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HHHHHH US005086083A United States Patent (19) 11) Patent Number: 5,086,083 Franklin Et Al

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HHHHHH US005086083A United States Patent (19) 11) Patent Number: 5,086,083 Franklin Et Al HHHHHH US005086083A United States Patent (19) 11) Patent Number: 5,086,083 Franklin et al. 45) Date of Patent: Feb. 4, 1992 (54) DIALKYL DICARBONATES AS BLOWING AGENTS FOR POLYMERS FOREIGN PATENT DOCUMENTS 0022994 7/1980 European Pat. Off. (75) Inventors: Ralph Franklin, Danbury, Conn.; 2053399 5/1972 Fed. Rep. of Germany . William J. Parr, Hopwell Junction, 233419 6/1976 France . N.Y.; Gerald Fesman, Teaneck, N.J.; OTHER PUBLICATIONS Barry Jacobs, Matthews, N.C. Plastic Foams, Edgar E. Hardy, vol. 1, Part 2, Chapter 14, Marcel Dekker, Inc. NY 1973 (73) Assignee: Akzo NV, Arnhem, Netherlands Plastic Foams, C. J. Benning, vol. 1, Chapter 5 (Wiley Interscience) 1969. (*) Notice: The portion of the term of this patent Plastic Foams, K. C. Frisch, J. H. Saunders, vol. 1, Part subsequent to Jul. 9, 2008 has been 2, Chap. 11, Marcel Dekker, Inc. NY 1973. disclaimed. Handbook of Foamed Plastics, R. J. Bender, p. 306–313. Encyclopedia of Chemical Technology, Kirk-Othmer, 3rd (21) Appl. No.: 724,687 Ed., vol. 17, p. 411. J. Coatings Tech., C. Thankachan, vol. 61 (769) 39-45, 22 Filed: Jul. 2, 1991 (1989) "Chemistry of Curing Reactions; Room-Tem perature Cure Coatings Based on Epoxies and Ure Related U.S. Application Data thanes'. J. Polym. Sci., Polym. Chem. Ed., Dandge & Kops, vol. 60 Continuation-in-part of Ser. No. 622,034, Dec. 4, 1990, 18, pp. 355-357 (1980) “Reactivity of N,N'-Bisme Pat. No. 5,030,664, which is a division of Ser. No. thylolpyromellitimide with Isocyanates'. 353,852, May 18, 1989, Pat. No. 4,983,320. J. Cell. Plastics, Nicholas & Gmitter, vol. 1, pp. 85-90 51) Int. Cl* ................................................ C08J 9/08 (1965), "Heat Resistant Rigid Foams by Trimerization 52 U.S.C. ...................................... 521/129; 521/94; of Isocyanate Terminated Prepolymers'. 521/97; 521/130; 521/138; 521/178; 521/181; Primary Examiner-Morton Foelak 521/182 Attorney, Agent, or Firm-James K. Poole; Louis A. (58) Field of Search ................... 521/129, 84, 97, 130, Morris 521/182, 138, 181, 178, (57) ABSTRACT (56) References Cited A method of using blowing agent compositions to pro duce foamed plastics such as polyurethanes, polyesters U.S. PATENT DOCUMENTS and the like, wherein a major auxiliary source of blow 2,906,717 9/1959 Sekimakas ............................. 260/2.5 ing agent for the foam is the decomposition of dialkyl 3,271,331 9/1964 Ender ....... ... 260/2.5 dicarbonates. The dialkyl dicarbonates can be decom 3,836,491 9/1974 Taft et al. ............................. 260/22 posed over temperatures ranging from about 10' C. to 3,849,349 11/1974 Krisch .............. ... 260/2.5 4,070,310 1/1978 Schneider et al. ... ... 260/2.5 about 45 C. when used in combination with particular 4,297,442 10/1981 Blahak .................. ... 52/128 tertiary amine decomposition catalysts. 4,983,320 1/1991 Franklin et al. .................... 521/129 5,030,664 7/1991 Franklin et al. .................... 521/129 29 Claims, No Drawings 5,086,083 1. 2 and compounds which liberate carbon dioxide under OALKYL DICARBONATES AS BLOWING the catalytic influence of basic compounds is reacted AGENTS FOR POLYMERS with organic compounds containing hydrogen atoms CROSS-REFERENCE TO RELATED which are reactive with isocyanate groups in a closed APPLICATIONS 5 mould. The organic compounds containing reactive hydrogen atoms are mixed with basic compounds and This application is a continuation-in-part of our prior /or have basic compounds chemically built into them; copending application Ser. No. 07/622,034, filed Dec. 4, the reaction can be carried out in the presence of auxil 1990, issued July 9, 1991 as U.S. Pat. No. 5,030,664 and iary agents and additives which are known in the chem incorporated herein by reference, which is a divisional 10 istry of polyurethane foams. The reaction which gener of our prior application Ser. No. 07/353,852, filed May ates carbon dioxide is carried out in the presence of 18, 1989, now U.S. Pat. No. 4,983,320. water and/or organic blowing agent. The presence of BACKGROUND OF THE INVENTION the carbon dioxide increases the time period the foam is Field of the Invention 15 in a low viscosity state, thus improving the flow proper The present invention pertains to the use of dialkyl ties of the foamable mixture. The patent indicates in the dicarbonates combined with decomposition catalysts as paragraph bridging columns 2 and 3 that the con blowing agents for polymeric compositions which rap pounds releasing carbon dioxide are not used as blowing idly progress from a fluid to a rigid or dimensionally agents and would be unsuitable as sole blowing agents. stable physical form over a time-temperature profile 20 The organic compounds which split off carbon diox which is inadequate to provide substantial thermal de ide under the catalytic influence of basic compounds composition of the dicarbonates. include