CA2714699C - Adducts of amines and polycarboxylic acids, and filter media comprising such adducts - Google Patents
Adducts of amines and polycarboxylic acids, and filter media comprising such adducts Download PDFInfo
- Publication number
- CA2714699C CA2714699C CA2714699A CA2714699A CA2714699C CA 2714699 C CA2714699 C CA 2714699C CA 2714699 A CA2714699 A CA 2714699A CA 2714699 A CA2714699 A CA 2714699A CA 2714699 C CA2714699 C CA 2714699C
- Authority
- CA
- Canada
- Prior art keywords
- teda
- adduct
- support
- polycarboxylic acid
- filter medium
- 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 - Fee Related
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- 239000002253 acid Substances 0.000 title claims abstract description 145
- 150000001412 amines Chemical class 0.000 title abstract description 20
- 150000007513 acids Chemical class 0.000 title abstract description 17
- 238000000034 method Methods 0.000 claims abstract description 74
- 239000003054 catalyst Substances 0.000 claims abstract description 66
- QPJDMGCKMHUXFD-UHFFFAOYSA-N cyanogen chloride Chemical compound ClC#N QPJDMGCKMHUXFD-UHFFFAOYSA-N 0.000 claims abstract description 48
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 claims description 427
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 122
- 239000000203 mixture Substances 0.000 claims description 49
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 41
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 29
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 26
- 229910052751 metal Inorganic materials 0.000 claims description 25
- 239000002184 metal Substances 0.000 claims description 25
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 19
- 230000000241 respiratory effect Effects 0.000 claims description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 11
- 230000003647 oxidation Effects 0.000 claims description 10
- 238000007254 oxidation reaction Methods 0.000 claims description 10
- 239000001384 succinic acid Substances 0.000 claims description 10
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 9
- 238000005470 impregnation Methods 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 238000002156 mixing Methods 0.000 claims description 7
- 230000036571 hydration Effects 0.000 claims description 6
- 238000006703 hydration reaction Methods 0.000 claims description 6
- 230000000737 periodic effect Effects 0.000 claims description 6
- 238000000151 deposition Methods 0.000 claims description 5
- 238000001035 drying Methods 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 150000005323 carbonate salts Chemical class 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 239000007900 aqueous suspension Substances 0.000 claims 1
- 238000012360 testing method Methods 0.000 description 49
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 37
- 229910052737 gold Inorganic materials 0.000 description 37
- 239000010931 gold Substances 0.000 description 37
- 239000003570 air Substances 0.000 description 35
- 239000000463 material Substances 0.000 description 30
- 239000000243 solution Substances 0.000 description 24
- 238000001914 filtration Methods 0.000 description 23
- 229910052799 carbon Inorganic materials 0.000 description 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- -1 for example Substances 0.000 description 19
- 239000002245 particle Substances 0.000 description 17
- 230000000052 comparative effect Effects 0.000 description 14
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 13
- 239000007789 gas Substances 0.000 description 12
- 238000002441 X-ray diffraction Methods 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 11
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 10
- 238000004458 analytical method Methods 0.000 description 10
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 10
- 239000010410 layer Substances 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
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- 239000000047 product Substances 0.000 description 10
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 9
- 239000001257 hydrogen Substances 0.000 description 9
