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United States Patent (19) 11 Patent Number: 4,764,566 Swedo (45

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United States Patent (19) 11 Patent Number: 4,764,566 Swedo (45 United States Patent (19) 11 Patent Number: 4,764,566 Swedo (45. Date of Patent: Aug. 16, 1988 54 PENDANT BIPHENYLENE ASA OTHER PUBLICATIONS CROSS-LINKING SITE IN AROMATIC THERMOPLASTC POLYMERS Garapon & Stille, Macromolecules, 10, 627 (1977). Recca & Stille, ibid., 10, 1344 (1977) & 11, 479 (1978). (75) Inventor: Raymond J. Swedo, Mt. Prospect, Ill. Swedo and Marvel, J. PolymerSci, Polymer Chem. Ed., 16, 2711 (1978). (73 Assignee: Allied-Signal Inc., Morristown, N.J. Ibid, 15, 683 (1977) and 17, 2815 (1979). M Primary Examiner-Theodore E. Pertilla 21 Appl. No.: 46,813 Attorney, Agent, or Firm-Thomas K. McBride; Eugene I. Snyder Fied: May 7, 1987 22 57 ABSTRACT (51) Int. Cl.' ...... 0 v 0 p a y who C08 L 71/04 Thermally stable polymers may be cross-linked by ap (52) U.S. C. .................................... 525/390; 525/397; pending biphenylene moieties to the polymer backbone, w 525/462; 525/471 then heating the modified polymer at a temperature in (58) Field of Search ................ 525/462,390, 397, 471 excess of about 300' C. The cross-link density of the cured polymer can be controlled by varying the relative 56) References Cited population of biphenylene moieties on the polymer U.S. PATENT DOCUMENTS backbone. Properties of the modified but uncured poly mer are essentially the same as those in the original 4,197,393 4/1980 Swedo et al. ....................... 528/173 4,269,953 5/1981 Brand .................................. 52.5/534 thermally stable polymer. 4,414,380 1 1/1983 Swedo ................................. 528/173 4,507,462 3/1985 Stille .................................... 528/125 14 Claims, No Drawings 4,764,566 1. 2 the prior art by appending monofunctional biphenylene PENDANT BPHENYLENE ASA CROSS-LINKING monomers onto a preformed thermally stable polymer SITE IN AROMATIC THERMOPLASTC containing aromatic nuclei, generally via a Friedel POLYMERS Crafts reaction. The result is a polymer quite similar to BACKGROUND OF THE INVENTION the original one but with the biphenylene moieties, Fiber- and fabric-reinforced resins have achieved which can effect cross-linking upon being cured at a broad usage because of their relatively high strength-to temperature in excess of about 300 C., pendant to the weight ratio and have been incorporated in articles as polymer chain or backbone. diverse as automobiles and tennis racquets. Many poly 10 The advantages of the current invention include the mers have been used as matrix resins, such as polycar bonates, epoxy resin, and polyesters generally. flexibility and convenience which result from starting It is highly desirable that such reinforced resins be with a commercially available polymer. Another ad able to be worked or molded in the field without loss of vantage is that the current approach permits one to strength. One approach to this goal has been to use a 15 directly control cross-link density by the amount of low melting polymer wich can be cured or cross-linked to a thermostable resin upon being melted, thereby biphenylene moieties incorporated, with the amount permitting working and shaping concurrent with attain incorporated itself being readily controlled. Another ment of maximum strength. advantage is that the instant approach has only a mini Where cross-linking involves a chemical reaction 20 mal effect on the properties of the polymer prior to which liberates a volatile by-product, voids may be cross-linking. produced in the resulting polymer leading to reduction in strength and limitations on shaping. This disadvan SUMMARY OF THE INVENTION tage has been overcome using the biphenylene nucleus as a cross-linking entity. Difunctionalized biphenylene 25 The purpose of my invention is to provide polymers monomers have been incorporated into polyguinoxa which undergo cross-linking upon being heated, the lines (Garapon and Stille, Macromolecules, 10, 627 cross-linking occurring via biphenylene diradicals aris (1977); Recca and Stille, ibid., 10, 1344 (1977) and ing through unsubstituted biphenylene being appended 11,479 (1978)), polyamides (Swedo and Marvel, J. Poly to the polymer chain, and a method of making such mer Sci., Polymer Chem. Ed., 16, 2711 (1978)) and 30 polyaromatic ether-ketones and ether-ketone-sulfones polymers. An embodiment comprises thermally stable (idem, ibid., 15,683 (1977) and 17, 2815 (1979)). In U.S. polymers containing aromatic nuclei in the polymer Pat. No. 4,197,393 the patentees incorporated the biphe chain and which are modified by having some aromatic nylene nucleus into the polymer chain itself and upon nuclei covalently bonded to pendant biphenylene moi subsequent heating cross-linking occurred via the 35 formed biphenylene diradical to afford a thermostable eties. In a more specific embodiment the polymer is a resin. U.S. Pat. No. 4,269,953 presents the variant poly(phenylene oxide) or a polyaryl ether-ketone-sul wherein the biphenylene nucleus is incorporated