CN114130320B - Electronic ink microcapsule, electronic ink, preparation method and flexible display screen - Google Patents
Electronic ink microcapsule, electronic ink, preparation method and flexible display screen Download PDFInfo
- Publication number
- CN114130320B CN114130320B CN202111236885.1A CN202111236885A CN114130320B CN 114130320 B CN114130320 B CN 114130320B CN 202111236885 A CN202111236885 A CN 202111236885A CN 114130320 B CN114130320 B CN 114130320B
- Authority
- CN
- China
- Prior art keywords
- electronic ink
- microcapsule
- wall material
- chain extender
- prepolymer
- 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.)
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- 239000003094 microcapsule Substances 0.000 title claims abstract description 64
- 238000002360 preparation method Methods 0.000 title abstract description 14
- 239000000463 material Substances 0.000 claims abstract description 44
- 239000002775 capsule Substances 0.000 claims abstract description 29
- -1 polysiloxane Polymers 0.000 claims abstract description 28
- 229920001296 polysiloxane Polymers 0.000 claims abstract description 23
- 229920002635 polyurethane Polymers 0.000 claims abstract description 11
- 239000004814 polyurethane Substances 0.000 claims abstract description 11
- 239000000243 solution Substances 0.000 claims description 19
- 239000000839 emulsion Substances 0.000 claims description 18
- 238000003756 stirring Methods 0.000 claims description 17
- 239000004970 Chain extender Substances 0.000 claims description 16
- 238000010438 heat treatment Methods 0.000 claims description 16
- 229920001730 Moisture cure polyurethane Polymers 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 13
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 12
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 12
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 10
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 claims description 8
- 125000003158 alcohol group Chemical group 0.000 claims description 8
- 150000001412 amines Chemical group 0.000 claims description 8
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 8
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims description 8
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 7
- 238000006116 polymerization reaction Methods 0.000 claims description 7
- PYSRRFNXTXNWCD-UHFFFAOYSA-N 3-(2-phenylethenyl)furan-2,5-dione Chemical compound O=C1OC(=O)C(C=CC=2C=CC=CC=2)=C1 PYSRRFNXTXNWCD-UHFFFAOYSA-N 0.000 claims description 6
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 6
- 229920000147 Styrene maleic anhydride Polymers 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 6
- 238000001035 drying Methods 0.000 claims description 6
- 238000001914 filtration Methods 0.000 claims description 6
- 239000000843 powder Substances 0.000 claims description 6
- 238000005406 washing Methods 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- IBOFVQJTBBUKMU-UHFFFAOYSA-N 4,4'-methylene-bis-(2-chloroaniline) Chemical compound C1=C(Cl)C(N)=CC=C1CC1=CC=C(N)C(Cl)=C1 IBOFVQJTBBUKMU-UHFFFAOYSA-N 0.000 claims description 4
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 4
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims description 4
- 241001112258 Moca Species 0.000 claims description 4
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 4
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 4
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 claims description 4
- 239000000600 sorbitol Substances 0.000 claims description 4
- 230000002194 synthesizing effect Effects 0.000 claims description 4
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 claims description 4
- 230000009471 action Effects 0.000 claims description 2
- 229920001400 block copolymer Polymers 0.000 claims description 2
- 238000004132 cross linking Methods 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- DTCPBBPYYOBKGN-UHFFFAOYSA-N N,N-dihydroxy-2,3-di(propan-2-yl)aniline Chemical compound ON(C1=C(C(=CC=C1)C(C)C)C(C)C)O DTCPBBPYYOBKGN-UHFFFAOYSA-N 0.000 claims 2
- 239000011162 core material Substances 0.000 abstract description 20
- 239000002245 particle Substances 0.000 abstract description 10
- 239000000049 pigment Substances 0.000 abstract description 7
- 230000000694 effects Effects 0.000 abstract description 5
- 239000003054 catalyst Substances 0.000 abstract description 3
- 238000002834 transmittance Methods 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 8
- 229920001577 copolymer Polymers 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000004408 titanium dioxide Substances 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 230000018044 dehydration Effects 0.000 description 3
- 238000006297 dehydration reaction Methods 0.000 description 3
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 230000036541 health Effects 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 229920002396 Polyurea Polymers 0.000 description 2
