AU2002316861B2 - Colourants encapsulated in a polymer matrix - Google Patents
Colourants encapsulated in a polymer matrix Download PDFInfo
- Publication number
- AU2002316861B2 AU2002316861B2 AU2002316861A AU2002316861A AU2002316861B2 AU 2002316861 B2 AU2002316861 B2 AU 2002316861B2 AU 2002316861 A AU2002316861 A AU 2002316861A AU 2002316861 A AU2002316861 A AU 2002316861A AU 2002316861 B2 AU2002316861 B2 AU 2002316861B2
- Authority
- AU
- Australia
- Prior art keywords
- monomer
- acid
- polymeric
- matrix
- anionic
- 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
- 239000011159 matrix material Substances 0.000 title claims abstract description 64
- 229920000642 polymer Polymers 0.000 title claims description 67
- 239000000178 monomer Substances 0.000 claims abstract description 107
- 239000002245 particle Substances 0.000 claims abstract description 63
- 238000000034 method Methods 0.000 claims abstract description 51
- 230000008569 process Effects 0.000 claims abstract description 40
- 239000000203 mixture Substances 0.000 claims abstract description 28
- 230000002209 hydrophobic effect Effects 0.000 claims abstract description 25
- 150000003839 salts Chemical group 0.000 claims abstract description 15
- 239000002537 cosmetic Substances 0.000 claims abstract description 14
- 230000009477 glass transition Effects 0.000 claims abstract description 11
- 229920001519 homopolymer Polymers 0.000 claims abstract description 8
- 125000000129 anionic group Chemical group 0.000 claims description 37
- 125000002091 cationic group Chemical group 0.000 claims description 31
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 29
- 239000002253 acid Substances 0.000 claims description 17
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 16
- 150000001412 amines Chemical class 0.000 claims description 16
- 239000008346 aqueous phase Substances 0.000 claims description 16
- 239000006185 dispersion Substances 0.000 claims description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 15
- 239000000049 pigment Substances 0.000 claims description 14
- 230000018044 dehydration Effects 0.000 claims description 13
- 238000006297 dehydration reaction Methods 0.000 claims description 13
- 239000007864 aqueous solution Substances 0.000 claims description 12
- 239000003381 stabilizer Substances 0.000 claims description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 10
- 239000003431 cross linking reagent Substances 0.000 claims description 10
- 239000000839 emulsion Substances 0.000 claims description 8
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 8
- 239000012458 free base Substances 0.000 claims description 7
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 claims description 6
- 229920001577 copolymer Polymers 0.000 claims description 6
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 6
- XHZPRMZZQOIPDS-UHFFFAOYSA-N 2-Methyl-2-[(1-oxo-2-propenyl)amino]-1-propanesulfonic acid Chemical compound OS(=O)(=O)CC(C)(C)NC(=O)C=C XHZPRMZZQOIPDS-UHFFFAOYSA-N 0.000 claims description 5
- WRAGBEWQGHCDDU-UHFFFAOYSA-M C([O-])([O-])=O.[NH4+].[Zr+] Chemical compound C([O-])([O-])=O.[NH4+].[Zr+] WRAGBEWQGHCDDU-UHFFFAOYSA-M 0.000 claims description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 5
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 5
- IAXXETNIOYFMLW-COPLHBTASA-N [(1s,3s,4s)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl] 2-methylprop-2-enoate Chemical compound C1C[C@]2(C)[C@@H](OC(=O)C(=C)C)C[C@H]1C2(C)C IAXXETNIOYFMLW-COPLHBTASA-N 0.000 claims description 5
- 229910021529 ammonia Inorganic materials 0.000 claims description 5
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 claims description 5
- OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 0.000 claims description 5
- 229940119545 isobornyl methacrylate Drugs 0.000 claims description 5
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 5
- 239000011976 maleic acid Substances 0.000 claims description 5
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 5
- QIWKUEJZZCOPFV-UHFFFAOYSA-N phenyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=CC=C1 QIWKUEJZZCOPFV-UHFFFAOYSA-N 0.000 claims description 5
