Gels including bioactive components

• US 6,242,509 B1
• Filed: 04/15/1999
• Issued: 06/05/2001
• Est. Priority Date: 10/18/1996
• Status: Expired due to Term

• Current Assignee: Croda International PLC
• Original Assignee: Bush Boake Allen, Inc. (International Flavors & Fragrances Incorporated), International Paper Company
• Inventors: Heydel, Jochen, Pavlin, Mark S., Frihart, Charles R., MacQueen, Richard C., Williams, Virgil A. G., Gordon, Ronald L., Berger, Vivian
• Primary Examiner(s): HAMPTON HIGHTOWER, PATRICIA
• Application Number:
  US09/292,486
• Time in Patent Office: 782 Days
• Field of Search: 424/78.02, 424/78.05, 424/78.4, 424/78.08, 424/400, 424/404, 424/484, 424/486, 528/310, 528/332, 528/292, 528/339.3, 528/272, 528/345, 528/288, 528/322, 528/324, 528/326, 524/606, 523/122
• US Class Current: 523/122
• CPC Class Codes: A61K 8/042 Gels
• CPC Class Codes: A61K 8/88 Polyamides
• CPC Class Codes: A61Q 13/00 Formulations or additives for perfume preparations essential oils or perfumes per se C11B9/00
• CPC Class Codes: A61Q 17/00 Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
• CPC Class Codes: A61Q 17/02 containing insect repellants
• CPC Class Codes: A61Q 17/04 Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
• CPC Class Codes: A61Q 19/00 Preparations for care of the skin
• CPC Class Codes: B01J 13/0065 containing an organic phase
• CPC Class Codes: C08G 69/34 using polymerised unsaturated fatty acids
• CPC Class Codes: C08G 69/44 Polyester-amides
• CPC Class Codes: C08G 73/0206 Polyalkylene(poly)amines
• CPC Class Codes: C08G 73/0273 Polyamines containing heterocyclic moieties in the main chain
• CPC Class Codes: C08G 73/0633 with only two nitrogen atoms in the ring
• CPC Class Codes: C11C 5/002 Ingredients

Abstract

An ester-terminated dimer acid-based polyamide may be blended with a solvent to form a gel. The solvent may be flammable, and a wick may be added to the resulting gel so as to form a candle. Depending on the composition, the candle may be formed into a free standing pillar, or may be better suited to being placed in a container. The solvent may be mineral oil. A solid coating may be placed around the candle, for advantages including to enhance the clarity and/or mechanical stability of the gelled body, and to eliminate the tendency of a gel to have an oily feel and to accept noticeable fingerprints. The ester-terminated dimer acid-based polyamide may also be combined with an active ingredient, such as a fragrance, colorant, insect-repellant, insecticide, bioactive ingredient or the like, to afford a delivery vehicle for the active ingredient.

Claims

1. A composition comprising ester-terminated dimer acid-based polyamide (ETDABP) and at least one bioactive agent, the composition having a consistency of a gel, wherein the bioactive agent is selected from the group consisting of anti-fungal agents, hemorrhoid treatment agents, anti-itching agents, wart-treatment agents, antibiotics and topical analgesics.

4. The composition of claim 1 wherein the ETDABP is the reaction product of reactants comprising dimer acid, diamine and monoalcohol.

5. The composition of claim 4 wherein the diamine is selected from the group consisting of ethylenediamine, 1,2-diaminopropane, 1,3-diaminopropane, 1,4-diaminobutane, 1,2-diamino-2-methylpropane, 1,3-diaminopentane, 1,5-diaminopentane, 2,2-dimethyl-1,3-propanediamine, 1,6-hexanediamine, 2-methyl-1,5-pentanediamine, 1,7-diaminoheptane, 1,8-diaminooctane, 2,5-dimethyl-2,5-hexanediamine, 1,9-diaminononane, 1,10-diaminodecane, 1,12-diaminododecane, diaminophenanthrene, 4,4′

-methylenebis(cyclohexylamine), 2,7-diaminofluornen, phenylene diamine, adamantane diamine, 2,4,6-trimethyl-1,3-phenylenediamine, 1,3-cyclohexanebis(methylamine), 1,8-diamino-p-menthane, 2,3,5,6-tetramethyl-1,4-phenylenediamine, diaminonaphthalene and 4-amino-2,2,6,6-tetramethylpiperidine.

6. The composition of claim 4 wherein the monoalcohol has the formula R¹—

OH, wherein R¹ is a hydrocarbon group.

7. The composition of claim 1 wherein the ETDABP is prepared by a method comprising reacting x equivalents of carboxylic acid from diacid or a reactive equivalent thereof, y equivalents of amine from diamine and z equivalents of hydroxyl from monoalcohol or a reactive equivalent thereof, wherein at least about 10% of the carboxylic acid equivalents are from polymerized fatty acid, and monoalcohol is substantially the only monofunctional reactant used to form the gellant, wherein each of x, y and z is greater than 0.

