CN110964498A - 一种热致变色胶囊及其制备方法 - Google Patents
一种热致变色胶囊及其制备方法 Download PDFInfo
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- CN110964498A CN110964498A CN201911288333.8A CN201911288333A CN110964498A CN 110964498 A CN110964498 A CN 110964498A CN 201911288333 A CN201911288333 A CN 201911288333A CN 110964498 A CN110964498 A CN 110964498A
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- TWFQJFPTTMIETC-UHFFFAOYSA-N dodecan-1-amine;hydron;chloride Chemical compound [Cl-].CCCCCCCCCCCC[NH3+] TWFQJFPTTMIETC-UHFFFAOYSA-N 0.000 claims description 3
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 claims description 3
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- DVBJBNKEBPCGSY-UHFFFAOYSA-M cetylpyridinium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+]1=CC=CC=C1 DVBJBNKEBPCGSY-UHFFFAOYSA-M 0.000 description 2
- MMKRHZKQPFCLLS-UHFFFAOYSA-N ethyl myristate Chemical compound CCCCCCCCCCCCCC(=O)OCC MMKRHZKQPFCLLS-UHFFFAOYSA-N 0.000 description 2
- MVLVMROFTAUDAG-UHFFFAOYSA-N ethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC MVLVMROFTAUDAG-UHFFFAOYSA-N 0.000 description 2
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- QSQLTHHMFHEFIY-UHFFFAOYSA-N methyl behenate Chemical compound CCCCCCCCCCCCCCCCCCCCCC(=O)OC QSQLTHHMFHEFIY-UHFFFAOYSA-N 0.000 description 2
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- 241001154287 Hucho taimen Species 0.000 description 1
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 1
- GYBGISCHRVNSSC-UHFFFAOYSA-N [Na].CCCCCCCCCCCCOS(=O)(=O)OC Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)OC GYBGISCHRVNSSC-UHFFFAOYSA-N 0.000 description 1
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- 125000001931 aliphatic group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
