TWI447137B - 官能化的粒子 - Google Patents
官能化的粒子 Download PDFInfo
- Publication number
- TWI447137B TWI447137B TW094126123A TW94126123A TWI447137B TW I447137 B TWI447137 B TW I447137B TW 094126123 A TW094126123 A TW 094126123A TW 94126123 A TW94126123 A TW 94126123A TW I447137 B TWI447137 B TW I447137B
- Authority
- TW
- Taiwan
- Prior art keywords
- group
- fiber
- polyisocyanate
- alkyl
- sulfo
- Prior art date
Links
- 239000002245 particle Substances 0.000 title claims description 44
- -1 ethoxylated Chemical group 0.000 claims description 95
- 239000005056 polyisocyanate Substances 0.000 claims description 55
- 229920001228 polyisocyanate Polymers 0.000 claims description 55
- 150000001875 compounds Chemical class 0.000 claims description 45
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 35
- 125000005442 diisocyanate group Chemical group 0.000 claims description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims description 28
- 239000002243 precursor Substances 0.000 claims description 28
- 239000001257 hydrogen Substances 0.000 claims description 27
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 27
- 239000000835 fiber Substances 0.000 claims description 24
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 24
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 23
- 150000002367 halogens Chemical class 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 20
- 229920000768 polyamine Polymers 0.000 claims description 20
- 229920005862 polyol Polymers 0.000 claims description 20
- 238000002360 preparation method Methods 0.000 claims description 20
- 229910052736 halogen Inorganic materials 0.000 claims description 19
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 239000000460 chlorine Substances 0.000 claims description 16
- 229910052801 chlorine Inorganic materials 0.000 claims description 16
- 239000011159 matrix material Substances 0.000 claims description 16
- 150000003077 polyols Chemical class 0.000 claims description 16
- 239000002657 fibrous material Substances 0.000 claims description 15
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 15
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 15
- 239000012071 phase Substances 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 239000000126 substance Substances 0.000 claims description 13
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 13
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 12
- 150000001412 amines Chemical class 0.000 claims description 12
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 12
- 229910052794 bromium Inorganic materials 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 230000002209 hydrophobic effect Effects 0.000 claims description 10
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 10
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 9
- 239000008346 aqueous phase Substances 0.000 claims description 9
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- 239000011737 fluorine Substances 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 239000006185 dispersion Substances 0.000 claims description 8
- 229920000742 Cotton Polymers 0.000 claims description 7
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 6
- 125000005184 naphthylamino group Chemical group C1(=CC=CC2=CC=CC=C12)N* 0.000 claims description 6
- 229920002554 vinyl polymer Polymers 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 238000012643 polycondensation polymerization Methods 0.000 claims description 5
- 239000004814 polyurethane Substances 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 4
- 229920002396 Polyurea Polymers 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- WHIVNJATOVLWBW-PLNGDYQASA-N (nz)-n-butan-2-ylidenehydroxylamine Chemical compound CC\C(C)=N/O WHIVNJATOVLWBW-PLNGDYQASA-N 0.000 claims description 3
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 3
