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United States Patent (19) 11) Patent Number: 4,617,057 Plueddemann 45) Date of Patent: Oct

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United States Patent (19) 11) Patent Number: 4,617,057 Plueddemann 45) Date of Patent: Oct United States Patent (19) 11) Patent Number: 4,617,057 Plueddemann 45) Date of Patent: Oct. 14, 1986 54 OIL AND WATER REPELLENT COATING COMPOST ONS OTHER PUBLICATIONS N. L. Jarvis et al. in Contact Angle, Wettability and Ad (75) Inventor: Edwin P. Plueddemann, Midland, hesion, pp. 317-331, American Chemical Society, Wash Mich. ington, D.C. (1964). 73 Assignee: Dow Corning Corporation, Midland, Primary Examiner-Amelia B. Yarbrough Mich. Attorney, Agent, or Firm-James E. Bittell 21 Appl. No.: 741,642 57 ABSTRACT An oil and water repellent coating composition is dis 22 Filed: Jun. 4, 1985 closed. The composition comprises a blend of an ami 51) Int. Cl................................................. CO9K 3/18 noorganosilane, a perfluorinated organic compound 52 U.S.C. ........................................................ 106/2 and a resin selected from the group consisting of colloi 58) Field of Search ............................ 106/2; 8/115.54 dal inorganic-based siloxane resin, poly (dialkylsilox ane)-monoorgano substituted silisesquioxane block co 56) References Cited polymer, acrylic polymer and copolymer, ethylene U.S. PATENT DOCUMENTS vinyl acetate latex and styrene-butadiene latex. The silane and perfluorinated organic, combined, constitute 3,317,629 5/1967 Quaal ....... ... 260/827 from 0.1% to 10% by weight of the total resin solids in 3,681,266 8/1972 Domba .................................. 260/25 a solution or suspension of the blend. A method of coat 4,070,152 1/1978 Pentz .................................... 8/115.6 ing a smooth substrate or treating a fabric to render the 4,410,563 10/1983 Richter et al. ...................... 427/08 respective surface oleophobic and hydrophobic is fur FOREIGN PATENT DOCUMENTS ther disclosed. 142958 8/1983 Japan ........................................ 3/18 147483 9/1983 Japan ... 15 Claims, No Drawings 4,617,057 1. 2 Jarvis et al. (Contact Angle, Wettability, and Adhesion, p. OIL AND WATER REPELLENT COATING 317, American Chemical Society, Washington, D.C., COMPOSITIONS 1964) that only certain combinations of fluorinated or ganic compounds and (extending) polymers result in This invention relates to the field of protective coat 5 low energy surfaces. Moreover, this reference teaches ings. More specifically, this invention relates to hydro that a critical balance of organophilic/organophobic phobic and oleophobic coating compositions which character (i.e., the precise solubility/insolubility bal impart water and oil repellent properties to substrates ance of the fluorinated compound in the polymer) is coated therewith. These substrates, in turn, may com required of the modifying fluorinated compound if the prise hard, smooth forms such as metal, glass or plastic 10 modified polymer combination is to produce a uniform, as well as fabrics of various types. clear, high quality film, in addition to low surface en ergy. It is therefore recognized in the art that there is no BACKGROUND OF THE INVENTION a priori way to determine how much of, and indeed, Many industrial applications of materials require the which of the many available fluorinated organic com surfaces of these products to possess hydrophobic and 5 pounds, or other low surface energy modifiers, can be oleophobic character for both aesthetic as well as prac successfully combined with a given polymer to produce tical reasons. Coated glass cloth, employed in pre-fab the desired hydrophobic/oleophobic character while ricated air-supported structures such as sports stadia, maintaining a uniform, high quality surface. for example, should have an oil repellent surface so as to prevent unsightly dirt accumulation. High voltage elec 20 SUMMARY OF THE INVENTION trical insulators, likewise, must be hydrophobic and This invention relates to an oil and water repellent "self-cleaning' in contaminated environments such that coating composition, comprising: surface dirt and moisture, and therefore undesirable arc (a) a resin selected from the group consisting of col tracking, are kept to a minimum. Furthermore, many loidal inorganic-based siloxane resin, poly(dialkylsilox coatings, such as those applied to optics, mirrors, wind 25 ane)-monoorgano substituted silisesquioxane block co shields, solar collectors, and greenhouses, must retain polymer, acrylic polymer and copolymer, ethylene clarity to be efficient light transmitters, and therefore vinyl acetate latex and styrene-butadiene latex, also have to be "self-cleaning' (e.g., as by rainfall) rela (b) an aminoorganosilane of the general formula tive to the uncoated surfaces. Finally, as yet another illustration of the utility of low surface energy coatings, 30 the treatment of various fabrics for water repellency and stain resistance (i.e., oleophobicity) has become a Ri R3 Rn, major commercial success. It is known in the coating arts to employ silicones to wherein R is selected from the group consisting of achieve hydrophobic