- 229910052739 hydrogen Inorganic materials 0.000 description 9
- 230000008569 process Effects 0.000 description 9
- 238000002411 thermogravimetry Methods 0.000 description 9
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- 238000000113 differential scanning calorimetry Methods 0.000 description 7
- 238000000921 elemental analysis Methods 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 150000002431 hydrogen Chemical class 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 230000032683 aging Effects 0.000 description 6
- 239000000470 constituent Substances 0.000 description 6
- 239000010949 copper Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 5
- 229910052802 copper Inorganic materials 0.000 description 5
- 238000011068 loading method Methods 0.000 description 5
- 229910052759 nickel Inorganic materials 0.000 description 5
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- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 4
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- 229960004106 citric acid Drugs 0.000 description 4
- 235000015165 citric acid Nutrition 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000004220 glutamic acid Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 229910052709 silver Inorganic materials 0.000 description 4
- 239000004332 silver Substances 0.000 description 4
- 239000011975 tartaric acid Substances 0.000 description 4
- 239000002341 toxic gas Substances 0.000 description 4
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 3
- 239000001569 carbon dioxide Substances 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
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- 239000000835 fiber Substances 0.000 description 3
- 230000006870 function Effects 0.000 description 3
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- 239000001630 malic acid Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
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- 239000011733 molybdenum Substances 0.000 description 3
- 239000002574 poison Substances 0.000 description 3
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- 238000010998 test method Methods 0.000 description 3
- 238000004627 transmission electron microscopy Methods 0.000 description 3
- 229910052720 vanadium Inorganic materials 0.000 description 3
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 238000003491 array Methods 0.000 description 2
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- 238000012512 characterization method Methods 0.000 description 2
- 238000005229 chemical vapour deposition Methods 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
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- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
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- 238000011065 in-situ storage Methods 0.000 description 1
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- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
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- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
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Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D39/00—Filtering material for liquid or gaseous fluids
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/02—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material
- B01J20/20—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material comprising free carbon; comprising carbon obtained by carbonising processes
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/30—Processes for preparing, regenerating, or reactivating
- B01J20/32—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating
- B01J20/3202—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating characterised by the carrier, support or substrate used for impregnation or coating
- B01J20/3204—Inorganic carriers, supports or substrates
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/30—Processes for preparing, regenerating, or reactivating
- B01J20/32—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating
- B01J20/3231—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating characterised by the coating or impregnating layer
