FR2939055A1 - Use of a mineral material, homopolymer or copolymer of acrylic acid, as dispersing agent and/or grinding aid agent, where the acrylic acid is obtained from glycerol - Google Patents
Use of a mineral material, homopolymer or copolymer of acrylic acid, as dispersing agent and/or grinding aid agent, where the acrylic acid is obtained from glycerol Download PDFInfo
- Publication number
- FR2939055A1 FR2939055A1 FR0858219A FR0858219A FR2939055A1 FR 2939055 A1 FR2939055 A1 FR 2939055A1 FR 0858219 A FR0858219 A FR 0858219A FR 0858219 A FR0858219 A FR 0858219A FR 2939055 A1 FR2939055 A1 FR 2939055A1
- Authority
- FR
- France
- Prior art keywords
- acrylic acid
- acid
- monomer
- use according
- chosen
- 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.)
- Pending
Links
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 title claims abstract description 44
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 title claims abstract description 43
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 title claims abstract description 35
- 229910052500 inorganic mineral Inorganic materials 0.000 title claims abstract description 20
- 239000011707 mineral Substances 0.000 title claims abstract description 20
- 238000000227 grinding Methods 0.000 title claims abstract description 17
- 229920001577 copolymer Polymers 0.000 title claims abstract description 16
- 229920001519 homopolymer Polymers 0.000 title claims abstract description 16
- 239000003795 chemical substances by application Substances 0.000 title claims abstract description 13
- 239000000463 material Substances 0.000 title claims abstract description 11
- 239000002270 dispersing agent Substances 0.000 title claims abstract description 8
- 239000000178 monomer Substances 0.000 claims description 47
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 18
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 16
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- -1 nitroxides Chemical class 0.000 claims description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- 235000011130 ammonium sulphate Nutrition 0.000 claims description 6
- 238000006297 dehydration reaction Methods 0.000 claims description 6
- 238000006116 polymerization reaction Methods 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- 238000010526 radical polymerization reaction Methods 0.000 claims description 6
- 229910021653 sulphate ion Inorganic materials 0.000 claims description 6
- 239000000725 suspension Substances 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 239000011575 calcium Substances 0.000 claims description 5
- 229910052791 calcium Inorganic materials 0.000 claims description 5
- 125000002091 cationic group Chemical group 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- 239000005995 Aluminium silicate Substances 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 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 claims description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- MXRIRQGCELJRSN-UHFFFAOYSA-N O.O.O.[Al] Chemical compound O.O.O.[Al] MXRIRQGCELJRSN-UHFFFAOYSA-N 0.000 claims description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000001166 ammonium sulphate Substances 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 150000004679 hydroxides Chemical class 0.000 claims description 4
- 125000005395 methacrylic acid group Chemical group 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 238000012546 transfer Methods 0.000 claims description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
- 229920002554 vinyl polymer Polymers 0.000 claims description 4
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000000524 functional group Chemical group 0.000 claims description 3
- LVHBHZANLOWSRM-UHFFFAOYSA-N itaconic acid Chemical class OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 3
- 238000006386 neutralization reaction Methods 0.000 claims description 3
- 239000000454 talc Substances 0.000 claims description 3
- 229910052623 talc Inorganic materials 0.000 claims description 3
- OUEBZMGRFLTABC-UHFFFAOYSA-N 2-methyl-1-(prop-2-enoylamino)propane-2-sulfonic acid Chemical compound OS(=O)(=O)C(C)(C)CNC(=O)C=C OUEBZMGRFLTABC-UHFFFAOYSA-N 0.000 claims description 2
- AGBXYHCHUYARJY-UHFFFAOYSA-N 2-phenylethenesulfonic acid Chemical compound OS(=O)(=O)C=CC1=CC=CC=C1 AGBXYHCHUYARJY-UHFFFAOYSA-N 0.000 claims description 2
- SEILKFZTLVMHRR-UHFFFAOYSA-N 2-phosphonooxyethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOP(O)(O)=O SEILKFZTLVMHRR-UHFFFAOYSA-N 0.000 claims description 2
- UDXXYUDJOHIIDZ-UHFFFAOYSA-N 2-phosphonooxyethyl prop-2-enoate Chemical compound OP(O)(=O)OCCOC(=O)C=C UDXXYUDJOHIIDZ-UHFFFAOYSA-N 0.000 claims description 2
- BRWBXCPVJZQRHJ-UHFFFAOYSA-N 2-phosphonooxypropyl 2-methylprop-2-enoate Chemical compound OP(=O)(O)OC(C)COC(=O)C(C)=C BRWBXCPVJZQRHJ-UHFFFAOYSA-N 0.000 claims description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 2
- GDFCSMCGLZFNFY-UHFFFAOYSA-N Dimethylaminopropyl Methacrylamide Chemical compound CN(C)CCCNC(=O)C(C)=C GDFCSMCGLZFNFY-UHFFFAOYSA-N 0.000 claims description 2
- 239000012988 Dithioester Substances 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 2
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 125000005250 alkyl acrylate group Chemical group 0.000 claims description 2
- 125000000746 allylic group Chemical group 0.000 claims description 2
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims description 2
- 235000012211 aluminium silicate Nutrition 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 claims description 2
- 150000004657 carbamic acid derivatives Chemical class 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000006229 carbon black Substances 0.000 claims description 2
- 239000003575 carbonaceous material Substances 0.000 claims description 2
- 230000003197 catalytic effect Effects 0.000 claims description 2
- 235000013985 cinnamic acid Nutrition 0.000 claims description 2
- WBYWAXJHAXSJNI-UHFFFAOYSA-N cinnamic acid group Chemical class C(C=CC1=CC=CC=C1)(=O)O WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 claims description 2
