Non-isocyanate polyurethane elastomers and compositions comprising such elastomers

Abstract

To provide a polyurethane elastomer which demonstrates efficient thickening and gelling capabilities with non-silicone based topically acceptable solvents, and which can impart a silky and powdery skin feel comparable to silicone elastomers.SOLUTION: A gel composition comprising a non-isocyanate polyurethane (NIPU) elastomer, wherein the NIPU elastomer is a reaction product of: A) a polycarbonate or a mixture of polycarbonates comprising two or more carbonate functional groups; B) a polyamine or a mixture of polyamines comprising two or more amine functional groups, wherein the amine functional groups are either primary or secondary; C) an NIPU reaction catalyst; and D) a topically acceptable carrier fluid, wherein the topically acceptable carrier fluid is a reaction solvent at a concentration of 50% to 99.9% (w / w) of the gel composition, and particles of the NIPU elastomer are dispersed in the topically acceptable carrier fluid.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to gel compositions containing NIPU elastomers prepared by the reaction of polycyclic or poly-non-cyclic carbonates with polyamines, optionally utilizing a catalyst to enhance the rate of elastomer formation, preferably contained in a topically acceptable carrier fluid to form a gel. The gel compositions may also contain personal or healthcare active ingredients. The active ingredients may be incorporated into the gel by either pre-dosing or post-dosing methods. The gel compositions may further be used as components of personal care compositions. [Background technology]

[0002] Silicone elastomers are widely used in personal care applications due to their thickening and gelling properties and unique silky, powdery sensory characteristics. While silicone elastomers are compatible with silicone-based fluids, silicone-based fluids for topical use are gradually disappearing from the personal care industry due to health and environmental concerns. There is a need to develop alternatives to silicone elastomers that exhibit efficient thickening and gelling capabilities with non-silicone-based, topically acceptable solvents (e.g., esters, triglycerides, and alkanes) and impart a silky, powdery skin feel comparable to that of silicone elastomers. Polyurethane elastomers fulfill this need and may be a desirable alternative to silicone elastomers. Non-isocyanate polyurethane (NIPU) elastomers offer an environmentally friendly alternative to isocyanate-derived polyurethanes, which require starting materials synthesized from toxic precursors. Summary of the Invention

[0003] The present disclosure provides: A) polycarbonates, where the carbonate groups are either cyclic or acyclic and optionally contain siloxanes in their backbone; B) polyamines, where the amine groups are either primary or secondary; C) optionally a reaction catalyst; and D) optionally a locally acceptable carrier fluid, wherein said locally acceptable carrier fluid is a reaction solvent or said locally acceptable carrier fluid is added to the reaction after elastomer formation; The present invention relates to a gel composition comprising a non-isocyanate polyurethane (NIPU) elastomer obtained from the reaction of:

[0004] The personal care or healthcare active ingredient (E) can be incorporated into the NIPU elastomer gel by dissolving it in a topically acceptable solvent during the formation of the NIPU elastomer gel (pre-load method) or by mixing it with the formed NIPU elastomer gel (post-load method).

[0005] The present invention relates to: A crosslinked NIPU elastomer network having the following general structure: [ka]

[0006] In the formula, R 1 is an aromatic ring, heterocyclic ring, cyclic alkyl group, linear alkyl group, or branched alkyl group having two or more carbonate functional groups; R 2 is a hydrogen atom, a heteroatom, an aromatic ring, a heterocycle, or an alkyl chain. 3 R is an aromatic ring, heterocyclic ring, cyclic alkyl group, straight chain alkyl group, or branched chain alkyl group having two or more primary or secondary amines. 4 is a hydrogen atom, a heteroatom, an aromatic ring, a heterocycle, a cyclic alkyl group, or a linear alkyl chain.

[0007] A crosslinked NIPU elastomer network having the following general structure: [ka]

[0008] In the formula, R 1 is an aromatic ring, heterocyclic ring, cyclic alkyl group, linear alkyl group, or branched alkyl group having three or more carbonate functional groups; R 2 is a hydrogen atom, a heteroatom, an aromatic ring, a heterocycle, or an alkyl chain. 3 R is an aromatic ring, heterocyclic ring, cyclic alkyl group, straight chain alkyl group, or branched chain alkyl group having two or more primary or secondary amines. 4 is a hydrogen atom, a heteroatom, an aromatic ring, a heterocycle, a cyclic alkyl group, or a linear alkyl chain.

[0009] A crosslinked NIPU elastomer network having the following general structure: [ka]

[0010] In the formula, R 1 is an aromatic ring, heterocyclic ring, cyclic alkyl group, linear alkyl group, or branched alkyl group having three or more cyclic carbonate groups, and R 2 is a hydrogen atom, a heteroatom, an aromatic ring, a heterocycle, or an alkyl chain. 3 R is an aromatic ring, heterocyclic ring, cyclic alkyl group, straight chain alkyl group, or branched chain alkyl group having two or more primary or secondary amines. 4 is a hydrogen atom, a heteroatom, an aromatic ring, a heterocycle, a cyclic alkyl group, or a linear alkyl chain.

[0011] A crosslinked NIPU elastomer network having the following general structure: [ka]

[0012] In the formula, R 1 is an aromatic ring, heterocyclic ring, cyclic alkyl group, or linear or branched alkyl group having three or more cyclic carbonate functional groups; R2 is a hydrogen atom, a heteroatom, an aromatic ring, a heterocycle, or an alkyl chain. 3 R is an aromatic ring, heterocyclic ring, cyclic alkyl group, straight chain alkyl group, or branched chain alkyl group having two or more primary or secondary amines. 4 is a hydrogen atom, a heteroatom, an aromatic ring, a heterocycle, a cyclic alkyl group, or a linear alkyl chain. DETAILED DESCRIPTION OF THE INVENTION

[0013] The present disclosure relates to gel compositions comprising polyurethane elastomers that do not require purification and are formed from the following reaction in a topically acceptable solvent:

[0014] (A) Polycarbonate Component (A) has a molecular structure containing two or more cyclic or acyclic carbonates and can be prepared by a number of methods from alkenes, alkynes, epoxides, vicinal diols, isolated hydroxyl groups, 2-haloalcohols, etc., and must have two or more reactive carbonate functional groups in its molecular structure. A preferred example of a polycarbonate is based on castor oil and has the following structure: [ka]

[0015] wherein R comprises a cyclic or acyclic carbonate.

[0016] Another preferred example of a polycarbonate is based on dilinoleic acid / propanediol copolymer and has the following structure: [ka]

[0017] wherein R comprises a cyclic or acyclic carbonate.

[0018] Another preferred example of a polycarbonate is based on a dilinoleic acid / dilinoleic diol copolymer and has the following structure: [ka]

[0019] wherein R comprises a cyclic or acyclic carbonate.

[0020] Component (A) can contain one or more functional groups in its polymer chain. In one embodiment, the polycarbonate contains one or more siloxanes in its polymer chain, for example, in the polymer backbone.

[0021] (B) Polyamines (the amine groups are either primary or secondary) Component (B) has a molecular structure containing two or more primary or secondary amines. A preferred example of an aliphatic polyamine is hexamethylenediamine, which has the following structure: [ka]

[0022] Another preferred example of an aliphatic polyamine is isophorone diamine, which has the following structure: [ka]

[0023] Another preferred example of an aliphatic polyamine is bis(hexamethylene)triamine, which has the following structure: [ka]

[0024] Another preferred example of an aliphatic polyamine is tris(aminoethyl)amine, which has the following structure: [ka]

[0025] A preferred example of an aromatic polyamine is melamine, which has the following structure: [ka]

[0026] (C) Any reaction catalyst Component (C) is optionally used to increase the rate of NIPU elastomer formation. Titanium alkoxides are preferred catalysts for the synthesis of NIPU elastomer gels due to their favorable toxicity profile and acceptable use in topical products. Preferably, titanium isopropoxide is used as the NIPU catalyst. Zinc, tin, bismuth, and amine-based NIPU catalysts may also be used. Suitable NIPU catalysts include, but are not limited to: Triethylenediamine, N,N,N',N",N"-Pentamethyldiethylenetriamine 1,2-Dimethylimidazole N,N,N',N'-Tetramethyl-1,6-hexanediamine N,N',N'-trimethylaminoethylpiperazine 1,1'-[[3-(dimethylamino)propyl]imino]bispropan-2-ol N,N,N'-trimethylaminoethylethanolamine N,N',N"-Tris(3-dimethylaminopropyl)-hexahydro-s-triazine 1,4-Diazabicyclo[2.2.2]octane 1,5,7-Triazabicyclo[4.4.0]dec-5-ene Stannous octoate Stannous oxalate Stannous oxide Stannous chloride Dioctyltin di(2-hexylhexanoate) solution Dioctyltin dithioglycolate Dioctyltin dilaurate Dioctyltin oxide blend Dibutyltin dilaurate Monobutyltin tris-(2-ethylhexanoate) Dioctyltin diketonate Dioctyltin diacetate Dioctyltin oxide Dibutyltin diacetate Modified dibutyltin diacetate Dibutyltin oxide Monobutyltin dihydroxychloride Organotin oxide Monobutyltin oxide Dioctyltin dicarboxylate Dioctyltin carboxylate Dioctyltin stannoxane Zinc neodecanoate Zinc octanoate Zinc acetylacetonate Zinc oxalate Zinc acetate Bismuth carboxylate Zinc neodecanoate Includes.