- 238000001694 spray drying Methods 0.000 claims description 5
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 5
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 claims description 5
- 238000005292 vacuum distillation Methods 0.000 claims description 5
- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 claims description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 4
- WPKYZIPODULRBM-UHFFFAOYSA-N azane;prop-2-enoic acid Chemical compound N.OC(=O)C=C WPKYZIPODULRBM-UHFFFAOYSA-N 0.000 claims description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 4
- 238000004821 distillation Methods 0.000 claims description 4
- 235000019253 formic acid Nutrition 0.000 claims description 4
- UIIIBRHUICCMAI-UHFFFAOYSA-N prop-2-ene-1-sulfonic acid Chemical compound OS(=O)(=O)CC=C UIIIBRHUICCMAI-UHFFFAOYSA-N 0.000 claims description 4
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 claims description 4
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 claims description 4
- 239000002585 base Substances 0.000 claims description 3
- 239000007791 liquid phase Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 239000000976 ink Substances 0.000 abstract description 2
- 239000000123 paper Substances 0.000 abstract description 2
- 239000000975 dye Substances 0.000 description 22
- 239000003921 oil Substances 0.000 description 19
- 239000007788 liquid Substances 0.000 description 15
- 239000000463 material Substances 0.000 description 12
- 229920005989 resin Polymers 0.000 description 11
- 239000011347 resin Substances 0.000 description 11
- 239000004480 active ingredient Substances 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 102000004190 Enzymes Human genes 0.000 description 7
- 108090000790 Enzymes Proteins 0.000 description 7
- 238000005538 encapsulation Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000004132 cross linking Methods 0.000 description 5
- 239000003995 emulsifying agent Substances 0.000 description 4
- 230000000007 visual effect Effects 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000004945 emulsification Methods 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000001054 red pigment Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- CNPVJWYWYZMPDS-UHFFFAOYSA-N 2-methyldecane Chemical compound CCCCCCCCC(C)C CNPVJWYWYZMPDS-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- 229920000877 Melamine resin Polymers 0.000 description 2
- 239000005662 Paraffin oil Substances 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- 239000004411 aluminium Substances 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 229910052788 barium Inorganic materials 0.000 description 2
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical group CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000006081 fluorescent whitening agent Substances 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 239000001023 inorganic pigment Substances 0.000 description 2
- 235000013980 iron oxide Nutrition 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- -1 methylol functionality Chemical group 0.000 description 2
- 239000010445 mica Substances 0.000 description 2
- 229910052618 mica group Inorganic materials 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000000346 nonvolatile oil Substances 0.000 description 2
- 239000012860 organic pigment Substances 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- 150000004756 silanes Chemical class 0.000 description 2
- 230000003019 stabilising effect Effects 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 239000004160 Ammonium persulphate Substances 0.000 description 1
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- MBMLMWLHJBBADN-UHFFFAOYSA-N Ferrous sulfide Chemical class [Fe]=S MBMLMWLHJBBADN-UHFFFAOYSA-N 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- SJEYSFABYSGQBG-UHFFFAOYSA-M Patent blue Chemical compound [Na+].C1=CC(N(CC)CC)=CC=C1C(C=1C(=CC(=CC=1)S([O-])(=O)=O)S([O-])(=O)=O)=C1C=CC(=[N+](CC)CC)C=C1 SJEYSFABYSGQBG-UHFFFAOYSA-M 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- FHNINJWBTRXEBC-UHFFFAOYSA-N Sudan III Chemical compound OC1=CC=C2C=CC=CC2=C1N=NC(C=C1)=CC=C1N=NC1=CC=CC=C1 FHNINJWBTRXEBC-UHFFFAOYSA-N 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 239000000980 acid dye Substances 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 229920003180 amino resin Polymers 0.000 description 1
