WO2005087816A1 - Effektstoffe enthaltende wässrige polymerdispersionen, verfahren zu ihrer herstellung und ihre verwendung - Google Patents
Effektstoffe enthaltende wässrige polymerdispersionen, verfahren zu ihrer herstellung und ihre verwendung Download PDFInfo
- Publication number
- WO2005087816A1 WO2005087816A1 PCT/EP2005/002484 EP2005002484W WO2005087816A1 WO 2005087816 A1 WO2005087816 A1 WO 2005087816A1 EP 2005002484 W EP2005002484 W EP 2005002484W WO 2005087816 A1 WO2005087816 A1 WO 2005087816A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- polymer
- monomers
- polymerization
- aqueous
- effect substances
- Prior art date
Links
- 230000000694 effects Effects 0.000 title claims abstract description 89
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 15
- 239000004815 dispersion polymer Substances 0.000 title claims abstract description 12
- 239000000463 material Substances 0.000 title abstract 6
- 229920000642 polymer Polymers 0.000 claims abstract description 151
- 239000000178 monomer Substances 0.000 claims abstract description 123
- 239000002245 particle Substances 0.000 claims abstract description 96
- 239000006185 dispersion Substances 0.000 claims abstract description 61
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 38
- 239000000839 emulsion Substances 0.000 claims abstract description 37
- 239000000203 mixture Substances 0.000 claims abstract description 24
- 239000011159 matrix material Substances 0.000 claims abstract description 16
- 239000000843 powder Substances 0.000 claims abstract description 16
- 230000005855 radiation Effects 0.000 claims abstract description 13
- 239000000123 paper Substances 0.000 claims abstract description 12
- 239000002537 cosmetic Substances 0.000 claims abstract description 8
- 238000009472 formulation Methods 0.000 claims abstract description 6
- 239000003999 initiator Substances 0.000 claims abstract description 6
- 239000010985 leather Substances 0.000 claims abstract description 5
- 238000001704 evaporation Methods 0.000 claims abstract description 4
- 239000004753 textile Substances 0.000 claims abstract description 4
- 239000000126 substance Substances 0.000 claims description 87
- 238000006116 polymerization reaction Methods 0.000 claims description 54
- 239000006096 absorbing agent Substances 0.000 claims description 41
- -1 optical brighteners Substances 0.000 claims description 35
- 238000000034 method Methods 0.000 claims description 25
- 239000000975 dye Substances 0.000 claims description 22
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 17
- 239000003505 polymerization initiator Substances 0.000 claims description 16
- 230000008569 process Effects 0.000 claims description 15
- 239000004094 surface-active agent Substances 0.000 claims description 15
- 230000003287 optical effect Effects 0.000 claims description 14
- 239000003381 stabilizer Substances 0.000 claims description 14
- 239000004907 Macro-emulsion Substances 0.000 claims description 13
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims description 11
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 11
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 11
- JTHZUSWLNCPZLX-UHFFFAOYSA-N 6-fluoro-3-methyl-2h-indazole Chemical compound FC1=CC=C2C(C)=NNC2=C1 JTHZUSWLNCPZLX-UHFFFAOYSA-N 0.000 claims description 11
- MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 claims description 10
- JHWGFJBTMHEZME-UHFFFAOYSA-N 4-prop-2-enoyloxybutyl prop-2-enoate Chemical compound C=CC(=O)OCCCCOC(=O)C=C JHWGFJBTMHEZME-UHFFFAOYSA-N 0.000 claims description 10
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 10
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 10
- QUAMTGJKVDWJEQ-UHFFFAOYSA-N octabenzone Chemical compound OC1=CC(OCCCCCCCC)=CC=C1C(=O)C1=CC=CC=C1 QUAMTGJKVDWJEQ-UHFFFAOYSA-N 0.000 claims description 9
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 230000000087 stabilizing effect Effects 0.000 claims description 7
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 5
- 230000009471 action Effects 0.000 claims description 5
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 claims description 5
- PZDUWXKXFAIFOR-UHFFFAOYSA-N hexadecyl prop-2-enoate Chemical compound CCCCCCCCCCCCCCCCOC(=O)C=C PZDUWXKXFAIFOR-UHFFFAOYSA-N 0.000 claims description 5
- 230000002209 hydrophobic effect Effects 0.000 claims description 5
- 229920000620 organic polymer Polymers 0.000 claims description 5
- YAXXOCZAXKLLCV-UHFFFAOYSA-N 3-dodecyloxolane-2,5-dione Chemical class CCCCCCCCCCCCC1CC(=O)OC1=O YAXXOCZAXKLLCV-UHFFFAOYSA-N 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 239000003139 biocide Substances 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 230000001804 emulsifying effect Effects 0.000 claims description 4
- 239000003063 flame retardant Substances 0.000 claims description 4
- 239000004922 lacquer Substances 0.000 claims description 4
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 239000000470 constituent Substances 0.000 claims description 3
- 230000000977 initiatory effect Effects 0.000 claims description 3
- 150000002894 organic compounds Chemical class 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 239000007870 radical polymerization initiator Substances 0.000 claims description 3
- 239000008186 active pharmaceutical agent Substances 0.000 claims description 2
- 235000019728 animal nutrition Nutrition 0.000 claims description 2
- 239000003995 emulsifying agent Substances 0.000 claims description 2
- 238000009825 accumulation Methods 0.000 claims 1
- 238000004945 emulsification Methods 0.000 abstract description 5
- 239000002253 acid Substances 0.000 abstract description 3
- 150000007513 acids Chemical class 0.000 abstract description 2
- 239000011149 active material Substances 0.000 abstract 1
- 238000004220 aggregation Methods 0.000 abstract 1
- 230000002776 aggregation Effects 0.000 abstract 1
- 238000000576 coating method Methods 0.000 abstract 1
- 230000008020 evaporation Effects 0.000 abstract 1
- 239000003973 paint Substances 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 27
- 238000007720 emulsion polymerization reaction Methods 0.000 description 14
- 229920002472 Starch Polymers 0.000 description 13
- 235000019698 starch Nutrition 0.000 description 13
- 239000007864 aqueous solution Substances 0.000 description 11
- LCPVQAHEFVXVKT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)pyridin-3-amine Chemical compound NC1=CC=CN=C1OC1=CC=C(F)C=C1F LCPVQAHEFVXVKT-UHFFFAOYSA-N 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 10
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 10
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 8
- 238000006887 Ullmann reaction Methods 0.000 description 8
- 238000004513 sizing Methods 0.000 description 8
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 8
- 229920000881 Modified starch Polymers 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 235000019426 modified starch Nutrition 0.000 description 6
- 230000001681 protective effect Effects 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 5
- 239000000084 colloidal system Substances 0.000 description 5
- 239000003086 colorant Substances 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 230000000379 polymerizing effect Effects 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 239000008107 starch Substances 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 239000004698 Polyethylene Substances 0.000 description 4
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 4
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 4
- 229920000573 polyethylene Polymers 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 3
- 239000012964 benzotriazole Substances 0.000 description 3
- 230000005540 biological transmission Effects 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 230000015556 catabolic process Effects 0.000 description 3
- 239000003431 cross linking reagent Substances 0.000 description 3
- 238000006731 degradation reaction Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 230000001151 other effect Effects 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 239000004800 polyvinyl chloride Substances 0.000 description 3
- 229920000915 polyvinyl chloride Polymers 0.000 description 3
- 229940088594 vitamin Drugs 0.000 description 3
- 239000011782 vitamin Substances 0.000 description 3
- 229930003231 vitamin Natural products 0.000 description 3
- 235000013343 vitamin Nutrition 0.000 description 3
- OIQXFRANQVWXJF-QBFSEMIESA-N (2z)-2-benzylidene-4,7,7-trimethylbicyclo[2.2.1]heptan-3-one Chemical compound CC1(C)C2CCC1(C)C(=O)\C2=C/C1=CC=CC=C1 OIQXFRANQVWXJF-QBFSEMIESA-N 0.000 description 2
- 150000000183 1,3-benzoxazoles Chemical class 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- FMRHJJZUHUTGKE-UHFFFAOYSA-N Ethylhexyl salicylate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1O FMRHJJZUHUTGKE-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- YBGZDTIWKVFICR-JLHYYAGUSA-N Octyl 4-methoxycinnamic acid Chemical compound CCCCC(CC)COC(=O)\C=C\C1=CC=C(OC)C=C1 YBGZDTIWKVFICR-JLHYYAGUSA-N 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 description 2
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 2
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- BLFLLBZGZJTVJG-UHFFFAOYSA-N benzocaine Chemical compound CCOC(=O)C1=CC=C(N)C=C1 BLFLLBZGZJTVJG-UHFFFAOYSA-N 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 229960000541 cetyl alcohol Drugs 0.000 description 2
- WBYWAXJHAXSJNI-UHFFFAOYSA-N cinnamic acid Chemical class OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- NOPFSRXAKWQILS-UHFFFAOYSA-N docosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCO NOPFSRXAKWQILS-UHFFFAOYSA-N 0.000 description 2
- UVCJGUGAGLDPAA-UHFFFAOYSA-N ensulizole Chemical compound N1C2=CC(S(=O)(=O)O)=CC=C2N=C1C1=CC=CC=C1 UVCJGUGAGLDPAA-UHFFFAOYSA-N 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 2
