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UNITED STATES PATENT OFFICE 2,430,479 BONDING of LAMINATES by MEANS of SOCYANATES Burt Carlton Pratt and Henry Shirley Rothrock, Wilmington, Del, Assignors to E

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UNITED STATES PATENT OFFICE 2,430,479 BONDING of LAMINATES by MEANS of SOCYANATES Burt Carlton Pratt and Henry Shirley Rothrock, Wilmington, Del, Assignors to E Patented Nov. 11, 1947 2,430,479 UNITED STATES PATENT OFFICE 2,430,479 BONDING OF LAMINATES BY MEANS OF SOCYANATES Burt Carlton Pratt and Henry Shirley Rothrock, Wilmington, Del, assignors to E. I. du Pont de Nemours & Company, Wilmington, Del, a cor poration of Delaware No Drawing. Application July 23, 1941, Serial No. 403,766 14 Claims. (Cl 154-140) 2 This invention relates to a process for combin amino groups is probably a urea linkage. The ing a plurality of different polymeric materials. bond with a polymer having carboxyl groups is It is at times desirable to modify a polymeric probably an amide linkage. When the polyiso material by combining therewith a second poly cyanate is reacted with a plurality of polymeric Ineric material either in apparently honogeneous 5 materials containing active hydrogen, as in the admixture or in appreciably heterogeneous rela process of the present application, the reaction tion. An example of the first class is the admix is probably complex and depends upon the rela ture of resins with cellulose derivatives in Coating tive reactivity of the hydrogens in the polymers. Compositions. An example of the Second class is To what extent the improvement in properties is the coating of regenerated cellulose film with a O due to chemical bonding (cross-linking) of dif moistureproofing coating, The polymeric mate ferent polymers and to what extent it is due to rials are combined in an effort to alter advan physical forces is not known, tageously the properties of at least one, e. g., Because of the large number of applications to the durability, moisture resistance, etc, or for which the reaction between a diisocyanate and purposes of economy. In many instances this 5 two different polymeric materials, each contain combining of the two different polymeric mate ing active hydrogen as determined by the Zere rials has been unsatisfactory because of inade witinoff method, may be put, the method of car quate bonding of the two different polymeric rying out the reaction can be varied widely. In materials. One method of carrying out the process of this This invention has as an object an improve 20 invention, the surface of one of the polymeric ment in the bond between two different polymeric materials is coated or sprayed with a solution of, materials. A further object is improved adhesion for example, hexamethylene diisocyanate in dry of one polymeric material to another. Another toluene, and the solvent allowed to flash off after object is a new material containing a polymeric which the other polymeric material is placed on material combined with at least one other differ 25 this surface and the two are then heated together ent polymeric material. under pressure. Under these conditions a firm These objects are accomplished by the follow bond is formed due apparently to reaction of the ing invention wherein an Organic compound hav isocyanate groups with both polymeric materials. ing a plurality of -XFCFY groups, wherein X is 30 In some cases it is desirable to incorporate the -C or N and Y is O, S, or NR wherein R is hydro diisocyanate in a Solution of a polymeric material gen or a monovalent hydrocarbon radical, is re containing active hydrogen and then apply this acted with two or more different separately ob Solution to the surface of another polymeric ma tained polymeric materials reactive with terial containing active hydrogen and heat the -X=C=Y groups, i. e., containing active hydro 35 Coated material to cause reaction or further re gen as determined by the Zerewitinoff method. action. In some instances it is desirable to inti (Zerewittinoff, Ber, 40, 2023 (1907); Ber., 41, 2236 mately mix the two polymeric materials before (1908) ; Kohler, J. Am. Chem. Soc., 49, 3181 reacting with the diisocyanate, Again in other (1927).) instances, it is preferable first to react one A preferred subgenus of this invention is that 40 of the polymeric materials partially with the wherein the active hydrogen containing, Sepa poly-X=C=Y compound, then to apply this rately obtained, polymeric materials are reacted material to the surface of One of the materials to with a compound having a plurality of -N-CFZ be united and then to place the other polymeric groups, wherein Z is a chalcogen (J. Am, Chem. material on top of this after which the assembly Soc., 63, 892 (1941)) of atomic weight less than 45 is heated. This method is particularly satisfac 33. This subgenus includes the polyisocyanates, tory when one of the polymeric materials to be the polyisothiocyanates and mixed isocyanate