- 229920001807 Urea-formaldehyde Polymers 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000002612 dispersion medium Substances 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- 238000001962 electrophoresis Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- OVSARSKQWCLSJT-UHFFFAOYSA-N n,n-di(propan-2-yl)aniline Chemical compound CC(C)N(C(C)C)C1=CC=CC=C1 OVSARSKQWCLSJT-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- BGHCVCJVXZWKCC-UHFFFAOYSA-N tetradecane Chemical compound CCCCCCCCCCCCCC BGHCVCJVXZWKCC-UHFFFAOYSA-N 0.000 description 2
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 102000002322 Egg Proteins Human genes 0.000 description 1
- 108010000912 Egg Proteins Proteins 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- YCUVUDODLRLVIC-UHFFFAOYSA-N Sudan black B Chemical class C1=CC(=C23)NC(C)(C)NC2=CC=CC3=C1N=NC(C1=CC=CC=C11)=CC=C1N=NC1=CC=CC=C1 YCUVUDODLRLVIC-UHFFFAOYSA-N 0.000 description 1
- BWKZWWVOAKQPIO-UHFFFAOYSA-M [Cl-].C(CC)[N+](OC)(OC)OC Chemical compound [Cl-].C(CC)[N+](OC)(OC)OC BWKZWWVOAKQPIO-UHFFFAOYSA-M 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N anhydrous trimethylamine Natural products CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- 239000001000 anthraquinone dye Substances 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
- 239000001045 blue dye Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- JBTHDAVBDKKSRW-UHFFFAOYSA-N chembl1552233 Chemical compound CC1=CC(C)=CC=C1N=NC1=C(O)C=CC2=CC=CC=C12 JBTHDAVBDKKSRW-UHFFFAOYSA-N 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 1
- HSTNMAHVBABHLU-UHFFFAOYSA-M dodecyl-dimethyl-propylazanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)CCC HSTNMAHVBABHLU-UHFFFAOYSA-M 0.000 description 1
- 210000003278 egg shell Anatomy 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 229940107698 malachite green Drugs 0.000 description 1
- FDZZZRQASAIRJF-UHFFFAOYSA-M malachite green Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1C(C=1C=CC=CC=1)=C1C=CC(=[N+](C)C)C=C1 FDZZZRQASAIRJF-UHFFFAOYSA-M 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- 150000004028 organic sulfates Chemical class 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- 238000005453 pelletization Methods 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- ZJMWRROPUADPEA-UHFFFAOYSA-N sec-butylbenzene Chemical compound CCC(C)C1=CC=CC=C1 ZJMWRROPUADPEA-UHFFFAOYSA-N 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 229940073450 sudan red Drugs 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
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
- B01J13/16—Interfacial polymerisation
-
- 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
- B01J13/025—Applications of microcapsules not provided for in other subclasses
-
- 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
- B01J13/20—After-treatment of capsule walls, e.g. hardening
- B01J13/206—Hardening; drying
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3225—Polyamines
- C08G18/3228—Polyamines acyclic
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/61—Polysiloxanes
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/6505—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen the low-molecular compounds being compounds of group C08G18/32 or polyamines of C08G18/38
- C08G18/6523—Compounds of group C08G18/3225 or C08G18/3271 or polyamines of C08G18/38
- C08G18/6529—Compounds of group C08G18/3225 or polyamines of C08G18/38
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/50—Sympathetic, colour changing or similar inks
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/165—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on translational movement of particles in a fluid under the influence of an applied field
- G02F1/1675—Constructional details
- G02F1/16757—Microcapsules
-
- G—PHYSICS
- G09—EDUCATION; CRYPTOGRAPHY; DISPLAY; ADVERTISING; SEALS
- G09F—DISPLAYING; ADVERTISING; SIGNS; LABELS OR NAME-PLATES; SEALS
- G09F9/00—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements
- G09F9/30—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements in which the desired character or characters are formed by combining individual elements
- G09F9/301—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements in which the desired character or characters are formed by combining individual elements flexible foldable or roll-able electronic displays, e.g. thin LCD, OLED
Abstract
The invention relates to an electronic ink microcapsule, electronic ink and a preparation method thereof. The formaldehyde-free photosensitive microcapsule consists of a capsule wall and a capsule core, wherein the capsule wall material is a wall material, and polysiloxane modified polyurea-polyurethane copolymer is used. The capsule core material is a core material and comprises modified pigment particles. The invention also provides a preparation method of the electronic ink microcapsule, which is simple and easy to operate, does not need to add a catalyst in the preparation process, has good light transmittance, good color development effect and excellent mechanical properties, can ensure the integrity of the microcapsule body under the impact of external force, has good thermal stability, does not deform, adhere and leak in a high-temperature environment, and still has good display performance after long-time ultraviolet irradiation and use.
