EP3007813A1 - Phosphate ester dispersion promoting agent and dispersion comprising the same - Google Patents
Phosphate ester dispersion promoting agent and dispersion comprising the sameInfo
- Publication number
- EP3007813A1 EP3007813A1 EP14810305.4A EP14810305A EP3007813A1 EP 3007813 A1 EP3007813 A1 EP 3007813A1 EP 14810305 A EP14810305 A EP 14810305A EP 3007813 A1 EP3007813 A1 EP 3007813A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- acid
- dispersion
- range
- phosphate ester
- substituted
- 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.)
- Withdrawn
Links
- -1 Phosphate ester Chemical class 0.000 title claims abstract description 107
- 239000006185 dispersion Substances 0.000 title claims abstract description 107
- 239000003795 chemical substances by application Substances 0.000 title claims abstract description 65
- 229910019142 PO4 Inorganic materials 0.000 title claims abstract description 56
- 239000010452 phosphate Substances 0.000 title claims abstract description 56
- 230000001737 promoting effect Effects 0.000 title claims abstract description 46
- 239000007787 solid Substances 0.000 claims abstract description 64
- 229920000728 polyester Polymers 0.000 claims abstract description 29
- 238000000034 method Methods 0.000 claims abstract description 23
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 19
- 238000002360 preparation method Methods 0.000 claims abstract description 14
- 239000002253 acid Substances 0.000 claims description 26
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 22
- 238000005886 esterification reaction Methods 0.000 claims description 20
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 19
- 150000002009 diols Chemical class 0.000 claims description 18
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 17
- 125000002947 alkylene group Chemical group 0.000 claims description 16
- ULQISTXYYBZJSJ-UHFFFAOYSA-N 12-hydroxyoctadecanoic acid Chemical compound CCCCCCC(O)CCCCCCCCCCC(O)=O ULQISTXYYBZJSJ-UHFFFAOYSA-N 0.000 claims description 14
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 14
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 13
- 230000032050 esterification Effects 0.000 claims description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 11
- 239000001361 adipic acid Substances 0.000 claims description 11
- 235000011037 adipic acid Nutrition 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 11
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 10
- 150000002596 lactones Chemical class 0.000 claims description 10
- 125000000732 arylene group Chemical group 0.000 claims description 9
- 239000007788 liquid Substances 0.000 claims description 9
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims description 9
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 claims description 9
- 239000000654 additive Substances 0.000 claims description 8
- 125000002070 alkenylidene group Chemical group 0.000 claims description 8
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 claims description 8
- 239000000049 pigment Substances 0.000 claims description 8
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 claims description 8
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 claims description 8
- 229940114072 12-hydroxystearic acid Drugs 0.000 claims description 7
- 239000004408 titanium dioxide Substances 0.000 claims description 7
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 6
- 239000000945 filler Substances 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 229920005989 resin Polymers 0.000 claims description 6
- 239000011347 resin Substances 0.000 claims description 6
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 claims description 5
- 229960003656 ricinoleic acid Drugs 0.000 claims description 5
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 claims description 5
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 claims description 5
- ZDHCZVWCTKTBRY-UHFFFAOYSA-N 12-hydroxylauric acid Chemical compound OCCCCCCCCCCCC(O)=O ZDHCZVWCTKTBRY-UHFFFAOYSA-N 0.000 claims description 4
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims description 4
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 claims description 4
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 claims description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 4
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 claims description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 4
- 239000000843 powder Substances 0.000 claims description 4
- 239000000377 silicon dioxide Substances 0.000 claims description 4
- XPPKVPWEQAFLFU-UHFFFAOYSA-N diphosphoric acid Chemical compound OP(O)(=O)OP(O)(O)=O XPPKVPWEQAFLFU-UHFFFAOYSA-N 0.000 claims description 3
- 229910044991 metal oxide Inorganic materials 0.000 claims description 3
- 150000004706 metal oxides Chemical class 0.000 claims description 3
- 229920000137 polyphosphoric acid Polymers 0.000 claims description 3
- 229940005657 pyrophosphoric acid Drugs 0.000 claims description 3
- 150000004760 silicates Chemical class 0.000 claims description 3
- 235000012239 silicon dioxide Nutrition 0.000 claims description 3
- LMHJFKYQYDSOQO-SECBINFHSA-N (5r)-5-hydroxydecanoic acid Chemical compound CCCCC[C@@H](O)CCCC(O)=O LMHJFKYQYDSOQO-SECBINFHSA-N 0.000 claims description 2
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 claims description 2
- QQAVZEYXLCYOKO-UHFFFAOYSA-N 4-Hydroxycapric acid Chemical compound CCCCCCC(O)CCC(O)=O QQAVZEYXLCYOKO-UHFFFAOYSA-N 0.000 claims description 2
- PHOJOSOUIAQEDH-UHFFFAOYSA-N 5-hydroxypentanoic acid Chemical compound OCCCCC(O)=O PHOJOSOUIAQEDH-UHFFFAOYSA-N 0.000 claims description 2