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 1
- 235000019395 ammonium persulphate Nutrition 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 229920005601 base polymer Polymers 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 239000001045 blue dye Substances 0.000 description 1
- 229940067573 brown iron oxide Drugs 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 229920006317 cationic polymer Polymers 0.000 description 1
- PZTQVMXMKVTIRC-UHFFFAOYSA-L chembl2028348 Chemical compound [Ca+2].[O-]S(=O)(=O)C1=CC(C)=CC=C1N=NC1=C(O)C(C([O-])=O)=CC2=CC=CC=C12 PZTQVMXMKVTIRC-UHFFFAOYSA-L 0.000 description 1
- 238000005354 coacervation Methods 0.000 description 1
- 239000003581 cosmetic carrier Substances 0.000 description 1
- 239000008406 cosmetic ingredient Substances 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- VPWFPZBFBFHIIL-UHFFFAOYSA-L disodium 4-[(4-methyl-2-sulfophenyl)diazenyl]-3-oxidonaphthalene-2-carboxylate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)C1=CC(C)=CC=C1N=NC1=C(O)C(C([O-])=O)=CC2=CC=CC=C12 VPWFPZBFBFHIIL-UHFFFAOYSA-L 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- IVJISJACKSSFGE-UHFFFAOYSA-N formaldehyde;1,3,5-triazine-2,4,6-triamine Chemical compound O=C.NC1=NC(N)=NC(N)=N1 IVJISJACKSSFGE-UHFFFAOYSA-N 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 229920001600 hydrophobic polymer Polymers 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 229910001867 inorganic solvent Inorganic materials 0.000 description 1
- 239000003049 inorganic solvent Substances 0.000 description 1
- VBMVTYDPPZVILR-UHFFFAOYSA-N iron(2+);oxygen(2-) Chemical class [O-2].[Fe+2] VBMVTYDPPZVILR-UHFFFAOYSA-N 0.000 description 1
- LDHBWEYLDHLIBQ-UHFFFAOYSA-M iron(3+);oxygen(2-);hydroxide;hydrate Chemical compound O.[OH-].[O-2].[Fe+3] LDHBWEYLDHLIBQ-UHFFFAOYSA-M 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 1
- 239000000391 magnesium silicate Substances 0.000 description 1
- 229910052919 magnesium silicate Inorganic materials 0.000 description 1
- 235000019792 magnesium silicate Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000010979 pH adjustment Methods 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- 239000001044 red dye Substances 0.000 description 1
- 239000013074 reference sample Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229940099373 sudan iii Drugs 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 239000000984 vat dye Substances 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 239000007762 w/o emulsion Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0097—Dye preparations of special physical nature; Tablets, films, extrusion, microcapsules, sheets, pads, bags with dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0001—Post-treatment of organic pigments or dyes
- C09B67/0004—Coated particulate pigments or dyes
- C09B67/0008—Coated particulate pigments or dyes with organic coatings
- C09B67/0013—Coated particulate pigments or dyes with organic coatings with polymeric coatings
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Cosmetics (AREA)
- Manufacturing Of Micro-Capsules (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Polymerisation Methods In General (AREA)
- Paints Or Removers (AREA)
- Immobilizing And Processing Of Enzymes And Microorganisms (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Pigments, Carbon Blacks, Or Wood Stains (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0110989.1A GB0110989D0 (en) | 2001-05-04 | 2001-05-04 | Process of entrapping colorants |
| GB0110989.1 | 2001-05-04 | ||
| PCT/EP2002/004348 WO2002090445A1 (en) | 2001-05-04 | 2002-04-19 | Colourants encapsulated in a polymer matrix |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2002316861A1 AU2002316861A1 (en) | 2003-05-01 |
| AU2002316861B2 true AU2002316861B2 (en) | 2006-11-30 |
Family
ID=9914056
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2002316861A Ceased AU2002316861B2 (en) | 2001-05-04 | 2002-04-19 | Colourants encapsulated in a polymer matrix |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US7648715B2 (https=) |