pyrocarbonic acid dimethyl ester, pyrocarbonic Blowing agents are used in combination with poly acid diethyl ester, pyrocarbonic acid dibutyl ester, mers to produce polymeric foams. Polymeric foams pyrocarbonic acid dioctadecyl ester, acetic acid-car having broad application include, for example, urethane 25 bonic acid ethyl ester anhydride, propionic acid-car forms, polyester foams, and foams comprising polyvinyl bonic acid-ethyl ester anhydride, sebacic acid-bis (car chloride. Blowing agents for polymers fall into two bonic acid methyl ester)-anhydride, adipic acid bis-(car categories, chemical blowing agents and physical blow bonic acid methyl ester)-anhydride, crotonic acidcar ing agents. Commercially used chemical blowing agents bonic acid-methyl ester-anhydride and the like. The use are dominated by azodicarbonamide and physical blow 30 of carbonic acid ester anhydrides or mixed anhydrides ing agents by chlorofluorocarbons and methylene di and basic compounds to produce carbon dioxide is said chloride; both of these compound types have toxicolog to be unsuitable as the sole blowing agent for the foam, ical and ecological problems associated with them. particularly for moulded foam products. It would be desirable to have a blowing agent for Carbonic acid esters and ester anhydrides are used in polymers which comprises carbon dioxide, since this 35 combination with any inorganic or organic compounds blowing agent is non-toxic and environmentally accept which are basic in reaction, to produce the carbon diox able. Many organic compounds when heated evolve ide. Examples of basic compounds used as decomposi carbon dioxide; unfortunately, the temperature at tion catalysts include alkali metal hydroxide or alcoho-. which this occurs precludes their use in many poly lates such as sodium hydroxide, potassium hydroxide, meric foaming applications. However, there are partic sodium ethylate and potassium methylate and salts ular organic compounds which can be made to decom which are basic in reaction. Preferred basic compounds pose, releasing carbon dioxide, at lower temperatures are tertiary amines. Examples of such amines include when used in combination with a suitable decomposi triethylamine, dimethylbenzylamine, permethylated tion catalyst. diethylene trianine and triethylenediamine. U.S. Pat. No. 3,573,232 to Kloeker et al., issued 45 U.S. Pat. No. 4,110,273 to Cohnen et al., issued Au March 30, 1971, describes a process for the production gust 29, 1978 discloses a blowing agent composition of polyester foaned materials. A copolymerizable mix consisting of 1,4-butan-diol-bis-(carbonic acid ester-ben ture of unsaturated polyesters and monomeric vinyl zoic acid anhydride) and silicon dioxide. The silicon compound employs as a foaming agent a carbonic acid dioxide is credited with reducing the decomposition ester anhydride. A polyvalent metal compound is used temperature of the anhydride while increasing the yield as a catalyst to cause decomposition of the anhydride of gas substantially. This blowing agent is used for without the application of a substantial amount of heat. foaming thermoplastics such as polycarbonates, polyes U.S. Pat. No. 3,573,233 to Krefeid et al., issued ters, polyamides, and mixtures of polyphenylene ethers March 30, 1971 discloses a process of producing foamed and polystyrene at temperatures ranging from about materials from a copolymerizable mixture of unsatu 55 160 C. to about 300' C. rated polyesters and a monomeric polymerizable vinyl U.S. Pat. No. 4,297,442 to Blahak, issued Oct. 27, compound employing as a foaming agent a carbonic 1981, describes cellular elastomeric foams produced by acid ester anhydride. Particular amine compounds con foaming a polyurethane or a polyurethane prepolymer sisting of a primary or an acyclic or cyclic secondary or crosslinked with a polyanine chain lengthening agent in an acyclic or cyclic tertiary amine with alkyl, alkenyl, the presence of an organic expanding agent containing or alkenyl radicals or its quaternary annonium base or at least in part a gas forming component which reacts a primary or secondary N-monoaryl amine are used as with the polyamine chain lengthening agent or with the catalysts to cause decomposition of the anhydride with products of reaction thereof with polyisocyanates and out the application of a substantial amount of heat. split-off gas. The organic expanding agents include U.S. Pat. No. 4,070,310 to Schneider et al., issued Jan. 65 organic solvents and components that decompose at 24, 1978 describes the use of a process for the produc temperatures above room temperature (e.g. 55' C.), tion of polyurethane foams preferably having a compact splitting off gases on decomposition. Examples of ex Surface, in which process a mixture of polyisocyanates panding agents which react with amine chain lengthen 5,086,083 3 4. ers or with the reaction product of the chain lengthener heat. Non-limiting examples of such systems are poly with polyisocyanates includedicarbonic acid dialkylest urethanes, polyisocyanurates, poly(imide-urethanes), ers, alkyl carbaminates and Leusche anhydrides.
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