surfaces and treated fabrics. Like 35 hydrogen, alkyl of one to four carbon atoms or wise, perfluorinated organic coatings and fabric treat ments are known to confer oleophobic properties. In deed, these two classes of materials have been effec -R'OR)- tively combined in U.S. Pat. No. 4,410,563 to coat opti Rn, cal glass surfaces as well as in U.S. Pat. No. 3,681,266 to treat fabrics. R2 is an alkylene group of two to four carbon atoms, Unfortunately, the perfluorinated organic com R3 is hydrogen or alkyl of one to four carbon atoms, R. pounds are quite costly and therefore not suitable for is an alkylene group of three to four carbon atoms, R. many applications in which oleophobic surfaces would and R6 are alkyl groups of one to four carbon atoms otherwise prove desirable. Such disadvantage was par 45 each, n is zero to four and m is zero or one; and tially overcome by U.S. Pat. No. 3,317,629, wherein (c) a perfluorinated organic compound of the general fluoroalkylsiloxanes were "extended' with acrylic pol formula: ymers and used to treat a variety of fabrics to obtain hydrophobic and oleophobic character. In a similar RY fashion, U.S. Pat. No. 4,070,152 employs a copolymer 50 of a maleic-anhydride copolymer, a fatty acid amine wherein Rf is a straight or branched perfluoroalkyl and an aminoorganopolysiloxane as an extender for group of four to 18 carbon atoms and Y is selected from fluorinated "textile treating resins.” It discloses im the group consisting of -COOH, -COOR, wherein R proved oil and water repellency and better retention of is alkyl or alkoxyalkyl of one to six carbon atoms and repellency after laundering and dry cleaning relative to 55 wherein the combined amount of the aminoorganosi use of the textile treating resins alone. Still further ex lane and the perfluorinated organic compound com amples of this general concept are provided by Japanese prises between about 0.1 and about 10 percent by Pat. Nos. 142,958/83 and 147,483/83 which combine a weight of said resin and the mole ratio of the perfluori perfluoroalkyl-containing silane and a silane coupling nated organic compound to the sum of primary and agent with water-glass and colloidal silica, respectively, 60 secondary amine group(s) in the aminoorganosilane is for use as a water and oil repellent agent for glass sur fixed between about 0.33 and about 1.0. faces. Although such attempts to reduce the expense of DETAILED DESCRIPTION OF THE fluorinated treating resins have been successful in that INVENTION less of the costly ingredient is required to achieve the 65 It has been discovered that, when certain polymers or same extent of surface modification, complex and costly resins are modified with relatively small quantities of a reaction schemes are sometimes required to produce the perfluorinated organic compound and an aminoor disclosed components. Furthermore, it is known from ganosilane, compositions result which exhibit excellent 4,617,057 3 4 water and oil repellency when employed in bulk, as most preferred aminosilane. Other suitable aminosilanes coatings or as fabric treating resins. One aspect of the include invention, therefore, teaches "extending' or diluting fluorinated organic compounds with certain less expen sive polymers and resins, thereby producing hydropho- 5 bic and oleophobic coating and fabric treating composi tions which are less costly than these compounds alone, or in combination with, an amino-functional silane. Alternatively, the invention discloses the modification of the particular polymers or resins within its scope with the fluorinated organic compounds and amino functional silanes so as to impart hydrophobic and oleo phobic character to the surfaces of these polymers or resins, without attendant untoward effects upon other properties. 15 The invention may be practiced by simply blending The aminoorganosilanes are well known in the art and the three components, at room temperature, either in are typically formed by the reaction of chloroalkylalk solution or suspension, and using that solution or sus oxysilanes with organic amines. For example, the bis pension to coat a substrate or treat a fabric. The order of structures, including formula III above, have been de blending is not critical, so that, for example, the resin 20 scribed in U.S. Pat. No. 4,448,694 and are formed by and silane may be blended together and then the perflu heating the respective amine with the appropriate chlo orinated compound added, or the resin and the perfluo roalkylalkoxysilane in a 1:2 molar ratio. The resultant rinated compound may be blended together and then aminoorganosilanes are generally not pure species and the silane added. In the preferred, as well as most con several side products coexist with the main component. venient, embodiment, a mixture of the perfluorinated 25 Generally either unpurified reaction products or more organic compound and aminoorganosilane may be pre purified portions of the main species can be employed pared (in solution or suspension) and an appropriate for the purposes of this invention. portion thereof used to modify the particular polymer The perfluorinated organic compound employed, or resin.
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