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Patent · US10130830B2 · B2 · US

Preservative systems comprising cationic surfactants

(11) Publication number
US10130830B2
(21) Application number
11/997,160
(22) Filing date
2005-08-01
(30) Priority date
2005-08-01
(43) Publication date
2018-11-20
(45) Date of grant
2018-11-20
(51) IPC
A01N 37/12; A01N 37/18; A01N 43/04; A01P 1/00; A23L 3/3463; A61K 8/18; A61K 8/73; A61K 8/81; C07C 229/04; A23B 4/20; A23B 4/24; A23B 7/154; A23B 7/157; A23L 3/3508; A23L 3/3517; A23L 3/3526; A23L 3/3544; A23L 3/358; A61K 8/44; A61K 8/49; A61Q 19/00; A61Q 19/10
(52) CPC
  • A61Q Specific use of cosmetics or similar toiletry preparations: 19/10, 19/00
  • A23B Preservation of foods, foodstuffs or non-alcoholic beverages; chemical ripening of fruit or vegetables: 2/754, 2/758, 2/762, 2/771, 2/788, 4/20, 4/24, 7/154, 7/157
  • A23L Foods, foodstuffs or non-alcoholic beverages, not otherwise provided for; preparation or treatment thereof: 3/3508, 3/3517, 3/3526, 3/3544, 3/358
  • A61K Preparations for medical, dental or toiletry purposes: 2800/524, 8/44, 8/442, 8/4946
  • Y02A Technologies for adaptation to climate change: 40/90, 40/944
(73) Assignee
Laboratorios Miret SA
(72) Inventors
Jordi Miret Carceller; Sergi Figueras Roca; Roger Segret Pons
(54) Title
Preservative systems comprising cationic surfactants
(57) Abstract

Preservative systems on the basis of cationic surfactants are known i n the art, a typical example of such cationic surfactants is the ethyl ester of the lauramide of arginine monohydrochloride (LAE) (2). Besides the chloride form the corresponding bromide and sulphate salts are known. It was found that other salts of the cationic surfactants display excellent properties, such as the salts of lactic acid, glutamic acid and acetic acid. It was further found that the combination of the cationic surfactants with at least one salt of an organic or inorganic acid displayed an excellent preservative action. A further preservative system with favourable properties was the combination of the cationic surfactants with at least one ester compound, amide or enzyme inhibitor. Also the combination of the cationic surfactant with a further cationic molecule such as ethyl arginate, glucosamine or chitosan led to an effective preservative system. A further effective preservative system turned out to be the cationic surfactant in encapsulated form.

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Claims (8)

  1. A preservative system comprising a cationic surfactant, of the formula: wherein X − is an anion derived from an acid selected from the group consisting of lactic acid and glutamic acid.
  2. A preservative system comprising: (a) a cationic surfactant, of the formula: wherein X − is an anion derived from organic or inorganic acids, and (b) at least one salt selected from the group consisting of sodium citrate, sodium glutamate, sodium fumarate, sodium gluconate, sodium laurate, sodium lactate, sodium hexametaphosphate, sodium tertiary butyl hydroquinonate, sodium propylparabenate, glucosamine hydrochloride and ethanolamine hydrochloride, and combinations thereof, excluding salts of sorbic acid.
  3. A preservative system comprising a cationic surfactant, of the formula: wherein X − is an anion derived from organic or inorganic acids, and wherein the cationic surfactant is in an encapsulated form.
  4. The preservative system of claim 3, wherein the encapsulated form is an oil-in-water emulsion.
  5. The preservative system of claim 4, wherein the oil is selected from the group consisting of palm oil having a melt point of 35-80° C., soy bean oil, and sunflower oil.
  6. The preservative system of claim 1, further comprising a preservative composition including: (a) a cationic surfactant, the surfactant comprising the condensation product of fatty acids and esterified dibasic amino acids, wherein the surfactant has the formula: where: X − is selected from the group consisting of Br −, CL −, and HSO 4 −, R 1: is a straight alkyl chain of a saturated fatty acid or a hydroxy acid having 8 to 14 carbon atoms linked to an α-amino group via an amide bond; R 2: is a straight or branched alkyl chain having from 1 to 18 carbon atoms or is aromatic; R 3 is selected from the group consisting of: - NH 3, and n is from 0 to 4, and (b) at least one salt of an organic or inorganic acid, excluding salts of sorbic acid.
  7. A preservative system comprising a cationic surfactant, of the formula: wherein X − is an anion derived from organic or inorganic acids and wherein the carionic surfactant is an encapsulated form in which the cationic surfactant is coated with a coating agent selected from the group consisting of vegetable oils, animal oils, mineral oils, vegetable fats, animal fats, mineral fats, vegetable biopolymers, animal biopolymers, lecithin, and cyclodextrins, and combinations thereof.
  8. The preservative system of claim 7, wherein the coating agent is applied with an encapsulation technique based on physical methods selected from the group consisting of spray chilling, spray drying, rotary disk atomization, fluid bed coating, stationary nozzle co-extrusion, centrifugal head co-extrusion, submerged nozzle extrusion and pan coating.

