US3141897A - Reaction product of maleic anhydride unsaturated fatty acid adduct and polyethylene glycol - Google Patents

Reaction product of maleic anhydride unsaturated fatty acid adduct and polyethylene glycol Download PDF

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Publication number
US3141897A
US3141897A US143566A US14356661A US3141897A US 3141897 A US3141897 A US 3141897A US 143566 A US143566 A US 143566A US 14356661 A US14356661 A US 14356661A US 3141897 A US3141897 A US 3141897A
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US
United States
Prior art keywords
polyethylene glycol
maleic anhydride
fatty acid
adduct
monoester
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US143566A
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English (en)
Inventor
Samuel B Crecelius
Thomas E Brunelle
Larry M Rue
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Ecolab Inc
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Economics Laboratory Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority to BE622310D priority Critical patent/BE622310A/xx
Application filed by Economics Laboratory Inc filed Critical Economics Laboratory Inc
Priority to US143566A priority patent/US3141897A/en
Priority to DEE23459A priority patent/DE1202002B/de
Priority to GB33486/62A priority patent/GB980730A/en
Priority to FR908586A priority patent/FR1333060A/fr
Priority to SE9699/62A priority patent/SE308717B/xx
Priority to DK394762AA priority patent/DK104564C/da
Application granted granted Critical
Publication of US3141897A publication Critical patent/US3141897A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
    • C11C3/003—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fatty acids with alcohols
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/008—Polymeric surface-active agents
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
    • Y10S516/01—Wetting, emulsifying, dispersing, or stabilizing agents
    • Y10S516/06—Protein or carboxylic compound containing