Description
Technical Field
The invention belongs to the technical field of electronic ink, and particularly relates to an electronic ink microcapsule, electronic ink, a preparation method and a flexible display screen.
Background
The microcapsule is a micro-container with polymer or inorganic wall, and through microcapsule pelletizing technology, solid, liquid or gas may be embedded and sealed into one solid microcapsule. In 1997, the institute of technology (MIT) media laboratory proposed the concept of microencapsulated electronic ink (Encapsulated electrophoretic ink), i.e., microencapsulated electrophoretic display technology (Encapsulated electrophoretic display). On the basis of electrophoretic display, the method creatively microencapsulates the electrophoresis base liquid, not only inhibits the defects of agglomeration, deposition and the like of electrophoresis colloidal particles in a range larger than the capsule scale, but also realizes electrophoretic display in the microcapsule, improves the stability and prolongs the service life. Because the electronic ink microcapsule is used in electronic equipment, the mechanical strength and the temperature resistance are particularly important, melamine-formaldehyde resin and urea resin are generally selected to be used as wall materials when the microcapsule is prepared, and the low-cost resin can provide excellent mechanical properties to protect the microcapsule from being broken and invalid due to external factors, but can generate a large amount of aldehyde substances to endanger health, and can be quickly aged and decomposed in a high-temperature environment to lose the original effect, once the wall materials are damaged and broken, the display particle materials can be quickly lost, and the electronic ink display device is disabled.
Chinese patent CN201910991846.9 discloses a method for preparing microcapsule electronic ink, the first layer of the invention uses polyurea resin as wall material, titanium dioxide as core material, spray drying method is adopted to coat the polyurea resin on the titanium dioxide, the second layer uses urea-formaldehyde as raw material, in situ polymerization method is adopted to prepare double-layer microcapsule, which increases the thickness of microcapsule wall, improves the toughness and strength of microcapsule wall, the double-layer capsule has double-layer structure similar to eggshell, improves the scratch resistance and pressure resistance of microcapsule, but the process is complex, the microcapsule transparency is relatively low, in addition, formaldehyde is used as capsule wall material, the high temperature is easy to decompose, and the production and use process are not friendly to environment.
Disclosure of Invention
Aiming at the defects of the prior art, the invention provides the electronic ink microcapsule, the electronic ink and the preparation method, which are formaldehyde-free and environment-friendly, and can provide excellent mechanical property and heat resistance under the precondition that microcapsule cores fully play a role, ensure that microcapsule materials of the electronic ink microcapsule cannot flow out and be lost due to breakage of microcapsule wall materials in the use process, and greatly improve the heat resistance of the microcapsule so as to resist the high-temperature extreme environment in the outside and electronic equipment.
In order to achieve the above purpose, the technical scheme adopted by the invention is as follows:
the first aspect of the invention provides an electronic ink microcapsule, which consists of a wall material and a capsule core, wherein the wall material comprises a polysiloxane modified polyurea-polyurethane copolymer, the polysiloxane modified polyurea-polyurethane copolymer is formed by synthesizing a wall material prepolymer from an isocyanate-terminated polyurethane prepolymer and a hydroxyl-terminated polysiloxane, and then crosslinking and curing the wall material prepolymer under the action of an alcohol chain extender and an amine chain extender.
Preferably, the capsule core comprises a dispersing agent, an organic solvent, a surfactant and display particles which are coated in the wall material.