- 150000004676 glycans Chemical class 0.000 description 2
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 2
- DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical compound CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 description 2
- 239000000976 ink Substances 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 230000000485 pigmenting effect Effects 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 229920001282 polysaccharide Polymers 0.000 description 2
- 239000005017 polysaccharide Substances 0.000 description 2
- 239000012266 salt solution Substances 0.000 description 2
- 239000012258 stirred mixture Substances 0.000 description 2
- 229920002994 synthetic fiber Polymers 0.000 description 2
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 2
- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical class OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 description 1
- FTLTTYGQIYQDEL-UHFFFAOYSA-N 1,1-bis(ethenyl)urea Chemical compound NC(=O)N(C=C)C=C FTLTTYGQIYQDEL-UHFFFAOYSA-N 0.000 description 1
- QLAJNZSPVITUCQ-UHFFFAOYSA-N 1,3,2-dioxathietane 2,2-dioxide Chemical compound O=S1(=O)OCO1 QLAJNZSPVITUCQ-UHFFFAOYSA-N 0.000 description 1
- NVZWEEGUWXZOKI-UHFFFAOYSA-N 1-ethenyl-2-methylbenzene Chemical compound CC1=CC=CC=C1C=C NVZWEEGUWXZOKI-UHFFFAOYSA-N 0.000 description 1
- OSSNTDFYBPYIEC-UHFFFAOYSA-N 1-ethenylimidazole Chemical compound C=CN1C=CN=C1 OSSNTDFYBPYIEC-UHFFFAOYSA-N 0.000 description 1
- NUTVORGGYDQIDD-UHFFFAOYSA-N 1-ethylsulfanylethanol Chemical compound CCSC(C)O NUTVORGGYDQIDD-UHFFFAOYSA-N 0.000 description 1
- LOXRGHGHQYWXJK-UHFFFAOYSA-N 1-octylsulfanyloctane Chemical compound CCCCCCCCSCCCCCCCC LOXRGHGHQYWXJK-UHFFFAOYSA-N 0.000 description 1
- QEDJMOONZLUIMC-UHFFFAOYSA-N 1-tert-butyl-4-ethenylbenzene Chemical compound CC(C)(C)C1=CC=C(C=C)C=C1 QEDJMOONZLUIMC-UHFFFAOYSA-N 0.000 description 1
- ONTODYXHFBKCDK-UHFFFAOYSA-N 2-(2,4-dimethylphenyl)-1,3,5-triazine Chemical compound CC1=CC(C)=CC=C1C1=NC=NC=N1 ONTODYXHFBKCDK-UHFFFAOYSA-N 0.000 description 1
- JLZIIHMTTRXXIN-UHFFFAOYSA-N 2-(2-hydroxy-4-methoxybenzoyl)benzoic acid Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1C(O)=O JLZIIHMTTRXXIN-UHFFFAOYSA-N 0.000 description 1
- AAJONXNFUGTELF-UHFFFAOYSA-N 2-(3,3-diphenylprop-2-enylidene)propanedioic acid Chemical compound C=1C=CC=CC=1C(=CC=C(C(=O)O)C(O)=O)C1=CC=CC=C1 AAJONXNFUGTELF-UHFFFAOYSA-N 0.000 description 1
- LEVFXWNQQSSNAC-UHFFFAOYSA-N 2-(4,6-diphenyl-1,3,5-triazin-2-yl)-5-hexoxyphenol Chemical compound OC1=CC(OCCCCCC)=CC=C1C1=NC(C=2C=CC=CC=2)=NC(C=2C=CC=CC=2)=N1 LEVFXWNQQSSNAC-UHFFFAOYSA-N 0.000 description 1
- UUINYPIVWRZHAG-UHFFFAOYSA-N 2-(4,6-diphenyl-1,3,5-triazin-2-yl)-5-methoxyphenol Chemical compound OC1=CC(OC)=CC=C1C1=NC(C=2C=CC=CC=2)=NC(C=2C=CC=CC=2)=N1 UUINYPIVWRZHAG-UHFFFAOYSA-N 0.000 description 1
- ZMWRRFHBXARRRT-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4,6-bis(2-methylbutan-2-yl)phenol Chemical compound CCC(C)(C)C1=CC(C(C)(C)CC)=CC(N2N=C3C=CC=CC3=N2)=C1O ZMWRRFHBXARRRT-UHFFFAOYSA-N 0.000 description 1
- OLFNXLXEGXRUOI-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4,6-bis(2-phenylpropan-2-yl)phenol Chemical compound C=1C(N2N=C3C=CC=CC3=N2)=C(O)C(C(C)(C)C=2C=CC=CC=2)=CC=1C(C)(C)C1=CC=CC=C1 OLFNXLXEGXRUOI-UHFFFAOYSA-N 0.000 description 1
- LHPPDQUVECZQSW-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4,6-ditert-butylphenol Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC(N2N=C3C=CC=CC3=N2)=C1O LHPPDQUVECZQSW-UHFFFAOYSA-N 0.000 description 1
- IYAZLDLPUNDVAG-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4-(2,4,4-trimethylpentan-2-yl)phenol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 IYAZLDLPUNDVAG-UHFFFAOYSA-N 0.000 description 1
- WXHVQMGINBSVAY-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 WXHVQMGINBSVAY-UHFFFAOYSA-N 0.000 description 1
- ITLDHFORLZTRJI-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-5-octoxyphenol Chemical compound OC1=CC(OCCCCCCCC)=CC=C1N1N=C2C=CC=CC2=N1 ITLDHFORLZTRJI-UHFFFAOYSA-N 0.000 description 1
- AEKIIPFWPLNQFY-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-6-[3-[[dimethyl(trimethylsilyloxy)silyl]oxy-dimethylsilyl]-2-methylpropyl]-4-methylphenol Chemical compound C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)CC(C)CC1=CC(C)=CC(N2N=C3C=CC=CC3=N2)=C1O AEKIIPFWPLNQFY-UHFFFAOYSA-N 0.000 description 1
- VQMHSKWEJGIXGA-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-6-dodecyl-4-methylphenol Chemical compound CCCCCCCCCCCCC1=CC(C)=CC(N2N=C3C=CC=CC3=N2)=C1O VQMHSKWEJGIXGA-UHFFFAOYSA-N 0.000 description 1
- FJGQBLRYBUAASW-UHFFFAOYSA-N 2-(benzotriazol-2-yl)phenol Chemical class OC1=CC=CC=C1N1N=C2C=CC=CC2=N1 FJGQBLRYBUAASW-UHFFFAOYSA-N 0.000 description 1
- DPBJAVGHACCNRL-UHFFFAOYSA-N 2-(dimethylamino)ethyl prop-2-enoate Chemical compound CN(C)CCOC(=O)C=C DPBJAVGHACCNRL-UHFFFAOYSA-N 0.000 description 1
- FESJNIGBEZWAIB-UHFFFAOYSA-N 2-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-5-(2-hydroxy-3-octoxypropoxy)phenol Chemical compound OC1=CC(OCC(O)COCCCCCCCC)=CC=C1C1=NC(C=2C(=CC(C)=CC=2)C)=NC(C=2C(=CC(C)=CC=2)C)=N1 FESJNIGBEZWAIB-UHFFFAOYSA-N 0.000 description 1
- BZQCIHBFVOTXRU-UHFFFAOYSA-N 2-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-5-(3-butoxy-2-hydroxypropoxy)phenol Chemical compound OC1=CC(OCC(O)COCCCC)=CC=C1C1=NC(C=2C(=CC(C)=CC=2)C)=NC(C=2C(=CC(C)=CC=2)C)=N1 BZQCIHBFVOTXRU-UHFFFAOYSA-N 0.000 description 1
- SITYOOWCYAYOKL-UHFFFAOYSA-N 2-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-5-(3-dodecoxy-2-hydroxypropoxy)phenol Chemical compound OC1=CC(OCC(O)COCCCCCCCCCCCC)=CC=C1C1=NC(C=2C(=CC(C)=CC=2)C)=NC(C=2C(=CC(C)=CC=2)C)=N1 SITYOOWCYAYOKL-UHFFFAOYSA-N 0.000 description 1
- ZSSVCEUEVMALRD-UHFFFAOYSA-N 2-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-5-(octyloxy)phenol Chemical compound OC1=CC(OCCCCCCCC)=CC=C1C1=NC(C=2C(=CC(C)=CC=2)C)=NC(C=2C(=CC(C)=CC=2)C)=N1 ZSSVCEUEVMALRD-UHFFFAOYSA-N 0.000 description 1
- DBYBHKQEHCYBQV-UHFFFAOYSA-N 2-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-5-dodecoxyphenol Chemical compound OC1=CC(OCCCCCCCCCCCC)=CC=C1C1=NC(C=2C(=CC(C)=CC=2)C)=NC(C=2C(=CC(C)=CC=2)C)=N1 DBYBHKQEHCYBQV-UHFFFAOYSA-N 0.000 description 1
- WPMUMRCRKFBYIH-UHFFFAOYSA-N 2-[4,6-bis(2-hydroxy-4-octoxyphenyl)-1,3,5-triazin-2-yl]-5-octoxyphenol Chemical compound OC1=CC(OCCCCCCCC)=CC=C1C1=NC(C=2C(=CC(OCCCCCCCC)=CC=2)O)=NC(C=2C(=CC(OCCCCCCCC)=CC=2)O)=N1 WPMUMRCRKFBYIH-UHFFFAOYSA-N 0.000 description 1
- NPUPWUDXQCOMBF-UHFFFAOYSA-N 2-[4,6-bis(4-methylphenyl)-1,3,5-triazin-2-yl]-5-octoxyphenol Chemical compound OC1=CC(OCCCCCCCC)=CC=C1C1=NC(C=2C=CC(C)=CC=2)=NC(C=2C=CC(C)=CC=2)=N1 NPUPWUDXQCOMBF-UHFFFAOYSA-N 0.000 description 1
- PIGBIZGGEUNVCV-UHFFFAOYSA-N 2-[4,6-bis[4-(3-butoxy-2-hydroxypropoxy)-2-hydroxyphenyl]-1,3,5-triazin-2-yl]-5-(3-butoxy-2-hydroxypropoxy)phenol Chemical compound OC1=CC(OCC(O)COCCCC)=CC=C1C1=NC(C=2C(=CC(OCC(O)COCCCC)=CC=2)O)=NC(C=2C(=CC(OCC(O)COCCCC)=CC=2)O)=N1 PIGBIZGGEUNVCV-UHFFFAOYSA-N 0.000 description 1
- HHIVRACNDKRDTF-UHFFFAOYSA-N 2-[4-(2,4-dimethylphenyl)-6-(2-hydroxy-4-propoxyphenyl)-1,3,5-triazin-2-yl]-5-propoxyphenol Chemical compound OC1=CC(OCCC)=CC=C1C1=NC(C=2C(=CC(C)=CC=2)C)=NC(C=2C(=CC(OCCC)=CC=2)O)=N1 HHIVRACNDKRDTF-UHFFFAOYSA-N 0.000 description 1
- VARDNKCBWBOEBW-UHFFFAOYSA-N 2-[4-(4-methoxyphenyl)-6-phenyl-1,3,5-triazin-2-yl]phenol Chemical compound C1=CC(OC)=CC=C1C1=NC(C=2C=CC=CC=2)=NC(C=2C(=CC=CC=2)O)=N1 VARDNKCBWBOEBW-UHFFFAOYSA-N 0.000 description 1
- LHHLLQVLJAUUDT-UHFFFAOYSA-N 2-ethylhexyl 3-[3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyphenyl]propanoate Chemical compound CC(C)(C)C1=CC(CCC(=O)OCC(CC)CCCC)=CC(N2N=C3C=CC=CC3=N2)=C1O LHHLLQVLJAUUDT-UHFFFAOYSA-N 0.000 description 1
- JGUMTYWKIBJSTN-UHFFFAOYSA-N 2-ethylhexyl 4-[[4,6-bis[4-(2-ethylhexoxycarbonyl)anilino]-1,3,5-triazin-2-yl]amino]benzoate Chemical compound C1=CC(C(=O)OCC(CC)CCCC)=CC=C1NC1=NC(NC=2C=CC(=CC=2)C(=O)OCC(CC)CCCC)=NC(NC=2C=CC(=CC=2)C(=O)OCC(CC)CCCC)=N1 JGUMTYWKIBJSTN-UHFFFAOYSA-N 0.000 description 1
- MAJRQODVOQXXQQ-UHFFFAOYSA-N 2-phenyl-1h-benzimidazole-4-sulfonic acid Chemical compound N1C=2C(S(=O)(=O)O)=CC=CC=2N=C1C1=CC=CC=C1 MAJRQODVOQXXQQ-UHFFFAOYSA-N 0.000 description 1
- AGBXYHCHUYARJY-UHFFFAOYSA-N 2-phenylethenesulfonic acid Chemical compound OS(=O)(=O)C=CC1=CC=CC=C1 AGBXYHCHUYARJY-UHFFFAOYSA-N 0.000 description 1
- UWERUIGPWOVNGG-MDZDMXLPSA-N 3-[(e)-dec-1-enyl]oxolane-2,5-dione Chemical compound CCCCCCCC\C=C\C1CC(=O)OC1=O UWERUIGPWOVNGG-MDZDMXLPSA-N 0.000 description 1
- WVRNUXJQQFPNMN-VAWYXSNFSA-N 3-[(e)-dodec-1-enyl]oxolane-2,5-dione Chemical compound CCCCCCCCCC\C=C\C1CC(=O)OC1=O WVRNUXJQQFPNMN-VAWYXSNFSA-N 0.000 description 1
- RSPWVGZWUBNLQU-FOCLMDBBSA-N 3-[(e)-hexadec-1-enyl]oxolane-2,5-dione Chemical compound CCCCCCCCCCCCCC\C=C\C1CC(=O)OC1=O RSPWVGZWUBNLQU-FOCLMDBBSA-N 0.000 description 1
- FXOMYJAPSPLGEI-UHFFFAOYSA-N 3-hexadec-8-enyloxolane-2,5-dione Chemical class CCCCCCCC=CCCCCCCCC1CC(=O)OC1=O FXOMYJAPSPLGEI-UHFFFAOYSA-N 0.000 description 1
- DKIDEFUBRARXTE-UHFFFAOYSA-N 3-mercaptopropanoic acid Chemical compound OC(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-N 0.000 description 1
- SHLSSLVZXJBVHE-UHFFFAOYSA-N 3-sulfanylpropan-1-ol Chemical compound OCCCS SHLSSLVZXJBVHE-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
- FROCQMFXPIROOK-UHFFFAOYSA-N 4-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]benzene-1,3-diol Chemical compound CC1=CC(C)=CC=C1C1=NC(C=2C(=CC(C)=CC=2)C)=NC(C=2C(=CC(O)=CC=2)O)=N1 FROCQMFXPIROOK-UHFFFAOYSA-N 0.000 description 1
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical class NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 1
- NEJMTSWXTZREOC-UHFFFAOYSA-N 4-sulfanylbutan-1-ol Chemical compound OCCCCS NEJMTSWXTZREOC-UHFFFAOYSA-N 0.000 description 1
