US2794796A - ouucg - Google Patents

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US2794796A
US2794796A US2794796DA US2794796A US 2794796 A US2794796 A US 2794796A US 2794796D A US2794796D A US 2794796DA US 2794796 A US2794796 A US 2794796A
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/42—Proteins; Polypeptides; Degradation products thereof; Derivatives thereof, e.g. albumin, gelatin or zein

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  • Amobject-of-this-invention is the provision of a proccas ier; preparing a purified lipoprotein. Another object is,the ,proyi si on of'a process for separating soap and salt contaminantsr' of lipoprotein products. Other objects and, adyantages 10f thisinvention will become apparent as the specification proceeds.
  • a lipoprotein substance obtained; by reacting a proteinaceous substance and a fatty-acid halide in an alkaline mediiun and dehydrating the resulting reaction product,.-may be purified by a process 3 which involves mixing such lipoprotein with an organicfatsolvent having a specific gravity higher than that of-the-lipopnotein.'
  • the mixture of this organic fat solventand the lipoprotein substance should be achieved in a substantially anhydrous system, and the lipoprotein substance should be maintained at an acidic reaction in such solvent' mixture.
  • the acidification of the lipoprotein substance converts the soap contaminant thereof to the free fatty acid, and results in the formation of a salt therein.
  • the lipoprotein substance employed in this purification pnocedure may be prepared by reacting any proteinaceous substance With any fatty acid halide.
  • proteinaceous substance employed herein means derived proteins such as proteoses, polypeptides and peptones, as well as whole pr0t eins.-
  • this fatty acid halide reactant-contains from '1 to 22 carbon atoms, and espengout this Sclrotten-Baumann procedure, a portion 'ofthe fatty acid' halide reacts with the alkali:
  • fatty acid halides containing from 12 to 18 carbon atoms.
  • this fatty acid halide reactant can. be derived from a mixture of fatty acids, such as are prepared from tallow and soya bean.
  • suitable fatty acid halides for use in preparing this lipoprotein substance I mention, for example, the halide derivatives of such fatty acids as oleic, palmitic, lauric, capric, stearic, etc.
  • the halide component of this fatty acid halide reactant may be bromine, fluorine, chlorine, etc. but better purification of the lipoprotein substance can be achieved when it is derived from a fatty acid chloride reactant.
  • the proteinaceous substance and the fatty acid halide may be reacted in an alkaline medium to form a lipoprotein reaction product.
  • the reaction mixture should include an alkali having a cation capable of reacting with the anion of an acid to form a salt.
  • an alkali having an alkali metal cation e. g. sodium, potassium, etc.
  • the l-ipoprotein reaction product should be dehydrated while being maintained at a substantially neutral or alkaline pH. I have found that the acidification of such reaction product prior to drying apparently increases the melting point and viscosity thereof such that it is difficult to obtain the lipoprotein substance in a substantially anhydrous form.
  • the reaction product is maintained at a pH of at least pH 6.5 during this drying step, and especially desirable dehydration is obtained when the reaction product has a pH of at least pH 7.5.
  • drying of this lipoprotein reaction product may be ob tained by such methods as evaporation, lyophilization,
  • the dehydrated lipoprotein substance may contain such;
  • the dehydrated lipdprotein substance may be pulverized'to produce greater exposure of the contaminants therein to' the acidifying agent and to the organic fat solvent.
  • the lipoprotein substance into a suitable vessel, and then charging into the vessel the organic fat solvent.
  • The. mixing of the lipoprotein substanceand the fat solvent may be achieved by pumping, stirring, churning, etc.
  • the acidification of the lipoprotein substance may be obtained by contacting this solventmixture with an anhydrous acid which is dispersible in such solvent mixture.
  • anhydrous acid which is dispersible in such solvent mixture.
  • dispersible I mean that the anhydrous acid should be either soluble in the organic fat solvent or in the gaseous state such that it may be bubbled through the solvent mixture.
  • substantially all of the soap contaminant of the lipoprotein substance may be converted to the free fatty acid by infusing into the solvent mixture acid in such amount as to adjust the pH of the lipoprptein substance to less than about pH 5.5.
