AU2012362497B2 - Methods of producing a titanium dioxide pigment and improving the processability of titanium dioxide pigment particles - Google Patents
Methods of producing a titanium dioxide pigment and improving the processability of titanium dioxide pigment particles Download PDFInfo
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- AU2012362497B2 AU2012362497B2 AU2012362497A AU2012362497A AU2012362497B2 AU 2012362497 B2 AU2012362497 B2 AU 2012362497B2 AU 2012362497 A AU2012362497 A AU 2012362497A AU 2012362497 A AU2012362497 A AU 2012362497A AU 2012362497 B2 AU2012362497 B2 AU 2012362497B2
- Authority
- AU
- Australia
- Prior art keywords
- titanium dioxide
- dioxide particles
- treating agent
- agglomerator
- pigment
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
Links
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 title claims abstract description 497
- 239000004408 titanium dioxide Substances 0.000 title claims abstract description 220
- 239000002245 particle Substances 0.000 title claims abstract description 130
- 239000000049 pigment Substances 0.000 title claims abstract description 129
- 238000000034 method Methods 0.000 title claims abstract description 109
- 230000002411 adverse Effects 0.000 claims abstract description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 67
- -1 polysiloxanes Polymers 0.000 claims description 43
- 239000000203 mixture Substances 0.000 claims description 33
- 230000002209 hydrophobic effect Effects 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 claims description 13
- 229920001296 polysiloxane Polymers 0.000 claims description 13
- 150000004756 silanes Chemical class 0.000 claims description 13
- 239000007921 spray Substances 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000000843 powder Substances 0.000 claims description 8
- 238000005507 spraying Methods 0.000 claims description 8
- 150000003009 phosphonic acids Chemical class 0.000 claims description 7
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 6
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims description 6
- MSRJTTSHWYDFIU-UHFFFAOYSA-N octyltriethoxysilane Chemical group CCCCCCCC[Si](OCC)(OCC)OCC MSRJTTSHWYDFIU-UHFFFAOYSA-N 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 239000011164 primary particle Substances 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 238000012360 testing method Methods 0.000 description 65
- 230000008569 process Effects 0.000 description 32
- 238000010410 dusting Methods 0.000 description 25
- 238000010998 test method Methods 0.000 description 16
- 229920000642 polymer Polymers 0.000 description 15
- 238000005054 agglomeration Methods 0.000 description 13
- 230000002776 aggregation Effects 0.000 description 13
- 238000004519 manufacturing process Methods 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 10
- 239000004205 dimethyl polysiloxane Substances 0.000 description 9
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 9
- 239000000428 dust Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 7
- 239000012141 concentrate Substances 0.000 description 7
- 230000007246 mechanism Effects 0.000 description 7
