Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – From heterocyclic reactant containing as ring atoms oxygen,...
Reexamination Certificate
2001-02-15
2002-10-15
Truong, Duc (Department: 1711)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
From heterocyclic reactant containing as ring atoms oxygen,...
C528S483000, C524S366000, C524S376000, C524S377000, C568S618000, C568S619000, C568S622000, C568S623000, C568S624000, C568S625000
Reexamination Certificate
active
06465605
ABSTRACT:
FIELD OF THE INVENTION
This invention relates to polymeric compounds useful as low foaming surfactants and as defoaming and stabilizing agents for both aqueous-based and nonaqueous-based compositions, especially hydrophilic emulsion polymer latexes.
BACKGROUND OF THE INVENTION
There is an increasing need for surfactants that are low foaming for use in compositions where high levels of foam are disadvantageous. In addition, some low foaming surfactants have limited mobility properties which can limit their use where high mobility is desired or required.
Also, defoaming agents for aqueous-based systems are often required to reduce the foam generated by high foaming surfactants and other components of such aqueous-based systems. Such aqueous-based systems include latex paints, printing inks, protective coatings for paper and metal, and the like.
However, some defoaming agents and compositions containing them exhibit limited hydrolytic stability. Moreover, for some applications it is desirable to use defoaming agents having both hydrophilic and hydrophobic properties. Moreover, in the preparation and use of water-based coatings, a recurrent problem is the presence of very small air bubbles (microform) which are not broken by defoamers which are currently used as a component of these coatings.
SUMMARY OF THE INVENTION
The present invention relates to low foaming surfactants which are water-soluble or water-dispersible, and possess good hydrolytic stability and high mobility. They are useful as both defoaming and stabilizing agents for aqueous-based compositions. The invention also relates to aqueous or organic solvent dispersions or solutions containing the surfactants, to methods for the preparation of the surfactants, and to aqueous-based compositions containing these surfactants. The present low foaming surfactants are also useful as microfoam control agents in water-based coating compositions, wherein microfoam problems are eliminated or at least significantly reduced.
The surfactants of the invention include branched compounds or mixtures of compounds which are the base-catalyzed, reaction products of components comprising
A) at least one linking compound of formula I
R
1
(X)
3
(I)
wherein each X group is a halogen atom or one X group is a halogen atom and two X groups represent an epoxy oxygen atom, which is attached to two adjacent carbon atoms in the R
1
group to form an epoxy group, and R
1
is an alkanetriyl group containing from 3 to 10 carbon atoms;
B) at least one compound of formula II
R
2
(OA)
n
X (II)
wherein R
2
is an organic group containing from 1 to 36 carbon atoms, n is a number of from 0 to 200, preferably 1 to 100, more preferably 2 to 20, X is —OH, —NHR′ wherein R′ is hydrogen or a C
1-C
4
alkyl group, or —SH, and each OA group is independently an ethyleneoxy, 1,2-propyleneoxy, or 1,2-butyleneoxy group, provided that when X is an amine group, n is at least 1; and, optionally,
C) from about 0.001 to about 50 mole %, preferably from 10 to 30 mole %, based on the total moles of components A), B) and C), of at least one of the following compounds,
a) a polyol containing at least 3 hydroxyl groups, one or more of which are optionally alkoxylated, and
b) a polyamine containing at least two amino groups, e.g. 2, 3, 4, 5 or 6 amino groups or more, and which can optionally contain alkyleneoxy groups, e.g., a polyether backbone based on ethylene oxide (EO), propylene oxide (PO), or both ethylene oxide and propylene oxide (EO/PO); wherein the ratio of moles of component A) to the sum of the —OH, —SH, and —NHR′ equivalents in components B) plus C) is from about 0.6:1 to about 5.0:1; more preferably from 0.8:1 to 1.4:1; provided that when component C) is not present, component B) is a mixture of at least two compounds of formula II wherein the R
2
group in the first compound (B) a)) is an aliphatic group, preferably an alkyl group, containing from 1 to 8 carbon atoms, or a phenol or styrenated phenol group, and the R
2
group in the second compound (B) b)) is an aliphatic group, preferably an alkyl group, containing from 9 to 36 carbon atoms, and said second compound B) b) is present in from about 0.001 to about 50 mole %, preferably from 10 to 30 mole %, based on the moles of the first compound B) a), and when component C) is present R in component B) contains from 4 to 36 carbon atoms.
