Compounds and compositions useful as surfactants and methods...

Details Compounds and compositions useful as surfactants and methods... Compounds and compositions useful as surfactants and methods...

2002-03-06

2003-06-10

Sellers, Robert E. L. (Department: 1712)

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

Synthetic resins

From silicon reactant having at least one...

C516S123000, C516S124000, C516S125000, C516S129000, C516S133000, C516S134000, C523S403000, C528S028000, C528S068000, C528S076000, C528S077000, C528S301000, C528S374000, C528S391000, C528S397000, C528S400000, C528S421000

Reexamination Certificate

active

06576736

ABSTRACT:

FIELD OF THE INVENTION
This invention relates to surfactants, defoaming agents, and wetting agents useful in both aqueous and nonaqueous compositions.
BACKGROUND OF THE INVENTION
Many aqueous and nonaqueous compositions, such as latex paints and oil-based paints, exhibit problems with foaming, resulting in the encapsulation of air in the liquid paints and in the coatings obtained therefrom.
There is a continuing need for surfactants that can be employed as defoaming agents in both aqueous and nonaqueous compositions. There is also a continuing need for defoaming agents and wetting agents.
SUMMARY OF THE INVENTION
The present invention relates to compounds useful as low foaming surfactants, as well as defoaming agents and/or wetting agents, which are the products of the reaction between
I) the reaction product of reactants comprising
A) a linking agent of formula I
R
4
(Y)
3
  (I)
 wherein each Y group is a halogen atom or one Y group is a halogen atom and two Y groups represent an oxygen atom, which is attached to two adjacent carbon atoms in the R
4
group to form an epoxy group, and R
4
is an alkanetriyl group containing from 3 to 10 carbon atoms; and
B) a compound of formula II
R
3
(EO)
n
(PO)
m
(BO)
p
X  (II)
 wherein R
3
is a substituted or unsubstituted, saturated or unsaturated, aliphatic or araliphatic oxy or thio group having from 1 to 36 carbon atoms or a secondary amino group having from 2 to 36 carbon atoms; n is a number of from 0 to 50; m is a number of from 0 to 50; p is a number of from 0 to 50; and X is hydrogen, or X can be a mercapto group or an amino group in place of a terminal —OH group, provided that when X is mercapto or amino; the sum of n, m, and p must be at least 1; and the mole ratio of A:B is from about 0.2:1 to about 5:1; and
II) a reactant selected from an epoxy compound, an isocyanate, a phosphate compound, a sulfate compound, an organic acid, an acrylate and a methylol urea.
The invention also relates to aqueous and nonaqueous solutions containing a surfactant-effective, and/or defoaming-effective, and/or wetting agent-effective quantity of the above reaction products.
It should be noted that reaction products I) are themselves polysurfactants, and are useful as such.
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 product of the reaction between linking agent A) and component B), the mole ratio of A:B is from 0.2:1 to 5:1, preferably from 0.4:1 to 2:1, and more preferably from 0.6:1 to 1.4:1.
The linking agent of formula I is preferably epichlorohydrin although other epihalohydrins can be used. Also, instead of chlorine in the epihalohydrins and the trihaloalkanes, the corresponding bromine and iodine compounds can also be used. Examples of trihaloalkanes are 1,2,3-trichloropropane, 1,2,4-trichlorobutane, 1,3,6-trichlorohexane and the like.
In the compounds of formula II, it is understood that EO stands for the residue of ethylene oxide and PO stands for the residue of propylene oxide and BO stands for the residue of butylene oxide.
When the X group of formula (II) is a mercapto group, the R
3
group will preferably have from about 4 to about 36 carbon atoms, examples of which include but are not limited to, alkoxylated dodecyl mercaptan and alkoxylated 1-hexadecanethiol.
The compounds of formula (II) can be alkoxylated or non-alkoxylated secondary amines. When the compounds of formula II are secondary amines, n is a number from 0 to 50, preferably from 1 to 50, m is a number from 0 to 50 and p is a number from 0 to 50, preferably from 1 to 50. Examples of the secondary amines useful for the purposes of the invention include but are not limited to, alkoxylated dibutyl amine, alkoxylated dicyclohexyl amine, alkoxylated diethylethanolamine, and alkoxylated dioctylamine.