- CXQXSVUQTKDNFP-UHFFFAOYSA-N octamethyltrisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C CXQXSVUQTKDNFP-UHFFFAOYSA-N 0.000 description 7
- 238000004987 plasma desorption mass spectroscopy Methods 0.000 description 7
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 5
- 230000006872 improvement Effects 0.000 description 5
- 238000005029 sieve analysis Methods 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 238000010586 diagram Methods 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 230000014759 maintenance of location Effects 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- 238000009826 distribution Methods 0.000 description 3
- 239000010419 fine particle Substances 0.000 description 3
- 229920001684 low density polyethylene Polymers 0.000 description 3
- 239000004702 low-density polyethylene Substances 0.000 description 3
- 229920000098 polyolefin Polymers 0.000 description 3
- 239000004800 polyvinyl chloride Substances 0.000 description 3
- 230000000717 retained effect Effects 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000010936 titanium Substances 0.000 description 3
- 229910052719 titanium Inorganic materials 0.000 description 3
- JJJOZVFVARQUJV-UHFFFAOYSA-N 2-ethylhexylphosphonic acid Chemical class CCCCC(CC)CP(O)(O)=O JJJOZVFVARQUJV-UHFFFAOYSA-N 0.000 description 2
- MSKZTCBQQBFONJ-UHFFFAOYSA-N 2-methyloctylphosphonic acid Chemical class CCCCCCC(C)CP(O)(O)=O MSKZTCBQQBFONJ-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 239000004594 Masterbatch (MB) Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 2
- 235000013539 calcium stearate Nutrition 0.000 description 2
- 239000008116 calcium stearate Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- NBWIIOQJUKRLKW-UHFFFAOYSA-N chloro(phenyl)silane Chemical class Cl[SiH2]C1=CC=CC=C1 NBWIIOQJUKRLKW-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- GOIPELYWYGMEFQ-UHFFFAOYSA-N dimethoxy-methyl-octylsilane Chemical compound CCCCCCCC[Si](C)(OC)OC GOIPELYWYGMEFQ-UHFFFAOYSA-N 0.000 description 2
- 229920006351 engineering plastic Polymers 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- GJWAEWLHSDGBGG-UHFFFAOYSA-N hexylphosphonic acid Chemical class CCCCCCP(O)(O)=O GJWAEWLHSDGBGG-UHFFFAOYSA-N 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- NJGCRMAPOWGWMW-UHFFFAOYSA-N octylphosphonic acid Chemical class CCCCCCCCP(O)(O)=O NJGCRMAPOWGWMW-UHFFFAOYSA-N 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- SECPZKHBENQXJG-FPLPWBNLSA-N palmitoleic acid Chemical compound CCCCCC\C=C/CCCCCCCC(O)=O SECPZKHBENQXJG-FPLPWBNLSA-N 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 229920000915 polyvinyl chloride Polymers 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000010079 rubber tapping Methods 0.000 description 2
- 238000012956 testing procedure Methods 0.000 description 2
- 229910000349 titanium oxysulfate Inorganic materials 0.000 description 2
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 2
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- KAKVFSYQVNHFBS-UHFFFAOYSA-N (5-hydroxycyclopenten-1-yl)-phenylmethanone Chemical compound OC1CCC=C1C(=O)C1=CC=CC=C1 KAKVFSYQVNHFBS-UHFFFAOYSA-N 0.000 description 1