DESCRIPTION OF THE PREFERRED EMBODIMENTS
Other than in the operating examples, or where otherwise indicated, all numbers expressing quantities of ingredients or reaction conditions used herein are to be understood as modified in all instances by the term “about”.
In the above reaction products, the compounds of formula II in component B) are aliphatic (optionally alkoxylated) alcohols or phenol or styrenated phenol which are also optionally alkoxylated, and/or the corresponding sulfhydryl and amine compounds.
The R
2
group can be a substituted or unsubstituted, saturated or unsaturated hydrocarbon group having from 1 to 36 carbon atoms. Examples of such hydrocarbon groups include linear or branched alkyl groups having from 1 to 22 carbon atoms, preferably from 4 to 22 carbon atoms, linear or branched alkenyl and alkynyl groups having from 2 to 22 carbon atoms, preferably from 4 to 22 carbon atoms, aryl groups having from 6 to 22 carbon atoms, and arenyl groups having from 7 to 22 carbon atoms.
The R group can also be a saturated carbocyclic group, an unsaturated carbocyclic group having one or more multiple bonds, a saturated heterocyclic group, or an unsaturated heterocyclic group having one or more multiple bonds. Any of the above R
2
groups can be substituted groups, i.e. the groups can contain single or multiple substitutions such as a halogen substitution, for example Cl, Fl, I and Br; a sulfur functionality such as mercaptan or thio group; a nitrogen functionality such as an amine or amide functionality; a silicon functionality, e.g. a siloxane group; or any combination thereof.
When component C) is present, the R
2
group in formula II is preferably a straight or branched chain alkyl group containing from 4 to 36 carbon atoms, preferably from 8 to 12 carbon atoms.
When X in formula II is an amine or sulfhydryl group, the resulting compounds can be readily prepared from the corresponding alcohols wherein the terminal hydroxy group is replaced by an —SH group or by an amine nitrogen. For example, a compound of formula II where X is —OH can be subjected to a catalyzed ammoniation (with ammonia, or a lower alkylamine) for replacement of the hydroxyl, or to a capping of the hydroxyl with epichlorohydrin followed by ammoniation (with ammonia, or a lower alkylamine) of the resulting glycidal group. Many of these compounds are available under the tradename JEFFAMINE™, from Texaco Chemical Company, Houston, Tex. as the JEFFAMINE™ series.
The linking compound of formula I is preferably epichlorohydrin although other epihalohydrins can be used. Also, trihaloalkanes can be used, such as 1,2,3trichloropropane, 1,2,44richlorobutane, 1,3,6-trichlorohexane, and the like. Instead of chlorine in the epihalohydrins and the trihaloalkanes, the corresponding bromine and iodine compounds can also be used, including compounds containing two or even all three of the above halogens.
The above reaction products are branched polymers in which analysis has shown the absence of both epoxy groups and halogen atoms from the linking compounds of formula I.
It has been discovered that when component C) is not present, the reaction products consisting only of component A) and component B) a) have excellent mobility properties, but are more highly foaming than is desired for some applications. Conversely, it has also been discovered that the reaction products consisting only component A) and component B) b) are very low foaming surfactants and can also be used as defoaming agents for aqueous compositions containing high foaming surfactants, but have limited mobility.
In the compounds of formula II, the OA groups when present are preferably all ethyleneoxy groups. Ho
Breindel Kenneth
Broadbent Ronald W.
Natale Marcie
Wiggins Michael S.
Cognis Corporation
Drach John E.
Millson, Jr. Henry E.
Truong Duc
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