CN108467464A - 含壬二酸可见光固化水凝胶及其制备方法 - Google Patents
含壬二酸可见光固化水凝胶及其制备方法 Download PDFInfo
- Publication number
- CN108467464A CN108467464A CN201810283134.7A CN201810283134A CN108467464A CN 108467464 A CN108467464 A CN 108467464A CN 201810283134 A CN201810283134 A CN 201810283134A CN 108467464 A CN108467464 A CN 108467464A
- Authority
- CN
- China
- Prior art keywords
- azelaic acid
- hydrogel
- visible
- parts
- weight
- 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.)
- Pending
Links
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 title claims abstract description 92
- 239000000017 hydrogel Substances 0.000 title claims abstract description 28
- 238000002360 preparation method Methods 0.000 title claims abstract description 14
- 239000000178 monomer Substances 0.000 claims abstract description 20
- 238000004132 cross linking Methods 0.000 claims abstract description 10
- 239000003999 initiator Substances 0.000 claims abstract description 10
- 238000000034 method Methods 0.000 claims abstract description 9
- 230000005855 radiation Effects 0.000 claims abstract description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 10
- -1 N- ethenyl pyrrolidones Ketone Chemical class 0.000 claims description 10
- 229920001223 polyethylene glycol Polymers 0.000 claims description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 7
- 239000002202 Polyethylene glycol Substances 0.000 claims description 7
- 125000004386 diacrylate group Chemical group 0.000 claims description 6
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 claims description 5
- VNQXSTWCDUXYEZ-UHFFFAOYSA-N 1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-dione Chemical compound C1CC2(C)C(=O)C(=O)C1C2(C)C VNQXSTWCDUXYEZ-UHFFFAOYSA-N 0.000 claims description 5
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 5
- 229930006711 bornane-2,3-dione Natural products 0.000 claims description 5
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 5
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 claims description 4
- 150000001336 alkenes Chemical class 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 239000012752 auxiliary agent Substances 0.000 claims description 3
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 3
- WERYXYBDKMZEQL-UHFFFAOYSA-N 1,4-butanediol Substances OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 2
- CCJAYIGMMRQRAO-UHFFFAOYSA-N 2-[4-[(2-hydroxyphenyl)methylideneamino]butyliminomethyl]phenol Chemical compound OC1=CC=CC=C1C=NCCCCN=CC1=CC=CC=C1O CCJAYIGMMRQRAO-UHFFFAOYSA-N 0.000 claims description 2
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 2
- NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 claims description 2
- OKKRPWIIYQTPQF-UHFFFAOYSA-N Trimethylolpropane trimethacrylate Chemical compound CC(=C)C(=O)OCC(CC)(COC(=O)C(C)=C)COC(=O)C(C)=C OKKRPWIIYQTPQF-UHFFFAOYSA-N 0.000 claims description 2