- SOQQSPURSLWWMI-UHFFFAOYSA-N 1,3-thiazole-4-carbothioamide Chemical compound NC(=S)C1=CSC=N1 SOQQSPURSLWWMI-UHFFFAOYSA-N 0.000 description 1
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 1
- VOQMPZXAFLPTMM-UHFFFAOYSA-N 4-(4-chlorophenoxy)piperidine Chemical class C1=CC(Cl)=CC=C1OC1CCNCC1 VOQMPZXAFLPTMM-UHFFFAOYSA-N 0.000 description 1
- OGBVRMYSNSKIEF-UHFFFAOYSA-N Benzylphosphonic acid Chemical class OP(O)(=O)CC1=CC=CC=C1 OGBVRMYSNSKIEF-UHFFFAOYSA-N 0.000 description 1
- ROZZMLUWBPPEMU-GRVYQHKQSA-L Calcium linoleate Chemical compound [Ca+2].CCCCC\C=C/C\C=C/CCCCCCCC([O-])=O.CCCCC\C=C/C\C=C/CCCCCCCC([O-])=O ROZZMLUWBPPEMU-GRVYQHKQSA-L 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 239000005046 Chlorosilane Substances 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- BCKXLBQYZLBQEK-KVVVOXFISA-M Sodium oleate Chemical compound [Na+].CCCCCCCC\C=C/CCCCCCCC([O-])=O BCKXLBQYZLBQEK-KVVVOXFISA-M 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940078456 calcium stearate Drugs 0.000 description 1
- TVGWTYKLLHJPEZ-VKRZFSCASA-L calcium;(z)-tetradec-9-enoate Chemical compound [Ca+2].CCCC\C=C/CCCCCCCC([O-])=O.CCCC\C=C/CCCCCCCC([O-])=O TVGWTYKLLHJPEZ-VKRZFSCASA-L 0.000 description 1
- HIAAVKYLDRCDFQ-UHFFFAOYSA-L calcium;dodecanoate Chemical compound [Ca+2].CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O HIAAVKYLDRCDFQ-UHFFFAOYSA-L 0.000 description 1
- HRBZRZSCMANEHQ-UHFFFAOYSA-L calcium;hexadecanoate Chemical compound [Ca+2].CCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCC([O-])=O HRBZRZSCMANEHQ-UHFFFAOYSA-L 0.000 description 1
- ZCZLQYAECBEUBH-UHFFFAOYSA-L calcium;octadec-9-enoate Chemical compound [Ca+2].CCCCCCCCC=CCCCCCCCC([O-])=O.CCCCCCCCC=CCCCCCCCC([O-])=O ZCZLQYAECBEUBH-UHFFFAOYSA-L 0.000 description 1
- LSFBQOPXRBJSSI-UHFFFAOYSA-L calcium;tetradecanoate Chemical compound [Ca+2].CCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCC([O-])=O LSFBQOPXRBJSSI-UHFFFAOYSA-L 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- MNKYQPOFRKPUAE-UHFFFAOYSA-N chloro(triphenyl)silane Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 MNKYQPOFRKPUAE-UHFFFAOYSA-N 0.000 description 1
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical class Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 1
- 239000000571 coke Substances 0.000 description 1
- 238000005056 compaction Methods 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 230000001010 compromised effect Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- DZQISOJKASMITI-UHFFFAOYSA-N decyl-dioxido-oxo-$l^{5}-phosphane;hydron Chemical class CCCCCCCCCCP(O)(O)=O DZQISOJKASMITI-UHFFFAOYSA-N 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- OSXYHAQZDCICNX-UHFFFAOYSA-N dichloro(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](Cl)(Cl)C1=CC=CC=C1 OSXYHAQZDCICNX-UHFFFAOYSA-N 0.000 description 1
- KKRMHVJQWMXYBZ-UHFFFAOYSA-N dichloro-hexyl-methylsilane Chemical compound CCCCCC[Si](C)(Cl)Cl KKRMHVJQWMXYBZ-UHFFFAOYSA-N 0.000 description 1
- QHBMMABVNRSRHW-UHFFFAOYSA-N dichloro-methyl-octylsilane Chemical compound CCCCCCCC[Si](C)(Cl)Cl QHBMMABVNRSRHW-UHFFFAOYSA-N 0.000 description 1
- MROCJMGDEKINLD-UHFFFAOYSA-N dichlorosilane Chemical class Cl[SiH2]Cl MROCJMGDEKINLD-UHFFFAOYSA-N 0.000 description 1