- 238000012644 addition polymerization Methods 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 229920003226 polyurethane urea Polymers 0.000 claims description 2
- DFJCYPRWCUFLBQ-UHFFFAOYSA-N NCCCC(C(OCC)(OCC)OCC)CCCCCCC Chemical compound NCCCC(C(OCC)(OCC)OCC)CCCCCCC DFJCYPRWCUFLBQ-UHFFFAOYSA-N 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 239000002759 woven fabric Substances 0.000 claims 1
- 239000000243 solution Substances 0.000 description 48
- 239000011859 microparticle Substances 0.000 description 33
- 239000000203 mixture Substances 0.000 description 33
- 239000004744 fabric Substances 0.000 description 26
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 21
- 239000012948 isocyanate Substances 0.000 description 18
- 239000008367 deionised water Substances 0.000 description 15
- 229910021641 deionized water Inorganic materials 0.000 description 15
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 14
- 238000003756 stirring Methods 0.000 description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 239000007864 aqueous solution Substances 0.000 description 11
- 239000000758 substrate Substances 0.000 description 10
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 9
- 125000003118 aryl group Chemical group 0.000 description 9
- 150000002431 hydrogen Chemical group 0.000 description 9
- 125000003277 amino group Chemical group 0.000 description 8
- 150000002009 diols Chemical class 0.000 description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 125000004093 cyano group Chemical group *C#N 0.000 description 7
- 239000010419 fine particle Substances 0.000 description 7
- 150000002513 isocyanates Chemical class 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 239000003094 microcapsule Substances 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 235000019198 oils Nutrition 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 239000004094 surface-active agent Substances 0.000 description 7
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 6
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- JJLKTTCRRLHVGL-UHFFFAOYSA-L [acetyloxy(dibutyl)stannyl] acetate Chemical compound CC([O-])=O.CC([O-])=O.CCCC[Sn+2]CCCC JJLKTTCRRLHVGL-UHFFFAOYSA-L 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 6
- 125000002947 alkylene group Chemical group 0.000 description 6
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 6
- 229920002678 cellulose Polymers 0.000 description 6
- 235000010980 cellulose Nutrition 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 238000005538 encapsulation Methods 0.000 description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 5
- 230000000845 anti-microbial effect Effects 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 239000001913 cellulose Substances 0.000 description 5
- 125000001309 chloro group Chemical group Cl* 0.000 description 5
- 239000011162 core material Substances 0.000 description 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 239000000985 reactive dye Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 239000005058 Isophorone diisocyanate Substances 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 239000004721 Polyphenylene oxide Substances 0.000 description 4
- 230000032683 aging Effects 0.000 description 4
- 125000002723 alicyclic group Chemical group 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 238000004043 dyeing Methods 0.000 description 4
- 239000000796 flavoring agent Substances 0.000 description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 229920000570 polyether Polymers 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- OHLKMGYGBHFODF-UHFFFAOYSA-N 1,4-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=C(CN=C=O)C=C1 OHLKMGYGBHFODF-UHFFFAOYSA-N 0.000 description 3
- SXPGQGNWEWPWQZ-UHFFFAOYSA-N 4-(triethoxymethyl)dodecan-1-amine Chemical compound NCCCC(C(OCC)(OCC)OCC)CCCCCCCC SXPGQGNWEWPWQZ-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- 102000011782 Keratins Human genes 0.000 description 3