[0027] (D) Carrier fluid

[0028] The NIPU elastomer may optionally be contained in a carrier fluid (D). Carrier fluids include any suitable solvent that can be used to prepare the NIPU elastomer. In an exemplary embodiment, the carrier fluid is a "topically acceptable carrier fluid," which is a solvent for topical application to skin surfaces, i.e., skin, lips, mucous membranes, etc. Typically, but not necessarily, the carrier fluid may be the same solvent used to carry out the elastomer reaction described above. Carrier fluids used in the synthesis of NIPU elastomer rubbers and gels may be wholly or partially bio-based, or may not be bio-based. Carrier fluids, including topically acceptable carrier fluids, preferably have a viscosity between 1 and 65 mPas at 20°C. The spreading value of carrier fluids, including topically acceptable carrier fluids, is preferably between 500 and 2500 mm. 2 Suitable topically acceptable carrier fluids for the synthesis of NIPU elastomer rubbers and processing of NIPU elastomer gels include, but are not limited to, esters, triglycerides, hydrocarbons, silicone fluids, and combinations thereof; Bis-diglyceryl polyacyladipate-1 Bis-diglyceryl polyacyladipate-2 Di(caprylic / capric acid) Butylene Glycol ·Butyrospermum Parkii Butter Caprylic / Capric Glycerides Caprylic / capric triglyceride Caprylic / Capric / Myristic / Stearic Triglyceride Caprylic / Capric / Succinic Triglyceride Caprylyl methicone Coco-(caprylic / capric acid) alkyl Decamethylcyclopentasiloxane Decyl oleate Dimethiconol Diphenylsilanediol Dodecamethylcyclohexasiloxane Ethyltrisiloxane Glyceryl Caprylate Citric Acid / Lactic Acid / Linoleic Acid / Glyceryl Oleate Glyceryl Cocoate Glyceryl isostearate Glyceryl oleate Glyceryl ricinoleate Glyceryl ricinoleate, tocopherol Glyceryl stearate Glyceryl Stearate Citrate Hexamethyldisilazane Hexamethyldisiloxane Hydrogenated Cocoglycerides Hydrogenated palm oil Hydroxytrimethylsilane Isopropoxytrimethylsilane Methylheptyl isostearate Octamethylcyclotetrasiloxane Oleyl erucate Olus Oil ·Organic modified siloxane ·Organic silicone fluid PCA Glyceryl Oleate ·(Caprylic / Capric) PEG-6 Glycerides Phenyltrichlorosilane Poly(dimethylsiloxane) Poly(ethylene glycol)-containing siloxane Polydimethylsiloxane Polyglyceryl-2 Caprate Polyglyceryl-3 Caprate Polyglyceryl-3 diisostearate Polyglyceryl-3 Polyricinoleate Polyglyceryl-4 Cocoate Propylene carbonate Di(caprylic / capric acid) PG Silicone oil Stearalkonium bentonite Stearalkonium hectorite Triheptanoin Trimethyl(bromodifluoromethyl)silane Trimyristin Tristearin Includes.

[0029] (E) Active ingredient Component (E) is a "pharmaceutically active ingredient," preferably an active ingredient selected from any personal active or healthcare active. As used herein, "personal care active" refers to any compound or mixture of compounds known in the art as an additive in personal care formulations, typically added for the treatment of skin, lips, or to provide cosmetic and / or aesthetic benefits. A "healthcare active" refers to any compound or mixture of compounds known in the art to provide a pharmaceutical or medical benefit. Thus, "healthcare active" includes materials commonly used and considered active ingredients or active drug ingredients as defined by the U.S. Department of Health and Human Services, Food and Drug Administration, Title 21, Code of Federal Regulations, Chapter I, Parts 200-299 and 300-499. Thus, a pharmaceutically active ingredient can include any ingredient intended to provide pharmacological activity or other direct effect in the diagnosis, cure, mitigation, treatment, or prevention of disease, or to affect the structure or any function of the human or other animal body. This phrase may include ingredients that may undergo chemical changes in the manufacture of a drug product and that may be present in the drug product in a modified form intended to impart a specified activity or effect.

[0030] Some representative examples of pharmaceutically active ingredients include drugs, vitamins, minerals, hormones, topical antimicrobial agents such as antibiotic active ingredients, antifungal active ingredients for the treatment of athlete's foot, jock itch or ringworm, acne active ingredients, astringent active ingredients, deodorant active ingredients, wart remover active ingredients, corn and callus remover active ingredients, pediculicide active ingredients for the treatment of head, pubic (pubic) and body lice, active ingredients for the control of dandruff, seborrheic dermatitis or psoriasis, and sunburn prevention and treatment agents.

[0031] Pharmaceutically active ingredients useful in the methods of the present invention include vitamins and their derivatives, including "provitamins." Vitamins useful herein include, but are not limited to, vitamin A, retinol, CC esters of retinol, vitamin E, tocopherol, esters of vitamin E, and mixtures thereof. Retinol includes trans-retinol, 1,3-cis-retinol, 11-cis-retinol, 9-cis-retinol, and 3,4-didehydro-retinol, vitamin C and its derivatives, vitamin B, vitamin B provitamin B5, panthenol, vitamin B, vitamin B2, niacin, folic acid, biotin, and pantothenic acid. Other suitable vitamins and INCI names for vitamins considered for inclusion herein are ascorbyl dipalmitate, ascorbyl methylsilanol pectin, ascorbyl palmitate, ascorbyl stearate, ascorbyl glucoside, sodium ascorbyl phosphate, sodium ascorbate, disodium ascorbyl sulfate, potassium (ascorbyl / tocopheryl) phosphate.

[0032] It should be noted that retinol is the International Cosmetic Ingredient Nomenclature (INCI) designated by the Cosmetic and Toiletries Manufacturers Association (CTFA), Washington, D.C., for Vitamin A. Other suitable vitamins and INCI names for vitamins considered for inclusion herein are retinol acetate, retinyl palmitate, retinyl propionate, o-tocopherol, tocophersolan, tocopherol acetate, tocopherol linoleate, tocopherol nicotinate, and tocopherol succinate.

[0033] The pharmaceutically active ingredient used in the method according to the present invention may be an active drug ingredient. Representative examples of some suitable active drug ingredients that may be used include hydrocortisone, ketoprofen, timolol, pilocarpine, adriamycin, mitomycin C, morphine, hydromorphone, diltiazem, theophylline, doxorubicin, daunorubicin, heparin, penicillin G, carbenicillin, cephalothin, cefoxitin, cefotaxime, 5-fluorouracil, cytarabine, 6-azauridine, 6-thioguanine, vinblastine, vincristine, bleomycin sulfate, aurothioglucose, suramin, mebendazole, clonidine, scopolamine, propranolol, phenylpropanolamine hydrochloride, ouabain, atropine, haloperidol, isosorbide, nitroglycerin, ibuprofen, ubiquinone, indomethacin, prostaglandins, naproxen, salbutamol, guanabenzamide, benzodiazepine, benzocaine, benzophenone, benzocaine ... Z), labetalol, pheniramine, metrifonate, and steroids.

[0034] Considered herein to be included as active drug ingredients for the purposes of the present invention are anti-acne agents such as benzoyl peroxide and tretinoin, antibacterial agents such as chlorohexadiene gluconate, antifungal agents such as miconazole nitrate, anti-inflammatory agents, corticosteroids, non-steroidal anti-inflammatory agents such as diclofenac, antipsoriatic agents such as clobetasol propionate, anesthetic agents such as lidocaine, anti-itch agents, anti-dermatitis agents, and agents generally considered to be barrier agents.