- 229930014669 anthocyanidin Natural products 0.000 claims description 2
- 150000001452 anthocyanidin derivatives Chemical class 0.000 claims description 2
- 235000008758 anthocyanidins Nutrition 0.000 claims description 2
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N benzo-alpha-pyrone Natural products C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 claims description 2
- 229960000956 coumarin Drugs 0.000 claims description 2
- 235000001671 coumarin Nutrition 0.000 claims description 2
- YQGOJNYOYNNSMM-UHFFFAOYSA-N eosin Chemical compound [Na+].OC(=O)C1=CC=CC=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C(O)=C(Br)C=C21 YQGOJNYOYNNSMM-UHFFFAOYSA-N 0.000 claims description 2
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical class [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 claims description 2
- 229960004194 lidocaine Drugs 0.000 claims description 2
- CXKWCBBOMKCUKX-UHFFFAOYSA-M methylene blue Chemical compound [Cl-].C1=CC(N(C)C)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 CXKWCBBOMKCUKX-UHFFFAOYSA-M 0.000 claims description 2
- 229960000907 methylthioninium chloride Drugs 0.000 claims description 2
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 claims description 2
- 229940043267 rhodamine b Drugs 0.000 claims description 2
- MNCGMVDMOKPCSQ-UHFFFAOYSA-M sodium;2-phenylethenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C=CC1=CC=CC=C1 MNCGMVDMOKPCSQ-UHFFFAOYSA-M 0.000 claims description 2
- MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 claims 1
- BMYFPLOKANOKIT-UHFFFAOYSA-N 2-(2-methylprop-2-enoyloxy)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOC(=O)C(C)=C.CC(=C)C(=O)OCCOC(=O)C(C)=C BMYFPLOKANOKIT-UHFFFAOYSA-N 0.000 claims 1
- PQJUJGAVDBINPI-UHFFFAOYSA-N 9H-thioxanthene Chemical compound C1=CC=C2CC3=CC=CC=C3SC2=C1 PQJUJGAVDBINPI-UHFFFAOYSA-N 0.000 claims 1
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 claims 1
- ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 claims 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims 1
- 238000003756 stirring Methods 0.000 claims 1
- 238000001723 curing Methods 0.000 abstract description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 6
- 230000000694 effects Effects 0.000 abstract description 4
- 230000000638 stimulation Effects 0.000 abstract description 4
- 235000019441 ethanol Nutrition 0.000 abstract description 3
- 239000003960 organic solvent Substances 0.000 abstract description 3
- 238000003848 UV Light-Curing Methods 0.000 abstract description 2
- 208000027418 Wounds and injury Diseases 0.000 abstract description 2
- 230000006378 damage Effects 0.000 abstract description 2
- 230000007613 environmental effect Effects 0.000 abstract description 2
- 208000014674 injury Diseases 0.000 abstract description 2
