CN108025277A - 制备低残留游离甲醛微胶囊的方法和通过其制备的微胶囊 - Google Patents
制备低残留游离甲醛微胶囊的方法和通过其制备的微胶囊 Download PDFInfo
- Publication number
- CN108025277A CN108025277A CN201680047811.4A CN201680047811A CN108025277A CN 108025277 A CN108025277 A CN 108025277A CN 201680047811 A CN201680047811 A CN 201680047811A CN 108025277 A CN108025277 A CN 108025277A
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- China
- Prior art keywords
- formaldehyde
- cross
- linking reagent
- melamino
- capsule
- 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
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- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 title claims abstract description 333
- 239000003094 microcapsule Substances 0.000 title claims abstract description 53
- 238000000034 method Methods 0.000 title claims description 73
- 238000002360 preparation method Methods 0.000 title description 6
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 135
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract description 117
- 239000004202 carbamide Substances 0.000 claims abstract description 63
- 239000011162 core material Substances 0.000 claims abstract description 48
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 41
- -1 aliphatic aldehyde aldehyde Chemical class 0.000 claims abstract description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 32
- 239000006210 lotion Substances 0.000 claims abstract description 31
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 30
- 239000004094 surface-active agent Substances 0.000 claims abstract description 22
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims abstract description 13
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims abstract description 9
- QQOWHRYOXYEMTL-UHFFFAOYSA-N triazin-4-amine Chemical class N=C1C=CN=NN1 QQOWHRYOXYEMTL-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims abstract description 8
- 150000001541 aziridines Chemical class 0.000 claims abstract description 8
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- 239000004593 Epoxy Substances 0.000 claims description 7
- IVJISJACKSSFGE-UHFFFAOYSA-N formaldehyde;1,3,5-triazine-2,4,6-triamine Chemical compound O=C.NC1=NC(N)=NC(N)=N1 IVJISJACKSSFGE-UHFFFAOYSA-N 0.000 claims description 6
- 238000001157 Fourier transform infrared spectrum Methods 0.000 claims description 5
- IWLBIFVMPLUHLK-UHFFFAOYSA-N azane;formaldehyde Chemical compound N.O=C IWLBIFVMPLUHLK-UHFFFAOYSA-N 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 3
- 239000000203 mixture Substances 0.000 abstract description 27
- 150000002118 epoxides Chemical class 0.000 abstract 1
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- 238000007792 addition Methods 0.000 description 36
- 150000001299 aldehydes Chemical class 0.000 description 32
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
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- 239000012071 phase Substances 0.000 description 19
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 18
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- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
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- 150000001412 amines Chemical class 0.000 description 3
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- POTBQYRUECIJLU-UHFFFAOYSA-N formaldehyde;1,3,5-triazine-2,4,6-triamine Chemical compound O=C.NC1=NC(N)=NC(N)=N1.NC1=NC(N)=NC(N)=N1 POTBQYRUECIJLU-UHFFFAOYSA-N 0.000 description 1
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- 229940074046 glyceryl laurate Drugs 0.000 description 1
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 1
- 125000001046 glycoluril group Chemical group [H]C12N(*)C(=O)N(*)C1([H])N(*)C(=O)N2* 0.000 description 1
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- 238000005338 heat storage Methods 0.000 description 1
- QGCFFOIZQAEOAQ-UHFFFAOYSA-M heptadecyl-hexadecyl-dimethylazanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCC QGCFFOIZQAEOAQ-UHFFFAOYSA-M 0.000 description 1
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 1
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- DEQLTFPCJRGSHW-UHFFFAOYSA-N hexadecylbenzene Chemical compound CCCCCCCCCCCCCCCCC1=CC=CC=C1 DEQLTFPCJRGSHW-UHFFFAOYSA-N 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
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- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000007037 hydroformylation reaction Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical class CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 229940070765 laurate Drugs 0.000 description 1