- YTDDWYQXURUACY-UHFFFAOYSA-N diethoxy-hexyl-methylsilane Chemical compound CCCCCC[Si](C)(OCC)OCC YTDDWYQXURUACY-UHFFFAOYSA-N 0.000 description 1
- ZXPDYFSTVHQQOI-UHFFFAOYSA-N diethoxysilane Chemical class CCO[SiH2]OCC ZXPDYFSTVHQQOI-UHFFFAOYSA-N 0.000 description 1
- 125000004177 diethyl group Chemical class [H]C([H])([H])C([H])([H])* 0.000 description 1
- AHUXYBVKTIBBJW-UHFFFAOYSA-N dimethoxy(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](OC)(OC)C1=CC=CC=C1 AHUXYBVKTIBBJW-UHFFFAOYSA-N 0.000 description 1
- XRGNCULGAXHDLD-UHFFFAOYSA-N dimethoxy(trityloxy)silane Chemical compound C1(=CC=CC=C1)C(O[SiH](OC)OC)(C1=CC=CC=C1)C1=CC=CC=C1 XRGNCULGAXHDLD-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical class [H]C([H])([H])* 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- SVMUEEINWGBIPD-UHFFFAOYSA-N dodecylphosphonic acid Chemical class CCCCCCCCCCCCP(O)(O)=O SVMUEEINWGBIPD-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000005243 fluidization Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- JDPSFRXPDJVJMV-UHFFFAOYSA-N hexadecylphosphonic acid Chemical class CCCCCCCCCCCCCCCCP(O)(O)=O JDPSFRXPDJVJMV-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- CZWLNMOIEMTDJY-UHFFFAOYSA-N hexyl(trimethoxy)silane Chemical compound CCCCCC[Si](OC)(OC)OC CZWLNMOIEMTDJY-UHFFFAOYSA-N 0.000 description 1
- APQKDJQPCPXLQL-UHFFFAOYSA-N hexyl-dimethoxy-methylsilane Chemical compound CCCCCC[Si](C)(OC)OC APQKDJQPCPXLQL-UHFFFAOYSA-N 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- YDZQQRWRVYGNER-UHFFFAOYSA-N iron;titanium;trihydrate Chemical compound O.O.O.[Ti].[Fe] YDZQQRWRVYGNER-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 229940105112 magnesium myristate Drugs 0.000 description 1
- 229940063002 magnesium palmitate Drugs 0.000 description 1
- 229940057948 magnesium stearate Drugs 0.000 description 1
- BJZBHTNKDCBDNQ-UHFFFAOYSA-L magnesium;dodecanoate Chemical compound [Mg+2].CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O BJZBHTNKDCBDNQ-UHFFFAOYSA-L 0.000 description 1
- ABSWXCXMXIZDSN-UHFFFAOYSA-L magnesium;hexadecanoate Chemical compound [Mg+2].CCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCC([O-])=O ABSWXCXMXIZDSN-UHFFFAOYSA-L 0.000 description 1
- DMRBHZWQMKSQGR-UHFFFAOYSA-L magnesium;tetradecanoate Chemical compound [Mg+2].CCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCC([O-])=O DMRBHZWQMKSQGR-UHFFFAOYSA-L 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229960003493 octyltriethoxysilane Drugs 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000005054 phenyltrichlorosilane Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920000307 polymer substrate Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229940096992 potassium oleate Drugs 0.000 description 1
- 229940114930 potassium stearate Drugs 0.000 description 1
- MHUCSRUPTZFQQD-CFYXSCKTSA-M potassium;(z)-hexadec-9-enoate Chemical compound [K+].CCCCCC\C=C/CCCCCCCC([O-])=O MHUCSRUPTZFQQD-CFYXSCKTSA-M 0.000 description 1
- MLICVSDCCDDWMD-KVVVOXFISA-M potassium;(z)-octadec-9-enoate Chemical compound [K+].CCCCCCCC\C=C/CCCCCCCC([O-])=O MLICVSDCCDDWMD-KVVVOXFISA-M 0.000 description 1
- NBQYYGCNAPFWQV-YSMBQZINSA-M potassium;(z)-tetradec-9-enoate Chemical compound [K+].CCCC\C=C/CCCCCCCC([O-])=O NBQYYGCNAPFWQV-YSMBQZINSA-M 0.000 description 1