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- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- CAMHHLOGFDZBBG-UHFFFAOYSA-N epoxidized methyl oleate Natural products CCCCCCCCC1OC1CCCCCCCC(=O)OC CAMHHLOGFDZBBG-UHFFFAOYSA-N 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
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- 229940051841 polyoxyethylene ether Drugs 0.000 description 1
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K9/00—Tenebrescent materials, i.e. materials for which the range of wavelengths for energy absorption is changed as a result of excitation by some form of energy
- C09K9/02—Organic tenebrescent materials
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
- B01J13/02—Making microcapsules or microballoons
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Dispersion Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
- Manufacturing Of Micro-Capsules (AREA)
Abstract
本发明提供一种热致变色胶囊及其制备方法,所述胶囊的囊芯由溶剂、热致变色染料、显色剂、增感剂和防沉降剂组成。该胶囊的制备方法如下:将溶剂、热致变色染料、显色剂和增感剂加热溶解至澄清后,加入防沉降剂搅拌至均匀,制得囊芯;将囊芯加入到含有乳化剂的水溶液中乳化制得乳液,加入胶囊壳层预聚体,恒温反应,抽滤、清洗、干燥,制得胶囊。本发明涉及的热致变色胶囊具有良好储能调温及温度可视化显示的作用,防沉降剂的加入保证芯材组分均匀稳定地分散在胶囊内部,有效避免了多次冷热循环后热致变色染料团聚造成胶囊变色能力下降的现象。本发明所述的合成工艺简单,对设备要求低,反应条件容易控制,方便规模化生产,具有广大的应用前景。
Description
技术领域
本发明涉及胶囊领域,具体涉及一种热致变色胶囊的制备方法。
背景技术
热致变色材料是指在受热或冷却是发生颜色变化的材料,通过材料的颜色变化将周围环境温度的变化可视化。热致变色材料根据工艺配方的不同,可得到各种变色温度和各种不同的颜色,可以可逆变色或不可逆变色。这种高技术材料可调配成变色油墨、油漆、涂料,也可以成为纤维染料,进而延伸出许多用途,具有广阔的应用前景。热致变色材料主要可以分为无机物、有机物、聚合物和液晶共四类,无机物热致变色材料虽然有较好的耐温性,但是可逆性和灵敏性较差,变色温度偏高,在低温领域使用受到限制。聚合物和液晶热致变色材料工艺较复杂,成本较高,不利于广泛推广。有机物热致变色材料生产工艺简单,适用范围广,方便广泛应用。
