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United States Patent (15) 3,671,470 Case (45) June 20, 1972 54)

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United States Patent (15) 3,671,470 Case (45) June 20, 1972 54) United States Patent (15) 3,671,470 Case (45) June 20, 1972 54). RIGID POLYURETHANE COMPOSITIONS WITH IMPROVED 56 References Cited PROPERTIES UNITED STATES PATENTS 3,378,527 4/1968 Case et al................................ 260/67 (72) Inventor: Leslie C. Case, 14 Lockeland Road, 3,502,60 3/1970 Case et al............................... 260/2.5 Winchester, Mass. 0.1890 3,309,342 3/1967 Friedman. ...260/77.5 22) Filed: April 27, 1970 3,436,373 4/1969 Cox et al............................... 260/77.5 (21) Appl. No.: 32,398 Primary Evanainter-Donald E. Czaja Assistant Evanliner-Ronald W. Griffin 52) U.S.C. .................... 260/2.5 AP,260/2.5 AQ, 260/9R, 57) ABSTRACT 260/75 NQ, 260/77.5 AN, 260/77.5 AQ, 260/DIG. Polyurethane formulations based on a polyol component 24 which incorporates a hydroxyalkyl-substituted Mannich con (51) int.C. ................Cosg22/06, C08g 22/08, CO8g 22/44 densation product and a substantial quantity of cyclic 58) Field of Search................ 260/2.5 AP, 2.5 AQ, 77.5AQ, . hydrocarbon radicals are described. Such formulations yield 260/77.5AN, 75 NO rigid polyurethane foams which exhibit unusual inherent flame retardancy and exceptionally good dimensional stability under adverse conditions of temperature and humidity. 35 Claims, NoDrawings 3,671,470 2 RGDPOLYURETHANE COMPOST ONSWTH linked polyurethane compositions prepared therefrom and is IMPROVED PROPERTIES described in numerous publications. Unfortunately, however, CROSS-REFERENCESTORELATED APPLICATIONS rigid polyurethane foams derived from halo-substituted polyols usually exhibit a very objectionable lack of dimen This application is related to U. S. Pat. application Ser. No. S sional stability when subjected to changes in temperature and 61 1,826, filed Jan. 26, 1967, now U.S. Pat, No. 3,502,601 is environmental humidity. Specifically one difficulty frequency sued Mar. 24, 1970. encountered is the tendency of the foam to distort and shrink BACKGROUND OF THE INVENTION upon exposure to low temperatures. This irreversible contrac O tion in volume is generally referred to as cold shrinkage and 1. Field of the Invention results in loss of insulating power since the foam when con This invention is concerned with novel polyurethane formu tracting separates from its containing walls giving rise to blank lations, and with improved rigid polyurethane foams prepared spaces which can fill up with air, a relatively good thermal therefrom. In particular, this invention is concerned with rigid polyurethane foams derived from nitrogen-containing polyol conductor, and permit convection currents to take place. components which are characterized by having a significant 15 Likewise such polyurethane foams are well known to expand proportion of cyclic hydro-carbon radicals and secondary or irreversibly in volume to a considerable degree when sub tertiary nitrogen atoms in the form of N(hydroxyalkyl)-sub jected to elevated temperatures and high humidity. This ex stituted aminomethyl groups attached to a hydroxyalkyl-sub pansion results in a loss of insulating power due to rupture of . stituted aromatic nucleus. the closed rigid foam cells and conversion of the rigid foam 2. Description of the Prior Art 20 into an open-cell sponge. This undesirable phenomenon can Rigid polyurethane foams have attained wide commercial also lead to distortion and deformation, and even rupture, of use in recent years. These foams are conventionally prepared the boundary walls containing the foam. In order to determine by coreacting an organic polyisocyanate and a polyfunctional the degree of expansion to be expected from a foam under hydroxy-terminated compound, commonly referred to as a 25 hot, humid conditions, samples of the foam are generally sub polyol, in the presence of a blowing agent, and a great many jected to an accelerated humid-aging test in which they are ex suitable reactants and formulations are known. The polyol posed to elevated temperatures and 95-100 percent relative component may consist of a single polyol or a mixture of two humidity for a fixed period of time. The increase in volume or more different polyols. Polyols most frequently employed observed upon humid aging is exceptionally large for foams in polyurethane formulations belong to the broad classes of 30 derived from polyols with high equivalent weights, such as polyether polyols and polyester polyols and the preparation of halo-substituted polyols in which the high molecular weight of many representatives of such polyols is well documented in the halogen substituent contributes to a high equivalent the art. In order to be useful in commercial polyurethane for weight. Thus currently available rigid