- WDMFHQNUSVLQMS-UHFFFAOYSA-N 5-(3,3-dimethyl-2-bicyclo[2.2.1]heptanylidene)pent-3-en-2-one Chemical compound C1CC2C(C)(C)C(=CC=CC(=O)C)C1C2 WDMFHQNUSVLQMS-UHFFFAOYSA-N 0.000 description 1
- UWSMKYBKUPAEJQ-UHFFFAOYSA-N 5-Chloro-2-(3,5-di-tert-butyl-2-hydroxyphenyl)-2H-benzotriazole Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC(N2N=C3C=C(Cl)C=CC3=N2)=C1O UWSMKYBKUPAEJQ-UHFFFAOYSA-N 0.000 description 1
- YGUMVDWOQQJBGA-VAWYXSNFSA-N 5-[(4-anilino-6-morpholin-4-yl-1,3,5-triazin-2-yl)amino]-2-[(e)-2-[4-[(4-anilino-6-morpholin-4-yl-1,3,5-triazin-2-yl)amino]-2-sulfophenyl]ethenyl]benzenesulfonic acid Chemical compound C=1C=C(\C=C\C=2C(=CC(NC=3N=C(N=C(NC=4C=CC=CC=4)N=3)N3CCOCC3)=CC=2)S(O)(=O)=O)C(S(=O)(=O)O)=CC=1NC(N=C(N=1)N2CCOCC2)=NC=1NC1=CC=CC=C1 YGUMVDWOQQJBGA-VAWYXSNFSA-N 0.000 description 1
- KWSLGOVYXMQPPX-UHFFFAOYSA-N 5-[3-(trifluoromethyl)phenyl]-2h-tetrazole Chemical compound FC(F)(F)C1=CC=CC(C2=NNN=N2)=C1 KWSLGOVYXMQPPX-UHFFFAOYSA-N 0.000 description 1
- 229920005789 ACRONAL® acrylic binder Polymers 0.000 description 1
- 229920000945 Amylopectin Polymers 0.000 description 1
- 229920000856 Amylose Polymers 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- IEPRKVQEAMIZSS-UHFFFAOYSA-N Di-Et ester-Fumaric acid Natural products CCOC(=O)C=CC(=O)OCC IEPRKVQEAMIZSS-UHFFFAOYSA-N 0.000 description 1
- HTIRHQRTDBPHNZ-UHFFFAOYSA-N Dibutyl sulfide Chemical compound CCCCSCCCC HTIRHQRTDBPHNZ-UHFFFAOYSA-N 0.000 description 1
- IEPRKVQEAMIZSS-WAYWQWQTSA-N Diethyl maleate Chemical compound CCOC(=O)\C=C/C(=O)OCC IEPRKVQEAMIZSS-WAYWQWQTSA-N 0.000 description 1
- LZAZXBXPKRULLB-UHFFFAOYSA-N Diisopropyl disulfide Chemical compound CC(C)SSC(C)C LZAZXBXPKRULLB-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 239000004280 Sodium formate Substances 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- SEQDDYPDSLOBDC-UHFFFAOYSA-N Temazepam Chemical compound N=1C(O)C(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 SEQDDYPDSLOBDC-UHFFFAOYSA-N 0.000 description 1
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 1
- 239000012963 UV stabilizer Substances 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- UBNYRXMKIIGMKK-RMKNXTFCSA-N amiloxate Chemical compound COC1=CC=C(\C=C\C(=O)OCCC(C)C)C=C1 UBNYRXMKIIGMKK-RMKNXTFCSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229940051880 analgesics and antipyretics pyrazolones Drugs 0.000 description 1
- 150000001449 anionic compounds Chemical class 0.000 description 1
- 229920006320 anionic starch Polymers 0.000 description 1
- 230000002528 anti-freeze Effects 0.000 description 1
- XNEFYCZVKIDDMS-UHFFFAOYSA-N avobenzone Chemical compound C1=CC(OC)=CC=C1C(=O)CC(=O)C1=CC=C(C(C)(C)C)C=C1 XNEFYCZVKIDDMS-UHFFFAOYSA-N 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N benzo-alpha-pyrone Natural products C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 1
- 150000001565 benzotriazoles Chemical class 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- SODJJEXAWOSSON-UHFFFAOYSA-N bis(2-hydroxy-4-methoxyphenyl)methanone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=C(OC)C=C1O SODJJEXAWOSSON-UHFFFAOYSA-N 0.000 description 1
- FQUNFJULCYSSOP-UHFFFAOYSA-N bisoctrizole Chemical compound N1=C2C=CC=CC2=NN1C1=CC(C(C)(C)CC(C)(C)C)=CC(CC=2C(=C(C=C(C=2)C(C)(C)CC(C)(C)C)N2N=C3C=CC=CC3=N2)O)=C1O FQUNFJULCYSSOP-UHFFFAOYSA-N 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- OCWYEMOEOGEQAN-UHFFFAOYSA-N bumetrizole Chemical compound CC(C)(C)C1=CC(C)=CC(N2N=C3C=C(Cl)C=CC3=N2)=C1O OCWYEMOEOGEQAN-UHFFFAOYSA-N 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 1
- 229960000846 camphor Drugs 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000006103 coloring component Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 235000001671 coumarin Nutrition 0.000 description 1
- 125000000332 coumarinyl group Chemical class O1C(=O)C(=CC2=CC=CC=C12)* 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- NZZIMKJIVMHWJC-UHFFFAOYSA-N dibenzoylmethane Chemical class C=1C=CC=CC=1C(=O)CC(=O)C1=CC=CC=C1 NZZIMKJIVMHWJC-UHFFFAOYSA-N 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- FLISWPFVWWWNNP-BQYQJAHWSA-N dihydro-3-(1-octenyl)-2,5-furandione Chemical compound CCCCCC\C=C\C1CC(=O)OC1=O FLISWPFVWWWNNP-BQYQJAHWSA-N 0.000 description 1
- LDCRTTXIJACKKU-ARJAWSKDSA-N dimethyl maleate Chemical compound COC(=O)\C=C/C(=O)OC LDCRTTXIJACKKU-ARJAWSKDSA-N 0.000 description 1
- 235000019329 dioctyl sodium sulphosuccinate Nutrition 0.000 description 1
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 1
- YHAIUSTWZPMYGG-UHFFFAOYSA-L disodium;2,2-dioctyl-3-sulfobutanedioate Chemical compound [Na+].[Na+].CCCCCCCCC(C([O-])=O)(C(C([O-])=O)S(O)(=O)=O)CCCCCCCC YHAIUSTWZPMYGG-UHFFFAOYSA-L 0.000 description 1
- 229960000735 docosanol Drugs 0.000 description 1
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 1
- MCPKSFINULVDNX-UHFFFAOYSA-N drometrizole Chemical compound CC1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 MCPKSFINULVDNX-UHFFFAOYSA-N 0.000 description 1
- 238000000635 electron micrograph Methods 0.000 description 1
- GLVVKKSPKXTQRB-UHFFFAOYSA-N ethenyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OC=C GLVVKKSPKXTQRB-UHFFFAOYSA-N 0.000 description 1
- AFSIMBWBBOJPJG-UHFFFAOYSA-N ethenyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC=C AFSIMBWBBOJPJG-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- 229920001600 hydrophobic polymer Polymers 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- UJRDRFZCRQNLJM-UHFFFAOYSA-N methyl 3-[3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyphenyl]propanoate Chemical compound CC(C)(C)C1=CC(CCC(=O)OC)=CC(N2N=C3C=CC=CC3=N2)=C1O UJRDRFZCRQNLJM-UHFFFAOYSA-N 0.000 description 1
- 125000006178 methyl benzyl group Chemical group 0.000 description 1
- 239000011859 microparticle Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- PJUIMOJAAPLTRJ-UHFFFAOYSA-N monothioglycerol Chemical compound OCC(O)CS PJUIMOJAAPLTRJ-UHFFFAOYSA-N 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 description 1
- ZQXSMRAEXCEDJD-UHFFFAOYSA-N n-ethenylformamide Chemical compound C=CNC=O ZQXSMRAEXCEDJD-UHFFFAOYSA-N 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 239000002105 nanoparticle Substances 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 239000007764 o/w emulsion Substances 0.000 description 1
- XQAABEDPVQWFPN-UHFFFAOYSA-N octyl 3-[3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyphenyl]propanoate Chemical compound CC(C)(C)C1=CC(CCC(=O)OCCCCCCCC)=CC(N2N=C3C=CC=CC3=N2)=C1O XQAABEDPVQWFPN-UHFFFAOYSA-N 0.000 description 1
- DMFXLIFZVRXRRR-UHFFFAOYSA-N octyl 3-[3-tert-butyl-5-(5-chlorobenzotriazol-2-yl)-4-hydroxyphenyl]propanoate Chemical compound CC(C)(C)C1=CC(CCC(=O)OCCCCCCCC)=CC(N2N=C3C=C(Cl)C=CC3=N2)=C1O DMFXLIFZVRXRRR-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical compound [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 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
- 239000002304 perfume Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical class OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 description 1
- 239000004597 plastic additive Substances 0.000 description 1
- 229920000371 poly(diallyldimethylammonium chloride) polymer Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229940068886 polyethylene glycol 300 Drugs 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- QTECDUFMBMSHKR-UHFFFAOYSA-N prop-2-enyl prop-2-enoate Chemical compound C=CCOC(=O)C=C QTECDUFMBMSHKR-UHFFFAOYSA-N 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- KOUKXHPPRFNWPP-UHFFFAOYSA-N pyrazine-2,5-dicarboxylic acid;hydrate Chemical compound O.OC(=O)C1=CN=C(C(O)=O)C=N1 KOUKXHPPRFNWPP-UHFFFAOYSA-N 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 150000003902 salicylic acid esters Chemical class 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 1
- 235000019254 sodium formate Nutrition 0.000 description 1
- 229910001379 sodium hypophosphite Inorganic materials 0.000 description 1
- GGHPAKFFUZUEKL-UHFFFAOYSA-M sodium;hexadecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCCCOS([O-])(=O)=O GGHPAKFFUZUEKL-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000000527 sonication Methods 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229940012831 stearyl alcohol Drugs 0.000 description 1
- 150000001629 stilbenes Chemical class 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000000475 sunscreen effect Effects 0.000 description 1
- 239000000516 sunscreening agent Substances 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 239000004758 synthetic textile Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 1
- 229950006389 thiodiglycol Drugs 0.000 description 1
- NJRXVEJTAYWCQJ-UHFFFAOYSA-N thiomalic acid Chemical compound OC(=O)CC(S)C(O)=O NJRXVEJTAYWCQJ-UHFFFAOYSA-N 0.000 description 1
- LOIYMIARKYCTBW-OWOJBTEDSA-N trans-urocanic acid Chemical compound OC(=O)\C=C\C1=CNC=N1 LOIYMIARKYCTBW-OWOJBTEDSA-N 0.000 description 1
- LOIYMIARKYCTBW-UHFFFAOYSA-N trans-urocanic acid Natural products OC(=O)C=CC1=CNC=N1 LOIYMIARKYCTBW-UHFFFAOYSA-N 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- QGISLNJSJIGSLZ-UHFFFAOYSA-N trimethyl-[4-[(4,7,7-trimethyl-3-oxo-2-bicyclo[2.2.1]heptanylidene)methyl]phenyl]azanium Chemical compound CC1(C)C2CCC1(C)C(=O)C2=CC1=CC=C([N+](C)(C)C)C=C1 QGISLNJSJIGSLZ-UHFFFAOYSA-N 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- ZTWTYVWXUKTLCP-UHFFFAOYSA-N vinylphosphonic acid Chemical compound OP(O)(=O)C=C ZTWTYVWXUKTLCP-UHFFFAOYSA-N 0.000 description 1
- 239000013585 weight reducing agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/12—Polymerisation in non-solvents
- C08F2/16—Aqueous medium
- C08F2/22—Emulsion polymerisation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2312/00—Crosslinking
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2982—Particulate matter [e.g., sphere, flake, etc.]
