KR102371793B1 - 저 잔류 유리 포름알데하이드 마이크로캡슐의 제조 방법 및 이를 이용하여 제조된 마이크로캡슐 - Google Patents
저 잔류 유리 포름알데하이드 마이크로캡슐의 제조 방법 및 이를 이용하여 제조된 마이크로캡슐 Download PDFInfo
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- KR102371793B1 KR102371793B1 KR1020217023345A KR20217023345A KR102371793B1 KR 102371793 B1 KR102371793 B1 KR 102371793B1 KR 1020217023345 A KR1020217023345 A KR 1020217023345A KR 20217023345 A KR20217023345 A KR 20217023345A KR 102371793 B1 KR102371793 B1 KR 102371793B1
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- Prior art keywords
- less
- ppm
- free formaldehyde
- polymer wall
- formaldehyde
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- 238000000034 method Methods 0.000 title claims abstract description 71
- 239000003094 microcapsule Substances 0.000 title claims abstract description 50
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 title claims description 306
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 98
- 229920000877 Melamine resin Polymers 0.000 claims abstract description 91
- 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 abstract description 72
- -1 aliphatic aldehyde Chemical class 0.000 claims abstract description 41
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 41
- ZMGMDXCADSRNCX-UHFFFAOYSA-N 5,6-dihydroxy-1,3-diazepan-2-one Chemical compound OC1CNC(=O)NCC1O ZMGMDXCADSRNCX-UHFFFAOYSA-N 0.000 claims abstract description 29
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 25
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- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims abstract description 13
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- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 abstract description 9
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- 239000002904 solvent Substances 0.000 description 4
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
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- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 3
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- VPVSTMAPERLKKM-UHFFFAOYSA-N glycoluril Chemical compound N1C(=O)NC2NC(=O)NC21 VPVSTMAPERLKKM-UHFFFAOYSA-N 0.000 description 3
- 238000005338 heat storage Methods 0.000 description 3
- YCOZIPAWZNQLMR-UHFFFAOYSA-N heptane - octane Natural products CCCCCCCCCCCCCCC YCOZIPAWZNQLMR-UHFFFAOYSA-N 0.000 description 3
- 230000003301 hydrolyzing effect Effects 0.000 description 3
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Classifications
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- 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
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- 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
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- B01J13/14—Polymerisation; cross-linking
- B01J13/18—In situ polymerisation with all reactants being present in the same phase
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- 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
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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
- 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
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-
- 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
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Applications Claiming Priority (4)
| 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 |
| KR1020187006933A KR102371790B1 (ko) | 2015-08-18 | 2016-08-18 | 저 잔류 유리 포름알데하이드 마이크로캡슐의 제조 방법 및 이를 이용하여 제조된 마이크로캡슐 |
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| KR1020187006933A Division KR102371790B1 (ko) | 2015-08-18 | 2016-08-18 | 저 잔류 유리 포름알데하이드 마이크로캡슐의 제조 방법 및 이를 이용하여 제조된 마이크로캡슐 |
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| KR20210100192A KR20210100192A (ko) | 2021-08-13 |
| KR102371793B1 true KR102371793B1 (ko) | 2022-03-07 |
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| KR1020217023345A Active KR102371793B1 (ko) | 2015-08-18 | 2016-08-18 | 저 잔류 유리 포름알데하이드 마이크로캡슐의 제조 방법 및 이를 이용하여 제조된 마이크로캡슐 |