Description

This invention relates to new preservative systems on the basis of cationic surfactants.

In the art it is known to use a preservative system which comprises a cationic surfactant, derived from the condensation of fatty acids and esterified dibasic amino acids, having the formula (1):

where:

where n is from 0 to 4.

Cationic surfactants are known as preservatives used in the food industry. Due to their composition, food products are susceptible to act as a culture medium for micro-organisms and this constitutes a possible risk to human health. Thus food products require good protection against microbial contamination. During long-time use the class of the cationic surfactants has turned out to be highly effective against microbial proliferation and at the same time safe for intake in humans and mammals in general.

Due to their composition, many cosmetic products are prone to act as a culture medium for micro-organisms, and this can possibly cause changes to the cosmetic preparation and constitute a risk to human health as well. Thus, a cosmetic composition necessarily requires good protection against microbiological contamination. For this reason, a large number of preservatives to inhibit or reduce the microbial population is used.

Most of the preservative systems currently used display incompatibilities with the human skin, such as irritations and allergies and are toxic to human beings as well.

Citations (17)

  • US3707505A
  • GB1352420A
  • WO1994019027A1
  • WO1996021642A1
  • US5780658A
  • JPH10114618A
  • US6277359B1
  • WO2001094292A1
  • US20020119109A1
  • WO2002087328A2
  • US20040122095A1
  • US20040166082A1
  • US20040175350A1
  • US20040265443A1
  • US7029698B2
  • WO2003064669A1
  • WO2003094638A1
Record as JSON
{
  "publication_number": "US10130830B2",
  "country": "US",
  "kind": "B2",
  "title": "Preservative systems comprising cationic surfactants",
  "abstract": "Preservative systems on the basis of cationic surfactants are known i n the art, a typical example of such cationic surfactants is the ethyl ester of the lauramide of arginine monohydrochloride (LAE) (2). Besides the chloride form the corresponding bromide and sulphate salts are known. It was found that other salts of the cationic surfactants display excellent properties, such as the salts of lactic acid, glutamic acid and acetic acid. It was further found that the combination of the cationic surfactants with at least one salt of an organic or inorganic acid displayed an excellent preservative action. A further preservative system with favourable properties was the combination of the cationic surfactants with at least one ester compound, amide or enzyme inhibitor. Also the combination of the cationic surfactant with a further cationic molecule such as ethyl arginate, glucosamine or chitosan led to an effective preservative system. A further effective preservative system turned out to be the cationic surfactant in encapsulated form.",
  "claims": [
    "1. A preservative system comprising a cationic surfactant, of the formula: wherein X − is an anion derived from an acid selected from the group consisting of lactic acid and glutamic acid.",
    "2. A preservative system comprising: (a) a cationic surfactant, of the formula: wherein X − is an anion derived from organic or inorganic acids, and (b) at least one salt selected from the group consisting of sodium citrate, sodium glutamate, sodium fumarate, sodium gluconate, sodium laurate, sodium lactate, sodium hexametaphosphate, sodium tertiary butyl hydroquinonate, sodium propylparabenate, glucosamine hydrochloride and ethanolamine hydrochloride, and combinations thereof, excluding salts of sorbic acid.",
    "3. A preservative system comprising a cationic surfactant, of the formula: wherein X − is an anion derived from organic or inorganic acids, and wherein the cationic surfactant is in an encapsulated form.",
    "4. The preservative system of claim 3, wherein the encapsulated form is an oil-in-water emulsion.",
    "5. The preservative system of claim 4, wherein the oil is selected from the group consisting of palm oil having a melt point of 35-80° C., soy bean oil, and sunflower oil.",