| EP (1) | EP1387867B1 (https=) |
| JP (1) | JP4141845B2 (https=) |
| KR (1) | KR100858835B1 (https=) |
| CN (1) | CN1244642C (https=) |
| AT (1) | ATE309305T1 (https=) |
| AU (1) | AU2002316861B2 (https=) |
| BR (1) | BRPI0209362B8 (https=) |
| CA (1) | CA2444715C (https=) |
| DE (1) | DE60207237T2 (https=) |
| GB (1) | GB0110989D0 (https=) |
| MX (1) | MXPA03010086A (https=) |
| NO (1) | NO325737B1 (https=) |
| RU (1) | RU2003133772A (https=) |
| WO (1) | WO2002090445A1 (https=) |
| ZA (1) | ZA200307622B (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11065593B2 (en) | 2015-09-03 | 2021-07-20 | Tagra Biotechnologies Ltd. | Microcapsules encapsulating a reflective agent |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8071078B2 (en) | 2003-02-26 | 2011-12-06 | Basf Se | Encapsulated colorants for natural skin appearance |
| WO2005123009A1 (en) * | 2004-06-15 | 2005-12-29 | Ciba Specialty Chemicals Holding Inc. | Shatter resistant encapsulated colorants for natural skin appearance |
| GB0413338D0 (en) * | 2004-06-15 | 2004-07-21 | Ciba Spec Chem Water Treat Ltd | Polymeric particles |
| CN100512792C (zh) * | 2004-06-15 | 2009-07-15 | 西巴特殊化学制品控股公司 | 用于自然皮肤外观的抗破碎性胶囊化着色剂 |
| ATE455151T1 (de) * | 2004-06-15 | 2010-01-15 | Basf Se | Polymerteilchen |
| US20060024340A1 (en) * | 2004-07-30 | 2006-02-02 | Elder Stewart T | Encapsulated fluorescent whitening compositions for improved surface appearance |
| WO2006027328A1 (en) * | 2004-09-10 | 2006-03-16 | Ciba Specialty Chemicals Holding Inc. | Encapsulated fluorescent whitening compositions and their use in personal care applications |
| GB2433939B (en) * | 2004-11-22 | 2007-12-05 | Kao Corp | Water-based inks for ink-jet printing |
| EP1871841A2 (en) * | 2005-04-21 | 2008-01-02 | Ciba SC Holding AG | Pigment formulations |
| EP1954795B8 (en) * | 2005-11-29 | 2009-08-26 | Basf Se | Capsules |
| US20070287789A1 (en) * | 2006-06-07 | 2007-12-13 | Stephen Ray Jones | Bleed-resistant colored microparticles |
| WO2008049749A1 (en) | 2006-10-25 | 2008-05-02 | Ciba Holding Inc. | Heat-stable encapsulated pigments |
| GB0623110D0 (en) * | 2006-11-21 | 2006-12-27 | Ciba Sc Holding Ag | Microcapules, their use and processes for their manufacture |
| IT1377153B (it) * | 2007-07-24 | 2010-07-12 | Univ Siena | "coloranti sostantivi fotostabili per la colorazione semipermanente dei capelli" |
| US8349452B2 (en) | 2008-03-03 | 2013-01-08 | Basf Se | Microcapsules, their preparation and use |
| CA2722681C (en) * | 2008-05-09 | 2013-07-09 | Basf Se | Polymer encapsulated colourants by spray drying |
| GB0911350D0 (en) * | 2009-07-01 | 2009-08-12 | Basf Se | Particulate composition |
| CN101921497B (zh) * | 2010-09-07 | 2012-10-31 | 珠海保税区天然宝杰数码科技材料有限公司 | 乳液型色料的制备方法 |
| US9192562B2 (en) * | 2013-09-18 | 2015-11-24 | L'oreal | High color intensity and easily removable mascara |
| EP3256563A1 (en) * | 2014-11-17 | 2017-12-20 | The Procter and Gamble Company | Benefit agent delivery compositions |
| CN104873410A (zh) * | 2015-05-04 | 2015-09-02 | 上海应用技术学院 | 一种负载脂溶性染料的甲基丙烯酸甲酯交联聚合物微粒及制备方法 |
| CN109423104B (zh) | 2017-07-14 | 2022-02-15 | 广东华润涂料有限公司 | 包含聚合物-无机颗粒复合物的水性分散体及其制备方法 |
| KR102793693B1 (ko) | 2018-03-30 | 2025-04-10 | 가부시키가이샤 코세 | 포스포릴콜린기 및 실리콘기 함유 공중합체, 상기 공중합체로 피복된 분체 및 그 제조 방법, 및 상기 공중합체 및 상기 분체의 화장료로의 이용 |
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| US3876603A (en) * | 1970-06-22 | 1975-04-08 | Ppg Industries Inc | Method of encapsulating pigments in organic dispersions of polymers |
| WO1997024178A1 (en) * | 1995-12-29 | 1997-07-10 | Allied Colloids Limited | Polymeric particulate materials and compositions containing them |
| US5744152A (en) * | 1988-08-24 | 1998-04-28 | Allied Colloids Limited | Polymeric compositions and methods of producing them |
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| JPH0757806B2 (ja) | 1987-04-16 | 1995-06-21 | 日本ペイント株式会社 | 着色微小樹脂粒子ならびにその製法 |
| JP2541290B2 (ja) | 1988-08-04 | 1996-10-09 | 日本エクスラン工業株式会社 | 着色ポリマ―ビ―ズ |
| US5219918A (en) * | 1988-10-20 | 1993-06-15 | The Dow Chemical Company | Copolymer coating compositions comprising sulfoalkyl monomeric emulsifier |