Definitions

  • This invention relates to novel high molecular weight acidic ether esters of a surface active nature which are particularly effective detergents'for cleaning operations where an acidic medium is desired.
  • fatty acid soaps are excellent detergents when employed in soft water.
  • sodium and potassium fatty acid soaps interchange with the calcium ion and precipitate as an insoluble scum thereby being rendered inactive for detergent purposes.
  • fatty acid soaps in recent years have been supplanted by synthetic detergents such as the anionic alkyl aryl sulfonates and the non-ionic polyalkoxy ethers. These syn thetic detergents are not precipitated in hard water and have good wetting and detergent properties.
  • synthetic detergents such as the anionic alkyl aryl sulfonates and the non-ionic polyalkoxy ethers.
  • novel substances provided in accordance with the present invention consist of compositions which are essentially monoesters of unsaturated fatty acid-maleic anhydride adducts and polyethylene glycols having a molecular Weight of from about 200 and not more than about 1000.
  • the novel monoesters of the invention are made by heating the adduct with a suitable polyethylene glycol at a temperature of not more than about 120 C. in proportions of about 1 mole of adduct per mole of polyethylene glycol.
  • the adducts which are used for reaction with the polyethylene glycols to form the monoesters of the present invention are adducts of maleic anhydride With unsaturated fatty acids. These adducts are readily prepared by methods well known in the art which generally consist of heating approximately equivalent proportions of the reactants at temperatures from about 100 to 220 C. for periods ranging from several minutes up to several hours.
  • the adducts contain, in addition to a carboxyl group, a dibasic anhydride functional group.
  • the adducts react 3,141,897 Patented July 21, 1964 with the polyethylene glycol through the anhydride functional group to form a monoester product having two free carboxyl groups therein.
  • the acids employed in making the adducts are the unsaturated acids of the fatty acid type having at least about 10 carbon atoms per molecule. Mixtures of such fatty acids can also be satisfactorily utilized. Representative acids which can be employed include oleic, linoleic, clupanodonic, undecylenic, erucic, dehydrated ricinioleic, eleostearic, beta liconic, arachidonic, licanic, linseed oil fatty acids, soya oil fatty acids, and dehydrated castor oil fatty'acids.
  • One preferred fatty acid mixture suitable for use in the invention is the acid mixture comprising refined tall oil fatty acids.
  • Tall oil which is available commercially in various grades is the liquid residue obtained from digesting wood to wood pulp in the paper industry. It is a dark brown viscous liquid with the acid components thereof consisting essentially of 14 to 18 carbon acids. The unsaturated acids, oleic and linoleic acids, are the predominant acid components. Myristic acid, palmitic acid, heptadecanoic acid, stearic acid and linolenic acid are usually present as minor constituents. Tall oil when fractionally distilled yields various grades of fatty acid containing from about 95 to 99% fatty acids and from 4% to 0.2% unsaponifiables and from 5 to 0.2% rosin acid. Refined tall oil fatty acids are of this type.
  • polyethylene glycols which are employed in producing novel chemical substances of the present invention are polymers having the general formula:
  • n is a numeral from about 4 to about 23.
  • Polyethylene glycols are currently available in technical quan tities and polymeric grades corresponding to molecular weight ranging from about 200 to 6000 or more.
  • the polyethylene glycols employed in the present invention are those having a molecular weight from about 200 to not more than about 1000.
  • Preferred polyethylene glycols are those having a molecular weight from about 300 to about 800.
  • the maleic anhydride unsaturated organic acid adducts are reacted with the polyethylene glycols in substantially equimolar proportions at a temperature ranging from about room temperature up to but not substantially exceeding 120 C.
  • this esterification reaction is carried out at a temperature from about to C. for a period of time ranging from about 10 to 20 minutes. It is important that the esterification reaction be carried out for a relatively short period of time, generally not substantially more than about 20 minutes and at a temperature substantially not in excess of C. in order to control and direct the esterification reaction.
  • the polyethylene glycol reacts with the adduct at the location of the anhydride functional group to form the desired monoester and simultaneously set free a carboxyl group so that the resulting monoester will contain two free carboxyl groups per molecule. No water is liberated during the partial esterification when conducted under the specified conditions.
  • This reaction can be illustrated as follows, the adduct of maleic anhydride and 3 linoleic acid being used as representative of the adduct reactants.
  • the monoester products of the present invention have a unique structure wherein the ester linkage is located at an intermediate point along the fatty acid chain adjacent to a carboxyl group but remote from another free carboxyl group located at the end of the acid chain.
  • the novel reaction products thus are combination nonionic and anionic compounds in that they contain a noniom'c group (polyethylene glycol portion) which imparts water solubility and surface activity thereto and in addition contain anionic carboxyl groups which impart acidic properties to the product.