[0035] The active ingredient E) of the present invention may be a protein, such as an enzyme. Encapsulating the enzyme in the NIPU elastomer gel has the advantage of preventing the enzyme from inactivating and maintaining its bioactive effect for a longer period of time. Enzymes include, but are not limited to, commercially available, improved, recombinant, wild-type, non-naturally occurring variants, and mixtures thereof. For example, suitable enzymes include hydrolases, cutinases, oxidases, transferases, reductases, hemicellulases, esterases, isomerases, pectinases, lactases, peroxidases, laccases, catalases, and mixtures thereof. Hydrolases include, but are not limited to, proteases (bacterial, fungal, acid, neutral, or alkaline), amylases (alpha or beta), lipases, mannanases, cellulases, collagenases, lysozymes, superoxide dismutases, catalases, and mixtures thereof. Proteases include, but are not limited to, trypsin, chymotrypsin, pepsin, pancreatin, and other mammalian enzymes; papain, bromelain, and other plant enzymes; subtilisin, epidermin, nisin, naringinase (L-rhamnosidase), urokinase, and other bacterial enzymes. Lipases include, but are not limited to, triacylglycerol lipase, monoacylglycerol lipase, lipoprotein lipase, such as steapsin, elepsin, pepsin, and other mammalian, plant, and bacterial lipases, as well as purified versions. Natural papain is preferred as the enzyme. Furthermore, stimulating hormones, such as insulin, can be used with these enzymes to enhance their effectiveness.

[0036] The pharmaceutically active ingredient may also be a sunscreen. The sunscreen may be selected from any sunscreen known in the art that protects the skin from the harmful effects of exposure to sunlight. The sunscreen compound is typically selected from organic compounds, inorganic compounds, or mixtures thereof that absorb ultraviolet (UV) rays. Thus, representative, non-limiting examples that may be used as sunscreens include aminobenzoic acid, cinoxate, diethanolamine methoxycinnamate, digalloyl trioleate, dioxybenzone, ethyl 4-bis(hydroxypropyl)aminobenzoate, glyceryl aminobenzoate, homosalate, lawsone with dihydroxyacetone, menthyl anthranilate, octocrylene, octyl methoxycinnamate, octyl salicylate, oxybenzone, padimate O, phenylbenzimidazole sulfonic acid, red petrolatum, sulisobenzone, titanium dioxide, trolamine salicylate, acetaminosalol, allatoin, PABA, benzalphthalide, benzophenone, benzophenone 1-12, 3-benzylidene camphor, benzylidene camphor hydrolyzed collagen sulfonamide, benzylidene camphor sulfonic acid, benzyl salicylate, bomelone, bumetrizole (b umetriozole), butyl methoxydibenzoylmethane, butyl PABA, ceria / silica, ceria / silica talc, cinoxate, DEA methoxycinnamate, dibenzoxazole naphthalene, di-t-butylhydroxybenzylidene camphor, digalloyl trioleate, diisopropyl methyl cinnamate, dimethyl PABA ethyl cetearyldimonium tosylate, dioctyl butamido triazone, diphenylcarbomethoxyacetoxynaphthopyran, disodium bisethylphenyl thiamin triazine stilbene disulfonate, disodium distyryl biphenyl triaminotriazine stilbene disulfonate, disodium distyryl biphenyl disulfonate, drometrizole, drometrizole trisiloxane, ethyl dihydroxypropyl PABA, ethyl diisopropyl cinnamate, ethyl methoxycinnamate, ethyl PABA, ethyl urocanate, etorocrylene ferulic acid, glyceryl dimethoxycinnamate octanoateGlyceryl PABA, glycol salicylate, homosalate, isoamyl p-methoxycinnamate, isopropyl benzyl salicylate, isopropyl dibenzoylmethane, isopropyl methoxycinnamate, menthyl anthranilate, menthyl salicylate, 4-methylbenzylidene, camphor, octocrylene, octrizole, octyl dimethyl PABA, octyl methoxycinnamate, octyl salicylate, octyl triazone, PABA, PEG-25 PABA, pentyl dimethyl, PABA, phenylbenzimidazole sulfonic acid, polyacrylamidomethylbenzylidene camphor, potassium methoxycinnamate, potassium phenylbenzimidazole sulfonate, red petrolatum, sodium phenylbenzimidazole sulfonate, sodium urocanate, TEA phenylbenzimidazole sulfonate, TEA salicylate, terephthalylidene dicamphor sulfonic acid, titanium dioxide, zinc dioxide, cerium dioxide dioxide), TriPABA, panthenol, urocanic acid, and VA / crotonate / methacryloxybenzophenone-1 copolymer.

[0037] The sunscreen may be a single agent or a combination of two or more agents. Alternatively, the sunscreen is a cinnamate-based organic compound, or alternatively, the sunscreen is octyl methoxycinnamate, such as Uvinul® MC80 (an ester of para-methoxycinnamic acid and 2-ethylhexanol).

[0038] Component (E) may also be a fragrance or flavoring. The flavoring may be any flavoring or fragrance active ingredient commonly used in the flavoring industry. These compositions typically belong to various chemical classes, such as alcohols, aldehydes, ketones, esters, ethers, acetates, nitrites, terpene hydrocarbons, heterocyclic nitrogen- or sulfur-containing compounds, and essential oils of natural or synthetic origin. Many of these flavoring ingredients are described in detail in standard textbooks, such as "Perfume and Flavor Chemicals," 1969, S. Arctander, Montclair, NJ.

[0039] Fragrances may be exemplified by, but are not limited to, perfume ketones and perfume aldehydes. Examples of perfume ketones include buccoxime, isojasmone, methyl beta naphthyl ketone, musk indanone, tonalide / musk plus, alpha damascone, beta damascone, delta damascone, isodamascone, damascenone, damarose, methyl dihydrojasmonate, menthone, carvone, camphor, fenchone, alpha lonone, beta lonone, gamma methyl lonone, fleuramone, dihydrojasmone, cis jasmone, iso-E-super, methyl cedrenyl ketone or methyl cedrylone, acetophenone, methyl acetophenone, para-methoxy acetophenone, methyl beta naphthyl ketone, benzyl acetone, benzophenone, para-hydroxyphenyl butanone, celery ketone, cetearyl ... ketone) or LiveScone, 6-isopropyldecahydro-2-naphthone, dimethyloctenone, Freskomenthe, 4-(1-ethoxyvinyl)-3,3,5,5-tetramethyl-cyclohexanone, methyl-heptenone, 2-(2-(4-methyl-3-cyclohexen-1-yl)propyl)-cyclopentanone, 1-(p-menthen-6(2)-yl)-1-propanone, 4-(4-hydroxy-3-methoxyphenyl)-2-butanone, 2-acetyl -3,3-Dimethylnorbornane, 6,7-dihydro-1,1,2,3,3-pentamethyl-4(5H)-indanone, 4-damascol, Dulcinyl or Cassione, Gelsone, Hexylone, Isocyclone E. Methylcyclocitrone, Methyl Lavender Ketone, Oliven, para-tert-butyl-cyclohexanone, Verdone, Delphone, Muscone, Neobutenone, Plica tone, Veloutone, 2,4,4,7-tetramethyl-oct-6-en-3-one, and Tetrameran.

[0040] More preferably, the perfume ketone is selected from alpha damascone, delta damascone, isodamascone, carvone, gamma-methyl-ionone, iso-E-super, 2.4.4.7-tetramethyl-oct-6-en-3-one, benzylacetone, beta damascone, damascenone, methyl dihydrojasmonate, methyl cedrylone, and mixtures thereof, for their odor properties.

