CA2817229A1 - Gels and hydrogels - Google Patents
Gels and hydrogels Download PDFInfo
- Publication number
- CA2817229A1 CA2817229A1 CA2817229A CA2817229A CA2817229A1 CA 2817229 A1 CA2817229 A1 CA 2817229A1 CA 2817229 A CA2817229 A CA 2817229A CA 2817229 A CA2817229 A CA 2817229A CA 2817229 A1 CA2817229 A1 CA 2817229A1
- Authority
- CA
- Canada
- Prior art keywords
- hydrogel
- polymeric material
- gel
- weight
- polyglycol
- 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.)
- Abandoned
Links
- 239000000017 hydrogel Substances 0.000 title claims abstract description 411
- 239000000499 gel Substances 0.000 title claims abstract description 244
- 239000000463 material Substances 0.000 claims abstract description 428
- 229920002125 Sokalan® Polymers 0.000 claims abstract description 257
- 229920000909 polytetrahydrofuran Polymers 0.000 claims abstract description 156
- 229920000151 polyglycol Polymers 0.000 claims abstract description 124
- 239000010695 polyglycol Substances 0.000 claims abstract description 124
- 239000000203 mixture Substances 0.000 claims abstract description 68
- 238000002156 mixing Methods 0.000 claims abstract description 49
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 44
- 239000003054 catalyst Substances 0.000 claims abstract description 12
- 239000004584 polyacrylic acid Substances 0.000 claims description 248
- 238000000034 method Methods 0.000 claims description 81
- 239000001257 hydrogen Substances 0.000 claims description 56
- 229910052739 hydrogen Inorganic materials 0.000 claims description 56
- 229920001519 homopolymer Polymers 0.000 claims description 54
- 206010016807 Fluid retention Diseases 0.000 claims description 51
- 239000002689 soil Substances 0.000 claims description 51
- -1 polyethylene Polymers 0.000 claims description 45
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical group NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 35
- 239000002202 Polyethylene glycol Substances 0.000 claims description 35
- 229920001223 polyethylene glycol Polymers 0.000 claims description 35
- 229920000642 polymer Polymers 0.000 claims description 32
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 26
- 229920002678 cellulose Polymers 0.000 claims description 26
- 239000001913 cellulose Substances 0.000 claims description 26
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 26
- 238000006297 dehydration reaction Methods 0.000 claims description 24
- 239000004698 Polyethylene Substances 0.000 claims description 23
- 229920000573 polyethylene Polymers 0.000 claims description 23
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 22
- 230000003993 interaction Effects 0.000 claims description 20
- 238000010438 heat treatment Methods 0.000 claims description 15
- 239000004971 Cross linker Substances 0.000 claims description 14
- 108010010803 Gelatin Proteins 0.000 claims description 13
- 239000008273 gelatin Substances 0.000 claims description 13
- 229920000159 gelatin Polymers 0.000 claims description 13
- 235000019322 gelatine Nutrition 0.000 claims description 13
- 235000011852 gelatine desserts Nutrition 0.000 claims description 13
- 229920002134 Carboxymethyl cellulose Polymers 0.000 claims description 12
- 239000004927 clay Substances 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 239000001768 carboxy methyl cellulose Substances 0.000 claims description 10
- 235000010948 carboxy methyl cellulose Nutrition 0.000 claims description 10
- 239000008112 carboxymethyl-cellulose Substances 0.000 claims description 10
- ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 claims description 9
- MHHJQVRGRPHIMR-UHFFFAOYSA-N 1-phenylprop-2-en-1-ol Chemical compound C=CC(O)C1=CC=CC=C1 MHHJQVRGRPHIMR-UHFFFAOYSA-N 0.000 claims description 8
- XUDBVJCTLZTSDC-UHFFFAOYSA-N 2-ethenylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C=C XUDBVJCTLZTSDC-UHFFFAOYSA-N 0.000 claims description 8
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 claims description 8
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 claims description 8
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 8
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 8