  • EXAMPLE I Approximately 141.2 grams /z mole) of oleic acid are placed into a 500 milliliter 3-necked flask fitted with a reflux condenser, a thermometer and stirring apparatus. Approximately 49.0 grams /2 mole) of maleic anhydride is then added to the flask and the mixture heated by stirring to a temperature of about 210-220 C. and maintained at that temperature for about 3 hours. The resulting intermediate maleic anhydride-oleic acid adduct is cooled and to it is added approximately 300 grams /2 mole) of a polyethylene glycol (Dow Chemical Company Polyglycol E-600) having an average molecular weight of about 570-630.
  • a polyethylene glycol Dow Chemical Company Polyglycol E-600
  • the mixture is then heated to a temperature of about 110-120 C. and maintained at this temperature for about 20 minutes. After cooling to room temperature the product is a red-brown slightly viscous transparent liquid, having a pH of about 2.5-3 in liquid form and a refractive index of 1.4708 at 26.5 C.
  • EXAMPLE II Approximately 140.0 grams /zmole) of soya oil fatty acid are placed into a 500 milliliter 3-necked flask fitted with a reflux condenser, a thermometer and stirring apparatus. Approximately 49.0 grams A2 mole) of maleic anhydride is then added to the flask and the mixture heated with stirring to a temperature of about 210-220 C. and maintained at that temperature for about 3 hours. The resulting intermediate maleic anhydride-soya oil fatty acid adduct is cooled and to it is added approximately 300 4 grams /2 mole) of a polyethylene glycol (Dow Chemical Company Polyglycol E-600) having an average molecular weight of about 570-630.
  • a polyethylene glycol Dow Chemical Company Polyglycol E-600
  • the mixture is then heated to a temperature of about -120 C. and maintained at this temperature for about 20 minutes.
  • the product is then cooled to room temperature at which temperature it solidifies.
  • the product has a pH of about 2.5-3 in liquid form and a refractive index of 1.4764 at 250 C.
  • EXAMPLE HI Approximately 578 grams (2 moles) of refined tall oil fatty acids and 196 grams (2 moles) of maleic anhydride are charged into a two-liter, 3-necked reaction flask fitted with a reflux condenser, a thermometer and mechanical stirrer. The reaction mixture is heated to approximately 215 C. with agitation and held Within the range of 215 to 225 C. for a period of three hours after which the product is cooled.
  • the product, designated herein as Intermediate A is a dark reddish brown liquid having a pH at 100% concentration of 3-3.5 and an index of refraction at 22 C. of 1.4871. Extraction of an aliquot sample with water shows no free maleic anhydride to be present.
  • the tall oil fatty acids employed had the following inspection:
  • the said monoester being formed by opening of the anhydride functional group of the said adduct and reaction of the polyethylene glycol therewith to form simultaneously the monoester and a free carboxyl group.
  • composition of claim 3 wherein the mixture of organic acids comprises refined tall oil fatty acids.
  • composition of claim 3 wherein the mixture of organic acids is soya oil fatty acids.
  • novel substances of the present invention can be used in a variety of applications where surface active agents find utility. These new substances have detergent properties and can be advantageously employed in cleaning applications wherein acidic cleaning media is desired such as, for example, in the cleaning of felts in paper mill operations.
  • the method of producing a chemical reaction product which comprises reacting at a temperature of not more than about 120 C. and for a period of time not substantially exceeding about 20 minutes, substantially equimolar proportions of a polyethylene glycol having a molecular weight from about 200 to about 1000 and a maleic anhydride unsaturated organic at least 10 carbon atom containing fatty acid adduct.
  • the method of producing a chemical reaction product which comprises reacting at a temperature from about to C. for a period of time not substantially exceeding about 20 minutes substantially equimolar proportions of a polyethylene glycol having a molecular weight from about 200 to about 1000 and a maleic anhydride unsaturated organic at least 10 carbon atom containing fatty acid adduct.
  • the method of producing a chemical reaction product which comprises reacting at a temperature from about 85 to 95 C. for a period of time not substantially exceeding about 20 minutes substantially equimolar proportions of a polyethylene glycol having a molecular Weight from about 300 to about 800 and a maleic anhydride unsaturated organic at least 10 carbon atom containing fatty acid adduct.
  • the method of producing a chemical reaction product which comprises reacting at a temperature of not more than about C. and for a period of time not substantially exceeding about 20 minutes substantially equimolar proportions of a polyethylene glycol having a molecular weight from about 200 to about 1000 and an adduct of maleic anhydride with a mixture of unsaturated organic at least 10 carbon atom containing fatty acids.
  • the method of producing a chemical reaction product which comprises reacting at a temperature of not more than about 120 C. and for a period of time not substantially exceeding about 20 minutes substantially equimolar proportions of a polyethylene glycol having a molecular weight from about 200 to about 1000 and an adduct of maleic anhydride and tall oil fatty acids.
  • the method of producing a chemical reaction product which comprises reacting at a temperature of not more than about120" C. and for a period of time not substantially exceeding about 20 minutes substantially equimolar proportions of a polyethylene glycol having a molecular weight from about 200 to about 1000 and an adduct of maleic anhydride and soya oil fatty acids.
  • the method of producing a chemical reaction product which comprises reacting at a temperature of not more than about 120 C. and for a period of time not 10 2,950,310

