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United States Patent [191 [Ill 4,094,943 Howarth Et Al

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United States Patent [191 [Ill 4,094,943 Howarth Et Al United States Patent [191 [Ill 4,094,943 Howarth et al. [45] June 13, 1978 PROCESS FOR SPINNING WE 2,927,098 3/1960 Goldberg ..................... 2W77.5 AP RETARDANT ELASTOMERIC 3,055,948 9/1962 Hooh et al. .................. 260/77.5 AP COMPOSITIONS 3,115,384 12/1963 Cacella et al. ....................... 264/184 3,275,578 9/1968 Pedijac et al. ............... 260/45.7 RL Inventors: James C. Fletcher, Administrator of 3,347,822 10/1967 Jenkner ........................ 260/45.7 RL the National Aeronautics and Space 3,689,440 9/1972 Glassmann ................... 260/45.7 RL Administration, with respect to an 3,717,614 2/1973 Lyssy et al. ................... 260/77.5 SP invention of John T. Howarth, 3,723,392 3/1973 Konig et al. .................. 2W77.5 SP Reading; Suresh Sheth, Somerville; 3,852,401 12/1974 Suzuki et al. ........................ 264/184 Kenneth R. Sidman, Wayland; 3,855,382 12/1974 Takeya et al. ....................... 264/182 Arthur A. Massucco, Natick, all of 3,867,336 2/1975 Zox .............................. 260/45.7 RL 3,891,599 6/1975 Marciniak et al. ........... 260/45.7 RL Mass. Primary Examiner-Jay H. Woo Appl. No.: 657,998 Attorney, Agent, or Firm-Russell E. Schlorff; John R. Filed: Feb. 13,1976 Manning; Marvin F. Matthews 1571 ABSTRACT Related Application Data U.S. Flame retardant elastomeric compositions comprised of Division of Ser. No. 374,421, Jun. 28, 1973, Pat. No. either spandex type polyurethane having incorporated 3,956,233. into the polymer chain halogen containing polyols, Int. (3.2 ............................................. B29H 21/04 conventional spandex type polyurethanes in physical U.S. c1. .................................... 264/130; 264/184; admixture with flame retardant additives or fluoroelas- 264/211; 264/236 tomeric resins in physical admixture with flame retar- Field of Search ................. 260/77.5 SP, 77.5 AP, dant additives, methods of preparing fibers of the flame 260/45.7 RL; 264/182, 184, 130, 211, 236; retardant elastomeric materials and articles of manufac- 106/15 FP ture comprised of the flame retardant elastomeric mate- References Cited rials and non-elastic materials such as polyben- zimidazoles, fiberglass, nylons, etc. U.S. PATENT DOCUMENTS 2,908,659 10/1959 Shashoua ............................ 260/32.6 6 Claims, No Drawings 2,911,390 11/1959 Smith ........................... 260/77.5 AP 4,094,943 1 Yet another object of the present invention is to pro- PROCESS FOR SPINNING FLAME RETARDANT vide flame retardant elastomeric compositions which ELASTOMERIC COMPOSITIONS are totally non-flammable in a 70% oxygen atmosphere. An important object of the present invention is to ORIGIN OF THE INVENTION 5 provide flame retardant elastomeric compositions The invention described herein was made in the per- which have good mechanical and recovery properties. formance of work under a NASA contract and is sub- Yet another object of the present invention is to pro- ject to the provisions of Section 305 of the National vide methods for the production of fibers or filaments of Aeronautics and Space Act of 1958, Public Law 85-568 flame retardant, elastomeric compositions. (72 Stat. 435; 42 U.S.C.2457) 10 These and other objects of the present invention will This is a division of application Ser. No. 374,421, filed become apparent from the description given herein and 6/28/73, now US. Pat. No. 3,956,233. the appended claims. In accordance with the above stated objects, the BACKGROUND OF THE INVENTION present invention, in one aspect, provides a flame retar- 1. Field of the Invention 15 dant polyurethane containing an organic polyisocya- The present invention relates to novel flame retar- nate and a halogen containing POlYol, the reactive dant, elastomeric compositions, methods of producing groups of the poly01 comprising hydroxyl groups, the fibers and filaments therefrom and to articles of manu- Preferred being bromine* facture incorporating the elastomeric compositions. In yet another embodiment of the present invention, 2. Brief Description of the Prior Art 20 the flame retardant compositions herein are comprised In space exploration, activity (EVA) of certain elastomeric synthetic resins and flame retar- is essential. SWh activity necessarily requires the use of dant additives, the flame retardant additives being ei- high strength elastomeric materials from which to fabri- ther halogenated organic compounds, organic Phospho- cate both garments and carrying bags used in such ac- rous compounds or mixtures of the two. Another embodiment of the present invention in- tivity. The used to form the elastomeric materials 25 must have good strength, elongation, modulus, and volves a method of producing flame retardant, elasto- meric filaments or fibers in which the above described recovery Over the extreme temperature and pressure elastomeric composition, if containing a polyurethane ranges nomallY the ‘pace equipment* encountered in of the spandex type, is spun into a plurality of fibers Of high Oxygen atmospheres Because the en- 30 which are then coalesced to a single filament, the co. countered in ’pace the garments, carrying &sced fdament being subsequently dried. Where the bags, etc. must be flame retardant lest a serious safety elastomeric polymer is of the fluorocarbon type, a hazard be posed’ certain, ‘ynthetic poly- method for producing fire retardant elastomeric fila- meric materials, have the requisite mechanical proper- ment is provided which includes extruding the elasto- ties and recovery characteristics necessary for use in 35 meric composition into a filament or fiber, treating the such environments, they suffer from the infodty that filament or fiber with a release agent and curing the thus they are not flame retardant and indeed in many obtained filament at elevated temperatures. are highly flammable. The prior art, as exemplified by U.S. Pat. Nos. DESCRIPTION OF THE PREFERRED 3,162,609, 3,076,010 and 3,134,742, discloses polyure- 40 EMBODIMENTS thane compositions showing enhanced flame retardant neflame retardant compositions of the present in- properties. However, the compositions disclosed in vention are basically of two general types; polyure- those patents are directed towards foamed Polymers thanes which have incorporated in the polymer back- and not elastomeric type material suitable for the Pro- bone, halogen containing polyols, the polyols serving to duction of fibers and filaments. The production of a fire 45 impart flame redardancy to the polymer, and conven- retardant fiber presents special problems because of the tional elastomeric materials, which vary in flammability high surface area of the fiber. Accordingly, attempts to but which are modified by the addition of certain fire resort to the techniques to render foams and other such retardant additives to produce compositions which are structures flame retardant, if applied to fibrous elasto- substantially nonflammable. meric materials tends to destroy or SeriOUSlY impair the 50 Polyurethanes which are flexible in nature and there- physical properties of the fibers thereby rendering them fore suitable for forming fibers have been given the useless for weaving, knitting or other fabric making generic term spandex. Generally speaking, the term techniques. spandex refers to elastomeric fibers in which at least 85% of the fiber-forming substance consists of seg- SUMMARY OF THE INVENTION 55 mented polyurethane. The spandex tyue polyurethanes It is therefore an object of the present invention to are refeked to as segmented because of the fact that provide a novel, fire retardant composition. they consist of an alternate arrangement of “soft” seg- It is another object of the present invention to Pro- ments consisting of either polyester or polyether blocks vide fire retardant elastomeric compositions in which and “hard” segments that generally contain aromatic the polymeric backbone has incorporated therein halo- 60 urea and sometimes urethane groups as the rigid compo- gens. nents. The rigid segments are derived from the reaction Yet another object of the present invention is to pro- of the isocyanates with urea producing compounds such vide a novel class of fire retardant elastomeric pOlWfe- as amines, water, etc. The production of polyurethanes thanes produced from halogen containing polyols. or isocyanate polymers is a well known commercial Still another object of the present invention is to 65 process, see for instance Kirk-Othmer, The Encyclopedia provide novel, flame retardant elastomeric composi- of Chemical Technology, First Supplement, pages 888 et tions in which a normally flammable elastomer is physi- seq, (Interscience, 1957). Briefly, the process involves tally mixed with certain fire retardant additives. the reaction of an isocyanate and a second compound 4,094,943 3 4 which contains an active hydrogen group such as a In imparting flame retardancy to the polyurethanes hydroxyl, amino or carboxy group. The general proce- produced herein, the “soft” segment of the polymers dure in the production of polyurethane fibers and the were modified by forming them from the halogen con- procedure generally employed herein is to treat a hy- taining polyols described above. This can be accom- droxy-terminated polyester or polyether poly01 with a 5 plished in several ways. In one method, the halogen polyisocyanate, usually at temperatures between 75 and containing poly01 can be reacted with a difunctional 125” C to produce what is known as a prepolymer. acid such as adipic acid to produce a hydroxy
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