DE2425762A1 - Verfahren zur herstellung von mikrokapseln - Google Patents
Verfahren zur herstellung von mikrokapselnInfo
- Publication number
- DE2425762A1 DE2425762A1 DE19742425762 DE2425762A DE2425762A1 DE 2425762 A1 DE2425762 A1 DE 2425762A1 DE 19742425762 DE19742425762 DE 19742425762 DE 2425762 A DE2425762 A DE 2425762A DE 2425762 A1 DE2425762 A1 DE 2425762A1
- Authority
- DE
- Germany
- Prior art keywords
- water
- undecane
- bis
- tetraoxaspiro
- compound
- 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.)
- Ceased
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 18
- 239000003094 microcapsule Substances 0.000 title claims description 16
- 238000000034 method Methods 0.000 claims description 62
- -1 heterocyclic diamine Chemical class 0.000 claims description 47
- 239000000463 material Substances 0.000 claims description 40
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 37
- 150000001875 compounds Chemical class 0.000 claims description 34
- 239000002798 polar solvent Substances 0.000 claims description 16
- 230000002209 hydrophobic effect Effects 0.000 claims description 15
- 150000002894 organic compounds Chemical class 0.000 claims description 15
- 239000002245 particle Substances 0.000 claims description 14
- 229920005989 resin Polymers 0.000 claims description 12
- 239000011347 resin Substances 0.000 claims description 12
- 239000004593 Epoxy Substances 0.000 claims description 10
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 10
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- ANOPCGQVRXJHHD-UHFFFAOYSA-N 3-[3-(3-aminopropyl)-2,4,8,10-tetraoxaspiro[5.5]undecan-9-yl]propan-1-amine Chemical compound C1OC(CCCN)OCC21COC(CCCN)OC2 ANOPCGQVRXJHHD-UHFFFAOYSA-N 0.000 claims description 8
- 239000007795 chemical reaction product Substances 0.000 claims description 8
- 238000010438 heat treatment Methods 0.000 claims description 8
- 125000002947 alkylene group Chemical group 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 239000007787 solid Substances 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 6
- 125000000466 oxiranyl group Chemical group 0.000 claims description 6
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 6
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 5
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- FPEBQLGHNCMROL-UHFFFAOYSA-N 5-[3-(5-aminopentyl)-2,4,8,10-tetraoxaspiro[5.5]undecan-9-yl]pentan-1-amine Chemical compound C1OC(CCCCCN)OCC21COC(CCCCCN)OC2 FPEBQLGHNCMROL-UHFFFAOYSA-N 0.000 claims description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 239000004202 carbamide Substances 0.000 claims description 3
- 125000005456 glyceride group Chemical group 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 239000010695 polyglycol Substances 0.000 claims description 3
- 229920000151 polyglycol Polymers 0.000 claims description 3
- NRPKCOKHLCZPIF-UHFFFAOYSA-N 7-[3-(7-aminoheptyl)-2,4,8,10-tetraoxaspiro[5.5]undecan-9-yl]heptan-1-amine Chemical compound C1OC(CCCCCCCN)OCC21COC(CCCCCCCN)OC2 NRPKCOKHLCZPIF-UHFFFAOYSA-N 0.000 claims description 2
- 229930185605 Bisphenol Natural products 0.000 claims description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 2
- 150000001266 acyl halides Chemical class 0.000 claims description 2
- 150000001299 aldehydes Chemical class 0.000 claims description 2
- 125000000524 functional group Chemical group 0.000 claims description 2
- 150000007519 polyprotic acids Polymers 0.000 claims description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 2
- 239000008158 vegetable oil Substances 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims 1
- UDGUURODQNLMNO-UHFFFAOYSA-N 4-[3-(5-amino-2-methylpentan-2-yl)-2,4,8,10-tetraoxaspiro[5.5]undecan-9-yl]-4-methylpentan-1-amine Chemical compound C1OC(C(C)(CCCN)C)OCC21COC(C(C)(C)CCCN)OC2 UDGUURODQNLMNO-UHFFFAOYSA-N 0.000 claims 1
- 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 claims 1
- 239000002775 capsule Substances 0.000 description 77
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 27
