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UNITED STATES PATENT OFFICE 2,530,872 ESTERS 0F SULFUR-CONTAINING POLYCARBOXYLIC ACIDS James T

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UNITED STATES PATENT OFFICE 2,530,872 ESTERS 0F SULFUR-CONTAINING POLYCARBOXYLIC ACIDS James T Patented Nov. 21, 1950 2,530,872 UNITED STATES PATENT OFFICE 2,530,872 ESTERS 0F SULFUR-CONTAINING POLYCARBOXYLIC ACIDS James T. Gregory, Cuyahoga Falls, and Jacob Eden Jansen, Akron, Ohio, assignors to The B. F. Goodrich Company, New York, N. Y., a corporation of New York No Drawing. Application June 18, 1947, Serial No. 755,478 3 Claims. (Cl. 260—30.8) 2 This invention relates to new compositions of primary, secondary, or tertiary mono- or poly matter, and pertains more speci?cally to new hydroxy, substituted or unsubstituted alcohol. esters of sulfur-containing polycarboxylic acids. Among these are: primary alkyl alcohols such as It is disclosed in our copending application, Se methyl alcohol, ethyl alcohol, propyl alcohol, bu rial No. 755,476, ?led June 17, 1947, that new acids tyl alcohol, amyl alcohol, hexyl alcohol, heptyl al having the general formula cohol, octyl alcohol, nonyl alcohol, decyl alcohol, undecyl alcohol, dodecyl alcohol, tetradecyl alco hol, cetyl alcohol, octadecyl alcohol, and the like; Secondary alkyl alcohols such as isopropyl al wherein A is a polyvalent aliphatic radical hav ll) cohol, secondary butyl alcohol, secondary amyl ing its connecting valences on carbon atoms and alcohol, secondary hexyl alcohol, secondary octyl containing only atoms of carbon, hydrogen and alcohol, secondary nonyl alcohol and the like; sulfur or oxygen (1. e., a chalcogen occurring in Tertiary alkyl alcohols such as tertiary butyl one of the short periods of the periodic table), the alcohol, tertiary amyl alcohol, tertiary butyl car sulfur or oxygen being present in the divalent 15 bino, tertiary amyl carbinol, pinacoylyl alcohol. state and being connected by each of its two val and the like; ences to two different carbon atoms; R. is a biva Aromatic alcohols such as benzyl alcohol, meth lent aliphatic hydrocarbon radical, preferably ylphenylcarbinol, phenylethyl alcohol and the containing from 1 to 4 carbon atoms. and n is a like; number equal to the valence of A, preferably from 20 Alicyclic alcohols such as cyclohexanol, cyclo 2 to 4, may be readily prepared in good yields by butylcarbinol, cyclopentanol, and the like; reacting a chlorine-containing compound of the Heterocyclic alcohols such as furfuryl and tet formula M01) in, wherein A and n have the mean rahydrofurfuryl alcohols and the like; - ing set forth hereinabove, with a mercapto-acid Polyhydroxy alcohols such as glycerine, erythri of the formula 25 tol, penta-erythritol, arabitol, xylitol, adonitol, mannitol, dulcitol, sorbitol, pentaglycerine, xylyl ene glycols, and particularly ethylene glycol, di ethylene glycol, triethylene glycol, tetraethylene wherein R has the same meaning as above, in glycol, penta-ethylene glycol, trimethylene gly the presence of an alkali metal hydroxide, and T30 col, tetramethylene glycol, nonamethylene glycol, then acidifying the reaction mixture. _ undecamethylene glycol, isobutylene glycol, 2,2 We have now found that esters of acids of the dimethyl trimethylene glycol, 1,2-butanediol, 1,3 above general class, and particularly those hav butanediol, 3-methyl-1,3-butanediol, 2,3-butane ing the formula diol, pinacol, 2-ethyl-1,3-hexanediol, and the like; Unsaturated aliphatic alcohols such as allyl al cohol, methallyl alcohol, crotyl alcohol, propargyl alcohol and the like; wherein R is a bivalent aliphatic hydrocarbon Substituted alcohols such as ethoxy ethyl alco hol, ethylene chlorohydrin, cyanohydrin, 2-bro radical containing from 1 to 4 carbon atoms; X 40 is a chalcogen occurring in one of the short pe moethanol, and the like. ' riods of the periodic table; and n is a number As mentioned hereinabove the esters of this equal to the number of (X-R) groups present, invention are prepared from a sulfur-containing preferably from 1 to 4, may readily be prepared polycarboxylic acid of the type described above in good yields by a simple esteri?cation reaction. and an alcohol by a simple esteri?cation reaction. We have further found that the esters thus Such a reaction is preferably carried out by ad formed are very useful as plasticizers and modi mixing the acid and the alcohol either alone or fying agents for natural and synthetic resins and in presence of a solvent, and then heating the rubbers, cellulose derivatives and the like. reaction mixture, preferably at the re?ux tem perature of the alcohol or the solvent for a time The alcohol which is used in the esteri?cation 50 reaction may be any saturated or unsaturated su?icient for esteri?cation to occur. An esteri? aaaoma 3 4 cation catalyst such as a small amount of hydro by a partial exchange reaction between a neutral chloric acid may be used, if desired, but the esters ester ot the acid with an alcohol, and