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Polyesters Or Polycarbonates (AREA)
  • Polyethers (AREA)
  • Paper (AREA)
  • Detergent Compositions (AREA)
US143566A 1961-10-09 1961-10-09 Reaction product of maleic anhydride unsaturated fatty acid adduct and polyethylene glycol Expired - Lifetime US3141897A (en)

Priority Applications (7)

Application Number Priority Date Filing Date Title
BE622310D BE622310A (en(2012)) 1961-10-09
US143566A US3141897A (en) 1961-10-09 1961-10-09 Reaction product of maleic anhydride unsaturated fatty acid adduct and polyethylene glycol
DEE23459A DE1202002B (de) 1961-10-09 1962-08-30 Verfahren zur Herstellung von Polyaethylenglykolestern
GB33486/62A GB980730A (en) 1961-10-09 1962-08-31 Surface active acidic ether esters
FR908586A FR1333060A (fr) 1961-10-09 1962-09-04 éthers-esters acides tensio-actifs
SE9699/62A SE308717B (en(2012)) 1961-10-09 1962-09-07
DK394762AA DK104564C (da) 1961-10-09 1962-09-10 Fremgangsmåde til fremstilling af en ester af en polyethylenglycol og et additionsprodukt af maleinsyreanhydrid og en umættet fedtsyre.

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US143566A US3141897A (en) 1961-10-09 1961-10-09 Reaction product of maleic anhydride unsaturated fatty acid adduct and polyethylene glycol

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BE (1) BE622310A (en(2012))
DE (1) DE1202002B (en(2012))
DK (1) DK104564C (en(2012))
GB (1) GB980730A (en(2012))
SE (1) SE308717B (en(2012))

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3300424A (en) * 1961-04-12 1967-01-24 Vianova Kunstharz Ag Process for the production of hardenable products by multiesterification
US3433754A (en) * 1964-04-13 1969-03-18 Vianova Kunstharz Ag Process for the production of synthetic resins hardenable by multiesterification
US3499007A (en) * 1964-12-05 1970-03-03 Cassella Farbwerke Mainkur Ag Addition products of maleic anhydride to polyalkylene ethers
US3624013A (en) * 1967-02-10 1971-11-30 Desoto Inc Heat-hardenable water-dispersible resins derived from polyhydric polyethers and mixtures thereof with benzoguanamine-formaldehyde condensates particularly adapted for electrodeposition
US3981895A (en) * 1973-12-11 1976-09-21 Dulux Australia Ltd. Novel autoxidative derivatives of maleinized monocarboxylic fatty acid
US3996054A (en) * 1971-09-24 1976-12-07 Minnesota Mining And Manufacturing Company Color photographic developing solution
US4028283A (en) * 1975-09-30 1977-06-07 Kao Soap Co., Ltd. Granular or powdery detergent composition
US4261851A (en) * 1979-07-23 1981-04-14 Johnson & Johnson Products, Inc. Low-irritating detergent composition
US4317740A (en) * 1980-04-22 1982-03-02 Union Camp Corporation Water-soluble polyesters
US20080020957A1 (en) * 2006-05-09 2008-01-24 Nelson Lloyd A Water soluble rosin acid esters
US20080076822A1 (en) * 2006-09-27 2008-03-27 Miura Co., Ltd. Disinfectant
US20150164966A1 (en) * 2012-05-14 2015-06-18 Hankkija Oy Saponified tall oil fatty acid for use in treatment and animal feed supplements and compositions
US9789143B2 (en) 2013-05-14 2017-10-17 Hankkija Oy Use of tall oil fatty acid
US9962353B2 (en) 2013-10-24 2018-05-08 Hankkija Oy Use of tall oil fatty acid in binding toxins
US10799544B2 (en) 2013-11-13 2020-10-13 Hankkija Oy Feed supplement and a feed composition comprising resin acid based composition
IT202000018019A1 (it) 2020-07-24 2022-01-24 Marco Nogarole Procedimento di preparazione di addotti maleici con polipeptidi

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2188888A (en) * 1938-10-15 1940-01-30 Edwin T Clocker Condensation product and method
US2312731A (en) * 1938-10-19 1943-03-02 Standard Oil Dev Co Process and agent for breaking petroleum emulsions
US2950310A (en) * 1957-08-08 1960-08-23 Visco Products Co Surface active substances

