ES2384101T3 - Polímeros termosensibles y geles termorreversibles obtenidos a partir de estos polímeros - Google Patents
Polímeros termosensibles y geles termorreversibles obtenidos a partir de estos polímeros Download PDFInfo
- Publication number
- ES2384101T3 ES2384101T3 ES03760030T ES03760030T ES2384101T3 ES 2384101 T3 ES2384101 T3 ES 2384101T3 ES 03760030 T ES03760030 T ES 03760030T ES 03760030 T ES03760030 T ES 03760030T ES 2384101 T3 ES2384101 T3 ES 2384101T3
- Authority
- ES
- Spain
- Prior art keywords
- polymer
- heat
- water
- thermosensitive
- polymers
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 229920000642 polymer Polymers 0.000 title claims abstract description 190
- 239000000499 gel Substances 0.000 title claims abstract description 81
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 44
- 239000004202 carbamide Substances 0.000 claims abstract description 36
- 125000000962 organic group Chemical group 0.000 claims abstract description 34
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims abstract description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 38
- 238000003786 synthesis reaction Methods 0.000 claims description 35
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 23
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 13
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 9
- 239000005977 Ethylene Substances 0.000 claims description 9
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 claims description 8
- 239000002537 cosmetic Substances 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- 229920001897 terpolymer Polymers 0.000 claims description 6
- 239000012429 reaction media Substances 0.000 claims description 5
- 238000011282 treatment Methods 0.000 claims description 5
- 230000002378 acidificating effect Effects 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- -1 polypropylene Polymers 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical group 0.000 claims description 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
- 238000001308 synthesis method Methods 0.000 claims description 2
- 239000004743 Polypropylene Substances 0.000 claims 2
- 229920001155 polypropylene Polymers 0.000 claims 2
- 125000001302 tertiary amino group Chemical group 0.000 claims 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 abstract description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 abstract description 3
- 239000000203 mixture Substances 0.000 description 26
- 239000000243 solution Substances 0.000 description 23
- 229920001983 poloxamer Polymers 0.000 description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 15
- 239000002253 acid Substances 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 229920001577 copolymer Polymers 0.000 description 11
- 238000001879 gelation Methods 0.000 description 11
- 239000012948 isocyanate Substances 0.000 description 11
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 10
- 239000007864 aqueous solution Substances 0.000 description 10
- 238000009472 formulation Methods 0.000 description 9
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 8
- RVGRUAULSDPKGF-UHFFFAOYSA-N Poloxamer Chemical compound C1CO1.CC1CO1 RVGRUAULSDPKGF-UHFFFAOYSA-N 0.000 description 8
- 230000008901 benefit Effects 0.000 description 8
- 239000002609 medium Substances 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 7
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- 229960000502 poloxamer Drugs 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 229920002125 Sokalan® Polymers 0.000 description 6
- 230000002209 hydrophobic effect Effects 0.000 description 6
- 230000003993 interaction Effects 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 5
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical group NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 5
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 5
- 238000004090 dissolution Methods 0.000 description 5
- 230000001965 increasing effect Effects 0.000 description 5
- 238000001556 precipitation Methods 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 230000002441 reversible effect Effects 0.000 description 5
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 229920001400 block copolymer Polymers 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000006482 condensation reaction Methods 0.000 description 4
- 239000000470 constituent Substances 0.000 description 4
- 239000011557 critical solution Substances 0.000 description 4
- 230000008034 disappearance Effects 0.000 description 4
- 150000002513 isocyanates Chemical group 0.000 description 4
- 238000006068 polycondensation reaction Methods 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 3