- 239000000839 emulsion Substances 0.000 description 21
- 239000007788 liquid Substances 0.000 description 18
- 239000003921 oil Substances 0.000 description 15
- 235000019198 oils Nutrition 0.000 description 15
- 238000005538 encapsulation Methods 0.000 description 14
- 238000003756 stirring Methods 0.000 description 14
- 239000000243 solution Substances 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
- 238000006116 polymerization reaction Methods 0.000 description 11
- 239000007864 aqueous solution Substances 0.000 description 10
- 239000011162 core material Substances 0.000 description 10
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 10
- 239000004372 Polyvinyl alcohol Substances 0.000 description 9
- 150000004985 diamines Chemical class 0.000 description 9
- 229920002451 polyvinyl alcohol Polymers 0.000 description 9
- 239000002304 perfume Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000000178 monomer Substances 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 238000005354 coacervation Methods 0.000 description 6
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 description 5
- 239000000084 colloidal system Substances 0.000 description 5
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 5
- 229940015043 glyoxal Drugs 0.000 description 5
- 229920000647 polyepoxide Polymers 0.000 description 5
- 238000007127 saponification reaction Methods 0.000 description 5
- LIZLYZVAYZQVPG-UHFFFAOYSA-N (3-bromo-2-fluorophenyl)methanol Chemical compound OCC1=CC=CC(Br)=C1F LIZLYZVAYZQVPG-UHFFFAOYSA-N 0.000 description 4
- YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 description 4
- KUBDPQJOLOUJRM-UHFFFAOYSA-N 2-(chloromethyl)oxirane;4-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound ClCC1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 KUBDPQJOLOUJRM-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 238000006266 etherification reaction Methods 0.000 description 4
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 3
- 238000012695 Interfacial polymerization Methods 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZKURGBYDCVNWKH-UHFFFAOYSA-N [3,7-bis(dimethylamino)phenothiazin-10-yl]-phenylmethanone Chemical compound C12=CC=C(N(C)C)C=C2SC2=CC(N(C)C)=CC=C2N1C(=O)C1=CC=CC=C1 ZKURGBYDCVNWKH-UHFFFAOYSA-N 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 235000013877 carbamide Nutrition 0.000 description 3
- 239000001768 carboxy methyl cellulose Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 125000002091 cationic group Chemical group 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000003822 epoxy resin Substances 0.000 description 3
- 230000005484 gravity Effects 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 238000005191 phase separation Methods 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 2
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 2
- 244000215068 Acacia senegal Species 0.000 description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- 229920002261 Corn starch Polymers 0.000 description 2
- 229920002085 Dialdehyde starch Polymers 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N Glycolaldehyde Chemical compound OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 229920000084 Gum arabic Polymers 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 229920000877 Melamine resin Polymers 0.000 description 2
- AIJULSRZWUXGPQ-UHFFFAOYSA-N Methylglyoxal Chemical compound CC(=O)C=O AIJULSRZWUXGPQ-UHFFFAOYSA-N 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 229920001807 Urea-formaldehyde Polymers 0.000 description 2
- 239000000205 acacia gum Substances 0.000 description 2
- 235000010489 acacia gum Nutrition 0.000 description 2
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 2
- KADNTLDIZHQFCB-UHFFFAOYSA-N benzo[f]chromene Chemical compound C1=CC2=CC=CC=C2C2=C1OC=C=C2 KADNTLDIZHQFCB-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 2