- MQOCIYICOGDBSG-UHFFFAOYSA-M potassium;hexadecanoate Chemical compound [K+].CCCCCCCCCCCCCCCC([O-])=O MQOCIYICOGDBSG-UHFFFAOYSA-M 0.000 description 1
- ANBFRLKBEIFNQU-UHFFFAOYSA-M potassium;octadecanoate Chemical compound [K+].CCCCCCCCCCCCCCCCCC([O-])=O ANBFRLKBEIFNQU-UHFFFAOYSA-M 0.000 description 1
- PYJBVGYZXWPIKK-UHFFFAOYSA-M potassium;tetradecanoate Chemical compound [K+].CCCCCCCCCCCCCC([O-])=O PYJBVGYZXWPIKK-UHFFFAOYSA-M 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002893 slag Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- BTURAGWYSMTVOW-UHFFFAOYSA-M sodium dodecanoate Chemical compound [Na+].CCCCCCCCCCCC([O-])=O BTURAGWYSMTVOW-UHFFFAOYSA-M 0.000 description 1
- 229940082004 sodium laurate Drugs 0.000 description 1
- 229940045845 sodium myristate Drugs 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- 229940045870 sodium palmitate Drugs 0.000 description 1
- 229940080350 sodium stearate Drugs 0.000 description 1
- WYPBVHPKMJYUEO-NBTZWHCOSA-M sodium;(9z,12z)-octadeca-9,12-dienoate Chemical compound [Na+].CCCCC\C=C/C\C=C/CCCCCCCC([O-])=O WYPBVHPKMJYUEO-NBTZWHCOSA-M 0.000 description 1
- AQADNICIQOBXGR-CFYXSCKTSA-M sodium;(z)-hexadec-9-enoate Chemical compound [Na+].CCCCCC\C=C/CCCCCCCC([O-])=O AQADNICIQOBXGR-CFYXSCKTSA-M 0.000 description 1
- MULNDDKISACMFY-YSMBQZINSA-M sodium;(z)-tetradec-9-enoate Chemical compound [Na+].CCCC\C=C/CCCCCCCC([O-])=O MULNDDKISACMFY-YSMBQZINSA-M 0.000 description 1
- GGXKEBACDBNFAF-UHFFFAOYSA-M sodium;hexadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCC([O-])=O GGXKEBACDBNFAF-UHFFFAOYSA-M 0.000 description 1
- JUQGWKYSEXPRGL-UHFFFAOYSA-M sodium;tetradecanoate Chemical compound [Na+].CCCCCCCCCCCCCC([O-])=O JUQGWKYSEXPRGL-UHFFFAOYSA-M 0.000 description 1
- 238000007619 statistical method Methods 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- BVQJQTMSTANITJ-UHFFFAOYSA-N tetradecylphosphonic acid Chemical class CCCCCCCCCCCCCCP(O)(O)=O BVQJQTMSTANITJ-UHFFFAOYSA-N 0.000 description 1
- LFXJGGDONSCPOF-UHFFFAOYSA-N trichloro(hexyl)silane Chemical compound CCCCCC[Si](Cl)(Cl)Cl LFXJGGDONSCPOF-UHFFFAOYSA-N 0.000 description 1
- RCHUVCPBWWSUMC-UHFFFAOYSA-N trichloro(octyl)silane Chemical compound CCCCCCCC[Si](Cl)(Cl)Cl RCHUVCPBWWSUMC-UHFFFAOYSA-N 0.000 description 1
- ORVMIVQULIKXCP-UHFFFAOYSA-N trichloro(phenyl)silane Chemical compound Cl[Si](Cl)(Cl)C1=CC=CC=C1 ORVMIVQULIKXCP-UHFFFAOYSA-N 0.000 description 1
- WUMSTCDLAYQDNO-UHFFFAOYSA-N triethoxy(hexyl)silane Chemical compound CCCCCC[Si](OCC)(OCC)OCC WUMSTCDLAYQDNO-UHFFFAOYSA-N 0.000 description 1
- NMEPHPOFYLLFTK-UHFFFAOYSA-N trimethoxy(octyl)silane Chemical compound CCCCCCCC[Si](OC)(OC)OC NMEPHPOFYLLFTK-UHFFFAOYSA-N 0.000 description 1
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 1
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 229940098697 zinc laurate Drugs 0.000 description 1
- 229940105125 zinc myristate Drugs 0.000 description 1
- 229940012185 zinc palmitate Drugs 0.000 description 1
- 229940057977 zinc stearate Drugs 0.000 description 1
