US2681283A - Stabilized fatty compositions and stabilizers therefor - Google Patents

Stabilized fatty compositions and stabilizers therefor Download PDF

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Publication number
US2681283A
US2681283A US266594A US26659452A US2681283A US 2681283 A US2681283 A US 2681283A US 266594 A US266594 A US 266594A US 26659452 A US26659452 A US 26659452A US 2681283 A US2681283 A US 2681283A
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fatty
glycine
phosphoric acid
compositions
solution
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US266594A
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Noel H Kuhrt
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Eastman Kodak Co
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Eastman Kodak Co
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    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B5/00—Preserving by using additives, e.g. anti-oxidants
    • C11B5/0092—Mixtures

Definitions

  • This invention relates to fatty compositions characterized by improved stability against oxidation and to stabilizer compositions useful as additives-tofattymaterials.
  • the susceptibility 0f fatty materials to oxidation and resultant rancidity makes :it necessary to stabilize fatty materials :normally .subject to oxidation, and particularly edible fats and oils, before commercial use.
  • the fatty-materialasubject to the deleterious effects of oxidation are usually characterized by the presence of ⁇ unsaturated components, :and such fatty :materials include solid fats, "fatty oils :and .ifateforming fatty acids.
  • the fatty materials used most widely in edible products are those materials consisting predominantly of fatty triglycerides as typified by the animal fats and vegetable oils, whether unhydrogenated .or partially hydrogenated, and such material must, of course, be stabilized against peroxide formation and resultant :,oxidativerancidity.
  • It is. another object, of the invention to provide new stabilizer :compositions especially effective for incorporation in fatty :smaterials normally subject to oxidation.
  • Another object of the invention is to stabilize edible fatty materials, such as are commonly used for human consumption, against ,objectionable development of oxidative vrancidity under normal storageconditions.
  • Another object of the invention is :to ;provide improved animal fat and vegctableoil compositions,. and particularly shortening-compositions.
  • Another object 'of the invention is to .provide fatty compositions effectively stabilized against excessive oxidation but retaining their desirable physical and chemical characteristics.
  • this invention which :comprises .stabilizing fatty material normally "subject tooxidation by incorporating itherein -a solution of glycine and phosphoric acid in a fpolyalkylene oxide derivative of a fatty acid partial-esterrofa polyhydric alcohol or an anhydride of such ralcohol.
  • the invention is [applicable for stabilizing any of .the :well -known .”
  • fattymaterials normally sub- 2 ject to oxidation, including both .solid fats and fatty oils, and particularly the fatty materials consisting predominantly of fatty'triglycerides or fag-formin fatty acids normally subject to oxida ion.
  • the fatty acids includeany of "the pure or mixedunsaturated fatty acids as typified by oleic and linoleic acids.
  • polyalkylene oxide polymer with a fatty acid partial ester of a polyhydric alcohol or anhydride.
  • the polyoxyalkylene derivatives employed are preferably those having a melting point not higher than 100 C., and desirably those obtained by reacting from about 5 to moles, or more desirably about 16 to 25 moles, with a fatty acid 1110110851761 of The ycine andrhos hq acid dissolved in the polyoxyethylene derivative either with such derivative in li'quidform or by use 'of a suitable mutual solvent such s glycerin e.
  • soy protein hydrolysate can be employed to furnish the desired glycine, and a suitable salt of phosphoric acid can be employed, such as sod um phosphate, to furnish the phosphoric acid within the scope of this invention.
  • a suitable salt of phosphoric acid can be employed, such as sod um phosphate, to furnish the phosphoric acid within the scope of this invention.
  • the glycine and phosphoric acid are desirably employed with the phosphoric acid present in an amount not greater than twice the weight of glycine, and are preferably employed in approximately equal amounts by weight although larger proportions of glycine are not particularly objectionable and can be employed if desired.