- 229940105329 carboxymethylcellulose Drugs 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 239000008120 corn starch Substances 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- JBSLOWBPDRZSMB-FPLPWBNLSA-N dibutyl (z)-but-2-enedioate Chemical compound CCCCOC(=O)\C=C/C(=O)OCCCC JBSLOWBPDRZSMB-FPLPWBNLSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 239000003350 kerosene Substances 0.000 description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- 239000003607 modifier Substances 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- 229920002401 polyacrylamide Polymers 0.000 description 2
- 238000006068 polycondensation reaction Methods 0.000 description 2
- 238000007639 printing Methods 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 1
- QTKIQLNGOKOPOE-UHFFFAOYSA-N 1,1'-biphenyl;propane Chemical group CCC.C1=CC=CC=C1C1=CC=CC=C1 QTKIQLNGOKOPOE-UHFFFAOYSA-N 0.000 description 1
- IAUKWGFWINVWKS-UHFFFAOYSA-N 1,2-di(propan-2-yl)naphthalene Chemical compound C1=CC=CC2=C(C(C)C)C(C(C)C)=CC=C21 IAUKWGFWINVWKS-UHFFFAOYSA-N 0.000 description 1
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical group CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- YVEBEBZYLHREDB-UHFFFAOYSA-N 2-(dimethoxymethyl)pentanenitrile Chemical compound COC(C(CCC)C#N)OC YVEBEBZYLHREDB-UHFFFAOYSA-N 0.000 description 1
- JYXMZNSHJLYESN-UHFFFAOYSA-N 2-[3-(2-aminoethyl)-2,4,8,10-tetraoxaspiro[5.5]undecan-9-yl]ethanamine Chemical compound C1OC(CCN)OCC21COC(CCN)OC2 JYXMZNSHJLYESN-UHFFFAOYSA-N 0.000 description 1
- WGVGKMDCVXXQFO-UHFFFAOYSA-N 2-[3-(2-aminoethyl)-3,9-diethyl-2,4,8,10-tetraoxaspiro[5.5]undecan-9-yl]ethanamine Chemical compound C1OC(CC)(CCN)OCC21COC(CC)(CCN)OC2 WGVGKMDCVXXQFO-UHFFFAOYSA-N 0.000 description 1
- HHXYJYBYNZMZKX-UHFFFAOYSA-N 3,4:15,16-diepoxy-7-oxo-13(16),14-clerodadien-20,12-olide-(3alpha,4alpha)-form Natural products C12CCC3C4(C)CCCC(C)(C)C4CCC3(C)C1(C)CCC1C2(C)CCC1C(=C)C HHXYJYBYNZMZKX-UHFFFAOYSA-N 0.000 description 1
- FOGYNLXERPKEGN-UHFFFAOYSA-N 3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfopropyl)phenoxy]propane-1-sulfonic acid Chemical compound COC1=CC=CC(CC(CS(O)(=O)=O)OC=2C(=CC(CCCS(O)(=O)=O)=CC=2)OC)=C1O FOGYNLXERPKEGN-UHFFFAOYSA-N 0.000 description 1
- KGFUGLZSONHTTJ-UHFFFAOYSA-N 3-piperazin-1-ylpropane-1,1-diamine Chemical compound NC(N)CCN1CCNCC1 KGFUGLZSONHTTJ-UHFFFAOYSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- RTZAMMJCRUHEPM-UHFFFAOYSA-N 5-[3-(4-cyanobutyl)-2,4,8,10-tetraoxaspiro[5.5]undecan-9-yl]pentanenitrile Chemical compound C1OC(CCCCC#N)OCC21COC(CCCCC#N)OC2 RTZAMMJCRUHEPM-UHFFFAOYSA-N 0.000 description 1
- FKALNUSVHDCHRH-UHFFFAOYSA-N 7-[3-(6-cyanohexyl)-2,4,8,10-tetraoxaspiro[5.5]undecan-9-yl]heptanenitrile Chemical compound C1OC(CCCCCCC#N)OCC21COC(CCCCCCC#N)OC2 FKALNUSVHDCHRH-UHFFFAOYSA-N 0.000 description 1
- JPQCKFNUHDWJRE-UHFFFAOYSA-N 8,8-dimethoxyoctanenitrile Chemical compound COC(OC)CCCCCCC#N JPQCKFNUHDWJRE-UHFFFAOYSA-N 0.000 description 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 1
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- SQSPRWMERUQXNE-UHFFFAOYSA-N Guanylurea Chemical compound NC(=N)NC(N)=O SQSPRWMERUQXNE-UHFFFAOYSA-N 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 244000151018 Maranta arundinacea Species 0.000 description 1
- 235000010804 Maranta arundinacea Nutrition 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 229920002873 Polyethylenimine Polymers 0.000 description 1
- 229920002396 Polyurea Polymers 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical class OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 235000012419 Thalia geniculata Nutrition 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 235000010724 Wisteria floribunda Nutrition 0.000 description 1