- 230000003020 moisturizing effect Effects 0.000 abstract description 2
- 230000008901 benefit Effects 0.000 description 3
- 206010067484 Adverse reaction Diseases 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- SHGAZHPCJJPHSC-UHFFFAOYSA-N Panrexin Chemical compound OC(=O)C=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-UHFFFAOYSA-N 0.000 description 2
- 206010040880 Skin irritation Diseases 0.000 description 2
- 230000006838 adverse reaction Effects 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- AESPYQQDASDLHC-UHFFFAOYSA-N 2h-benzo[g]thiochromene Chemical compound C1=CC=C2C=C(C=CCS3)C3=CC2=C1 AESPYQQDASDLHC-UHFFFAOYSA-N 0.000 description 1
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 description 1
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- CSTYVZIYKPZTEE-UHFFFAOYSA-N C=1C=CC=CC=1[Ti]C1=CC=CC=C1 Chemical class C=1C=CC=CC=1[Ti]C1=CC=CC=C1 CSTYVZIYKPZTEE-UHFFFAOYSA-N 0.000 description 1
- 206010059866 Drug resistance Diseases 0.000 description 1
- XEUCQOBUZPQUMQ-UHFFFAOYSA-N Glycolone Chemical compound COC1=C(CC=C(C)C)C(=O)NC2=C1C=CC=C2OC XEUCQOBUZPQUMQ-UHFFFAOYSA-N 0.000 description 1
- UWIULCYKVGIOPW-UHFFFAOYSA-N Glycolone Natural products CCOC1=C(CC=CC)C(=O)N(C)c2c(O)cccc12 UWIULCYKVGIOPW-UHFFFAOYSA-N 0.000 description 1
- SHGAZHPCJJPHSC-NUEINMDLSA-N Isotretinoin Chemical compound OC(=O)C=C(C)/C=C/C=C(C)C=CC1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-NUEINMDLSA-N 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical group C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- 208000003251 Pruritus Diseases 0.000 description 1
- 241000882890 Renova Species 0.000 description 1
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229960005280 isotretinoin Drugs 0.000 description 1
- 230000001937 non-anti-biotic effect Effects 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 229940059527 renova Drugs 0.000 description 1
- 229940002683 retin-a Drugs 0.000 description 1
- 230000036556 skin irritation Effects 0.000 description 1
- 231100000475 skin irritation Toxicity 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/06—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polyethers, polyoxymethylenes or polyacetals
- C08F283/065—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polyethers, polyoxymethylenes or polyacetals on to unsaturated polyethers, polyoxymethylenes or polyacetals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/20—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids
-
- 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
- A61K47/32—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers, poly(meth)acrylates, or polyvinyl pyrrolidone
-
- 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
- A61K9/0014—Skin, i.e. galenical aspects of topical compositions
-
- 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