  • the solution of glycine and phosphoric acid in the polyoxyethylene sorbitan monoester or similar derivative is readily incorporated in the fatty material to be stabilized, preferably at a temperature at which both the fatty material and the stabilizer composition are liquid, and desirably at a temperature of 50-95 C. Higher temperatures are usually not necessary and are undesirable. from the standpoint of obtaining optimum stability. Effective stabilization is obtained with amounts of the glycine and phosphoric acid each of from 0.00005% to 0.02% by weight based on the total composition weight although higher amounts such as 0.1% or even 0.5% or higher of each of the glycine and phosphoric acid can be used if desired.
  • the amount of polyoxyethylene derivative in the fatty composition is desirably kept below about 5% of the total composition weight but the amount of such derivative can be. varied by varying the concentration of glycine and phosphoric acid in solution in the derivative; In the preferred compositions embodying the invention, the compositions comprise at least 85% by weight of fatty triglycerides.
  • compositions prepared in accordance with this invention were evaluated for stability by the Active Oxygen Method (AOM) wherein the peroxide content in millimols per kilogram of fat was checked at periodic intervals while a sample of the composition was heated at 95 C. with air bubbling through the sample.
  • a peroxide value of 20 imum' permissible value for commercial compositions, and the stabilized compositions embodying this invention were tested to determine their stability in terms of the time necessary to reach a peroxide value of 20 under the accelerated test'conditions as compared to the time required for an unstabilized control sample.
  • Example 1 A solution of 0.02% by weight of glycine and 0.02% by weight of phosphoric acid in polyoxyethylene sorbitan monolaurate, obtained by reacting 20 moles of ethylene oxide with 1 mole of sorbitan monolaurate, was mixed with partially hydrogenated cottonseed oil shortening at a temperature of 60 0., the stabilizer solution amounting to 1.5% by the weight of such shortening.
  • the AOM stability of the resulting stabilized composition based on the time necessary to reach a peroxide value of 20, was found to have increased about 40% over that of the control sample.
  • Example 4 to give a composition containing 0.0003% by weight of glycine, 0.0003% by weight of phosphoric acid, and 1.5% by weight of polyoxyethylene sorbitan monooleate in which the polyoxyethylene amounted to 20 molar proportions. .
  • the resulting stabilized lard by the AOM test reached a peroxide value of 20 after 20 hours as compared to 7 hours for a control sample of the same lard base.
  • Example 3 Example 4 Lard stabilized with 1.5% by weight of a soluphosporic acid in polyoxyethylenezo sorbitan monolaurate showed an increase in by the AOM test. 7
  • a fatty composition consisting predomi nantly of fatty material normally subject to oxidation and having admixed therewith a solution of glycine and phosphoric acid in a polyalkylene oxide derivative of a fatty acid partial ester of a compound selected from the class consisting of polyhydric alcohols and their anhydrides.
  • a normally solid fat having incorporated therein a solution of glycine and phosphoric acid in a polyoxyethylene derivative ofv a fatty acid partial ester of a hexitan.
  • a fatty oil having incorporated therein a solution of glycine and phosphoric acid in a polyoxyethylene derivative of a fatty acid partial ester of a hexitan.
  • a fatty composition consisting predominantly of fatty acid triglycerides and having dis-- persed therein a minor amount of a solution of glycine and phosphoric acid in a polyoxyethylene derivative of a fatty acid monoester of sorbitan.
  • phosphoric acid all based on the total composition weight, said glycine and phosphoric. acid being present in solution in a polyoxyethylene derivative of a fatty acid monoester of sorbitan.
  • a shortening having incorporated therein a solution of glycine and phosphoric acid in a poly-.
  • a stabilizer composition for stabilizing fatty material comprising a solution of glycine and phosphoric acid in a polyalkylene oxide derivative of a fatty acid partial ester of a compound selected from the class consisting of polyhydric alcohols and their anhydrides.
  • a stabilizer for fatty material comprising a solution of glycine and phosphoric acid in a polyoxyethylene derivative of a fatty acid monoester of sorbitan.
  • a stabilizer for fatty material comprising a solution of glycine and phosphoric acid in a References Cited in the file of this patent UNITED STATES PATENTS Number Name Date 2,511,804 Hall June 13, 1950 2,535,910 Fonyo Dec. 26, 1950 OTHER REFERENCES Chem. Abst. 40 (1946), 479

