CA1092098A - Ozonated lignosulfonates - Google Patents
Ozonated lignosulfonatesInfo
- Publication number
- CA1092098A CA1092098A CA276,975A CA276975A CA1092098A CA 1092098 A CA1092098 A CA 1092098A CA 276975 A CA276975 A CA 276975A CA 1092098 A CA1092098 A CA 1092098A
- Authority
- CA
- Canada
- Prior art keywords
- lignosulfonate
- ozone
- oxidized
- weight
- ozonated
- 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.)
- Expired
Links
- 229920001732 Lignosulfonate Polymers 0.000 title claims abstract description 99
- 239000000203 mixture Substances 0.000 claims abstract description 29
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 claims description 104
- 238000006243 chemical reaction Methods 0.000 claims description 54
- 239000000463 material Substances 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 27
- 238000007254 oxidation reaction Methods 0.000 claims description 21
- 230000003647 oxidation Effects 0.000 claims description 20
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 18
- 239000007787 solid Substances 0.000 claims description 18
- 239000006185 dispersion Substances 0.000 claims description 17
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 16
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- 239000001301 oxygen Substances 0.000 claims description 16
- 239000011593 sulfur Substances 0.000 claims description 15
- 229910052717 sulfur Inorganic materials 0.000 claims description 15
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 14
- 239000003518 caustics Substances 0.000 claims description 13
- 239000007858 starting material Substances 0.000 claims description 12
- 238000006385 ozonation reaction Methods 0.000 claims description 11
- 239000011780 sodium chloride Substances 0.000 claims description 11
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 10
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical group O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 9
- 230000001590 oxidative effect Effects 0.000 claims description 7
- 239000007789 gas Substances 0.000 claims description 6
- ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical compound CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 claims description 5
- 229910006069 SO3H Inorganic materials 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 239000003153 chemical reaction reagent Substances 0.000 claims description 4
- -1 sulfomethyl groups Chemical group 0.000 claims description 4
- 238000006277 sulfonation reaction Methods 0.000 claims description 4
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical group [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 claims description 3
- 239000008247 solid mixture Substances 0.000 claims description 3
- 230000009471 action Effects 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 2
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 2
- 230000002159 abnormal effect Effects 0.000 claims 1
- 239000012141 concentrate Substances 0.000 claims 1
- 239000002270 dispersing agent Substances 0.000 abstract description 15
- 230000015227 regulation of liquid surface tension Effects 0.000 abstract 1
- 239000000047 product Substances 0.000 description 32
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 238000012360 testing method Methods 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 238000011156 evaluation Methods 0.000 description 10
- 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 9
- 239000011121 hardwood Substances 0.000 description 9
- 239000002655 kraft paper Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 235000011121 sodium hydroxide Nutrition 0.000 description 7
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 5
- 230000008901 benefit Effects 0.000 description 5
- 239000004927 clay Substances 0.000 description 5
- 235000000346 sugar Nutrition 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- 235000019892 Stellar Nutrition 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 239000004568 cement Substances 0.000 description 4
- 229920005610 lignin Polymers 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 150000008163 sugars Chemical class 0.000 description 4
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 3
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 3
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 3
- 239000001110 calcium chloride Substances 0.000 description 3
- 229910001628 calcium chloride Inorganic materials 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 239000006260 foam Substances 0.000 description 3
- 229910001629 magnesium chloride Inorganic materials 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
- 230000008569 process Effects 0.000 description 3
- 239000011122 softwood Substances 0.000 description 3
- 239000002699 waste material Substances 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000012159 carrier gas Substances 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 239000000470 constituent Substances 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