[0041] Preferably, the perfume aldehyde is selected for its odor properties from the following: adoxal, anisaldehyde, thymal, ethyl vanillin, florhydral, helional, heliotropin, hydroxycitronellal, koavone, lauric aldehyde, lyral, methylnonylacetaldehyde, PT bucinal, phenylacetaldehyde, undecylenic aldehyde, vanillin, 2,6,10-trimethyl-9-undecenal, 3-dodecen-1-al, α-n-amylcinnamaldehyde, 4-methoxybenzaldehyde, benzaldehyde, 3-(4-tert-butylphenyl)-propanal, 2-methyl-3-(para-methoxyphenylpropanal, 2-methyl -4-(2,6,6-trimethyl-2(1)-cyclohexen-1-yl)butanal, 3-phenyl-2-propenal, cis- / trans-3,7-dimethyl-2,6-octadien-1-al, 3,7-dimethyl-6-octen-1-al, (3,7-dimethyl-6-octenyl)oxyacetaldehyde, 4-isopropylbenzylaldehyde, 1,2,3,4,5,6,7,8-octahydro-8.8-dimethyl-2-naphthaldehyde, 2,4-dimethyl-3-cyclohexene-1-carboxaldehyde, 2-methyl-3-(isopropylphenyl)propanal, 1-decanal, decyl aldehyde, 2,6-dimethyl-5-heptenal, 4-(tricyclo[5.2.1.0(2,6)-Decylidene-8)-butanal, Octahydro-4,7-methano-1H-indenecarboxaldehyde, 3-ethoxy-4-hydroxybenzaldehyde, para-ethyl-α,α-dimethylhydrocinnamaldehyde, α-methyl-3,4-(methylenedioxy)-hydrocinnamaldehyde, 3,4-methylenedioxybenzaldehyde, α-n-hexylcinnamaldehyde, m-cymene-7-carboxaldehyde, α-methylphenylacetaldehyde, 7-hydroxy-3,7-dimethyloctanal, undecene nal, 2,4,6-trimethyl-3-cyclohexene-1-carboxaldehyde, 4-(3)(4-methyl-3-pentenyl)-3-cyclohexene-carboxaldehyde, 1-dodecanal, 2,4-dimethylcyclohexene-3-carboxaldehyde, 4-(4-hydroxy-4-methylpentyl)-3-cyclohexene-1-carboxaldehyde, 7-methoxy-3,7-dimethyloctan-1-al, 2-methylundecanal, 2-methyldecanal, 1-nonanal, 1-octanal, 2,6,10-trimethyl-5.9-Undecadienal, 2-methyl-3-(4-tertbutyl)propanal, dihydrocinnamaldehyde, 1-methyl-4-(4-methyl-3-pentenyl)-3-cyclohexene-1-carboxaldehyde, 5 or 6-methoxyhexahydro-4,7-methanoindan-1 or 2-carboxaldehyde, 3,7-dimethyloctan-1-al, 1-undecanal, 10-undecen-1-al, 4-hydroxy-3-methoxybenzaldehyde, 1-methyl-3-(4-methylpentyl)-3-cyclohexenecarboxaldehyde xaldehyde), 7-hydroxy-3,7-dimethyloctanal, trans-4-decenal, 2,6-nonadienal, para-tolylacetaldehyde, 4-methylphenylacetaldehyde, 2-methyl-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-butenal, ortho-methoxycinnamaldehyde, 3,5,6-trimethyl-3-cyclohexenecarboxaldehyde, 3,7-dimethyl-2-methylene-6-octenal, phenoxyacetaldehyde, 5,9-dimethyl-4,8-decadienal, peony aldehyde aldehyde)(6,10-dimethyl-3-oxa-5,9-undecadien-1-al), hexahydro-4,7-methanoindan-1-carboxaldehyde, 2-methyloctanal, α-methyl-4-(1-methylethyl)benzeneacetaldehyde, 6,6-dimethyl-2-norpinene-2-propionaldehyde, paramethylphenoxyacetaldehyde, 2-methyl-3-phenyl-2-propen-1-al, 3,5,5-trimethylhexanal, hexahydro-8,8-dimethyl-2-naphthaldehyde, 3-propyl-bicyclo[2.2.It is selected from 1-hept-5-ene-2-carbaldehyde, 9-decenal, 3-methyl-5-phenyl-1-pentanal, methylnonylacetaldehyde, hexanal, trans-2-hexenal, 1-p-menthene-q-carboxaldehyde and mixtures thereof. More preferred aldehydes, due to their odor characteristics, are selected from 1-decanal, benzaldehyde, furohydral, 2,4-dimethyl-3-cyclohexene-1-carboxaldehyde, cis / trans-3,7-dimethyl-2,6-octadien-1-al, heliotropin, 2,4,6-trimethyl-3-cyclohexene-1-carboxaldehyde, 2,6-nonadienal, α-amyl-cinnamaldehyde, α-n-hexyl-cinnamaldehyde, PT bucinal, lyral, thymal, methylnonylacetaldehyde, hexanal, trans-2-hexenal, and mixtures thereof. Among the above list of perfume ingredients, some are trade names known to those skilled in the art and include isomers. Such isomers are also suitable for use in the present invention.

[0042] Component (E) may also be one or more plant extracts. Examples of these ingredients are as follows: Angelica extract, avocado extract, hydrangea extract, althaea extract, arnica extract, aloe extract, apricot extract, apricot kernel extract, ginkgo biloba extract, fennel extract, turmeric curcuma extract, oolong tea extract, star anise extract, echinacea extract, scutellaria root extract, phellodendron bark extract, coptis chinensis extract, barley extract, hypericum extract, white nettle extract, watercress extract, orange extract, dried seawater, seaweed extract, hydrolyzed elastin, hydrolyzed wheat flour, hydrolyzed silk, chamomile extract, carrot extract, mugwort extract, licorice extract, hibiscus tea extract, pyracantha fortuneana extract, Fortuneana fruit extract, kiwi extract, cinchona extract, cucumber extract, guanosine, gardenia extract, kumazasa extract, kudzu extract, walnut extract, grapefruit extract, clematis extract, chlorella extract, mulberry extract, gentian extract, black tea extract, yeast extract, burdock extract, fermented rice bran extract, rice germ oil, comfrey extract, collagen, bilberry extract, gardenia extract, Chinese cabbage extract, Bupleurum extract, umbilical cord extract, salvia extract, saponaria extract, bamboo extract, hawthorn extract, Japanese pepper extract, shiitake mushroom extract, rehmannia root extract, purple extract, perilla extract, linden extract, meadowsweet extract, peony extract, calamus root extract, white birch extract, horsetail extract, ivy extract, hawthorn extract, Sambucus nigra migra extract, yarrow (Achillea millefolium) extract, peppermint (Mentha piperita) extract, sage extract, mallow extract, cnidium officinale root extract, Japanese green swertia extract, soybean extract, jujube extract, thyme extract, tea extract, clove extract, grass grass (Gramineae imperata)cyrillo extract, Satsuma mandarin peel extract, Angelica acutiloba extract, Calendula extract, Peach kernel extract, Spruce extract, Houttuyna cordata extract, Tomato extract, Natto extract, Ginseng extract, Green tea extract (Camellia sine sis), Garlic extract, Wild rose extract, Hibiscus extract, Bakumondo extract, Lotus (Nelumbo nucifera) extract, Parsley extract, Honey, Witch hazel extract, Cinnamal extract, Japanese laurel extract, Bisabolol extract, Loquat extract, Dandelion extract, Butterbur extract, Japanese holly extract, Butterbur extract, Grape extract, Propolis extract, Loofah (lufa) extract, Safflower extract, Peppermint extract, Tilia extract, Peony extract, Hop extract, Pine extract, Horse chestnut extract, Skunk cabbage (Lysichiton camtschatcese) extract, soapberry peel extract, common mint extract, peach extract, cornflower extract, eucalyptus extract, saxifrage extract, citron extract, Job's tears extract, mugwort extract, lavender extract, apple extract, lettuce extract, lemon extract, astragalus extract, rose extract, rosemary extract, Roman chamomile extract, and royal jelly extract.

[0043] The amount of component (E) present in the NIPU gel composition can vary, but is typically in the following range: 0.05 to 50 weight percent, alternatively 1 to 25 weight percent, or alternatively 1 to 10 weight percent, based on the weight of the NIPU elastomer present in the composition, i.e., the total weight of components (A), (B), (C), and (D) in the NIPU gel composition.

[0044] The active ingredient (E) may be added to the NIPU gel composition during the manufacture of the NIPU elastomer (pre-dosing method) or may be added after the formation of the NIPU elastomer gel (post-dosing method).

[0045] The pre-injection method is I) The following A) cyclic or aliphatic carbonate polymers (which may optionally contain siloxane in their backbones); B) Aliphatic or cycloaliphatic polyamines; C) optionally a reaction catalyst; D) optionally a carrier fluid, wherein the locally acceptable carrier fluid is a reaction solvent or the carrier fluid is added after elastomer formation, optionally the carrier fluid comprises a locally acceptable carrier fluid; E) personal care or healthcare active ingredients together with NIPU elastomer gel; to form an active ingredient-containing NIPU elastomer gel.

[0046] The post-injection method is I) The following A) cyclic or aliphatic carbonate polymers (which may optionally contain siloxane in their backbones); B) Aliphatic or cycloaliphatic polyamines; C) optionally a reaction catalyst; D) optionally a carrier fluid, wherein the locally acceptable carrier fluid is a reaction solvent or the carrier fluid is added after elastomer formation, optionally the carrier fluid comprises a locally acceptable carrier fluid; Mixing the II) shearing the NIPU elastomer gel into a smooth paste; and III) The following E) Personal Care or Healthcare Active Ingredients with a NIPU elastomer gel to form a NIPU elastomer gel containing the active ingredient. The personal care active ingredient may be mixed as a component of a separate mixture with one or more excipients.

