Monomers and polymers and latices therefrom

Details Monomers and polymers and latices therefrom Monomers and polymers and latices therefrom

2000-05-26

2001-10-09

Yoon, Tae H. (Department: 1714)

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

Synthetic resins

At least one aryl ring which is part of a fused or bridged...

C524S516000, C524S809000, C526S259000, C526S288000

Reexamination Certificate

active

06300410

ABSTRACT:

FIELD OF THE INVENTION
This invention relates to novel monomers useful for promoting the wet adhesion of latex coatings, to latices and paints prepared therewith and to related methods.
BACKGROUND OF THE INVENTION
The use of water-based emulsion polymer systems as protective and decorative coatings for many types of surfaces has become widespread. The so-called latex paint is commonly used by individuals in homes and industrially. While oil-based systems are known to retain their adhesive properties under wet or humid conditions, a characteristic called “wet adhesion”, the tendency of many water-based coating to lose their adhesive properties when wet has limited the usefulness of such coatings. This is particularly true for paints based on vinyl-acrylic or all acrylic latices which otherwise are attractive as paint vehicles.
Paints intended for outdoor use are frequently exposed to moisture and humidity, as are paints used on interior surfaces in wet or humid atmospheres, such as in bathrooms and kitchens. Good wet adhesion is an important attribute of paints applied to those surfaces and others where resistance to water and abrasion is important, as where paints are exposed to washing or scrubbing, and where water-based paints are applied to glossy surfaces. In these situations, the need for improved wet adhesion of aqueous emulsion polymer systems is particularly great.
The art has recognized the problem of loss of adhesive properties in latex paints when wet, and a variety of additives to latex systems to improve wet adhesion has been proposed. For example, U.S. Pat. No. 3,356,655, issued on Dec. 5, 1967, and U. S. Pat. No. 3,509,085, issued on Apr. 28, 1970, disclose a number of ethylenically unsaturated hydroxy-functional amines which are said to be useful in improving adhesion and water resistance of latex paints. In addition, U. S. Pat. No. 4,111,877, issued on Sep. 5, 1978, discloses certain imidazolidinone derivatives which are said to improve the adhesive properties of latex paint.
It has now been found that latex-containing surface coatings and coating compositions having excellent wet adhesion properties can be produced by including in the monomer system one or a mixture of novel polymerizable monomers. In particular, the new compounds of this invention have been found to be especially useful in water-based latex-containing paints and can also be employed as comonomers in solution polymers. U.S. Pat. Nos. 4,487,940 and 4,526,915 (Sekmakas et al.) disclose an acrylate or methacrylate functional copolymerizable monomer which serves to improve the adhesion of emulsion polymers is disclosed. This monomer is the adduct formed by reacting an aminoalkyl alkylene urea with about 0.9 up to about 1.5 molar proportions of a saturated monoepoxide to consume most or all of one of the two amino hydrogen atoms available, and then reacting with about 0.8 up to about 2.0 molar proportions of a monoisocyanate having a single acrylate or methacrylate group in the presence of at least 0.02%, based on the total weight of the reactants present, of an inhibitor, such as hydroquinone or phenothiazine, which retards the free-radical polymerization of ethylenic unsaturation.
SUMMARY OF THE INVENTION
This invention relates to a composition of matter consisting essentially of a monomer having the formula:
wherein:
R
1
is alkylene having about 2 or 3 carbon atoms, preferably 2 carbon atoms;
R
2
is alkylene having about 2 to about 10 carbon atoms, preferably 2 or 3 carbon atoms;
X is oxygen, sulfur, or NR
3
wherein R
3
is hydrogen, alkyl, substituted alkyl, alicyclic, substituted alicyclic, aryl, substituted aryl, heteroalkyl, heterocyclic, preferably X is NH;
R
4
has the structure of the residue of an alicylic diisocyanate wherein the isocyanate groups have reactivites that differ one from another, preferably R
