Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing
Reexamination Certificate
2000-12-08
2003-01-14
Keys, Rosalynd (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Oxygen containing
C568S592000, C568S593000, C568S606000, C568S608000
Reexamination Certificate
active
06506945
ABSTRACT:
TECHNICAL FIELD
The present invention relates to a process for preparing low-foaming nonionic surfactants and more particularly to a process for preparing ether-capped poly(oxyalkylated) alcohol surfactants which have superior spotting and filming benefits in dishwashing and hard surface cleaning applications, as well as suds suppression in detergent compositions.
BACKGROUND OF THE INVENTION
Due to the varied nature of different cleaning compositions, different surfactants are better suited for some applications while being less suited or totally unsuitable for other applications. Nonionic surfactants, such as alcohol ethoxylates and alkyl glucose amides, are of considerable importance in detergent products. Under some conditions, nonionic surfactants aid cleaning of greasy soils and inhibit the formation of calcium soap. However, conventional nonionic surfactants designed for effective cleaning in laundry products form liquid crystalline phases on mixing with water. These phases can hinder the rate of mixing with water and lead to undesirable optical properties of thin films on solution drying. For example, conventional nonionics sprayed on the surface of granules to achieve target density can give rise to poor granule dissolution and residue in horizontal axis machine dispensers. Conventional nonionics formulated at high levels in liquid products can lead to poor rates of mixing with water. Conventional nonionics in window and floor cleaners can form visible liquid crystalline films on drying that increase the effort required by the consumer to achieve good results. Similarly, a nonionic surfactant for use in an automatic dishwashing machine would need to minimize foam production and not leave undesirable spots and films on the cleaned surfaces.
On account of the foregoing technical constraints as well as consumer needs and demands, product compositions are undergoing continual change and improvement. Moreover, environmental factors such as the need for biodegradable materials, the restriction of phosphate, the desirability of providing ever-better cleaning results with less product, and the use of less thermal energy and less water to assist the washing process, have all driven the need for improved compositions.
Accordingly, the need remains for new surfactants that are suitable for use in a variety of compositions which can provide improve dissolution of solid products (like bars and tablets) and granular products, improved rates of mixing of liquid products with water, improved streaking and filming performance in hard surface cleaners and automatic dishwashing products, and good cleaning, suds control and biodegradability, while avoiding incompatibility with other cleaning surfactants and/or bleach.
SUMMARY OF THE INVENTION
In accordance with a first aspect of the present invention, a process for preparing an ether-capped poly(oxyalkylated) alcohol surfactant is provided. The surfactant has the formula:
RO(R
1
O)
x
CH(CH
3
)OR
2
wherein R is selected from the group consisting of linear or branched, saturated or unsaturated, substituted or unsubstituted, aliphatic or aromatic hydrocarbon radicals having from about 1 to about 30 carbon atoms; R
1
may be the same or different, and is independently selected from the group consisting of branched or linear C
2
to C
7
alkylene in any given molecule; x is a number from 1 to about 30; and R
2
is a six membered substituted or unsubstituted, saturated or unsaturated, cyclic or aromatic hydrocarbon radical.
The process comprises the steps of:
(a) providing a vinyl ether of the formula
R
2
OCH═CH
2
wherein R
2
is as defined above;
(b) providing an alkoxylated alcohol of the formula
RO(R
1
O)
x
H
wherein R, R
1
, and x, are as defined above;
(c) reacting the vinyl ether with said alkoxylated alcohol in the presence of a catalytically effective amount of a catalyst to form the ether-capped poly(oxyalkylated) alcohol, wherein reaction of the vinyl ether with the alkoxylated alcohol is conducted as a temperature of from about 0° C. to about 60° C. and said catalyst is a sulfonic catalyst; and
(d) quenching the reaction of step (c) by the addition of a base.
These and other aspects, features and advantages will become apparent to those of ordinary skill in the art from a reading of the following detailed description and the appended claims. All percentages, ratios and proportions herein are by weight, unless otherwise specified. All temperatures are in degrees Celsius (° C.) unless otherwise specified. All documents cited are in relevant part, incorporated herein by reference.
DETAILED DESCRIPTION OF THE INVENTION
Once again, the present invention is directed toward a process for producing a low-foaming nonionic surfactant for use in detergent and other cleaning compositions.
It has been surprisingly discovered in accordance with the present invention that significant improvements in spotting and filming characteristics and, when used in conjunction with high cloud point surfactants, in the removal of greasy soils relative to conventional surfactants, are provided via the ether-capped poly(oxyalkylene) alcohol surfactants of the present invention.
The novel surfactants of the present invention comprise ether-capped poly(oxyalkylated) alcohols having the formula:
RO(R
1
O)
x
CH(CH
3
)OR
2
.
In one aspect of the present invention R is a linear or branched, saturated or unsaturated, substituted or unsubstituted, aliphatic hydrocarbon radical having from about 1 to about 30 carbon atoms, preferably from about 1 to about 20 carbon atoms. Even more preferably, R is a linear or branched, saturated, aliphatic hydrocarbon radical having from about 4 to about 18, preferably from about 8 to about 16, carbon atoms.
In the present invention R
2
is a six membered substituted or unsubstituted, saturated or unsaturated, cyclic or aromatic hydrocarbon radical.
In another embodiment of this aspect of the present invention R
2
is selected from the group consisting of:
wherein each R
3
is independently selected from the group consisting of hydrogen and linear or branched, saturated or unsaturated, substituted or unsubstituted, aliphatic hydrocarbon or alkoxy radicals having from about 1 to about 10 carbon atoms; or each R
3
is a saturated or unsaturated, substituted or unsubstituted, alicyclic or aromatic hydrocarbon radical having from about 1 to about 10 carbon atoms, which is fused to the ring; and w is an integer from 1 to 3.
In another embodiment of this aspect of the present invention R
2
is selected from the group consisting of:
wherein each R
3
is defined as above.
In another embodiment of this aspect of the present invention R
2
is selected from the group consisting of:
In one aspect of the present invention, when x is greater than 2, R
1
may be the same or different. That is, R
1
may vary between any of the C
2
to C
7
alkylene units as described above. For instance, if x is 3, R
1
may be selected to form ethyleneoxy(EO) or propyleneoxy(PO) and may vary in order of (EO)(PO)(EO), (EO)(EO)(PO); (EO)(EO)(EO); (PO)(EO)(PO); (PO)(PO)(EO) and (PO)(PO)(PO). Of course, the integer three is chosen for example only and the variation may be much larger with a higher integer value for x and include, for example, multiple (EO) units and a much smaller number of (PO) units. Similarly, ethylene, and propylene are chosen for example only and the variation may be much larger with selection of linear or branched butylene, pentylene, hexylene and/or heptylene. Preferably, x is from about 2 to about 20, and each R
1
is ethylene or propylene. More preferably, x is from about 4 to about 12, and each R
1
is ethylene.
The surfactants of the present invention can be prepared via the following process.
In one embodiment of this aspect of the present invention the step of reacting of vinyl ether with alkoxylated alcohol is conducted in the presence of a sulfonic catalyst. Suitable sulfonic catalysts include sulfonic acids and their salts such as p-toluenesulfonic acid, methanesulfonic acid, trifluoromethanesulfonic acid, 4-bromoben
Huber, Jr. Paul William
Jordan, IV Glenn Thomas
Kluesener Bernard William
Neyraval Philippe
Priou Christian
Cook C. Brant
Keys Rosalynd
The Procter & Gamble & Company
Waugh Kevin L
Zerby Kim W.
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