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1023224B (de) * 1954-03-22 1958-01-23 Boehme Fettchemie Gmbh Verfahren zur Herstellung von wachsartigen Kondensationsprodukten

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2188888A (en) * 1938-10-15 1940-01-30 Edwin T Clocker Condensation product and method
US2312731A (en) * 1938-10-19 1943-03-02 Standard Oil Dev Co Process and agent for breaking petroleum emulsions
US2950310A (en) * 1957-08-08 1960-08-23 Visco Products Co Surface active substances

Cited By (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3300424A (en) * 1961-04-12 1967-01-24 Vianova Kunstharz Ag Process for the production of hardenable products by multiesterification
US3433754A (en) * 1964-04-13 1969-03-18 Vianova Kunstharz Ag Process for the production of synthetic resins hardenable by multiesterification
US3499007A (en) * 1964-12-05 1970-03-03 Cassella Farbwerke Mainkur Ag Addition products of maleic anhydride to polyalkylene ethers
US3624013A (en) * 1967-02-10 1971-11-30 Desoto Inc Heat-hardenable water-dispersible resins derived from polyhydric polyethers and mixtures thereof with benzoguanamine-formaldehyde condensates particularly adapted for electrodeposition
US3996054A (en) * 1971-09-24 1976-12-07 Minnesota Mining And Manufacturing Company Color photographic developing solution
US3981895A (en) * 1973-12-11 1976-09-21 Dulux Australia Ltd. Novel autoxidative derivatives of maleinized monocarboxylic fatty acid
US4028283A (en) * 1975-09-30 1977-06-07 Kao Soap Co., Ltd. Granular or powdery detergent composition
US4261851A (en) * 1979-07-23 1981-04-14 Johnson & Johnson Products, Inc. Low-irritating detergent composition
US4317740A (en) * 1980-04-22 1982-03-02 Union Camp Corporation Water-soluble polyesters
US7994106B2 (en) * 2006-05-09 2011-08-09 Arizona Chemical Company, Llc Water soluble rosin acid esters
US20080020957A1 (en) * 2006-05-09 2008-01-24 Nelson Lloyd A Water soluble rosin acid esters
US20080076822A1 (en) * 2006-09-27 2008-03-27 Miura Co., Ltd. Disinfectant
US20150164966A1 (en) * 2012-05-14 2015-06-18 Hankkija Oy Saponified tall oil fatty acid for use in treatment and animal feed supplements and compositions
US9789077B2 (en) 2012-05-14 2017-10-17 Hankkija Oy Use of saponified tall oil fatty acid
US9907771B2 (en) 2012-05-14 2018-03-06 Hankkija Oy Saponified tall oil fatty acid for use in treatment and animal feed supplements and compositions
US9789143B2 (en) 2013-05-14 2017-10-17 Hankkija Oy Use of tall oil fatty acid
US9919013B2 (en) 2013-05-14 2018-03-20 Hankkija Oy Use of tall oil fatty acid
US10092610B2 (en) 2013-05-14 2018-10-09 Hankkija Oy Tall oil fatty acid for use in treatment and animal feed supplements and compositions
US9962353B2 (en) 2013-10-24 2018-05-08 Hankkija Oy Use of tall oil fatty acid in binding toxins
US10799544B2 (en) 2013-11-13 2020-10-13 Hankkija Oy Feed supplement and a feed composition comprising resin acid based composition
US10849947B2 (en) 2013-11-13 2020-12-01 Hankkija Oy Feed supplement and a feed composition comprising resin acid based composition
US11253562B2 (en) 2013-11-13 2022-02-22 Forchem Oy Feed supplement
IT202000018019A1 (it) 2020-07-24 2022-01-24 Marco Nogarole Procedimento di preparazione di addotti maleici con polipeptidi

Also Published As

Publication number Publication date
SE308717B (en(2012)) 1969-02-24
DK104564C (da) 1966-06-06
DE1202002B (de) 1965-09-30
GB980730A (en) 1965-01-20
BE622310A (en(2012))

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