有机物热致变色材料最常见的就是将热致变色染料及热致变色显色剂溶解于相变物质,当相变物质凝固时,热致变色染料及热致变色显色剂析出并接触而显色,当相变物质熔融,热致变色染料及热致变色显色剂溶解分离而褪色,通过控制相变物质的熔点来调节变色温度。利用微胶囊技术包覆上述热致变色体系,可有效避免相变物质熔融是发生泄漏,方便其应用。专利 CN201910030657.5中,李伟等人将显色剂和隐色剂溶于相变材料溶剂,制备温敏变色胶囊。专利CN201880007865.7中,德布拉威尔等人将电子给体有机染料化合物、电子受体化合物以及作为溶剂的化合物进行了胶囊化,用于墨水组合物。专利CN201811635267.2中,王朝霞等人将隐色体染料、电子受体化合物和溶剂混合后,利用正硅酸四乙酯、硅烷偶联剂和乳化剂制得热致变色硅胶囊颗粒。专利CN201510408001.4中,曹从军等人利用结晶紫内酯、双酚A、十六醇、三聚氰胺、甲醛制备了可逆热致变色微胶囊。专利CN201510217133.9中,郑立辉等人利用丙烯酸类、丙烯酸酯类或乙烯基类物质制备胶囊壁材,包覆含有隐色染料、显色剂和溶剂组成的芯材,制得有机可逆热致变色微胶囊。专利CN201010572467.5中,党一哲等人利用密胺树脂预聚体包覆由发色剂、显色剂和溶剂组成的热敏变色复配物芯材,制得热敏变色微胶囊。上述专利所述胶囊均具有良好的变色效果,但是,随着反复冷热循环,热致变色染料及热致变色显色剂会逐步向胶囊中心聚集,从而影响材料的变色性能。
发明内容
为解决现有热致变色材料重复使用后变色能力下降的问题,本发明提供了一种热致变色胶囊及其制备方法。
一种热致变色胶囊,所述胶囊的囊芯由溶剂、热致变色染料、显色剂、增感剂和防沉降剂组成。
所述的溶剂为脂肪酸酯、烷烃、脂肪醇中的任意一种或几种混合物。
所述的热致变色染料包括2-苯氨基-3-甲基-6-二乙基荧烷、2-苯氨基-3- 甲基-6-二丁基荧烷、3,3-双(N-辛基-2-甲基吲哚)邻苯二甲内酯、结晶紫内酯、 3,3-二(4-二乙基氨基-2-乙氧基苯基)-4-氮杂苯酞、4,4-[(9-丁基-9H-咔唑 -3-基)亚甲基]双[N-甲基-N-苯基苯胺]、1,3-二甲基-6-二乙氨基荧烷、2’-氯 -6’-(二乙氨基)荧烷、7-[4-(二乙基氨基)-2-乙氧基苯基]-7-(2-甲基-1-辛基 -1H-吲哚-3-基)呋喃并[3,4-B]吡啶-5(7H)-酮中的一种或两种以上的组合物。
所述的热致变色显色剂为双酚A、双酚F、双酚S、2,4-二苯砜基苯酚、4,4’- 磺酰基双[2-(2-丙烯基)]苯酚中的至少一种。
所述的增感剂包括芳香族或脂肪族的酯类,具体为1-羟基-2萘甲酸苯酯、乙二酸二苄酯、对苄基联苯中的至少一种。
所述的防沉降剂是由多种物质组成混合物M,主体成分是丙烯酸酯类,其通式为
式中R为环己基、苯及其衍生物基团或含有1-10个碳原子的饱和烷烃基团中的至少一种。
一种热致变色胶囊的制备方法,包含以下步骤:
1)按质量份计,100份的溶剂,0.1-10份的热致变色染料、0.1-10份的显色剂、0-5份的增感剂后加热溶解,再加入1-20份的防沉降剂,继续搅拌至均匀透明,制得分散相;
2)将分散相缓慢加入到含有0.5-20wt%的乳化剂水溶液中,机械或超声乳化制得水包油型乳液后,缓慢加入胶囊壁材预聚体,50-95℃恒温1h-8h后,抽滤、清洗、干燥,制得热致变色胶囊。
所述的乳化剂为烷基酚聚氧乙烯醚、高碳醇脂肪醇聚氧乙烯醚、脂肪酸聚氧乙烯酯、聚丙烯酸、聚丙烯酸钠、聚丙烯酰胺和苯乙烯马来酸酐共聚物钠盐、苯乙烯马来酸酐共聚物钠盐、苯乙烯马来酸酐共聚物、十二烷基氯化铵、十六烷基三甲基溴化铵、十六烷基溴化吡啶、十二烷基苯磺酸钠、十二甲基硫酸钠中的至少一种。
所述的胶囊壁材预聚体为密胺预聚体,脲醛预聚体中至少一种。
本发明在囊芯中添加防沉降剂,可以在胶囊内部形成类骨架状结构,保证芯材组分均匀稳定地分散在胶囊内部,有效避免了多次冷热循环后热致变色染料和热致变色显色剂在胶囊中心聚集造成胶囊变色能力下降的问题。本发明所述的合成工艺简单,对设备要求低,反应条件容易控制,方便规模化生产,具有广大的应用前景。
具体实施方式
下面结合具体实施例对本发明作进一步说明。
实施例1
1)按质量份计,100份的十四醇,加入0.1份的2-苯氨基-3-甲基-6-二乙基荧烷、0.1份的双酚A后加热溶解,再加入15份的防沉降剂,继续搅拌至均匀透明,制得分散相;
2)将分散相缓慢加入到含有0.5wt%的聚丙烯酸钠水溶液中,机械乳化制得水包油型乳液后,缓慢加入密胺预聚体,50℃恒温8h后,抽滤、清洗、干燥,制得热致变色胶囊。
实施例2