united with another polymeric material is already isothiocyanates having at least one of each of preformed. The method most suitable for any these groups. For convenience of disclosure, the particular case is easily chosen by anyone skilled invention will be discussed below largely in terms 50 in the art. of the polyisocyanates. The more detailed practice of the invention is The bond established between the polyisocyan illustrated by the following examples, wherein ate and a polymeric material having hydroxyl parts are given by weight. There are of course groups is probably thru a urethane linkage. The many forms of the invention other than these bond with a polymer having hydrogen bearing 55 specific embodiments, 2,430,479 3 4. acetic acid at 65-70° C. for 4 hours. The alde Eacample I hyde-neoprene reaction product was isolated by This example illustrates how an improved bond coagulation with alcohol followed by washing with of a cellulosic yarn to natural rubber can be se alcohol and milling to constant weight in an in cured by employing a diisocyanate and an active 5 ternal mixer. hydrogen containing rubber. Five parts of the aldehyde-neoprene was dis Two parts of trioxane-modified natural rubber Solved in 90 parts of toluene at room temperature was dissolved in 65 parts of toluene at room tem With mechanical stirring. When the solution was perature with mechanical stirring. When the homogeneous, 5 parts of hexamethylene diiso solution was homogeneous, after several hours of O cyanate was added. A high tenacity regenerated stirring, 33 parts of hexamethylene diisocyanate cellulose yarn was treated with this solution, was poured into the Solution. The Solution was dried, and wound as in Example I. This treated then placed in a shallow tank of convenient width yarn was then vulcanized to rubber and tested and length and 1,100-denier, high-tenacity, re for bond strength. The bond strength value of generated cellulose yarn, produced in accordance the modified yarn to rubber was about 560 as with the process disclosed in Parker U. S. Patent compared with 100 for the untreated yarn. The 2,133,714, was led through the solution by means increased weight of the yarn was 17%. of suitable guides and then into a drying chamber Eacample III maintained at 140 C. and provided with air cir culation. The excess Solution was permitted to This example illustrates the bonding of cellu drain back into the tank, The yarn did not come lose acetate to aldehyde-modified rubber by in contact with any support unitl it had travelled means of a diisocyanate and the utilization of through the chamber a distance of approximately this bonding to secure adhesion between cellulose 5 feet wherein it was at least partially dried. acetate and rubber. Additional passes through the chamber were made 25 A rubber-coated fabric was sprayed with a so by passing the yarn over suitable rollers. The lution containing 95 parts of toluene, 5 parts of yarn was drawn through the chamber mechani aldehyde-modified rubber, prepared from tri cally at a speed of 15 ft./min, and wound on a oxane and rubber by the general procedure re bobbin. The increased weight of the yarn result ferred to in Example I, and 5 parts of hexa ing from the above treatment amounted to 40% 30 nethylene diisocyanate. A coat of plasticized of the initial weight of the yarn. The yarn was cellulose acetate was then applied to this base then vulcanized to rubber and the strength of and the product thus obtained baked for A hour bond of yarn to rubber tested in the following at 150° C. Exceptionally good adhesion of the ale. topcoat to the rubber was thus obtained. When The yarn or cord is first combined with the the cellulose acetate coating was applied directly trioxane-modified rubber by means of the to the rubber, the adhesion was very poor. The poly-X-C=Y compound. The modified cord material prepared employing the diisocyanate is then laid on the surface of a thin coat of un also exhibited much greater resistance to whiting vulcanized rubber calendered onto a cotton back on Scrubbing. ing. The rubber and cord are then placed in a 40 Eacample IV press and vulcanized at the temperature and This example illustrates the bonding of alkyd pressure necessary to completely vulcanize the resin to regenerated cellulose by means of a di rubber. Shins are used which allow the over isocyanate. flow of a very small amount of rubber during A transparent sheet of regenerated cellulose vulcanization. During the vulcanization, the was coated with a composition consisting of 24 cords become embedded in the surface of the parts of drying oil modified alkyd resin having rubber. The bond of the cord to the rubber is an acid number of 33, 1.4 parts hexamethylene measured individually on a Scott tension testing diisocyanate, 0.4 part cobalt naphthenate drier, machine. In this test the cord is peeled from 0.01 part benzoyl peroxide, and 25 parts toluene.
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