[0047] NIPU elastomer The NIPU elastomers of the present invention can be obtained as the NIPU reaction product of components (A), (B), and (C) in (D). The term "NIPU reaction" refers to the addition of a compound containing multiple cyclic or acyclic carbonate groups (e.g., component A) to a compound containing multiple primary or secondary amine groups (e.g., component B), optionally in the presence of a catalyst (e.g., component C). Here, the molar ratio of carbonate to amine groups is 1 / 1. Alternatively, this ratio can range from 8 / 1 to 0.9 / 1. The NIPU reaction is carried out in the presence of a solvent, which is the same as the carrier fluid described as component (D), and can optionally be used without further purification.

[0048] Method for measuring the hardness of NIPU elastomer gel compositions The NIPU elastomer is prepared in a carrier fluid (described above as component D) to form a gelled composition. The gelled compositions of the present invention can be characterized by their hardness or firmness. Useful tests for characterizing gels are those recommended by the Gelatin Manufacturers Institute of America, such as the use of a "Texture Analyzer" (Model TAXT2, Stable Micro Systems, Inc., Godalming, UK). Gel samples are subjected to a compression test using a texture analyzer equipped with a probe with a 5.0 kg load cell. The probe approaches the surface of the gel at a rate of 1 mm / sec and continues to compress the gel for a distance of 5.0 mm. The texture analyzer detects the resistance force experienced by the probe during the compression test. The load cell force is plotted as a function of time. For purposes of this invention, the hardness of NIPU elastomers, gels, and elastomer blends (SEBs) is defined as the resistance force detected by the "Texture Analyzer" probe during the compression test. Hardness is characterized as the force at the point of maximum compression (i.e., 5.0 mm compression into the gel surface). Each gel was typically tested an average of three times, and gels were prepared in triplicate.

[0049] The resulting force (grams) value is converted to Newtons (N) by dividing by 101.97 (i.e., 1 Newton equals 101.97 grams force, based on the size of the probe used). The second property reported from a Texture Analyzer measurement is Area FT 1:2 (gram force·seconds), which is the area integral of the force-test time curve. This property, associated with elastomers and gels, indicates the ability to maintain resistance to compressive forces and is therefore indicative of the gel network. Values are reported in grams force·seconds (g force.sec) and are converted to the SI unit of Newton seconds (Newton.sec) by dividing the force.sec value by 101.97.

[0050] The NIPU gel of the present invention has a resistance of at least 0.5 Newtons / cm when measured with a 1.27 cm diameter spherical probe and a 50 g sample of the gel placed in a 4 oz round glass jar. 2 , or 1 Newton / cm 2 , or alternatively 2 Newtons / cm 2 It has a compressive hardness of .

[0051] NIPU elastomer-containing gel paste composition Using the gelling composition of the present invention, I) shearing the NIPU elastomer gel as described below; II) Add the sheared NIPU elastomer gel to an additional amount of D) a carrier fluid as described above, and optionally E) mixing with a personal care or health care active ingredient to form a gel paste or blend composition; A gel paste or gel blend composition containing the active ingredient can be prepared by the process described above. The personal care active ingredient may also be mixed as a component of a separate mixture with one or more excipients.

[0052] The NIPU elastomer gel compositions of the present invention can be viewed as discrete crosslinked NIPU elastomer gel particles dispersed in a carrier fluid. As such, the NIPU elastomer compositions are effective rheological thickeners for compatible low molecular weight solvents. As such, they can be used to prepare useful gel blend compositions, such as "gel paste" compositions.

[0053] To produce such NIPU elastomer gel pastes, the NIPU elastomer gel of a known initial elastomer content (IEC) is sheared to obtain a reduced particle size and then further diluted to a final elastomer content (FEC). As used herein, shearing refers to any shear mixing process, such as homogenization, sonolating, or other mixing processes known in the art as shear mixing. Shear mixing of the NIPU elastomer gel composition results in a composition with reduced particle size. The composition with reduced particle size is then further mixed with D) a carrier fluid. The carrier fluid can be any carrier fluid as described above, but is typically a linear ester (e.g., heptyl undecylenate), a triglyceride (e.g., triheptanoin), or an alkane (e.g., isododecane). The technique for combining the D) carrier fluid with the NIPU elastomer composition with reduced particle size is not critical and typically involves simple stirring or mixing. The resulting composition can be considered a paste, having a viscosity greater than 100,000 cP (mPas).

[0054] Method for measuring viscosity of NIPU elastomer gel paste When used with a suitable Brookfield viscometer equipped with a special T-bar spindle, the Brookfield HELIPATH™ stand allows viscosity / consistency measurements in centipoise for materials with properties similar to pastes, putties, creams, gelatin, or wax. The viscosity of the NIPU elastomer blend was determined using a Brookfield Model DV-II+ Pro viscometer equipped with a HELIPATH™ stand (Brookfield Model D) and a T-bar spindle (Brookfield HELIPATH™ spindle set). All were purchased from Brookfield Engineering Laboratories, Inc. (11 Commerce Boulevard, Middleboro, Mass., USA). A sample size of 50 g in a 4-ounce round jar was required. Prior to measurement, the following preparation procedure was used: air bubbles were first removed from the sample by centrifugation, followed by 2 hours under vacuum. After degassing, the sample was conditioned at 25°C for a minimum of 4 hours. Measurements were performed according to the typical procedure for the HELIPATH™ spindle. Typically, spindle 93 (T-bar spindle E) was used, with a standard setting of 6.5 rpm. The spindle speed was kept constant at 6.5 rpm.

[0055] Also provided herein are topical formulations comprising gel compositions or gel pastes. In such formulations, the gel compositions or gel pastes are preferably used as thickeners or stabilizers for the topical formulations. Other components of topical formulations are known in the art and may include, for example, various ingredients such as emulsion stabilizers, emulsifiers, skin conditioners, suspending agents, etc. The amount of these additional ingredients may be on the order of about 0.01% to about 50% by weight.

[0056] As used herein, "emulsion stabilizer" refers to a composition that helps prevent an emulsion from separating into its oily and aqueous components. In embodiments, the emulsion stabilizer utilized in the formulations described herein is a naturally occurring gum or modified gum or a natural mineral. Exemplary emulsion stabilizers include, but are not limited to, acacia, cellulose, crystalline cellulose, gellan, guar, locust bean, xanthan, magnesium aluminum silicate, bentonite, or hectorite clay, and the like, including combinations thereof.

[0057] As used herein, "skin conditioner" refers to a composition that acts as a lubricant on the surface of the skin or increases the moisture content of the surface of the skin. Exemplary skin conditioners for use in the formulation include, but are not limited to, adipates, alkyl benzoates, C8 or higher fatty acid esters, esterified erucates, laurates, neopentanoates, salicylates, stearates, triglycerides, carbonates, glycols, glycerin, mineral oils, and the like, including combinations thereof.

[0058] As used herein, "emulsifier" refers to a composition that aids in the formation of an oil-in-water or water-in-oil emulsion. Exemplary emulsifiers for use in the formulation include, but are not limited to, polysorbates, ethoxylated fatty acids, fatty acids neutralized with sodium hydroxide, potassium hydroxide, or amines, substituted glucosides, sodium lauryl and lauryl ether sulfates, ethoxylated esters, lecithin and lecithin derivatives, and the like, including combinations thereof.

[0059] As used herein, "suspending agent" refers to a composition that modifies the interface between solid particles and a liquid medium to improve the resistance of the particles to coming together and falling out of solution. Exemplary suspending agents for use in the formulation include, but are not limited to, hydroxystearic acid, polyhydroxystearic acid, sodium polyacrylate polymers, methyl methacrylate crosspolymers, and the like, including combinations thereof.

[0060] In additional embodiments, non-isocyanate polyurethane (NIPU) elastomers may be utilized in solid-based form, such as in foot-conforming shoe inserts or shoe soles.

[0061] Non-isocyanate polyurethane (NIPU) elastomers can also be used as medically acceptable gels, including for example, medical implants or portions of implants, including as cartilage replacements, bone replacements, etc.