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 3
- 230000036760 body temperature Effects 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 238000005304 joining Methods 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 210000004400 mucous membrane Anatomy 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 150000003512 tertiary amines Chemical group 0.000 description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 125000005442 diisocyanate group Chemical group 0.000 description 2
- 239000006196 drop Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000693 micelle Substances 0.000 description 2
- QNILTEGFHQSKFF-UHFFFAOYSA-N n-propan-2-ylprop-2-enamide Chemical compound CC(C)NC(=O)C=C QNILTEGFHQSKFF-UHFFFAOYSA-N 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- 239000006069 physical mixture Substances 0.000 description 2
- 229920003172 poly (isopropyl acrylamide) Polymers 0.000 description 2
- 238000010526 radical polymerization reaction Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 229920005603 alternating copolymer Polymers 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000000227 bioadhesive Substances 0.000 description 1
- 210000000481 breast Anatomy 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000003636 chemical group Chemical group 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000000502 dialysis Methods 0.000 description 1
- 238000012377 drug delivery Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 210000003238 esophagus Anatomy 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000003889 eye drop Substances 0.000 description 1
- 229940012356 eye drops Drugs 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- 239000000017 hydrogel Substances 0.000 description 1
- 150000002433 hydrophilic molecules Chemical class 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 150000002829 nitrogen Chemical class 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 210000002307 prostate Anatomy 0.000 description 1
- 238000011403 purification operation Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 230000001131 transforming effect Effects 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 229920000428 triblock copolymer Polymers 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 230000037303 wrinkles Effects 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
- A61K9/0024—Solid, semi-solid or solidifying implants, which are implanted or injected in body tissue
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/34—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/0804—Manufacture of polymers containing ionic or ionogenic groups
- C08G18/0819—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups
- C08G18/0823—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups containing carboxylate salt groups or groups forming them
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3271—Hydroxyamines
- C08G18/3275—Hydroxyamines containing two hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/34—Carboxylic acids; Esters thereof with monohydroxyl compounds
- C08G18/348—Hydroxycarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4833—Polyethers containing oxyethylene units
- C08G18/4837—Polyethers containing oxyethylene units and other oxyalkylene units
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4833—Polyethers containing oxyethylene units
- C08G18/4837—Polyethers containing oxyethylene units and other oxyalkylene units
- C08G18/4841—Polyethers containing oxyethylene units and other oxyalkylene units containing oxyethylene end groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6666—Compounds of group C08G18/48 or C08G18/52
- C08G18/667—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38
- C08G18/6681—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/32 or C08G18/3271 and/or polyamines of C08G18/38
- C08G18/6688—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/32 or C08G18/3271 and/or polyamines of C08G18/38 with compounds of group C08G18/3271
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
- C08G18/758—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing two or more cycloaliphatic rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/333—Polymers modified by chemical after-treatment with organic compounds containing nitrogen
- C08G65/33344—Polymers modified by chemical after-treatment with organic compounds containing nitrogen containing carbamate group
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/333—Polymers modified by chemical after-treatment with organic compounds containing nitrogen
- C08G65/33348—Polymers modified by chemical after-treatment with organic compounds containing nitrogen containing isocyanate group