- 238000007334 copolymerization reaction Methods 0.000 claims description 2
- GQOKIYDTHHZSCJ-UHFFFAOYSA-M dimethyl-bis(prop-2-enyl)azanium;chloride Chemical compound [Cl-].C=CC[N+](C)(C)CC=C GQOKIYDTHHZSCJ-UHFFFAOYSA-M 0.000 claims description 2
- 125000005022 dithioester group Chemical group 0.000 claims description 2
- 239000000839 emulsion Substances 0.000 claims description 2
- BNKAXGCRDYRABM-UHFFFAOYSA-N ethenyl dihydrogen phosphate Chemical compound OP(O)(=O)OC=C BNKAXGCRDYRABM-UHFFFAOYSA-N 0.000 claims description 2
- DOEXKUOGPAEBAD-UHFFFAOYSA-N ethyl n-(2-methylprop-2-enoyl)carbamate Chemical compound CCOC(=O)NC(=O)C(C)=C DOEXKUOGPAEBAD-UHFFFAOYSA-N 0.000 claims description 2
- 239000000835 fiber Substances 0.000 claims description 2
- 239000000945 filler Substances 0.000 claims description 2
- 239000010440 gypsum Substances 0.000 claims description 2
- 229910052602 gypsum Inorganic materials 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 150000003949 imides Chemical class 0.000 claims description 2
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 claims description 2
- 239000011777 magnesium Substances 0.000 claims description 2
- 229910052749 magnesium Inorganic materials 0.000 claims description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 2
- 150000002734 metacrylic acid derivatives Chemical class 0.000 claims description 2
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims description 2
- 125000005394 methallyl group Chemical group 0.000 claims description 2
- 239000010445 mica Substances 0.000 claims description 2
- 229910052618 mica group Inorganic materials 0.000 claims description 2
- ADTJPOBHAXXXFS-UHFFFAOYSA-N n-[3-(dimethylamino)propyl]prop-2-enamide Chemical compound CN(C)CCCNC(=O)C=C ADTJPOBHAXXXFS-UHFFFAOYSA-N 0.000 claims description 2
- 239000002798 polar solvent Substances 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 238000001556 precipitation Methods 0.000 claims description 2
- OCAAZRFBJBEVPS-UHFFFAOYSA-N prop-2-enyl carbamate Chemical compound NC(=O)OCC=C OCAAZRFBJBEVPS-UHFFFAOYSA-N 0.000 claims description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 230000003068 static effect Effects 0.000 claims description 2
- 150000003463 sulfur Chemical class 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- 239000004408 titanium dioxide Substances 0.000 claims description 2
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 claims description 2
- RRHXZLALVWBDKH-UHFFFAOYSA-M trimethyl-[2-(2-methylprop-2-enoyloxy)ethyl]azanium;chloride Chemical compound [Cl-].CC(=C)C(=O)OCC[N+](C)(C)C RRHXZLALVWBDKH-UHFFFAOYSA-M 0.000 claims description 2
- OEIXGLMQZVLOQX-UHFFFAOYSA-N trimethyl-[3-(prop-2-enoylamino)propyl]azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CCCNC(=O)C=C OEIXGLMQZVLOQX-UHFFFAOYSA-N 0.000 claims description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 2
- 239000012989 trithiocarbonate Substances 0.000 claims description 2
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 claims description 2
- 239000012991 xanthate Substances 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 2
- QISOBCMNUJQOJU-UHFFFAOYSA-N 4-bromo-1h-pyrazole-5-carboxylic acid Chemical compound OC(=O)C=1NN=CC=1Br QISOBCMNUJQOJU-UHFFFAOYSA-N 0.000 claims 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims 1
- 239000000159 acid neutralizing agent Substances 0.000 claims 1
- 150000001244 carboxylic acid anhydrides Chemical group 0.000 claims 1
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 claims 1
- 229940018557 citraconic acid Drugs 0.000 claims 1
- IPZIVCLZBFDXTA-UHFFFAOYSA-N ethyl n-prop-2-enoylcarbamate Chemical compound CCOC(=O)NC(=O)C=C IPZIVCLZBFDXTA-UHFFFAOYSA-N 0.000 claims 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 1
- HNEGQIOMVPPMNR-NSCUHMNNSA-N mesaconic acid Chemical compound OC(=O)C(/C)=C/C(O)=O HNEGQIOMVPPMNR-NSCUHMNNSA-N 0.000 claims 1
- JAMKSFBTGLCRNL-UHFFFAOYSA-N phosphoric acid;prop-1-ene;prop-2-enoic acid Chemical compound CC=C.OC(=O)C=C.OP(O)(O)=O JAMKSFBTGLCRNL-UHFFFAOYSA-N 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- GYLZSBPASSUYIS-UHFFFAOYSA-N tert-butyl n-benzyl-n-prop-1-en-2-ylcarbamate Chemical compound CC(C)(C)OC(=O)N(C(=C)C)CC1=CC=CC=C1 GYLZSBPASSUYIS-UHFFFAOYSA-N 0.000 claims 1
- AIUAMYPYEUQVEM-UHFFFAOYSA-N trimethyl(2-prop-2-enoyloxyethyl)azanium Chemical compound C[N+](C)(C)CCOC(=O)C=C AIUAMYPYEUQVEM-UHFFFAOYSA-N 0.000 claims 1
- ZTWTYVWXUKTLCP-UHFFFAOYSA-N vinylphosphonic acid Chemical compound OP(O)(=O)C=C ZTWTYVWXUKTLCP-UHFFFAOYSA-N 0.000 claims 1
- 235000011187 glycerol Nutrition 0.000 description 11
- 229920002125 Sokalan® Polymers 0.000 description 8
- 239000004584 polyacrylic acid Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 230000018044 dehydration Effects 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 239000002994 raw material Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 235000011941 Tilia x europaea Nutrition 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 239000004568 cement Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000004571 lime Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- ZWJWOOXWVLIPPX-UHFFFAOYSA-N 2-phosphonooxypropyl prop-2-enoate Chemical compound OP(=O)(O)OC(C)COC(=O)C=C ZWJWOOXWVLIPPX-UHFFFAOYSA-N 0.000 description 1
- 239000002028 Biomass Substances 0.000 description 1
- 229910021532 Calcite Inorganic materials 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 239000004165 Methyl ester of fatty acids Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000002730 additional effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000008064 anhydrides Chemical group 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000009837 dry grinding Methods 0.000 description 1
- 235000019387 fatty acid methyl ester Nutrition 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000002803 fossil fuel Substances 0.000 description 1
- 238000013467 fragmentation Methods 0.000 description 1