[0062] Exemplary Embodiments Embodiment 1: Formula I: [ka] (In the formula, n is 2 to m; A is a terminal group selected from cyclocarbonate and amine; B is [ka] and -(CH2) x -C(OH)R 5 -Selected from; x is 0 to 4; R 1 is C1~C 30a substituted or unsubstituted straight or branched chain aliphatic, alicyclic, aryl, heteroalicyclic, or heteroaryl group, optionally containing heteroatoms; R 2 , R 4 , and R 5 are independently hydrogen or C1 to C 30 a substituted or unsubstituted straight or branched chain alkyl group, aliphatic group, alicyclic group, or aryl group, optionally containing heteroatoms; R 3 is C1~C 30 a substituted or unsubstituted straight or branched chain aliphatic, alicyclic, aryl, heteroalicyclic, or heteroaryl group, optionally containing heteroatoms; D is a terminal group selected from cyclocarbonate and amine; m is an integer between 3 and 1,000,000,000,000, including 0, 100, 1,000, 10,000, 100,000, 1,000,000, 10,000,000, 100,000,000, 1,000,000,000, 10,000,000,000, 100,000,000,000 and 1,000,000,000,000, and other values between 3 and 1,000,000,000,000. Non-isocyanate polyurethane (NIPU) elastomer.

[0063] Embodiment 2: A) Polycarbonates or mixtures of polycarbonates containing two or more carbonate functional groups; B) a polyamine or mixture of polyamines containing two or more amine functional groups, wherein the amine functional groups are either primary or secondary; C) optionally a NIPU reaction catalyst; and D) optionally a topically acceptable carrier fluid, wherein said topically acceptable carrier fluid is a reaction solvent or said topically acceptable carrier fluid is added after elastomer formation in a concentration of 50% (w / w) to 99.9% (w / w) of the gel composition; A gel composition comprising a non-isocyanate polyurethane (NIPU) elastomer prepared from the reaction of:

[0064] Embodiment 3: 3. The gel composition of embodiment 2, wherein the topically acceptable carrier fluid is selected from the group consisting of esters, triglycerides, hydrocarbons, silicone fluids, and combinations thereof.

[0065] Embodiment 4: 3. The gel composition of embodiment 2, wherein the topically acceptable carrier fluid is selected from the group consisting of diisooctyl succinate, heptyl undecylenate, neopentyl glycol diheptanoate, and coco caprylate.

[0066] Embodiment 5: 3. The gel composition of embodiment 2, further comprising a pharmaceutically active ingredient dissolved in the topically acceptable carrier fluid.

[0067] Embodiment 6: 3. The gel composition of embodiment 2, further comprising a pharmaceutically active ingredient incorporated into the gel.

[0068] Embodiment 7: 3. The gel composition of embodiment 2, wherein the polycarbonate or mixture of polycarbonates is a low molecular weight polycarbonate or mixture of polycarbonates containing two or more hydroxyl groups, and the polyamine or mixture of polyamines is a low molecular weight polyamine or mixture of polyamines containing two or more primary or secondary amines.

[0069] Embodiment 8: 1. A method for producing a non-isocyanate polyurethane (NIPU) elastomer gel, comprising: i) combining a polycarbonate reactant with a polyamine reactant, wherein the polycarbonate contains two or more carbonate functional groups and the polyamine contains two or more primary or secondary amines; and ii) optionally adding a locally acceptable carrier fluid, wherein said locally acceptable carrier fluid is a reaction solvent or said locally acceptable carrier fluid is added after elastomer formation to form a polymer gel mixture having a polymer concentration of about 80% (w / w); and iii) optionally adding a NIPU reaction catalyst; and iv) Optionally, heating the reaction mixture to about 100°C to form the NIPU elastomer. A method comprising:

[0070] Embodiment 9: 9. The method of embodiment 8, wherein said topically acceptable carrier fluid is selected from the group consisting of esters, triglycerides, hydrocarbons, silicone fluids, and combinations thereof.

[0071] Embodiment 10: 9. The method of embodiment 8, wherein said topically acceptable carrier fluid is selected from the group consisting of diisooctyl succinate, heptyl undecylenate, neopentyl glycol diheptanoate, and cococaprylate.

[0072] Embodiment 11: 9. The method of embodiment 8, further comprising dissolving a pharmaceutically active ingredient in said topically acceptable carrier fluid.

[0073] Embodiment 12: 9. The method of embodiment 8, wherein the polycarbonate reactant comprises two or more hydroxyl groups.

[0074] Embodiment 13: 9. The method of embodiment 8, further comprising preparing the polycarbonate reactant from a vegetable oil or mixture of vegetable oils containing two or more hydroxyl groups.

[0075] Embodiment 14: 9. The method of embodiment 8, further comprising preparing the polycarbonate reactant from a copolymer of dilinoleic acid or a mixture of copolymers of dilinoleic acid.

[0076] Embodiment 15: 1. A method for producing a NIPU elastomer gel paste, comprising: i) shearing the NIPU elastomer of claim 8; ii) optionally adding an additional amount of a topically acceptable carrier fluid during shearing to produce a gel paste composition; and iii) optionally adding a pharmaceutically active ingredient; A method comprising:

[0077] Embodiment 16: 16. A NIPU elastomer gel paste prepared according to the embodiment of claim 15.

[0078] Embodiment 17: A topical formulation comprising the gel composition of embodiment 5 or embodiment 6, wherein the pharmaceutically active ingredient is a personal care active or a healthcare active.

[0079] Embodiment 18: A topical formulation comprising the NIPU elastomer gel paste of embodiment 15, comprising a personal care or healthcare active.

[0080] Embodiment 19: A) Polycarbonates or mixtures of polycarbonates containing two or more carbonate functional groups; B) a polyamine or mixture of polyamines containing two or more amine functional groups, wherein the amine functional groups are either primary or secondary; C) optionally a NIPU reaction catalyst; and D) a carrier fluid, wherein said carrier fluid is a reaction solvent or said carrier fluid is added after elastomer formation at a concentration of 60% (w / w) to 99.9% (w / w) of said gel composition.

[0081] Embodiment 20: 20. A foot-conforming shoe insole or sole comprising the non-isocyanate polyurethane (NIPU) elastomer of embodiment 1 or the gel composition of embodiment 19.

[0082] Embodiment 21: 20. A medically acceptable gel comprising the non-isocyanate polyurethane elastomer (NIPU) of embodiment 1 or the gel composition of embodiment 19.

[0083] Embodiment 22: A topical formulation comprising the NIPU elastomer of embodiment 1.

[0084] Embodiment 23: 10. A gel composition comprising the non-isocyanate polyurethane (NIPU) elastomer of embodiment 1 and a topically acceptable carrier fluid in a concentration of 60% (w / w) to 99.9% (w / w) of the gel composition.

[0085] Embodiment 24: 1. A method for producing a NIPU elastomer gel paste, comprising: i) shearing the gel paste of embodiment 23; ii) optionally adding an additional amount of a topically acceptable carrier fluid during shearing to produce a gel paste composition; and iii) optionally adding a pharmaceutically active ingredient; A method comprising:

[0086] Embodiment 25: 25. A NIPU elastomer gel paste prepared by the method of embodiment 24.

[0087] Embodiment 26: A topical formulation comprising the gel composition of embodiment 24 or the NIPU elastomer gel paste of embodiment 25. [Example]

[0088] Example 1 - Preparation of Castor Oil / Isophorone Diamine NIPU Elastomer.

[0089] A topically acceptable carrier fluid capable of dissolving castor oil, such as diisooctyl succinate (400 grams), castor oil (71.1 grams) with a hydroxyl value of 166.87 mg / g, and dimethyl carbonate (20.97 grams, 1.1 equivalents per mole of hydroxyl groups) are added to a stainless steel or glass reaction vessel. The reaction mixture is stirred at temperatures between 25°C and approximately 100°C for up to 8 hours, after which isophoronediamine (36.08 grams) is added with stirring. Once a homogeneous mixture is obtained, 50 grams of the mixture is poured into a 4-ounce glass jar. The 50 g sample is covered with the remainder of the reaction mixture and heated to 75°C for up to approximately 23 hours, at which point a translucent gel forms. The hardness of the 50 g gel sample, measured using a Stable Micro Systems Texture Analyzer (equipped with a 5 kg load cell and fitted with a TA-18B Stable Micro Systems probe inserted 5 mm into the gel surface), is approximately 0.87 N / cm. 2 It is expected to be.

[0090] The NIPU elastomer gel is broken into smaller pieces, placed in a metal container, and a topically acceptable carrier fluid, which may or may not be heptyl undecylenate, is added, followed by homogenization using a Silverson L5M-A homogenizer (with a 30 mm diameter rotor and a Square Hole High Shear Screen) operating at 4500-8000 rpm to obtain a smooth gel paste with the desired viscosity.

[0091] Example 2 - Preparation of Castor Oil / Hexemethylenediamine NIPU Elastomer.