- 108010076876 Keratins Proteins 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- 239000004952 Polyamide Substances 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- XEFQLINVKFYRCS-UHFFFAOYSA-N Triclosan Chemical compound OC1=CC(Cl)=CC=C1OC1=CC=C(Cl)C=C1Cl XEFQLINVKFYRCS-UHFFFAOYSA-N 0.000 description 3
- 239000012963 UV stabilizer Substances 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- FBSAITBEAPNWJG-UHFFFAOYSA-N dimethyl phthalate Natural products CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 description 3
- 229960001826 dimethylphthalate Drugs 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 3
- 125000005456 glyceride group Chemical group 0.000 description 3
- 210000004209 hair Anatomy 0.000 description 3
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 3
- 150000002596 lactones Chemical class 0.000 description 3
- 230000014759 maintenance of location Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 3
- 150000002790 naphthalenes Chemical class 0.000 description 3
- 239000002736 nonionic surfactant Substances 0.000 description 3
- 230000000269 nucleophilic effect Effects 0.000 description 3
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- 229910021653 sulphate ion Inorganic materials 0.000 description 3
- 239000002562 thickening agent Substances 0.000 description 3
- 125000003396 thiol group Chemical class [H]S* 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- 229960003500 triclosan Drugs 0.000 description 3
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 3
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 description 2
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 2
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 2
- PMBXCGGQNSVESQ-UHFFFAOYSA-N 1-Hexanethiol Chemical compound CCCCCCS PMBXCGGQNSVESQ-UHFFFAOYSA-N 0.000 description 2
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- ULQISTXYYBZJSJ-UHFFFAOYSA-N 12-hydroxyoctadecanoic acid Chemical compound CCCCCCC(O)CCCCCCCCCCC(O)=O ULQISTXYYBZJSJ-UHFFFAOYSA-N 0.000 description 2
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidine Chemical compound CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 2
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- SXFJDZNJHVPHPH-UHFFFAOYSA-N 3-methylpentane-1,5-diol Chemical compound OCCC(C)CCO SXFJDZNJHVPHPH-UHFFFAOYSA-N 0.000 description 2
- GRFNBEZIAWKNCO-UHFFFAOYSA-N 3-pyridinol Chemical compound OC1=CC=CN=C1 GRFNBEZIAWKNCO-UHFFFAOYSA-N 0.000 description 2
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- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
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- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
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- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- 238000012695 Interfacial polymerization Methods 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
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- SJWFXCIHNDVPSH-UHFFFAOYSA-N octan-2-ol Chemical compound CCCCCCC(C)O SJWFXCIHNDVPSH-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- ZKRNQSNKDPEUOH-UHFFFAOYSA-N octane-1,5-diol Chemical compound CCCC(O)CCCCO ZKRNQSNKDPEUOH-UHFFFAOYSA-N 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- QUBQYFYWUJJAAK-UHFFFAOYSA-N oxymethurea Chemical compound OCNC(=O)NCO QUBQYFYWUJJAAK-UHFFFAOYSA-N 0.000 description 1
- 229950005308 oxymethurea Drugs 0.000 description 1
- 229960005489 paracetamol Drugs 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 239000003016 pheromone Substances 0.000 description 1
- PJGSXYOJTGTZAV-UHFFFAOYSA-N pinacolone Chemical compound CC(=O)C(C)(C)C PJGSXYOJTGTZAV-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000083 poly(allylamine) Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 description 1
- 150000004804 polysaccharides Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000000899 pressurised-fluid extraction Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 1