  • acids suitable for mixing with the solvent mixture to obtain conversion of the soap contaminant to the free. fatty acid I mention, for example, mineral acid anhydrides, e. g. hydrochloric, sulfuric, sulfurous and phos phoric, and organic acids, e. g. oxalic. r
  • the pulverizing of this lipoprotein substance may be obtained by a method such as cornthe other hand, the specific gravity of this organic fatsolvent should be less than that of the inorganic salt. Consequently, the specific gravity of such solvent may be less than about 1.9 to 2.7.
  • suitable organic fat solvents together with their specific gravities, as: chloroform 1.498, carbontetrachloride 1.595, trichlorethylene 1.456, dioxane 1.034, chlorobenzene 1.107, and ethylene dichloride 1.257.
  • the ratio of organic fat solvent to lipoprotein substance included in this solvent mixture may be increased in accordance with an increased concentration of contaminant substances contained in such lipoprotein substance.
  • the dehydrated lipoprotein product generally contains not more than 40% by weight of such contaminant substances, and more often the concentration of contaminants therein is less than 25% by weight.
  • the concentration of these contaminants in the lipoprotein product is less than about butinmore efiicient operation it may be possible to obtain a concentration of contaminants therein of about 3 to 6%. Consequently, in the usual practice a ratio of fat solvent to lipoprotein substance of at least about 2 is suitable for carrying out this purification, and for practical considerations a ratio of fat solvent to lipoprotein substance of less than about 10 is convenient.
  • the resulting solvent mixture may be settled to obtain an equilibrium state therein, and to provide the heterogeneous solvent system.
  • the contaminant free fatty acid dissolves inthe organic fat solvent forming a layer subjacent to the lipoprotein phase and superimposed upon a salt phase.
  • the lipoprotein phase may be separated from the other phases by draining, skimming, etc.
  • the subnatant organic solvent and salt phases can be drained from the bottom of the mixing vessel, and the residual lipoprotein recovered from the bottom of the vessel.
  • the latter separation method involves skimming the lipoprotein layer from the top of the mixing vessel.
  • the residual organic fat solvent may be removed from the separated lipoprotein by evaporation, etc. i
  • Example I The skimmed lipoprotein layer was dried by evaporation.
  • This dry product was analyzed and found to contain 96% of lipoprotein and 4% of sodium chloride.
  • the subnatant salt layer was also separated from the purification mixture, and upon analysis was found to contain 85% of sodium chloride.
  • Example II A lipoprotein product, obtained by reacting gelatin with 4 a fatty acid chloride was prepared. This lipoprotein product, had a pH of 53, and its composition was as follows:
  • This lipoprotein product in the amount of 10 gm., was suspended in cc. of trichloroethylene and the resulting mixture was settled to form three phases. The supernatant lipoprotein phase was separated by skimming, and the skimmed lipoprotein dried by evaporation. The dry product was analyzed and found to have the following composition:
  • Example III A reaction product of lard flake fatty acid chlorides and gelatin was prepared. This lipoprotein product had a pH of 7.7, and the following composition:
  • This lipoprotein product in the amount of 100 gm., was suspended in 3000 cc. of ethylene dichloride. Gaseous hydrochloric acid was added to this suspension until a pH of 4.7-5.0 was obtained. After settling, the supernatant solvent and lipoprotein layers were separated from the subnatant salt layer by decantation. The decanted supernatant layers were separated by filtration. The separated lipoprotein layer was dried by evaporation, as was the subnatant inorganic salt layer. The dry lipoprotein product was analyzed and found to have the following The purified lipoprotein product was again suspended in ethylene chloride, and the lipoprotein layer separated from the resulting-heterogeneous system. The separated lipoprotein layer was analyzed and found to be free from fatty acid contamination and practically free of inorganic salt.
  • a process for preparing a lipoprotein wherein a proteinaceous substance and a fatty acid halide are reacted in an alkaline medium to form a lipoprotein substance, the steps of forming a substantially anhydrous mixture comprising said lipoprotein substance and an organic fatsolvent having a specific gravity higher than that of the lipoprotein to form a heterogeneous solvent system including a supernatant lipoprotein phase, said lipoprotein substance being at an acidic reaction in said anhydrous mixture, and separating said lipoprotein phase from other phases of said heterogeneous solvent system.