- ODNJVAVDJKOYFK-GRVYQHKQSA-L zinc;(9z,12z)-octadeca-9,12-dienoate Chemical compound [Zn+2].CCCCC\C=C/C\C=C/CCCCCCCC([O-])=O.CCCCC\C=C/C\C=C/CCCCCCCC([O-])=O ODNJVAVDJKOYFK-GRVYQHKQSA-L 0.000 description 1
- LPEBYPDZMWMCLZ-CVBJKYQLSA-L zinc;(z)-octadec-9-enoate Chemical compound [Zn+2].CCCCCCCC\C=C/CCCCCCCC([O-])=O.CCCCCCCC\C=C/CCCCCCCC([O-])=O LPEBYPDZMWMCLZ-CVBJKYQLSA-L 0.000 description 1
- SHUZUXOTLJTHSS-VKRZFSCASA-L zinc;(z)-tetradec-9-enoate Chemical compound [Zn+2].CCCC\C=C/CCCCCCCC([O-])=O.CCCC\C=C/CCCCCCCC([O-])=O SHUZUXOTLJTHSS-VKRZFSCASA-L 0.000 description 1
- GPYYEEJOMCKTPR-UHFFFAOYSA-L zinc;dodecanoate Chemical compound [Zn+2].CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O GPYYEEJOMCKTPR-UHFFFAOYSA-L 0.000 description 1
- GJAPSKMAVXDBIU-UHFFFAOYSA-L zinc;hexadecanoate Chemical compound [Zn+2].CCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCC([O-])=O GJAPSKMAVXDBIU-UHFFFAOYSA-L 0.000 description 1
- GBFLQPIIIRJQLU-UHFFFAOYSA-L zinc;tetradecanoate Chemical compound [Zn+2].CCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCC([O-])=O GBFLQPIIIRJQLU-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
- C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
- C09C1/36—Compounds of titanium
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01G—COMPOUNDS CONTAINING METALS NOT COVERED BY SUBCLASSES C01D OR C01F
- C01G23/00—Compounds of titanium
- C01G23/04—Oxides; Hydroxides
- C01G23/047—Titanium dioxide
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
- C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
- C09C1/36—Compounds of titanium
- C09C1/3607—Titanium dioxide
- C09C1/3676—Treatment with macro-molecular organic compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
- C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
- C09C1/36—Compounds of titanium
- C09C1/3607—Titanium dioxide
- C09C1/3684—Treatment with organo-silicon compounds
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
- C01P2004/00—Particle morphology
- C01P2004/50—Agglomerated particles
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
- C01P2004/00—Particle morphology
- C01P2004/60—Particles characterised by their size
- C01P2004/62—Submicrometer sized, i.e. from 0.1-1 micrometer
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Environmental & Geological Engineering (AREA)
- General Life Sciences & Earth Sciences (AREA)
- Geology (AREA)
- Inorganic Chemistry (AREA)
- Pigments, Carbon Blacks, Or Wood Stains (AREA)
- Inorganic Compounds Of Heavy Metals (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13/337,839 US8663518B2 (en) | 2011-12-27 | 2011-12-27 | Methods of producing a titanium dioxide pigment and improving the processability of titanium dioxide pigment particles |
| US13/337,839 | 2011-12-27 | ||
| PCT/US2012/071664 WO2013101838A1 (en) | 2011-12-27 | 2012-12-26 | Methods of producing a titanium dioxide pigment and improving the processability of titanium dioxide pigment particles |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2012362497A1 AU2012362497A1 (en) | 2014-03-13 |
| AU2012362497B2 true AU2012362497B2 (en) | 2015-05-14 |
Family
ID=48653739