- IWHLYPDWHHPVAA-UHFFFAOYSA-N 6-hydroxyhexanoic acid Chemical compound OCCCCCC(O)=O IWHLYPDWHHPVAA-UHFFFAOYSA-N 0.000 claims description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 2
- UWHCKJMYHZGTIT-UHFFFAOYSA-N Tetraethylene glycol, Natural products OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 claims description 2
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 229910045601 alloy Inorganic materials 0.000 claims description 2
- 239000000956 alloy Chemical class 0.000 claims description 2
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims description 2
- VEZXCJBBBCKRPI-UHFFFAOYSA-N beta-propiolactone Chemical compound O=C1CCO1 VEZXCJBBBCKRPI-UHFFFAOYSA-N 0.000 claims description 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims description 2
- 229930188620 butyrolactone Natural products 0.000 claims description 2
- IIRDTKBZINWQAW-UHFFFAOYSA-N hexaethylene glycol Chemical compound OCCOCCOCCOCCOCCOCCO IIRDTKBZINWQAW-UHFFFAOYSA-N 0.000 claims description 2
- LMHJFKYQYDSOQO-UHFFFAOYSA-N hydroxydecanoic acid Natural products CCCCCC(O)CCCC(O)=O LMHJFKYQYDSOQO-UHFFFAOYSA-N 0.000 claims description 2
- 239000004310 lactic acid Substances 0.000 claims description 2
- 235000014655 lactic acid Nutrition 0.000 claims description 2
- 150000002739 metals Chemical class 0.000 claims description 2
- 235000006408 oxalic acid Nutrition 0.000 claims description 2
- 229960000380 propiolactone Drugs 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- LXNOENXQFNYMGT-UHFFFAOYSA-N xi-5-Hydroxydodecanoic acid Chemical compound CCCCCCCC(O)CCCC(O)=O LXNOENXQFNYMGT-UHFFFAOYSA-N 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 29
- 239000011541 reaction mixture Substances 0.000 description 18
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 17
- 239000003973 paint Substances 0.000 description 15
- 239000002609 medium Substances 0.000 description 13
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 9
- 239000002904 solvent Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 7
- 239000008096 xylene Substances 0.000 description 7
- 238000010533 azeotropic distillation Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 229920000180 alkyd Polymers 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 229940125904 compound 1 Drugs 0.000 description 5
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 229940125782 compound 2 Drugs 0.000 description 3
- 229940126214 compound 3 Drugs 0.000 description 3
- 229940125898 compound 5 Drugs 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 230000009974 thixotropic effect Effects 0.000 description 3
- HXVNBWAKAOHACI-UHFFFAOYSA-N 2,4-dimethyl-3-pentanone Chemical compound CC(C)C(=O)C(C)C HXVNBWAKAOHACI-UHFFFAOYSA-N 0.000 description 2
- CCTFMNIEFHGTDU-UHFFFAOYSA-N 3-methoxypropyl acetate Chemical compound COCCCOC(C)=O CCTFMNIEFHGTDU-UHFFFAOYSA-N 0.000 description 2
- FFWSICBKRCICMR-UHFFFAOYSA-N 5-methyl-2-hexanone Chemical compound CC(C)CCC(C)=O FFWSICBKRCICMR-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- 238000004220 aggregation Methods 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 239000002518 antifoaming agent Substances 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000008199 coating composition Substances 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- 239000002612 dispersion medium Substances 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000000976 ink Substances 0.000 description 2
- 239000011256 inorganic filler Substances 0.000 description 2
- 229910003475 inorganic filler Inorganic materials 0.000 description 2
- 239000001023 inorganic pigment Substances 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 150000003014 phosphoric acid esters Chemical class 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- MFEVGQHCNVXMER-UHFFFAOYSA-L 1,3,2$l^{2}-dioxaplumbetan-4-one Chemical compound [Pb+2].[O-]C([O-])=O MFEVGQHCNVXMER-UHFFFAOYSA-L 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- HNAGHMKIPMKKBB-UHFFFAOYSA-N 1-benzylpyrrolidine-3-carboxamide Chemical compound C1C(C(=O)N)CCN1CC1=CC=CC=C1 HNAGHMKIPMKKBB-UHFFFAOYSA-N 0.000 description 1
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 1
- NQBXSWAWVZHKBZ-UHFFFAOYSA-N 2-butoxyethyl acetate Chemical compound CCCCOCCOC(C)=O NQBXSWAWVZHKBZ-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- 229940093475 2-ethoxyethanol Drugs 0.000 description 1
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 1
- VXKUOGVOWWPRNM-UHFFFAOYSA-N 3-ethoxypropyl acetate Chemical compound CCOCCCOC(C)=O VXKUOGVOWWPRNM-UHFFFAOYSA-N 0.000 description 1
- YEHVMOSEQXQFJE-UHFFFAOYSA-N 6-ethoxyhexan-3-ol Chemical compound CCOCCCC(O)CC YEHVMOSEQXQFJE-UHFFFAOYSA-N 0.000 description 1
- ONRLJIQIPPJCSQ-UHFFFAOYSA-N 6-methoxyhexan-3-ol Chemical compound CCC(O)CCCOC ONRLJIQIPPJCSQ-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229920000896 Ethulose Polymers 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- 239000001859 Ethyl hydroxyethyl cellulose Substances 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 229910000003 Lead carbonate Inorganic materials 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 235000019486 Sunflower oil Nutrition 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 229910001297 Zn alloy Inorganic materials 0.000 description 1
- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- LIPOUNRJVLNBCD-UHFFFAOYSA-N acetyl dihydrogen phosphate Chemical compound CC(=O)OP(O)(O)=O LIPOUNRJVLNBCD-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001266 acyl halides Chemical class 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- RREGISFBPQOLTM-UHFFFAOYSA-N alumane;trihydrate Chemical compound O.O.O.[AlH3] RREGISFBPQOLTM-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- AYJRCSIUFZENHW-DEQYMQKBSA-L barium(2+);oxomethanediolate Chemical compound [Ba+2].[O-][14C]([O-])=O AYJRCSIUFZENHW-DEQYMQKBSA-L 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 239000003139 biocide Substances 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
- 229940073609 bismuth oxychloride Drugs 0.000 description 1
- OBNCKNCVKJNDBV-UHFFFAOYSA-N butanoic acid ethyl ester Natural products CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 description 1
- QXDMQSPYEZFLGF-UHFFFAOYSA-L calcium oxalate Chemical compound [Ca+2].[O-]C(=O)C([O-])=O QXDMQSPYEZFLGF-UHFFFAOYSA-L 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- OMAAXMJMHFXYFY-UHFFFAOYSA-L calcium trioxidophosphanium Chemical compound [Ca+2].[O-]P([O-])=O OMAAXMJMHFXYFY-UHFFFAOYSA-L 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 229920003086 cellulose ether Polymers 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- TVZPLCNGKSPOJA-UHFFFAOYSA-N copper zinc Chemical compound [Cu].[Zn] TVZPLCNGKSPOJA-UHFFFAOYSA-N 0.000 description 1
- 229910002026 crystalline silica Inorganic materials 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 125000004956 cyclohexylene group Chemical group 0.000 description 1
- 150000001983 dialkylethers Chemical group 0.000 description 1
- CRHLEZORXKQUEI-UHFFFAOYSA-N dialuminum;cobalt(2+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[Al+3].[Al+3].[Co+2].[Co+2] CRHLEZORXKQUEI-UHFFFAOYSA-N 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 235000019326 ethyl hydroxyethyl cellulose Nutrition 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229910021485 fumed silica Inorganic materials 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 1
- 235000013980 iron oxide Nutrition 0.000 description 1
- VBMVTYDPPZVILR-UHFFFAOYSA-N iron(2+);oxygen(2-) Chemical class [O-2].[Fe+2] VBMVTYDPPZVILR-UHFFFAOYSA-N 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-M isovalerate Chemical compound CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 239000006224 matting agent Substances 0.000 description 1
- 239000002905 metal composite material Substances 0.000 description 1
- NEKSVVBDHNQULT-UHFFFAOYSA-N methyl ethaneperoxoate;propane-1,2-diol Chemical compound CC(O)CO.COOC(C)=O NEKSVVBDHNQULT-UHFFFAOYSA-N 0.000 description 1
- 229940017219 methyl propionate Drugs 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052755 nonmetal Inorganic materials 0.000 description 1
- BWOROQSFKKODDR-UHFFFAOYSA-N oxobismuth;hydrochloride Chemical compound Cl.[Bi]=O BWOROQSFKKODDR-UHFFFAOYSA-N 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 150000003377 silicon compounds Chemical class 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000003017 thermal stabilizer Substances 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- LSGOVYNHVSXFFJ-UHFFFAOYSA-N vanadate(3-) Chemical compound [O-][V]([O-])([O-])=O LSGOVYNHVSXFFJ-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000010456 wollastonite Substances 0.000 description 1
- 229910052882 wollastonite Inorganic materials 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- NDKWCCLKSWNDBG-UHFFFAOYSA-N zinc;dioxido(dioxo)chromium Chemical compound [Zn+2].[O-][Cr]([O-])(=O)=O NDKWCCLKSWNDBG-UHFFFAOYSA-N 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
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/14—Derivatives of phosphoric acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/091—Esters of phosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
Definitions
- the present disclosure relates to a phosphate ester dispersion promoting agent and a process for the preparation thereof.
- the present disclosure also relates to a dispersion of a particulate solid comprising the phosphate ester dispersion promoting agent and use of the phosphate ester dispersion promoting agent for dispersing a particulate solid.
- Particulate solids in particular inorganic particulate solids
- inorganic particulate solids have been widely used in various applications including coatings, adhesives, inks, paints, stains, and so on.
- particulate solids for example, pigments and fillers
- the particulate solids serve to not only provide a good hiding power and a desirable color, but also provide improved physical and chemical properties such as chemical resistance and thermal stability.
- Preferred particulate solids that are used as pigment or filler typically have a relatively small particle size, such as a particle size of micrometers or even nanometers. Using such particulate solids often presents a problem in that the particulate solids are prone to aggregate and difficult to homogenously disperse in a dispersing medium.
- Dispersion aids may be used to improve the dispersibility of particulate solids so as to form a stable dispersion of the particular solids.
- Such dispersion aids typically are cationic, anionic, or non-ionic surface active substances. These substances can be directly applied to the particulate solids, or can be added to a dispersion of the particulate solids.
- the dispersion aids can attach to the surface of the particulate solids, serving to promote dispersion and/or prevent aggregation. It has been known that the dispersion aids suitable for promoting dispersion and/or preventing aggregation of the particulate solids comprise, among others, fat acids, organic silicon compounds, alkanol amines, and polyols.
- the present disclosure provides a dispersion of a particulate solid dispersed with aid of a novel phosphate ester dispersion promoting agent.