The substituents that can be present on the substituted R
3
groups can be single or multiple substitutions such as a halogen substitution, for example Cl, Fl, I and Br, preferably trifluoro, which products therefrom are especially useful as wetting agents, a sulfur functionality such as a mercaptan or thio group; a nitrogen functionality such as an amine or amide functionality; an alcohol functionality, a silicon functionality such as a siloxane; an ether functionality; or any combination thereof.
In general, compounds of formula II wherein the sum of n, m, and p is at least 1, especially at least 2, are preferred.
When R
3
is a secondary amino group, the group preferably contains from 4 to 22 carbon atoms.
Also, when X is hydrogen p is preferably a number of from 1 to 50. When R
3
is a secondary amino group, p is preferably a number of from 1 to 50.
The nonoxy and nonthio components of the R
3
group can be any substituted or unsubstituted, saturated or unsaturated organic moiety having from 1 to 36 carbon atoms. Thus, the nonthio and the nonoxy components of the R
3
aliphatic group can be linear or branched alkyl groups, linear or branched alkenyl or alkynyl groups, saturated carbocyclic moieties, unsaturated carbocyclic moieties having one or more multiple bonds, saturated heterocyclic moieties, unsaturated heterocyclic moieties having one or more multiple bonds, substituted linear or branched alkyl groups, substituted linear or branched alkenyl or alkynyl groups, substituted saturated carbocyclic moieties, substituted unsaturated carbocyclic moieties having one or more multiple bonds, substituted saturated heterocyclic moieties, and substituted unsaturated heterocyclic moieties having one or more multiple bonds. Examples of the above include but are not limited to an alkyl group having from 4 to 22 carbon atoms, an alkenyl group having from 4 to 22 carbon atoms, and an alkynyl group having from 4 to 22 carbon atoms. R
3
can also be an arenyl group. Arenyl groups are alkyl-substituted aromatic radicals having a free valence at an alkyl carbon atom such as a benzylic group. Alkyl groups having from 4 to 12 carbon atoms are preferred, and alkyl groups having from 8 to 10 carbon atoms are most preferred. The degree of ethoxylation is preferably from 2 to about 50 with the most preferred being from about 4 to about 50 while the degree of propoxylation and butoxylation can vary from 0 to about 50, preferably from 1 to about 10. The degree of propoxylation and or butoxylation will be determined by the desired degree of solubility or miscibility in the aqueous or nonaqueous compositions of the invention. The solubility or miscibility will ultimately be determined by such factors as the number of carbon atoms in R
3
and the relative amounts EO, PO and BO.
Optionally, an additional component can be reacted with the linking agent of formula (I) and the compound of formula (II). A glycidyl ether or amine can be added to the reaction of formula (I) and formula (III). The amount of the glycidyl ether or glycidyl amine is from about 1 to about 20 mole percent based on the moles of formula (II) used in the reaction. When the glycidyl ether or glycidyl amine is added to the monofunctional starting material of formula II the ratio of formula I to formula II plus the glycidyl ether or glycidyl amine is preferably from about 0.8 to about 1.4. Examples of the glycidyl ethers include, but are not limited to, PEG 600 diglycidyl ether, TETRONIC™ 701 tetraglycidyl ether, triglycidyl di or triethanolamine, polyoxyethylene (POE) 200 tallow amine diglycidyl ether, propoxylated (POP10) trimethylol propane triglycidyl ether, propoxylated (POP7) pentaerythritol tetraglycidyl ether. Examples of glycidyl amines include, but are not limited to, tetraglycidyl 1,6-hexane diamine, tetraglycidyl JEFFAMINE™ EDR-148, and tetraglycidyl isophorone diamine.
The above reaction products I) can be obtained by the process disclosed in U.S. Pat. No. 5,827,453, the disclosures of which are expressly incorporated herein by reference.
The above reaction products I) ar

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