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2012362497A Ceased AU2012362497B2 (en) | 2011-12-27 | 2012-12-26 | Methods of producing a titanium dioxide pigment and improving the processability of titanium dioxide pigment particles |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US8663518B2 (enExample) |
| EP (1) | EP2751209B1 (enExample) |
| JP (1) | JP2015508441A (enExample) |
| CN (1) | CN103814090B (enExample) |
| AU (1) | AU2012362497B2 (enExample) |
| CA (1) | CA2846641C (enExample) |
| DK (1) | DK2751209T3 (enExample) |
| ES (1) | ES2831050T3 (enExample) |
| MX (1) | MX2014007599A (enExample) |
| MY (1) | MY165161A (enExample) |
| PL (1) | PL2751209T3 (enExample) |
| SI (1) | SI2751209T1 (enExample) |
| TW (1) | TWI492901B (enExample) |
| WO (1) | WO2013101838A1 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10308816B2 (en) | 2014-05-05 | 2019-06-04 | Potters Industries, Llc | Coatings for pelletized thermoplastic pavement marking compositions |
| CN104194407A (zh) * | 2014-06-03 | 2014-12-10 | 安徽奥邦新材料有限公司 | 一种新型改性二氧化钛白色防锈颜料及其制备方法 |
| GB201517478D0 (en) * | 2015-10-02 | 2015-11-18 | Tioxide Europe Ltd | Particle surface treatment |
| CN105623312A (zh) * | 2016-01-05 | 2016-06-01 | 天津先光化工有限公司 | 一种干法制备硅处理钛白粉的方法 |
| CN108948799A (zh) * | 2018-07-10 | 2018-12-07 | 四川龙蟒钛业股份有限公司 | 一种高档色母级钛白粉的生产方法 |
| TWI686251B (zh) * | 2018-11-30 | 2020-03-01 | 財團法人金屬工業研究發展中心 | 微粉成型裝置 |
| US20250026908A1 (en) * | 2023-07-14 | 2025-01-23 | Tronox Llc | Inorganic pigment treated with phms/pdms copolymer |
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| US6302926B1 (en) * | 1994-06-24 | 2001-10-16 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Preparations of monodisperse spherical oxide particles |
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| US3899346A (en) | 1972-11-15 | 1975-08-12 | Thomas Howard Ferrigno | Opacity modified pigmentary compositions |
| GB1541928A (en) | 1975-12-23 | 1979-03-14 | Sakai Chemical Industry Co | Production of shaped catalysts or carriers comprising titanium oxide |
| DE3628320A1 (de) | 1986-08-21 | 1988-02-25 | Bayer Ag | Hydrophobe pigmente und fuellstoffe fuer die einarbeitung in kunststoffe |
| FR2623793B1 (fr) * | 1987-11-30 | 1991-06-07 | Rhone Poulenc Chimie | Procede de preparation de granules a base d'oxyde de titane, de zirconium, ou de cerium et produits ainsi obtenus |
| US6149712A (en) | 1988-07-26 | 2000-11-21 | Commonwealth Scientific & Industrial Research Organisation | Sintered high titanium agglomerates |
| DE3841848A1 (de) | 1988-12-13 | 1990-06-21 | Bayer Ag | Anorganische pigmente mit verbesserten eigenschaften |
| US5418198A (en) | 1993-08-23 | 1995-05-23 | Magneco/Metrel, Inc. | Pelletizable gunning composition |
| DE4336612C2 (de) * | 1993-10-27 | 1995-09-07 | Bayer Ag | Mehrstufiges Verfahren zur Herstellung von anorganischen Pigmentgranulaten und deren Verwendung zur Färbung von Kunststoffen und zur Herstellung von Pulverlacken |
| US5501732A (en) * | 1994-02-28 | 1996-03-26 | E. I. Du Pont De Nemours And Company | Process for preparing silanized TiO2 pigments using a media mill |
| ES2156195T3 (es) | 1994-10-14 | 2001-06-16 | Tioxide Group Services Ltd | Particulas inorganicas revestidas con un acido alquilfosfonico o un ester del mismo, su preparacion y su uso. |
| JPH08259290A (ja) | 1995-01-27 | 1996-10-08 | Kanegafuchi Chem Ind Co Ltd | 軽量骨材の製造方法 |