- 238000006062 fragmentation reaction Methods 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000006140 methanolysis reaction Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- UZNHKBFIBYXPDV-UHFFFAOYSA-N trimethyl-[3-(2-methylprop-2-enoylamino)propyl]azanium;chloride Chemical compound [Cl-].CC(=C)C(=O)NCCC[N+](C)(C)C UZNHKBFIBYXPDV-UHFFFAOYSA-N 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 125000002348 vinylic group Chemical group 0.000 description 1
- 239000012855 volatile organic compound Substances 0.000 description 1
- 238000001238 wet grinding Methods 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B02—CRUSHING, PULVERISING, OR DISINTEGRATING; PREPARATORY TREATMENT OF GRAIN FOR MILLING
- B02C—CRUSHING, PULVERISING, OR DISINTEGRATING IN GENERAL; MILLING GRAIN
- B02C23/00—Auxiliary methods or auxiliary devices or accessories specially adapted for crushing or disintegrating not provided for in preceding groups or not specially adapted to apparatus covered by a single preceding group
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Abstract
Description
UTILISATION DE POLYMERES ACRYLIQUES DONT L'ACIDE ACRYLIQUE EST ISSU DU GLYCEROL, COMME AGENT DE DISPERSION OU DE BROYAGE DE MATIERES MINERALES Proposer des produits dont la synthèse ne repose plus sur des matières premières issues d'une énergie fossile, est aujourd'hui un enjeu majeur pour l'industrie chimique. Cette démarche s'inscrit dans la réduction du taux de composés organiques volatils telle que définie par le protocole de Kyoto, et de manière plus générale dans les concepts de "chimie verte" et de "développement durable". USE OF ACRYLIC ACRYLIC ACRYLIC POLYMERS FROM GLYCEROL, AS A DISPERSION OR MILLING AGENT OF MINERAL MATERIALS Offering products whose synthesis no longer rests on raw materials derived from fossil fuels, is now an issue major for the chemical industry. This approach is part of the reduction of volatile organic compounds as defined by the Kyoto Protocol, and more generally in the concepts of "green chemistry" and "sustainable development".
L'industrie minéralière est une grande consommatrice de produits chimiques. Ceux-ci sont utilisés dans les différentes étapes de transformation/modification/traitement que subissent les matières minérales. Ainsi, dans le cas du carbonate de calcium d'origine naturelle ou synthétique, l'homme du métier réalise de nombreuses opérations dites de "broyage" (réduction de la taille granulométrique des particules) à sec ou en milieu humide, ou de "dispersion" (mise en suspension des particules dans un liquide). The mineral industry is a big consumer of chemicals. These are used in the various stages of transformation / modification / treatment that the mineral materials undergo. Thus, in the case of calcium carbonate of natural or synthetic origin, those skilled in the art carry out numerous operations known as "grinding" (reduction of the particle size size) in dry or in a humid medium, or "dispersion" "(suspending the particles in a liquid).
Ces deux opérations sont rendues plus aisées par la mise en oeuvre respectivement d'agents d'aide au broyage, dont le rôle est de faciliter l'action mécanique d'attrition et de fragmentation des particules, et d'agent dispersants, dont la fonction consiste à maintenir la viscosité de la suspension dans des plages acceptables au fur et à mesure qu'on y introduit les matières minérales. These two operations are made easier by the implementation respectively of grinding aid agents, whose role is to facilitate the mechanical action of attrition and fragmentation of the particles, and dispersing agent, whose function It consists in maintaining the viscosity of the suspension in acceptable ranges as the mineral substances are introduced therein.
L'art antérieur est particulièrement riche au sujet de tels additifs. Depuis de nombreuses années, on sait que les homopolymères de l'acide acrylique constituent des agents efficaces pour aider à la dispersion ou au broyage en milieu humide du carbonate de calcium. En guise de référence, on pourra se reporter aux documents FR 2 539 137, FR 2 683 536, FR 2 683 537, FR 2 683 538, FR 2 683 539 et FR 2 802 830, qui illustrent entre autres différentes variantes de ces homopolymères, en fonction de leur poids moléculaire et de leur neutralisation. The prior art is particularly rich about such additives. For many years, it has been known that homopolymers of acrylic acid are effective agents in assisting the dispersion or wet milling of calcium carbonate. By way of a reference, reference may be made to documents FR 2 539 137, FR 2 683 536, FR 2 683 537, FR 2 683 538, FR 2 683 539 and FR 2 802 830, which illustrate among other variants of these homopolymers. , depending on their molecular weight and their neutralization.
Pour le même type d'applications, il est également intéressant de copolymériser l'acide acrylique avec un autre monomère carboxylique, tel que par exemple l'acide méthacrylique ou l'anhydride maléique, et/ou avec un autre monomère à insaturation éthylénique mais sans fonction carboxylique, comme un ester acrylique : ces variantes sont également décrites dans les documents précédents. On peut aussi polymériser l'acide acrylique avec un monomère cationique : le polymère obtenu permet avantageusement de disperser ou de traiter un talc dans l'eau, tout en lui conférant des propriétés anti-tackifiantes dans le procédé de fabrication de la feuille de papier (FR 2 900 411). For the same type of applications, it is also advantageous to copolymerize the acrylic acid with another carboxylic monomer, such as, for example, methacrylic acid or maleic anhydride, and / or with another ethylenically unsaturated monomer but without carboxylic function, such as an acrylic ester: these variants are also described in the previous documents. It is also possible to polymerize acrylic acid with a cationic monomer: the polymer obtained advantageously makes it possible to disperse or treat a talc in water, while giving it anti-tackifying properties in the process of manufacturing the paper sheet ( FR 2 900 411).