    "6. The preservative system of claim 1, further comprising a preservative composition including: (a) a cationic surfactant, the surfactant comprising the condensation product of fatty acids and esterified dibasic amino acids, wherein the surfactant has the formula: where: X − is selected from the group consisting of Br −, CL −, and HSO 4 −, R 1: is a straight alkyl chain of a saturated fatty acid or a hydroxy acid having 8 to 14 carbon atoms linked to an α-amino group via an amide bond; R 2: is a straight or branched alkyl chain having from 1 to 18 carbon atoms or is aromatic; R 3 is selected from the group consisting of: - NH 3, and n is from 0 to 4, and (b) at least one salt of an organic or inorganic acid, excluding salts of sorbic acid.",
    "7. A preservative system comprising a cationic surfactant, of the formula: wherein X − is an anion derived from organic or inorganic acids and wherein the carionic surfactant is an encapsulated form in which the cationic surfactant is coated with a coating agent selected from the group consisting of vegetable oils, animal oils, mineral oils, vegetable fats, animal fats, mineral fats, vegetable biopolymers, animal biopolymers, lecithin, and cyclodextrins, and combinations thereof.",
    "8. The preservative system of claim 7, wherein the coating agent is applied with an encapsulation technique based on physical methods selected from the group consisting of spray chilling, spray drying, rotary disk atomization, fluid bed coating, stationary nozzle co-extrusion, centrifugal head co-extrusion, submerged nozzle extrusion and pan coating."
  ],
  "description_excerpt": "This invention relates to new preservative systems on the basis of cationic surfactants.\n\nIn the art it is known to use a preservative system which comprises a cationic surfactant, derived from the condensation of fatty acids and esterified dibasic amino acids, having the formula (1):\n\nwhere:\n\nwhere n is from 0 to 4.\n\nCationic surfactants are known as preservatives used in the food industry. Due to their composition, food products are susceptible to act as a culture medium for micro-organisms and this constitutes a possible risk to human health. Thus food products require good protection against microbial contamination. During long-time use the class of the cationic surfactants has turned out to be highly effective against microbial proliferation and at the same time safe for intake in humans and mammals in general.\n\nDue to their composition, many cosmetic products are prone to act as a culture medium for micro-organisms, and this can possibly cause changes to the cosmetic preparation and constitute a risk to human health as well. Thus, a cosmetic composition necessarily requires good protection against microbiological contamination. For this reason, a large number of preservatives to inhibit or reduce the microbial population is used.\n\nMost of the preservative systems currently used display incompatibilities with the human skin, such as irritations and allergies and are toxic to human beings as well.",
  "cpc": [
    "A61Q 19/10",
    "A23B 2/754",
    "A23B 2/758",
    "A23B 2/762",
    "A23B 2/771",
    "A23B 2/788",
    "A23B 4/20",
    "A23B 4/24",
    "A23B 7/154",
    "A23B 7/157",
    "A23L 3/3508",
    "A23L 3/3517",
    "A23L 3/3526",
    "A23L 3/3544",
    "A23L 3/358",
    "A61K 2800/524",
    "A61K 8/44",
    "A61K 8/442",
    "A61K 8/4946",
    "A61Q 19/00",
    "Y02A 40/90",
    "Y02A 40/944"
  ],
  "ipc": [
    "A01N 37/12",
    "A01N 37/18",
    "A01N 43/04",
    "A01P 1/00",
    "A23L 3/3463",
    "A61K 8/18",
    "A61K 8/73",
    "A61K 8/81",
    "C07C 229/04",
    "A23B 4/20",
    "A23B 4/24",
    "A23B 7/154",
    "A23B 7/157",
    "A23L 3/3508",
    "A23L 3/3517",
    "A23L 3/3526",
    "A23L 3/3544",
    "A23L 3/358",
    "A61K 8/44",
    "A61K 8/49",
    "A61Q 19/00",
    "A61Q 19/10"
  ],
  "assignees": [
    "Laboratorios Miret SA"
  ],
  "inventors": [
    "Jordi Miret Carceller",
    "Sergi Figueras Roca",
    "Roger Segret Pons"
  ],
  "filing_date": "2005-08-01",
  "publication_date": "2018-11-20",
  "grant_date": "2018-11-20",
  "priority_date": "2005-08-01",
  "application_number": "US-99716005-A",
  "family_id": "36204714",
  "cited_by_count": 876,
  "citations": [
    "US3707505A",
    "GB1352420A",
    "WO1994019027A1",
    "WO1996021642A1",
    "US5780658A",
    "JPH10114618A",
    "US6277359B1",
    "WO2001094292A1",
    "US20020119109A1",
    "WO2002087328A2",
    "US20040122095A1",
    "US20040166082A1",
    "US20040175350A1",
    "US20040265443A1",
    "US7029698B2",
    "WO2003064669A1",
    "WO2003094638A1"
  ]
}

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