| GB2299682B (en) | 1995-03-31 | 1998-10-28 | Fuji Electric Co Ltd | Electrophotographic photoconductor and process for producing the same |
| JPH08328283A (ja) * | 1995-03-31 | 1996-12-13 | Fuji Electric Co Ltd | 電子写真用感光体およびその製造方法 |
| US5653794A (en) * | 1995-12-01 | 1997-08-05 | Scm Chemicals, Inc. | Silane treated inorganic pigments |
| WO1997030127A1 (en) * | 1996-02-16 | 1997-08-21 | Kerr-Mcgee Chemical Corporation | Process for preparing an improved low-dusting, free-flowing pigment |
| JPH1060157A (ja) * | 1996-08-14 | 1998-03-03 | Showa Denko Kk | 二酸化チタン顔料含有熱可塑性樹脂組成物およびマスターバッチ並びにそれらの製造方法 |
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| JP2003002710A (ja) * | 2001-06-18 | 2003-01-08 | Mitsui Mining & Smelting Co Ltd | 膨張粒子及びその製造方法 |
| JP2004000882A (ja) | 2002-04-17 | 2004-01-08 | Kobe Steel Ltd | 重金属及び／又は有機化合物の処理方法 |
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| DE10344660A1 (de) * | 2003-09-25 | 2005-04-28 | Merck Patent Gmbh | Verkapselte Pigmente |
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| TW201034966A (en) | 2008-12-23 | 2010-10-01 | Millennium Inorganic Chem | Method for preparing agglomerated metal oxides |
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-
2011
- 2011-12-27 US US13/337,839 patent/US8663518B2/en active Active
-
2012
- 2012-12-18 TW TW101148128A patent/TWI492901B/zh active
- 2012-12-26 PL PL12862558T patent/PL2751209T3/pl unknown
- 2012-12-26 ES ES12862558T patent/ES2831050T3/es active Active
- 2012-12-26 CA CA2846641A patent/CA2846641C/en active Active
- 2012-12-26 WO PCT/US2012/071664 patent/WO2013101838A1/en not_active Ceased
- 2012-12-26 MX MX2014007599A patent/MX2014007599A/es active IP Right Grant
- 2012-12-26 SI SI201231851T patent/SI2751209T1/sl unknown
- 2012-12-26 EP EP12862558.9A patent/EP2751209B1/en active Active
- 2012-12-26 MY MYPI2014001879A patent/MY165161A/en unknown
- 2012-12-26 JP JP2014550432A patent/JP2015508441A/ja active Pending
- 2012-12-26 AU AU2012362497A patent/AU2012362497B2/en not_active Ceased
- 2012-12-26 DK DK12862558.9T patent/DK2751209T3/da active
- 2012-12-26 CN CN201280045530.7A patent/CN103814090B/zh active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6302926B1 (en) * | 1994-06-24 | 2001-10-16 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Preparations of monodisperse spherical oxide particles |
Also Published As
| Publication number | Publication date |
|---|---|
| MY165161A (en) | 2018-02-28 |
| CA2846641C (en) | 2017-07-18 |
| WO2013101838A1 (en) | 2013-07-04 |
| AU2012362497A1 (en) | 2014-03-13 |
| CA2846641A1 (en) | 2013-07-04 |
| CN103814090A (zh) | 2014-05-21 |
| MX2014007599A (es) | 2014-09-15 |
| SI2751209T1 (sl) | 2020-12-31 |
| PL2751209T3 (pl) | 2021-03-08 |
| JP2015508441A (ja) | 2015-03-19 |
| TWI492901B (zh) | 2015-07-21 |
| EP2751209A4 (en) | 2016-01-13 |
| DK2751209T3 (da) | 2020-10-26 |
| ES2831050T3 (es) | 2021-06-07 |
| TW201335073A (zh) | 2013-09-01 |
| US20130161856A1 (en) | 2013-06-27 |
| US8663518B2 (en) | 2014-03-04 |
| EP2751209B1 (en) | 2020-09-30 |
| CN103814090B (zh) | 2016-10-05 |
| EP2751209A1 (en) | 2014-07-09 |
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