- A61K9/06—Ointments; Bases therefor; Other semi-solid forms, e.g. creams, sticks, gels
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/10—Anti-acne agents
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/20—Esters of polyhydric alcohols or phenols, e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(meth)acrylate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F299/00—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers
- C08F299/02—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates
- C08F299/026—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates from the reaction products of polyepoxides and unsaturated monocarboxylic acids, their anhydrides, halogenides or esters with low molecular weight
Abstract
本发明要求保护一种含壬二酸可见光固化水凝胶,其通过如下方法制备得到:含壬二酸可见光固化水凝胶的制备方法,包括如下步骤:取水溶性单体40‑80重量份、多官能团交联单体1‑20重量份、可见光引发剂体系0.1‑5重量份、壬二酸1‑20重量份,将各组分搅拌均匀后,在一定温度下,经过可见光照射反应一段时间,得到含壬二酸可见光固化水凝胶。本发明含壬二酸水凝胶避免使用乙醇有机溶剂;本发明含壬二酸水凝胶与人体皮肤亲和性好,具有保湿滋润作用,同时壬二酸因包覆在水凝胶中,起到缓释效果,可以缓解壬二酸产品使用初期对皮肤的刺激作用;本发明采用可见光固化技术制备水凝胶,避免紫外光固化体系对环境和人体的伤害作用,属于绿色环保技术。
Description
技术领域
本发明涉及化工技术领域,具体涉及一种含壬二酸可见光固化水凝胶及其制备方法。
背景技术
壬二酸(Azelaic acid,AZA)是一种局部应用的非抗生素类治疗痤疮药物,具有长期用药后细菌不易产生耐药性、使用安全等优点。目前已用于临床的壬二酸外用制剂主要为乳膏剂,如台湾思丽安乳膏,Aziderm乳膏等,但存在一些不良反应,如局部灼痛、瘙痒、红斑等。引起这些不良反应的主要原因在于壬二酸的溶解性差,从而需要使用过量的壬二酸才能发挥治疗作用,而壬二酸的浓度越高,越容易对皮肤产生刺激。因此,采用水凝胶手段以增加壬二酸的溶解度,并起到缓释作用,从而提高其利用度、减小其对皮肤的刺激,具有重要意义。
发明内容
本发明旨在解决现有的壬二酸药物刺激皮肤的缺陷,提供一种含壬二酸可见光固化水凝胶。
本发明的目的是通过如下技术方案实现的:含壬二酸可见光固化水凝胶的制备方法,其包括如下步骤:
取水溶性单体40-80重量份、多官能团交联单体1-20重量份、可见光引发剂体系0.1-5重量份、壬二酸1-20重量份,将各组分搅拌均匀后,在一定温度下,经过可见光照射反应一段时间,得到含壬二酸可见光固化水凝胶。
本发明优选的技术方案中,取水溶性单体70-80重量份、多官能团交联单体1-10重量份、可见光引发剂体系1-5重量份、壬二酸10-20重量份,将各组分搅拌均匀后,在一定温度下,经过可见光照射反应一段时间,得到含壬二酸可见光固化水凝胶。
本发明优选的技术方案中,所述水溶性单体选自N-乙烯基吡咯烷酮、丙烯酰胺、N-羟甲基丙烯酰胺、丙烯酸、丙烯酸羟乙酯、丙烯酸羟丙酯、丙烯酸二甲氨基乙脂、聚乙二醇丙烯酸酯、聚乙二醇甲醚丙烯酸酯、甲基丙烯酸、甲基丙烯酸羟乙酯、甲基丙烯酸羟丙酯、甲基丙烯酸二甲氨基乙脂、甲基丙烯酸二乙氨基乙脂、聚(乙二醇)甲基丙烯酸酯、聚乙二醇甲醚甲基丙烯酸酯、苯乙烯磺酸钠中的一种或几种组合。
本发明优选的技术方案中,所述多官能团交联单体选自N,N-亚甲基双丙烯酰胺、二丙烯酸-1,4-丁二醇酯、二甲基丙烯酸乙二醇酯、聚乙二醇二丙烯酸酯、聚乙二醇二甲基丙烯酸酯、三羟甲基丙烷三丙烯酸酯,丙氧化甘油三丙烯酸酯,季戊四醇三丙烯酸酯,季戊四醇四丙烯酸酯等中的一种或几种组合。
本发明优选的技术方案中,所述可见光引发剂体系选自樟脑醌,香豆素酮,硫杂蒽,二茂铁盐类,氟化二苯基钛茂和双(五氟苯基)钛茂等钛烯类,以及花青素、罗丹明B、孟加拉玫瑰红、曙红、亚甲基蓝、吖啶等染料类中的一种或几种组合。
本发明优选的技术方案中,所述反应温度范围为0-100℃,优选为20-65℃。
本发明优选的技术方案中,在上述的反应体系中加入药学上可使用的助剂,所述助剂选自甘油,维生素。
本发明优选的技术方案中,反应时间为1-60分钟,优选为10-30分钟。
本发明的第二方面提供上述方法制备得到的含壬二酸可见光固化水凝胶。
本发明的优点包括:
(1)由于壬二酸在冷水中溶解度低,为了让壬二酸充分溶解和分散均匀,避免在低温环境或者冷藏过程中析出,通常需要使用乙醇等有机溶剂,本发明含壬二酸水凝胶可以避免使用乙醇这些有机溶剂;
(2)壬二酸乳膏产品,因壬二酸浓度一般为10%-20%,直接与皮肤接触,使用初期容易引起皮肤刺痛和红肿,本发明含壬二酸水凝胶与人体皮肤亲和性好,具有保湿滋润作用,同时壬二酸因包覆在水凝胶中,起到缓释效果,可以缓解壬二酸产品使用初期对皮肤的刺激作用;
(3)本发明采用可见光固化技术制备水凝胶,避免紫外光固化体系对环境和人体的伤害作用,属于绿色环保技术。
附图说明
图1是本发明的含壬二酸可见光固化水凝胶制备方法的一实施例工艺流程图。
具体实施方式
为进一步理解本发明,下面结合具体实施例对本发明优选方案进行描述,但是应当理解,这些描述只是为进一步说明本发明的特征和优点,而不是对本发明权利要求的限制。
以下结合具体实施例对上述方案做进一步说明。应理解,这些实施例是用于说明本发明而不限于限制本发明的范围。实施例中采用的实施条件可以根据具体厂家的条件做进一步调整,未注明的实施条件通常为常规实验中的条件。
实施例1:甲基丙烯酸羟乙酯为水溶性主单体重量份80份,聚乙二醇二甲基丙烯酸酯为交联单体重量份3份,樟脑醌为可见光引发剂重量份2份,壬二酸为药物添加剂15份,混合均匀后,室温下经可见光辐照30分钟,形成含壬二酸水凝胶。
