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United States Patent (19) (11) Patent Number: 4,968,451 Scheibel Et Al

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United States Patent (19) (11) Patent Number: 4,968,451 Scheibel Et Al United States Patent (19) (11) Patent Number: 4,968,451 Scheibel et al. 45) Date of Patent: Nov. 6, 1990 (54) SOIL RELEASE AGENTS HAVING ALLYL-DERVED SULFONATED END CAPS FOREIGN PATENT DOCUMENTS 155710 9/1985 European Pat. Off. (75) Inventors: Jeffrey J. Scheibel; Eugene P. 180356 5/1986 European Pat. Off. Gosselink, both of Cincinnati, Ohio 1475798 6/1977 United Kingdom . (73) Assignee: The Procter & Gamble Company, OTHER PUBLICATIONS Cincinnati, Ohio S. C. Bright, C. E. Stubbs and L. Thompson, J. Appl. (21) Appl. No.: 474,709 Chem. Biotechnol, 1975, vol. 25, pp. 901-912. 22) Filed: Jan. 29, 1990 Norton et al., J. Org. Chem, vol. 33, No. 11, pp. 4158-4165 (1967). Related U.S. Application Data Primary Examiner-A. Lionel Clingman (63) Continuation of Ser. No. 237,598, Aug. 26, 1988, aban Attorney, Agent, or Firm-Leonard W. Lewis; Jerry J. doned. Yetter (51 Int, C. .................... CO7C 309/05; C08G 63/68; 57 ABSTRACT C11D 3/37 (52) U.S. C. ............................... 252/549; 252/174.19; The present invention relates to novel soil release 252/539; 252/558; 252/DIG. 15 agents, which are particular sulfonated linear tere (58) Field of Search ......................................... 252/549 phthalate ester oligomers (S.T.E. oligomers). The S.T.E. oligomers are especially suitable for formulation (56 References Cited into laundry products such as laundry detergents or U.S. PATENT DOCUMENTS fabric conditioners. Thus formulated, they provide ef. 3,821,169 6/1974 Duddey et al. ..................... 528/293 fective soil release treatments for fabrics laundered in 4,156,073 5/1979 Login .............. ... 528/295 the home. The S.T.E. oligomers can be made by radi 4,267,123 5/1981 Chew et al. 260/501-12 cal-initiated sulfonation of an allyl end-capped oligo 4,299,743 11/1981 Pierce et al. ..... 524/590 meric ester precursor, and in the preferred embodi 4,303,774 12/1981 Nachtkamp et al. ................. 528/71 ments, comprise a high proportion of disulfonate or 4,588,534 5/1986 Shepherd, Jr. et al. 260/513 R 4,598,141 7/1986 Focket al. .......................... 528/293 sulfinate-sulfonate end-capping groups. 8/1987 Ballschuh et al. .. ... 260/501.12 4,687,602 4,721,580 1/1988 Gosselink .............................. 252/90 17 Claims, No Drawings 4,968,451 1. 2 release agent may stably be introduced. Such challenges SOIL RELEASE AGENTS HAVING are generally absent from compositions used in indus ALLYL-DERVED SULFONATED END CAPS trial textile o treatments, but are well-known to manu facturers of fully-formulated consumer products. This is a continuation of application Ser. No. 5 Various materials, especially the oligomeric anionic 07/237,598, filed on Aug. 26, 1988. endcapped esters described by Gosselink in U.S. Pat. No. 4,721,580, issued Jan. 26, 1988, have been disclosed TECHNICAL FIELD for use as soil release agents. Thus, useful and relevant The present invention relates to novel soil release background can be drawn from a reading of polyester agents, which are ester oligomers of a kind which may 10 chemistry, for example as summarized in the back readily be formulated into laundry products such as ground portion of the Gosselink patent. laundry detergents or fabric conditioners. Thus formu Gosselink goes on to describe particular oligomeric lated, they are suitable for use in a home laundry opera esters which are useful as soil release agents in laundry tion. Effective, renewable soil release treatment of fab products. The ester compositions provided by Gos rics is provided. 15 Preparation of the novel soil release agents involves selink encompass substantially linear ester oligomers ester chemistry and, in the preferred embodiments, which have one or two monosulfonated end-caps, as radical-initiated sulfonation chemistry designed to pro illustrated by Q'-(-Z-O-R-OH and duce substantially linear, relatively low molecular {Q-Z-O-R-O-Z-Q' respectively, wherein Z is weight terephthalate ester oligomers having end-cap 20 terephthaloyl, R is 1,2-propylene and each of the groups ping moieties each comprising disulfonate or sulfinate Q, Q and Q' is MO3S(L)(CH2CH2O)- or sulfonate. MO3S(CH2CH2O)-. L is C1-C6 alkoxy, M is a metal cation and x and y are consistent with oligomers of low BACKGROUND OF THE INVENTION molecular weight. A substantial proportion of synthetic fabrics now in 25 The syntheses of the Gosselink esters are likely to be use are copolymers of ethylene glycol and terephthalic rather expensive, at least inasmuch as those specifically acid, sold under trade names which include DACRON, illustrated rely on reactive chlorinated starting materi FORTREL and BLUE C POLYESTER. The removal ais known to be corrosive and difficult to handle. of oily soil and oily stains, which are hydrophobic, from Gosselink