Preferably, the average molecular weight of the isocyanate-terminated polyurethane prepolymer is 2500 to 10000, and the average polymerization degree of the hydroxyl-terminated polysiloxane is 5 to 10; the molar ratio of the two is about 2:1.
Preferably, the alcohol chain extender is one or more of 1, 4-Butanediol (BDO), 1, 6-hexanediol, ethylene glycol, glycerol, trimethylolpropane, diethylene glycol (DEG), triethylene glycol, neopentyl glycol (NPG), sorbitol, diethylaminoethanol (DEAE), and the amine chain extender is one or more of MOCA, ethylenediamine (DA), diethylenetriamine (DETA), tetraethylenepentamine (TEPA), N-dihydroxy (diisopropyl) aniline (HPA).
Preferably, the weight ratio of the wall material to the capsule core is 1:0.5 to 1:2.
the second aspect of the invention provides electronic ink comprising the electronic ink microcapsule.
In a third aspect, the present invention provides a flexible display screen, including an electronic ink layer, where the electronic ink layer includes the electronic ink.
The fourth aspect of the invention provides a method for preparing an electronic ink microcapsule, which comprises the following steps:
1) Synthesizing a wall material prepolymer by using isocyanate-terminated polyurethane prepolymer and hydroxyl-terminated polysiloxane:
2) Preparing a capsule core solution, adding the wall material prepolymer obtained in the step 1), and uniformly mixing to obtain an oil phase solution;
3) Adding the oil phase solution obtained in the step 2) into an aqueous solution of a styrene-maleic anhydride block copolymer, and stirring at a high speed to form an oil-in-water O/W emulsion;
4) Adding an alcohol chain extender and an amine chain extender into the emulsion, heating and maintaining stirring to form a polysiloxane modified polyurea-polyurethane copolymer wall material on the interface of emulsion liquid drops;
5) And then heating up for reaction, filtering, washing and drying after the reaction is finished to obtain microcapsule powder.
Preferably, the reaction temperature in step 1) is 90 ℃.
Preferably, the temperature is raised to 50-60 ℃ in step 4).
Preferably, in step 5), the temperature is raised to 90-95 ℃ and the reaction is carried out for 3-5 hours.
Preferably, the core solution comprises a dispersant, an organic solvent, a surfactant, and display particles.
Preferably, the alcohol chain extender is one or more of 1, 4-Butanediol (BDO), 1, 6-hexanediol, ethylene glycol, glycerol, trimethylolpropane, diethylene glycol (DEG), triethylene glycol, neopentyl glycol (NPG), sorbitol, diethylaminoethanol (DEAE), and the amine chain extender is one or more of MOCA, ethylenediamine (DA), diethylenetriamine (DETA), tetraethylenepentamine (TEPA), N-dihydroxy (diisopropyl) aniline (HPA).
Compared with the prior art, the invention has the following outstanding effects:
the invention solves the problems that the existing electronic ink microcapsule can generate a large amount of aldehydes to harm health, and can be rapidly aged and decomposed in a high-temperature environment so as to lose the original effect. According to the preparation method of the electronic ink microcapsule, a catalyst is not required to be added, the prepared ink microcapsule has the advantages of quick and simple preparation, good thermal stability, no deformation and no stretching in a high-temperature environment of 200 ℃, and no aldehyde substance harmful to health; the capsule has good mechanical properties, can keep the integrity and elasticity of the capsule body under the impact of external force to protect the capsule core material and is isolated from the external environment, and the capsule core material can not run off even if the capsule wall is damaged under the influence of the great external force; meanwhile, the capsule wall is thin, and has good light transmission performance, so that the color of the capsule core is effectively displayed. The electronic ink prepared by the electronic ink microcapsule has high stability, and has good and clear display effect when applied to a flexible display screen.
Drawings
Fig. 1 is a Scanning Electron Microscope (SEM) image of the electronic ink microcapsule prepared in example 1.
Fig. 2 is a Scanning Electron Microscope (SEM) image of the electronic ink microcapsule prepared in the comparative example.