De même, il est également connu de copolymériser l'acide acrylique, éventuellement avec un des comonomères précités, et avec un monomère non-ionique de formule générale R-X-R' : R désigne une liaison polymérisable, X est un groupement oxyalkylé, et R' est un groupe terminal de type aryle et/ou alkyle plus ou moins hydrophobe. Outre leur capacité à disperser et à broyer efficacement un carbonate de calcium, ces polymères apportent des propriétés supplémentaires au produit final dans lequel est mis en oeuvre ledit carbonate : ces propriétés sont notamment conditionnées par la nature du groupement R'. Similarly, it is also known to copolymerize acrylic acid, optionally with one of the aforementioned comonomers, and with a nonionic monomer of general formula RXR ': R denotes a polymerizable bond, X is an oxyalkylated group, and R' is a terminal group of aryl and / or more or less hydrophobic alkyl type. In addition to their ability to effectively disperse and grind calcium carbonate, these polymers provide additional properties to the final product in which said carbonate is used: these properties are in particular conditioned by the nature of the group R '.
Ainsi, le document FR 2 810 261 fait état de suspensions aqueuses de carbonate de calcium avec un faible potentiel zêta. Les documents FR 2 846 978 et FR 2 846 972 décrivent l'utilisation de carbonates broyés ou dispersés dans l'eau, puis introduits dans des sauces de couchage dont ils améliorent les propriétés optiques. Le document FR 2 893 031 divulgue des carbonates broyés et mis en oeuvre dans des plastiques pour en améliorer les propriétés mécaniques. Les documents FR 2 913 426, FR 2 913 420 et FR 2 913 428 portent quant à eux sur la technique particulière du broyage à sec, et sur les avantages procurés dans des applications comme la peinture, le plastique et le ciment. Thus, document FR 2 810 261 mentions aqueous suspensions of calcium carbonate with a low zeta potential. The documents FR 2 846 978 and FR 2 846 972 describe the use of crushed or dispersed carbonates in water, then introduced into coating colors whose optical properties they improve. Document FR 2 893 031 discloses crushed carbonates and used in plastics to improve the mechanical properties thereof. Documents FR 2 913 426, FR 2 913 420 and FR 2 913 428 relate to the particular technique of dry grinding, and the advantages provided in applications such as paint, plastic and cement.
On connaît aujourd'hui des solutions techniques qui permettent de minimiser la quantité d'agents dispersants ou d'aide au broyage de l'art antérieur, c'est-à-dire dont la synthèse est issue de matières premières fossiles. Ainsi, le document EP 1 728 771 propose d'utiliser, en combinaison avec des agents de broyage de l'art antérieur, des composés à base de diols et de triols issus de la glycérine (cette possibilité avait déjà été décrite dans le document US 4 204 877, pour le broyage du ciment). Si elle représente une avancée dans le sens d'une chimie plus "verte" issue de la biomasse, cette solution n'est pas pleinement satisfaisante, puisque la totalité des agents de broyage de l'art antérieur ne peut être éliminée, sans perdre en efficacité en terme de broyage. Technical solutions are known today that make it possible to minimize the amount of dispersing agents or grinding aid of the prior art, that is to say the synthesis of which is derived from fossil raw materials. Thus, the document EP 1 728 771 proposes to use, in combination with grinding agents of the prior art, compounds based on diols and triols derived from glycerine (this possibility had already been described in the US document 4,204,877, for grinding cement). If it represents a step in the direction of a "greener" chemistry from biomass, this solution is not fully satisfactory, since all the grinding agents of the prior art can not be eliminated, without losing in efficiency in terms of grinding.
Poursuivant ses recherches, la Demanderesse a aujourd'hui mis au point l'utilisation, comme agent de dispersion et/ou d'aide au broyage de matières minérales, de polymères fabriqués en polymérisant au moins un monomère qui est l'acide acrylique, cet acide acrylique étant issu du glycérol, et non du propylène. Continuing its research, the Applicant has today developed the use, as dispersant and / or grinding aid of mineral materials, of polymers made by polymerizing at least one monomer which is acrylic acid, this acrylic acid being derived from glycerol, and not propylene.
De manière avantageuse, le glycérol est en effet issu de la méthanolyse des huiles végétales : il s'agit d'un sous produit de cette réaction, ladite réaction visant essentiellement à obtenir des esters méthyliques d'acides gras. Le glycérol est une ressource renouvelable, naturelle, disponible en très grande quantité et on sait aujourd'hui comment obtenir de l'acide acrylique directement à partir du glycérol : par déshydratation de ce dernier, en présence d'oxygène. Cette technique est décrite dans les documents FR 2 884 817, FR 2 884 818, FR 2 909 999. Elle représente une alternative tout à fait avantageuse d'un point de vue environnemental et de préservation de nos ressources naturelles, par rapport aux anciens procédés dans lesquels l'acide acrylique était issu du craquage du propylène. Advantageously, glycerol is indeed derived from the methanolysis of vegetable oils: it is a byproduct of this reaction, said reaction essentially aimed at obtaining methyl esters of fatty acids. Glycerol is a renewable resource, natural, available in very large quantities and today we know how to obtain acrylic acid directly from glycerol: by dehydration of the latter, in the presence of oxygen. This technique is described in the documents FR 2 884 817, FR 2 884 818, FR 2 909 999. It represents a very advantageous alternative from an environmental point of view and preservation of our natural resources, compared to the old processes. in which the acrylic acid was derived from the cracking of propylene.