4
has the structure of the residue of an alicylic diisocyanate wherein one or more alkyl groups pendant to an alicylic ring provide greater steric hindrance to one isocyanate group than the other isocyanate group, e.g. wherein R
4
has the structure of the residue of isophorone diisocyanate;
Y is oxygen, sulfur, or NR
5
wherein R
5
is hydrogen, alkyl, substituted alkyl, alicyclic, substituted alicyclic, aryl-, substituted aryl, heteroalkyl, or heterocyclic, Y is preferably oxygen;
R
6
is alkylene, arylene, aralkylene, alkarylene, or heteroalkylene, preferably ethylene;
Z is oxygen, sulfur, or NR
7
wherein R
7
is hydrogen, alkyl, substituted alkyl, alicyclic, substituted alicyclic, aryl, substituted aryl, heteroalkyl, or heterocyclic, Z is preferably oxygen; and
R
8
is hydrogen or methyl, preferably methyl.
This invention also relates to a method of making a monomer composition as described above wherein a diisocyanate of formula OCN—R
4
—NCO is reacted with an ethylenically unsaturated compound of formula HY—R
6
—Z—C(O)—CR
8
═CH
2
and the product thereof is reacted with a compound of formula (II):
This invention also relates to polymers and latices prepared from the monomers of this invention and to methods of making latices comprising blending latices, and the use of latices in making water-based paints with good wet adhesion.
DETAILED DESCRIPTION OF THE INVENTION
As noted above, the monomers of this invention can be prepared by reacting a diisocyanate of formula OCN—R
4
—NCO with an ethylenically unsaturated compound of formula HY—R
6
—Z—C(O)—CR
8
═CH
2
and then reacting the product thereof with a compound of formula II. The conditions of the reaction should be such that the product is essentially monoethylenically unsaturated. This will ensure that the monomer composition will not contain di-ethylenic unsaturation which can cause crosslinking in a polymer subsequently prepared from the monomer composition. The monomers can also be prepared by first reacting the diisocyanate with the compound of formula II and then reacting the product with the ethylenically unsaturated compound. The reaction conditions should likewise be such that the only one of the isocyanate groups reacts with a compound of formula II. This will ensure that the product will consist essentially of mono-ethylenically unsaturated polymerizable materials. Thus, the use of the term “consisting essentially” is intended to exclude compositions which contain significant amounts of di-ethylenic compounds and non-polymerizable compounds.
Examples of the compounds of formula II include the compound N-aminoethylethyleneurea (hereinafter “AEEU”). AEEU is commercially available and can be made as described in U.S. Pat. No. 2,613,212, the disclosure of which is incorporated herein by reference. The other variants of compound II can be made by varying the reactants used in the reaction of U.S. Pat. No. 2,613,212 or by derivatizing the products thereof.
Examples of the ethylenically unsaturated compounds include hydroxyethyl methacrylate, hydroxyethyl acrylate, hydroxypropyl methacrylate, and hydroxypropyl acrylate. These compounds are commercially available and can be made by methacrylating or acrylating the respective ethylene or propylene glycol. The sulfur and amino analogues can be made similarly.
Examples of alicylic diisocyanate compounds include isophorone diisocyanate which is commercially available and which can be prepared by the phosgenation of isophorone diamine. Other alicyclic diisocyanates can be prepared by the phosgenation of the corresponding diamine. It is important that such other alicyclic diisocyanates also show, under the chosen reaction conditions, a sufficient difference in reactivity between the two isocyanate groups to result in an intermediate that is essentially a monourethane, or the sulfur or amino analogue thereof.
A means of providing a difference in reactivity of the isocyanate groups is steric hindrance of one group that is greater than the steric hindrance of the other group, e.g. by alkyl groups pendant to the alicylic ring. For example, it is believed that in isophorone diisocyanate, wherein one isocyanate group is pendent to an alicylic ring carbon of said residue

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