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 8
- JQKJEPJLCSCBGW-UHFFFAOYSA-N dibutoxy(ethenyl)borane Chemical compound CCCCOB(C=C)OCCCC JQKJEPJLCSCBGW-UHFFFAOYSA-N 0.000 claims description 8
- FFYWKOUKJFCBAM-UHFFFAOYSA-N ethenyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC=C FFYWKOUKJFCBAM-UHFFFAOYSA-N 0.000 claims description 8
- BLCTWBJQROOONQ-UHFFFAOYSA-N ethenyl prop-2-enoate Chemical compound C=COC(=O)C=C BLCTWBJQROOONQ-UHFFFAOYSA-N 0.000 claims description 8
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 claims description 8
- 239000003337 fertilizer Substances 0.000 claims description 8
- ZQXSMRAEXCEDJD-UHFFFAOYSA-N n-ethenylformamide Chemical compound C=CNC=O ZQXSMRAEXCEDJD-UHFFFAOYSA-N 0.000 claims description 8
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 claims description 8
- 239000004793 Polystyrene Substances 0.000 claims description 7
- 229920002223 polystyrene Polymers 0.000 claims description 7
- 239000000377 silicon dioxide Substances 0.000 claims description 4
- SAMJGBVVQUEMGC-UHFFFAOYSA-N 1-ethenoxy-2-(2-ethenoxyethoxy)ethane Chemical group C=COCCOCCOC=C SAMJGBVVQUEMGC-UHFFFAOYSA-N 0.000 claims description 3
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims description 3
- 125000004386 diacrylate group Chemical group 0.000 claims description 3
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 61
- 239000000178 monomer Substances 0.000 abstract description 24
- 229920002554 vinyl polymer Polymers 0.000 abstract description 13
- 239000002245 particle Substances 0.000 abstract description 2
- 239000010408 film Substances 0.000 abstract 1
- 229920002401 polyacrylamide Polymers 0.000 description 28
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- 239000000243 solution Substances 0.000 description 21
- 238000003756 stirring Methods 0.000 description 21
- 150000003839 salts Chemical class 0.000 description 18
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 16
- 241000894007 species Species 0.000 description 15
- 241000196324 Embryophyta Species 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- 238000012360 testing method Methods 0.000 description 11
- 238000006116 polymerization reaction Methods 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 8
- 229920003266 Leaf® Polymers 0.000 description 8
- 239000004372 Polyvinyl alcohol Substances 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 229920005615 natural polymer Polymers 0.000 description 8
- 229920002451 polyvinyl alcohol Polymers 0.000 description 8
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 238000000113 differential scanning calorimetry Methods 0.000 description 6
- 125000005647 linker group Chemical group 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 238000012545 processing Methods 0.000 description 6
- BJZYYSAMLOBSDY-QMMMGPOBSA-N (2s)-2-butoxybutan-1-ol Chemical compound CCCCO[C@@H](CC)CO BJZYYSAMLOBSDY-QMMMGPOBSA-N 0.000 description 5
- 231100001261 hazardous Toxicity 0.000 description 5
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 5
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 5
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 5
- 231100000252 nontoxic Toxicity 0.000 description 5
- 230000003000 nontoxic effect Effects 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 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 4
- 230000018044 dehydration Effects 0.000 description 4
- 238000010790 dilution Methods 0.000 description 4
- 239000012895 dilution Substances 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 239000012530 fluid Substances 0.000 description 4
- 230000036571 hydration Effects 0.000 description 4
- 238000006703 hydration reaction Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- JBJWASZNUJCEKT-UHFFFAOYSA-M sodium;hydroxide;hydrate Chemical compound O.[OH-].[Na+] JBJWASZNUJCEKT-UHFFFAOYSA-M 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 229920001971 elastomer Polymers 0.000 description 3
- 230000009477 glass transition Effects 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 231100000331 toxic Toxicity 0.000 description 3