Un des mérites de la Demanderesse est d'avoir su identifier cette technologie de synthèse de l'acide acrylique, comme une nouvelle voie permettant de fournir aux fabricants de dispersants et d'agents d'aide au broyage une matière première de base issue d'une chimie "verte" : de l'acide acrylique provenant de la déshydratation du glycérol. La Demanderesse a également démontré que les polymères ainsi fabriqués, se comportaient comme des agents de dispersion et/ou d'aide au broyage tout à fait efficaces, dans le cas du carbonate de calcium. Ce faisant, elle a ainsi contribué à enrichir l'état de la technique par une alternative technique efficace, respectueuse de l'environnement et de nos ressources naturelles. One of the merits of the Applicant is to have been able to identify this acrylic acid synthesis technology, as a new way to provide manufacturers of dispersants and grinding aid agents a basic raw material derived from "green" chemistry: acrylic acid from the dehydration of glycerol. The Applicant has also demonstrated that the polymers thus produced, behaved as dispersing agents and / or grinding aid quite effective, in the case of calcium carbonate. In so doing, it has contributed to enriching the state of the art with an effective technical alternative that respects the environment and our natural resources.
Aussi, un premier objet de l'invention consiste en l'utilisation, comme agent de dispersion et/ou d'aide au broyage d'une matière minérale, d'un homopolymère ou d'un copolymère de l'acide acrylique, caractérisée en ce que ledit acide acrylique est issu du glycérol. Cette utilisation est aussi caractérisée en ce que ledit acide acrylique est issu du glycérol, par l'intermédiaire d'une réaction de déshydratation de celui-ci, préférentiellement en présence d'oxygène.30 Cette utilisation est aussi caractérisée en ce que ledit homopolymère ou copolymère de l'acide acrylique est totalement ou partiellement neutralisé. Also, a first object of the invention is the use, as dispersion agent and / or grinding aid of a mineral material, a homopolymer or a copolymer of acrylic acid, characterized in that that said acrylic acid is derived from glycerol. This use is also characterized in that said acrylic acid is derived from glycerol, via a dehydration reaction thereof, preferably in the presence of oxygen. This use is also characterized in that said homopolymer or Copolymer of acrylic acid is totally or partially neutralized.
Cette utilisation est caractérisée en ce que ledit homopolymère ou copolymère de l'acide acrylique est obtenu par des procédés de polymérisation radicalaire en solution, en émulsion directe ou inverse, en suspension ou précipitation dans des solvants appropriés, en présence de systèmes catalytiques et d'agents de transfert, ou encore par des procédés de polymérisation radicalaire contrôlée et préférentiellement par la polymérisation contrôlée par des nitroxydes (NMP) ou par des cobaloxymes, la polymérisation par transfert d'atome radicalaire (ATRP), la polymérisation radicalaire contrôlée par des dérivés soufrés, choisis parmi des carbamates, des dithioesters ou des trithiocarbonates (RAFT) ou des xanthates. This use is characterized in that said homopolymer or copolymer of acrylic acid is obtained by radical solution polymerization processes, in direct or inverse emulsion, in suspension or precipitation in appropriate solvents, in the presence of catalytic systems and transfer agents, or by controlled radical polymerization processes and preferentially by controlled polymerization with nitroxides (NMP) or by cobaloxymes, radical atom transfer polymerization (ATRP), controlled radical polymerization with sulfur derivatives , selected from carbamates, dithioesters or trithiocarbonates (RAFT) or xanthates.
Cette utilisation est caractérisée en ce que ledit homopolymère ou copolymère de l'acide acrylique, lorsqu'il est totalement ou partiellement neutralisé, l'est avec au moins un agent de neutralisation monovalent, divalent, trivalent ou de valence supérieure, et en ce qu'il est choisi préférentiellement parmi les amines, les hydroxydes de sodium, de potassium, les hydroxydes et / ou oxydes de calcium, de magnésium, et leurs mélanges. This use is characterized in that said homopolymer or copolymer of acrylic acid, when it is totally or partially neutralized, is with at least one monovalent, divalent, trivalent or higher valence neutralizing agent, and in that it is preferably chosen from amines, hydroxides of sodium, of potassium, hydroxides and / or oxides of calcium and magnesium, and mixtures thereof.
Cette utilisation est aussi caractérisée en ce que, éventuellement avant ou après sa neutralisation totale ou partielle, ledit homopolymère ou copolymère de l'acide acrylique peut être traité et séparé en plusieurs phases, selon des procédés statiques ou dynamiques, par un ou plusieurs solvants polaires appartenant préférentiellement au groupe constitué par l'eau, le méthanol, l'éthanol, le propanol, l'isopropanol, les butanols, l'acétone, le tétrahydrofurane ou leurs mélanges. L'une des deux phases correspond alors aux polymères utilisés selon l'invention. This use is also characterized in that, optionally before or after its total or partial neutralization, said homopolymer or copolymer of acrylic acid can be treated and separated into several phases, according to static or dynamic processes, with one or more polar solvents preferably belonging to the group consisting of water, methanol, ethanol, propanol, isopropanol, butanols, acetone, tetrahydrofuran or mixtures thereof. One of the two phases then corresponds to the polymers used according to the invention.