1)按质量份计,100份的十八醇,加入4份的2-苯氨基-3-甲基-6-二乙基荧烷、9份的双酚F、0.5份对苄基联苯后加热溶解,再加入3份的防沉降剂,继续搅拌至均匀透明,制得分散相;
2)将分散相缓慢加入到含有3wt%的聚丙烯酰胺和苯乙烯马来酸酐共聚物钠盐水溶液中,机械乳化制得水包油型乳液后,缓慢加入密胺预聚体,55℃恒温7 h后,抽滤、清洗、干燥,制得热致变色胶囊。
实施例3
1)按质量份计,100份的硬脂酸甲酯,加入10份的3,3-双(N-辛基-2-甲基吲哚)邻苯二甲内酯、8份的双酚S、1.5份1-羟基-2萘甲酸苯酯后加热溶解,再加入5份的防沉降剂,继续搅拌至均匀透明,制得分散相;
2)将分散相缓慢加入到含有5wt%的苯乙烯马来酸酐共聚物钠盐水溶液中,机械乳化制得水包油型乳液后,缓慢加入脲醛预聚体,60℃恒温6h后,抽滤、清洗、干燥,制得热致变色胶囊。
实施例4
1)按质量份计,100份的肉豆蔻酸甲酯,加入7份的结晶紫内酯、6份的2,4- 二苯砜基苯酚、2.5份乙二酸二苄酯后加热溶解,再加入10份的防沉降剂,继续搅拌至均匀透明,制得分散相;
2)将分散相缓慢加入到含有7wt%的十二烷基氯化铵水溶液中,机械乳化制得水包油型乳液后,缓慢加入脲醛预聚体,65℃恒温5h后,抽滤、清洗、干燥,制得热致变色胶囊。
实施例5
1)按质量份计,100份的棕榈酸甲酯,加入6份的3,3-二(4-二乙基氨基-2- 乙氧基苯基)-4-氮杂苯酞、4份的4,4’-磺酰基双[2-(2-丙烯基)]苯酚后加热溶解,再加入15份的防沉降剂,继续搅拌至均匀透明,制得分散相;
2)将分散相缓慢加入到含有9wt%的十六烷基三甲基溴化铵水溶液中,机械乳化制得水包油型乳液后,缓慢加入密胺预聚体,70℃恒温4h后,抽滤、清洗、干燥,制得热致变色胶囊。
实施例6
1)按质量份计,100份的十八烷,加入8份的4,4-[(9-丁基-9H-咔唑-3- 基)亚甲基]双[N-甲基-N-苯基苯胺]、10份的双酚S、3.5份1-羟基-2萘甲酸苯酯后加热溶解,再加入20份的防沉降剂,继续搅拌至均匀透明,制得分散相;
2)将分散相缓慢加入到含有11wt%的十六烷基溴化吡啶水溶液中,超声乳化制得水包油型乳液后,缓慢加入脲醛预聚体,80℃恒温3h后,抽滤、清洗、干燥,制得热致变色胶囊。
实施例7
1)按质量份计,100份的十六烷,加入3份的1,3-二甲基-6-二乙氨基荧烷、 7份的双酚F后加热溶解,再加入18份的防沉降剂,继续搅拌至均匀透明,制得分散相;
2)将分散相缓慢加入到含有13wt%的十二烷基苯磺酸钠水溶液中,机械乳化制得水包油型乳液后,缓慢加入密胺预聚体,85℃恒温2h后,抽滤、清洗、干燥,制得热致变色胶囊。
实施例8
1)按质量份计,100份的硬脂酸乙酯,加入5份的2’-氯-6’-(二乙氨基)荧烷、3份的双酚A、4.5份乙二酸二苄酯后加热溶解,再加入12份的防沉降剂,继续搅拌至均匀透明,制得分散相;
2)将分散相缓慢加入到含有16wt%的十二甲基硫酸钠水溶液中,机械乳化制得水包油型乳液后,缓慢加入脲醛预聚体,90℃恒温1h后,抽滤、清洗、干燥,制得热致变色胶囊。
实施例9
1)按质量份计,100份的肉豆蔻酸乙酯,加入2份的7-[4-(二乙基氨基)-2- 乙氧基苯基]-7-(2-甲基-1-辛基-1H-吲哚-3-基)呋喃并[3,4-B]吡啶-5(7H)-酮、1份的4,4’-磺酰基双[2-(2-丙烯基)]苯酚、5份对苄基联苯后加热溶解,再加入7份的防沉降剂,继续搅拌至均匀透明,制得分散相;
2)将分散相缓慢加入到含有18wt%的脂肪酸聚氧乙烯酯水溶液中,机械乳化制得水包油型乳液后,缓慢加入密胺预聚体,95℃恒温3h后,抽滤、清洗、干燥,制得热致变色胶囊。
实施例10
1)按质量份计,100份的山嵛酸甲酯,加入1份的结晶紫内酯、5份的双酚 A、1.5份1-羟基-2萘甲酸苯酯后加热溶解,再加入1份的防沉降剂,继续搅扦至均匀透明,制得分散相;
2)将分散相缓慢加入到含有20wt%的十二甲基硫酸钠水溶液中,机械乳化制得水包油型乳液后,缓慢加入脲醛预聚体,60℃恒温6h后,抽滤、清洗、干燥,制得热致变色胶囊。