- Y10T428/2991—Coated
- Y10T428/2998—Coated including synthetic resin or polymer
Definitions
- the invention relates to aqueous polymer dispersions containing effect substances, a process for the preparation of these aqueous polymer dispersions by mini-emulsion polymerization of ethylenically unsaturated monomers in the presence of effect substances and the use of polymers containing effect substances for stabilizing polymers against the action of UV radiation, oxygen and heat cosmetic and pharmaceutical formulations, in lacquer layers, in the manufacture of paper, leather and textiles and in formulations for animal nutrition.
- aqueous polymer dispersions which contain functional substances such as in particular UV absorbers or epoxy resins. They are prepared by dissolving the functional substances in an unsaturated monomer, emulsifying this solution in water in the presence of a surface-active agent to give a monomer emulsion with average particle sizes between 5 and 500 nm, and polymerizing the miniemulsion in the presence of a radical initiator.
- the aqueous dispersions which contain the functional substances such as UV absorbers, epoxy resins, acrylic-based polymers, phenolic resins, unsaturated polyesters, phenolic-based substances and petroleum resins, are used as binders and as additives for protective film.
- aqueous polymer dispersions the dispersed polymer particles of which contain an organic dye homogeneously, ie distributed in a molecular dispersion.
- aqueous dispersions are prepared by mini-emulsion polymerization by polymerizing ethylenically unsaturated monomers which contain an organic dye in solution in the form of an oil-in-water emulsion in the presence of radical-forming polymerization initiators, the disperse phase of the emulsion being essentially composed of dye containing monomer droplets with a diameter ⁇ 500 nm is formed.
- monomer mixtures which contain crosslinking monomers are used in the polymerization.
- the polymer dispersions are stable to sedimentation.
- the dispersed particles have an average particle diameter of 100 to 400 nm. They can be obtained from the aqueous dispersions using conventional drying methods.
- the dye-containing polymer dispersions are used, for example, for pigmenting high molecular weight organic and inorganic materials, for pigmenting printing inks and inks for ink-jet printing.
- EP-A-1 092416 the use of dyes, optical brighteners or UV absorbers containing finely divided, aqueous polymer dispersions or a powdery polymer obtainable therefrom, the polymer matrix of which contains dyes, optical brighteners or UV absorbers homogeneously distributed, as a coloring component in known cosmetic products.
- the dispersions are preferably prepared by the process known from WO-A-99/40123 by mini-emulsion polymerization of ethylenically unsaturated monomers which contain a dye, optical brightener or UV absorber in solution.
- colorant-containing polymer dispersions the colorant-containing polymer particles of which have an average particle diameter below 1000 nm, are known from EP-A-1 191 041.
- UV absorbers and optical brighteners can also be used as colorants.
- They are obtained by dissolving a colorant in at least one ethylenically unsaturated monomer, emulsifying this solution in water to form a conventional macroemulsion, homogenizing the macroemulsion to form a miniemulsion with an average droplet size below 1000 nm and polymerizing the miniemulsion in the presence of a radical-forming polymerization initiator, 0.1 to 20% by weight of at least one nonionic surface-active compound and 1 to 50% by weight, based in each case on the monomers used, of at least one amphiphilic polymer.
- the polymer particles contain 0.5 to 50% by weight, homogeneously distributed, of at least one organic dye, optical brightener or UV absorber, which is to be understood to mean that the organic colorants are monomolecularly dissolved in the polymer matrix or in the form of bi- or higher molecular weight Aggregates are present.
- WO-A-01/10936 discloses particles with a core / shell structure, in which the core comprises a polymer with a glass transition temperature T g of below 40 ° C. and a UV absorber and the shell preferably consists of a polymer made from methyl acrylate , Ethyl acrylate, ethyl methacrylate and / or methyl methacrylate.
- the polymer that forms the core of the particle can optionally be cross-linked.
- the polymer particles are made by emulsion polymerization.
- the polymer particles containing UV absorbers are used to produce UV-absorbing polymer compositions.
- Aqueous polymer dispersions containing alkyldiketenes are known from the older DE application 10248 879.7, which can be obtained by miniemulsion polymerization of hydrophobic monoethylenically unsaturated monomers in the presence of alkyldiketenes. These dispersions are used as sizing agents for paper, as water repellents for leather, natural and / or synthetic fibers and textiles.
- the older DE application 102 54 548.0 discloses the use of finely divided polymer powders containing at least one UV absorber for stabilizing polymers against the action of UV radiation.
- the polymer particles of the polymer powders have a particle size of 500 nm or less.
- the polymer particles contain 0.5 to 50% by weight of at least one UV absorber, which is either homogeneously distributed therein in molecular or nanocrystalline form or is completely or only partially enveloped by the polymer matrix.
- US Pat. No. 6,309,787 discloses a process for encapsulating dyes by mini-emulsion polymerization, the mini-emulsion being prepared in the presence of a surface-active agent, a co-surfactant and a nonionic surface-active agent. After the polymerization, dispersed particles are obtained which are composed of a dye core and a polymer shell.
- DE-A-196 28 143 discloses a process for the preparation of an aqueous polymer dispersion.
- the monomers are polymerized in the manner of a free-radical aqueous miniemulsion polymerization, in which at least part of the aqueous monomer miniemulsion is fed continuously to the polymerization zone with continuous polymerization.
- the object of the present invention is to provide aqueous polymer dispersions containing further effect substances.
- the object is achieved according to the invention with aqueous polymer dispersions containing effect substances with an average particle diameter of the dispersed particles of ⁇ 500 nm, the polymer particles containing as core a polymer matrix composed of at least one ethylenically unsaturated monomer, on the surface of which an effect substance is at least partially arranged is soluble in the monomers that form the polymer matrix of the particles.
- the effect substances are preferably arranged as a shell around the core of the polymer particles.
- the invention also relates to a process for the preparation of finely divided aqueous polymer dispersions containing effect substances with an average particle diameter of the dispersed polymer particles of ⁇ 500 nm by miniemulsion polymerization of ethylenically unsaturated monomers, if by emulsifying ethylenically unsaturated monomers in water in the presence of at least one Effect substance and a surfactant produces a mini emulsion with an average particle size of the emulsified particles of ⁇ 500 nm, and so polymerizes in the presence of at least one radical polymerization initiator, that initially only polymerize a maximum of 50% of the monomers that are in the polymerization zone and the effect substances migrate to the surface of the emulsified particles, and the polymerization only after the effect substances have largely or completely accumulated on the surface of the resulting polymer particles.
- effect substances are to be understood as products which are selected, for example, from the group of UV absorbers, organic dyes, optical brighteners, stabilizers and auxiliaries for organic polymers, IR dyes, flame retardants, alkenylsuccinic anhydrides, active pharmaceutical ingredients and biocides.
- the effect substances in question are soluble in the ethylenically unsaturated monomers which form the core of the polymer particles of the aqueous dispersion.
- the solubility of the effect substances in the monomers is at a temperature of 20 ° C. and a pressure of 1 bar, for example at least 1 g / l, preferably at least 10 g / l.
- the amount of the effect substances which is arranged on the surface of the dispersed polymer particles is, for example, 0.5 to 50% by weight, preferably 2 to 20% by weight, based on the polymer matrix.
- the mini-emulsion polymerization of ethylenically unsaturated monomers in the presence of oil-soluble dyes is known, for example, from WO-A-99/40123 cited in the prior art. Because of the details of this polymerization method, particular reference is made to page 3, line 30 to page 38, line 6 and to page 69, line 11 to page 84, line 43 of WO-A-99/40123. This part of the WO application is hereby made by reference to the disclosure content of the present invention.
- the ethylenically unsaturated monomers, non-polymerizable organic dyes, auxiliaries and process measures for producing the miniemulsion described there are used in the same way in the process according to the invention.
- the essential difference from the known process consists in the special implementation of the polymerization.
- other effect substances which are also soluble in ethylenically unsaturated monomers can be used in the process according to the invention.
- UV absorbers which are also oil-soluble and are preferably dissolved in the monoethylenically unsaturated monomers from which the core of the polymers is essentially formed, are particularly preferably used as effect substances.
- UV absorbers are commercial products. For example, they are sold under the trademark Uvinul® by BASF Aktiengesellschaft, Ludwigshafen. As is known, UV absorbers are understood to mean compounds which absorb UV rays and deactivate the absorbed radiation without radiation.
- UV absorbers absorb light of the wavelength ⁇ 400 nm and convert it into heat radiation. Such compounds are used, for example, in sunscreens and for stabilizing organic polymers.
- UV absorbers are derivatives of p-aminobenzoic acid, in particular their esters, for example ethyl 4-aminobenzoate and ethyl ethoxylated 4-aminobenzoate, salicylates, substituted cinnamates (cinnamates) such as octyl-p-methoxycinnamate and 4-isopentyl-4-methoxycinnam , 2-phenylbenzimidazole-5-sulfonic acid and its salts.