Cette utilisation est aussi caractérisée en ce que ledit homopolymère ou copolymère de l'acide acrylique peut être séché. Cette utilisation est aussi caractérisée en ce que ledit copolymère de l'acide acrylique est obtenu par copolymérisation dudit acide acrylique avec au moins un autre monomère hydrosoluble.30 Cette utilisation est aussi caractérisée en ce que l'autre monomère hydrosoluble est choisi parmi : This use is also characterized in that said homopolymer or copolymer of acrylic acid can be dried. This use is also characterized in that said copolymer of acrylic acid is obtained by copolymerization of said acrylic acid with at least one other water-soluble monomer. This use is also characterized in that the other water-soluble monomer is chosen from:
a) un autre monomère carboxylique, différent de l'acide acrylique, b) et/ou un autre monomère à insaturation éthylénique, mais sans fonction carboxylique, c) et/ou un monomère cationique, d) et/ou un monomère non-ionique différent du monomère b). a) another carboxylic monomer, other than acrylic acid, b) and / or another ethylenically unsaturated monomer, but without a carboxylic function, c) and / or a cationic monomer, d) and / or a nonionic monomer different from the monomer b).
Cette utilisation est aussi caractérisée en ce que l'autre monomère carboxylique a) est choisi parmi des monomères à fonction monocarboxylique et préférentiellement parmi les acides méthacrylique, crotonique, isocrotonique, cinnamique, ou est choisi parmi les hémiesters de diacides et préférentiellement parmi les monoesters en CI à C4 des acides maléique ou itaconique, ou est choisi parmi les monomères à insaturation éthylénique et fonction dicarboxylique à l'état acide ou salifié, et préférentiellement parmi l'acide itaconique, maléique, fumarique, mésaconique, citraconique, ou est choisi parmi les anhydrides d'acides carboxyliques, et est préférentiellement l'anhydride maléique, ou est choisi parmi les mélanges de ces monomères. This use is also characterized in that the other carboxylic monomer a) is chosen from monomers with a monocarboxylic function and preferably from methacrylic, crotonic, isocrotonic or cinnamic acids, or is chosen from half esters of diacids and preferably from monoesters containing CI to C4 maleic or itaconic acid, or is selected from the monomers with ethylenic unsaturation and dicarboxylic function in the acid or salified state, and preferably among itaconic acid, maleic, fumaric, mesaconic, citraconic, or is selected from anhydrides of carboxylic acids, and is preferably maleic anhydride, or is selected from mixtures of these monomers.
Cette utilisation est aussi caractérisée en ce que l'autre monomère à insaturation éthylénique, mais sans fonction carboxylique, soit le monomère b), est choisi parmi les monomères à insaturation éthylénique et à fonction sulfonique à l'état acide ou salifié, et préférentiellement parmi l'acide acrylamido-2-méthyl-2-propane-sulfonique, le méthallylsulfonate de sodium, l'acide vinyl sulfonique et l'acide styrène sulfonique, ou est choisi parmi les monomères à insaturation éthylénique et à fonction phosphorique à l'état acide ou salifié, et préférentiellement parmi l'acide vinyl phosphorique, le phosphate de méthacrylate d'éthylène glycol, le phosphate de méthacrylate de propylène glycol, le phosphate d'acrylate d'éthylène glycol, le phosphate d'acrylate de propylène glycol et leurs éthoxylats, ou est choisi parmi les monomères à insaturation éthylénique et à fonction phosphonique à l'état acide ou salifié, et est préférentiellement l'acide vinyl phosphonique, ou est choisi parmi les mélanges de ces monomères. This use is also characterized in that the other ethylenically unsaturated monomer, but without a carboxylic function, ie the monomer b), is chosen from ethylenically unsaturated monomers with a sulphonic function in the acid or salified state, and preferably from acrylamido-2-methyl-2-propanesulfonic acid, sodium methallyl sulphonate, vinyl sulphonic acid and styrene sulphonic acid, or is chosen from the monomers with ethylenic unsaturation and phosphoric function in the acidic state. or salified, and preferentially among vinyl phosphoric acid, ethylene glycol methacrylate phosphate, propylene glycol methacrylate phosphate, ethylene glycol acrylate phosphate, propylene glycol acrylate phosphate and their ethoxylates , or is selected from ethylenically unsaturated monomers and phosphonic function in the acid or salified state, and is preferably the acid e phosphonic vinyl, or is selected from mixtures of these monomers.
Cette utilisation est aussi caractérisée en ce que le monomère cationique c) est choisi parmi les ammonium quaternaires, et préférentiellement parmi le chlorure ou le sulfate de [2-(méthacryloyloxy) éthyl] triméthyl ammonium, le chlorure ou le sulfate de [2-(acryloyloxy) éthyl] triméthyl ammonium, le chlorure ou le sulfate de [3-(acrylamido) propyl] triméthyl ammonium, le chlorure ou le sulfate de diméthyl diallyl ammonium, le chlorure ou le sulfate de [3-(méthacrylamido) propyl] triméthyl ammonium, ou est choisi parmi les mélanges de ces monomères. This use is also characterized in that the cationic monomer c) is chosen from quaternary ammonium, and preferably from [2- (methacryloyloxy) ethyl] trimethyl ammonium chloride or sulphate, [2- acryloyloxy) ethyl] trimethyl ammonium, [3- (acrylamido) propyl] trimethyl ammonium chloride or sulfate, dimethyl diallyl ammonium chloride or sulphate, [3- (methacrylamido) propyl] trimethyl ammonium chloride or sulphate or is selected from mixtures of these monomers.