has also provided other oligomeric ester the surfaces of such fabrics, which are likewise hydro 30 soil release agents; see, for example, U.S. Pat. Nos. phobic in character, is well recognized to be technically 4,702,857, issued Oct. 27, 1987; 4,711,730, issued Dec. 8, difficult to achieve using laundry compositions of the 1987; and 4,713,194, issued Feb. 15, 1987. These soil type most generally accessible to consumers. release agents, like those of the 580 patent, contain It has been recognized in the art that the provision of terephthalate, but have o nonionic, i.e., uncharged, substances which attach to the surfaces of polyester 35 capping groups. fabrics and render them more hydrophilic in character Utility of the foregoing oligomeric ester materials as is helpful in achieving improved oily soil and oily stain soil release agents in laundry products notwithstanding, release from such fabrics. Substances which have been the search for improved soil release agents has contin used in consumer products as soil release agents are ued, in view of an ongoing need to further improve the generally copolymers of moderately high (e.g., 40,000 economics, soil release properties and formulability of to 50,000) molecular weight, containing ethylene tere the soil release agents in specific laundry product matri phthalate segments randomly interspersed with poly CS ethylene glycol segments. See, for example, U.S. Pat. Soil release agents having allyl-derived or methallyl No. 3,962,152, Nicol et al, issued June 8, 1976; a soil derived end-caps are not apparently known in the art. release polyester of this type, commercially known as 45 At the outset of the work now described, such incorpo MILEASE T, is further disclosed in U.S. Pat. No. ration appeared, in chemical terms, to represent a diffi 4,116,885, Derstadt et al, issued Sept. 7, 1978; other cult goal. Thus, sulfonating a simple olefin, having only commercial variants are PERMALOSE and ZELCON one reactive group, and sulfonating an ester oligomer, (see Canadian Pat. No. 1,100,262, Becker et al, issued containing several different, potentially reactive May 5, 1981 and U.S. Pat. No. 4,238,531, Rudy et al, 50 issued Dec. 9, 1980). groups, are two very different matters. Also, it was The development of new soil release agents deliver unclear whether any soil release benefit might result, or ing technically outstanding soil release performance whether instead the sulfonated ester would then be less cost-effectively in consumer laundering and fabric care effective (e.g., overly soluble and not inclined to deposit compositions is not straightforward. To be particularly 55 on fabrics). useful, efficient adsorption and surface coverage of In view of the foregoing, it would be desirable to polyester fabric surfaces by the soil release agent must provide improved soil-release ester oligomers. occur, with minimum interference from the product It is an object of the present invention to provide such matrix which is being used as a vehicle to convey the materials, structurally altered especially in the composi soil o release agent to the fabric surface. Matrix interfer tion of the end-caps. ences, when they occur, not only decrease the effective It is a further object of the invention to provide useful ness of the soil release agent, but also reduce the clean oligomeric ester compositions comprising the novel ing, softening and/or antistatic benefits of other ingredi oligomers in admixture with other soil-release effective ents which may also be present in the product. Formu esters, such as the monosulfonate end-capped esters lability of the soil release agent is also a major consider 65 specifically disclosed by Gosselink or obvious variants ation, since the limited solubility and/or dispersibility of thereof. art-taught polyesters frequently imposes serious con It is yet another object of the invention to provide straints on the range of formulations into which the soil useful 4,968,451 3 4. methylol propane, isophorone diisocyanate, acetone, BACKGROUND ART isophorone diamine, hydrazine hydrate and water. S. C. Bright, C. E. Stubbs and L. Thompson, J. Appl. Norton et al, J. Org. Chem., Vol 33, No. 11, pp Chem. Biotechnol., 1975, Vol. 25, pages 901-912, dis 4158-4165 (1967) disclose extensive studies of solvent, close radical-initiated sulfonation of ether-bond free catalyst cation and catalyst anion effects in the ion catal linear olefins, i.e., olefinic hydrocarbons such as 1 ysis of sulfite radical-ion addition to olefins. dodecene, to simultaneously form alkane monosulfo Fock et al, U.S. Pat. No. 4,598,141, issued July 1, nates, alkane sulfinate-sulfonates and alkane disulfon 1986, describe a process for the preparation of polyes ates. Sodium metabisulfite is reacted with the linear ters with improved dye affinity. This involves reacting olefin in a mixed solvent system comprising water and 10 a dicarboxylic acid with a mixture of diols. The diol isopropanol.
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