polyurethane foams mulations such polyols must be compatible with the other which utilize halo-substituted polyols in amounts sufficient to components of the formulation such as the polyisocyanate 35 achieve good flame retardancy exhibit exceeding poor dimen component and the blowing agent, and they also should sional stability with volume expansions of 20 to 30 percent or desirably possess viscosities which are sufficiently low at or more being observed upon humid aging. This objectional near room temperature to be readily and thoroughly miscible volume expansion also increases rapidly with decreasing den with these other components. Such ready miscibility and com sity of the foam, regrettably so, since such lower density foams patibility are essential for the production of good quality 40 would be very advantageous from a cost point of view, espe foams with uniform pore structure. These requirements of cially if the relatively expensive halo-substituted polyols are good compatibility and useful viscosity impose, however, seri employed. '. ous limitations on the reactants which can be employed to form useful rigid polyurethane foams. In addition to these es SUMMARY OF THE INVENTION sential components the polyurethane formulation will also 45 generally contain in relatively small amounts catalysts, surfac I have now discovered that rigid polyurethane foams with an tants, emulsifiers, foam stabilizing agents, fillers and other ad extraordinarily high degree of inherent flame retardancy and ditives. Such substances are employed to accelerate the rate of with exceptionally good dimensional stability can be obtained reaction between the isocyanato groups and the hydroxyl radi if the polyol component of the polyurethane formulation con cals, to control the cell size and porosity, and to obtain other SO tains two essential structural units in specific proportions. The desirable effects and properties. structural units the presence of which I have found to be es The physical properties of polyurethane foams are very im sential in the polyol component in order to achieve the results portant in commercial applications, and while in conventional of the present invention are (X) cyclic hydrocarbon radicals, state-of-the-art foams many of these properties are satisfacto hereinafter referred to as -RING- radicals, selected from ry for a number of uses, there are several foam characteristics 55 the group consisting of aromatic, partially or fully saturated which remain in need of further improvement in order to cycloaliphatic and heterocyclic radicals having at least six car eliminate undesirable shortcomings in present applications, bonatoms and from zero to sixhalo substituents selected from and in order to expand the scope of utility of polyurethane the group consisting of chloro, bromo, and iodo radicals, and foams. Especially objectionable is the flammability and com 60 (Y) N-substituted amino-methyl radicals attached to a bustibility of ordinary polyurethane foams and it has limited, phenolic residue in the ortho or para position, said radicals and in some instances entirely prevented, the use of these being identical to those present in a Mannich condensate and materials in the building and transportation industries. The having the formula prior art therefore describes attempts to provide compositions with improved resistance to ignition and flame-propagation. 65 -o-Ar-Ac Hi-N-) Specifically, the use of additives such as compounds of V phosphorus, antimony and bismuth in the formulation to im wherein m is an integer with a value varying from one to three part flame resistance to the resulting foam has been described. and Ar is an aromatic radical carrying an N-substituted Many of these additives are quite toxic, however, and in addi aminoethyl group in the ortho or para position to a phenolic tion they are often immiscible with, or difficultly dispersable 70 oxygen with the phenolic oxygen and the amino nitrogen car in, the other components of the formulation affecting adverse rying substituents selected from the group consisting of ly the physical properties of the final foam. The incorporation of phosphoro, and especially of chloro or bromo radicals as an integral part of the polyol structure has also been found to be -O-C-ERNG-C- very effective in increasing the flame-resistance of the cross 75 3,671,470 3 radicals and -(R-O)- radicals wherein R is a lower al -O-C-RING-C- kylene radical selected from the group consisting of 1,2-al kylene radicals and 1,3-alkylene radicals and n is an integer having a value of at least one and generally not more than about 2, and RING has the above-assigned meaning. For pur 5 , wherein R and RING have the above-assigned meaning. poses of this specification and claims the tertiary aryl-alkyl One method of preparing polyols suitable for use in the amino structural unit (Y)
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