- a dispersion of a particulate solid comprising a phosphate ester as a dispersion promoting agent, a particulate solid, a dispersing medium, and optionally one or more additional additives.
- the phosphate ester has the structure of formula (I):
- R independently represents, at each occurrence, a polyester residue containing in its skeleton optionally at least one ether oxygen atom -0-; and x is 1, or 2.
- the polyester residue R has a number-average molecular weight in the range of 200 to 1,500 g/mol. More preferably, the ratio by number of the ether oxygen atom, if present, to carboxylate ester groups -COO- in the skeleton is in the range of 1 : 2 to 3: 1.
- the polyester residue R has the structure represented by formula (1-1) or (1-2):
- each R 1 independently represents, at each occurrence, substituted or
- each R independently represents, at each occurrence, C 2 -Ci 8 alkylene; or -(CH 2 CH 2 0) p CH 2 CH 2 -, in which p is in the range of 1 to 6; or -(CH 2 CH 2 CH 2 0) q CH 2 CH 2 CH 2 -, in which q is in the range of 1 to 6; or
- R" is -CH 2 CH 2 - or -CH 2 CH 2 CH 2 -; m is in the range of 0 to 100; and n is in the range of 0 to 100.
- the dispersion comprises, relative to the total weight of the dispersion of the particulate solid, 0.5 to 3.0% by weight of the phosphate ester as a dispersion promoting agent; 40 to 80%> by weight of the particulate solid; 20 to 40 % by weight of the dispersing medium; and 0 to 10%> by weight of one or more additional additives.
- R independently represents, at each occurrence, a polyester residue containing in its skeleton optionally at least one ether oxygen atom -0-; and x is 1 or 2.
- the process comprising: (i) providing at least one hydroxyl compound containing a free carboxylic acid group represented by the general formula (II)
- the hydroxyl compound is provided by esterification of at least one hydroxycarboxylic acid and/or its lactone, or by esterification of at least one dicarboxylic acid or polycarboxylic acid with at least one diol in a 1 : 1 or greater molar equivalent ratio of the acid to the diol.
- the hydroxyl compound has the structure represented by formula (II- 1) or ( ⁇ -2)
- each R independently represents, at each occurrence, C 2 -Ci 8 alkylene; or -(CH 2 CH 2 0) p CH 2 CH 2 -, in which p is in the range of 1 to 6; or -(CH 2 CH 2 CH 2 0) q CH 2 CH 2 CH 2 -, in which q is in the range of 1 to 6; or
- R" is -CH 2 CH 2 - or -CH 2 CH 2 CH 2 -; m is in the range of 0 to 100; and n is in the range of 0 to 100.
- the particulate solids may comprise pigments or fillers. More preferably, the particulate solids may comprise inorganic pigments or inorganic fillers, such as metals, alloys, metal oxides, metal salts, oxymetallic compounds, nonmetal oxides, or the like.
- the specific examples of such particulate solids may comprise titanium dioxide, calcium carbonate, barium sulfate, silicon dioxide, or silicates.
- the particulate solid may be titanium dioxide, such as titanium dioxide in the form of powder.
- the phosphate ester dispersion promoting agent disclosed herein may contain a polyester residue containing in its skeleton optionally at least one ether oxygen atom -O- and further at least one free carboxylic group.
- the phosphate ester dispersion promoting agent disclosed herein when used for dispersing a particulate solid, can provide the resultant dispersion with a good thixotropic behavior (i.e., a desirable shear-thinning behavior).
- polyester residue refers to a residue derived from a free carboxylic group-containing polyester, which contains in its skeleton optionally at least one ether oxygen atom -0-.
- alkylene refers to a linear, branched, or cyclic divalent saturated hydrocarbyl group that may be substituted or unsubstituted.
- the substituent(s) may preferably include a carboxylic, a carboxylate ester, or a carboxylate salt group.
- Suitable examples of alkylene may include ethylene, propylene, tetramethylene, pentamethylene, 1,3- dimethyltrimethylene, 2,2-dimethyltrimethylene, 3-methylpentamethylene, cyclohexylene, or 1 -isopropyl -2,2-dimethyltrimethylene.
- alkenylidene refers to a linear, branched, or cyclic divalent unsaturated hydrocarbyl group containing at least one carbon-carbon double bond, which may be substituted or unsubstituted.
- the substituent(s) may preferably include a carboxylic, a carboxylate ester, or a carboxylate salt group.
- arylene refers to a divalent aromatic group that may be substituted or unsubstituted.
- the substituent(s) may preferably include a carboxylic, a carboxylate ester, or a carboxylate salt group.
- a suitable example of arylene may include phenylene that may be unsubstituted or substituted with a carboxyl group.
- a molar equivalent ratio of the acid to the diol refers to the molar ratio of carboxylic groups of the dicarboxylic acid or polycarboxylic acid to hydroxyl groups of the diol.
- carboxylic acid as used in the context of esterification with a hydroxyl compound, also includes any suitable ester-forming derivative thereof, which can react with a hydroxyl compound to form a carboxylate ester.
- the suitable ester-forming derivative of a carboxylic acid is known to a person skilled in the art, and may include, but not limited to, an anhydride, an acyl halide, an ester of a carboxylic acid and a lower alkanol, or the like.