实施例2:甲基丙烯酸羟乙酯为水溶性主单体重量份80份,N,N-亚甲基双丙烯酰胺为交联单体重量份5份,樟脑醌为可见光引发剂重量份5份,壬二酸为药物添加剂10份,混合均匀后,60℃经可见光辐照10分钟,形成含壬二酸水凝胶。
实施例3:聚乙二醇甲醚丙烯酸酯为主单体重量份份73份,聚乙二醇二丙烯酸酯为交联单体5份,樟脑醌为可见光引发剂2份,壬二酸重量份20份为药物添加剂,混合均匀后,室温下经可见光辐照20分钟,形成含壬二酸水凝胶。
实施例4:聚乙二醇甲醚丙烯酸酯为主单体重量份份75份,聚乙二醇二丙烯酸酯为交联单体3份,氟化二苯基钛茂(Irgacure 784)为可见光引发剂2份,壬二酸重量份20份为药物添加剂,混合均匀后,室温下经可见光辐照60分钟,形成含壬二酸水凝胶。
本发明的技术内容及技术特征已揭示如上,然而熟悉本领域的技术人员仍可能基于本发明的教示及揭示而作种种不背离本发明精神的替换及修饰,因此,本发明保护范围应不限于实施例所揭示的内容,而应包括各种不背离本发明的替换及修饰,并为本专利申请权利要求所涵盖。
Claims (8)
1.含壬二酸可见光固化水凝胶的制备方法,其特征在于,包括如下步骤:
取水溶性单体40-80重量份、多官能团交联单体1-20重量份、可见光引发剂体系0.1-5重量份、壬二酸1-20重量份,将各组分搅拌均匀后,在一定温度下,经过可见光照射反应一段时间,得到含壬二酸可见光固化水凝胶。
2.根据权利要求1所述的制备方法,其特征在于,所述水溶性单体选自N-乙烯基吡咯烷酮、丙烯酰胺、N-羟甲基丙烯酰胺、丙烯酸、丙烯酸羟乙酯、丙烯酸羟丙酯、丙烯酸二甲氨基乙脂、聚乙二醇丙烯酸酯、聚乙二醇甲醚丙烯酸酯、甲基丙烯酸、甲基丙烯酸羟乙酯、甲基丙烯酸羟丙酯、甲基丙烯酸二甲氨基乙脂、甲基丙烯酸二乙氨基乙脂、聚(乙二醇)甲基丙烯酸酯、聚乙二醇甲醚甲基丙烯酸酯、苯乙烯磺酸钠中的一种或几种组合。
3.根据权利要求1所述的制备方法,其特征在于,所述多官能团交联单体选自N,N-亚甲基双丙烯酰胺、二丙烯酸-1,4-丁二醇酯、二甲基丙烯酸乙二醇酯、聚乙二醇二丙烯酸酯、聚乙二醇二甲基丙烯酸酯、三羟甲基丙烷三丙烯酸酯,丙氧化甘油三丙烯酸酯,季戊四醇三丙烯酸酯,季戊四醇四丙烯酸酯中的一种或几种组合。
4.根据权利要求1所述的制备方法,其特征在于,所述可见光引发剂体系选自樟脑醌,香豆素酮,硫杂蒽,二茂铁盐类,氟化二苯基钛茂和双(五氟苯基)钛茂,花青素、罗丹明B、孟加拉玫瑰红、曙红、亚甲基蓝、吖啶中的一种或几种组合。
5.根据权利要求1所述的制备方法,其特征在于,所述反应温度范围为0-100℃。
6.根据权利要求1所述的制备方法,其特征在于,在上述的反应体系中加入药学上可使用的助剂。
7.根据权利要求1所述的制备方法,其特征在于,反应时间为1-60分钟。
8.一种如权利要求1-7任一项方法制备得到的含壬二酸可见光固化水凝胶。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201810283134.7A CN108467464A (zh) | 2018-04-02 | 2018-04-02 | 含壬二酸可见光固化水凝胶及其制备方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201810283134.7A CN108467464A (zh) | 2018-04-02 | 2018-04-02 | 含壬二酸可见光固化水凝胶及其制备方法 |
Publications (1)
Publication Number | Publication Date |
---|---|
CN108467464A true CN108467464A (zh) | 2018-08-31 |
Family
ID=63262415
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201810283134.7A Pending CN108467464A (zh) | 2018-04-02 | 2018-04-02 | 含壬二酸可见光固化水凝胶及其制备方法 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN108467464A (zh) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN112480308A (zh) * | 2020-11-25 | 2021-03-12 | 复旦大学 | 一种智能水凝胶及其制备方法 |
CN112538173A (zh) * | 2019-09-23 | 2021-03-23 | 天津大学 | 甲基丙烯酸羟乙酯基本体聚合水凝胶及其制备方法 |
CN113521382A (zh) * | 2021-07-26 | 2021-10-22 | 台山市弘毅医疗用品有限公司 | 一种生物医用抗菌复合水凝胶的制备方法 |
Citations (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4628078A (en) * | 1984-06-12 | 1986-12-09 | Allied Colloids Ltd. | Acrylamide-dialkylaminoacrylate-dialkylaminomethacrylate cationic polyelectrolytes and their production |
US4963348A (en) * | 1987-12-11 | 1990-10-16 | The Procter & Gamble Company | Styling agents and compositions containing the same |
CN1072843A (zh) * | 1991-10-16 | 1993-06-09 | 理查森-维克斯有限公司 | 凝胶型化妆品组合物 |
CN1091317A (zh) * | 1992-07-28 | 1994-08-31 | 普罗格特-甘布尔公司 | 改进药品的局部输入 |
CN1382165A (zh) * | 1999-10-25 | 2002-11-27 | 庄臣及庄臣视力保护公司 | 制备光学品质聚合物的方法 |
CN1730515A (zh) * | 2005-08-26 | 2006-02-08 | 徐州恩华药业集团有限责任公司 | 一种制备水凝胶的方法 |