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2210/00—Compositions for preparing hydrogels
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2650/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G2650/28—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type
- C08G2650/58—Ethylene oxide or propylene oxide copolymers, e.g. pluronics
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Inorganic Chemistry (AREA)
- Manufacturing & Machinery (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Dermatology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Ophthalmology & Optometry (AREA)
- Polyurethanes Or Polyureas (AREA)
- Polyethers (AREA)
- Cosmetics (AREA)
- Medicinal Preparation (AREA)
- Paints Or Removers (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
- Polyesters Or Polycarbonates (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Materials For Medical Uses (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0207463A FR2840907B1 (fr) | 2002-06-14 | 2002-06-14 | Polymere thermo-sensible ameliore susceptible de former des gels thermoreversibles a haut indice de viscosification |
| FR0207463 | 2002-06-14 | ||
| PCT/FR2003/001786 WO2003106536A2 (fr) | 2002-06-14 | 2003-06-13 | Polymeres thermosensibles et gels thermoreversibles obtenus a partir de ces polymeres |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2384101T3 true ES2384101T3 (es) | 2012-06-29 |
Family
ID=29595325
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES03760030T Expired - Lifetime ES2384101T3 (es) | 2002-06-14 | 2003-06-13 | Polímeros termosensibles y geles termorreversibles obtenidos a partir de estos polímeros |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US7339013B2 (https=) |
| EP (1) | EP1521795B1 (https=) |
| JP (1) | JP5237523B2 (https=) |
| AT (1) | ATE549366T1 (https=) |
| AU (1) | AU2003258799A1 (https=) |
| CA (1) | CA2489828C (https=) |
| ES (1) | ES2384101T3 (https=) |
| FR (1) | FR2840907B1 (https=) |
| WO (1) | WO2003106536A2 (https=) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1709126B1 (en) * | 2004-01-08 | 2008-03-12 | Hercules Incorporated | Colorant compatible synthetic thickener for paint |
| GB0613638D0 (en) * | 2006-07-08 | 2006-08-16 | Controlled Therapeutics Sct | Polyurethane elastomers |
| FR2903599B1 (fr) * | 2006-07-13 | 2012-08-31 | Oreal | Composition cosmetique a phase continue aqueuse comprenant au moins un polymere thermogelifiant, au moins un solvant organique volatil miscible dans l'eau et au moins un agent absorbant les radiations uv. |
| KR100924430B1 (ko) | 2007-11-13 | 2009-10-29 | 이화여자대학교 산학협력단 | 온도 민감성 졸-젤 전이 ｐｐ－ｐｌｘ－ｐｐ 블록 공중합체및 이의 제조 방법 |
| FR2932070B1 (fr) | 2008-06-10 | 2012-08-17 | Oreal | Ensemble de maquillage et/ou de soin des cils |
| FR2940761B1 (fr) | 2009-01-07 | 2012-12-28 | Polymerexpert Sa | Composition anti-ronflement contenant un polymere thermogelifiant |
| WO2013131575A1 (en) * | 2012-03-09 | 2013-09-12 | Alfaparf Group S.P.A. | Foamable coloring compositions comprising a thermo-sensitive polymer |
| WO2013131576A1 (en) * | 2012-03-09 | 2013-09-12 | Alfaparf Group S.P.A. | Foamable bleaching compositions comprising a thermo-sensitive polymer |
| US9408785B2 (en) | 2012-10-15 | 2016-08-09 | L'oreal | Hair styling compositions containing aqueous wax dispersions |
| US10626294B2 (en) | 2012-10-15 | 2020-04-21 | L'oreal | Aqueous wax dispersions containing volatile solvents |
| US10413496B2 (en) | 2012-10-15 | 2019-09-17 | L'oreal | Aqueous wax dispersions |
| DE102012223416A1 (de) * | 2012-12-17 | 2014-07-03 | Polymaterials Ag | Kettenverlängerte Poloxamere, daraus gebildete thermoreversible Hydrogele mit biologischen Materialien, und medizinische Anwendungen derselben |
| US8992895B2 (en) | 2012-12-19 | 2015-03-31 | L'oreal | Sunscreen compositions |
| US20180214363A9 (en) * | 2013-03-11 | 2018-08-02 | Noxell Corporation | Method for Colouring Hair |
| EP2777688A1 (en) * | 2013-03-11 | 2014-09-17 | The Procter and Gamble Company | Method for colouring hair |
| US10561596B2 (en) | 2014-04-11 | 2020-02-18 | L'oreal | Compositions and dispersions containing particles comprising a polymer |
| FR3021213B1 (fr) | 2014-05-20 | 2017-09-01 | Bcm Cosmetique | Composition cosmetique de revetement des fibres keratiniques, en particulier des cils |
| EP3261607B1 (en) | 2015-02-26 | 2020-11-04 | Edgewell Personal Care Brands, LLC | Sunscreen compositions with improved water resistance |
| CN107708429A (zh) | 2015-04-24 | 2018-02-16 | 国际香料和香精公司 | 递送体系及其制备方法 |
| FR3091996B1 (fr) | 2019-01-24 | 2021-01-29 | Les Laboratoires Brothier | Composition cicatrisante |
| CN116437897A (zh) | 2020-11-03 | 2023-07-14 | 高露洁-棕榄公司 | 口腔水凝胶组合物和用途 |