- compositions are described as having, including, or comprising specific components or fractions, or where processes are described as having, including, or comprising specific process steps, it is contemplated that the compositions or processes as disclosed herein may further comprise other components or fractions or steps, whether or not specifically mentioned in this disclosure, as long as such components or steps do not affect the basic and novel characteristics of the invention, but it is also contemplated that the compositions or processes may consist essentially of, or consist of, the recited components or steps.
- a As used herein, "a”, “an”, “the”, “at least one”, and “one or more” are used interchangeably. Thus, for example, a dispersion that comprises “a” particulate solid can be interpreted to mean that the dispersion includes “one or more” particulate solids.
- ranges from any lower limit may be combined with any upper limit to recite a range not explicitly recited
- ranges from any lower limit may be combined with any other lower limit to recite a range not explicitly recited
- ranges from any upper limit may be combined with any other upper limit to recite a range not explicitly recited.
- within a range includes every point or individual value between its end points even though not explicitly recited. Thus, every point or individual value may serve as its own lower or upper limit combined with any other point or individual value or any other lower or upper limit, to recite a range not explicitly recited.
- a phosphate ester having formula (I) used as a dispersion promoting agent is provided.
- the polyester residue R independently represents, at each occurrence, a polyester residue containing in its skeleton optionally at least one ether oxygen atom -0-; and x is 1 or 2.
- the polyester residue R has a number-average molecular weight in the range of 200 to 1 ,500 g/mol, more preferably 500 to 1,400 g/mol, and even more preferably 700 to 1 ,200 g/mol.
- the ratio by number of the ether oxygen atom to carboxylate ester groups -COO- in the skeleton is in the range of 1 :2 to 3 : 1. Preferably, the ratio is about 1 : 1.
- the polyester residue R that contains in its skeleton optionally at least one ether oxygen atom -O- has the structure represented by formula (I-l) or (1-2):
- each R 1 independently represents, at each occurrence, substituted or unsubstituted C 2 - Ci 8 alkylene, substituted or unsubstituted C 2 -Ci 8 alkenylidene, or substituted or
- each R independently represents, at each occurrence, C 2 -Ci 8 alkylene
- n is in the range of 0 to 100.
- R independently represents, at each occurrence, a polyester residue containing in its skeleton optionally at least one ether oxygen atom -0-;
- x 1 or 2
- R is defined as above;
- phosphating agent refers to a phosphorus compound which can form a phosphate ester by reaction with a hydroxyl compound.
- phosphorus oxychloride, phosphorus pentoxide, polyphosphoric acid, pyrophosphoric acid or acetyl phosphate can be used as an example of a phosphating agent. Additional examples can be found in German Patent Application No. DE-A 2,726,854. Phosphorus pentoxide, polyphosphoric acid and pyrophosphoric acid are preferred.
- the phosphate ester as disclosed herein can be prepared by reaction of one phosphoric acid equivalent of a phosphating agent with one or two equivalents of a hydroxyl compound represented by the general formula (II) as defined above.
- the reaction can be carried out as described, for example, in US Patent No.
- one phosphoric acid equivalent means that the phosphating agent can react with one or two equivalents of a hydroxyl compound represented by the general formula (II) stoichiometrically to form a phosphoric acid monoester or diester represented by the general formula (I) as indicated above.
- a phosphoric acid monoester is expected to form stoichiometrically.
- a phosphoric acid diester is expected to form stoichiometrically.
- Intermediate ratios i.e., between one and two equivalents of hydroxyl compound
- a mixture of monoester and diester species will be formed.
- polyester residues R's in a phosphate ester of formula (I) may be the same or different.
- a phosphate ester of formula (I) having different polyester residues R's can be prepared, for example, by first reacting 1 phosphoric acid equivalent of a phosphating agent with 1 equivalent of a hydroxyl compound to form a monoester, then reacting the resulting monoester with 1 equivalent of a hydroxyl compound having a different polyester residue R.
- a phosphate ester of formula (I) having different polyester residues R's can also be prepared by reacting 1 phosphoric acid equivalent of a phosphating agent with a mixture of hydroxyl compounds having different polyester residues R's.
- a person skilled in the art can determine the suitable conditions for the reaction of a phosphating agent with a hydroxyl compound according to the types of phosphating agent and hydroxyl compound used, including use of solvent, reaction temperature, and so on.
- the reaction is carried out at a temperature of at most 100 °C in absence of any solvent.
- the reaction can be carried out in presence of a suitable inert solvent as described in, for example, EP-A 193019.
- providing the hydroxyl compound containing a free carboxylic acid group comprises providing a hydroxyl compound containing a free carboxylic acid group having the structure represented by formula (II- 1) or ( ⁇ -2) by esterification of at least one hydroxycarboxylic acid and/or its lactone, or by esterification of at least one dicarboxylic acid or polycarboxylic acid with at least one diol in a 1 : 1 or greater molar equivalent ratio of the acid to the diol:
- the hydroxyl compound has a number-average molecular weight in the range of 200 to 1,500 g/mol, more preferably 500 to 1,400 g/mol, and even more preferably 700 to 1 ,200 g/mol.
- the number-average molecular weight can be determined by an acid value of the hydroxyl compound.
- hydroxycarboxylic acid and/or its lactone may be used as the starting material.
- Suitable hydroxycarboxylic acids include: 12-hydroxystearic acid, ricinoleic acid, 12-hydroxydodecanoic acid, 5-hydroxydodecanoic acid, 5-hydroxydecanoic acid, 4- hydroxydecanoic acid, glycolic acid, lactic acid, 6-hydroxyhexanoic acid and 5- hydroxypentanoic acid.