| DE4438563A1 (de) * | 1994-10-28 | 1996-05-02 | Hoechst Ag | Wäßrige Dispersionen für Grundierungen |
| FR2739024B1 (fr) * | 1995-09-21 | 1997-11-14 | Oreal | Composition cosmetique ou dermatologique aqueuse comprenant un oligomere filmogene et des particules nanometriques rigides et non-filmifiables ; utilisations |
| EP0823671B1 (en) * | 1996-08-05 | 2002-12-11 | Nippon Shokubai Co., Ltd. | Colored minute particles |
| JP3224510B2 (ja) | 1996-08-05 | 2001-10-29 | 株式会社日本触媒 | 着色微粒子の製造方法 |
| JP3684400B2 (ja) | 1997-04-23 | 2005-08-17 | 御国色素株式会社 | 水性顔料分散液の製造方法 |
| US6465556B1 (en) * | 1997-07-01 | 2002-10-15 | Rhodia Inc. | Latex made with crosslinkable surface active agent |
| US6214467B1 (en) | 1998-07-24 | 2001-04-10 | Rohm And Haas Company | Polymer-pigment composites |
| JP2000109736A (ja) | 1998-10-07 | 2000-04-18 | Fuji Xerox Co Ltd | 水性インク組成物およびその製造方法 |
-
2001
- 2001-05-04 GB GBGB0110989.1A patent/GB0110989D0/en not_active Ceased
-
2002
- 2002-04-19 CA CA002444715A patent/CA2444715C/en not_active Expired - Fee Related
- 2002-04-19 BR BRPI0209362A patent/BRPI0209362B8/pt not_active IP Right Cessation
- 2002-04-19 CN CNB028093224A patent/CN1244642C/zh not_active Expired - Fee Related
- 2002-04-19 AT AT02745245T patent/ATE309305T1/de not_active IP Right Cessation
- 2002-04-19 US US10/475,480 patent/US7648715B2/en not_active Expired - Fee Related
- 2002-04-19 RU RU2003133772/04A patent/RU2003133772A/ru not_active Application Discontinuation
- 2002-04-19 WO PCT/EP2002/004348 patent/WO2002090445A1/en not_active Ceased
- 2002-04-19 MX MXPA03010086A patent/MXPA03010086A/es active IP Right Grant
- 2002-04-19 DE DE60207237T patent/DE60207237T2/de not_active Expired - Lifetime
- 2002-04-19 EP EP02745245A patent/EP1387867B1/en not_active Expired - Lifetime
- 2002-04-19 KR KR1020037014373A patent/KR100858835B1/ko not_active Expired - Fee Related
- 2002-04-19 AU AU2002316861A patent/AU2002316861B2/en not_active Ceased
- 2002-04-19 JP JP2002587513A patent/JP4141845B2/ja not_active Expired - Fee Related
-
2003
- 2003-09-30 ZA ZA200307622A patent/ZA200307622B/en unknown
- 2003-10-30 NO NO20034853A patent/NO325737B1/no not_active IP Right Cessation
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3876603A (en) * | 1970-06-22 | 1975-04-08 | Ppg Industries Inc | Method of encapsulating pigments in organic dispersions of polymers |
| US5744152A (en) * | 1988-08-24 | 1998-04-28 | Allied Colloids Limited | Polymeric compositions and methods of producing them |
| WO1997024178A1 (en) * | 1995-12-29 | 1997-07-10 | Allied Colloids Limited | Polymeric particulate materials and compositions containing them |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11065593B2 (en) | 2015-09-03 | 2021-07-20 | Tagra Biotechnologies Ltd. | Microcapsules encapsulating a reflective agent |
Also Published As
| Publication number | Publication date |
|---|---|
| US7648715B2 (en) | 2010-01-19 |
| DE60207237D1 (de) | 2005-12-15 |
| KR100858835B1 (ko) | 2008-09-17 |
| ATE309305T1 (de) | 2005-11-15 |
| KR20030097849A (ko) | 2003-12-31 |
| GB0110989D0 (en) | 2001-06-27 |
| BR0209362A (pt) | 2004-06-08 |
| NO20034853D0 (no) | 2003-10-30 |
| EP1387867A1 (en) | 2004-02-11 |
| CN1244642C (zh) | 2006-03-08 |
| BRPI0209362B8 (pt) | 2015-12-22 |
| NO325737B1 (no) | 2008-07-14 |
| BR0209362B1 (pt) | 2013-11-12 |
| CA2444715C (en) | 2009-07-14 |
| WO2002090445A1 (en) | 2002-11-14 |
| DE60207237T2 (de) | 2006-07-06 |
| MXPA03010086A (es) | 2004-03-10 |
| US20040136933A1 (en) | 2004-07-15 |
| EP1387867B1 (en) | 2005-11-09 |
| JP4141845B2 (ja) | 2008-08-27 |
| RU2003133772A (ru) | 2005-05-10 |
| NO20034853L (no) | 2003-10-30 |
| CA2444715A1 (en) | 2002-11-14 |
| ZA200307622B (en) | 2004-04-21 |
| JP2004531609A (ja) | 2004-10-14 |
| CN1507476A (zh) | 2004-06-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PC1 | Assignment before grant (sect. 113) |
Owner name: CIBA SPECIALTY CHEMICALS HOLDING INC. Free format text: FORMER APPLICANT(S): CIBA SPECIALTY CHEMICALS WATER TREATMENTS LIMITED |
|
| FGA | Letters patent sealed or granted (standard patent) | ||
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |