CH630642A5 - Verfahren zur herstellung von ozoniertem ligninsulfonat. - Google Patents
Verfahren zur herstellung von ozoniertem ligninsulfonat. Download PDFInfo
- Publication number
- CH630642A5 CH630642A5 CH705777A CH705777A CH630642A5 CH 630642 A5 CH630642 A5 CH 630642A5 CH 705777 A CH705777 A CH 705777A CH 705777 A CH705777 A CH 705777A CH 630642 A5 CH630642 A5 CH 630642A5
- Authority
- CH
- Switzerland
- Prior art keywords
- ozone
- weight
- lignin sulfonate
- oxidized
- dispersion
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 title description 5
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 claims description 93
- 229920001732 Lignosulfonate Polymers 0.000 claims description 88
- 238000006243 chemical reaction Methods 0.000 claims description 45
- 238000000034 method Methods 0.000 claims description 38
- 239000006185 dispersion Substances 0.000 claims description 21
- 230000003647 oxidation Effects 0.000 claims description 16
- 238000007254 oxidation reaction Methods 0.000 claims description 16
- 239000007787 solid Substances 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 14
- 230000008569 process Effects 0.000 claims description 13
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 239000001301 oxygen Substances 0.000 claims description 12
- 238000006385 ozonation reaction Methods 0.000 claims description 12
- 239000007858 starting material Substances 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- 239000011593 sulfur Substances 0.000 claims description 12
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 7
- 239000007789 gas Substances 0.000 claims description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 6
- 238000010521 absorption reaction Methods 0.000 claims description 6
- 238000006277 sulfonation reaction Methods 0.000 claims description 6
- 239000003513 alkali Substances 0.000 claims description 3
- 239000012431 aqueous reaction media Substances 0.000 claims description 3
- 239000008247 solid mixture Substances 0.000 claims description 3
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 claims description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 claims description 2
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims description 2
- 150000003457 sulfones Chemical class 0.000 claims description 2
- VXQCHFNZKLDPNC-UHFFFAOYSA-N OS([S])(=O)=O Chemical compound OS([S])(=O)=O VXQCHFNZKLDPNC-UHFFFAOYSA-N 0.000 claims 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 239000003518 caustics Substances 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- -1 sulfomethylene groups Chemical group 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 40
- 239000000463 material Substances 0.000 description 27
- 238000012360 testing method Methods 0.000 description 16
- 235000011121 sodium hydroxide Nutrition 0.000 description 15
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 14
- 239000002270 dispersing agent Substances 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- 239000011121 hardwood Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 238000011156 evaluation Methods 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 8
- 230000008901 benefit Effects 0.000 description 7
- 229920005610 lignin Polymers 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 239000002699 waste material Substances 0.000 description 7
- 230000001590 oxidative effect Effects 0.000 description 6
- 239000004568 cement Substances 0.000 description 5
- 235000000346 sugar Nutrition 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 235000019357 lignosulphonate Nutrition 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000002609 medium Substances 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 239000007800 oxidant agent Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 239000012266 salt solution Substances 0.000 description 4
- 239000010802 sludge Substances 0.000 description 4
- 125000000542 sulfonic acid group Chemical group 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- 239000006260 foam Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 239000011122 softwood Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 235000019892 Stellar Nutrition 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000012159 carrier gas Substances 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000010520 demethylation reaction Methods 0.000 description 2
- 230000006326 desulfonation Effects 0.000 description 2
- 238000005869 desulfonation reaction Methods 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 230000015784 hyperosmotic salinity response Effects 0.000 description 2
- 239000002655 kraft paper Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000013049 sediment Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- YALHCTUQSQRCSX-UHFFFAOYSA-N sulfane sulfuric acid Chemical compound S.OS(O)(=O)=O YALHCTUQSQRCSX-UHFFFAOYSA-N 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- HGXBRUKMWQGOIE-AFHBHXEDSA-N (+)-pinoresinol Chemical group C1=C(O)C(OC)=CC([C@@H]2[C@@H]3[C@@H]([C@H](OC3)C=3C=C(OC)C(O)=CC=3)CO2)=C1 HGXBRUKMWQGOIE-AFHBHXEDSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000004117 Lignosulphonate Substances 0.000 description 1
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 1
- JQYCSHXHVCKLGB-UHFFFAOYSA-N S.OS(O)=O Chemical compound S.OS(O)=O JQYCSHXHVCKLGB-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 229920001448 anionic polyelectrolyte Polymers 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- AFYPFACVUDMOHA-UHFFFAOYSA-N chlorotrifluoromethane Chemical compound FC(F)(F)Cl AFYPFACVUDMOHA-UHFFFAOYSA-N 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000017858 demethylation Effects 0.000 description 1
- 230000001066 destructive effect Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000003129 oil well Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000013021 overheating Methods 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical group CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 1
- 238000004537 pulping Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08H—DERIVATIVES OF NATURAL MACROMOLECULAR COMPOUNDS
- C08H6/00—Macromolecular compounds derived from lignin, e.g. tannins, humic acids
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
- Y10S516/01—Wetting, emulsifying, dispersing, or stabilizing agents
- Y10S516/03—Organic sulfoxy compound containing
Landscapes
- Chemical & Material Sciences (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Paper (AREA)
- Compounds Of Unknown Constitution (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/697,541 US4088640A (en) | 1976-06-18 | 1976-06-18 | Ozonated lignosulfonates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH630642A5 true CH630642A5 (de) | 1982-06-30 |
Family
ID=24801512
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH705777A CH630642A5 (de) | 1976-06-18 | 1977-06-08 | Verfahren zur herstellung von ozoniertem ligninsulfonat. |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4088640A (en:Method) |
| AT (1) | AT371862B (en:Method) |
| CA (1) | CA1092098A (en:Method) |
| CH (1) | CH630642A5 (en:Method) |
| DE (1) | DE2727317C2 (en:Method) |
| FI (1) | FI62851C (en:Method) |
| FR (1) | FR2355051A1 (en:Method) |
| NO (1) | NO151042C (en:Method) |
| SE (1) | SE437842B (en:Method) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4172498A (en) * | 1975-06-30 | 1979-10-30 | Texaco Inc. | Sulfomethylated lignosulfonates as additives in oil recovery processes involving chemical recovery agents |
| US4181652A (en) * | 1976-06-18 | 1980-01-01 | American Can Company | Ozonated lignosulfonates |
| US4269270A (en) * | 1978-04-28 | 1981-05-26 | Texaco Inc. | Sulfomethylated lignosulfonates as additives in oil recovery processes involving chemical recovery agents |
| US4384997A (en) * | 1978-09-29 | 1983-05-24 | Reed Lignin, Inc. | Lignosulfonated derivatives for use in enhanced oil recovery |
| US4220585A (en) * | 1979-04-04 | 1980-09-02 | Dresser Industries, Inc. | Drilling fluid additives |
| FR2498605A2 (fr) * | 1981-01-29 | 1982-07-30 | Avebene | Nouveaux derives de l'acide lignosulfonique, procede pour leur preparation et leur utilisation comme additifs pour boues de forage |
| FR2476650A1 (fr) * | 1980-02-27 | 1981-08-28 | Avebene | Nouveaux derives de l'acide lignosulfonique, procede pour leur preparation et leur utilisation comme additifs pour boues de forage |
| US5104584A (en) * | 1990-06-22 | 1992-04-14 | The Clorox Company | Composition and method for fabric encrustation prevention comprising a lignin derivative |
| US5281434A (en) * | 1992-05-26 | 1994-01-25 | Lignotech Usa | Composition and process of making an animal feed binder composed of ozonated lignosulfonate |
| US7329385B1 (en) | 2004-07-08 | 2008-02-12 | Radicone Michael C | Device and method for air stream, fluid and vessel decontamination |
| EP2213165A1 (en) * | 2007-11-27 | 2010-08-04 | Erc Technology Inc. | Novel compositions containing ozonized surfactant |
| HU228038B1 (en) * | 2009-02-20 | 2012-08-28 | Uchrin Friderika | Method of enhancing yield of soluble humate substances and production of biologically active preparations |
| CA2716663A1 (en) * | 2009-10-06 | 2011-04-06 | University Of Windsor | Method and process of producing short chain fatty acids from waste stream containing phenolic lignin model compounds by controlled photocatalytic oxidation with titanium dioxide nanocatalyst in the presence of ultraviolet radiation |
| WO2011065832A2 (en) | 2009-11-27 | 2011-06-03 | Ceradis B.V. | Improved formulations of phosphites |
| JP2015509530A (ja) | 2012-03-05 | 2015-03-30 | セラディス ベー．フェー． | 殺生物剤強化のためのナタマイシン及び／又はホスファイトを含む多価電解質複合体 |
| EP3041913A2 (en) | 2013-09-04 | 2016-07-13 | Ceradis B.V. | A new antifungal composition for treatment of soil |
| WO2015034357A1 (en) | 2013-09-04 | 2015-03-12 | Ceradis B.V. | Paint composition comprising a polyelectrolyte complex |
| WO2015034360A1 (en) | 2013-09-04 | 2015-03-12 | Ceradis B.V. | Processed edible product comprising a polyelectrolyte complex and an antimicrobial compound |
| TW202234998A (zh) | 2020-12-02 | 2022-09-16 | 以色列商亞達瑪馬克天辛有限公司 | 銅基殺菌劑組成物 |
| AU2023279920A1 (en) | 2022-06-02 | 2024-12-19 | Adama Makhteshim Ltd. | Azole fungicide composition |
| WO2025173008A1 (en) | 2024-02-15 | 2025-08-21 | Adama Makhteshim Ltd. | Solid formulation |
| WO2025181808A1 (en) | 2024-02-29 | 2025-09-04 | Adama Makhteshim Ltd. | Enhanced process efficiency through the novel use of dispersants and processes for producing phthalimide based fungicide |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB694665A (en) * | 1949-12-22 | 1953-07-22 | Erich Adler | Method of producing water-soluble products from black liquor lignin |
| US2680113A (en) * | 1949-12-22 | 1954-06-01 | Svenska Cellulosaforeningens C | Method of producing water-soluble products from black liquor lignin |
| US2935473A (en) * | 1959-05-25 | 1960-05-03 | Puget Sound Pulp And Timber Co | Drilling fluid composition and process |
| US3278425A (en) * | 1960-03-31 | 1966-10-11 | Georgia Pacific Corp | Drilling fluid composition process and product |
| US3168511A (en) * | 1960-03-31 | 1965-02-02 | Georgia Pacific Corp | Sulfonated lignin-containing process and product |
| FR1310097A (en:Method) * | 1960-11-14 | 1963-03-04 | ||
| US3171811A (en) * | 1961-12-08 | 1965-03-02 | Lignosol Chemical Ltd | Well drilling fluids |
| US3325426A (en) * | 1963-09-13 | 1967-06-13 | Georgia Pacific Corp | Oxidized product of sulfonated lignin material reacted with an alkylolphenol |
| US3726850A (en) * | 1971-07-29 | 1973-04-10 | American Can Co | Lignin dispersing agent |
-
1976
- 1976-06-18 US US05/697,541 patent/US4088640A/en not_active Expired - Lifetime
-
1977
- 1977-04-26 CA CA276,975A patent/CA1092098A/en not_active Expired
- 1977-05-12 FI FI771511A patent/FI62851C/fi not_active IP Right Cessation
- 1977-06-08 CH CH705777A patent/CH630642A5/de not_active IP Right Cessation
- 1977-06-16 DE DE2727317A patent/DE2727317C2/de not_active Expired
- 1977-06-16 SE SE7706992A patent/SE437842B/xx not_active IP Right Cessation
- 1977-06-17 FR FR7718704A patent/FR2355051A1/fr active Granted
- 1977-06-17 NO NO772145A patent/NO151042C/no unknown
- 1977-06-17 AT AT0429977A patent/AT371862B/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CA1092098A (en) | 1980-12-23 |
| NO151042C (no) | 1985-02-06 |
| FI62851C (fi) | 1983-03-10 |
| SE7706992L (sv) | 1977-12-19 |
| DE2727317A1 (de) | 1977-12-22 |
| FI771511A7 (en:Method) | 1977-12-19 |
| AT371862B (de) | 1983-08-10 |
| FR2355051B1 (en:Method) | 1984-01-13 |
| ATA429977A (de) | 1982-12-15 |
| FI62851B (fi) | 1982-11-30 |
| NO772145L (no) | 1977-12-20 |
| FR2355051A1 (fr) | 1978-01-13 |
| SE437842B (sv) | 1985-03-18 |
| NO151042B (no) | 1984-10-22 |
| DE2727317C2 (de) | 1987-02-12 |
| US4088640A (en) | 1978-05-09 |
Similar Documents
| Publication | Publication Date | Title |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PUE | Assignment |
Owner name: REED LIGNIN, INC. |
|
| PL | Patent ceased |