US3910972A - Fatty acid ester mixtures liquid at low temperatures and process - Google Patents

Fatty acid ester mixtures liquid at low temperatures and process Download PDF

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Publication number
US3910972A
US3910972A US446680A US44668074A US3910972A US 3910972 A US3910972 A US 3910972A US 446680 A US446680 A US 446680A US 44668074 A US44668074 A US 44668074A US 3910972 A US3910972 A US 3910972A
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fatty acid
fatty acids
per cent
liquid
weight
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US446680A
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Gerhard Dieckelmann
Helmut Hartmann
Jurgen Plapper
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Henkel AG and Co KGaA
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Henkel AG and Co KGaA
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Priority to US05/560,333 priority Critical patent/US3957426A/en
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C14—SKINS; HIDES; PELTS; LEATHER
    • C14C—CHEMICAL TREATMENT OF HIDES, SKINS OR LEATHER, e.g. TANNING, IMPREGNATING, FINISHING; APPARATUS THEREFOR; COMPOSITIONS FOR TANNING
    • C14C9/00—Impregnating leather for preserving, waterproofing, making resistant to heat or similar purposes
    • C14C9/02—Impregnating leather for preserving, waterproofing, making resistant to heat or similar purposes using fatty or oily materials, e.g. fat liquoring
    • 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
    • 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
    • C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils

Definitions

  • train oils are frequently not uniform in their composition; moreover, they may be partly split into fatty acids and contaminated by separations of salts.
  • the prior art therefore has already attempted to split train oils into the corresponding fatty acids and to manufacture from these, by re-esterification, uniform and qualitatively more valuable products. This process is cumbersome, however, and does not lead to satisfactory results.
  • the invention relates to a process for the manufacture of low-temperature resistant, liquid fatty acid esters, which can be used in particular in place of natural train oils or sperm oil in the preparation of fat liquoring agents in the leather industry.
  • low-temperature resistant, liquid fatty acid esters with a proportion of polyunsaturated fatty acids are characterized in that A. adducts of l to mols of ethylene oxide and/or propylene oxide to train-oil fatty acids or liquid fatty acid mixtures containing train-oil fatty acids with a content of 10 to 60 per cent by weight of polyunsaturated fatty acids of chain lengths C to C are esterified with liquid fatty acids or mixtures of fatty acids with a content of more than 75 per cent by weight of monoor di-unsaturated fatty acids of chain lengths C to C which are substantially free of any polyunsaturated train-oil fatty acids, or
  • B. adducts of l to 10 mols of ethylene oxide and/or propylene oxide on liquid fatty acids or mixtures of fatty acids with a content of more than 75 per cent by weight of monoor di-unsaturated fatty acids of chain lengths C to C which are substantially free of polyunsaturated train-oil fatty acids, are esterified with train-oil fatty acids or with mixtures containing train-oil fatty acids with a content of 10 to 60 per cent by weight of polyunsaturated fatty acids of chain lengths C to C
  • the invention also relates to the'manufacture of these liquid fatty acid esters and relates to partially or wholly sulfated products therefrom.
  • R CO is the acyl of at least one fatty acid selected from the group consisting of (a) train-oil fatty acids and (b) liquid fatty acid mixtures containing train-oil fatty acids and containing from 10 to 60 per cent by weight of polyunsaturated fatty acids having 20 to 24 carbon atoms
  • CO-R is the acyl of at least one liquid fatty acid substantially free of any polyunsaturated train-oil fatty acids, and having more than per cent by weight of unsaturated fatty acids selected from the group consisting of (i) monounsaturated fatty acids having 10 to 22 carbon atoms (ii) diunsaturated fatty acids having 10 to 22 carbon atoms, and (iii) mixtures thereof
  • R is a member selected from the group consisting of hydrogen and methyl
  • n is an integer from 1 to 10, with the proviso that up to 20 mol per cent of either R CO or COR can be
  • the present invention further provides a process for producing the above fatty acid esters liquid at low temperatures in which either (A) the fatty acid R COOH is adducted with 1 to 10 mols of the alkylene oxide and then esterified with the fatty acid R -COOH, or (B) the fatty acid R COOH is adducted with l to 10 mols of the alkylene oxide and ten esterified with the fatty acid R,COOH.
  • the present invention is further directed to a fatliquoring agent selected from the group consisting of (a) from O to per cent by weight of the aforesaid liquid fatty acid esters, (b) from 0 to 100 per cent by weight of the sulfation products of the aforesaid liquid fatty acid esters having a degree of sulfation of from 15 to 60 per cent, and (c) from O to 100 per cent by weight of the sulfonation products of the aforesaid liquid fatty acid esters having a degree of sulfonation of from 15 to 60 per cent, with the proviso that the total of (a), (b), and (c) is 100 per cent by weight.
  • a fatliquoring agent selected from the group consisting of (a) from O to per cent by weight of the aforesaid liquid fatty acid esters, (b) from 0 to 100 per cent by weight of the sulfation products of the aforesaid liquid fatty acid est
  • the present invention is also directed to a fatliquoring agent composition consisting essentially of (I) from 1 to 10 per cent by weight of the fat liquoring agent described above, (II) from 0 to 10 per cent by weight of a surfactant selected from the group consisting of an anionic surfactant, a nonionic surfactant, and the mixtures thereof, and (III) the balance to 100 per cent by weight of water.
  • the present invention moreover provides an improvement in the process for fat-liquoring of leather comprising contacting leather with a fat-liquoring agent and recovering said fat-liquored leather; the improvement which comprises contacting said leather with the above-described fat liquoring agent.
  • the starting material in case (A) above are train oil fatty acids, in particular fish-oil fatty acids, such as those obtained from herring oil menhaden oil or sardine oil.
  • train-oil fatty acids contain from 10 to 60 per cent by weight of polyunsaturated fatty acids having 20 to 24 carbon atoms, preferably having 20 to 22 carbon atoms. The number of double bonds in these fatty acids depends upon the origin of the train-oil; and there is on the average from 2.1 to 5.3 double bonds per fatty acid molecule.
  • the remaining fatty acids of the mixture comprises 40 to 90 per cent of a mixture comprising 65 to 100 per cent by weight of monounsaturated and/or polyunsaturated fatty acids having 14 to 18 carbon atoms, such as alkenoic acids having 14 to 18 carbon atoms, for example oleic acid, alkadienoic acids having 14 to 18 carbon atoms, for example linoleic acid, and alkatrienoic acids having 14 to 18 carbon atoms, for example linolenic acid; and this mixture further comprises to 35 per cent by weight of saturated fatty acids having ID to 22 carbon atoms, such as alkanoic acids having to 22 carbon atoms.