- SHNUBALDGXWUJI-UHFFFAOYSA-N pyridin-2-ylmethanol Chemical compound OCC1=CC=CC=N1 SHNUBALDGXWUJI-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 1
- 150000004060 quinone imines Chemical class 0.000 description 1
- DCBSHORRWZKAKO-UHFFFAOYSA-N rac-1-monomyristoylglycerol Chemical compound CCCCCCCCCCCCCC(=O)OCC(O)CO DCBSHORRWZKAKO-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- RNVYQYLELCKWAN-UHFFFAOYSA-N solketal Chemical compound CC1(C)OCC(CO)O1 RNVYQYLELCKWAN-UHFFFAOYSA-N 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 229940031439 squalene Drugs 0.000 description 1
- TUHBEKDERLKLEC-UHFFFAOYSA-N squalene Natural products CC(=CCCC(=CCCC(=CCCC=C(/C)CCC=C(/C)CC=C(C)C)C)C)C TUHBEKDERLKLEC-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 239000000979 synthetic dye Substances 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- DIHAURBCYGTGCV-UHFFFAOYSA-N xi-4,5-Dihydro-2,4(5)-dimethyl-1H-imidazole Chemical compound CC1CN=C(C)N1 DIHAURBCYGTGCV-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/80—Masked polyisocyanates
- C08G18/8061—Masked polyisocyanates masked with compounds having only one group containing active hydrogen
- C08G18/8064—Masked polyisocyanates masked with compounds having only one group containing active hydrogen with monohydroxy compounds
-
- 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
- B01J13/20—After-treatment of capsule walls, e.g. hardening
-
- 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
- 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
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/80—Masked polyisocyanates
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/564—Polyureas, polyurethanes or other polymers having ureide or urethane links; Precondensation products forming them
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Dispersion Chemistry (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Polyurethanes Or Polyureas (AREA)
- Manufacturing Of Micro-Capsules (AREA)
- Chemical Or Physical Treatment Of Fibers (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP04103755 | 2004-08-04 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW200613352A TW200613352A (en) | 2006-05-01 |
| TWI447137B true TWI447137B (zh) | 2014-08-01 |
Family
ID=34929421
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW094126123A TWI447137B (zh) | 2004-08-04 | 2005-08-02 | 官能化的粒子 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US8546509B2 (https=) |
| EP (1) | EP1773484B1 (https=) |
| JP (2) | JP5419353B2 (https=) |
| KR (1) | KR101219118B1 (https=) |
| CN (1) | CN100577278C (https=) |
| BR (1) | BRPI0514050B1 (https=) |
| MX (1) | MX2007001369A (https=) |
| TW (1) | TWI447137B (https=) |
| WO (1) | WO2006013165A1 (https=) |
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT103265B (pt) | 2005-04-22 | 2007-02-28 | Univ Do Minho | Microcápsulas com grupos funcionais reactivos de ligação a fibras têxteis e processo de aplicação e fixação |
| US9234059B2 (en) | 2008-07-16 | 2016-01-12 | Outlast Technologies, LLC | Articles containing functional polymeric phase change materials and methods of manufacturing the same |
| US8404341B2 (en) | 2006-01-26 | 2013-03-26 | Outlast Technologies, LLC | Microcapsules and other containment structures for articles incorporating functional polymeric phase change materials |
| FR2897617B1 (fr) | 2006-02-20 | 2008-05-16 | Centre Nat Rech Scient | Capsules a surface modifiee pour greffage sur des fibres |
| US8680212B2 (en) | 2006-03-24 | 2014-03-25 | L'oreal | Composite dyestuff of microcapsule type and cosmetic use thereof |
| FR2898904B1 (fr) * | 2006-03-24 | 2012-12-14 | Oreal | Materiau colorant composite de type microcapsules et son utilisation cosmetique |
| WO2007110383A1 (de) * | 2006-03-28 | 2007-10-04 | Basf Se | Verkapselung lipophiler wirkstoffe |
| PT103576B (pt) * | 2006-10-03 | 2008-12-30 | Univ Do Minho | Aglomerados de microcápsulas de materiais de mudança de fase (pcm), processos para a sua obtenção e sua aplicação em materiais poliméricos fibrosos ou porosos |