- USDJGQLNFPZEON-UHFFFAOYSA-N [[4,6-bis(hydroxymethylamino)-1,3,5-triazin-2-yl]amino]methanol Chemical compound OCNC1=NC(NCO)=NC(NCO)=N1 USDJGQLNFPZEON-UHFFFAOYSA-N 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 229960001138 acetylsalicylic acid Drugs 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- YQLZOAVZWJBZSY-UHFFFAOYSA-N decane-1,10-diamine Chemical compound NCCCCCCCCCCN YQLZOAVZWJBZSY-UHFFFAOYSA-N 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- ZZTURJAZCMUWEP-UHFFFAOYSA-N diaminomethylideneazanium;hydrogen sulfate Chemical compound NC(N)=N.OS(O)(=O)=O ZZTURJAZCMUWEP-UHFFFAOYSA-N 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- UPBDXRPQPOWRKR-UHFFFAOYSA-N furan-2,5-dione;methoxyethene Chemical compound COC=C.O=C1OC(=O)C=C1 UPBDXRPQPOWRKR-UHFFFAOYSA-N 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000007902 hard capsule Substances 0.000 description 1
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 1
- 229920001477 hydrophilic polymer Polymers 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000002372 labelling Methods 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 229940041616 menthol Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- QOHMWDJIBGVPIF-UHFFFAOYSA-N n',n'-diethylpropane-1,3-diamine Chemical compound CCN(CC)CCCN QOHMWDJIBGVPIF-UHFFFAOYSA-N 0.000 description 1
- FJDUDHYHRVPMJZ-UHFFFAOYSA-N nonan-1-amine Chemical compound CCCCCCCCCN FJDUDHYHRVPMJZ-UHFFFAOYSA-N 0.000 description 1
- SXJVFQLYZSNZBT-UHFFFAOYSA-N nonane-1,9-diamine Chemical compound NCCCCCCCCCN SXJVFQLYZSNZBT-UHFFFAOYSA-N 0.000 description 1
- KIHUPOKUSVEICJ-UHFFFAOYSA-N nonyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 KIHUPOKUSVEICJ-UHFFFAOYSA-N 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000001254 oxidized starch Substances 0.000 description 1
- 235000013808 oxidized starch Nutrition 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 238000011197 physicochemical method Methods 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 229920005597 polymer membrane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920003226 polyurethane urea Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229950000244 sulfanilic acid Drugs 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000001911 terphenyls Chemical class 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 229940100445 wheat starch Drugs 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
- B01J13/18—In situ polymerisation with all reactants being present in the same phase
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Dispersion Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Manufacturing Of Micro-Capsules (AREA)
- Medicinal Preparation (AREA)
- Fats And Perfumes (AREA)
- Adhesive Tapes (AREA)
- Paints Or Removers (AREA)
- Color Printing (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5959173A JPS5343152B2 (en, 2012) | 1973-05-28 | 1973-05-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2425762A1 true DE2425762A1 (de) | 1975-01-02 |
Family
ID=13117616
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19742425762 Ceased DE2425762A1 (de) | 1973-05-28 | 1974-05-28 | Verfahren zur herstellung von mikrokapseln |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3996156A (en, 2012) |
| JP (1) | JPS5343152B2 (en, 2012) |
| BE (1) | BE815604A (en, 2012) |
| DE (1) | DE2425762A1 (en, 2012) |
| ES (1) | ES426699A1 (en, 2012) |
| GB (1) | GB1475128A (en, 2012) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4000087A (en) * | 1974-07-29 | 1976-12-28 | Moore Business Forms, Inc. | Microcapsules useful in carbonless copying systems and process for their preparation |
| GB1524742A (en) * | 1976-01-19 | 1978-09-13 | Wiggins Teape Ltd | Pressure-sensitive copying paper |
| FR2413123A1 (fr) * | 1977-12-30 | 1979-07-27 | Philagro Sa | Procede d'encapsulation par polycondensation interfaciale |
| US4282255A (en) * | 1979-06-28 | 1981-08-04 | State Of Oregon, By And Through The Oregon State Board Of Higher Education On Behalf Of Oregon State University | Method and starter compositions for the growth of acid producing bacteria and bacterial compositions produced thereby |
| USRE32079E (en) * | 1979-06-28 | 1986-02-04 | State Of Oregon, By And Through The Oregon State Board Of Higher Education On Behalf Of Oregon State University | Method and starter compositions for the growth of acid producing bacteria and bacterial compositions produced thereby |
| JPS60205974A (ja) * | 1984-03-28 | 1985-10-17 | Shin Kobe Electric Mach Co Ltd | 燃料電池 |
| JPS61133576A (ja) * | 1984-12-01 | 1986-06-20 | Toshiba Corp | 燃料電池発電システム |
| US5385959A (en) * | 1992-04-29 | 1995-01-31 | Lever Brothers Company, Division Of Conopco, Inc. | Capsule which comprises a component subject to degradation and a composite polymer |
| US5281355A (en) * | 1992-04-29 | 1994-01-25 | Lever Brothers Company, Division Of Conopco, Inc. | Heavy duty liquid detergent compositions containing a capsule which comprises a component subject to degradation and a composite polymer |
| US5281357A (en) * | 1993-03-25 | 1994-01-25 | Lever Brothers Company, Division Of Conopco, Inc. | Protease containing heavy duty liquid detergent compositions comprising capsules comprising non-proteolytic enzyme and composite polymer |
| US5922652A (en) | 1992-05-05 | 1999-07-13 | Procter & Gamble | Microencapsulated oil field chemicals |
| US5281356A (en) * | 1993-03-25 | 1994-01-25 | Lever Brothers Company | Heavy duty liquid detergent compositions containing non-proteolytic enzymes comprising capsules comprising proteolytic enzyme and composite polymer |
| US5354366A (en) * | 1993-09-27 | 1994-10-11 | Deluxe Corporation | Ink composition and resins and methods relating thereto |
| US5591146A (en) * | 1996-01-17 | 1997-01-07 | The Procter & Gamble Company | Sanitary napkin with perfume-bearing microcapsule adhesive |
| US5769832A (en) * | 1996-04-17 | 1998-06-23 | Hasse; Margaret Henderson | Absorbent article with odor masking agents released by the fastening system |
| US6242167B1 (en) | 1999-04-12 | 2001-06-05 | Rentech, Inc. | Developer for use with carbonless copy paper and photo imaging systems |
| US20030216488A1 (en) | 2002-04-18 | 2003-11-20 | The Procter & Gamble Company | Compositions comprising a dispersant and microcapsules containing an active material |
| AR040093A1 (es) * | 2002-05-21 | 2005-03-16 | Procter & Gamble | Composicion limpiadora que comprende perlas suspendidas |
| US20030224030A1 (en) | 2002-05-23 | 2003-12-04 | Hirotaka Uchiyama | Methods and articles for reducing airborne particulates |
| US7919666B2 (en) * | 2002-12-31 | 2011-04-05 | Kimberly-Clark Worldwide, Inc. | Personal care articles with fragrance delivery system |
| US7004313B2 (en) * | 2002-12-31 | 2006-02-28 | Kimberly-Clark Worldwide, Inc. | Disposable dispenser with fragrance delivery system |
| EP2070510A1 (en) | 2007-12-10 | 2009-06-17 | Takasago International Corporation | Personal cleansing system |
| US20100268191A1 (en) * | 2009-04-21 | 2010-10-21 | Medtronic Vascular, Inc. | Drug Delivery Catheter using Frangible Microcapsules and Delivery Method |
| US8951708B2 (en) | 2013-06-05 | 2015-02-10 | Xerox Corporation | Method of making toners |
| WO2018030431A1 (en) | 2016-08-09 | 2018-02-15 | Takasago International Corporation | Solid composition comprising free and encapsulated fragrances |
| CA3051268C (en) | 2016-11-21 | 2022-11-29 | Bell Flavors & Fragrances, Inc. | Malodor counteractant composition and methods |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1444414A1 (de) * | 1961-03-13 | 1969-01-23 | Minnesota Mining & Mfg | Mikrozellen-Produkt und Verfahren zu seiner Herstellung |
| US3432327A (en) * | 1964-03-13 | 1969-03-11 | Pilot Pen Co Ltd | Pressure sensitive copying sheet and the production thereof |
| DE1519853A1 (de) * | 1963-10-21 | 1971-01-21 | Pilot Pen Co Ltd | Verfahren zum Einkapseln von Troepfchen dispergierter Fluessigkeiten |
| US3577515A (en) * | 1963-12-13 | 1971-05-04 | Pennwalt Corp | Encapsulation by interfacial polycondensation |
| DE2404412A1 (de) * | 1973-01-30 | 1974-08-01 | Fuji Photo Film Co Ltd | Verfahren zur herstellung von mikrokapselfilmen mit niedriger porositaet |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2996517A (en) * | 1957-12-30 | 1961-08-15 | Union Carbide Corp | Production of diesters, diacids, dinitriles and mixed ester nitriles containing the spirobi m-dioxane group |
-
1973
- 1973-05-28 JP JP5959173A patent/JPS5343152B2/ja not_active Expired
-
1974