| KR1020187006933A Active KR102371790B1 (ko) | 2015-08-18 | 2016-08-18 | 저 잔류 유리 포름알데하이드 마이크로캡슐의 제조 방법 및 이를 이용하여 제조된 마이크로캡슐 |
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| US (2) | US10005059B2 (enExample) |
| EP (1) | EP3337604B1 (enExample) |
| JP (2) | JP2018523749A (enExample) |
| KR (2) | KR102371793B1 (enExample) |
| CN (1) | CN108025277A (enExample) |
| WO (1) | WO2017031321A1 (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR102371793B1 (ko) * | 2015-08-18 | 2022-03-07 | 마이크로텍 라보라토리즈, 인코포레이티드 | 저 잔류 유리 포름알데하이드 마이크로캡슐의 제조 방법 및 이를 이용하여 제조된 마이크로캡슐 |
| 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 |
| JP7760510B2 (ja) | 2020-01-31 | 2025-10-27 | ダウ グローバル テクノロジーズ エルエルシー | コーティングされたポリウレタン発泡体 |
| US20230114154A1 (en) | 2020-04-09 | 2023-04-13 | Dow Global Technologies Llc | Coated sponges |
| WO2021262653A1 (en) * | 2020-06-23 | 2021-12-30 | Microtek Laboratories,Inc. | A 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 |
| EP4286434A4 (en) * | 2021-01-29 | 2025-01-15 | Kagoshima University | Novel fine hollow particles comprising melamine-based resin |
| EP4486838A1 (en) | 2022-03-03 | 2025-01-08 | 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 |
Citations (4)
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|---|---|---|---|---|
| WO2008151941A1 (en) | 2007-06-12 | 2008-12-18 | Basf Se | Microcapsules, their use and processes for their manufacture |
| US20130189438A1 (en) | 2010-09-30 | 2013-07-25 | Ram B. Gupta | Mixtures of crosslinking agents |
| 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 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| ES2017536T5 (es) * | 1987-12-21 | 1995-08-01 | Koehler August Papierfab | Procedimiento para la fabricacion de microcapsulas, microcapsulas obtenidas y su utilizacion. |
| US5415222A (en) | 1993-11-19 | 1995-05-16 | Triangle Research & Development Corporation | Micro-climate cooling garment |
| AU2001294772A1 (en) | 2000-09-27 | 2002-04-08 | Microtek Laboratories, Inc. | Macrocapsules containing microencapsulated phase change materials |
| ES2662421T3 (es) | 2013-01-22 | 2018-04-06 | The Procter & Gamble Company | Composiciones tratantes que comprenden microcápsulas, aminas primarias o secundarias y eliminadores de formaldehído |
| KR102371793B1 (ko) * | 2015-08-18 | 2022-03-07 | 마이크로텍 라보라토리즈, 인코포레이티드 | 저 잔류 유리 포름알데하이드 마이크로캡슐의 제조 방법 및 이를 이용하여 제조된 마이크로캡슐 |
-
2016
- 2016-08-18 KR KR1020217023345A patent/KR102371793B1/ko active Active
- 2016-08-18 JP JP2018528206A patent/JP2018523749A/ja active Pending
- 2016-08-18 WO PCT/US2016/047559 patent/WO2017031321A1/en not_active Ceased
- 2016-08-18 EP EP16837841.2A patent/EP3337604B1/en active Active
- 2016-08-18 US US15/240,435 patent/US10005059B2/en active Active
- 2016-08-18 CN CN201680047811.4A patent/CN108025277A/zh active Pending
- 2016-08-18 KR KR1020187006933A patent/KR102371790B1/ko active Active
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2018
- 2018-05-29 US US15/991,839 patent/US10287470B2/en active Active
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2020
- 2020-06-10 JP JP2020100906A patent/JP2020151713A/ja active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008151941A1 (en) | 2007-06-12 | 2008-12-18 | Basf Se | Microcapsules, their use and processes for their manufacture |
| US20130189438A1 (en) | 2010-09-30 | 2013-07-25 | Ram B. Gupta | Mixtures of crosslinking agents |
| 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| KR20210100192A (ko) | 2021-08-13 |
| US10287470B2 (en) | 2019-05-14 |
| US10005059B2 (en) | 2018-06-26 |
| EP3337604A1 (en) | 2018-06-27 |
| US20170065956A1 (en) | 2017-03-09 |
| JP2020151713A (ja) | 2020-09-24 |
| CN108025277A (zh) | 2018-05-11 |
| JP2018523749A (ja) | 2018-08-23 |
| EP3337604A4 (en) | 2019-04-24 |
| US20180273820A1 (en) | 2018-09-27 |
| WO2017031321A1 (en) | 2017-02-23 |
| EP3337604B1 (en) | 2021-03-24 |
| KR20180041157A (ko) | 2018-04-23 |
| KR102371790B1 (ko) | 2022-03-07 |
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