- a particularly preferred UV absorber is 4-n-octyloxy-2-hydroxy-benzophenone.
- Other examples of UV absorbers are:
- substituted acrylates e.g. Ethyl or isooctyl- ⁇ -cyano-y-.
- _-Diphenyl acrylate (mainly 2-ethylhexyl- ⁇ -cyano-jf, -diphenyl acrylate), methyl ⁇ -methoxycarbonyl - ⁇ - phenyl acrylate, methyl ⁇ -methoxycarbonyl- 0- (p-methoxyphenyl) acrylate, methyl or butyl- ⁇ -cyano-j-Nmethyl-? - (p-methoxyphenyl) acrylate, NG -?
- 2-hydroxybenzophenone derivatives e.g. 4-hydroxy, 4-methoxy, 4-octyloxy, 4-decyloxy, 4-dodecyloxy, 4-benzyloxy, 4,2 ', 4'-trihydroxy, 2'-hydroxy-4,4' di-methoxy-2-hydroxybenzophenone and 4-methoxy-2-hydroxybenzophenone sulfonic acid sodium salt;
- Esters of 4,4-diphenylbutadiene-1,1-dicarboxylic acid e.g. the bis (2-ethylhexyl) ester;
- Benzylidene camphor and its derivatives, such as z. B. are mentioned in DE-A 3836 630, e.g. 3-benzylidene camphor, 3 (4'-methylbenzylidene) d-1-camphor;
- Dibenzoylmethanes e.g. 4-tert-butyl-4'-methoxydibenzoylmethane
- 2,4,6-triaryltriazine compounds such as 2,4,6-tris- ⁇ N- [4- (2-ethylhex-1-yl) oxycarbonylphenyl] amino ⁇ -1, 3,5-triazine, 4,4 ' - ((6- (((tert-Butyl) aminocarbonyl) phenylamino) -1, 3,5-triazine-2,4-diyl) imino) bis (2'-ethylhexyl benzoate); and
- 2- (2-hydroxyphenyl) -1,3,5-thazines such as 2,4,6-tris (2-hydroxy-4-octyloxyphenyl) 1,3,5-triazine, 2- (2-hydroxy-4 -octyloxyphenyl) -4,6-bis (2,4-dimethylphenyl) -1, 3,5-triazine, 2- (2,4-dihydroxyphenyl) -4,6-bis (2,4-dimethylphenyl) - 1, 3,5-triazine, 2,4-bis (2-hydroxy-4-propyloxyphenyl) -6- (2,4-dimethylphenyl) -1, 3,5-triazine, 2- (2-hydroxy-4-octyloxyphenyl ) -4,6-bis (4-methylphenyl) - 1,3,5-triazine, 2- (2-hydroxy-4-dodecyloxyphenyl) -4,6-bis (2,4-dimethylphenyl) -1,3, 5-tri
- UV absorbers can be found in Cosmetic Legislation, Vol. 1, Cosmetic Products, European Commission 1999, pp. 64-66, to which reference is hereby made.
- Suitable UV absorbers are also described in lines 14 to 30 on page 6 of EP-A-1 191 041.
- organic dyes and optical brighteners which each dissolve in ethylenically unsaturated monomers and which are themselves not polymerizable. Such dyes and optical brighteners are described in detail in WO-A-99/40123, page 10, line 14 to page 25, line 25, which are referred to in the prior art and to which reference is once again expressly made here. While organic dyes have an absorption maximum in the wavelength range from 400 to 850 nm, optical brighteners have one or more absorption maxima in the range from 250 to 400 nm. As is known, optical brighteners emit fluorescent radiation in the visible range when irradiated with UV light.
- optical brighteners examples are compounds from the classes of bisstyrylbenzenes, stilbenes, benzoxazoles, coumarins, pyrenes and naphthalenes.
- Commercial optical brighteners are sold under the brands Tinopal® (Ciba), Ultraphor® (BASF Aktiengesellschaft) and Blankophor® (Bayer).
- Optical brighteners are also described in Römpp, 10th edition, volume 4, 3028-3029 (1998) and in Ullmanns, Encyclopedia of Industrial Chemistry, vol. 24, 363-386 (2003).
- Stabilizers for organic polymers are also suitable as effect substances. These are compounds that stabilize polymers against degradation when exposed to oxygen, light or heat. Such stabilizers are also referred to as antioxidants or as UV and light stabilizers, cf. Ullmanns, Encyclopadia of Industrial Chemistry, Vol. 3, 629-650 (ISBN-3-527-30385-5) and EP-A-1 110 999, page 2, line 29 to page 38, line 29. With such stabilizers practically all organic polymers are stabilized, cf. EP-A-1 110 999, page 38, line 30 to page 41, line 35. This reference is also by the
- the stabilizers described in the EP application belong to the class of compounds of pyrazolones, organic phosphites or phosphonites, sterically hindered phenols and sterically hindered amines (stabilizers of the so-called HALS type, cf. Römpp, 10th edition, volume 5, Pages 4206-4207
- Commercial stabilizers and Aids are sold under the Tinuvin® and Cyasorb® brands from Ciba and Tenox® brands from Eastman Kodak.
- Stabilizers and auxiliaries are described, for example, in Plastic Additives Handbook, 5th edition, Hanser, ISBN 1-56990-295-X.
- the stabilizers and auxiliaries are soluble in ethylenically unsaturated monomers, with at least 1 g / l, preferably at least 10 g / l, dissolving at a temperature of 20 ° C. and a pressure of 1 bar.
- IR dyes which are sold, for example, by BASF Aktiengesellschaft as Lumogen® IR
- flame retardants for example in Römpp, 10th edition, pages 1352 and 1353 and in Ullmanns, Encyclopedia of Industrial Chemistry, Vol. 14, 53-71.
- the flame retardants in question are soluble in ethylenically unsaturated monomers.
- Effect substances are also to be understood as meaning alkenylsuccinic anhydrides which are known, for example, as mass sizing agents for paper and are used industrially on a large scale.
- sizing agents are the isomers 4-, 5-, 6-, 7- and 8-hexadecenyl succinic anhydrides, decenyl succinic anhydride, octenyl succinic anhydride, dodecenyl succinic anhydride and n-hexadecenyl succinic anhydride, cf. also C.E. Farley and R.B. Wasser, The Sizing of Paper, Second Edition, (3), Sizing With Alkenyl Succinic Anhydride, TAPPI PRESS, 1989, ISBN 0-89852-051-7.
- compositions which are soluble in ethylenically unsaturated monomers can be used as effect substances.
- An overview of pharmaceutical active substances can be found, for example, in Römpp, 10th edition, volume 4, page 3235 (ISBN-3- 13-734910-9) and in Ullmanns, Encyclopedia of Industrial Chemistry, Vol. 25, 549 - 579 (2003 ).
- pharmaceutical active ingredients are also to be understood as vitamins. Vitamins are soluble in ethylenically unsaturated monomers. A summary of vitamins can be found, for example, in Römpp, 10th edition, volume 6, pages 4877-4887 (1999) and in Ullmanns, Encyclopedia of Industrial Chemistry, Vol. 38, 109-294.
- the core of the dispersed particles is essentially made of a polymer
- the water solubility of the monomers relates in each case to the solubility of the monomers in water at a temperature of 25 ° C. and a pressure of 1 bar.
- the dispersed polymer particles contain
- the monomers (a) also include those monomers A ' which have an increased solubility in water, ie> 60 g / l at 25 ° C. and 1 bar.
- the monomers A ' are used to modify the polymers and are usually involved in the structure of the polymer matrix in amounts of 0.1 to 20% by weight, preferably 0.5 to 10% by weight.
- these monomers are acrylic acid, methacrylic acid, styrenesulfonic acid, 2-acrylic-2-methylpropanesulfonic acid and vinylphosphonic acid and also cationic monomers such as dimethylaminoethyl acrylate or 1-vinylimidazole and N-vinylformamide and N-vinylpyrrolidone.
- the basic monomers are used in the form of the free bases, as a salt or in quaternized form in the polymerization.
- the monomers containing acid groups can be used in the polymerization in the form of the free acids or in a form partially or completely neutralized with alkali metal bases or ammonium bases.
- Suitable monomers of group (b) are, for example, 2- and 4-methylstyrene, p-tert-butylstyrene, esters of ethylenically unsaturated C 3 to C 5 carboxylic acids and alcohols with more than 12 C atoms in the molecule, vinyl laurate, Vinyl stearate and macromonomers such as oligopropene acrylate.
- Examples of monomers of group (c) are glycol diacrylate, trimethylolpropane triacrylate, pentaerythritol triacrylate, pentaerythritol tetraacrylate, butanediol diacrylate, allyl acrylate, di-vinylbenzene, divinyl urea and methylenebisacrylamide.
- the polymer matrix of the dispersed polymer particles can be made from a polymer
- the polymer matrix of the particles dispersed in water preferably consists of a copolymer which is obtained by polymerizing
- the aqueous polymer dispersions according to the invention contain dispersed particles with an average particle diameter ⁇ 500 nm, preferably 50 to 400 nm.
- the polymer particles essentially consist of a polymer core, on the surface of which at least one effect substance is arranged. Ideally, the effect fabric forms a shell around the polymer core.
- FIG. 1 It is an electron micrograph of a section of a powder sample obtained from an aqueous polymer dispersion by distilling off the water.
- the effect substances are practically incompatible with the polymer or insoluble in the polymer which forms the core of the dispersed particle. They can therefore be found on or on the surface of the polymer matrix as a nanoscale shell.
- Aqueous polymer dispersions whose dispersed polymer particles consist of a polymer are particularly preferred
- UV absorber in particular 4-n-octyloxy-2-hydroxy-benzophenone.
- the monomers are used in the polymerization, for example, in amounts such that the resulting polymers
- (b) contain 0.5 to 50% by weight, preferably 1 to 20% by weight, of at least one monomer B in copolymerized form.
- the polymer matrix which forms the core of the dispersed particles preferably contains a monomer (c) copolymerized in an amount of 0.1 to 30% by weight, in particular 0.5 to 20, usually 1 to 10% by weight.
- the aqueous polymer dispersions according to the invention containing effect substances and having an average particle diameter of the dispersed polymer particles of ⁇ 500 nm are prepared by mini-emulsion polymerization of ethylenically unsaturated monomers.
- mini-emulsion polymerization of ethylenically unsaturated monomers For example, by first dissolving at least one effect substance in at least one monomer.
- the effect substances are in most cases monomolecularly dissolved, but can also be present in a colloidally dispersed form.
- the monomer solutions containing the effect substances are then emulsified in water in the presence of at least one surface-active agent.
- microparticles or nanoparticles which are insoluble in water and / or the monomers can also be used as stabilizers for the emulsion (Pickering effect).
- Stabilizers of this type are, for example, nanoscale silicon dioxide, aluminum oxide and magnesium sulfate. A miniemulsion with an average particle size of the emulsified droplets of ⁇ 500 nm is obtained. The emulsification is carried out by methods which are described in detail in WO-A-99/40123, page 26, line 11 to page 32, line 4.
