CA2489828C - Thermosensitive polymers and thermoreversible gels obtained from these polymers - Google Patents
Thermosensitive polymers and thermoreversible gels obtained from these polymers Download PDFInfo
- Publication number
- CA2489828C CA2489828C CA2489828A CA2489828A CA2489828C CA 2489828 C CA2489828 C CA 2489828C CA 2489828 A CA2489828 A CA 2489828A CA 2489828 A CA2489828 A CA 2489828A CA 2489828 C CA2489828 C CA 2489828C
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- Prior art keywords
- thermosensitive
- polymer
- peo
- polymers
- ppo
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- 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.)
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- 229920000642 polymer Polymers 0.000 title claims abstract description 191
- 239000000499 gel Substances 0.000 title claims abstract description 76
- 239000004202 carbamide Substances 0.000 claims abstract description 35
- 125000000962 organic group Chemical group 0.000 claims abstract description 34
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims abstract description 20
- 229920001451 polypropylene glycol Polymers 0.000 claims abstract description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 43
- -1 poly(ethylene oxide) Polymers 0.000 claims description 28
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical group NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 25
- 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 22
- 239000000243 solution Substances 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 21
- 239000002253 acid Chemical group 0.000 claims description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
- 229920000463 Poly(ethylene glycol)-block-poly(propylene glycol)-block-poly(ethylene glycol) Polymers 0.000 claims description 14
- 239000007864 aqueous solution Substances 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 10
- 229920001897 terpolymer Polymers 0.000 claims description 9
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
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- 239000011557 critical solution Substances 0.000 description 8
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 3
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- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
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- 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
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
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- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 1
- 238000007040 multi-step synthesis reaction Methods 0.000 description 1
- QNILTEGFHQSKFF-UHFFFAOYSA-N n-propan-2-ylprop-2-enamide Chemical compound CC(C)NC(=O)C=C QNILTEGFHQSKFF-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
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- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 229920000428 triblock copolymer Polymers 0.000 description 1
- 230000037303 wrinkles Effects 0.000 description 1
Classifications
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- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
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- C08G18/3275—Hydroxyamines containing two hydroxy groups
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- 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
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/4841—Polyethers containing oxyethylene units and other oxyalkylene units containing oxyethylene end groups
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- 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
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- C08G18/667—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08G2210/00—Compositions for preparing hydrogels
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- 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
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- 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 |
|---|---|---|---|
| FR02/07463 | 2002-06-14 | ||
| FR0207463A FR2840907B1 (fr) | 2002-06-14 | 2002-06-14 | Polymere thermo-sensible ameliore susceptible de former des gels thermoreversibles a haut indice de viscosification |
| PCT/FR2003/001786 WO2003106536A2 (fr) | 2002-06-14 | 2003-06-13 | Polymeres thermosensibles et gels thermoreversibles obtenus a partir de ces polymeres |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2489828A1 CA2489828A1 (en) | 2003-12-24 |
| CA2489828C true CA2489828C (en) | 2012-04-10 |
Family
ID=29595325
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2489828A Expired - Fee Related CA2489828C (en) | 2002-06-14 | 2003-06-13 | Thermosensitive polymers and thermoreversible gels obtained from these polymers |
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 |
| ES2384101T3 (es) | 2012-06-29 |
| 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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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20210614 |