[0092] A topically acceptable carrier fluid capable of dissolving castor oil, such as diisooctyl succinate (400 grams), castor oil (71.1 grams) with a hydroxyl number of 166.87 mg / g, and dimethyl carbonate (20.97 grams, 1.1 equivalents per mole of hydroxyl groups) are added to a stainless steel or glass reaction vessel. The reaction mixture is stirred at approximately 75°C for up to 8 hours, after which hexamethylenediamine (24.62 grams) is added with stirring. Once a homogeneous mixture is obtained, 50 grams of the mixture is poured into a 4-ounce glass jar. The 50 g sample is covered with the remainder of the reaction mixture and heated to 75°C for up to 23 hours, at which point a translucent gel forms. The hardness of the 50 g gel sample, measured using a Stable Micro Systems Texture Analyzer (equipped with a 5 kg load cell and fitted with a TA-18B Stable Micro Systems probe inserted 5 mm into the gel surface), is approximately 0.87 N / cm. 2 It is expected to be.

[0093] The NIPU elastomer gel is broken into smaller pieces, placed in a metal container, and a topically acceptable carrier fluid, which may or may not be heptyl undecylenate, is added, followed by homogenization using a Silverson L5M-A homogenizer (with a 30 mm diameter rotor and a Square Hole High Shear Screen) operating at 4500-8000 rpm to obtain a smooth gel paste with the desired viscosity.

[0094] Example 3 - Preparation of Castor Oil / Diamine NIPU Elastomer. A topically acceptable carrier fluid capable of dissolving castor oil, such as diisooctyl succinate (400 grams), castor oil (71.1 grams) with a hydroxyl value of 166.87 mg / g, and dimethyl carbonate (20.97 grams, 1.1 equivalents per mole of hydroxyl groups) are added to a stainless steel or glass reaction vessel. The reaction mixture is stirred at temperatures between 25°C and approximately 100°C for up to 8 hours, after which the diamine is added with stirring. Once a homogeneous mixture is obtained, 50 grams of the mixture is poured into a 4-ounce glass jar. The 50 g sample is covered with the remainder of the reaction mixture and heated to 75°C for up to 23 hours, at which point a translucent gel is formed. The hardness of the 50 g gel sample, measured using a Stable Micro Systems Texture Analyzer (equipped with a 5 kg load cell and fitted with a TA-18B Stable Micro Systems probe inserted 5 mm into the gel surface), is approximately 0.87 N / cm. 2 It is expected to be.

[0095] The NIPU elastomer gel is broken into smaller pieces, placed in a metal container, and a topically acceptable carrier fluid, which may or may not be heptyl undecylenate, is added, followed by homogenization using a Silverson L5M-A homogenizer (with a 30 mm diameter rotor and a Square Hole High Shear Screen) operating at 4500-8000 rpm to obtain a smooth gel paste with the desired viscosity.

[0096] Example 4 - Preparation of Castor Oil / Triamine NIPU Elastomer Gel. A topically acceptable carrier fluid capable of dissolving castor oil, such as diisooctyl succinate (400 grams), castor oil (71.1 grams) with a hydroxyl value of 166.87 mg / g, and dimethyl carbonate (20.97 grams, 1.1 equivalents per mole of hydroxyl groups) are added to a stainless steel or glass reaction vessel. The reaction mixture is stirred at temperatures between 25°C and approximately 100°C for up to 8 hours, after which the triamine is added with stirring. Once a homogeneous mixture is obtained, 50 grams of the mixture is poured into a 4-ounce glass jar. The 50 g sample is covered with the remainder of the reaction mixture and heated to 75°C for up to approximately 23 hours, at which point a translucent gel is formed. The hardness of the 50 g gel sample, measured using a Stable Micro Systems Texture Analyzer (equipped with a 5 kg load cell and fitted with a TA-18B Stable Micro Systems probe inserted 5 mm into the gel surface), is approximately 0.87 N / cm. 2 It is expected to be.

[0097] The NIPU elastomer gel is broken into smaller pieces, placed in a metal container, and a topically acceptable carrier fluid, which may or may not be heptyl undecylenate, is added, followed by homogenization using a Silverson L5M-A homogenizer (with a 30 mm diameter rotor and a Square Hole High Shear Screen) operating at 4500-8000 rpm to obtain a smooth gel paste with the desired viscosity.

[0098] Example 5 - Preparation of Dilinoleic Acid / Propanediol Copolymer Diamine NIPU Elastomer Gel. A topically acceptable carrier fluid capable of dissolving dilinoleic acid / propanediol copolymer, such as triheptanoin (up to approximately 400 grams), and dimethyl carbonate (1.1 equivalents per mole of hydroxyl groups) are added to a stainless steel or glass reaction vessel. The reaction mixture is stirred at temperatures between 25°C and approximately 100°C for up to 8 hours, after which the diamine is added with stirring. Once a homogeneous mixture is obtained, 50 grams of the mixture is poured into a 4-ounce glass jar. The 50 g sample is covered with the remainder of the reaction mixture and heated to 75°C for up to approximately 23 hours, at which point a translucent gel forms. The hardness of a 50 g gel sample, measured using a Stable Micro Systems Texture Analyzer (equipped with a 5 kg load cell and fitted with a TA-18B Stable Micro Systems probe inserted 5 mm into the gel surface), is approximately 0.87 N / cm. 2 It is expected to be.

[0099] The NIPU elastomer gel is broken into smaller pieces, placed in a metal container, and a topically acceptable carrier fluid, which may or may not be heptyl undecylenate, is added, followed by homogenization using a Silverson L5M-A homogenizer (with a 30 mm diameter rotor and a Square Hole High Shear Screen) operating at 4500-8000 rpm to obtain a smooth gel paste with the desired viscosity.

[0100] Example 6 - Preparation of Dilinoleic Acid / Dilinolediol Copolymer Diamine NIPU Elastomer Gel. A topically acceptable carrier fluid capable of dissolving the dilinoleic acid / propanediol copolymer, such as triheptanoin (up to approximately 400 grams), and dimethyl carbonate (1.1 equivalents per mole of hydroxyl groups in the diol copolymer) are added to a stainless steel or glass reaction vessel. The reaction mixture is stirred at temperatures between 25°C and approximately 100°C for up to 8 hours, after which the diamine is added with stirring. Once a homogeneous mixture is obtained, 50 grams of the mixture is poured into a 4-ounce glass jar. The 50 g sample is covered with the remainder of the reaction mixture and heated to 75°C for up to approximately 23 hours, at which point a translucent gel is formed. The hardness of the 50 g gel sample, measured using a Stable Micro Systems Texture Analyzer (equipped with a 5 kg load cell and fitted with a TA-18B Stable Micro Systems probe inserted 5 mm into the gel surface), is approximately 0.87 N / cm. 2 It is expected to be.

[0101] The NIPU elastomer gel is broken into smaller pieces, placed in a metal container, and a topically acceptable carrier fluid, which may or may not be heptyl undecylenate, is added, followed by homogenization using a Silverson L5M-A homogenizer (with a 30 mm diameter rotor and a Square Hole High Shear Screen) operating at 4500-8000 rpm to obtain a smooth gel paste with the desired viscosity.

[0102] Example 7 - Preparation of serum containing NIPU elastomer. 700 g of the NIPU elastomer gel from one of Examples 1-6 was added to a stainless steel reaction vessel equipped with an overhead stirrer. Up to 300 g of argan oil was added to the gel, and the mixture was stirred with or without heat for up to 1 hour to obtain the argan serum.

[0103] Example 8 - Preparation of oil-in-water emulsion using NIPU elastomer Oil-in-water emulsions can be formed by adding a topically acceptable oil to the water phase while gently heating to 75°C. After cooling to room temperature, NIPU elastomer can be post-added at concentrations between 5-90% to obtain an elegant cream.

[0104] Example 9 - Preparation of a sunscreen composition containing castor oil / isophorone diamine NIPU elastomer. Avobenzone (30 g; 3% w / w) + octocrylene (100 g; 10% w / w) + homosalate (150 g; 15% w / w) + octyl salicylate (50 g; 5% w / w) + Sunboost (50 g; 5% w / w; Kobo) + Halbrite (50 g; 5% w / w; Hallstar), Vegelight (270 g; 27% w / w) and castor oil / isophorone diamine NIPU elastomer gel paste (300 g; 30% w / w) are added to a stainless steel container and mixed for 20 minutes using an overhead mixer equipped with a paddle blade to obtain a homogeneous sunscreen formulation.