  • a process for preparing a lipoprotein wherein a proteinaceous substance and a fatty acid halide are reacted in an aqueous medium containing an alkali having an alkali metal cation component to form a lipoprotein substance, the steps of dehydrating said lipoprotein substance, mixing the dehydrated lipoprotein substance with an organic fat solvent having a specific gravity higher than that of the lipoprotein, acidifying the resulting mixture with an anhydrous gaseous mineral acid to form a substantially anhydrous heterogeneous solvent system including a supernatant lipoprotein phase, and separating said lipoprotein phase from other phases in said heterogeneous solvent system.
  • a process for preparing a lipoprotein wherein a 6 proteinaceous substance and a fatty acid chloride are reacted in an aqueous medium containing an alkalinizing agent having an alkali metal cation component and wherein the resulting condensation product is substantially dehydrated while being maintained at a pH of at least 6.5, the steps of mixing said dehydrated condensation product with an organic fat solvent having a specific gravity higher than that of said lipoprotein, infusing into the resulting solvent mixture an anhydrous organic solvent-dispersible acid in such amount as to adjust the pH of said condensation product to within the range of pH 4.5 to 5.5, and separating the supernatant lipoprotein phase from the other phases of said solvent mixture.

Description

United States Patent PREPARATION OF urornornrus Edward F. Cavanaugh, Wilmette, 111., assignor to Armour and Company, Chicago, 111., a corporation of Illinois No Drawing. Application May 16, 1955, Serial No. 508,825
Claims. (Ci. 260-112) Schotten' Baumann procedure which involves treating the proteiiiaceous' substance with hydrogen peroxide prior to reaotion there'of'with'thefatty acid halide to obtain an increased content of fatty acid component in the resultin'g-lipoprotein.
' In ca ooii'tained-in'the'heaction mixture to form a soap and an inorganic halide. Consequently, the lipoprotein reaction jroduct 'may be contaminated with the soap and the inunreacted alkali:
Amobject-of-this-invention is the provision of a proccas ier; preparing a purified lipoprotein. Another object is,the ,proyi si on of'a process for separating soap and salt contaminantsr' of lipoprotein products. Other objects and, adyantages 10f thisinvention will become apparent as the specification proceeds.
In one aspect of this invention a lipoprotein substance, obtained; by reacting a proteinaceous substance and a fatty-acid halide in an alkaline mediiun and dehydrating the resulting reaction product,.-may be purified by a process 3 which involves mixing such lipoprotein with an organicfatsolvent having a specific gravity higher than that of-the-lipopnotein.' The mixture of this organic fat solventand the lipoprotein substance should be achieved in a substantially anhydrous system, and the lipoprotein substance should be maintained at an acidic reaction in such solvent' mixture. The acidification of the lipoprotein substance converts the soap contaminant thereof to the free fatty acid, and results in the formation of a salt therein. When this mixture is brought to an equilibrium state, there is produced a heterogeneous solvent system, including a salt phase subjacent to a fat solvent phase, and a lipoprotein phase superimposed upon such fat solvent phase. Then, the lipoprotein phase may be separated from the other phases in this heterogeneous system to provide a substantially purified lipoprotein product.
The lipoprotein substance employed in this purification pnocedure may be prepared by reacting any proteinaceous substance With any fatty acid halide. The term proteinaceous substance employed herein means derived proteins such as proteoses, polypeptides and peptones, as well as whole pr0t eins.- Preferably, this fatty acid halide reactant-contains from '1 to 22 carbon atoms, and espengout this Sclrotten-Baumann procedure, a portion 'ofthe fatty acid' halide reacts with the alkali:
or'ganicsalt. --Also,- suchreaction product may contain cially desirable results are obtained with fatty acid halides containing from 12 to 18 carbon atoms. Also, this fatty acid halide reactant can. be derived from a mixture of fatty acids, such as are prepared from tallow and soya bean. As suitable fatty acid halides for use in preparing this lipoprotein substance, I mention, for example, the halide derivatives of such fatty acids as oleic, palmitic, lauric, capric, stearic, etc. The halide component of this fatty acid halide reactant may be bromine, fluorine, chlorine, etc. but better purification of the lipoprotein substance can be achieved when it is derived from a fatty acid chloride reactant.
The proteinaceous substance and the fatty acid halide may be reacted in an alkaline medium to form a lipoprotein reaction product. The reaction mixture should include an alkali having a cation capable of reacting with the anion of an acid to form a salt. Better results are obtained when an inorganic alklali is included in the reaction mixture, and an especially desirable purification of the lipoprotein reaction product is achieved with an alkali having an alkali metal cation, e. g. sodium, potassium, etc.
The l-ipoprotein reaction product should be dehydrated while being maintained at a substantially neutral or alkaline pH. I have found that the acidification of such reaction product prior to drying apparently increases the melting point and viscosity thereof such that it is difficult to obtain the lipoprotein substance in a substantially anhydrous form. Preferably, the reaction product is maintained at a pH of at least pH 6.5 during this drying step, and especially desirable dehydration is obtained when the reaction product has a pH of at least pH 7.5. The
drying of this lipoprotein reaction product may be ob tained by such methods as evaporation, lyophilization,
etc.
The dehydrated lipoprotein substance may contain such;
contaminants as soap, residual alkaliand a salt: Prepara tory to purification, the dehydrated lipdprotein substance may be pulverized'to produce greater exposure of the contaminants therein to' the acidifying agent and to the organic fat solvent.
minution, grinding or milling. I
out by charging the lipoprotein substance into a suitable vessel, and then charging into the vessel the organic fat solvent. The. mixing of the lipoprotein substanceand the fat solvent may be achieved by pumping, stirring, churning, etc.
The acidification of the lipoprotein substance may be obtained by contacting this solventmixture with an anhydrous acid which is dispersible in such solvent mixture. By dispersible, I mean that the anhydrous acid should be either soluble in the organic fat solvent or in the gaseous state such that it may be bubbled through the solvent mixture. I have found that substantially all of the soap contaminant of the lipoprotein substance may be converted to the free fatty acid by infusing into the solvent mixture acid in such amount as to adjust the pH of the lipoprptein substance to less than about pH 5.5. I prefer to obtain conversion of the soap contaminant to the free fatty acid by adjusting the pH of the lipoprotein substance to about pH 5.0, and usually a pH within the range of pH 5.5 to 4.5 is sufiicient to obtain conversion of the soap contaminant to the free fatty acid. As acids suitable for mixing with the solvent mixture to obtain conversion of the soap contaminant to the free. fatty acid, I mention, for example, mineral acid anhydrides, e. g. hydrochloric, sulfuric, sulfurous and phos phoric, and organic acids, e. g. oxalic. r
Patented June 4, 1957 The pulverizing of this lipoprotein substance may be obtained by a method such as cornthe other hand, the specific gravity of this organic fatsolvent should be less than that of the inorganic salt. Consequently, the specific gravity of such solvent may be less than about 1.9 to 2.7. I mention, for example, such suitable organic fat solvents, together with their specific gravities, as: chloroform 1.498, carbontetrachloride 1.595, trichlorethylene 1.456, dioxane 1.034, chlorobenzene 1.107, and ethylene dichloride 1.257.
The ratio of organic fat solvent to lipoprotein substance included in this solvent mixture may be increased in accordance with an increased concentration of contaminant substances contained in such lipoprotein substance. I have found that the dehydrated lipoprotein product generally contains not more than 40% by weight of such contaminant substances, and more often the concentration of contaminants therein is less than 25% by weight. However, it is seldom that the concentration of these contaminants in the lipoprotein product is less than about butinmore efiicient operation it may be possible to obtain a concentration of contaminants therein of about 3 to 6%. Consequently, in the usual practice a ratio of fat solvent to lipoprotein substance of at least about 2 is suitable for carrying out this purification, and for practical considerations a ratio of fat solvent to lipoprotein substance of less than about 10 is convenient.
After dispersing the liproprotein substance in the organic fat solvent, the resulting solvent mixture may be settled to obtain an equilibrium state therein, and to provide the heterogeneous solvent system. In this heterogeneous system, the contaminant free fatty acid dissolves inthe organic fat solvent forming a layer subjacent to the lipoprotein phase and superimposed upon a salt phase. The lipoprotein phase may be separated from the other phases by draining, skimming, etc. In the former method, the subnatant organic solvent and salt phases can be drained from the bottom of the mixing vessel, and the residual lipoprotein recovered from the bottom of the vessel. The latter separation method involves skimming the lipoprotein layer from the top of the mixing vessel. The residual organic fat solvent may be removed from the separated lipoprotein by evaporation, etc. i
This invention can be more fully illustrated by the following specific examples:
Example I The skimmed lipoprotein layer was dried by evaporation.
This dry product was analyzed and found to contain 96% of lipoprotein and 4% of sodium chloride. The subnatant salt layer was also separated from the purification mixture, and upon analysis was found to contain 85% of sodium chloride.
Example II A lipoprotein product, obtained by reacting gelatin with 4 a fatty acid chloride was prepared. This lipoprotein product, had a pH of 53, and its composition was as follows:
Percent Lipoprotein 76.9 Sodium chloride 16.6 Free fatty acid 6.5
This lipoprotein product, in the amount of 10 gm., was suspended in cc. of trichloroethylene and the resulting mixture was settled to form three phases. The supernatant lipoprotein phase was separated by skimming, and the skimmed lipoprotein dried by evaporation. The dry product was analyzed and found to have the following composition:
Percent Lipoprotein 92.6 Sodium chlor 7.4
Example III A reaction product of lard flake fatty acid chlorides and gelatin was prepared. This lipoprotein product had a pH of 7.7, and the following composition:
Percent Lipoprotein 48 Free fatty acid 22.3 Sodium chlor e 25.7
This lipoprotein product, in the amount of 100 gm., was suspended in 3000 cc. of ethylene dichloride. Gaseous hydrochloric acid was added to this suspension until a pH of 4.7-5.0 was obtained. After settling, the supernatant solvent and lipoprotein layers were separated from the subnatant salt layer by decantation. The decanted supernatant layers were separated by filtration. The separated lipoprotein layer was dried by evaporation, as was the subnatant inorganic salt layer. The dry lipoprotein product was analyzed and found to have the following The purified lipoprotein product was again suspended in ethylene chloride, and the lipoprotein layer separated from the resulting-heterogeneous system. The separated lipoprotein layer was analyzed and found to be free from fatty acid contamination and practically free of inorganic salt.
While in the foregoing specification various embodiments of this invention have been set forth and many details thereof elaborated for the purpose of illustration, it will be apparent to those skilled in the art that this invention is susceptible to other embodiments and that many of these details can be varied widely without departing from the basic concept and spirit of this invention.
I claim:
1. In a process for preparing a lipoprotein, wherein a proteinaceous substance and a fatty acid halide are reacted in an alkaline medium to form a lipoprotein substance, the steps of forming a substantially anhydrous mixture comprising said lipoprotein substance and an organic fatsolvent having a specific gravity higher than that of the lipoprotein to form a heterogeneous solvent system including a supernatant lipoprotein phase, said lipoprotein substance being at an acidic reaction in said anhydrous mixture, and separating said lipoprotein phase from other phases of said heterogeneous solvent system.
2. In a process for preparing a lipoprotein, wherein a proteinaceous substance and a fatty acid halide are reacted to form a lipoprotein substance, the. steps of forming a substantially anhydrous mixture comprising said lipoprotein substance and an organic fat-solvent having a specific gravity higher than that of the lipoprotein, in-
fusing said anhydrous mixture with an anhydrous acidformed therein in association with said lipoprotein, settling said mixture to form a heterogeneous solvent system including a supernatant lipoprotein phase, and separating said lipoprotein phase from other phases of said heterogeneous solvent system.
3. The process of claim 2 in which said fatty acid halide is an oleic acid halide.
4. The process of claim 2 in which said fatty acid halide is a fatty acid chloride.
5. The process of claim 2 in which said proteinaceous substance is gelatin.
6. In a process for preparing a lipoprotein, wherein a proteinaceous substance and a fatty acid halide are reacted in an aqueous medium containing an alkali having an alkali metal cation component to form a lipoprotein substance, the steps of dehydrating said lipoprotein substance, mixing the dehydrated lipoprotein substance with an organic fat solvent having a specific gravity higher than that of the lipoprotein, acidifying the resulting mixture with an anhydrous gaseous mineral acid to form a substantially anhydrous heterogeneous solvent system including a supernatant lipoprotein phase, and separating said lipoprotein phase from other phases in said heterogeneous solvent system.