- high-pressure homogenizers of various types are used for emulsification, or ultrasound is applied to a macroemulsion which contains at least one effect substance, which is dissolved in at least one monomer, and water as essential constituents.
- the mixture is emulsified in the presence of a surfactant.
- they are preferably first dissolved in at least one monomer and emulsified in water in dissolved or colloidally dispersed form.
- the aqueous phase which is used to prepare the mini-emulsions consists of water and optionally contains a surface-active agent which stabilizes the finely divided monomer droplets formed in the emulsion of the organic phase in the aqueous phase.
- the surface-active agent is used, for example, in amounts of up to 15% by weight, for example from 0.05 to 15% by weight, preferably 0.05 to 5 and in particular 0.1 to 2% by weight, based on the entire dispersion. It is found either in the aqueous phase, the organic phase or in both phases. It is preferably added to the aqueous phase before emulsification. In principle, all surfactants can be used.
- Surface-active agents used with preference are anionic compounds.
- Suitable surface-active agents are sodium lauryl sulfate, sodium dodecyl sulfate, sodium hexadecyl sulfate, sodium dioctyl sulfosuccinate and / or addition products of 15 to 50 moles of ethylene oxide with 1 mole of a C 12 to C 22 alcohol.
- At least one non-polymerizable hydrophobic compound for example a hydrocarbon, an alcohol having 10 to 24 carbon atoms, hydrophobic polymers with molecular weights M w of ⁇ 50,000, preferably ⁇ 10,000, are used in the preparation of these emulsions , Tetraalkylsilanes and / or mixtures of the compounds mentioned.
- Such stabilizers are hexadecane, decahydronaphthalene, olive oil, polystyrene with an average molecular weight M w ⁇ 50,000, preferably from 500 to 5000, siloxanes with a molecular weight Mw from 500 to 5000, poly-n-butyl acrylate such as Acronal® A 150 F, Cetyl alcohol, stearyl alcohol, palmityl alcohol and / or behenyl alcohol.
- the hydrophobic, non-polymerizable compounds are used optionally. They have a water solubility of ⁇ 0.1 g / l at 25 ° C and 1 bar. If they are used, they are used in amounts of, for example, 1 to 20, usually 1 to 10 and preferably 2 to 6% by weight, based on the monomers used in the polymerization.
- the polymerization can optionally also be carried out in the presence of protective colloids.
- protective colloids are polyvinyl alcohols, cellulose derivatives such as carboxymethyl cellulose, polyvinyl pyrrolidone, polyethylene glycols, graft polymers of vinyl acetate and / or vinyl propionate on polyethylene glycols, on one or both sides with alkyl , Carboxyl or amino groups end-capped polyethylene glycol le, polydiallyldimethylammonium chlorides and / or polysaccharides such as, in particular, water-soluble starches, starch derivatives and proteins.
- starch all types are suitable, e.g. both amylose and amylopectin, native starches, hydrophobically or hydrophilically modified starches, anionic starches, cationically modified starches, degraded starches, the starch degradation being able to be carried out, for example, oxidatively, thermally, hydrolytically or enzymatically, and for the starch degradation being both native and modified starches can be used.
- suitable protective colloids are dextrins and cross-linked water-soluble starches that are water-swellable.
- Anionically modified starches which have been subjected to a reduction in molecular weight are particularly preferred.
- the molecular weight reduction is preferably carried out enzymatically.
- the average molar mass M w of the degraded starches is, for example, 500 to 100,000, preferably 1000 to 30,000.
- the degraded starches have, for example, an intrinsic viscosity [ ⁇ ] of 0.04 to 0.5 dl / g.
- Such starches are described, for example, in EP-B-0257412 and in EP-B-0276770. If protective colloids are used in the polymerization, the amounts used are, for example, 0.5 to 15, in particular 1 to 10,% by weight, based on the monomers used in the polymerization.
- the polymerization can optionally be carried out in the presence of at least one polymerization regulator.
- polymerization regulators are organic compounds which contain sulfur in bound form, such as dodecyl mercaptan, thiodiglycol, ethylthioethanol, di-n-butyl sulfide, di-n-octyl sulfide, diphenyl sulfide, diisopropyl disulfide, 2-mercaptoethanol, 1, 3-mercaptopropanol, 3-mercaptopropane 1, 2-diol, 1, 4-mercaptobutanol, thioglycolic acid, 3-mercaptopropionic acid, mercaptosuccinic acid, thioacetic acid and thiourea, aldehydes such as formaldehyde, acetaldehyde and propionaldehyde, organic acids such as formic acid, sodium formate or ammonium formoprop
- a regulator is used in the polymerization, the one used in each case is Amount, for example 0.01 to 5, preferably 0.1 to 1 wt .-%, based on the monomers used in the polymerization.
- Polymerization regulators and crosslinkers can be used together in the polymerization.
- the mini emulsion is polymerized in the presence of at least one radical polymerization initiator. All compounds which can trigger a polymerization are suitable as the polymerization initiator. Essentially, these are peroxides, hydroperoxides, azo compounds and redox catalysts. Examples of initiators can be found in WO-A-99/40123, page 32, line 45 to page 34, line 9.
- the polymerization can also be triggered by exposure to high-energy radiation such as UV radiation.
- the polymerization temperature is, for example, 0 to 120 ° C., it being carried out at temperatures above 100 ° C. under increased pressure in pressure-tight apparatus.
- the mini emulsion is usually polymerized in the temperature range from 0 to 95 ° C.
- the polymerization is carried out according to the invention in such a way that initially only a maximum of 50% of the monomers which are in the polymerization zone polymerize.
- the effect substances migrate to the surface of the emulsified particles. There is probably an incompatibility between the effect substances and the developing polymer, or the effect substances are not soluble in the resulting polymer or the mixture of monomer, oligomers and polymers.
- the polymerization is only completed after the effect substances have largely or completely accumulated on the surface of the polymer particles formed. With the help of sampling during the polymerization, the separation of the effect substance and the polymer being formed can be followed.
- the effect substances essentially remain on the surface of the polymer particle, but, depending on the polymerization conditions, can also partially enter the aqueous phase, form domains in the polymer particle or otherwise accumulate in the polymer.
- a miniemulsion containing at least one effect substance is preferably first prepared
- crosslinking agent As a template during the polymerization or dose it batchwise or continuously as an emulsion feed. If at least two crosslinking agents are used, these can be metered in either as a mixture or separately from one another synchronously or with a time delay.
- the portion of the miniemulsion is then heated to the polymerization temperature and a sufficient amount of polymerization initiator is added to add up to a maximum of 50% of the submitted monomers polymerize, then metered an aqueous macroemulsion of at least one ethylenically unsaturated monomer C with at least two double bonds in the molecule and, after the effect substances have largely accumulated on the surface of the resulting polymer particles, the polymerization is completed by further addition of at least one polymerization initiator.
- the miniemulsion containing at least one effect substance is preferably introduced in an amount of at most 30% by weight together with an amount of polymerization initiator which is sufficient to polymerize 5 to 25% of the monomers initially introduced.
- An embodiment is particularly preferred in which the miniemulsion containing at least one effect substance is introduced in an amount of at most 25% by weight together with an amount of polymerization initiator which is sufficient to polymerize at most 15% of the monomers introduced.
- a mixture of a miniemulsion of monomers (a) and (b) and a polymerization initiator which is sufficient for the initiation of a maximum of 25% of the monomers presented, is added to a mixture of a miniemulsion of monomers (a) and (b) and at least one effect substance and heated to the polymerization temperature , the remaining portions of this miniemulsion and an aqueous mixture of a monomer (c) and metered in after the consumption of the added initiator by polymerization further polymerization initiator for the polymerization of the remaining monomers.
- the preferred monomers are those of the group
- Aqueous polymer dispersions containing effect substances are obtained in which the effect substances are arranged on the surface of the dispersed polymer particles.
- the solids concentration of these aqueous dispersions is, for example, 10 to 60, preferably 20 to 45,% by weight.
- Polymer powders containing effect substances can be obtained from such aqueous dispersions by evaporating the volatile constituents of a polymer dispersion containing aqueous effect substances.
- the aqueous dispersions containing effect substances are preferably subjected to spray drying.
- the dispersions according to the invention and the polymer powders obtained therefrom have the advantage that they contain the effect substances on their surface.
- the effect substances are therefore in a modification which is particularly advantageous for their application. This fact applies in particular to those polymer powders which have a UV absorber, preferably 4-n-octyloxy-2-hydroxybenzophenone, on their surface.
- aqueous polymer dispersions described above which contain effect substances on the surface of dispersed polymer particles, are used, for example, to stabilize polymers against the action of UV radiation, oxygen and heat, in cosmetic and pharmaceutical formulations, in lacquer layers, in the production of paper and leather and textiles and used in formulations for animal feeding.
- customary additives such as defoamers, thickeners, biocides, buffers, antifreezes, fats and / or oils can be added to the dispersions according to the invention.
- the application of the dispersions according to the invention is essentially determined by the effect substances contained in the dispersions.
- aqueous dispersions containing UV absorbers or the powders obtained therefrom are used in cosmetic formulations or for stabilizing polymers, in particular films made of polymers such as polyethylene, polypropylene, polyvinyl chloride, polycarbonate, polyamide or polyester, against the action of UV radiation .
- the stabilization of films against the influence of UV radiation is particularly important for those films which are used for greenhouses.
- the Products according to the invention which contain a UV absorber can also be used to stabilize moldings of any shape made from at least one of the abovementioned polymers, in particular polyethylene, polypropylene, acrylonitrile-butadiene-styrene polymers (ABS) and PVC.
- a concrete example is the use of the products according to the invention for stabilizing PVC profiles for window frames.
- Aqueous dispersions containing UV absorbers or the polymer powders obtained therefrom can also be used together with other dispersions according to the invention, which contain, for example, stabilizers for polymers such as antioxidants, for stabilizing polymers and lacquer layers.
- Aqueous polymer dispersions containing alkenylsuccinic anhydrides which are obtainable according to the invention, are added to the paper stock as pulp sizing agents in the production of paper.
- the percentages in the examples mean percent by weight.
- the droplet size of the mini emulsion and the average particle size of the aqueous polymer dispersions prepared by mini emulsion polymerization were determined using a Coulter N4 Plus Particle Analyzer on 0.01% by weight samples of the emulsion.
- the mean particle size of the dispersed polymer particles was determined using a Coulter LS 230 on 0.01% by weight samples of the aqueous dispersions.
- This solution was then introduced into an aqueous solution of 3.5 g of an aqueous Steinapol NLS solution (15% strength) in 435.8 g of water with stirring.
- a macroemulsion was obtained, which was then brought to a droplet size of approximately 200 nm by passing three times through an APV-Gaulin high-pressure homogenizer.
- the mini emulsion thus produced was stable on storage.
- 161.5 g (24% of the total amount) of the miniemulsion described above were placed in a reactor and heated to 80 ° C.
- 0.7 g of a 1% strength aqueous solution of Dissolvine E-Fe13 (iron / salt solution) and 9.35 g of a 2% strength aqueous sodium persulfate solution were then metered in at 80.degree.
- 511.6 g (76% of the total amount) of the mini-emulsion were metered in, and at the same time 112.2 g of a 2% strength aqueous sodium persulfate solution were added in a separate feed within 60 minutes.