- PYIDGJJWBIBVIA-UYTYNIKBSA-N lauryl glucoside Chemical compound CCCCCCCCCCCCO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O PYIDGJJWBIBVIA-UYTYNIKBSA-N 0.000 description 1
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- CCRCUPLGCSFEDV-BQYQJAHWSA-N methyl trans-cinnamate Chemical compound COC(=O)\C=C\C1=CC=CC=C1 CCRCUPLGCSFEDV-BQYQJAHWSA-N 0.000 description 1
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- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
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- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- LQERIDTXQFOHKA-UHFFFAOYSA-N nonadecane Chemical compound CCCCCCCCCCCCCCCCCCC LQERIDTXQFOHKA-UHFFFAOYSA-N 0.000 description 1
- 239000002667 nucleating agent Substances 0.000 description 1
- 229940038384 octadecane Drugs 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 125000002811 oleoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 description 1
- 150000008104 phosphatidylethanolamines Chemical class 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 description 1
- 229920001289 polyvinyl ether Polymers 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 239000006041 probiotic Substances 0.000 description 1
- 230000000529 probiotic effect Effects 0.000 description 1
- 235000018291 probiotics Nutrition 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229940084106 spermaceti Drugs 0.000 description 1
- 239000012177 spermaceti Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 229940012831 stearyl alcohol Drugs 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
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- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- JZALLXAUNPOCEU-UHFFFAOYSA-N tetradecylbenzene Chemical compound CCCCCCCCCCCCCCC1=CC=CC=C1 JZALLXAUNPOCEU-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
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Classifications
-
- 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
- B01J13/06—Making microcapsules or microballoons by phase separation
- B01J13/14—Polymerisation; cross-linking
- B01J13/18—In situ polymerisation with all reactants being present in the same phase
-
- 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
- C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
- C09K5/02—Materials undergoing a change of physical state when used
- C09K5/06—Materials undergoing a change of physical state when used the change of state being from liquid to solid or vice versa
- C09K5/063—Materials absorbing or liberating heat during crystallisation; Heat storage 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
- B01J13/06—Making microcapsules or microballoons by phase separation
- B01J13/14—Polymerisation; cross-linking
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F28—HEAT EXCHANGE IN GENERAL
- F28D—HEAT-EXCHANGE APPARATUS, NOT PROVIDED FOR IN ANOTHER SUBCLASS, IN WHICH THE HEAT-EXCHANGE MEDIA DO NOT COME INTO DIRECT CONTACT
- F28D20/00—Heat storage plants or apparatus in general; Regenerative heat-exchange apparatus not covered by groups F28D17/00 or F28D19/00
- F28D20/02—Heat storage plants or apparatus in general; Regenerative heat-exchange apparatus not covered by groups F28D17/00 or F28D19/00 using latent heat
- F28D20/023—Heat storage plants or apparatus in general; Regenerative heat-exchange apparatus not covered by groups F28D17/00 or F28D19/00 using latent heat the latent heat storage material being enclosed in granular particles or dispersed in a porous, fibrous or cellular structure
-
- 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
- C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
- C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
- C08G12/26—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds
- C08G12/30—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds with substituted triazines
- C08G12/32—Melamines
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/14—Thermal energy storage
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Dispersion Chemistry (AREA)
- Thermal Sciences (AREA)
- Physics & Mathematics (AREA)
- Combustion & Propulsion (AREA)
- Materials Engineering (AREA)
- Mechanical Engineering (AREA)
- General Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Manufacturing Of Micro-Capsules (AREA)