Detailed Description
The current preparation method of the electronic ink microcapsule basically comprises the process steps of pigment particle surface modification treatment, capsule core solution preparation, electronic ink microcapsule preparation and the like. In the preparation of the electronic ink microcapsule, the pigment particles used may be organic or inorganic pigments such as titanium dioxide, zinc oxide, zirconium oxide, black pigments such as carbon black, nigrosine, etc. In actual use, the colorant may impart a target color to the yin-yang particles, and the colored pigments include red, blue, brown, green, and the like. In the following embodiments, white pigments such as titanium dioxide or other colors such as red, yellow, blue, green, etc. are used.
In the preparation process of the capsule core solution, polyoxyethylene lauric acid is used as a charge control agent, and modified pigment particles are dispersed in a solution compounded by sec-butylbenzene dyed with blue dye or not dyed with dye and tetrachloroethylene to form a charged and stable capsule core solution.
Dispersing the prepared electronic ink microcapsule in a dispersion medium to obtain the electronic ink, wherein the dispersion medium comprises but is not limited to: halogenated organic solvents, tetrafluoro-dibromo-ethylene, tetrachloroethylene, 1,2, 4-trichlorobenzene, carbon tetrachloride. The low density material is one or more of hydrocarbons, dodecane, tetradecane, aliphatic hydrocarbon series, silanes, decane-based siloxane, polyphenol-based siloxane, heptyl-based siloxane, etc. Dyes may be added to the electronic ink to reduce light reflection and improve display contrast. The common dyes include azo dyes, oil-soluble red, sudan red and sudan black series, anthraquinone dyes 361, oil-soluble Blue, macrolex Blue series, triarylmethane, malachite green, crystal violet, etc. Charge inhibitors and stabilizers may also be added to the electronic ink to improve display particle electrophoretic properties and space temperature properties. The charge control agent may be an organic sulfate or sulfonate, a metal soap, an organic amide, an organic phosphate or phosphate, or a polymer or graft copolymer and monomers thereof. The stabilizer comprises nonionic trimethylamine ethyl lactone, phospholipid, lecithin, polyoxyethylene, olefin oxide, alkyl dimethylamine oxide, sodium dodecyl benzene sulfonate, sodium dodecyl sulfate, dodecyl dimethyl propyl ammonium chloride, propyl trimethoxy chloride, trimethoxy propyl ammonium chloride and the like.
The present invention will be described in detail with reference to specific examples. The following examples will assist those skilled in the art in further understanding the present invention, but are not intended to limit the invention in any way. It should be noted that variations and modifications could be made by those skilled in the art without departing from the inventive concept. These are all within the scope of the present invention.
Example 1
After the isocyanate-terminated polyurethane prepolymer with the average large molecular weight of 5000 is completely dehydrated, 100g of the isocyanate-terminated polyurethane prepolymer is weighed and put into a three-neck flask, the temperature is raised to 90 ℃ under the protection of nitrogen, slow stirring is maintained, meanwhile, 3.1g of hydroxyl-terminated polysiloxane with the average polymerization degree of 5 is weighed and slowly added dropwise after the complete dehydration, and the wall material prepolymer is obtained after the reaction for 6 hours.
And after the wall material prepolymer is cooled to room temperature, 60g of the capsule core solution and 30g of the wall material prepolymer are weighed and fully and uniformly stirred.
Adding the oil phase solution into an aqueous solution of a styrene-maleic anhydride segmented copolymer, stirring at a high speed to form an oil-in-water O/W emulsion, slowly dripping 15g of diethylenetriamine into the emulsion, heating to 60 ℃ and maintaining stirring, forming a polysiloxane modified polyurea-polyurethane copolymer wall material on the interface of emulsion liquid drops, heating to 95 ℃ for reacting for 3 hours, filtering and washing microcapsule powder after the reaction is completed, and heating and drying for 24 hours at 60 ℃ to obtain the electronic ink microcapsule.
As shown in fig. 1, a Scanning Electron Microscope (SEM) determines that the appearance of the prepared electronic ink microcapsule is in a complete microcapsule monodisperse state.