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 230000015784 hyperosmotic salinity response Effects 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000003265 pulping liquor Substances 0.000 description 2
- 239000013049 sediment Substances 0.000 description 2
- 239000010802 sludge Substances 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- YALHCTUQSQRCSX-UHFFFAOYSA-N sulfane sulfuric acid Chemical compound S.OS(O)(=O)=O YALHCTUQSQRCSX-UHFFFAOYSA-N 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
- 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
- KKCBUQHMOMHUOY-UHFFFAOYSA-N Na2O Inorganic materials [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
- JQYCSHXHVCKLGB-UHFFFAOYSA-N S.OS(O)=O Chemical compound S.OS(O)=O JQYCSHXHVCKLGB-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 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
- 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
- 238000004140 cleaning Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 239000013256 coordination polymer Substances 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
- 239000004744 fabric Substances 0.000 description 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910000069 nitrogen hydride Inorganic materials 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
- 238000004537 pulping Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 239000003340 retarding agent Substances 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000005201 scrubbing Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 238000010972 statistical evaluation Methods 0.000 description 1
- 150000003463 sulfur Chemical class 0.000 description 1
- 230000000153 supplemental effect Effects 0.000 description 1
- 239000004408 titanium dioxide Substances 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
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)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Compounds Of Unknown Constitution (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US697,541 | 1976-06-18 | ||
| US05/697,541 US4088640A (en) | 1976-06-18 | 1976-06-18 | Ozonated lignosulfonates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1092098A true CA1092098A (en) | 1980-12-23 |
Family
ID=24801512
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA276,975A Expired CA1092098A (en) | 1976-06-18 | 1977-04-26 | Ozonated lignosulfonates |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4088640A (OSRAM) |
| AT (1) | AT371862B (OSRAM) |
| CA (1) | CA1092098A (OSRAM) |
| CH (1) | CH630642A5 (OSRAM) |
| DE (1) | DE2727317C2 (OSRAM) |
| FI (1) | FI62851C (OSRAM) |
| FR (1) | FR2355051A1 (OSRAM) |
| NO (1) | NO151042C (OSRAM) |
| SE (1) | SE437842B (OSRAM) |
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 |
| 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 |
| 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 |
| 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 |
| JPWO2009069619A1 (ja) * | 2007-11-27 | 2011-04-14 | 株式会社Ｅｒｃテクノロジー | オゾン化界面活性剤を含有する新規組成物 |
| 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 |
| BR112012012782A2 (pt) | 2009-11-27 | 2015-09-08 | Ceradis Bv | formulações aprimoradas de fosfitos |
| AU2013228099A1 (en) | 2012-03-05 | 2014-10-02 | Ceradis B.V. | Polyelectrolyte complexes for biocide enhancement |
| EP3041367B1 (en) | 2013-09-04 | 2017-10-25 | Ceradis B.V. | Processed edible product comprising a polyelectrolyte complex and an antimicrobial compound |
| US20160192643A1 (en) | 2013-09-04 | 2016-07-07 | Ceradis B.V. | New antifungal composition for treatment of soil |
| WO2015034357A1 (en) | 2013-09-04 | 2015-03-12 | Ceradis B.V. | Paint composition comprising a polyelectrolyte complex |
| 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 |
| EP4531566A1 (en) | 2022-06-02 | 2025-04-09 | 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 (OSRAM) * | 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 NO NO772145A patent/NO151042C/no unknown
- 1977-06-17 FR FR7718704A patent/FR2355051A1/fr active Granted
- 1977-06-17 AT AT0429977A patent/AT371862B/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| SE7706992L (sv) | 1977-12-19 |
| DE2727317A1 (de) | 1977-12-22 |
| FI62851C (fi) | 1983-03-10 |
| NO151042B (no) | 1984-10-22 |
| FR2355051B1 (OSRAM) | 1984-01-13 |
| FI62851B (fi) | 1982-11-30 |
| NO151042C (no) | 1985-02-06 |
| NO772145L (no) | 1977-12-20 |
| SE437842B (sv) | 1985-03-18 |
| FI771511A7 (OSRAM) | 1977-12-19 |
| DE2727317C2 (de) | 1987-02-12 |
| CH630642A5 (de) | 1982-06-30 |
| US4088640A (en) | 1978-05-09 |
| ATA429977A (de) | 1982-12-15 |
| AT371862B (de) | 1983-08-10 |
| FR2355051A1 (fr) | 1978-01-13 |
Similar Documents
| Publication | Publication Date | Title |
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