- an emulsion polymerization was carried out by making a macroemulsion which was stirred and consisting of 58.5 g of methyl methacrylate, 2.3 g of pentaerythritol tetraacrylate and 1.2 g of a 15% strength aqueous sodium lauryl sulfate solution in 30.4 g desalted water was composed, metered into the dispersion obtained by mini-emulsion polymerization within 60 minutes.
- UV absorber monomer solution 46 Preparation of the UV absorber monomer solution 46.8 g of the powdery UV absorber 4 were added to a mixture of 156.7 g of methyl methacrylate, 11.7 g of stearyl acrylate, 7 g of acrylic acid and 11.7 g of butanediol 1,4-diacrylate - n-Octyloxy-2-hydroxy-benzophenone dissolved at room temperature within 15 minutes. Production of the mini emulsion
- 161.5 g (24% of the total amount) of the mini-emulsion were placed in a reactor and heated to 80.degree. At 80 ° C 0.7 g of a 1% aqueous solution of Dissolvine E-Fe13 (iron II salt solution) and 9.35 g of a 2% aqueous solution of sodium persulfate were added all at once. Then the remaining portion of the mini emulsion of 511.6 g (76% of the total amount) was metered in and, simultaneously, 112.2 g of a 2% aqueous sodium persulfate solution were added in a separate feed, each within 60 minutes.
- 80 ° C 0.7 g of a 1% aqueous solution of Dissolvine E-Fe13 (iron II salt solution) and 9.35 g of a 2% aqueous solution of sodium persulfate were added all at once. Then the remaining portion of the mini emulsion of 511.6 g (76% of the total amount) was metered in and, simultaneously, 11
- a stirred macroemulsion consisting of 58.5 g of methyl methacrylate, 2.3 g of divinylbenzene and 1.2 g of a 15% strength aqueous sodium lauryl sulfate solution in 30 was added to the aqueous dispersion heated to 80.degree , 4 g of completely demineralized water within 60 minutes.
- Postpolymerization 112.2 g of a 2% aqueous sodium persulfate solution were then added to the reaction mixture described above within 60 minutes.
- the reaction mixture was then stirred for a further 60 minutes at 80 ° C., then allowed to cool to 25 ° C. and filtered through a 500 ⁇ m and a 125 ⁇ m mesh screen in order to remove the coagulum (7 g).
- An aqueous polymer dispersion with an average particle diameter of the polymer particles of 64 nm was obtained.
- the UV absorber enveloped the polymer particles.
- This solution was then added to an aqueous solution of 4.8 g of a 15% aqueous sodium lauryl sulfate solution in 626.4 g of water and emulsified.
- the macroemulsion thus produced was then brought to a droplet size of approximately 200 nm by passing it three times through an APV-Gaulin high-pressure homogenizer.
- the mini emulsion was stable in storage.
- This solution was then introduced into 4.6 g of a 15% aqueous sodium lauryl sulfate solution in 537.62 g of deionized water and emulsified.
- the mak- roemulsion was then brought to a droplet size of 200 nm by sonication with an ultrasonic finger from Hilscher. This mini emulsion was stable in storage.
- Mini emulsion polymerization and emulsion polymerization 196.4 g (24% of the total amount) of the mini emulsion were placed in a reactor and heated to 80 ° C. At 80 G C 6.9 g of a 2% aqueous solution of sodium persulfate were then added all at once. Subsequently, 621.9 g (76% of the total amount) of the miniemulsion was metered in and, at the same time, a stirred mixture (emulsion) of 23 g of water, 11.5 g of pentaerythritol tetraacrylate and 1.15 g of a 15% strength aqueous sodium lauryl sulfate solution was added in a separate feed within 60 minutes each. The reaction mixture was then stirred at 80 ° C. for a further 30 minutes. After this time, only about 10% of the monomers were polymerized.
- aqueous polymer dispersion was obtained with an average particle diameter of the polymer particles of 492 nm.
- Elmi photographs of powdery polymer particles obtained by drying the aqueous dispersion show, predominantly quite large to 1 ⁇ m large, in some cases very irregularly shaped, are found during the drying process agglomerated particles that carry the UV absorber in the shell and are almost empty in the core.
- the aqueous polymer dispersion which was prepared according to Example 3, was dried to a powder.
- a twin-screw extruder 96.88 parts of polyethylene (Lupolen® 1840 D) were then compounded at 3.12 parts of the powder obtained from the dispersion at a temperature of 200 ° C., and the granules were then processed into a film with a thickness of 100 microns.
- the zero UV-vis spectrum between 200 and 800 nm was first measured on this film.
- the film was then weathered according to ISO 4892-2. After the times given in the table, the transmission was measured at ⁇ max 265 nm. The results are shown in the table. Kneading the aqueous dispersion instead of the powder while evaporating the water gives similarly good results. Comparative Example 1
- Example 4 was repeated with the exception that instead of the powder obtained from the aqueous dispersion prepared according to Example 3, 0.5% of the UV absorber 4-n-octyloxy-2-hydroxybenzophenone was now incorporated into polyethylene, made a film out of it, also weathered it according to ISO 4892-2 and examined it for the transmission according to the times given in the table.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Polymerisation Methods In General (AREA)
- Cosmetics (AREA)
- Paints Or Removers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Description
Claims
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
BRPI0508516-0A BRPI0508516A (pt) | 2004-03-12 | 2005-03-09 | dispersão polimérica aquosa compreendendo substáncias de efeito, processo de produzir a mesma, pó polimérico compreendendo substáncias de efeito, e, uso do mesmo |
US10/592,472 US20070218089A1 (en) | 2004-03-12 | 2005-03-09 | Aqueous Polymer Dispersion Containing Effect Materials, Method for Production and Use Thereof |
JP2007502287A JP4575432B2 (ja) | 2004-03-12 | 2005-03-09 | 作用物質を含有する水性ポリマー分散液、その製造方法及びその使用 |
EP05731798A EP1727834A1 (de) | 2004-03-12 | 2005-03-09 | Effektstoffe enthaltende wässrige polymerdispersionen, verfahren zu ihrer herstellung und ihre verwendung |
IL177653A IL177653A0 (en) | 2004-03-12 | 2006-08-23 | Aqueous polymer dispersion containing effect materials method for production and use thereof |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102004012576.7 | 2004-03-12 | ||
DE102004012576A DE102004012576A1 (de) | 2004-03-12 | 2004-03-12 | Effektstoffe enthaltende wässrige Polymerdispersionen, Verfahren zu ihrer Herstellung und ihre Verwendung |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2005087816A1 true WO2005087816A1 (de) | 2005-09-22 |
Family
ID=34895380
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2005/002484 WO2005087816A1 (de) | 2004-03-12 | 2005-03-09 | Effektstoffe enthaltende wässrige polymerdispersionen, verfahren zu ihrer herstellung und ihre verwendung |
Country Status (9)
Country | Link |
---|---|
US (1) | US20070218089A1 (de) |
EP (1) | EP1727834A1 (de) |
JP (1) | JP4575432B2 (de) |
CN (1) | CN100535021C (de) |
BR (1) | BRPI0508516A (de) |
DE (1) | DE102004012576A1 (de) |
IL (1) | IL177653A0 (de) |
RU (1) | RU2395526C2 (de) |
WO (1) | WO2005087816A1 (de) |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2006094978A2 (de) * | 2005-03-10 | 2006-09-14 | Basf Aktiengesellschaft | Verfahren zur herstellung von pestizide enthaltenden wässrigen polymerdispersionen und ihre verwendung |
WO2007104713A1 (de) * | 2006-03-16 | 2007-09-20 | Basf Se | Effektstoffe enthaltende polymerdispersionen und ihre verwendung |
WO2007147726A1 (de) * | 2006-06-20 | 2007-12-27 | Basf Se | Verfahren zur herstellung von mindestens einen lipophilen wirkstoff enthaltenden wässrigen polymerdispersionen und ihre verwendung |
WO2008074690A1 (de) * | 2006-12-20 | 2008-06-26 | Basf Se | Papierleimungsmittelmischungen |
JP2009046650A (ja) * | 2007-08-20 | 2009-03-05 | Sunjin Chemical Co Ltd | 紫外線遮断剤を含有する高分子複合粒子およびその製造方法 |
EP2508557A1 (de) * | 2011-04-01 | 2012-10-10 | Arkema France | Verfahren zur Herstellung eines pH-unempfindlichen Tensids ohne Polymerteilchendispersion in einem wässrigen Medium |
CN105111374A (zh) * | 2015-08-28 | 2015-12-02 | 烟台德邦科技有限公司 | 一种树脂料的制备方法 |
CN105683227A (zh) * | 2014-09-30 | 2016-06-15 | 积水化成品工业株式会社 | 聚合物颗粒、其制造方法及其用途 |
Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20080287586A1 (en) * | 2007-03-22 | 2008-11-20 | Jones Jamie N | Functionalized nanoparticles and their use in particle/bulk material systems |
AU2008274380B2 (en) * | 2007-07-09 | 2013-04-04 | Basf Se | Water based concentrated product forms of oil-soluble organic UV absorbers |
US8324305B2 (en) * | 2008-07-04 | 2012-12-04 | Basf Se | Process for the homogeneous incorporation of polymer particles into polymeric matrices |
US20120082709A1 (en) * | 2009-06-11 | 2012-04-05 | Landec Corporation | Compositions and methods for delivery of materials |
US9309329B2 (en) | 2010-04-07 | 2016-04-12 | Arkema Inc. | Method for preparing pH-insensitive surfactant free polymer particle dispersion in aqueous medium |
JP5895851B2 (ja) * | 2011-01-25 | 2016-03-30 | 住友大阪セメント株式会社 | 有機系紫外線吸収剤含有樹脂粒子の製造方法 |
JP6028327B2 (ja) * | 2011-12-20 | 2016-11-16 | 住友大阪セメント株式会社 | 紫外線遮蔽複合粒子と紫外線遮蔽多層複合粒子及び紫外線遮蔽分散液並びに化粧料 |
MX2015007705A (es) | 2012-12-21 | 2015-09-08 | Quarzwerke Gmbh | Polimeros termotropos. |
EP3218419A1 (de) | 2014-11-10 | 2017-09-20 | Basf Se | Ethylenpropylheptyl(meth-)acrylatcopolymere |
JP2019077774A (ja) * | 2017-10-24 | 2019-05-23 | ユーエムジー・エービーエス株式会社 | ゴム質重合体、グラフト共重合体、熱可塑性樹脂組成物および成形品の製造方法 |
EP3983834A1 (de) * | 2019-06-12 | 2022-04-20 | 3M Innovative Properties Company | Beschichtetes substrat mit elektrisch leitfähigen teilchen und getrockneter wässriger dispersion eines organischen polymers |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1999040123A2 (de) * | 1998-02-09 | 1999-08-12 | Basf Aktiengesellschaft | Verfahren zur herstellung farbstoffenthaltender, wässriger polymerisatdispersionen |