7. The process of claim 6 in which said alkali metal 25 cation component is a sodium component.
8. The process of claim 6 in which said anhydrous gaseous mineral acid is gaseous hydrochloric acid.
9. In a process for preparing a lipoprotein, wherein a 6 proteinaceous substance and a fatty acid chloride are reacted in an aqueous medium containing an alkalinizing agent having an alkali metal cation component and wherein the resulting condensation product is substantially dehydrated while being maintained at a pH of at least 6.5, the steps of mixing said dehydrated condensation product with an organic fat solvent having a specific gravity higher than that of said lipoprotein, infusing into the resulting solvent mixture an anhydrous organic solvent-dispersible acid in such amount as to adjust the pH of said condensation product to within the range of pH 4.5 to 5.5, and separating the supernatant lipoprotein phase from the other phases of said solvent mixture.
10. The process of claim 9 in which said organic fat solvent is ethylene dichloride.
References Cited in the file of this patent UNITED STATES PATENTS 2,113,819 Tucker Apr. 12, 1938 2,454,915 Fevold et a1. Nov. 30, 1948 2,460,980 Fraenkel-courat et al. Feb. 8, 1949 2,603,630 Aries July 15, 1952 OTHER REFERENCES MacArdle: Use of Solvents (Van Nostrand) pp. 129- 130, 133-134 (1925).
Anson et 21.: Advances in Protein Chem, vol. 1, page 20 (1944).

Claims (1)

1. IN A PROCESS FOR PREPARING A LIPOPROTEIN, WHEREIN A PROTEINACEOUS SUBSTANCE AND A FATTY AID HALIDE ARE REACTED IN AN ALKALINE MEDIUM TO FORM A LIPOPROTEIN SUBSTANCE, THE STEPS OF FORMING A SUBSTANTIALLY ANHYDROUS MIXTURE COMPRISING SAID LIPOPROTEIN SUBSTANCE AND AN ORGANIC FAT SOLVENT HAVING A SPECIFIC GRAVITY HIGHER THAN THAT OF THE LIPOPROTEIN TO FORM A HETEROGENEOUS SOLVENT SYSTEM INCLUDING A SUPERNATANT LIPOPROTEIN PHASE, SAID LIPOPROTEIN SUBSTANCE BEING AT AN ACIDIC REACTION IN SAID ANHYDROUS MIXTURE, AND SEPARATING SAID LIPOPROTEIN PHASE FROM OTHER PHASES OF SAID HETEROGENEOUS SOLVENT SYSTEM.
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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3223528A (en) * 1960-07-18 1965-12-14 Vrancken Marcel Nicolas Gelatin derivatives and photographic silver halide emulsion layers
US4840937A (en) * 1985-04-06 1989-06-20 Koken Co., Ltd. Surfactant composed of acylated collagen or acylated gelatine and a production process thereof
USRE36359E (en) * 1991-04-24 1999-10-26 Kuraray Co., Ltd. Long chain carboxylic acid imide ester

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2113819A (en) * 1936-11-02 1938-04-12 Procter & Gamble Process of preparing fatty acid condensation products
US2454915A (en) * 1947-05-21 1948-11-30 Harry L Fevold Isolation of lipovitellenin from egg yolk
US2460980A (en) * 1945-09-27 1949-02-08 Heinz L Fraenkel-Conrat Process for the preparation of isocyanate derivatives of proteins
US2603630A (en) * 1948-12-31 1952-07-15 Robert S Aries Method for extracting proteins from yeast

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2113819A (en) * 1936-11-02 1938-04-12 Procter & Gamble Process of preparing fatty acid condensation products
US2460980A (en) * 1945-09-27 1949-02-08 Heinz L Fraenkel-Conrat Process for the preparation of isocyanate derivatives of proteins
US2454915A (en) * 1947-05-21 1948-11-30 Harry L Fevold Isolation of lipovitellenin from egg yolk
US2603630A (en) * 1948-12-31 1952-07-15 Robert S Aries Method for extracting proteins from yeast

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3223528A (en) * 1960-07-18 1965-12-14 Vrancken Marcel Nicolas Gelatin derivatives and photographic silver halide emulsion layers
US4840937A (en) * 1985-04-06 1989-06-20 Koken Co., Ltd. Surfactant composed of acylated collagen or acylated gelatine and a production process thereof
USRE36359E (en) * 1991-04-24 1999-10-26 Kuraray Co., Ltd. Long chain carboxylic acid imide ester

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