating the aldehyde intermediates to monomers having an average hydroxyl functionality of above 1.5 and not higher than 6, and transesterifying the monomers with a glycol initiator, thereby obtaining the one or more natural oil based polyols by a combination of condensation of a portion of the monomers with the glycol initiator and self-condensation of another portion of the monomers, the natural oil based polyols containing primary hydroxyl groups and no unsaturation;
providing a second stream comprising water;
merging said first stream and said second stream together;
thereby forming prepolymer dispersion;
optionally neutralizing said prepolymer dispersion;
chain extending said prepolymers;
thereby forming said polyurethane dispersion
wherein a film derived from the polyurethane dispersion as a coating on a metal substrate has a Konig Hardness in the range of greater than 125 seconds to equal to and less than 159 seconds according to ASTM D-4366, and a rating of Water Resistance in the range of 0 on a scale of 0 to 5, wherein 0 is no swelling or blemish and wherein 5 is disintegrated, according to the ASTM D-870.

3. A coated article comprising:
a substrate;
a coating associated with one or more surfaces of said substrate, wherein said coating is derived from a polyurethane dispersion comprising;
one or more polyurethanes derived from one or more prepolymers, wherein said one or more prepolymers comprise the reaction product of a mixture dissolved in dipropylene glycol dimethyl ether in the presence of one or more first surfactants with one or more isocyanates, wherein said mixture comprises one or more natural oil based polyols, and one or more adipate polyols, and optionally one or more short chain diols, wherein short chain diols are diols which have a molecular weight from 50 to 500 g/mole, the one or more natural oil based polyols are obtained by hydroformylating fatty acid methyl esters derived from one or more natural oils to aldehyde intermediates, hydrogenating the aldehyde intermediates to monomers having an average hydroxyl functionality of above 1.5 and not higher than 6, and transesterifying the monomers with a glycol initiator, thereby obtaining the one or more natural oil based polyols by a combination of condensation of a portion of the monomers with the glycol initiator and self-condensation of another portion of the monomers, the natural oil based polyols containing primary hydroxyl groups and no unsaturation; and
water

wherein a film derived from the polyurethane dispersion as a coating on a metal substrate has a Konig Hardness in the range of greater than 125 seconds to equal to and less than 159 seconds according to ASTM D-4366, and a rating of Water Resistance in the range of 0 on a scale of 0 to 5, wherein 0 is no swelling or blemish and wherein 5 is disintegrated, according to the ASTM D-870.

Assignees

• Erdem Bedri
• Nanjundiah Kumar
• Argyropoulos John N
• Kaufman Michael C
• Guo Jihui
• Foley Paul
• Bhattacharjee Debkumar
• Dow Global Technologies Llc

Inventors

• Erdem Bedri
• Nanjundiah Kumar
• Argyropoulos John N
• Kaufman Michael C
• Guo Jihui
• Foley Paul
• Bhattacharjee Debkumar

Classifications

• C08G18/0823

  containing carboxylate salt groups or groups forming them · CPC title

• C08G18/36

  Hydroxylated esters of higher fatty acids · CPC title

• B32B27/40

  comprising polyurethanes · CPC title

• C08G18/0819

  containing anionic or anionogenic groups · CPC title

• C08J7/04

  Coating · CPC title