DE19959927A1 (de) * | 1999-12-11 | 2002-02-07 | Basf Coatings Ag | Wäßrige Primärdispersionen und Beschichtungsstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung |
EP1556416A1 (de) * | 2002-10-18 | 2005-07-27 | Basf Aktiengesellschaft | Alkyldiketene enthaltende wässrige polymerdispersionen, verfahren zu ihrer herstellung und ihre verwendung |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH04288010A (ja) * | 1991-03-15 | 1992-10-13 | Max Fuakutaa Kk | 化粧料 |
JP3199463B2 (ja) * | 1992-07-06 | 2001-08-20 | 王子タック株式会社 | 感光性樹脂組成物 |
US5663213A (en) * | 1994-02-28 | 1997-09-02 | Rohm And Haas Company | Method of improving ultraviolet radiation absorption of a composition |
JPH10152507A (ja) * | 1996-11-22 | 1998-06-09 | Toagosei Co Ltd | 水性エマルジョンの製造方法 |
JP2001181528A (ja) * | 1999-12-27 | 2001-07-03 | Sekisui Chem Co Ltd | 着色微粒子、着色樹脂エマルジョン及びインクジェット印刷用インク |
US6309787B1 (en) * | 2000-04-26 | 2001-10-30 | Xerox Corporation | Aggregation processes |
DE10046927A1 (de) * | 2000-09-21 | 2002-04-25 | Basf Ag | Farbmittelhaltige wässrige Polymerdispersion |
WO2006094978A2 (de) * | 2005-03-10 | 2006-09-14 | Basf Aktiengesellschaft | Verfahren zur herstellung von pestizide enthaltenden wässrigen polymerdispersionen und ihre verwendung |
JP2008533222A (ja) * | 2005-03-10 | 2008-08-21 | ビーエーエスエフ ソシエタス・ヨーロピア | 作用物質を含有する水性ポリマー分散液、それを製造する方法、およびその使用法 |
EP1999163A1 (de) * | 2006-03-16 | 2008-12-10 | Basf Se | Effektstoffe enthaltende polymerdispersionen und ihre verwendung |
-
2004
- 2004-03-12 DE DE102004012576A patent/DE102004012576A1/de not_active Withdrawn
-
2005
- 2005-03-09 CN CN200580007922.4A patent/CN100535021C/zh not_active Expired - Fee Related
- 2005-03-09 EP EP05731798A patent/EP1727834A1/de not_active Withdrawn
- 2005-03-09 RU RU2006135932/04A patent/RU2395526C2/ru not_active IP Right Cessation
- 2005-03-09 US US10/592,472 patent/US20070218089A1/en not_active Abandoned
- 2005-03-09 WO PCT/EP2005/002484 patent/WO2005087816A1/de active Application Filing
- 2005-03-09 JP JP2007502287A patent/JP4575432B2/ja not_active Expired - Fee Related
- 2005-03-09 BR BRPI0508516-0A patent/BRPI0508516A/pt not_active IP Right Cessation
-
2006
- 2006-08-23 IL IL177653A patent/IL177653A0/en unknown
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1999040123A2 (de) * | 1998-02-09 | 1999-08-12 | Basf Aktiengesellschaft | Verfahren zur herstellung farbstoffenthaltender, wässriger polymerisatdispersionen |
DE19959927A1 (de) * | 1999-12-11 | 2002-02-07 | Basf Coatings Ag | Wäßrige Primärdispersionen und Beschichtungsstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung |
EP1556416A1 (de) * | 2002-10-18 | 2005-07-27 | Basf Aktiengesellschaft | Alkyldiketene enthaltende wässrige polymerdispersionen, verfahren zu ihrer herstellung und ihre verwendung |
Cited By (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2006094978A2 (de) * | 2005-03-10 | 2006-09-14 | Basf Aktiengesellschaft | Verfahren zur herstellung von pestizide enthaltenden wässrigen polymerdispersionen und ihre verwendung |
WO2006094978A3 (de) * | 2005-03-10 | 2007-07-12 | Basf Ag | Verfahren zur herstellung von pestizide enthaltenden wässrigen polymerdispersionen und ihre verwendung |
WO2007104713A1 (de) * | 2006-03-16 | 2007-09-20 | Basf Se | Effektstoffe enthaltende polymerdispersionen und ihre verwendung |
JP2009530429A (ja) * | 2006-03-16 | 2009-08-27 | ビーエーエスエフ ソシエタス・ヨーロピア | 作用物質を含有するポリマー分散液及びその使用 |
WO2007147726A1 (de) * | 2006-06-20 | 2007-12-27 | Basf Se | Verfahren zur herstellung von mindestens einen lipophilen wirkstoff enthaltenden wässrigen polymerdispersionen und ihre verwendung |
US8039549B2 (en) | 2006-06-20 | 2011-10-18 | Basf Aktiengesellschaft | Method for producing aqueous polymer dispersions containing at least one lipophilic active substance and the use thereof |
WO2008074690A1 (de) * | 2006-12-20 | 2008-06-26 | Basf Se | Papierleimungsmittelmischungen |
JP2009046650A (ja) * | 2007-08-20 | 2009-03-05 | Sunjin Chemical Co Ltd | 紫外線遮断剤を含有する高分子複合粒子およびその製造方法 |
EP2508557A1 (de) * | 2011-04-01 | 2012-10-10 | Arkema France | Verfahren zur Herstellung eines pH-unempfindlichen Tensids ohne Polymerteilchendispersion in einem wässrigen Medium |
CN105683227A (zh) * | 2014-09-30 | 2016-06-15 | 积水化成品工业株式会社 | 聚合物颗粒、其制造方法及其用途 |
CN105683227B (zh) * | 2014-09-30 | 2019-03-01 | 积水化成品工业株式会社 | 聚合物颗粒、其制造方法及其用途 |
CN105111374A (zh) * | 2015-08-28 | 2015-12-02 | 烟台德邦科技有限公司 | 一种树脂料的制备方法 |
Also Published As
Publication number | Publication date |
---|---|
US20070218089A1 (en) | 2007-09-20 |
RU2006135932A (ru) | 2008-04-20 |
CN1930192A (zh) | 2007-03-14 |
CN100535021C (zh) | 2009-09-02 |
DE102004012576A1 (de) | 2005-09-29 |
RU2395526C2 (ru) | 2010-07-27 |
IL177653A0 (en) | 2006-12-31 |
EP1727834A1 (de) | 2006-12-06 |
JP4575432B2 (ja) | 2010-11-04 |
BRPI0508516A (pt) | 2007-08-14 |
JP2007528926A (ja) | 2007-10-18 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
WO2005087816A1 (de) | Effektstoffe enthaltende wässrige polymerdispersionen, verfahren zu ihrer herstellung und ihre verwendung | |
DE69521009T2 (de) | Verbesserte Verfahren zur Herstellung von Polymere | |
DE2331141C2 (de) | Verfahren zur Herstellung von Lactices durch Emulsionspolymerisation | |
EP1789456B1 (de) | Verfahren zur herstellung von polymeren durch sprühpolymerisation | |
WO2008055858A2 (de) | Feinteilige, stärkehaltige polymerdispersionen | |
EP1966248A1 (de) | Wässrige dispersionen von polymeren, die einen fluoreszenzfarbstoff enthalten, verfahren zu ihrer herstellung und ihre verwendung zum markieren von materialien | |
DE19548038A1 (de) | Verfahren zur Herstellung von Polymerisaten durch Emulsionspolymerisation | |
WO2007104713A1 (de) | Effektstoffe enthaltende polymerdispersionen und ihre verwendung | |
EP2035462A1 (de) | Verfahren zur herstellung von mindestens einen lipophilen wirkstoff enthaltenden wässrigen polymerdispersionen und ihre verwendung | |
DE60034106T2 (de) | Wässrige emulsionspolymerisat-zusammensetzungen und ihre verwendung zur papierleimung | |
EP2102249B1 (de) | Feinteilige, kationische polymerdispersionen | |
EP1624974A2 (de) | Polymerdispersion mit farbeffekt | |
DE19624280A1 (de) | Verfahren zur Herstellung niedrigviskoser, wässriger Polymerisatdispersionen mit Polymervolumenkonzentrationen von wenigstens 50 Vol.-% | |
DE60114959T2 (de) | Verfahren zur Herstellung von Polyvinylester-Harzzusammensetzungen | |
WO2008034813A1 (de) | Teilchen enthaltend polymeradditive | |
DE10248879A1 (de) | Alkyldiketene enthaltende wässrige Polymerdispersionen, Verfahren zu ihrer Herstellung und ihre Verwendung | |
WO2005070912A1 (de) | Alkenylbernsteinsäureanhydride enthaltende wässrige polymerdispersionen, verfahren zu ihrer herstellung und ihre verwendung | |
DE2344553C3 (de) | Verfahren zur Herstellung von PoIyvinylchloridpfropfcopolymeren | |
DE854851C (de) | Verfahren zur Herstellung von Interpolymeren | |
DE60200026T2 (de) | Gelfreie hochmolekulare Massen sowie thermoplastische Mischungen hiervon | |
WO2010000833A1 (de) | Verfahren zur homogenen einarbeitung von polymerpartikeln in polymere matrices | |
MXPA06009774A (en) | Aqueous polymer dispersion containing effect materials method for production and use thereof | |
DE1570990A1 (de) | Verfahren zur Herstellung von Vinylhalogenpolymerisaten,insbesondere von gepfropften Polyvinylhalogen-Polyolefinpolymerisaten und Mischungen | |
CH481954A (de) | Verfahren zur Herstellung von gegen die Einwirkung ultravioletter Strahlen geschützten Polymeren | |
DE2417343C2 (de) | Kontinuierliches Verfahren zur Herstellung von Gemischen aus Äthylen-Copolymerisaten und Wachs |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AK | Designated states |
Kind code of ref document: A1 Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BW BY BZ CA CH CN CO CR CU CZ DE DK DM DZ EC EE EG ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NA NI NO NZ OM PG PH PL PT RO RU SC SD SE SG SK SL SM SY TJ TM TN TR TT TZ UA UG US UZ VC VN YU ZA ZM ZW |
|
AL | Designated countries for regional patents |
Kind code of ref document: A1 Designated state(s): BW GH GM KE LS MW MZ NA SD SL SZ TZ UG ZM ZW AM AZ BY KG KZ MD RU TJ TM AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IS IT LT LU MC NL PL PT RO SE SI SK TR BF BJ CF CG CI CM GA GN GQ GW ML MR NE SN TD TG |
|
121 | Ep: the epo has been informed by wipo that ep was designated in this application | ||
DPEN | Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed from 20040101) | ||
WWE | Wipo information: entry into national phase |
Ref document number: 2005731798 Country of ref document: EP |
|
WWE | Wipo information: entry into national phase |
Ref document number: 177653 Country of ref document: IL |
|
WWE | Wipo information: entry into national phase |
Ref document number: PA/a/2006/009774 Country of ref document: MX |
|
WWE | Wipo information: entry into national phase |
Ref document number: 10592472 Country of ref document: US Ref document number: 2007218089 Country of ref document: US |
|
WWE | Wipo information: entry into national phase |
Ref document number: 200580007922.4 Country of ref document: CN Ref document number: 2007502287 Country of ref document: JP |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
WWW | Wipo information: withdrawn in national office |
Ref document number: DE |
|
WWE | Wipo information: entry into national phase |
Ref document number: 200608433 Country of ref document: ZA |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2006135932 Country of ref document: RU |
|
WWP | Wipo information: published in national office |
Ref document number: 2005731798 Country of ref document: EP |
|
ENP | Entry into the national phase |
Ref document number: PI0508516 Country of ref document: BR |
|
WWP | Wipo information: published in national office |
Ref document number: 10592472 Country of ref document: US |