Emulsifiable isocyanate compositions

Details Emulsifiable isocyanate compositions Emulsifiable isocyanate compositions

2001-01-22

2002-06-18

Gorr, Rachel (Department: 1711)

Synthetic resins or natural rubbers -- part of the class 520 ser

Synthetic resins

From reactant having at least one -n=c=x group as well as...

C252S182220, C254S391000, C254S391000, C528S045000, C528S074500, C560S026000, C516S053000, C516S203000, C525S123000, C525S454000

Reexamination Certificate

active

06407196

ABSTRACT:

TECHNICAL FIELD
This invention relates to polyisocyanate derived adducts, to emulsifiable polyisocyanates which employ those adducts, and to emulsions which include the emulsifiable polyisocyanates.
BACKGROUND ART
The use of water based coatings is important due to environmental considerations. In the case of isocyanate-reactive coatings, however, water presents a problem in that the isocyanate groups react with water. In order to overcome this disadvantage, the prior art has used emulsifiable adducts which are the reaction products of polyisocyanates and hydroxy functional polyethers. These adducts have latent isocyanate functionality to assist in crosslinking of the water based coating and sufficient hydrophilic character to keep the water based coating composition dispersed in an aqueous medium. These adducts, however, tend to react with water to form urea reaction products which reduce the working life of the emulsifiable polyisocyanate. Moreover, exposure of these emulsifiable polyisocyanates to heat can form undesirable polyureas which greatly reduces the pot life of the emulsifiable polyisocyanate.
A need exists for more stable water emulsifiable polyisocyanates which are less likely to react with water to extend the working life of the emulsifiable polyisocyanates in water.
DISCLOSURE OF INVENTION
In a first aspect, the invention relates to polyisocyanate derived adducts. The adducts are the reaction products of a urethane prepolymer and a capping agent. The capping agent is any of methoxypolyoxyethylene monols, polyoxyethylene-polyoxypropylene monols, and mixtures thereof. The urethane prepolymer is the reaction product of a dihydroxy functional polyol and an isocyanate. The dihydroxy functional polyol is any of polyoxyethylene glycol and polyoxyethylene polyoxypropylene glycols. Preferably, the methoxypolyoxyethylene monols have a molecular weight of about 350 to about 750, and the polyoxyethylene-polyoxypropylene monols have a molecular weight of about 270 to about 3930. Preferably, the urethane prepolymer and the capping agent are present in a weight ratio of urethane prepolymer to capping agent of about 2:1 to about 1:2, the dihydroxy functional polyol and the isocyanate are present in a weight ratio of dihydroxy functional polyol to isocyanate of about 2:1 to about 25:1, and the capping agent and the urethane prepolymer are present in a weight ratio of the capping agent to the prepolymer of about 1:1 to about 1:3.
In another aspect, the invention relates to an emulsifiable polyisocyanate that includes an isocyanate and a polyisocyanate derived adduct.
In yet another aspect, the invention relates to an aqueous emulsion having greatly improved stability. The aqueous emulsion includes emulsifiable polyisocyanate. The emulsifiable polyisocyanate includes an isocyanate and a polyisocyanate derived adduct. The polyisocyanate derived adduct includes the reaction product of a urethane prepolymer and a capping agent. The capping agent may be any of methoxypolyoxyethylene monols, polyoxyethylene-polyoxypropylene monols, and mixtures thereof. The urethane prepolymer is the reaction product of a dihydroxy functional polyol and an isocyanate. The urethane prepolymer and the capping agent can be present in a weight ratio of urethane prepolymer to capping agent of about 2:1 to about 1:2, the dihydroxy functional polyol and the isocyanate can be present in a weight ratio of dihydroxy functional polyol to isocyanate of about 2:1 to about 25:1, and the capping agent and urethane prepolymer are present in a weight ratio of the capping agent to the prepolymer of about 1:1 to about 1:3.