  • monounsaturated and/or polyunsaturated fatty acids having 14 to 18 carbon atoms such as alkenoic acids having 14 to 18 carbon atoms, for example oleic acid, alkadienoic acids having 14 to 18 carbon atoms, for example linoleic acid, and alkatrienoic acids having 14 to 18
  • the proportion of saturated fatty acids be as small as possible and should not exceed 35 per cent by weight of the total fatty acid con tent. If necessary the proportion of solid fatty acids can be reduced by distillation or other known refining methods.
  • train-oil fatty acids are reacted with l to 10 mols, preferably 2 to 4 mols, of ethylene oxide and/or propylene oxide per mol of fatty acid.
  • the addition takes place in a known manner in the presence of alkaline catalysts, preferably under pressure and at elevated temperatures.
  • the train-oil fatty acid alkylene oxide adducts are further esterified with liquid fatty acids or fatty acid mixtures which have more than 75 per cent and prefer ably more than 80 per cent, by weight, of unsaturated fatty acids selected from the group consisting of monounsaturated fatty acids having 10 to 22 carbon atoms and diunsaturated fatty acids having 10 to 22 carbon atoms, and the mixtures thereof, which contain substantially no polyunsaturated train-oil fatty acids.
  • Suitable examples of these unsaturated fatty acids include alkenoic acids having 10 to 22 carbon atoms, for example oleic acid, gadoleic acid and erucic acid, alkadienoic acids having 10 to 22 carbon atoms, for ex ample linoleic acid.
  • Preferred fatty acid mixtures having 10 to 22 carbon atoms are those with major amounts of oleic, linoleic, gadoleic and/or erucic acid, as are obtained from naturally occurring fats such as beef tallow, lard, peanut oil, palm-kernel oil, rape oil, tall oil, etc.
  • the saturated fatty acids portion may be separated from the liquid fatty acid by cold filtration, compressing, distillation or screening processes, whereby the residual amount of saturated fatty acids is less than 20 per cent by weight.
  • the esterification takes place according to known procedures in the presence of known catalysts, such as isopropyl titanate, stannous chloride, zinc dust, trisodium phosphate, tin powder or the like, preferably at elevated temperatures under vacuum, while distilling off the water formed in the reaction.
  • catalysts such as isopropyl titanate, stannous chloride, zinc dust, trisodium phosphate, tin powder or the like, preferably at elevated temperatures under vacuum, while distilling off the water formed in the reaction.
  • the molar ratios of the components range approximately from 0.8 l to 1.2 1, preferably about 1 1, so that an esterification product results with an Ol-l-value of below 30.
  • uniformly structured fatty acid di-esters of polyoxyalkylene glycols having 2 and/or 3 carbon atoms are produced and are characterized in that they contain different fatty acid components within one molecule. They are thus distinguished in a characteristic manner from those polyoxyalkylene glycol fatty acid esters which are obtained by esterification of 1 mol of a polyoxyalkylene glycol with 2 mols of a mixture of corresponding fatty acids.
  • Such mixed esters which contain the fatty acid residue in statistical distribution have different, and for many applications less advantageous, properties.
  • ester mixtures of the present invention are clear yellowish to brown oils which have good resistance to low temperatures.
  • fat-liquoring agents for leather or skins can take place in an organic solvent, such as benzine, or chlorinated hydrocarbons, or as an aqueous emulsion with the addition of anionic or nonionic surfactants.
  • anionic surfactants are sulfates for example higher fatty alcohol sulfates or fatty alcohol polyalkylene oxide ether sulfates.
  • nonionic surfactants are ethylene oxide adducts or higher fatty alcohols, alkyl phenols, fatty amines, or fatty acid ethanolamides, which contain sufficient ethoxide units to be water soluble.
  • the esterification products of the present invention may also be used in partially sulfated or sulfited form, for which purpose they are reacted in a known manner with technical sulfuric acid, oleum or with an air bisulfite mixture.
  • the degree of sulfation or sulfonation ranges from about 15 to 60 per cent of the available double bonds in the ester.
  • the sulfonated esters can be used with emulsifiers or can be emulsified in water without further use of surfactants and utilized in this form for the fat-liquoring of leather and/or skins.
  • Suitable for use as fat-liquoring agents include (a) from O to per cent by weight of the liquid fatty acid esters themselves, (b) from to 100 per cent by weight of the sulfation products of these esters having a 'degree of sulfation of from 15 to 60 per cent,'and (c) from 0 to 100 per cent by weight of the sulfonation products of these esters having a degree of sulfonation of from 15 to 60 per cent, with the proviso that the total of (a), (b) and (c) is 100 per cent. 7
  • Suitable fat-liquoring agent compositions include (I) from 1 to lO per cent by weight, preferably from 5 to 8 per cent by weight, of the above-described "fat-' liquoring agent, said fat-liquoring agent preferably comprising from 70 to 100 per cent by'jweight' of one of the ester sulfonation product orthe ester sulfation product and from 0 to 30 per cent by weight of the ester itself; (11) from 0 to per cent-by weight of an anionic surfactant or a nonionic surfactant and (III) the balance to 100 per cent by weight'of water.
  • the leathers fat-liquored with the products in accordance with the invention have a pleasant, oily handle and are of a relatively light color.
  • the products of the invention thus surpass in their qualitya'n'dproperties the naturally occurring train-oil and th'e train-bil re ⁇ fined products, and correspond largely to sperm oil for which they represent an eminently suitable substitute.