- 230000002588 toxic effect Effects 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000002028 Biomass Substances 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 2
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 2
- 102000013265 Syntaxin 1 Human genes 0.000 description 2
- 108010090618 Syntaxin 1 Proteins 0.000 description 2
- 238000012382 advanced drug delivery Methods 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 229940093476 ethylene glycol Drugs 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000002638 heterogeneous catalyst Substances 0.000 description 2
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 2
- 239000007943 implant Substances 0.000 description 2
- 238000002386 leaching Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
- 235000015097 nutrients Nutrition 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 229920001592 potato starch Polymers 0.000 description 2
- 238000004382 potting Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000012552 review Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 229920001661 Chitosan Polymers 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 240000008415 Lactuca sativa Species 0.000 description 1
- 235000003228 Lactuca sativa Nutrition 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 206010052428 Wound Diseases 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 230000003679 aging effect Effects 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000012598 cell culture matrix Substances 0.000 description 1
- 230000010261 cell growth Effects 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000011243 crosslinked material Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000012377 drug delivery Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001962 electrophoresis Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 230000001815 facial effect Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 239000002815 homogeneous catalyst Substances 0.000 description 1
- OUUQCZGPVNCOIJ-UHFFFAOYSA-N hydroperoxyl Chemical compound O[O] OUUQCZGPVNCOIJ-UHFFFAOYSA-N 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000011158 industrial composite Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 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
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 239000003305 oil spill Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 229920002959 polymer blend Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
- C08L71/08—Polyethers derived from hydroxy compounds or from their metallic derivatives
-
- 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
- C09K17/00—Soil-conditioning materials or soil-stabilising materials
- C09K17/14—Soil-conditioning materials or soil-stabilising materials containing organic compounds only
- C09K17/16—Soil-conditioning materials or soil-stabilising materials containing organic compounds only applied in a physical form other than a solution or a grout, e.g. as platelets or granules
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
- C08J3/03—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in aqueous media
- C08J3/075—Macromolecular gels
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/02—Homopolymers or copolymers of acids; Metal or ammonium salts thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
- C08L71/02—Polyalkylene oxides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2210/00—Compositions for preparing hydrogels
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2329/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal, or ketal radical; Hydrolysed polymers of esters of unsaturated alcohols with saturated carboxylic acids; Derivatives of such polymer
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2333/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers
- C08J2333/02—Homopolymers or copolymers of acids; Metal or ammonium salts thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/05—Polymer mixtures characterised by other features containing polymer components which can react with one another
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Dispersion Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Soil Sciences (AREA)
