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St. 2 Ya % Frieg March 5, 1968 R. M. EVANS ET AL 3,372,083 COMPOSITIONS AND ARTICLES FROM THE REACTION OF AN ISOCYANATE TERMINATED POLYURETHANE AND THE ISOCYANATE ADDUCT OF BITUMEN Filed March ill, l964 522SE OO 4. P P 2 s O SA 33333 S ae 27 St.2 NVENTORS Afobert A4. A razzis Berraerdous Artzg S BY 7%67.24:ya % frieg 27 3,372,083 United States Patent Office Patented Mar. 5, 1968 1. 2 tion of a concrete pavement of a road showing the use of COMPOSITIONS AND3,372,083 ARTiciES FROM THE REAC. the composition of the present invention; TION OF AN SOCYANATE TERMINATED POLY. FIGURE 2 is a perspective view partly in section of a URETHANE AND THE SOCYANATE ADDUCT tile, brick or floor covering showing the use of the binder OF BITUMEN 5 sealant of the present invention; Robert M. Evans, Chesterland, and Bernardas Brizgys, FIGURE 3 is a sectional view of a portion of a thermal Lyndhurst, Ohio, assignors to The Master Mechanics type insulating window pane using the sealant of the Company, Cleveland, Ohio, a corporation of Ohio present invention; Filed Mar. 11, 1964, Ser. No. 351,065 20 Claims. (C. 161-190) FIGURE 4 is a sectional view of a portion of a window O sash using the present sealant; and FIGURE 5 is a sectional view of a portion of a metallic Wall or ceiling panel utilizing the present sealant. ABSTRACT OF THE DISCLOSURE; According to the present invention, it has been found Floor tile, and caulking for glass and concrete contain that if a bituminous substance be used which has a rela ing a polyurethane, cured by water from the air to a 5 tively low moisture content and which is pre-reacted with solid having an elongation capacity greater than 100%, a polyisocyanate and then the intermediate product result is made from the reaction of an isocyanate terminated ing therefrom is mixed with a polyurethane prepolymer, prepolymer and the isocyanate adduct of an unmodified the final product has excellent package stability, good ad tar. This may be prepackaged in a single container and hesion to wet concrete, better physical properties than the hardened only when exposed to the moisture from the air 20 polyurethane prepolymer without the bituminous-isocya at the point of use. Also chlorinated hydrocarbons and or nate adduct, and useful rheological properties of kinds ganic silicones may be included. The caulking materials not possessed by the polyurethane prepolymer itself. At may be applied to wet joints. the same time, material costs are substantially reduced as a result of the use of relatively large amounts of bitumens, 25 which are ordinarily low in price. When this mixture is This invention relates to compositions suitable for use exposed to the atmosphere it is vulcanized or cured by as construction joint sealants, caulking compounds, roof water vapor. Moreover, it is possible to produce the prod ing materials or the like, specifically a composition of this uct or mixture in a single operation. kind lending itself to shipment, sale and application in As shown in FIGURE 1 of the drawing sealant of ready-to-apply single package form without any particular 30 the present invention has been applied as a joint between requirement for mixing at the point of use and to articles concrete blocks 2-2 which are supported by packed made with Such compositions. Sand layer 3 and aggregate or rock layer 4 of roadway In the past, compositions have been suggested for pave 5, which may be of clay or other suitable road base mate ment joints and the like consisting largely of two prin rial. In FIGURE 2 of the drawing, there is shown a floor cipal ingredients mixed at the point of use, one of them 35 tile or section of a flooring in which bits of rock 10-10 a polymeric material and the other a bituminous material Such as chips of quartz, marble or shale, etc. have Such, for example, as a petroleum residue, a coke oven been mixed with composition 11 of this invention, cast, tar or a natural asphalt. Generally, the nature of these troWelled and cured. The tiles can be molded as such and compositions is such as to require that a curing agent be laid individually in a sealant of this invention or can be included with the bituminous portion to solidify the poly 40 cast in place over concrete, wood or other subflooring. meric material. From the standpoint of the user, mixing After curing, the tile or floor can be polished or its surface at the point of application is a disadvantage, as for ex made smooth, if desired. FIGURE 3 shows an insulating ample, When it requires the use of elaborate proportion type window pane in which two pieces of glass 15-15 ing apparatus and skilled attendants to operate it. In many are secured together at least along their inner edges by cases, the compositions have a decided tendency to foam; 45 means of Sealant 16 of the present invention to form dead in others, even if there is no foaming, the products have air space 17 which can be partially exhausted, filled with relatively poor physical properties, particularly as regards dry air and so forth. FIGURE 4 discloses a piece of glass strength, elongation and adhesion to wet surfaces. 