  • the products can also be used'adv'antageously as greasing and lubricating agents in other fields, e.g. as lubricants for textile fibers or for the achievement of special lubricating effects on metal surfaces.
  • t I i EXAMPLE 1 A mixture consisting of 2800 gm of the liquid portion of tallow fatty acids (technicaloleic acidjacid value: 202; saponification value: 205; iodine value: 92) and 4130 gm of an addition product of 3 mols of ethylene oxide to one mol of fish-oil fatty acid (acid value: 0.9, saponification value: 121; iodine value: 73; OH 'value: 142) was heated with 7 gm of isopropyl titanate, with stirring, in a roundbottomed'flask, fitted with a distillation column, during a period of 8 hours from 140 up to 235C under vacuum, with the vacuum 'being reduced with rising temperature from 100 mm to 30 mm Hg.
  • EXAMPLE 2 500 gm of a mixture of talloleic acid and the fatty acid distillate from rape oil in a molar ratio of 1:1 (acid value: 192; saponification value: 195 iodine value 115; resinic acid 0.6%), and 600 gm of an addition product of 2 mols of ethylene oxide on the fatty acid distillate from menhaden oil (acid value: 0.3; saponification value: 155; iodine value: 153; OH value: 161) were esterified in the presence of 2 gm of tin powder.
  • the reaction was conducted at a vacuum pressure of 4 mm Hg and at a reaction temperature which was increased from 100 up to 200C during a period of 6 hours.
  • iodine valtiej94; turbidityjpoint: 65C) were esterified with 395 gmbf anaddition product of 2 mols of propyabout '25 per cent.
  • EXAMPLE 4 A mixture of the liquid esters prepared according to Example'l was sulfited in a known manner at 70C to C with 14 percent by weight of sodium hydrogen sulfite'by injecting air into the liquid, until the product was emulsifiable in water.
  • the degree of sulfitation was Chrome-tanned suede leather for clothing, retanned in the usual manner with synthetic tanning agents, was fatliquored in the usual manner at 60C for 45 minutes with a fat-liquoring agent composition containing 6 to 8percent of a mixture consisting of 95 per cent of the above sulfited product, and 5 per cent of an adduct of 8 mols ethylene oxide on a mixture of fatty alcohols having 12 to 18 carbon atoms. The balance to per cent by weight was waterl The leather was contacted with 100 per cent liquor, and then dried and finished. A cloth-like soft, full, clothing leather of good handle was obtained. I
  • Chrome-tanned upper leathers, retanned with vegetable tanning agents were fat-liquored at 50 to 60C for 45 minutes with a fat-liquoring agent composition .containing from 5 to 6 per centof a fat-liquoring agent mixture containing 70 .per cent of the sulfated ester product and 30 per cent of the corresponding nonsulfated ester.
  • the balance to 100 per cent by weight was water.
  • the leather was contacted with 100 per cent liquor, dried in the known manner and finished. A full, soft upper leather with good handle was obtained.
  • EXAMPLE 6 per cent by weight was water.
  • the leather was contacted with 100 per cent liquor, dried and finished. A full, soft upper leather of good handle was obtained.
  • EXAMPLE 7 Utilizing a procedure analogous to that described in Example 1, 560 gm of a fish-oil distillation fatty acid (acid value 197; saponification value: 200; iodine value: 140 were esterified with 850 gm of an addition product of 3 mols of propylene oxide on one mol of the liquid constituents of a peanut oil distillation fatty acid (acid value: saponification value: 120; iodine value: 59; OH value: 131 in the presence of4 gm of stannous chloride.
  • Fatty acid esters liquid at low temperature having the formula wherein R, CO is the acyl of at least one fatty acid selected from the group consisting of (a) train-oil fatty acids and (b) liquid fatty acid mixtures containing trainoil fatty acids and containing from to 60 per cent by weight of polyunsaturated fatty acids having 20 to 24 carbon atoms
  • CO-R is the acyl of at least one liquid fatty acid substantially free of any polyunsaturated train-oil fatty acids and having more than 75 per cent by weight of unsaturated fatty acids selected from the group consisting of (i) monounsaturated fatty acids having 10 to 22 carbon atoms (ii) diunsaturated fatty acids having 10 to 22 carbon atoms, and (iii) mixtures thereof
  • R is a member selected from the group consisting of hydrogen and methyl
  • n is an integer from 1 to 10, with the proviso that up to 20 mol percent of either R,--CO or COR can be replaced by hydrogenv
  • liquid fatty acid esters of claim 1 in which the fatty acids of the acyl R -CO contain on an average from 2.1 to 5.3 double bonds per fatty acid molecule.
  • the R CO of (b) is the acyl of fatty acid mixtures consisting essentially of (j) from 10 to 60 per cent by weight of polyunsaturated fatty acids having 20 to 24 carbon atoms and (jj) from 40 to per cent by weight of fatty acids consisting essentially of (aa) from
  • liquid fatty acid esters of claim 4 in which said fatty acid mixtures of (j) consist of from 10 to 60 per cent by weight of polyunsaturated fatty acids having 20 to 22 carbon atoms.
  • liquid fatty acid esters of claim 1 in which CO-R is the acyl of at least one liquid fatty acid containing a major amount of an unsaturated fatty acid selected from the group consisting of oleic acid, linoleic acid, gadoleic acid, erucic acid and the mixtures thereof.
  • liquid fatty acid esters of claim 1 in which the molar ratio of said R CO to COR is approximately 1:1.
  • liquid fatty acid esters of claim 1 in which said R -CO is the acyl of at least one fatty acid obtained from a fish-oil selected from the group consisting of herring oil, menhaden oil and sardine oil.