Cette utilisation est aussi caractérisée en ce que le monomère d) est choisi parmi le N-[3-(diméthylamino) propyl] acrylamide, le N-[3-(diméthylamino) propyl] méthacrylamide, les esters insaturés tels que le méthacrylate de N-[2-(diméthylamino) éthyl], ou l'acrylate de N-[2-(diméthylamino) éthyl], ou parmi l'acrylamide, le méthacrylamide, les acrylates ou méthacrylates d' alkyle, les vinyliques, et préférentiellement l'acétate de vinyle, la vinylpyrrolidone, le styrène, l'alphaméthylstyrène et leurs dérivés, ou parmi les monomères de formule (I) : (I) 15 dans laquelle : - m, n, p et q sont des entiers et m, n, p sont inférieurs à 150, q est supérieur à 0 et au moins un entier parmi m, n et p est non nul, - R est un radical comportant une fonction insaturée polymérisable, appartenant préférentiellement au groupe des vinyliques ainsi qu'au groupe des esters 20 acrylique, méthacrylique, maléique, ainsi qu'au groupe des insaturés uréthannes tels que les acryluréthanne, méthacryluréthanne, a-a' diméthyl-isopropénylbenzyluréthanne, allyluréthanne, de même qu'au groupe des éthers allyliques ou vinyliques substitués ou non, ou encore au groupe des amides ou des imides éthyléniquement insaturées, 25 - RI et R2 sont identiques ou différents et représentent des atomes d'hydrogène ou des groupements alkyls, - R' représente l'hydrogène ou une chaîne alkyle et/ou aryle, linéaire ou ramifiée, ayant de 1 à 40 atomes de carbone. This use is also characterized in that the monomer d) is chosen from N- [3- (dimethylamino) propyl] acrylamide, N- [3- (dimethylamino) propyl] methacrylamide and unsaturated esters such as N-methacrylate. [2- (dimethylamino) ethyl], or N- [2- (dimethylamino) ethyl] acrylate, or from acrylamide, methacrylamide, alkyl acrylates or methacrylates, vinylic acids, and preferentially vinyl acetate, vinylpyrrolidone, styrene, alphamethylstyrene and their derivatives, or from the monomers of formula (I): in which: m, n, p and q are integers and m, n, p are less than 150, q is greater than 0 and at least one integer from m, n and p is non-zero, - R is a radical having a polymerizable unsaturated functional group, preferably belonging to the group of vinyls and to the group of esters. Acrylic, methacrylic, maleic, as well as to the group of unsaturated urethanes such as crylurethane, methacrylurethane, aa-dimethyl-isopropenylbenzylurethane, allylurethane, as well as the group of substituted or unsubstituted allylic or vinyl ethers, or alternatively to the group of ethylenically unsaturated amides or imides, R 1 and R 2 are identical or different and represent hydrogen atoms or alkyl groups; R 'represents hydrogen or a linear or branched alkyl and / or aryl chain having from 1 to 40 carbon atoms.
Cette utilisation est aussi caractérisée en ce que ladite matière minérale est une matière minérale ou carbonée, et est choisie parmi le carbonate de calcium naturel ou synthétique, les dolomies, le kaolin, le talc, le gypse, l'oxyde de titane, le blanc satin, le trihydroxyde d'aluminium, le mica, le noir de carbone, les mélanges de ces charges entre elles, et préférentiellement les mélanges talc-carbonate de calcium, carbonate de calcium-kaolin, ou encore les mélanges de carbonate de calcium avec le trihydroxyde d'aluminium, les mélanges avec des fibres synthétiques ou naturelles, les co-structures des minéraux comme les co-structures talc-carbonate de calcium ou talc-dioxyde de titane, et en ce que la matière minérale est préférentiellement choisie parmi le carbonate de calcium naturel ou synthétique. This use is also characterized in that said mineral material is a mineral or carbonaceous material, and is selected from natural or synthetic calcium carbonate, dolomites, kaolin, talc, gypsum, titanium oxide, white satin, aluminum trihydroxide, mica, carbon black, mixtures of these fillers with one another, and preferentially talc-calcium carbonate, calcium carbonate-kaolin mixtures, or mixtures of calcium carbonate with the aluminum trihydroxide, mixtures with synthetic or natural fibers, co-structures of minerals such as talc-calcium carbonate or talc-titanium dioxide co-structures, and in that the mineral material is preferably selected from carbonate natural or synthetic calcium.
Les exemples qui suivent permettront de mieux comprendre l'invention, sans toutefois en limiter la portée. The examples which follow will make it possible to better understand the invention, without however limiting its scope.
EXEMPLES Exemple 1 Cet exemple illustre la mise en oeuvre d'acides polyacryliques selon l'art antérieur et selon l'invention, comme agents d'aide au broyage dans l'eau de carbonate de calcium. EXAMPLES Example 1 This example illustrates the use of polyacrylic acids according to the prior art and according to the invention, as grinding aid agents in calcium carbonate water.
Pour ce faire, on broye selon le protocole décrit dans la demande de brevet FR 2 539 137 10 un carbonate de calcium qui est une calcite provenant d'Orgon (France). To do this, according to the protocol described in the patent application FR 2,539,137, a calcium carbonate which is a calcite originating from Orgon (France) is milled.
L'essai n° 1 met en oeuvre 1,1 % en poids sec (par rapport au poids sec de matière minérale) d'un acide polyacrylique selon l'art antérieur, dont 70 % en mole des sites carboxyliques sont neutralisés par de la soude et 30 % en mole par de la chaux, de poids 15 moléculaire égal à 5 500 g/mol tel que mesuré par GPC. Cet acide polyacrylique est fabriqué à partir d'acide acrylique glacial commercialisé par la société ARKEMATM. Cet acide polyacrylique est synthétisé selon une méthode bien connue de l'homme du métier qui est une polymérisation radicalaire en solution dans de l'eau, mettant en oeuvre un initiateur qui est l'eau oxygénée et un réducteur qui est 20 l'hypophosphite. Ce type de synthèse est décrit de manière très détaillée dans le document EP 0 819 704. Test No. 1 uses 1.1% by dry weight (relative to the dry weight of mineral matter) of a polyacrylic acid according to the prior art, of which 70% by mole of the carboxylic sites are neutralized by sodium hydroxide and 30 mol% by lime, of molecular weight equal to 5,500 g / mol as measured by GPC. This polyacrylic acid is made from glacial acrylic acid marketed by the company ARKEMATM. This polyacrylic acid is synthesized according to a method well known to those skilled in the art which is a radical polymerization in solution in water, using an initiator which is hydrogen peroxide and a reducing agent which is hypophosphite. This type of synthesis is described in great detail in EP 0 819 704.