8. The composition of claim 7 wherein 0.9≦

{x/(y+z)}≦

1.1, and 0.1≦

{z/(y+z)}≦

0.7.

9. The composition of claim 1 wherein the ETDABP has the formula (1):

wherein

n designates a number of repeating units such that ester groups constitute from 10% to 50% of the total of the ester and amide groups;

R¹ at each occurrence is independently selected from hydrocarbyl groups;

R² at each occurrence is independently selected from a C_2-42 hydrocarbon group with the proviso that at least 10% of the R² groups have 30-42 carbon atoms;

R³ at each occurrence is independently selected from an organic group containing at least two carbon atoms in addition to hydrogen atoms, and optionally containing one or more oxygen and nitrogen atoms; and

R^3a at each occurrence is independently selected from hydrogen, C_1-10 alkyl and a direct bond to R³ or another R^3a such that the N atom to which R³ and R^3a are both bonded is part of a heterocyclic structure defined in part by R^3a—

N—

R³.

10. The composition of claim 9 wherein

R¹ at each occurrence is independently selected from an alkyl or alkenyl group containing at least 4 carbon atoms;

R² at each occurrence is independently selected from a C_4-42 hydrocarbon group with the proviso that at least 50% of the R² groups have 30-42 carbon atoms; and

R^3a at each occurrence is independently selected from hydrogen, C_1-10alkyl and a direct bond to R³ or another R^3a such that the N atom to which R³ and R^3a are both bonded is part of a heterocyclic structure defined in part by R^3a—

N—

R³, such that at least 50% of the R^3a groups are hydrogen.

2. A composition comprising ester-terminated dimer acid-based polyamide (ETDABP) and at least one bioactive agent, the composition having a consistency of a gel, wherein the bioactive agent is selected from the group consisting of acetylsalicylic acid, acyclovir, 6-[3-(1-adamantyl)-4-methoxyphenyl]-2-naphthoic acid, amphotericin B, ascorbic acid, benzoyl peroxide, betamethasone valerate, chloroxylenol, citric acid, clindamycin phosphate, clobetasol propionate, clotrimazole, cyproheptadine, diclofenac, diphenylhydramine hydrochloride, econazole, erthromycin, estradiol, glycolic acid, glycyrrhetinic acid, hydrocortisone, hydroquinone, ibuprofen, ketoconazole, kojic acid, lactic acid, lidocaine hydrochloride, metronidazole, miconazole, miconazole nitrate, octopirox, 5-n-octanoylsalicylic acid, paracetamol, pramoxine hydrochloride, progesterone, retinoic acid, retinol, salicylic acid, superoxide dismutases, terbinafine, thenaldine, α

-tocopherol, tolnaftate, trimeprazine, 1,8,10-tripropionyl-9-anthrone, undecylenate, and vitamin D.

11. The composition of claim 2 wherein the ETDABP is the reaction product of reactants comprising dimer acid, diamine and monoalcohol.

12. The composition of claim 11 wherein the diamine is selected from the group consisting of ethylenediamine, 1,2-diaminopropane, 1,3-diaminopropane, 1,4-diaminobutane, 1,2-diamino-2-methylpropane, 1,3-diaminopentane, 1,5-diaminopentane, 2,2-dimethyl-1,3-propanediamine, 1,6-hexanediamine, 2-methyl-1,5-pentanediamine, 1,7-diaminoheptane, 1,8-diaminooctane, 2,5-dimethyl-2,5-hexanediamine, 1,9-diaminononane, 1,10-diaminodecane, 1,12-diaminododecane, diaminophenanthrene, 4,4′

-methylenebis(cyclohexylamine), 2,7-diaminofluornen, phenylene diamine, adamantane diamine, 2,4,6-trimethyl-1,3-phenylenediamine, 1,3-cyclohexanebis(methylamine), 1,8-diamino-p-menthane, 2,3,5,6-tetramethyl-1,4-phenylenediamine, diaminonaphthalene and 4-amino-2,2,6,6-tetramethylpiperidine.

13. The composition of claim 11 wherein the monoalcohol has the formula R¹—

OH, wherein R¹ is a hydrocarbon group.

14. The composition of claim 2 wherein the ETDABP is prepared by a method comprising reacting x equivalents of carboxylic acid from diacid or a reactive equivalent thereof, y equivalents of amine from diamine and z equivalents of hydroxyl from monoalcohol or a reactive equivalent thereof, wherein at least about 10% of the carboxylic acid equivalents are from polymerized fatty acid, and monoalcohol is substantially the only monofunctional reactant used to form the gellant, wherein each of x, y and z is greater than 0.

15. The composition of claim 14 wherein 0.9≦

{x/(y+z)}≦

1.1, and 0.1≦

{z/(y+z)}≦

0.7.