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  • Chemical & Material Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Treatment And Processing Of Natural Fur Or Leather (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Fats And Perfumes (AREA)
  • Lubricants (AREA)
US446680A 1973-03-08 1974-02-28 Fatty acid ester mixtures liquid at low temperatures and process Expired - Lifetime US3910972A (en)

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US05/560,333 US3957426A (en) 1973-03-08 1975-03-21 Fatty acid ester mixtures liquid at low temperatures and process

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DE2311344A DE2311344C2 (de) 1973-03-08 1973-03-08 Kältebeständige, flüssige Fettsäureestergemische

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US (1) US3910972A (https=)
JP (1) JPS6011078B2 (https=)
BR (1) BR7401696D0 (https=)
DE (1) DE2311344C2 (https=)
ES (1) ES424022A1 (https=)
FR (1) FR2220510B1 (https=)
GB (1) GB1441045A (https=)
IT (1) IT1003694B (https=)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4470825A (en) * 1982-10-15 1984-09-11 Schill & Seilacher Gmbh & Co. Process for the fat-liquoring of leathers and skins
US4681900A (en) * 1984-01-13 1987-07-21 Kao Corporation Biocide activator

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS58127800A (ja) * 1982-01-23 1983-07-29 川澄　一雄 皮革の物性改良法
DE3617657C2 (de) * 1986-05-26 1994-08-18 Stockhausen Chem Fab Gmbh Bei Raumtemperatur flüssige Derivate von natürlichen Fetten oder Ölen, Verfahren zu deren Herstellung, und ihre Verwendung
DE4216187C2 (de) * 1992-02-21 2002-06-06 Ollert Uwe Verwendung einer wässrigen Lösung aus Wasser, aus wenigstens einer Waschsubstanz, als Lederwaschmittel

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1970578A (en) * 1930-11-29 1934-08-21 Ig Farbenindustrie Ag Assistants for the textile and related industries
US2131142A (en) * 1932-03-02 1938-09-27 Gen Aniline Works Inc Addition products of glycide
US2298186A (en) * 1939-10-25 1942-10-06 Du Pont Ester
US2305228A (en) * 1940-05-14 1942-12-15 Du Pont Hydraulic fluid

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1970578A (en) * 1930-11-29 1934-08-21 Ig Farbenindustrie Ag Assistants for the textile and related industries
US2131142A (en) * 1932-03-02 1938-09-27 Gen Aniline Works Inc Addition products of glycide
US2298186A (en) * 1939-10-25 1942-10-06 Du Pont Ester
US2305228A (en) * 1940-05-14 1942-12-15 Du Pont Hydraulic fluid

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4470825A (en) * 1982-10-15 1984-09-11 Schill & Seilacher Gmbh & Co. Process for the fat-liquoring of leathers and skins
US4681900A (en) * 1984-01-13 1987-07-21 Kao Corporation Biocide activator

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FR2220510B1 (https=) 1977-09-16
ES424022A1 (es) 1976-05-16
GB1441045A (en) 1976-06-30
BR7401696D0 (pt) 1974-11-05
DE2311344C2 (de) 1982-04-08
DE2311344A1 (de) 1974-09-12
FR2220510A1 (https=) 1974-10-04
JPS49120904A (https=) 1974-11-19
JPS6011078B2 (ja) 1985-03-22
IT1003694B (it) 1976-06-10

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