as an fone. In a still more specific embodiment the modified additive which causes cross-linking of a thermoplastic polymer contains from about 2 to about 30 mole percent polymer upon heating. biphenylene moiety. In yet another embodiment the The solutions embodied in the cited art suffer from the disadvantage that the source of the biphenylene modified polymer is prepared by Friedel-Crafts conden entity in each case is inordinately expensive. For exam sation of a monofunctional biphenylene with a ther ple, the patentees of U.S. Pat. No. 4,197,393 require a mally stable polymer containing aromatic nuclei in the biphenylene dicarboxylic acid halide, available only via 45 polymer chain. Other embodiments will be clear from a multi-step synthesis from biphenylene. The patentee the ensuing description. of U.S. Pat. No. 4,269,953 requires additives of the Structure DESCRIPTION OF THE INVENTION The invention here is a method of cross-linking ther 50 mally stable polymers containing aromatic nuclei by modifying the polymer so that the polymer will cure OOOLIO. (cross-link) at an elevated temperature. In another as pect the invention is such modified polymers them whose availability also is limited by the necessity of its 55 selves. The invention herein is grounded on the concept multi-step synthesis from the parent biphenylene. Rec of appending monofunctional biphenylene monomers ognizing the limitations accompanying these disadvan tages I have recently described an alternate solution in onto preformed thermally stable polymers containing U.S. Pat. No. 4,414,380 where the biphenylene moiety is aromatic nuclei, often by a Friedel-Crafts reaction, but introduced into the backbone of the polymer chain via 60 in any event by a reaction scheme represented by the acylation by a dicarboxylic acid where one of the acid Sequence, groups of the latter acylates biphenylene and the other acylates a diphenyl either or di(phenoxyphenyl)sulfone in a step-growth polymer. However, even the latter approach suffers from the drawback that a new copolymer must be synthesized to incorporate the biphenylene units. In this application I OLIO. have taken an approach radically different from that in 4,764,566 3 4 -continued halogen, or a sulfonyl halide. Hydroxylic (alcoholic) and olefinic functional groups are far less useful in con densation to aromatic nuclei in the polymer chain unless such nuclei bear activating substituents, e.g., halogens, but it will be recognized that the preparation of such substituted aromatic nuclei engenders additional syn thetic procedures detracting from their usefulness. Thus, the monofunctional biphenylene monomer in cludes such materials as biphenylene carboxylic acids, biphenylene carboxylic acid anhydrides, biphenylene where carboxylic acid halides, biphenylene sulfonyl halides, and biphenylene halides. Among the halides the chlo rides are most useful because of their availability and reactivity, but other halides may be used in suitable cases. Where the condensation occurs via a Friedel Crafts reaction typical Friedel-Crafts catalysts will be present, as for example aluminum chloride, boron triflu oride, ferric chloride, anhydrous hydrogen fluoride, represents a thermally stable polymer containing aro etc. matic nuclei in the polymer chain or backbone, and X is 20 a group which can react with the aromatic nuclei under The biphenylene moieties are incorporated to the suitable conditions. This approach has the advantages extent of between about 2 and about 30 mole percent, of starting with a commercially available pre-made with the preferred range being about 5 to about 10 mole polymer having known properties, and being able to percent. What is meant by, e.g., 5 mole percent of bi directly control cross-link density by the amount of 25 phenylene moieties is that 5 percent of the repeating biphenylene moiety added. Over all, the result is the units in the polymer chain bear biphenylene groups. conversion of a thermoplastic into a thermoset while That is, for every 100 repeat units in the polymer chain retaining the most desirable properties of each system. there are 5 pendant biphenylene moieties. In practice, The thermally stable polymers which may be used in one calculates the repeat unit formula weight of the the practice of this invention are those having aromatic 30 polymer, then determines the weight of polymer used in nuclei in the polymer chain or backbone. For the pur the experiment. This yields a number of moles of repeat pose of this invention a thermally stable polymer is a unit. The moles of biphenylene units added is derived polymer having a glass transition temperature, Tg, of from this calculation. If one uses 10 g of a polymer 150 C. or more. A thermoplastic polymer is one which having a repeat unit formula weight of 100, one has 0.1 becomes "plastic' upon heating, i.e., it softens and/or 35 mole of polymer. To incorporate 5 mole percent of melts upon heating and can be processed. Some generic some unit, one uses 0.005 moles of the unit in the reac thermally stable polymers, with a specific example of tion.
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