- B01J20/3242—Layers with a functional group, e.g. an affinity material, a ligand, a reactant or a complexing group
- B01J20/3244—Non-macromolecular compounds
- B01J20/3246—Non-macromolecular compounds having a well defined chemical structure
- B01J20/3248—Non-macromolecular compounds having a well defined chemical structure the functional group or the linking, spacer or anchoring group as a whole comprising at least one type of heteroatom selected from a nitrogen, oxygen or sulfur, these atoms not being part of the carrier as such
- B01J20/3255—Non-macromolecular compounds having a well defined chemical structure the functional group or the linking, spacer or anchoring group as a whole comprising at least one type of heteroatom selected from a nitrogen, oxygen or sulfur, these atoms not being part of the carrier as such comprising a cyclic structure containing at least one of the heteroatoms nitrogen, oxygen or sulfur, e.g. heterocyclic or heteroaromatic structures
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/30—Processes for preparing, regenerating, or reactivating
- B01J20/32—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating
- B01J20/3291—Characterised by the shape of the carrier, the coating or the obtained coated product
- B01J20/3293—Coatings on a core, the core being particle or fiber shaped, e.g. encapsulated particles, coated fibers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/17—Amines; Quaternary ammonium compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
- C08L67/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Analytical Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Inorganic Chemistry (AREA)
- Catalysts (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Filtering Materials (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US3030408P | 2008-02-21 | 2008-02-21 | |
| US61/030,304 | 2008-02-21 | ||
| PCT/US2009/034237 WO2009105406A2 (en) | 2008-02-21 | 2009-02-17 | Adducts of amines and polycarboxylic acids, and filter media comprising such adducts |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2714699A1 CA2714699A1 (en) | 2009-08-27 |
| CA2714699C true CA2714699C (en) | 2016-03-22 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2714699A Expired - Fee Related CA2714699C (en) | 2008-02-21 | 2009-02-17 | Adducts of amines and polycarboxylic acids, and filter media comprising such adducts |
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|---|---|
| US (2) | US7902115B2 (enExample) |
| EP (1) | EP2257358B1 (enExample) |
| JP (1) | JP5384532B2 (enExample) |
| KR (1) | KR101744354B1 (enExample) |
| CN (1) | CN101945691B (enExample) |
| AU (1) | AU2009215701B2 (enExample) |
| BR (1) | BRPI0906008A2 (enExample) |
| CA (1) | CA2714699C (enExample) |
| TW (1) | TW200948473A (enExample) |
| WO (1) | WO2009105406A2 (enExample) |
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| US8535422B2 (en) * | 2009-01-26 | 2013-09-17 | St. Cloud Mining Company | Metal contaminant removal compositions and methods for making and using the same |
| WO2012088184A1 (en) * | 2010-12-20 | 2012-06-28 | E. I. Du Pont De Nemours And Company | Integrated processes for the preparation of heterocyclic aromatic polymer precursors |
| WO2012088182A2 (en) * | 2010-12-20 | 2012-06-28 | E. I. Du Pont De Nemours And Company | 2,4,5-triaminothiophenols and related compounds |
| CA2824586C (en) * | 2011-01-20 | 2019-02-26 | Scott Technologies, Inc. | Multilayered mixed bed filter for the removal of toxic gases from air streams and methods thereof |
| KR101305943B1 (ko) * | 2011-10-11 | 2013-09-12 | 웅진케미칼 주식회사 | 필터용 부직포 및 그를 이용한 필터 카트리지 |
| GB201119171D0 (en) * | 2011-11-07 | 2011-12-21 | Johnson Matthey Plc | Gas treatment |
| JP6053121B2 (ja) * | 2012-10-03 | 2016-12-27 | 花王株式会社 | ガス吸着剤 |
| USD778430S1 (en) * | 2013-11-15 | 2017-02-07 | 3M Innovative Properties Company | Filter cartridge |
| USD757247S1 (en) * | 2014-05-22 | 2016-05-24 | 3M Innovative Properties Company | Respirator cartridge |
| USD746438S1 (en) * | 2014-05-22 | 2015-12-29 | 3M Innovative Properties Company | Respirator filter cover |