[0105] Example 10 - Preparation of Dilinoldiol / Polyoxypropylenetriamine NIPU Elastomer. To a 4 oz. glass jar was added dilinoldiol dimethyl dicarbonate (25.0 g) (previously synthesized by the reaction of dilinoldiol with dimethyl carbonate) and Jeffamine T-403 (12.65 g; Huntsman International LLC, The Woodlands, TX). The reaction mixture was stirred at room temperature until homogeneous, at which point triazabicyclodecene (753 mg) was added. The clear, colorless reaction mixture was heated to 120°C overnight to yield a slightly colored, clear, non-pourable elastomeric rubber. The hardness of this elastomeric rubber, measured using a Stable Micro Systems Texture Analyzer (equipped with a 5 kg load cell and fitted with a TA-18B Stable Micro Systems probe inserted 5 mm into the gel surface), was 180 N / cm. 2 It was.

[0106] Example 11 - Preparation of Castor Oil / Isophorone Diamine NIPU Elastomer To a test tube was added castor oil carbonate (500 mg), previously synthesized by the reaction of castor oil with dimethyl carbonate, and isophoronediamine (247 mg). The reaction mixture was vortexed at room temperature until homogeneous, at which point triazabicyclodecene (12.47 mg) was added. The reaction mixture was heated to 120°C in a heat block and vortexed to ensure a homogeneous mixture. The reaction mixture was heated at 120°C overnight, resulting in a slightly non-flowable elastomeric rubber. The hardness of this elastomeric rubber, measured using a Stable Micro Systems Texture Analyzer (equipped with a 5 kg load cell and fitted with a TA-18B Stable Micro Systems probe inserted 5 mm into the gel surface), was 250 N / cm. 2 It was.

[0107] Example 12 - Preparation of Dilinol Diol / Polyoxypropylene Triamine NIPU Elastomer Gel Paste The dilinol diol / polyoxypropylene triamine NIPU elastomer of Example 10 was crushed into small pieces using hand tools, and 24.65 g of the elastomer solids were added to a stainless steel reaction vessel, followed by 24.65 g of diisooctyl succinate. The slurry was mixed for 5 minutes using a Silverson L5M-A homogenizer (with a 30 mm diameter rotor and a square-hole high-shear screen) operating at 5,000 rpm and then homogenized to obtain a smooth gel paste. The viscosity of the resulting smooth gel was measured to be 62,333 cps using a Brookfield Model D Helipath stand and a Brookfield Model DV-II+Pro Viscometer with a TC spindle. Measurements were performed according to the typical procedure for the Helipath spindle, with a constant spindle speed maintained at 6.5 rpm and a torque of 37.4%.

Claims

1. Formula I: 【Chemical 1】 (In the formula, n is from 2 to 100,000; A is a terminal group selected from cyclocarbonate and amine; B is 【Chemistry 2】 and -(CH 2 ) x -C(OH)R 5 - selected from; x is 0 to 4; R 1 is C 1 ~C 30 a substituted or unsubstituted straight or branched chain aliphatic, alicyclic, aryl, heteroalicyclic, or heteroaryl group, optionally containing heteroatoms; R 2 , R 4 , and R 5 are independently hydrogen or C 1 ~C 30 a substituted or unsubstituted straight or branched chain alkyl, aliphatic, alicyclic, or aryl group, optionally containing heteroatoms; R 3 is C 1 ~C 30 a substituted or unsubstituted straight or branched chain aliphatic, alicyclic, aryl, heteroalicyclic, or heteroaryl group, optionally containing heteroatoms; D is a terminal group selected from cyclocarbonate and amine. Non-isocyanate polyurethane (NIPU) elastomer.

2. A) polycarbonates or mixtures of polycarbonates containing two or more carbonate functional groups; B) a polyamine or mixture of polyamines containing two or more amine functional groups, wherein the amine functional groups are either primary or secondary; C) optionally a NIPU reaction catalyst; and D) optionally a topically acceptable carrier fluid, wherein said topically acceptable carrier fluid is a reaction solvent or said topically acceptable carrier fluid is added after elastomer formation in a concentration of 50% (w / w) to 99.9% (w / w) of the gel composition; A gel composition comprising a non-isocyanate polyurethane (NIPU) elastomer prepared from the reaction of:

3. 3. The gel composition of claim 2, wherein the topically acceptable carrier fluid is selected from the group consisting of esters, triglycerides, hydrocarbons, silicone fluids, and combinations thereof.

4. 3. The gel composition of claim 2, wherein the topically acceptable carrier fluid is selected from the group consisting of diisooctyl succinate, heptyl undecylenate, neopentyl glycol diheptanoate, and cococaprylate.

5. 3. The gel composition of claim 2, further comprising a pharmaceutically active ingredient dissolved in the topically acceptable carrier fluid.

6. 3. The gel composition of claim 2, further comprising a pharmaceutically active ingredient incorporated into the gel.

7. 3. The gel composition of claim 2, wherein the polycarbonate or mixture of polycarbonates is a low molecular weight polycarbonate or mixture of polycarbonates containing two or more hydroxyl groups, and the polyamine or mixture of polyamines is a low molecular weight polyamine or mixture of polyamines containing two or more primary or secondary amines.

8. 1. A method for producing a non-isocyanate polyurethane (NIPU) elastomer, comprising: i) combining a polycarbonate reactant with a polyamine reactant, wherein the polycarbonate contains two or more carbonate functional groups and the polyamine contains two or more primary or secondary amines; and ii) optionally adding a locally acceptable carrier fluid, wherein said locally acceptable carrier fluid is a reaction solvent or said locally acceptable carrier fluid is added after elastomer formation to form a polymer gel mixture having a polymer concentration of about 80% (w / w); iii) optionally adding a NIPU reaction catalyst; and iv) Optionally, heating the reaction mixture to about 100°C to form the NIPU elastomer. A method comprising:

9. 9. The method of claim 8, wherein the topically acceptable carrier fluid is selected from the group consisting of esters, triglycerides, hydrocarbons, silicone fluids, and combinations thereof.

10. 9. The method of claim 8, wherein the topically acceptable carrier fluid is selected from the group consisting of diisooctyl succinate, heptyl undecylenate, neopentyl glycol diheptanoate, and cococaprylate.

11. 10. The method of claim 8, further comprising dissolving a pharmaceutically active ingredient in the topically acceptable carrier fluid.

12. The method of claim 8, wherein the polycarbonate reactant contains two or more hydroxyl groups.

13. 10. The method of claim 8, further comprising preparing the polycarbonate reactant from a vegetable oil or mixture of vegetable oils containing two or more hydroxyl groups.

14. 10. The method of claim 8, further comprising preparing the polycarbonate reactant from a copolymer of dilinoleic acid or a mixture of copolymers of dilinoleic acid.

15. 1. A method for making a NIPU elastomer gel paste, comprising: i) shearing the NIPU elastomer of claim 8; ii) optionally adding an additional amount of a topically acceptable carrier fluid during shearing to form a gel paste composition; and iii) optionally adding a pharmaceutically active ingredient; A method comprising:

16. 16. A NIPU elastomer gel paste prepared by the method of claim 15.

17. 7. A topical formulation comprising the gel composition of claim 5 or claim 6, wherein the pharmaceutically active ingredient is a personal care active or a healthcare active.

18. 16. A topical formulation comprising the NIPU elastomer gel paste of claim 15, comprising a personal care active or a health care active.

19. A) polycarbonates or mixtures of polycarbonates containing two or more carbonate functional groups; B) a polyamine or mixture of polyamines containing two or more amine functional groups, wherein the amine functional groups are either primary or secondary; C) optionally a NIPU reaction catalyst; and D) a carrier fluid, wherein said carrier fluid is a reaction solvent or said carrier fluid is added after elastomer formation at a concentration of 50% (w / w) to 99.9% (w / w) of said gel composition.

20. 20. A foot-conforming shoe insole or sole comprising the non-isocyanate polyurethane (NIPU) elastomer of claim 1 or the gel composition of claim 19.

21. 20. A medically acceptable gel comprising the non-isocyanate polyurethane elastomer (NIPU) of claim 1 or the gel composition of claim 19.

22. 10. A topical formulation comprising the NIPU elastomer of claim 1.

23. 10. A gel composition comprising the non-isocyanate polyurethane (NIPU) elastomer of claim 1 and a topically acceptable carrier fluid at a concentration of 60% (w / w) to 99.9% (w / w) of the gel composition.

24. 1. A method for making a NIPU elastomer gel paste, comprising: i) shearing the gel paste of claim 23; ii) optionally adding an additional amount of a topically acceptable carrier fluid during shearing to form a gel paste composition; and iii) optionally adding a pharmaceutically active ingredient; A method comprising:

25. 25. A NIPU elastomer gel paste prepared by the method of claim 24.

26. 26. A topical formulation comprising the gel composition of claim 23 or the NIPU elastomer gel paste of claim 25.

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