Siloxane-containing oil compositions with good spreading...

Details Siloxane-containing oil compositions with good spreading... Siloxane-containing oil compositions with good spreading...

2001-06-14

2003-12-30

Dawson, Robert (Department: 1712)

Drug, bio-affecting and body treating compositions

Preparations characterized by special physical form

Biocides; animal or insect repellents or attractants

C528S014000, C528S037000, C528S031000, C528S015000, C528S026000, C528S029000, C556S444000, C556S479000, C556S451000, C556S445000, C568S673000, C568S675000, C523S105000, C504S116100

Reexamination Certificate

active

06669949

ABSTRACT:

FIELD OF THE INVENTION
This invention relates to asymmetrical, substituted polysiloxanes which show good compatibility in a variety of oils and improve the spreading behavior of oil-based formulations to a process for preparing these asymmetrical polysiloxanes and to oil formulations containing said asymmetrical polysiloxanes. The asymmetrical polysiloxanes of this invention are used in herbicidal and pesticidal compositions, in cosmetic and pharmaceutical preparations as well as in industrial applications.
BACKGROUND OF THE INVENTION
It is well known that polysiloxanes can improve the spreading of oils on the surfaces of, for example, human skin, the waxy leaf cuticle of plants, and plastics. This class of compounds achieves this result by reducing the bulk surface tension of the preparation so that the oil-based formulation can spread over hydrophobic surfaces. Oils are generally used in the preparation of creams and lotions in cosmetic and pharmaceutical preparations. Oils also have utility in the field of tribology. Oils are also used as pesticides, herbicides adjuvants for spray mixes, or carriers for herbicides.
The reason for this is because many of the herbicides and pesticides have limited water solubility and the oils function as carriers to deliver the active ingredient to the target plant or pest. The spreading and solubilizing characteristics of these oils improve the coverage and penetration of the active ingredients into the hydrophobic surface of the target organisms. The oils used in the present compositions can also function as insecticides in their own right. Petroleum and vegetable oils are used to control infestations of insects and mite. These oils act as suffocants which interfere with the respiratory process of the arthropod. The oils exert this activity by clogging the spiracles of the insect or mite.
Oils possess good spreading and wetting properties on waxy surfaces because of their inherently low surface tension. The spreading ability of an oil-based preparation can be increased even further by adding adjuvants which modify the surface tension of the oil. For example, Schaefer in an article titled “Tenside Surfactants Detergents” in the
Journal for Theory Technology and Application of Surfactants,
April 1994, describes the use of silicone waxes to reduce the surface tension of mineral oil. These silicone waxes lower the surface tension of the organic system by reducing the surface tension of mineral oils, thereby improving the ability of the preparations to spread. As a rule, however, the spreading ability of mixtures of oils and silicone waxes is only slightly better than that of pure oils. Similarly, polysiloxanes are also used as agents to improve the spreading abilities of oils. The disadvantage of the use of these agents is the generally poor compatibility (solubility) of the polysiloxane with the oil especially when long segments consisting only of polydimethylsiloxane units are present since the solubility of the polysiloxane in the oil decreases as the number of dimethylsiloxy units increases.
This invention is concerned with organopolysiloxanes which exhibit good solubility in organic oils and have the ability to improve the ability of the oils to spread on a variety of surfaces including human skin, plants, metals, plastics and chitin.
DESCRIPTION OF THE RELATED ART
Certain Materials are known in the art to reduce the surface tension of oils. Besides silicone waxes, silicone copolymers are known to enhance the spreading properties of cosmetic emollients, oils and waxes as described by Floyd, Sarnecki and Macpherson in
Soaps, Perfumeries and Cosmetics,
vol. 69, p 26 (March 1996).
