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EP0109074A1 Expired / Lapsed EP ⏱️ 0.0 years remaining

Quarternary ammonium derivatives of amino acid units

Assignee: INOLEX CHEMICAL Co
•
Filing: 1983-11-12
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Granted: —
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Expires: 2003-11-12
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Abstract

Abstract A water-soluble, cationic, quaternary ammonium compound is prepared comprising a lipophilic end group, a linking structure derived from a epihalohydrin, and a hydrophilic end segment containing from 1 to 500 amino acid units. Preferably, the hydrophilic end segment is a polypeptide end segment having 3-30 amino acid units and is derived from a protein hydrolysate.

Inventors

  • 👤 David Massuda

Bibliographic Details

Application Number —
Jurisdiction EP
Data Source google_patents
Last Synchronized 2026-10-30 06:14
CPC Classifications
A; A61; A61Q; A61Q5/00; A61Q5/02; A61K; A61K8/00; A61K8/18; A61K8/30; A61K8/64; A61K8/645; A61K8/65; A61Q5/12; C; C07; C07K; C07K1/00; C07K1/006

Claims Analysis

Total Claims: 17
Claim 1
Independent Claim 140 words
A water soluble, cationic quaternary ammonium derivative of a polypeptide having the formula: wherein R 1 is selected from at least one C 12 to C 22 alkyl radical and carboxamide radicals of the formula wherein R 5 is selected from at least one C 12 to C 22 alkyl radical and R 6 is selected from at least one C 2 to C 3 alkylene radical, where R 2 is a C l to C 4 alkyl radical and R 3 is selected from the group consisting of C 1 to C 4 radicals and at least one C 12 to C 22 alkyl radical; -R 4 - is a linking structure derived from an epihalohydrin, where the halogen atom comprises chlorine and bromine; and -NH[Z] is an amino acid segment containing from 1 to 500 amino acid units.
Claim 2
Dependent Claim 140 words
A water soluble, cationic quaternary ammonium derivative of a polypeptide having the formula: wherein R 1 is selected from at least one C 12 to C 22 alkyl radical and carboxamide radicals of the formula wherein R 5 is selected from at least one C 12 to C 22 alkyl radical and R 6 is selected from at least one C 2 to C 3 alkylene radical, where R 2 is a C l to C 4 alkyl radical and R 3 is selected from the group consisting of C 1 to C 4 radicals and at least one C 12 to C 22 alkyl radical; -R 4 - is a linking structure derived from an epihalohydrin, where the halogen atom comprises chlorine and bromine; and -NH[Z] is an amino acid segment containing from 1 to 500 amino acid units.
Claim 3
Dependent Claim 30 words
The cationic quaternary ammonium derivative of claim 1 wherein the R 1 comprises a C 12 to C 14 alkyl radical and R 2 amd R 3 are methyl radicals.
Claim 4
Dependent Claim 39 words
The cationic quaternary ammonium derivative of claim 1 wherein R 2 and R 3 are methyl radicals and R 1 is a carboxamide radical comprising a C 12 to C 14 alkyl radical and a C 3 alkylene radical.
Claim 5
Dependent Claim 22 words
The quaternary ammonium derivative of claim 1 wherein the linking structure derived from epihalohydrin is derived from epichlorohydrin and is represented by
Claim 8
Dependent Claim 48 words
The quaternary ammonium derivative of claim 1 wherein [Z] is a polypeptide derivative group derived from hydrolyzed animal collagen protein and has a Formol Nitrogen Value of between about 8 and about 17, and comprises from about 3 to about 30 amino acid units in a polypeptide chain.
Claim 9
Dependent Claim 39 words
The quaternary ammonium derivative of claim 1 wherein the hydrophilic polypeptide derivative group is derived from chemically hydrolyzed animal collagen protein and has an average Formol Nitrogen Value of about 11, and an average molecular weight of about 500.
Claim 10
Dependent Claim 48 words