- ricinoleic acid or 12-hydroxystearic acid are used as the hydroxycarboxylic acid.
- Suitable lactones include: propiolactone, butyro lactone, ⁇ -valerolactone, ⁇ - caprolactone, and Ci_g alkyl substituted ⁇ -caprolactone.
- ⁇ -caprolactone is used as the lactone.
- the esterification reaction of hydroxycarboxylic acid and/or its lactone can be effected under conditions that are known in the art.
- the esterification reaction can be effected in the presence of a catalyst such as p-toluenesulfonic acid, dibutyltin dilaurate or tetrabutyl titanate at a temperature ranging from about 80 °C to about 180 °C.
- the esterification reaction of 12-hydroxystearic acid as the hydroxycarboxylic acid and ⁇ -caprolactone as the lactone is carried out in the presence of a catalyst at an elevated temperature.
- a catalyst for example, 12-hydroxystearic acid and ⁇ - caprolactone may be used as the starting materials and provided in a 1 : 1 molar equivalent ratio of carboxyl group to hydroxyl group for the esterification, thereby forming a hydroxyl compound containing a free carboxylic acid group.
- each R independently represents, at each occurrence
- the reaction is carried out in a solvent of xylene in the presence of a catalyst of tetrabutyl titanate at an elevated temperature up to 180 °C. Water is removed from the reaction system while the reaction is proceeding.
- dicarboxylic acid or polycarboxylic acid and diol may be used as the starting material.
- the molar equivalent ratio of dicarboxylic acid or polycarboxylic acid to diol is 1 : 1 or greater.
- the molar equivalent ratio of dicarboxylic acid or polycarboxylic acid to diol is in the range of 1 : 1 to 1.2: 1.
- Dicarboxylic acid or polycarboxylic acid can also be used in the form of its ester-forming derivative.
- the acid is used in the form of anhydride.
- trimellitic anhydride (TMA) or 4-carboxyl phthalic anhydride can be used.
- TMA trimellitic anhydride
- 4-carboxyl phthalic anhydride can be used.
- oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, sebacic acid, trimellitic anhydride, or combination thereof can be given.
- adipic acid, sebacic acid, trimellitic anhydride or combination thereof is used.
- Suitable diols used herein include, neopentyl glycol, 1,6-hexylene glycol, 3- methyl-l,5-pentanediol, 1,4-cyclohexane dimethanol, 2,2,4-trimethyl-l,3-pentanediol, ethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, hexaethylene glycol, propylene glycol, tripropylene glycol, or combination thereof.
- neopentyl glycol, 1,6-hexylene glycol, triethylene glycol, tripropylene glycol, or a combination thereof is used. More preferably, triethylene glycol or tripropylene glycol is used.
- the esterification reaction of dicarboxylic acid or polycarboxylic acid (or its ester- forming derivative) with diol can be effected under the conditions that are known in the art.
- the esterification reaction can be effected by removing water under azeotropic distillation in the absence of any catalyst.
- adipic acid is used as the dicarboxylic acid, and neopentyl glycol and 1,6-hexylene glycol are used as the diol.
- the esterification reaction of adipic acid with neopentyl glycol and 1,6-hexylene glycol is effected by removing water under azeotropic distillation at an elevated temperature.
- Adipic acid used as the dicarboxylic acid and neopentyl glycol and 1,6-hexylene glycol used as the diol are loaded, respectively, in such an amount that the molar equivalent ratio of the dicarboxylic acid to the diol is in the range of 1 : 1 to 1.2: 1 , in particular 1 : 1, thereby forming a hydroxyl compound containing a free carboxylic acid group.
- each Pv 1 independently represents, at each occurrence, -(CH 2 )4-;
- each R independently represents, at each occurrence, -CH 2 C(CH 3 ) 2 CH 2 - or -(CH 2 ) 6 -;
- n is in the range of 0 to 100.
- the reaction is carried out in a solvent of xylene in the absence of any catalyst at an elevated temperature up to 160 °C. Water is removed from the reaction system while the reaction is proceeding.
- the phosphate ester dispersion promoting agent according to the present disclosure can be prepared by the process as disclosed herein.
- the phosphate ester dispersion promoting agent as prepared can be applied directly to intended applications, such as formulation of stain or paint.
- a dispersion of a particulate solid comprising the phosphate ester dispersion promoting agent as disclosed herein and use of the phosphate ester dispersion promoting agent for dispersing a particulate solid.
- a dispersion of a particulate solid refers to a composition of matter obtained by dispersing a particulate solid in a dispersing medium with the aid of a dispersion promoting agent.
- a dispersion of a particulate solid comprises a phosphate ester dispersion promoting agent as disclosed herein, a particulate solid, a dispersing medium, and optionally one or more additional additives.
- the dispersion may comprise, relative to the total weight of the dispersion, 0.5 to 3.0% by weight, preferably 0.5 to 2.0 % by weight, more preferably 0.7 to 1.5 % by weight, and most preferably 0.8 to 1.0 % by weight, of the phosphate ester dispersion promoting agent.
- particulate solid refers to any solid material which is substantially insoluble in a dispersion medium at the temperature concerned, and which it is desired to stabilize in a finely divided form in the dispersion medium.