| US9440775B2 (en) * | 2014-05-22 | 2016-09-13 | 3M Innovative Properties Company | Prefilter cover for bidirectional-airflow respirator cartridge |
| USD745962S1 (en) * | 2014-05-22 | 2015-12-22 | 3M Innovative Properties Company | Respirator filter retainer |
| USD757928S1 (en) * | 2014-05-22 | 2016-05-31 | 3M Innovative Properties Company | Respirator cartridge body |
| USD762845S1 (en) * | 2015-02-27 | 2016-08-02 | 3M Innovative Properties Company | Respirator cartridge |
| USD763437S1 (en) * | 2015-02-27 | 2016-08-09 | 3M Innovative Properties Company | Respirator cartridge body |
| JP6838816B2 (ja) * | 2015-04-28 | 2021-03-03 | スリーエム イノベイティブ プロパティズ カンパニー | 呼吸保護のための濾過媒体 |
| CA2994821A1 (en) * | 2015-08-06 | 2017-02-09 | 3M Innovative Properties Company | Filter media for respiratory protection |
| US10851192B2 (en) | 2015-08-11 | 2020-12-01 | Arizona Board Of Regents On Behalf Of The University Of Arizona | Dihydropyridazine-based antioxidants and uses thereof |
| US10731018B2 (en) | 2015-08-11 | 2020-08-04 | Arizona Board Of Regents On Behalf Of The University Of Arizona | Antioxidant polydihydropyridazine and polypyridazine foams from 1,2,4,5-tetrazine |
| US10619023B2 (en) | 2015-08-11 | 2020-04-14 | Arizona Board Of Regents On Behalf Of The University Of Arizona | Green chemistry method of synthesizing polymer structures that can function as a built-in antioxidant |
| WO2017172882A1 (en) * | 2016-03-29 | 2017-10-05 | The Arizona Board Of Regents On Behalf Of The University Of Arizona | Pyridazine and pyridazinone based foam filtration materials for removal of nucleophiles, electrophiles, and metals |
| WO2018005864A1 (en) | 2016-06-29 | 2018-01-04 | The Arizona Board Of Regents On Behalf Of The University Of Arizona | Method of formation of a robust network of foam through diels-alder reaction |
| CN106730464B (zh) * | 2016-12-05 | 2022-09-30 | 北京丽源博瑞环境科技有限公司 | 空气净化装置 |
| US10633517B2 (en) | 2017-03-10 | 2020-04-28 | Arizona Board Of Regents On Behalf Of The University Of Arizona | Hydrogenated tetrazine-based antioxidants and free radical reaction inhibitors and uses thereof |
| CN108339206A (zh) * | 2018-01-29 | 2018-07-31 | 山东星火科学技术研究院 | 一种化学实验防毒面罩的新型固定装置 |
| CN110433807A (zh) * | 2019-07-23 | 2019-11-12 | 山西新华化工有限责任公司 | 一种用于防护氯化氰的无氨体系载钴催化剂材料及制备 |
| US11794140B1 (en) * | 2020-05-18 | 2023-10-24 | The United States Of America As Represented By The Secretary Of The Army | Auxiliary filter for enhanced chemical protection |
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| US4215682A (en) | 1978-02-06 | 1980-08-05 | Minnesota Mining And Manufacturing Company | Melt-blown fibrous electrets |
| US4531953A (en) * | 1983-06-21 | 1985-07-30 | Calgon Corporation | Sublimation of amine compounds on activated carbon pore surfaces |
| US4801311A (en) * | 1985-03-18 | 1989-01-31 | Westvaco Corporation | Method and apparatus for removing hydrogen cyanide, cyanogen and cyanogen chloride from air |
| US4802898A (en) * | 1985-06-17 | 1989-02-07 | Westvaco Corporation | Method and apparatus for removing cyanogen chloride from air |
| US5025052A (en) | 1986-09-12 | 1991-06-18 | Minnesota Mining And Manufacturing Company | Fluorochemical oxazolidinones |
| US5062421A (en) | 1987-11-16 | 1991-11-05 | Minnesota Mining And Manufacturing Company | Respiratory mask having a soft, compliant facepiece and a thin, rigid insert and method of making |
| GB8801525D0 (en) * | 1988-01-23 | 1988-02-24 | Ciba Geigy Ag | Smoke & toxic gas suppressant composition |
| KR0148793B1 (ko) * | 1989-06-23 | 1998-10-15 | 죠셉 에이. 피세테 | 독성가스 그리고/또는 증기 흡착용 크롬비함유 함침 활성탄 |
| US5063196A (en) * | 1989-06-23 | 1991-11-05 | Calgon Carbon Corporation | Chromium-free impregnated activated carbon for adsorption of toxic gases and/or vapors |
| CA2015810A1 (en) * | 1990-05-01 | 1991-11-01 | Septimus H. Liang | Reduced pressure sublimation of amine compounds on activated carbons |
| US5344626A (en) | 1992-06-26 | 1994-09-06 | Minnesota Mining And Manufacturing Company | Dual impregnated activated carbon |
| US5462908A (en) * | 1993-06-16 | 1995-10-31 | Her Majesty The Queen In Right Of Canada, As Represented By The Minister Of National Defence | Organic amine impregnated activated carbon |