L'essai n° 2 met en oeuvre 1,1 % en poids sec (par rapport au poids sec de matière minérale) d'un acide polyacrylique dont 70 % en mole des sites carboxyliques sont 25 neutralisés par de la soude et 30 % en mole par de la chaux, de poids moléculaire égal à 5 500 g/mol, et obtenu par polymérisation d'acide acrylique glacial issu de la déshydratation du glycérol en présence d'oxygène, selon le procédé décrit dans la demande de brevet FR 2 884 817. Cet acide polyacrylique a été synthétisé de la même manière que l'acide polyacrylique de 30 l'essai n° 1. Test No. 2 uses 1.1% by dry weight (relative to the dry weight of mineral matter) of a polyacrylic acid of which 70% by mole of the carboxylic sites are neutralized with sodium hydroxide and 30% by weight. mole with lime, with a molecular weight equal to 5,500 g / mol, and obtained by polymerization of glacial acrylic acid resulting from the dehydration of glycerol in the presence of oxygen, according to the process described in the patent application FR 2,884 817. This polyacrylic acid was synthesized in the same manner as the polyacrylic acid of Run No. 1.
Pour chacun des essais, on détermine l'extrait sec (% en poids sec de matière minérale par rapport au poids total de la suspension) et le pH de la suspension finale.5 On détermine également le % en poids de particules dont le diamètre moyen est inférieur à 1 m, tel que mesuré à partir d'un SedigraphTM 5100, commercialisé par la société MICROMERITICSTM On mesure enfin, pour la suspension obtenue, à 25°C, sa viscosité BrookfieldTM à 10 et 5 100 tours / minute immédiatement après broyage ( l0 to, l00 to), 8 jours avant agitation ( l 0 t8AVAG, l 00 t8AvAG) et 8 jours après agitation ( l 0 t8APAG, l 00 t8APAG) For each of the tests, the dry extract (% by dry weight of mineral matter relative to the total weight of the suspension) and the pH of the final suspension are determined. The% by weight of particles whose average diameter is also determined is determined. is less than 1 m, as measured from a SedigraphTM 5100, sold by the company MICROMERITICSTM Finally, for the suspension obtained, at 25 ° C., its Brookfield ™ viscosity is measured at 10 and 100 rpm immediately after grinding. (10 to, 100 to), 8 days before shaking (10 T8AVAG, 100 t8AvAG) and 8 days after shaking (100 TAGAPAG, 100 t8APAG)
Ces données sont reportées dans le tableau 1. Essai n° 1 2 Art Antérieur AA IN INvention % < 1 m 80,1 80,2 ES (%) 75,9 76 pH 8,6 8,6 loto 1910 1870 l00 to 530 520 l0 tsAVAG 4340 4300 l00 t8AVAG 1150 1150 l0 t8APAG 1890 1850 l00 t8APAG 560 520 Tableau 1 These data are reported in Table 1. Test No. 1 2 Prior Art AA IN INvention% <1 m 80.1 80.2 ES (%) 75.9 76 pH 8.6 8.6 lotto 1910 1870 l00 to 530 520 l0 tsAVAG 4340 4300 l00 t8AVAG 1150 1150 l0 t8APAG 1890 1850 l00 t8APAG 560 520 Table 1
Ces résultats démontrent qu'un acide polyacrylique, obtenu par polymérisation d'acide acrylique via la déshydratation du glycérol en présence d'oxygène, peut être substitué de 15 manière tout à fait avantageuse du point de vue du respect de l'environnement à un acide polyacrylique de l'art antérieur, les performances obtenues en broyage étant tout à fait similaires. 10 These results demonstrate that a polyacrylic acid, obtained by polymerization of acrylic acid via the dehydration of glycerol in the presence of oxygen, can be very advantageously substituted from the point of view of environmental friendliness to an acid. polyacrylic art of the prior art, the performance obtained in grinding being quite similar. 10
Claims (14)
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| FR0858219A FR2939055A1 (en) | 2008-12-03 | 2008-12-03 | Use of a mineral material, homopolymer or copolymer of acrylic acid, as dispersing agent and/or grinding aid agent, where the acrylic acid is obtained from glycerol |
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| FR0858219A FR2939055A1 (en) | 2008-12-03 | 2008-12-03 | Use of a mineral material, homopolymer or copolymer of acrylic acid, as dispersing agent and/or grinding aid agent, where the acrylic acid is obtained from glycerol |
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| CN102875727A (en) * | 2012-10-15 | 2013-01-16 | 成都理工大学 | Preparation method for micro-crystal muscovite compounded and crylic acid-acrylamide-itaconic acid polymerized super absorbent resin |
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| WO2014076437A1 (en) * | 2012-11-19 | 2014-05-22 | Coatex | Use of a water-soluble copolymer for preparing an aqueous lime suspension |
| EP2868716A1 (en) | 2013-11-04 | 2015-05-06 | Omya International AG | Process for producing a high solids pigment suspension comprising carboxymethylcellulose-based dispersant |
| US9757685B2 (en) | 2012-11-19 | 2017-09-12 | Coatex | Aqueous lime slurry, preparation process and uses |
| CN113058585A (en) * | 2020-01-02 | 2021-07-02 | 万华化学集团股份有限公司 | Alpha, alpha-dimethyl benzyl alcohol hydrogenolysis catalyst and preparation method thereof |
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| CN113058585A (en) * | 2020-01-02 | 2021-07-02 | 万华化学集团股份有限公司 | Alpha, alpha-dimethyl benzyl alcohol hydrogenolysis catalyst and preparation method thereof |
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