The quaternary ammonium derivative of claim 1 in which the compound comprises the reaction product of a fatty tertiary amine having at least one C 12 to C 14 alkyl radical group in the fatty chain, epichlorohydrin, and a protein hydrolysate radical derived from hydrolyzed animal collagen protein.
Claim 11
Dependent Claim 173 words
A method of preparing the cationic quaternary ammonium derivative of claim 1 which comprises the steps of (a) reacting an amine compound of the class consisting of tertiary amines and salts thereof, with an epihalohydrin compound in the presence of water; (b) reacting the aqueous reaction mixture of step (a) with an aqueous solution containing a compound of from 1 to 500 amino acid units to form a cationic quaternary ammonium derivative of the amino acid compound; said tertiary amine having the formula: wherein R 1 is selected from at least one C 12 to C 22 alkyl radical and carboxamide radicals of the formula wherein R 5 is selected from at least one C12 to C 22 alkyl radical and carboxamide R 6 is selected from at least one C 2 to C 3 alkylene radical, wherein R 2 is a C 1 to C 4 alkyl radical and R 3 is selected from the group consisting of C 1 to C 4 radicals and C 12 to C 22 alkyl radicals.
Claim 12
Dependent Claim 17 words
The method of claim 8 wherein said amino acid compound is a polypeptide derived from protein hydrolysis.
Claim 13
Dependent Claim 74 words
The method of claim 9 wherein the reaction of step (a) is carried out at a temperature of between about 50 to about 100 degrees C. and the reaction of step (b) includes the presence of alkali and is carried out at a temperature of between about 70 and about 100 degrees C. for a period of time sufficient to react all the amine groups in the amino acid units in the polypeptide chain.
Claim 14
Dependent Claim 17 words
The method of claim 9 wherein the reaction mixture in step (a) includes a water-miscible organic solvent.
Claim 15
Dependent Claim 105 words
The method of claim 9 wherein a fatty tertiary amine salt, having at least one C 12 to C 14 alkyl radical group in the fatty chain, is reacted with epichlorohydrin in water in step (a), said reaction being carried out at a temperature of about 50 degrees C.; and wherein the hydrophilic polypeptide in step (b) comprises a protein hydrolysate radical derived from hydrolyzed animal collagen protein, said reaction being carried out in the presence of sufficient alkali to adjust the pH value of the reaction mixture to about 10, said reaction being further carried out at a temperature of about 70 degrees C.
Claim 16
Dependent Claim 33 words
A complex of N , N -dimethylcocamido- propylamine with an enzymatically hyrolyzed protein polypeptide having a Formol Nitrogen Value of about 11, said N,N-dimethylcocamidopropylamine and said polypeptide being linked through a 2-hydroxypropylene group.
Claim 17
Dependent Claim 33 words
A complex of N , N -dimethylcocamido- propylamine with an enzymatically hyrolyzed protein polypeptide having a Formol Nitrogen Value of about 11, said N,N-dimethylcocamidopropylamine and said polypeptide being linked through a 2-hydroxypropylene group.
Claim 18
Dependent Claim 32 words
A complex of N,N-dimethyltetradecamido- propyl amine with a chemically hydrolyzed protein polypeptide having a Formol Nitrogen Value of about 17, said N,N-dimethyltetradecamidopropylamine and said polypeptide being linked through a 2-hydroxy propylene group.
Claim 19
Dependent Claim 32 words
A complex of N,N-dimethyltetradecamido- propyl amine with a chemically hydrolyzed protein polypeptide having a Formol Nitrogen Value of about 17, said N,N-dimethyltetradecamidopropylamine and said polypeptide being linked through a 2-hydroxy propylene group.

References Cited (Backward Citations)

FR1149161A Cited
DE1959651A1 Cited
US3738913A Cited
DE2126397A1 Cited
DE2151739A1 Cited
EP0020907A2 Cited

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