| GB0623110D0 (en) | 2006-11-21 | 2006-12-27 | Ciba Sc Holding Ag | Microcapules, their use and processes for their manufacture |
| US8221910B2 (en) | 2008-07-16 | 2012-07-17 | Outlast Technologies, LLC | Thermal regulating building materials and other construction components containing polymeric phase change materials |
| US9816059B2 (en) * | 2009-09-18 | 2017-11-14 | International Flavors & Fragrances | Stabilized capsule compositions |
| US9687424B2 (en) | 2009-09-18 | 2017-06-27 | International Flavors & Fragrances | Polyurea capsules prepared with aliphatic isocyanates and amines |
| US10085925B2 (en) | 2009-09-18 | 2018-10-02 | International Flavors & Fragrances Inc. | Polyurea capsule compositions |
| US11311467B2 (en) | 2009-09-18 | 2022-04-26 | International Flavors & Fragrances Inc. | Polyurea capsules prepared with a polyisocyanate and cross-linking agent |
| US10226405B2 (en) | 2009-09-18 | 2019-03-12 | International Flavors & Fragrances Inc. | Purified polyurea capsules, methods of preparation, and products containing the same |
| FR2954910B1 (fr) * | 2010-01-05 | 2012-02-10 | Oreal | Composition cosmetique comprenant des capsules fonctionnalisees, |
| DE202011110323U1 (de) | 2010-09-07 | 2013-07-10 | Latexco Nv | Funktionalisierter latexbasierter Schaum |
| EP2425961A1 (en) | 2010-09-07 | 2012-03-07 | Latexco NV | Functionalized latex based foam |
| AU2011360928A1 (en) * | 2010-11-10 | 2013-06-20 | Battelle Memorial Institute | Self-assembling polymer particle release system |
| US8673448B2 (en) | 2011-03-04 | 2014-03-18 | Outlast Technologies Llc | Articles containing precisely branched functional polymeric phase change materials |
| EP3154507B1 (en) * | 2014-06-13 | 2023-08-23 | Firmenich SA | Process for preparing polyurea microcapsules with improved deposition |
| DE102014213311A1 (de) * | 2014-07-09 | 2016-01-14 | Henkel Ag & Co. Kgaa | Neuartiges Waschverfahren mit elektrochemisch aktivierbarer Mediatorverbindung |
| US10003053B2 (en) | 2015-02-04 | 2018-06-19 | Global Web Horizons, Llc | Systems, structures and materials for electrochemical device thermal management |
| US10431858B2 (en) | 2015-02-04 | 2019-10-01 | Global Web Horizons, Llc | Systems, structures and materials for electrochemical device thermal management |
| US10138324B2 (en) * | 2015-08-11 | 2018-11-27 | Momentive Performance Materials Inc. | Process for the preparation of silylated polymers having low color and color stability |
| US9828459B2 (en) * | 2015-08-11 | 2017-11-28 | Momentive Performance Materials Inc. | Process for the preparation of silylated polymers employing a backmixing step |
| SG11201803900UA (en) * | 2015-12-15 | 2018-06-28 | Firmenich & Cie | Process for preparing polyurea microcapsules with improved deposition |
| US20190184364A1 (en) * | 2016-05-03 | 2019-06-20 | International Flavors & Fragrances Inc. | Fragrance compositions containing microcapsules |
| CN109069359A (zh) * | 2016-05-03 | 2018-12-21 | 国际香料和香精公司 | 可重载的微胶囊 |
| US10730993B2 (en) * | 2016-12-15 | 2020-08-04 | The Government Of The United States Of America, As Represented By The Secretary Of The Navy | Silyl-containing alcohols and amines for thermosets that disassemble on-demand |
| USD911961S1 (en) | 2017-04-03 | 2021-03-02 | Latent Heat Solutions, Llc | Battery container |
| US11254773B2 (en) * | 2017-05-11 | 2022-02-22 | The Regents Of The University Of California | Nanoscale multiple emulsions and nanoparticles |
| US20220072498A1 (en) * | 2019-05-21 | 2022-03-10 | FlRMENICH SA | Process for preparing microcapsules |
| BR112022012660A8 (pt) | 2020-01-29 | 2023-05-09 | Huntsman Adv Mat Switzerland | Partículas funcionalizadas |
| CN111440286A (zh) * | 2020-03-12 | 2020-07-24 | 济南大学 | 一种手性Co-MOF/CoSR/PU核壳复合材料的制备方法与应用 |
| DE102020110905A1 (de) | 2020-04-22 | 2021-10-28 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung eingetragener Verein | Kern-Schale Kapseln für die Textilveredelung |