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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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

Patented June I 1954 STABILIZED FATTY :STABILIZER Noel fl. Kuhrt, Rochester, N.
s THEREFOR Y., assignor'to Eastman Kodak Company, Rochester, 'N. Y., 'a cor-. .porationzoffNewJersey No'Drawing. .Applicationr-January 15, 1952,
:Scrial No. 266594 .101Claiims. .1
This invention relates to fatty compositions characterized by improved stability against oxidation and to stabilizer compositions useful as additives-tofattymaterials.
The susceptibility 0f fatty materials to oxidation and resultant rancidity makes :it necessary to stabilize fatty materials :normally .subject to oxidation, and particularly edible fats and oils, before commercial use. Thefatty-materialasubject to the deleterious effects of oxidation are usually characterized by the presence of \unsaturated components, :and such fatty :materials include solid fats, "fatty oils :and .ifateforming fatty acids. The fatty materials used most widely in edible products are those materials consisting predominantly of fatty triglycerides as typified by the animal fats and vegetable oils, whether unhydrogenated .or partially hydrogenated, and such material must, of course, be stabilized against peroxide formation and resultant :,oxidativerancidity.
It ,is accordingly an object of this invention to provide new :fatty compositions characterized .by improved stability'against de'leteriousoxidation.
It is. another object, of the invention :to provide new stabilizer :compositions especially effective for incorporation in fatty :smaterials normally subject to oxidation.
It is a further object ;of the invention to :provide new stabilized composition consisting predominantly of fatty triglycerides.
Another object of the invention is to stabilize edible fatty materials, such as are commonly used for human consumption, against ,objectionable development of oxidative vrancidity under normal storageconditions.
Another object of the invention is :to ;provide improved animal fat and vegctableoil compositions,. and particularly shortening-compositions.
Another object 'of the invention is to .provide fatty compositions effectively stabilized against excessive oxidation but retaining their desirable physical and chemical characteristics.
:Other objects will be apparent :fromwthe .descriptionand claims which'follow.
These and other objects are attained in accordance with :this invention which :comprises .stabilizing fatty material normally "subject tooxidation by incorporating itherein -a solution of glycine and phosphoric acid in a fpolyalkylene oxide derivative of a fatty acid partial-esterrofa polyhydric alcohol or an anhydride of such ralcohol.
The invention is [applicable for stabilizing any of .the :well -known ."fattymaterials :normally sub- 2 ject to oxidation, including both .solid fats and fatty oils, and particularly the fatty materials consisting predominantly of fatty'triglycerides or fag-formin fatty acids normally subject to oxida ion.
the usual vegetable oil shortenings.
The fatty acids includeany of "the pure or mixedunsaturated fatty acids as typified by oleic and linoleic acids.
'ene ox1de, or a polyalkylene oxide polymer With a fatty acid partial ester of a polyhydric alcohol or anhydride. The polyoxyalkylene derivatives employed are preferably those having a melting point not higher than 100 C., and desirably those obtained by reacting from about 5 to moles, or more desirably about 16 to 25 moles, with a fatty acid 1110110851761 of The ycine andrhos hq acid dissolved in the polyoxyethylene derivative either with such derivative in li'quidform or by use 'of a suitable mutual solvent such s glycerin e.
soy protein hydrolysate can be employed to furnish the desired glycine, and a suitable salt of phosphoric acid can be employed, such as sod um phosphate, to furnish the phosphoric acid within the scope of this invention. The glycine and phosphoric acid are desirably employed with the phosphoric acid present in an amount not greater than twice the weight of glycine, and are preferably employed in approximately equal amounts by weight although larger proportions of glycine are not particularly objectionable and can be employed if desired.
The solution of glycine and phosphoric acid in the polyoxyethylene sorbitan monoester or similar derivative is readily incorporated in the fatty material to be stabilized, preferably at a temperature at which both the fatty material and the stabilizer composition are liquid, and desirably at a temperature of 50-95 C. Higher temperatures are usually not necessary and are undesirable. from the standpoint of obtaining optimum stability. Effective stabilization is obtained with amounts of the glycine and phosphoric acid each of from 0.00005% to 0.02% by weight based on the total composition weight although higher amounts such as 0.1% or even 0.5% or higher of each of the glycine and phosphoric acid can be used if desired. The amount of polyoxyethylene derivative in the fatty composition is desirably kept below about 5% of the total composition weight but the amount of such derivative can be. varied by varying the concentration of glycine and phosphoric acid in solution in the derivative; In the preferred compositions embodying the invention, the compositions comprise at least 85% by weight of fatty triglycerides.