| FR3119776B1 (fr) | 2021-02-12 | 2023-04-28 | Braun Medical | Kit de sonde urinaire |
| IT202100024155A1 (it) | 2021-09-21 | 2023-03-21 | Chromavis Spa | Articolo cosmetico in stick e un metodo per realizzarlo |
| WO2023055916A1 (en) | 2021-09-30 | 2023-04-06 | Coty Inc. | Fragrance compositions based on polyurethane |
| CN120897765A (zh) * | 2023-03-29 | 2025-11-04 | 康沃特克有限公司 | 导管 |
| FR3148372A1 (fr) | 2023-05-05 | 2024-11-08 | Polymerexpert Sa | Polymères thermogélifiants aptes à former un revêtement glissant pour injecteur ophtalmique |
| FR3154337B1 (fr) | 2023-10-24 | 2025-10-03 | Alphanov | Procédé et dispositif de manipulation microfluidique à base de liquide thermo-visqueux |
| WO2026080344A1 (en) | 2024-10-07 | 2026-04-16 | Colgate-Palmolive Company | Oral care gels with fluoride source and polymer blend |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1127082B (de) * | 1959-02-26 | 1962-04-05 | Hoechst Ag | Verfahren zur Herstellung von hochmolekularen wasserloeslichen oder wasserquellbaren Polyaetherurethanen |
| DE3342864A1 (de) * | 1983-11-26 | 1985-06-05 | Basf Ag, 6700 Ludwigshafen | Fluessige, harnstoffgruppen enthaltende polyisocyanatmischungen, verfahren zu deren herstellung und deren verwendung zur herstellung von kompakten oder zelligen polyurethan- und/oder polyisocyanurat-kunststoffen, insbesondere polyurethan-weichschaumstoffen |
| US5175229A (en) * | 1986-11-18 | 1992-12-29 | W. R. Grace & Co.-Conn. | Biocompatible polyurea-urethane hydrated polymers |
| JPS63256651A (ja) * | 1987-04-14 | 1988-10-24 | Dainippon Ink & Chem Inc | 安定性、耐久性に優れる変性ポリウレタン水分散液 |
| EP0400015A4 (en) * | 1987-12-02 | 1991-01-16 | Tyndale Plains-Hunter, Ltd. | Hydrophilic polyurethanes of improved strength |
| EP0401210A4 (en) * | 1988-02-01 | 1990-12-27 | Tyndale Plains-Hunter, Ltd. | Thermally reversible polyurethane hydrogels and cosmetic, biological and medical uses |
| US5000955A (en) * | 1988-07-29 | 1991-03-19 | Tyndale Plains-Hunter Ltd. | Thermally reversible polyurethane hydrogels and cosmetic, biological and medical uses |
| US5183876A (en) * | 1988-08-04 | 1993-02-02 | Bayer Aktiengesellschaft | Urea group-containing polyisocyanates modified with long chain compounds and a process for their preparation |
| EP0551626A1 (en) * | 1991-12-19 | 1993-07-21 | LEK, tovarna farmacevtskih in kemicnih izdelkov, d.d. | Thermoreversible gel as a liquid pharmaceutical carrier for a galenic formulation |
| JP3121660B2 (ja) * | 1992-01-31 | 2001-01-09 | 有限会社荻田バイオマテリアル研究所 | 熱可逆性ハイドロゲル材料 |
| US5589563A (en) * | 1992-04-24 | 1996-12-31 | The Polymer Technology Group | Surface-modifying endgroups for biomedical polymers |
| JP3491917B2 (ja) * | 1993-02-05 | 2004-02-03 | メビオール株式会社 | 熱可逆性ハイドロゲル材料 |
| GB9306887D0 (en) * | 1993-04-01 | 1993-05-26 | Graham Neil B | Random block copolymers |
| GB9313017D0 (en) * | 1993-06-24 | 1993-08-11 | Univ Strathclyde | Measurement of water content |
| EP0963796B1 (en) * | 1995-02-01 | 2009-06-17 | Boston Scientific Scimed, Inc. | Medical device comprising a chemically treated metallic substrate |
| JPH11510837A (ja) * | 1995-07-28 | 1999-09-21 | フォーカル，インコーポレイテッド | 薬物送達のための制御された放出薬剤および組織処置薬剤としての使用のためのマルチブロック生分解性ヒドロゲル |
| US6130309A (en) * | 1996-09-20 | 2000-10-10 | Tyndale Plains-Hunter, Ltd. | Hydrophilic polyether polyurethanes containing carboxylic acid |
| AU2905699A (en) * | 1998-03-18 | 1999-10-11 | Tyndale Plains-Hunter Ltd. | Hydrophilic polyether polyurethanes containing carboxylic acid |
-
2002
- 2002-06-14 FR FR0207463A patent/FR2840907B1/fr not_active Expired - Fee Related
-
2003
- 2003-06-13 AU AU2003258799A patent/AU2003258799A1/en not_active Abandoned
- 2003-06-13 JP JP2004513361A patent/JP5237523B2/ja not_active Expired - Lifetime
- 2003-06-13 EP EP03760030A patent/EP1521795B1/fr not_active Expired - Lifetime
- 2003-06-13 CA CA2489828A patent/CA2489828C/en not_active Expired - Fee Related
- 2003-06-13 ES ES03760030T patent/ES2384101T3/es not_active Expired - Lifetime
- 2003-06-13 AT AT03760030T patent/ATE549366T1/de active
- 2003-06-13 WO PCT/FR2003/001786 patent/WO2003106536A2/fr not_active Ceased
-
2004
- 2004-12-13 US US11/010,929 patent/US7339013B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JP5237523B2 (ja) | 2013-07-17 |
| JP2005534732A (ja) | 2005-11-17 |
| CA2489828C (en) | 2012-04-10 |
| WO2003106536A3 (fr) | 2004-04-01 |
| EP1521795A2 (fr) | 2005-04-13 |
| FR2840907B1 (fr) | 2005-11-25 |
| AU2003258799A1 (en) | 2003-12-31 |
| US20050175573A1 (en) | 2005-08-11 |
| WO2003106536A2 (fr) | 2003-12-24 |
| FR2840907A1 (fr) | 2003-12-19 |
| ATE549366T1 (de) | 2012-03-15 |
| CA2489828A1 (en) | 2003-12-24 |
| US7339013B2 (en) | 2008-03-04 |
| EP1521795B1 (fr) | 2012-03-14 |
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