| CN111530389B (zh) * | 2020-05-08 | 2022-08-12 | 上海应用技术大学 | 一种复合壁材包覆天然精油微胶囊及其制备方法 |
| CN117507082B (zh) * | 2023-11-06 | 2026-02-06 | 安徽农业大学 | 一种改性软化单板的制备方法及改性曲形家具材料的制备方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5112540A (en) * | 1989-12-14 | 1992-05-12 | The Mead Corporation | Method of making microcapsules having an improved pre-wall |
| US5342556A (en) * | 1991-09-16 | 1994-08-30 | Bayer Aktiengesellschaft | Microcapsules made of isocyanates with groups containing polyethylene oxide |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA935955A (en) * | 1969-08-22 | 1973-10-30 | Kanegafuchi Boseki Kabushiki Kaisha | Process of treating fibrous articles with microcapsules containing hydrophobic treating agent |
| JPH026671A (ja) * | 1988-05-18 | 1990-01-10 | Kanebo Ltd | 耐久性香気処理方法 |
| US5225308A (en) * | 1990-04-11 | 1993-07-06 | Kao Corporation | Encapsulated toner for heat-and-pressure fixing |
| WO1993017165A1 (en) | 1992-02-28 | 1993-09-02 | E.I. Du Pont De Nemours And Company | Fluorocarbamate soil-release agents |
| JP2915206B2 (ja) * | 1992-05-19 | 1999-07-05 | 富士写真フイルム株式会社 | 感熱記録材料 |
| MY116477A (en) * | 1993-05-17 | 2004-02-28 | Ciba Sc Holding Ag | Reactive dyes, processes for their preparation and their use |
| JP3913298B2 (ja) * | 1996-11-08 | 2007-05-09 | 株式会社クラレ | 微小カプセルの製造方法 |
| CA2311192A1 (en) | 2000-06-12 | 2001-12-12 | Harald D. H. Stover | Encapsulation process using isocyanate moieties |
| JP2002144738A (ja) * | 2000-11-09 | 2002-05-22 | Fuji Photo Film Co Ltd | マイクロカプセルの製造方法及び感熱記録材料 |
| DE10138996A1 (de) | 2001-08-15 | 2003-02-27 | Basf Ag | Mikrokapseldispersion |
| WO2003061817A1 (de) * | 2002-01-24 | 2003-07-31 | Bayer Aktiengesellschaft | Mikrokapseln enthaltende koagulate |
| DE10204979A1 (de) * | 2002-02-06 | 2003-08-14 | Basf Ag | Verfahren zur Herstellung hochfunktioneller hochverzweigter Polyharnstoffe |
| JP2004148245A (ja) * | 2002-10-31 | 2004-05-27 | Fuji Photo Film Co Ltd | 新規なマイクロカプセル及びそれを用いた感熱記録材料 |
-
2005
- 2005-07-25 JP JP2007524327A patent/JP5419353B2/ja not_active Expired - Fee Related
- 2005-07-25 EP EP20050776126 patent/EP1773484B1/en not_active Expired - Lifetime
- 2005-07-25 MX MX2007001369A patent/MX2007001369A/es active IP Right Grant
- 2005-07-25 CN CN200580033826A patent/CN100577278C/zh not_active Expired - Fee Related
- 2005-07-25 WO PCT/EP2005/053595 patent/WO2006013165A1/en not_active Ceased
- 2005-07-25 US US11/658,518 patent/US8546509B2/en not_active Expired - Fee Related
- 2005-07-25 BR BRPI0514050-1A patent/BRPI0514050B1/pt not_active IP Right Cessation
- 2005-07-25 KR KR1020077002707A patent/KR101219118B1/ko not_active Expired - Fee Related
- 2005-08-02 TW TW094126123A patent/TWI447137B/zh not_active IP Right Cessation
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2012
- 2012-04-04 JP JP2012085669A patent/JP2012144739A/ja active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5112540A (en) * | 1989-12-14 | 1992-05-12 | The Mead Corporation | Method of making microcapsules having an improved pre-wall |
| US5342556A (en) * | 1991-09-16 | 1994-08-30 | Bayer Aktiengesellschaft | Microcapsules made of isocyanates with groups containing polyethylene oxide |
Also Published As
| Publication number | Publication date |
|---|---|
| CN100577278C (zh) | 2010-01-06 |
| MX2007001369A (es) | 2007-04-10 |
| TW200613352A (en) | 2006-05-01 |
| US20110077375A1 (en) | 2011-03-31 |
| JP2008509237A (ja) | 2008-03-27 |
| CN101035613A (zh) | 2007-09-12 |
| BRPI0514050A (pt) | 2008-05-27 |
| EP1773484A1 (en) | 2007-04-18 |
| KR101219118B1 (ko) | 2013-01-14 |
| WO2006013165A1 (en) | 2006-02-09 |
| EP1773484B1 (en) | 2015-05-13 |
| BRPI0514050B1 (pt) | 2018-01-23 |
| KR20070049154A (ko) | 2007-05-10 |
| JP5419353B2 (ja) | 2014-02-19 |
| JP2012144739A (ja) | 2012-08-02 |
| US8546509B2 (en) | 2013-10-01 |
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