CN101186706A (zh) * | 2007-11-15 | 2008-05-28 | 天津大学 | 一种peg系凝胶纳米颗粒的制备方法 |
CN101302264A (zh) * | 2007-05-11 | 2008-11-12 | 北京化工大学 | 一种含不饱和双键的聚合物乳液及其制备方法 |
CN101466358A (zh) * | 2006-06-15 | 2009-06-24 | 帝斯曼知识产权资产管理有限公司 | 在敏感药物化合物的存在下通过辐射制备聚合基质的方法 |
CN101511339A (zh) * | 2005-08-04 | 2009-08-19 | 因滕迪斯有限公司 | 无水多相凝胶体系 |
CN101885906A (zh) * | 2010-07-17 | 2010-11-17 | 厦门大学 | 一种可降解生物水凝胶及其制备方法 |
CN102250263A (zh) * | 2011-05-05 | 2011-11-23 | 北京化工大学 | 一种利用紫外光聚合在低温下制备高分子结晶的方法 |
CN102639097A (zh) * | 2011-03-21 | 2012-08-15 | 博任达生化科技(上海)有限公司 | 逆向温敏可逆水凝胶组合物 |
WO2016028237A1 (en) * | 2014-08-22 | 2016-02-25 | Koç Üniversitesi | A novel ph responsive hydrogel and method of synthesis |
CN105596289A (zh) * | 2015-12-29 | 2016-05-25 | 华南理工大学 | 一种药物缓释水凝胶载体及其制备方法与应用 |
CN105658204A (zh) * | 2013-10-29 | 2016-06-08 | 华斯泰株式会社 | 将含有活性成分的脂质体物理性地包合在水凝胶粒子的方法及含有其的化妆品组合物 |
US20160331868A1 (en) * | 2015-05-14 | 2016-11-17 | California Institute Of Technology | Light adjustable intraocular lenses using upconverting nanoparticles and near infrared (nir) light |
CN106317263A (zh) * | 2016-08-23 | 2017-01-11 | 浙江理工大学 | 一种医用光固化水凝胶中可见光引发体系及其光固化方法 |
CN106986967A (zh) * | 2017-04-14 | 2017-07-28 | 浙江理工大学 | 一种可见光引发一步法制备具有双交联网络结构海藻酸钠复合水凝胶的方法 |
CN107236135A (zh) * | 2017-07-07 | 2017-10-10 | 中国科学院理化技术研究所 | 一种明胶水凝胶及其制备方法和应用 |
-
2018
- 2018-04-02 CN CN201810283134.7A patent/CN108467464A/zh active Pending
Patent Citations (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4628078A (en) * | 1984-06-12 | 1986-12-09 | Allied Colloids Ltd. | Acrylamide-dialkylaminoacrylate-dialkylaminomethacrylate cationic polyelectrolytes and their production |
US4963348A (en) * | 1987-12-11 | 1990-10-16 | The Procter & Gamble Company | Styling agents and compositions containing the same |
CN1072843A (zh) * | 1991-10-16 | 1993-06-09 | 理查森-维克斯有限公司 | 凝胶型化妆品组合物 |
CN1091317A (zh) * | 1992-07-28 | 1994-08-31 | 普罗格特-甘布尔公司 | 改进药品的局部输入 |
CN1382165A (zh) * | 1999-10-25 | 2002-11-27 | 庄臣及庄臣视力保护公司 | 制备光学品质聚合物的方法 |
CN101511339A (zh) * | 2005-08-04 | 2009-08-19 | 因滕迪斯有限公司 | 无水多相凝胶体系 |
CN1730515A (zh) * | 2005-08-26 | 2006-02-08 | 徐州恩华药业集团有限责任公司 | 一种制备水凝胶的方法 |
CN101466358A (zh) * | 2006-06-15 | 2009-06-24 | 帝斯曼知识产权资产管理有限公司 | 在敏感药物化合物的存在下通过辐射制备聚合基质的方法 |
CN101302264A (zh) * | 2007-05-11 | 2008-11-12 | 北京化工大学 | 一种含不饱和双键的聚合物乳液及其制备方法 |
CN101186706A (zh) * | 2007-11-15 | 2008-05-28 | 天津大学 | 一种peg系凝胶纳米颗粒的制备方法 |
CN101885906A (zh) * | 2010-07-17 | 2010-11-17 | 厦门大学 | 一种可降解生物水凝胶及其制备方法 |
CN102639097A (zh) * | 2011-03-21 | 2012-08-15 | 博任达生化科技(上海)有限公司 | 逆向温敏可逆水凝胶组合物 |
CN102250263A (zh) * | 2011-05-05 | 2011-11-23 | 北京化工大学 | 一种利用紫外光聚合在低温下制备高分子结晶的方法 |
CN105658204A (zh) * | 2013-10-29 | 2016-06-08 | 华斯泰株式会社 | 将含有活性成分的脂质体物理性地包合在水凝胶粒子的方法及含有其的化妆品组合物 |
WO2016028237A1 (en) * | 2014-08-22 | 2016-02-25 | Koç Üniversitesi | A novel ph responsive hydrogel and method of synthesis |