以上所述的具体实施方式,对本发明的目的、技术方案和有益效果进行了进一步详细说明,所应理解的是,以上所述仅为本发明的具体实施方式而已,并不用于限制本发明,凡在本发明的精神和原则之内,所做的任何修改、等同替换、改进等,均应包含在本发明的保护范围之内。
Claims (9)
1.一种热致变色胶囊,其特征在于所述胶囊的囊芯由溶剂、热致变色染料、显色剂、增感剂和防沉降剂组成。
2.如权利要求1所述的热致变色胶囊,其特征在于所述的溶剂为脂肪酸酯、烷烃、脂肪醇中的任意一种或几种混合物。
3.如权利要求1所述的热致变色胶囊,其特征在于所述的热致变色染料包括2-苯氨基-3-甲基-6-二乙基荧烷、2-苯氨基-3-甲基-6-二丁基荧烷、3,3-双(N-辛基-2-甲基吲哚)邻苯二甲内酯、结晶紫内酯、3,3-二(4-二乙基氨基-2-乙氧基苯基)-4-氮杂苯酞、4,4-[(9-丁基-9H-咔唑-3-基)亚甲基]双[N-甲基-N-苯基苯胺]、1,3-二甲基-6-二乙氨基荧烷、2’-氯-6’-(二乙氨基)荧烷、7-[4-(二乙基氨基)-2-乙氧基苯基]-7-(2-甲基-1-辛基-1H-吲哚-3-基)呋喃并[3,4-B]吡啶-5(7H)-酮中的一种或两种以上的组合物。
4.如权利要求1所述的热致变色胶囊,其特征在于所述的热致变色显色剂为双酚A、双酚F、双酚S、2,4-二苯砜基苯酚、4,4’-磺酰基双[2-(2-丙烯基)]苯酚中的至少一种。
5.如权利要求1所述的热致变色胶囊,其特征在于所述的增感剂包括芳香族或脂肪族的酯类,具体为1-羟基-2萘甲酸苯酯、乙二酸二苄酯、对苄基联苯中的至少一种。
7.一种热致变色胶囊的制备方法,其特征在于包含以下步骤:
1)按质量份计,100份的溶剂,0.1-10份的热致变色染料、0.1-10份的显色剂、0-5份的增感剂后加热溶解,再加入1-20份的防沉降剂,继续搅拌至均匀透明,制得分散相;
2)将分散相缓慢加入到含有0.1-20wt%的乳化剂水溶液中,机械或超声乳化制得水包油型乳液后,缓慢加入胶囊壁材预聚体,50-95℃恒温1h-8h后,抽滤、清洗、干燥,制得热致变色胶囊。
8.如权利要求7所述的制备方法,其特征在于所述的乳化剂为烷基酚聚氧乙烯醚、高碳醇脂肪醇聚氧乙烯醚、脂肪酸聚氧乙烯酯、聚丙烯酸、聚丙烯酸钠、聚丙烯酰胺和苯乙烯马来酸酐共聚物钠盐、苯乙烯马来酸酐共聚物钠盐、苯乙烯马来酸酐共聚物、十二烷基氯化铵、十六烷基三甲基溴化铵、十六烷基溴化吡啶、十二烷基苯磺酸钠、十二甲基硫酸钠中的至少一种。
9.如权利要求7所述的制备方法,其特征在于所述的胶囊壁材预聚体为密胺预聚体、脲醛预聚体中至少一种。
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CN112852402A (zh) * | 2020-12-22 | 2021-05-28 | 厦门安踏体育用品有限公司 | 一种持久温致变色材料、其制备方法和在纺织品中的应用 |
CN112852402B (zh) * | 2020-12-22 | 2023-06-23 | 厦门安踏体育用品有限公司 | 一种持久温致变色材料、其制备方法和在纺织品中的应用 |
CN113956510A (zh) * | 2021-11-29 | 2022-01-21 | 浙江大学 | 基于温敏变色微胶囊夹杂的温敏变色水凝胶材料及其制备方法 |
CN114316941A (zh) * | 2021-12-23 | 2022-04-12 | 天津大学 | 一种高稳定性的四元亲水性仿生有机热致变色体系 |
CN115466611A (zh) * | 2022-10-13 | 2022-12-13 | 中国南方电网有限责任公司超高压输电公司天生桥局 | 热致变色颗粒及其制备方法、热致变色涂料及其应用 |
CN117085603A (zh) * | 2023-10-18 | 2023-11-21 | 清华大学 | 一种实时监测运动副失效的方法 |
CN117085603B (zh) * | 2023-10-18 | 2023-12-29 | 清华大学 | 一种实时监测运动副失效的方法 |
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