a second are obtained in high yields in a period of about higher-boiling alcohol. ‘ 2 to- 24 hours in the absence of any catalyst. The esters of this invention derived from mon When a monohydric alcohol is used the quantity ohydric alcohols are generally high-boiling liq of alcohol is preferably in excess of one mole of uids, but the esters derived from the sulfur-con alcohol for each carboxyl group present in the taining polycarboxylic acids and polyhydric alco acid, in which event neutral esters are secured, hols are often semi-solid and somewhat resinous but partial esters of the polycarboxylic acid, in in character due to polycondensation between which not all of the carboxyl groups are esteri 10 several molecules of the acid and the alcohol. ?ed, may also be prepared by using a lesser Speci?c examples of esters of this invention amount of alcohol. Mixed esters of the polycar include the following: (The nomenclature used boxylic acid with different alcohols are also con is that given in Chemical Abstracts, 39, page templated by this invention and may be secured 5924, paragraph 297). 1 dibutyl 4,10-dlthia-7-oxatridecandioate 2. dieth'yl 4,13-dithia-7,loedioxaliexadecandioate 3 dibutyl 3,9-dithia-6-oxaundecsndioate 4 . dibutyl-4,12-dithia-8~oxapentadecandioate 5 diisoamyl 4,10-dithia-f-oxatridecandioate 6 diallyl 4,10-dithia~7-oxatridecandioate 7. diethyl 3,9-dithia-6-oxaundecandioate 8 dibutyl 4,8-dithia-6-oxaundecandioate 9 dibutyl 4,13-dithia-7,10-dioxahexadecandioate dlethyl 4,10-dlthia-7-oxatridecandioate 11. di-2-ethylhexyl-4,IO-dlthIa-‘I-oxatridecandioate 12. 0-0 IHI di-n-octyl 4,7-dlthia-5-ethoxy-decandioate 13 dimethyl 4,7,10-trithiatridecsndioata asaaava diallyl 4,10-dithia-T-oxatridecandioate 15. Ha Ha ethyl butyl 6,10-dithla-8-era-7,9-dimetliyl-pentadeeandiolte HI HI '\ 0/ El di-tetrahydroturturyl 8,9-dithia-6pn-2J0-dimethyl undecandioate 17. diethyl 3,9-ditlila-6-oxa-5,7~(dl-ethoxy-methyl-thio) -undecandioate As is apparent from the above speci?c com- 20 are required, such as resistance to acids, alkalies, pounds various other compounds of the formula oxidizing agents or oils and greases. Such com A(s-a-c-o-R.). positions may be prepared by any of the usual methods, such as by mixing the polymer with the plasticizer on a hot roll mill or in an internal wherein A is a radical of the type set forth here 80 mixer. Stocks oi’ varying physical properties may lnabove and including radicals of the types be secured, depending upon the proportion of plasticizer used. Compositions containing from 10 parts or even less to 150 parts or more for each 100 parts of the polymer may be used with good results, but the use of 20 to 80 parts of plasticizer lax-B1 to 100 parts of polymer is preferred for most pur \ poses. Pigments and ?llers such as clay, barytes, carbon black, whiting, etc. which are in common use in the rubber and plastics industries may also be used in the compositions. In order to obtain wherein X is oxygen or sulfur and R is an all special properties other plasticizers may also be phatic hydrocarbon radical; used in the same compositions, and stabilizers R is a bivalent aliphatic hydrocarbon radical such as the lead salts of fatty acids or the esters either straight chain or branched and having its of unsaturated monocarboxylic acids or other connecting valences on the same or different car materials may be added to give greater stability bon atoms; toward heat and light. ' N is a number from 2 to 4, and R1 is the radical Speci?c examples of compositions in which the of a monohydric alcohol, are also included with esters of this invention are used as plasticizers in the scope of this invention. are prepared in the following manner: 15 parts All of these monohydric alcohol esters are quite by weight of polyvinyl chloride powder are placed useful as plasticizers for a wide variety of solid in a container with 10 parts of the plasticizer and plasticizable materials. mixed. This mixture is then placed on a mixing One particularly important class of materials mill at about 220° F. and its behavior observed which may be plasticized with the esters of this as the temperature of the mill rises. When the invention are the vinyl halide polymers such as 55 milling temperature is reached, the plasticizer alpha, beta, or gamma polyvinyl chloride, poly and the polyvinyl chloride are compatible and vinyl bromide, polyvinyl ?uoride, or copolymer of vinyl chloride with minor proportions of poly the stock may be out without tearing a ragged merizable unsaturated compounds such as vinyl edge. At this point the stock has no “nerve,” acetate, vinyl bromide, vinyl ?uoride, vinyl cya 60 that is, it does not shrink when a section is cut. nide, vinyl propionate, vinyl butyrate, vinylidene After plasticization is complete, the stock is chloride, vinylidene bromide, styrene, acryloni sheeted off the mill and molded into a sheet of trile, methyl acrylate, methyl methacrylate, approximately .020 inch thickness.
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