In U.S. Pat. No. 4,514,319, Kulkarni, et al. disclose antifoam compositions that utilize alkyl and polyether functional silicones as a means to reduce the surface tension of hydrocarbon oils when they are used in connection with organo-silicone surfactants.
Grüning, et al. in U.S. Pat. No. 5,645,842, herein incorporated by reference, disclose cosmetic or pharmaceutical preparations which use organopolysiloxanes to increase the spreading behavior of oils which contain ester groups. The organopolysiloxanes used in the preparation were modified with long-chain alkyl or alkoxy groups.
Murphy, et al., in U.S. Pat. No. 5,561,009 disclose that one can increase the spreading properties of oil-containing composition by adding to the composition a linear alkylsilicone of the formula
or a cyclic alkylsilicone compound
where x is an integer form 0 to 20, m is an integer from 0 to 4, n is from 1 to 5 provided that m+n is from 3 to 5, and R is an alkyl group Those alkylsilicone compounds are used as adjuvants in preparing agricultural formulations which contain mineral or vegetable oils
U.S. Pat. No. 5,658,851, also to Murphy, et al., discloses lipophilic siloxanes which decrease the surface tension of oils. Those siloxanes have the following general formula
R
a
Me
3-a
Si—[OSiMe
2
]
x
—[OSiMeR]
y
—OSiMe
3-a
R
a
where R is a lipophilic group selected from the group consisting of aryl, substituted aryl, aralkyl, alkyl phenyl ether, substituted phenylether, or alkyl alkyleneoxide groups; a is 0 or 1; x and y is 0 to 4 depending upon a, provided that the sum of x and y is greater than or equal to 6. Those siloxanes are taught to be adjuvants in oil-based herbicidal, fungicidal, or insecticidal compositions
However, the ability of the polysiloxanes known in the art to spread oils is not always satisfactory. Furthermore, polysiloxane compounds which improve spreading of one specific oil often lack the compatibility with other oils which are used according to the state of the art. Hence there is a need to develop novel polysiloxane compounds with improved spreading properties and high compatability with a wide range of natural and synthetic oils to be used in oil-based formulations.
Object of the Invention
An object of this invention is, therefore, to develop a new class of organopolysiloxanes with improved compatability with a wide range of natural and synthetic oils, a process to prepare these compounds and their use. Another object of this invention is the preparation of compositions comprising natural or synthetic oils and this new class of organopolysiloxanes, optionally with additional organo-modified silicone copolymers, which possess enhanced spreading properties relative to the oil itself, and their use. These objectives are achieved using asymmetrical polysiloxanes with superior compatability in a wide variety of natural and synthetic oil compositions,imparting an excellent spreading behaviour.
SUMMARY OF THE INVENTION
This invention relates to asymmetrically substituted polysiloxanes of the formula
wherein
R
1
and R
2
are same or different and represent linear or branched, substituted or unsubstituted, saturated or unsaturated alkyl or aryl groups with 1 to 32 carbon atoms which optionally interrupted by oxygen atoms in the hydrocarbon chains,
Z is a polyoxyalkylene radical of the structure
[—R
3
k
—O
l
—(C
n
H
2n-m
R
4
m
O)
o
R
5
],
wherein
R
3
represents the same or different bivalent alkyl or aryl radicals with 1 to 30 carbon atoms,
R
4
represents hydrogen and/or the same or different alkyl or aryl radicals with 1 to 30 carbon atoms,
R
5
represents hydrogen and/or same or different, linear or branched alkyl, aryl or acyl radicals with 1 to 30 carbon atoms, which may be substituted with hydroxy groups, halogens, unsubstituted or substituted alkyl, aryl, alkyloxy or aryloxy groups with 1 to 24 carbon atoms,
k equals 0 or 1, 1 equals 0 or 1,
m equals 0 or 1,
n equals 2 or 4,
o equals values from 1 to 100;
a equals 0 or 1, and
b equals 0 to 200;
their use in oil compositions with improved spreading properties, and a process to prepare these compounds.
This invention also provides for oil-based compositions having improved spreading properties and compatability which comprise 99.9% to 50% by weight of one or several oils; and 0.01% to 50% by weight of an organosilicone composition comprising asymmetrically substituted polysiloxan

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