Example 2
After the isocyanate-terminated polyurethane prepolymer with the average large molecular weight of 10000 is completely dehydrated, 200g of the isocyanate-terminated polyurethane prepolymer is weighed and put into a three-neck flask, the temperature is raised to 90 ℃ under the protection of nitrogen, slow stirring is maintained, meanwhile, 5.3g of hydroxyl-terminated polysiloxane with the average polymerization degree of 10 is weighed and slowly added dropwise after the complete dehydration, and the reaction is carried out for 8 hours, thus obtaining the wall material prepolymer.
And after the wall material prepolymer is cooled to room temperature, weighing 15g of the capsule core solution and 30g of the wall material prepolymer, and fully and uniformly stirring.
Adding the oil phase solution into an aqueous solution of a styrene-maleic anhydride segmented copolymer, stirring at a high speed to form an oil-in-water O/W emulsion, slowly dripping 8g of ethylenediamine into the emulsion, heating to 50 ℃ and maintaining stirring, forming a polysiloxane modified polyurea-polyurethane copolymer wall material on the interface of emulsion liquid drops, heating to 95 ℃ for reacting for 5 hours, filtering and washing microcapsule powder after the reaction is completed, and heating and drying for 18 hours at 80 ℃ to obtain the electronic ink microcapsule.
Example 3
After the isocyanate-terminated polyurethane prepolymer with the average large molecular weight of 2500 is completely dehydrated, 80g of the isocyanate-terminated polyurethane prepolymer is weighed and put into a three-neck flask, the temperature is raised to 90 ℃ under the protection of nitrogen, slow stirring is maintained, meanwhile, after the hydroxyl-terminated polysiloxane with the average polymerization degree of 10 is completely dehydrated, 2.2g of the isocyanate-terminated polyurethane prepolymer is weighed and slowly added dropwise, and the reaction is carried out for 5 hours, thus obtaining the wall material prepolymer.
After the wall material prepolymer is cooled to room temperature, 30g of the capsule core solution and 30g of the wall material prepolymer are weighed and fully and uniformly stirred.
Adding the oil phase solution into an aqueous solution of a styrene-maleic anhydride segmented copolymer, stirring at a high speed to form an oil-in-water O/W emulsion, slowly dripping 12g of ethylenediamine into the emulsion, heating to 50 ℃ and maintaining stirring, forming a polysiloxane modified polyurea-polyurethane copolymer wall material on the interface of emulsion liquid drops, heating to 90 ℃ for reacting for 5 hours, filtering and washing microcapsule powder after the reaction is completed, and heating and drying for 24 hours at 60 ℃ to obtain the electronic ink microcapsule.
Comparative example 1
After the isocyanate-terminated polyurethane prepolymer with the average large molecular weight of 5000 is completely dehydrated, 100g of the isocyanate-terminated polyurethane prepolymer is weighed and put into a three-neck flask, the temperature is raised to 90 ℃ under the protection of nitrogen, slow stirring is maintained, meanwhile, 3.1g of hydroxyl-terminated polysiloxane with the average polymerization degree of 5 is weighed and slowly added dropwise after the complete dehydration, and the reaction is carried out for 5 hours, thus obtaining the wall material prepolymer.
And after the wall material prepolymer is cooled to room temperature, 60g of the capsule core solution and 30g of the wall material prepolymer are weighed and fully and uniformly stirred.
Adding the oil phase solution into an aqueous solution of a styrene-maleic anhydride segmented copolymer, stirring at a high speed to form an oil-in-water O/W emulsion, slowly dripping 15g of diethylenetriamine and 0.2g of organic bismuth into the emulsion, heating to 60 ℃ and maintaining stirring, forming a polysiloxane modified polyurea-polyurethane copolymer wall material on an emulsion droplet interface, heating to 95 ℃ for reacting for 3 hours, filtering and washing microcapsule powder after the reaction is completed, and heating and drying for 24 hours at 60 ℃ to obtain the electronic ink microcapsule.
As shown in fig. 2, a Scanning Electron Microscope (SEM) determines that the appearance of the prepared electronic ink microcapsule is in a complete microcapsule monodisperse state. Compared with the electronic ink microcapsule prepared in the example 1, the electronic ink microcapsule prepared by adding the catalyst has higher integrity.