In yet another aspect, the invention relates to an aqueous latex emulsion having greatly increased stability. The aqueous latex emulsion includes an emulsifiable isocyanate. The emulsifiable polyisocyanate may be any of a first reaction product of polymeric methane diphenyl diisocyante, methoxypolyoxyethylene monol, and a polyisocyanate derived adduct, the adduct comprising the reaction product of a urethane prepolymer and a methoxypolyoxyethylene monol, wherein the urethane prepolymer is the reaction product of a dihydroxy functional polyol and an isocyanate, a second reaction product of product of uretomine modified 4,4′-diphenylmethane diisocyanate having about 26% NCO, and a mixture of methoxypolyoxyethylene monol and a polyisocyanate derived adduct comprising the reaction product of a urethane prepolymer and a methoxypolyoxyethylene monol, wherein the urethane prepolymer is the reaction product of a dihydroxy functional polyol and an isocyanate, and a third reaction product of uretonimine modified 4,4′-diphenylmethane diisocyanate having a NCO value of about 29.3%, and a mixture of methoxypolyoxyethylene monol and a polyisocyanate derived adduct comprising the reaction product of a urethane prepolymer and a methoxypolyoxyethylene monol, wherein the urethane prepolymer is the reaction product of a dihydroxy functional polyol and an isocyanate.
Having summarized the invention, the invention is described in detail below by reference to the detailed description below and the following non-limiting examples.
MODES FOR CARRRYING OUT THE INVENTION
Glossary of Terms and Definitions:
1. Arcol PPG-725 is a polyoxypropylene glycol of the formula HO—(CH
2
CH
3
CHO)
n
—H from Lyondell Chemical Company and has a molecular weight of 725.
2. Carbowax MPEG 350 is a methoxypolyoxyethylene monol of the formula CH
3
—(OCH
2
CH
2
)
n
—OH where n has an average number of 7. Carbowax 350 is available from Union Carbide Chemicals and Plastics and has a molecular weight of 350.
3. Carbowax 550 is a methoxypolyoxyethylene monol of the formula CH
3
—(OCH
2
CH
2
)
n
—
0
H where n has an average number of 12. Carbowax 550 is available from Union Carbide Chemicals and Plastics and has a molecular weight of 550.
4. Carbowax 750 is a methoxypolyoxyethylene monol of the formula CH
3
—(OCH
2
CH
2
)
n
—OH where n has an average number of 16. Carbowax 750 is available from Union Carbide Chemicals and Plastics and has a molecular weight of 750.
5. Carbowax 600 is a polyoxyethylene glycol of the formula H—(OCH
2
CH
2
)
n
—OH where n is an average number of 13. Carbowax 600 is available from Union Carbide Chemicals and plastics and has a molecular weight of 600.
6. Castor oil is a trifunctional, low molecular weight fatty ester polyol that has a hydroxyl No. 164.
7. Ucon 50-HB-55 is an alcohol started polyoxyethylene polyoxypropylene monol of the formula RO—(CH
2
CH
3
CHO)
n
—(CH
2
CH
2
O)
n
—H and has equal amounts by weight of oxyethylene and oxypropylene groups. Ucon 50-HB-55 is available from Union Carbide Chemicals and plastics and has a molecular weight of 270.
8. Ucon 50-HB-100 is an alcohol started polyoxyethylene polyoxypropylene monol of the formula RO—(CH
2
CH
3
CHO)
n
—(CH
2
CH
2
O)
n
—H and has equal amounts by weight of oxyethylene and oxypropylene groups. Ucon 50-HB-100 is available from Union Carbide Chemicals and plastics and has a molecular weight of 520.
9. Ucon 50-HB-170 is an alcohol started polyoxyethylene polyoxypropylene monol of the formula RO—(CH
2
CH
3
CHO)
n
—(CH
2
CH
2
O)
n
—H and has equal amounts by weight of oxyethylene and oxypropylene groups. Ucon 50-HB-100 is available from Union Carbide Chemicals and plastics and has a molecular weight of 750.
10. Ucon 50-HB-260 is an alcohol started polyoxyethylene polyoxypropylene monol of the formula RO—(CH
2
CH
3
CHO)
n
—(CH
2
CH
2
O)
n
—H and has equal amounts by weight of oxyethylene and oxypropylene groups. Ucon 50-HB-260 is available from Union Carbide Chemicals and plastics and has a molecular weight of 970.
11. Ucon 50-HB-400 is an alcohol started polyoxyethylene polyoxypropylene monol of the formula RO—(CH
2
CH
3
CHO)
n
—(CH
2
CH
2
O)
n
—H and has equal amounts by weight of oxyethylene and oxypropylene groups. Ucon 50-HB-400 is available from Union Carbide Chemicals and plastics and has a molecular weight of 1230.
12. Ucon 50-HB-660 is an alcohol started polyoxyethylene polyoxypropylene monol of the formula RO—(CH
2
CH
3
CHO)
n
—(CH
2
CH
2
O)

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