- Phenolic Resins Or Amino Resins (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562206367P | 2015-08-18 | 2015-08-18 | |
| US62/206,367 | 2015-08-18 | ||
| PCT/US2016/047559 WO2017031321A1 (en) | 2015-08-18 | 2016-08-18 | Methods for making low remnant free formaldehyde microcapsules and microcapsules made by same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
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| EP3337604B1 (en) * | 2015-08-18 | 2021-03-24 | Microtek Laboratories, Inc. | Methods for making low remnant free formaldehyde microcapsules and microcapsules made by same |
| US10561182B2 (en) | 2017-02-28 | 2020-02-18 | Microtek Laboratories, Inc. | Moisture wicking and cooling capsules having an outer shell comprising a siloxane and methods for making same |
| WO2021154792A1 (en) | 2020-01-31 | 2021-08-05 | Dow Global Technologies Llc | Coated polyurethane foams |
| WO2021206784A1 (en) | 2020-04-09 | 2021-10-14 | Dow Global Technologies Llc | Coated sponges |
| US11920048B2 (en) | 2020-06-23 | 2024-03-05 | Microtek Laboratories Inc. | Non-flammable coating loaded with microcapsules encapsulating a flammable phase change material and layered structures made therewith |
| CN111821926B (zh) * | 2020-07-22 | 2022-08-09 | 襄阳三沃航天薄膜材料有限公司 | 一种低甲醛含量三聚氰胺相变微胶囊的制备方法 |
| US20240301171A1 (en) * | 2021-01-29 | 2024-09-12 | Kagoshima University | Novel fine hollow particles comprising melamine-based resin |
| WO2023167831A1 (en) | 2022-03-03 | 2023-09-07 | Dow Global Technologies Llc | Coated polyurethane foams |
| CN120225754A (zh) | 2022-12-20 | 2025-06-27 | 陶氏环球技术有限责任公司 | 具有凉爽表面特征的人造皮革 |
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| CN103154064A (zh) * | 2010-09-30 | 2013-06-12 | 氰特科技公司 | 交联剂混合物 |
| US20130264513A1 (en) * | 2012-04-09 | 2013-10-10 | Chung-Shan Institute of Science and Technology, Armaments, Bureau, Ministry of National Defense | Phase-changing material microcapsules by using pmma prepolymer and organic-solvent free synthesis process |
| CN103752241A (zh) * | 2014-01-24 | 2014-04-30 | 厦门大学 | 十二醇/三聚氰胺-甲醛树脂微胶囊相变材料的制备方法 |
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| JPS55119437A (en) * | 1979-03-07 | 1980-09-13 | Fuji Photo Film Co Ltd | Production of microcapsule dispersion |
| JPS61204035A (ja) * | 1985-03-07 | 1986-09-10 | Sumitomo Chem Co Ltd | マイクロカプセルの製法 |
| JPS63232838A (ja) * | 1987-03-19 | 1988-09-28 | Kanzaki Paper Mfg Co Ltd | マイクロカプセル分散液の製造方法 |
| EP0321750B2 (de) * | 1987-12-21 | 1993-03-24 | Papierfabrik August Koehler AG | Verfahren zur Herstellung von Mikrokapseln, die danach erhältlichen Mikrokapseln und deren Verwendung |
| US5415222A (en) | 1993-11-19 | 1995-05-16 | Triangle Research & Development Corporation | Micro-climate cooling garment |
| US6703127B2 (en) | 2000-09-27 | 2004-03-09 | Microtek Laboratories, Inc. | Macrocapsules containing microencapsulated phase change materials |
| US20100168275A1 (en) * | 2007-06-12 | 2010-07-01 | Zhao Chun-Tian | Microcapsules, their use and processes for their manufacture |
| EP2757146B1 (en) | 2013-01-22 | 2018-01-03 | The Procter & Gamble Company | Treatment compositions comprising microcapsules, primary or secondary amines, and formaldehyde scavengers |
| EP3337604B1 (en) * | 2015-08-18 | 2021-03-24 | Microtek Laboratories, Inc. | Methods for making low remnant free formaldehyde microcapsules and microcapsules made by same |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103154064A (zh) * | 2010-09-30 | 2013-06-12 | 氰特科技公司 | 交联剂混合物 |
| US20130264513A1 (en) * | 2012-04-09 | 2013-10-10 | Chung-Shan Institute of Science and Technology, Armaments, Bureau, Ministry of National Defense | Phase-changing material microcapsules by using pmma prepolymer and organic-solvent free synthesis process |
| CN103752241A (zh) * | 2014-01-24 | 2014-04-30 | 厦门大学 | 十二醇/三聚氰胺-甲醛树脂微胶囊相变材料的制备方法 |
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| KR102371793B1 (ko) | 2022-03-07 |
| EP3337604A1 (en) | 2018-06-27 |
| EP3337604B1 (en) | 2021-03-24 |
| JP2018523749A (ja) | 2018-08-23 |
| EP3337604A4 (en) | 2019-04-24 |
| US10005059B2 (en) | 2018-06-26 |
| WO2017031321A1 (en) | 2017-02-23 |
| US20170065956A1 (en) | 2017-03-09 |
| KR20180041157A (ko) | 2018-04-23 |
| KR102371790B1 (ko) | 2022-03-07 |
| US10287470B2 (en) | 2019-05-14 |
| JP2020151713A (ja) | 2020-09-24 |
| KR20210100192A (ko) | 2021-08-13 |
| US20180273820A1 (en) | 2018-09-27 |
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