Claims (9)
1. An electronic ink microcapsule comprises a wall material and a capsule core, wherein the capsule core is coated in the wall material, and the electronic ink microcapsule is characterized in that: the wall material comprises a polysiloxane modified polyurea-polyurethane copolymer, wherein the polysiloxane modified polyurea-polyurethane copolymer is formed by synthesizing a wall material prepolymer from an isocyanate-terminated polyurethane prepolymer and hydroxyl-terminated polysiloxane, and then crosslinking and solidifying the wall material prepolymer under the action of an alcohol chain extender and an amine chain extender; the average macromolecular weight of the isocyanate-terminated polyurethane prepolymer is 2500 to 10000, the average polymerization degree of the hydroxyl-terminated polysiloxane is 5 to 10, and the molar ratio of the hydroxyl-terminated polysiloxane to the hydroxyl-terminated polysiloxane is 2:1.
2. The electronic ink microcapsule of claim 1, wherein: the alcohol chain extender is one or more of 1, 4-Butanediol (BDO), 1, 6-hexanediol, ethylene glycol, glycerol, trimethylolpropane, diethylene glycol (DEG), triethylene glycol, neopentyl glycol (NPG), sorbitol and Diethylaminoethanol (DEAE); the amine chain extender is one or more of MOCA, ethylenediamine (DA), diethylenetriamine (DETA), tetraethylenepentamine (TEPA) and N, N-dihydroxyl (diisopropyl) aniline (HPA).
3. The electronic ink microcapsule of claim 1, wherein: the weight ratio of the wall material to the capsule core is 1:0.5 to 1:2.
4. an electronic ink, characterized in that: an electronic ink microcapsule comprising any of claims 1-3.
5. A flexible display screen comprising an electronic ink layer, characterized in that: an electronic ink as defined in claim 4 is provided in the electronic ink layer.
6. A method for preparing the electronic ink microcapsule of claim 1, comprising the steps of:
1) Synthesizing a wall material prepolymer by using isocyanate-terminated polyurethane prepolymer and hydroxyl-terminated polysiloxane;
2) Preparing a capsule core solution, adding the wall material prepolymer obtained in the step 1), and uniformly mixing to obtain an oil phase solution;
3) Adding the oil phase solution obtained in the step 2) into an aqueous solution of a styrene-maleic anhydride block copolymer, and stirring at a high speed to form an oil-in-water O/W emulsion;
4) Adding an alcohol chain extender and an amine chain extender into the emulsion, heating and maintaining stirring to form a polysiloxane modified polyurea-polyurethane copolymer wall material on the interface of emulsion liquid drops;
5) And then heating up for reaction, filtering, washing and drying after the reaction is finished to obtain microcapsule powder.
7. The method for preparing the electronic ink microcapsule according to claim 6, wherein: and in the step 4), the temperature is increased to 50-60 ℃.
8. The method for preparing the electronic ink microcapsule according to claim 6, wherein: the temperature is raised to 90-95 ℃ in the step 5) to react for 3-5 hours.
9. The method for preparing the electronic ink microcapsule according to claim 6, wherein: the alcohol chain extender is one or more of 1, 4-Butanediol (BDO), 1, 6-hexanediol, ethylene glycol, glycerol, trimethylolpropane, diethylene glycol (DEG), triethylene glycol, neopentyl glycol (NPG), sorbitol and Diethylaminoethanol (DEAE), and the amine chain extender is one or more of MOCA, ethylenediamine (DA), diethylenetriamine (DETA), tetraethylenepentamine (TEPA) and N, N-dihydroxyl (diisopropyl) aniline (HPA).
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| JP2009203592A (en) * | 2008-02-29 | 2009-09-10 | Seikoh Chem Co Ltd | Coating material for fabric |
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| CN101027335A (en) * | 2004-07-26 | 2007-08-29 | 巴斯福股份公司 | Cross-linked polytetrahydrofuran-containing polyurethanes |
| JP2008209736A (en) * | 2007-02-27 | 2008-09-11 | Sumika Bayer Urethane Kk | Polyurethane elastomer for cleaning blade of electrophotographic copying machine |
| JP2009203592A (en) * | 2008-02-29 | 2009-09-10 | Seikoh Chem Co Ltd | Coating material for fabric |
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