- the particulate solid may be in shape of sphere, fiber, flake, or other regular or irregular shapes of micrometric or even nanometric size.
- Examples of a particulate solid comprise pigments and fillers, especially those pigments or fillers suitably used in a stain, paint or coating.
- the particulate solid is selected from inorganic pigments comprising metal oxides such as titanium dioxide, iron oxides, zinc oxide, zirconia, or aluminia; metal composite oxides containing two or more metal elements including manganese, nickel, titanium, chromium, antimony, magnesium, cobalt, iron, or aluminum; oxymetallic compounds, such as bismuth vanadate, cobalt aluminate, cobalt zincate, or zinc chromate; metallic pigments, such as aluminum flake, copper, and copper-zinc alloys; and pearlescent pigments, such as lead carbonate and bismuth oxychloride.
- metal oxides such as titanium dioxide, iron oxides, zinc oxide, zirconia, or aluminia
- oxymetallic compounds such as bismuth vanadate, cobalt aluminate, cobalt zincate,
- the particulate solid is selected from the group of inorganic fillers comprising calcium carbonate, calcium sulfate, calcium oxide, calcium oxalate, calcium phosphate, calcium phosphonate, barium sulfate, barium carbonate, magnesium oxide, magnesium hydroxide, aluminum trihydrate, silica (including natural amorphous silica, natural crystalline silica, natural diatomaceous earth, precipitated silica, fumed silica and nano-silica), silicates (including talc, kaolin, wollastonite, mica, sericite, synthetic aluminum silicate), metal fibers, glass fibers, carbon black, and the like.
- silica including natural amorphous silica, natural crystalline silica, natural diatomaceous earth, precipitated silica, fumed silica and nano-silica
- silicates including talc, kaolin, wollastonite, mica, sericite, synthetic aluminum silicate
- the particulate solid is titanium dioxide in the form of a powder.
- the dispersion may comprise, relative to the total weight of the dispersion, 40 to 80 % by weight, preferably 50 to 80 % by weight, more preferably 55 to 70 % by weight, and most preferably 55 to 65 % by weight, of the particulate solid.
- the term "dispersing medium” refers to a medium in which the particulate solid is dispersed.
- the dispersing medium is a polar organic liquid or resin or a non-polar organic liquid.
- Suitable examples of the polar organic liquid include, but are not limited to, dialkyl ketones, alkyl esters of alkanoic acid and alkanol, and the like.
- dialkyl and cycloalkyl ketones such as acetone, methyl ethyl ketone, diethyl ketone, di- isopropyl ketone, methyl isobutyl ketone, di-isobutyl ketone, methyl isoamyl ketone, methyl n-amyl ketone and cyclohexanone; alkyl esters, such as methyl acetate, ethyl acetate, isopropyl acetate, butyl acetate, ethyl formate, methyl propionate, methoxy propylacetate, and ethyl butyrate; glycols and glycol esters and ethers, such as ethylene glycol, 2-ethoxyethanol, 3-methoxypropylpropanol, 3-ethoxypropylpropanol, 2- butoxyethyl acetate, 3-methoxypropyl
- a polar resin may also be used as the dispersing medium of the dispersion according to the present disclosure. Suitable examples thereof are those film-formation resins suitably used in inks, paints or coatings.
- the specific examples of such resins include, among others, polyamides, such as VersamidTM and WolfamidTM; cellulose ethers, such as ethyl cellulose and ethyl hydroxyethyl cellulose; and alkyd resins, such as short oil alkyd resins and long oil alkyd resins.
- non-polar, organic liquid examples include, among others, non- halogenated aromatic hydrocarbons, such as toluene and xylene; halogenated aromatic hydrocarbons, such as chlorobenzene, dichlorobenzene and trichlorobenzene; non- halogenated aliphatic hydrocarbons, such as those saturated or partially saturated, linear or branched hydrocarbons containing 6 or more carbon atoms; halogenated aliphatic hydrocarbons, such as dichloromethane, carbon tetrachloride, chloroform, trichloroethane; and natural non-polar organic liquids, such as vegetable oils, sunflower oil, linseed oil, terpene, and glyceride.
- non- halogenated aromatic hydrocarbons such as toluene and xylene
- halogenated aromatic hydrocarbons such as chlorobenzene, dichlorobenzene and trichlorobenzene
- a polar organic liquid or a polar resin is used as the dispersing medium.
- the phosphate ester dispersion promoting agent according to the present disclosure will have good compatibility with the dispersing medium, thereby allowing the particulate solid to disperse in the dispersing medium even better.
- the dispersion may comprise, relative to the total weight of the dispersion, 20 to 40 % by weight, preferably 25 to 35 % by weight, of the dispersing medium.
- the dispersion of a particulate solid may further comprise one or more additional additives.
- additional additives comprise surface active agents, antifoaming agents, rheology modifying agents, thermal stabilizers, flow/leveling agents, matting agents, anti-sedimentation agents, biocides, and combination thereof.
- the amounts and types of additional additives desirably used can be determined empirically by a person skilled in the art.
- the total amount of one or more additives is in the range of 0 to 10 % by weight relative to the total weight of the dispersion.
- the dispersion of a particulate solid as disclosed herein can be used directly as such or can be used to formulate paints or coating compositions.