| EP0714463B1 (en) | 1993-08-17 | 1999-03-10 | Minnesota Mining And Manufacturing Company | Method of charging electret filter media |
| US6676913B2 (en) * | 1996-06-12 | 2004-01-13 | Guild Associates, Inc. | Catalyst composition and method of controlling PFC and HFC emissions |
| JPH11300138A (ja) * | 1998-04-17 | 1999-11-02 | Kawai Musical Instr Mfg Co Ltd | 浄化フィルタおよび空気浄化装置 |
| US6432175B1 (en) | 1998-07-02 | 2002-08-13 | 3M Innovative Properties Company | Fluorinated electret |
| US6344071B1 (en) * | 2000-05-22 | 2002-02-05 | 3M Innovative Properties Company | Broad spectrum filter system for filtering contaminants from air or other gases |
| US6767860B2 (en) * | 2001-05-10 | 2004-07-27 | 3M Innovative Properties Company | Sublimation of solid organic compounds onto substrate surfaces in the presence of a fluid impregnant |
| US7887889B2 (en) | 2001-12-14 | 2011-02-15 | 3M Innovative Properties Company | Plasma fluorination treatment of porous materials |
| RU2359754C2 (ru) | 2003-09-26 | 2009-06-27 | Зм Инновейтив Пропертиз Компани | Наномерные золотые катализаторы, активаторы, твердые носители и соответствующие методики, применяемые для изготовления таких каталитических систем, особенно при осаждении золота на твердый носитель с использованием конденсации из паровой фазы |
| US20060096911A1 (en) * | 2004-11-08 | 2006-05-11 | Brey Larry A | Particle-containing fibrous web |
| US8058202B2 (en) * | 2005-01-04 | 2011-11-15 | 3M Innovative Properties Company | Heterogeneous, composite, carbonaceous catalyst system and methods that use catalytically active gold |
| DE102005023856A1 (de) * | 2005-05-24 | 2006-11-30 | Basf Ag | Verfahren zur Herstellung poröser metall-organischer Gerüstmaterialien |
| US20070027079A1 (en) | 2005-07-27 | 2007-02-01 | Lorn Leitman | GHRP 2 strips |
| JP2009506761A (ja) * | 2005-09-05 | 2009-02-19 | ローディア アセトウ ゲーエムベーハー | タバコの煙用フィルタ又はフィルタエレメント、そのようなフィルタ又はフィルタエレメントを含むシガレット、及びそのようなフィルタ又はフィルタエレメントを作製する方法 |
| US20080026041A1 (en) * | 2005-09-12 | 2008-01-31 | Argonide Corporation | Non-woven media incorporating ultrafine or nanosize powders |
| EP2089134A4 (en) | 2006-10-30 | 2011-11-30 | 3M Innovative Properties Co | A FILTER ENVIRONMENT CONTAINING AN EFFECTIVE FILTERING AGENT FOR THE REMOVAL OF CONTAMINANTS CONTAINING CYANATED COMPOUNDS HAVING IMPROVED COMPATIBILITY WITH AMINE-SENSITIVE IMPREGNATING PRODUCTS AND AMINE-SENSITIVE SUBSTRATES |
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2009
- 2009-02-17 JP JP2010547703A patent/JP5384532B2/ja not_active Expired - Fee Related
- 2009-02-17 CN CN2009801058219A patent/CN101945691B/zh not_active Expired - Fee Related
- 2009-02-17 CA CA2714699A patent/CA2714699C/en not_active Expired - Fee Related
- 2009-02-17 AU AU2009215701A patent/AU2009215701B2/en not_active Ceased
- 2009-02-17 EP EP09712224.6A patent/EP2257358B1/en not_active Not-in-force
- 2009-02-17 BR BRPI0906008-1A patent/BRPI0906008A2/pt active Search and Examination
- 2009-02-17 WO PCT/US2009/034237 patent/WO2009105406A2/en not_active Ceased
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- 2009-02-19 US US12/388,647 patent/US7902115B2/en not_active Expired - Fee Related
- 2009-02-20 TW TW098105545A patent/TW200948473A/zh unknown
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2011
- 2011-02-01 US US13/018,863 patent/US8178470B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| WO2009105406A3 (en) | 2009-10-15 |
| EP2257358B1 (en) | 2018-08-15 |
| BRPI0906008A2 (pt) | 2015-06-30 |
| AU2009215701A1 (en) | 2009-08-27 |
| CN101945691A (zh) | 2011-01-12 |
| EP2257358A4 (en) | 2016-07-20 |
| CN101945691B (zh) | 2013-11-06 |
| WO2009105406A2 (en) | 2009-08-27 |
| JP5384532B2 (ja) | 2014-01-08 |
| US7902115B2 (en) | 2011-03-08 |
| KR20100134582A (ko) | 2010-12-23 |
| TW200948473A (en) | 2009-12-01 |
| JP2011517614A (ja) | 2011-06-16 |
| US20090215618A1 (en) | 2009-08-27 |
| US20110171076A1 (en) | 2011-07-14 |
| EP2257358A2 (en) | 2010-12-08 |
| CA2714699A1 (en) | 2009-08-27 |
| AU2009215701B2 (en) | 2011-11-03 |
| KR101744354B1 (ko) | 2017-06-07 |
| US8178470B2 (en) | 2012-05-15 |
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