20 Secured in metal channel 21 of a window sash by An even more serious weakness has characteristically means of sealant 22 of the present invention. FIGURE resided in the inability of such compositions to bond 50 5 discloses wall panel 25 comprising metal sheets such as tenaciously to new concrete of high water content or old Steel sheets 26-26 secured together by the present seal concrete wetted down by rain or melting snow. ant 27. Essentially all of the space between sheets 26-26 Accordingly, it is an object of the present invention to may be filled with sealant 27 or if desired only a portion provide Sealants, caulking compounds and roofing mate may be filled with sealant to secure the sheets together. rials and the like characterized by their ability to be easily 55 THE BITUMINOUS ADDUCT applied, by general freedom from foaming, by having im The bituminous substance employed in the practice of proved physicals, and by having improved dry and wet the present invention can be any natural or synthetic bi adhesive strength to concrete. tuminous Substance (bitumen, pyrobitumen, asphalt, as Another object of this invention is to provide products 60 phaltite, asphaltic pyrobitumen, nonasphaltic pyrobitumen, or articles of manufacture in which the parts or elements tar and/or pitch) containing asphaltene or tar-like com are Secured in place by the sealant or composition and the ponents. For example, there can be used pine tar or tar like of the present invention. which is used for cutting hard resins, coaltar, coke oven Another object is to provide a method for making a or gas plant tar, road tars or oils, pitches, roofing pitches, 65 other coal tar fractions, cracked, straight run or natural composition useful as a sealant, caulking compound, roof asphalts, petroleum distillation residues and asphalts, cut ing material and so forth. asphalts, albino asphalts and so forth as well as synthetic These and other objects and advantages of the present bituminous substances. Examples of many bituminous invention will become more apparent to those skilled in Substances which can be used are shown in the book by the art from the following detailed description, examples 70 Abraham, "Asphalts and Allied Substances, D. Van and drawing in which: Nostrand Co., Inc., New York, 5th ed., vol. 1, 1945, es FIGURE 1 is a vertical cross sectional view of a por pecially pages 56-69. Still other materials can be used such 3,372,083 3. 4. as the high boiling tar acids which may be obtained by and 2,6-tolylene diisocyanates or other polyisocyanate treating tars with caustic, neutralizing, and fractionating mixtures can be used. It will be appreciated that, where to get the portion boiling between about 195-340 C. con isocyanates are used having more than two isocyanato taining relatively a high percentage of beta naphthol, re groups, care should be observed to avoid too much cross sorcinol, and a small amount of xylenol and other Sub 5 linking which might give an undesirable increase in vis stances (the lower boiling fraction, 21.0-225 C., contains cosity of the bituminous substance or make it a solid or xylenol, phenols and so forth). The high boiling tar acids gel. If the bituminous substance has a sufficiently high are useful in making light colored or white products. Aro molecular weight or high isocyanate equivalent this prob matic resins such as coumarone-indene polymers or resins, lem may not be too serious. chlorinated biphenyl, cyclic unsaturated petroleum resins Isocyanates which are preferred for reaction with the and the like which contain, or to which have been added 10 bituminous substances are organic diisocyanates having high boiling tar acids can also be used. Thus, the bitumi at least 6 carbon atoms up and to a total of 18 carbon nous substances can be naturally occurring substances, or atoms in a chain between isocyanato groups. The chain their derivatives or by-products, synthetics, or they may be may be part of an aliphatic chain or of a cyclic or aro the products or by-products of the chemical, coal, petro 5 matic ring. A portion, 1 to 4, of the total hydrogen atoms leum or steel industries and so forth. It is preferred that of the total of these carbon atoms may be substituted the bituminous substance be a liquid at temperatures of with halogen atoms, i.e., Cl, Br, I and/or F atoms.
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