16. The composition of claim 2 wherein the ETDABP has the formula (1):

wherein

n designates a number of repeating units such that ester groups constitute from 10% to 50% of the total of the ester and amide groups;

R¹ at each occurrence is independently selected from hydrocarbyl groups;

R² at each occurrence is independently selected from a C_2-42 hydrocarbon group with the proviso that at least 10% of the R² groups have 30-42 carbon atoms;

R³ at each occurrence is independently selected from an organic group containing at least two carbon atoms in addition to hydrogen atoms, and optionally containing one or more oxygen and nitrogen atoms; and

R^3a at each occurrence is independently selected from hydrogen, C_1-10 alkyl and a direct bond to R³ or another R^3a such that the N atom to which R³ and R^3a are both bonded is part of a heterocyclic structure defined in part by R^3a—

N—

R³.

17. The composition of claim 16 wherein

R¹ at each occurrence is independently selected from an alkyl or alkenyl group containing at least 4 carbon atoms;

R² at each occurrence is independently selected from a C_4-42 hydrocarbon group with the proviso that at least 50% of the R² groups have 30-42 carbon atoms; and

R^3a at each occurrence is independently selected from hydrogen, C_1-10alkyl and a direct bond to R³ or another R^3a such that the N atom to which R³ and R^3a are both bonded is part of a heterocyclic structure defined in part by R^3a—

N—

R³, such that at least 50% of the R^3a groups are hydrogen.

3. A composition comprising ester-terminated dimer acid-based polyamide (ETDABP) and at least one bioactive agent, the composition having a consistency of a gel, wherein the bioactive agent is an antibiotic.

18. The composition of claim 3 wherein the ETDABP is the reaction product of reactants comprising dimer acid, diamine and monoalcohol.

19. The composition of claim 18 wherein the diamine is selected from the group consisting of ethylenediamine, 1,2-diaminopropane, 1,3-diaminopropane, 1,4-diaminobutane, 1,2-diamino-2-methylpropane, 1,3-diaminopentane, 1,5-diaminopentane, 2,2-dimethyl-1,3-propanediamine, 1,6-hexanediamine, 2-methyl-1,5-pentanediamine, 1,7-diaminoheptane, 1,8-diaminooctane, 2,5-dimethyl-2,5-hexanediamine, 1,9-diaminononane, 1,10-diaminodecane, 1,12-diaminododecane, diaminophenanthrene, 4,4′

-methylenebis(cyclohexylamine), 2,7-diaminofluornen, phenylene diamine, adamantane diamine, 2,4,6-trimethyl-1,3-phenylenediamine, 1,3-cyclohexanebis(methylamine), 1,8-diamino-p-menthane, 2,3,5,6-tetramethyl-1,4-phenylenediamine, diaminonaphthalene and 4-amino-2,2,6,6-tetramethylpiperidine.

20. The composition of claim 18 wherein the monoalcohol has the formula R¹—

OH, wherein R¹ is a hydrocarbon group.

21. The composition of claim 3 wherein the ETDABP is prepared by a method comprising reacting x equivalents of carboxylic acid from diacid or a reactive equivalent thereof, y equivalents of amine from diamine and z equivalents of hydroxyl from monoalcohol or a reactive equivalent thereof, wherein at least about 10% of the carboxylic acid equivalents are from polymerized fatty acid, and monoalcohol is substantially the only monofunctional reactant used to form the gellant, wherein each of x, y and z is greater than 0.

22. The composition of claim 21 wherein 0.9≦

{x/(y+z)}≦

1.1, and 0.1≦

{z/(y+z)}≦

0.7.

23. The composition of claim 3 wherein the ETDABP has the formula (1):

wherein

n designates a number of repeating units such that ester groups constitute from 10% to 50% of the total of the ester and amide groups;

R¹ at each occurrence is independently selected from hydrocarbyl groups;

R² at each occurrence is independently selected from a C_2-42 hydrocarbon group with the proviso that at least 10% of the R² groups have 30-42 carbon atoms;

R³ at each occurrence is independently selected from an organic group containing at least two carbon atoms in addition to hydrogen atoms, and optionally containing one or more oxygen and nitrogen atoms; and

R^3a at each occurrence is independently selected from hydrogen, C_1-10 alkyl and a direct bond to R³ or another R^3a such that the N atom to which R³ and R^3a are both bonded is part of a heterocyclic structure defined in part by R^3a—

N—

R³.

24. The composition of claim 23 wherein

R¹ at each occurrence is independently selected from an alkyl or alkenyl group containing at least 4 carbon atoms;

R² at each occurrence is independently selected from a C_4-42 hydrocarbon group with the proviso that at least 50% of the R² groups have 30-42 carbon atoms; and

R^3a at each occurrence is independently selected from hydrogen, C_1-10alkyl and a direct bond to R³ or another R^3a such that the N atom to which R³ and R^3a are both bonded is part of a heterocyclic structure defined in part by R^3a—

N—

R³, such that at least 50% of the R^3a groups are hydrogen.