The compositions prepared in accordance with this invention were evaluated for stability by the Active Oxygen Method (AOM) wherein the peroxide content in millimols per kilogram of fat was checked at periodic intervals while a sample of the composition was heated at 95 C. with air bubbling through the sample. A peroxide value of 20 imum' permissible value for commercial compositions, and the stabilized compositions embodying this invention were tested to determine their stability in terms of the time necessary to reach a peroxide value of 20 under the accelerated test'conditions as compared to the time required for an unstabilized control sample.
The invention is illustrated by the following examples 'of certain preferred embodiments which are included only for purposes of illustration and which are not intended to limit the scope of the invention unless otherwise specifically indicated.
Example 1 A solution of 0.02% by weight of glycine and 0.02% by weight of phosphoric acid in polyoxyethylene sorbitan monolaurate, obtained by reacting 20 moles of ethylene oxide with 1 mole of sorbitan monolaurate, was mixed with partially hydrogenated cottonseed oil shortening at a temperature of 60 0., the stabilizer solution amounting to 1.5% by the weight of such shortening. The AOM stability of the resulting stabilized composition, based on the time necessary to reach a peroxide value of 20, was found to have increased about 40% over that of the control sample.
Example 2 Lard was stabilized in accordance with this was considered to be the maxtion of 0.02% glycine and 0.02%
4 invention to give a composition containing 0.0003% by weight of glycine, 0.0003% by weight of phosphoric acid, and 1.5% by weight of polyoxyethylene sorbitan monooleate in which the polyoxyethylene amounted to 20 molar proportions. .The resulting stabilized lard by the AOM test reached a peroxide value of 20 after 20 hours as compared to 7 hours for a control sample of the same lard base. Example 3 Example 4 Lard stabilized with 1.5% by weight of a soluphosporic acid in polyoxyethylenezo sorbitan monolaurate showed an increase in by the AOM test. 7
Similarly improved results are obtained with other stabilized compositions embodying this invention; and although the invention has been described in considerable detail with reference to certain preferred embodiments, it will be understood that variations and modifications can be effected within the spirit and scope of the invention as described hereinabove and as defined in the appended claims.
I claim:
1. A fatty composition consisting predomi nantly of fatty material normally subject to oxidation and having admixed therewith a solution of glycine and phosphoric acid in a polyalkylene oxide derivative of a fatty acid partial ester of a compound selected from the class consisting of polyhydric alcohols and their anhydrides.
2. A normally solid fat having incorporated therein a solution of glycine and phosphoric acid in a polyoxyethylene derivative ofv a fatty acid partial ester of a hexitan.
3. A fatty oil having incorporated therein a solution of glycine and phosphoric acid in a polyoxyethylene derivative of a fatty acid partial ester of a hexitan. V
4. A fatty composition consisting predominantly of fatty acid triglycerides and having dis-- persed therein a minor amount of a solution of glycine and phosphoric acid in a polyoxyethylene derivative of a fatty acid monoester of sorbitan.
to 0.02% by weight of phosphoric acid, all based on the total composition weight, said glycine and phosphoric. acid being present in solution in a polyoxyethylene derivative of a fatty acid monoester of sorbitan.
7. A shortening having incorporated therein a solution of glycine and phosphoric acid in a poly-.
stability of about oxyethylene derivative of a higher fatty acid monoester of sorbitan.
8. A stabilizer composition for stabilizing fatty material comprising a solution of glycine and phosphoric acid in a polyalkylene oxide derivative of a fatty acid partial ester of a compound selected from the class consisting of polyhydric alcohols and their anhydrides.
9. A stabilizer for fatty material comprising a solution of glycine and phosphoric acid in a polyoxyethylene derivative of a fatty acid monoester of sorbitan.
10. A stabilizer for fatty material comprising a solution of glycine and phosphoric acid in a References Cited in the file of this patent UNITED STATES PATENTS Number Name Date 2,511,804 Hall June 13, 1950 2,535,910 Fonyo Dec. 26, 1950 OTHER REFERENCES Chem. Abst. 40 (1946), 479

Claims (1)

1. A FATTY COMPOSITION CONSISTING PREDOMINANTLY OF FATTY MATERIAL NORMALLY SUBJECT TO OXIDATION AND HAVING ADMIXED THEREWITH A SOLUTION OF GLYCINE AND PHOSPHORIC ACID IN A POLYALKYLENE OXIDE DERIVATIVE OF A FATTY ACID PARTIAL ESTER OF A COMPOUND SELECTED FROM THE CLASS CONSISTING OF POLYHYDRIC ALCOHOLS AND THEIR ANHYDRIDES.
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3355302A (en) * 1964-01-24 1967-11-28 Procter & Gamble Anti-spattering plastic shortening

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2511804A (en) * 1950-06-13 Antioxidant salt
US2535910A (en) * 1947-09-24 1950-12-26 Wm J Stange Co Treatment of unrendered fat with nordihydroguaiaretic acid

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2511804A (en) * 1950-06-13 Antioxidant salt
US2535910A (en) * 1947-09-24 1950-12-26 Wm J Stange Co Treatment of unrendered fat with nordihydroguaiaretic acid

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3355302A (en) * 1964-01-24 1967-11-28 Procter & Gamble Anti-spattering plastic shortening

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