- 1974-05-27 ES ES426699A patent/ES426699A1/es not_active Expired
- 1974-05-28 GB GB2367274A patent/GB1475128A/en not_active Expired
- 1974-05-28 DE DE19742425762 patent/DE2425762A1/de not_active Ceased
- 1974-05-28 BE BE144805A patent/BE815604A/xx unknown
- 1974-05-28 US US05/473,981 patent/US3996156A/en not_active Expired - Lifetime
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1444414A1 (de) * | 1961-03-13 | 1969-01-23 | Minnesota Mining & Mfg | Mikrozellen-Produkt und Verfahren zu seiner Herstellung |
| DE1519853A1 (de) * | 1963-10-21 | 1971-01-21 | Pilot Pen Co Ltd | Verfahren zum Einkapseln von Troepfchen dispergierter Fluessigkeiten |
| US3577515A (en) * | 1963-12-13 | 1971-05-04 | Pennwalt Corp | Encapsulation by interfacial polycondensation |
| US3432327A (en) * | 1964-03-13 | 1969-03-11 | Pilot Pen Co Ltd | Pressure sensitive copying sheet and the production thereof |
| DE2404412A1 (de) * | 1973-01-30 | 1974-08-01 | Fuji Photo Film Co Ltd | Verfahren zur herstellung von mikrokapselfilmen mit niedriger porositaet |
Also Published As
| Publication number | Publication date |
|---|---|
| US3996156A (en) | 1976-12-07 |
| ES426699A1 (es) | 1976-07-16 |
| GB1475128A (en) | 1977-06-01 |
| BE815604A (fr) | 1974-09-16 |
| JPS5343152B2 (en, 2012) | 1978-11-17 |
| JPS508780A (en, 2012) | 1975-01-29 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2425762A1 (de) | Verfahren zur herstellung von mikrokapseln | |
| DE2434406A1 (de) | Verfahren zur herstellung von mikrokapseln | |
| US3516846A (en) | Microcapsule-containing paper | |
| DE3114035C3 (en, 2012) | ||
| DE2652875C2 (de) | Verkapselungsverfahren für die Herstellung von Mikrokapseln | |
| US3516941A (en) | Microcapsules and process of making | |
| DE2946029C2 (en, 2012) | ||
| DE2310820A1 (de) | Verfahren zur herstellung von durch druck zerstoerbaren mikrokapseln durch grenzflaechenvernetzung von emulgator, nach dem verfahren hergestellte mikrokapseln und ihre verwendung in uebertragungskopiesystemen | |
| US3755190A (en) | Capsule manufacture | |
| US4062799A (en) | Method of forming microcapsule films having low porosity | |
| DE1619802A1 (de) | Verfahren zum Einkapseln feiner Troepfchen von dispergierten Fluessigkeiten | |
| DE3030801A1 (de) | Verfahren zur herstellung von doppelkapseln | |
| DE2242910A1 (de) | Verfahren zur herstellung von feinen oelhaltigen mikrokapseln mit starken schutzschalen | |
| DE1817316A1 (de) | Kapsel mit mehrschichtiger Huelle und Verfahren zu ihrer Herstellung | |
| DE2611044A1 (de) | Verfahren zur herstellung von mikrokapseln durch grenzflaechenvernetzung und nach dem verfahren hergestellte mikrokapseln | |
| EP0321750A1 (de) | Verfahren zur Herstellung von Mikrokapseln, die danach erhältlichen Mikrokapseln und deren Verwendung | |
| DE2417297A1 (de) | In sich geschlossenes, unabhaengiges, druckempfindliches aufzeichnungssystem und verfahren zu seiner herstellung | |
| DE2453886A1 (de) | Verfahren zur einkapselung von mit wasser nicht mischbaren substanzen | |
| DE3241020C2 (de) | Mikrokapseln für auf Druck ansprechendes Aufzeichnungspapier und Verfahren zur Herstellung derselben | |
| DE2726539A1 (de) | Verkapselungsverfahren | |
| DE3110281C2 (en, 2012) | ||
| US4670344A (en) | Microcapsule for pressure-sensitive recording paper and process of preparing same | |
| US4209188A (en) | Microcapsules, method of making same, and carbonless copying system including said microcapsules | |
| DE3202551C2 (en, 2012) | ||
| DE2342066A1 (de) | Verfahren zum herstellen von mikrokapseln |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8176 | Proceedings suspended because of application no: |
Ref document number: 2404412 Country of ref document: DE Format of ref document f/p: P |
|
| 8128 | New person/name/address of the agent |
Representative=s name: KOHLER, M., DIPL.-CHEM. DR.RER.NAT., PAT.-ANW., 80 |
|
| 8178 | Suspension cancelled | ||
| 8128 | New person/name/address of the agent |
Representative=s name: SOLF, A., DR.-ING., 8000 MUENCHEN ZAPF, C., DIPL.- |
|
| 8131 | Rejection |