- Hydroxyl Compound 2 was prepared according to the similar procedure for the preparation of Hydroxyl Compound 1, except that 59.08 parts of 3-methyl-l,5-pentanediol was used to replace hexane glycol, and the reaction was stopped when the acid value arrived at about 59.1 mg KOH/g reaction mixture. Hydroxyl Compound 2 that contains a free carboxylic acid group was obtained. After calculation, its number-average molecular weight was determined to be about 850 g/mol. Hydroxyl Compound 3
- Hydroxyl Compound 3 was prepared according to the similar procedure for the preparation of Hydroxyl Compound 1, except that 202.25 parts of sebacic acid were used to replace adipic acid, and the reaction was stopped when the acid value arrived about 69 mg KOH/g reaction mixture. Hydroxyl Compound 3 that contains a free carboxylic acid group was obtained. After calculation, its number-average molecular weight was determined to be about 730 g/mol.
- Hydroxyl Compound 6 was prepared according to the similar procedure for the preparation of Hydroxyl Compound 5, except that 300.48 parts of 12-hydroxystearic acid was used to replace ricinoleic acid, and the reaction was stopped when the acid value arrived about 45 mg KOH/g reaction mixture. Hydroxyl Compound 6 that contains a free carboxylic acid group was obtained. After calculation, its number-average molecular weight was determined to be about 1120 g/mol.
- Phosphate Esters 2-10 were prepared according to the similar procedure for the preparation of Phosphate Ester 1, except that the hydroxyl compounds and the phosphating agents were used as listed in Table 1.
- Phosphate ester dispersion promoting agents 2, 4, and 6 50 solids%) prepared in Example 1 were mixed with short oil alkyd resin (60 solids%), titanium dioxide powder and propylene glycol methoxy acetate (PGMA), respectively, in amounts as shown in Table 2, and were dispersed in Dispermat with glass beads for 1 hour, thus providing the dispersions of a particulate solid named Dispersion 2, Dispersion 4, and Dispersion 6. Additionally, the conventional phosphate ester dispersion promoting agent commercially available under the trade name BYK110 (50 solids%) was used to formulate a control dispersion with the ingredients according to Table 2.
- PGMA propylene glycol methoxy acetate
- Dispersions 2, 4, and 6 produced in Example 2 were mixed, as a stain, with short oil alkyd resin (60 solids%), butyl acetate, and the antifoaming agent, respectively, in amounts as shown in Table 3 in a high-speed disperser at 2000 rpm, thus providing the paints named Paint 2, Paint 4, and Paint 6. Additionally, the control dispersion was used to formulate a control paint with the ingredients according to Table 3.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Biochemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Pigments, Carbon Blacks, Or Wood Stains (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Paints Or Removers (AREA)
Abstract
Description
Claims
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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CN201310233774.4A CN104231673B (en) | 2013-06-13 | 2013-06-13 | Phosphoric acid ester dispersing auxiliary and comprise the dispersion of this phosphoric acid ester dispersing auxiliary |
PCT/US2014/040605 WO2014200755A1 (en) | 2013-06-13 | 2014-06-03 | Phosphate ester dispersion promoting agent and dispersion comprising the same |
Publications (2)
Publication Number | Publication Date |
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EP3007813A1 true EP3007813A1 (en) | 2016-04-20 |
EP3007813A4 EP3007813A4 (en) | 2017-04-19 |
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Application Number | Title | Priority Date | Filing Date |
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EP14810305.4A Withdrawn EP3007813A4 (en) | 2013-06-13 | 2014-06-03 | Phosphate ester dispersion promoting agent and dispersion comprising the same |
Country Status (3)
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EP (1) | EP3007813A4 (en) |
CN (1) | CN104231673B (en) |
WO (1) | WO2014200755A1 (en) |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
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DE2726854A1 (en) * | 1977-06-15 | 1979-01-11 | Bayer Ag | PHOSPHORIC ACID ESTER |
JPS61194091A (en) * | 1985-02-21 | 1986-08-28 | Dainichi Seika Kogyo Kk | Phosphoric acid ester |
GB9609436D0 (en) * | 1996-05-04 | 1996-07-10 | Zeneca Ltd | Composition and use |
GB9809116D0 (en) * | 1998-04-29 | 1998-07-01 | Zeneca Ltd | Ether/ester dispersants |
GB0109708D0 (en) * | 2001-04-20 | 2001-06-13 | Avecia Ltd | Dispersants |
CN101096387A (en) * | 2006-06-30 | 2008-01-02 | 戈尔德施米特股份公司 | Phosphate and usage as dispersant thereof |
CN101045828A (en) * | 2006-07-03 | 2007-10-03 | 张义纲 | Phosphate film-coated powder and preparation method thereof |
CN102604485B (en) * | 2012-03-05 | 2014-12-17 | 苏州世名科技股份有限公司 | Pigment dispersing agent composite containing phosphate ester structure and preparation method thereof |
-
2013
- 2013-06-13 CN CN201310233774.4A patent/CN104231673B/en active Active
-
2014
- 2014-06-03 WO PCT/US2014/040605 patent/WO2014200755A1/en active Application Filing
- 2014-06-03 EP EP14810305.4A patent/EP3007813A4/en not_active Withdrawn
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CN104231673B (en) | 2016-01-13 |
WO2014200755A1 (en) | 2014-12-18 |
EP3007813A4 (en) | 2017-04-19 |
CN104231673A (en) | 2014-12-24 |
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