US20160331868A1 (en) * | 2015-05-14 | 2016-11-17 | California Institute Of Technology | Light adjustable intraocular lenses using upconverting nanoparticles and near infrared (nir) light |
CN105596289A (zh) * | 2015-12-29 | 2016-05-25 | 华南理工大学 | 一种药物缓释水凝胶载体及其制备方法与应用 |
CN106317263A (zh) * | 2016-08-23 | 2017-01-11 | 浙江理工大学 | 一种医用光固化水凝胶中可见光引发体系及其光固化方法 |
CN106986967A (zh) * | 2017-04-14 | 2017-07-28 | 浙江理工大学 | 一种可见光引发一步法制备具有双交联网络结构海藻酸钠复合水凝胶的方法 |
CN107236135A (zh) * | 2017-07-07 | 2017-10-10 | 中国科学院理化技术研究所 | 一种明胶水凝胶及其制备方法和应用 |
Non-Patent Citations (2)
Title |
---|
薛巍 等主编: "《生物医用水凝胶》", 31 December 2012, 暨南大学出版社 * |
魏忠诚 主编: "《光纤材料制备技术》", 30 September 2016, 北京邮电大学出版社 * |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN112538173A (zh) * | 2019-09-23 | 2021-03-23 | 天津大学 | 甲基丙烯酸羟乙酯基本体聚合水凝胶及其制备方法 |
CN112480308A (zh) * | 2020-11-25 | 2021-03-12 | 复旦大学 | 一种智能水凝胶及其制备方法 |
CN113521382A (zh) * | 2021-07-26 | 2021-10-22 | 台山市弘毅医疗用品有限公司 | 一种生物医用抗菌复合水凝胶的制备方法 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN108467464A (zh) | 含壬二酸可见光固化水凝胶及其制备方法 | |
US7045559B2 (en) | Electrically conductive adhesive hydrogels with solubilizer | |
CN105732848B (zh) | 一种光固化树脂及亲水润滑涂层与制备方法 | |
Mironi-Harpaz et al. | Photopolymerization of cell-encapsulating hydrogels: crosslinking efficiency versus cytotoxicity | |
US20050136077A1 (en) | Electrically conductive adhesive hydrogels with two initiators | |
CA2588700C (en) | Process for making pressure sensitive adhesive hydrogels | |
EP2112903B1 (en) | Electrically conductive hydrogels | |
JP4693434B2 (ja) | 歯科用粘膜調整材 | |
Suhail et al. | Development and characterization of pH-sensitive chondroitin sulfate-co-poly (acrylic acid) hydrogels for controlled release of diclofenac sodium | |
JP2002536091A (ja) | 生体接着剤組成物 | |
JP2005514386A5 (zh) | ||
US20070299206A1 (en) | Lactam polymer derivatives | |
US20050136023A1 (en) | Electrically conductive adhesive hydrogels with a thermally activated chemical initiator | |
JP2009221171A (ja) | 歯科用硬化性材料 | |
EP2029641A2 (en) | Lactam polymer derivatives | |
JP2004182661A (ja) | 歯科用レジン強化型セメント用前処理剤 | |
Lacerda‐Santos et al. | In vivo biocompatibility versus degree of conversion of resin‐reinforced cements in different time periods | |
JP4955007B2 (ja) | ブレンド型光硬化型キトサン系接着剤または被覆剤 | |
SE9600046D0 (sv) | New pharmaceutical formulation | |
JP4222517B2 (ja) | 高吸収性ポリマーの合成法 | |
Jay et al. | Formulation and evaluation of film forming gel of bifonazole for local drug delivery | |
CN114516925B (zh) | 一种基于含氮杂环酮类化合物的光聚合引发体系及其光聚合方法 | |
CN103509145A (zh) | 一种可见光和pH响应性自组装聚合物材料的制备方法 | |
CN106674425B (zh) | 一种pH响应缓释万古霉素的纳米微球的制备方法 | |
JPS6379818A (ja) | マイクロカプセル剤の製造方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
RJ01 | Rejection of invention patent application after publication | ||
RJ01 | Rejection of invention patent application after publication |
Application publication date: 20180831 |