- General Life Sciences & Earth Sciences (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerisation Methods In General (AREA)
- Graft Or Block Polymers (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US41146210P | 2010-11-08 | 2010-11-08 | |
| US61/411,462 | 2010-11-08 | ||
| US41278010P | 2010-11-11 | 2010-11-11 | |
| US61/412,780 | 2010-11-11 | ||
| PCT/US2011/059837 WO2012064787A2 (en) | 2010-11-08 | 2011-11-08 | Gels and hydrogels |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2817229A1 true CA2817229A1 (en) | 2012-05-18 |
Family
ID=46051525
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2817229A Abandoned CA2817229A1 (en) | 2010-11-08 | 2011-11-08 | Gels and hydrogels |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US9850379B2 (https=) |
| EP (1) | EP2638101A4 (https=) |
| JP (1) | JP6085887B2 (https=) |
| CN (1) | CN103429643B (https=) |
| AP (1) | AP3590A (https=) |
| AU (1) | AU2011326602B2 (https=) |
| BR (1) | BR112013011340A2 (https=) |
| CA (1) | CA2817229A1 (https=) |
| CL (1) | CL2013001259A1 (https=) |
| IL (1) | IL226195A (https=) |
| MX (1) | MX346880B (https=) |
| WO (1) | WO2012064787A2 (https=) |
| ZA (1) | ZA201303997B (https=) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2013289879B2 (en) * | 2012-07-12 | 2017-04-06 | President And Fellows Of Harvard College | Slippery self-lubricating polymer surfaces |
| WO2014029029A1 (en) * | 2012-08-24 | 2014-02-27 | Moasis Inc. | Prevention of topsoil erosion with hydrogels |
| EP2890730A4 (en) * | 2012-08-30 | 2016-06-08 | Moasis Inc | POROUS GELES AND USES THEREOF |
| EP2898044A4 (en) * | 2012-09-18 | 2016-06-29 | Moasis Inc | SOLID HYDROGEL MEDIA AND METHOD FOR THE PRODUCTION AND USE THEREOF |
| JP6610864B2 (ja) * | 2015-07-22 | 2019-11-27 | 株式会社リコー | 積層造形物、臓器モデルおよびその製造方法 |
| US10442181B2 (en) | 2015-07-22 | 2019-10-15 | Ricoh Company, Ltd. | Hydrogel object and method of manufacturing hydrogel object |
| US20180311358A1 (en) * | 2015-11-05 | 2018-11-01 | Lubrizol Advanced Materials, Inc. | Thermoformable dual network hydrogel compositions |
| US10794029B2 (en) * | 2016-02-12 | 2020-10-06 | Arizona Board Of Regents On Behalf Of Arizona State University | Hydrogel biocement systems and methods |
| KR20200103688A (ko) | 2017-12-28 | 2020-09-02 | 주식회사 쿠라레 | 흡수성 수지 및 농업용 보수재 |
| MA50846A (fr) | 2018-07-27 | 2020-01-29 | Safeway Holland B V | Ensemble de plantes, récipient, zone de sol, système d'élevage, ensemble de plantes enracinées, substrat et procédés |
| NL2022028B1 (en) | 2018-11-20 | 2020-06-03 | Safeway Holland B V | A plant assembly, a container, an area of ground, a breeding system, a rooted plant assembly, a substrate and methods |
| WO2020055915A1 (en) | 2018-09-10 | 2020-03-19 | Kavazanjian Edward | Biocementation systems and methods |
| US10597801B2 (en) | 2019-02-26 | 2020-03-24 | Jonathan A. Montague | Shirt cutting jig and process for converting shirts into yarn |
| WO2020262382A1 (ja) | 2019-06-28 | 2020-12-30 | 株式会社クラレ | 吸水性共重合体 |
| CN110204777A (zh) * | 2019-07-02 | 2019-09-06 | 兰州交通大学 | 一种海藻酸复合水凝胶的制备方法 |
| US10557105B1 (en) | 2019-08-09 | 2020-02-11 | Bao Tran | Extraction systems and methods |
| CN112604667A (zh) * | 2020-11-25 | 2021-04-06 | 南京乐透思环保科技有限公司 | 泥水同治型底泥修复材料及其制备方法和应用 |
| CN113088987A (zh) * | 2021-02-25 | 2021-07-09 | 四川大学 | 基于质电耦合直接海水捕集制氢装置、系统及方法 |
| CN113788910B (zh) * | 2021-09-29 | 2023-02-10 | 浙江中医药大学 | 基于珍珠质粘土聚合物的两性离子水凝胶及其制备方法 |
| CN114736394B (zh) * | 2022-03-09 | 2025-02-14 | 中国科学院上海硅酸盐研究所 | 一种动态键自愈合功能的水凝胶组合物及其制备方法与应用 |
Family Cites Families (53)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL276742A (https=) | 1961-04-03 | |||
| AT251910B (de) | 1964-07-02 | 1967-01-25 | Ceskoslovenska Akademie Ved | Verfahren zur Herstellung von weichen, biegsamen Kontaktlinsen |
| US3332897A (en) | 1964-12-21 | 1967-07-25 | Nat Starch Chem Corp | Process of grafting monomers onto polysaccharides, and acylating product to obtain an ester |
| JPS5525523B2 (https=) | 1972-12-29 | 1980-07-07 | ||
| US3981100A (en) | 1974-04-03 | 1976-09-21 | The United States Of America As Represented By The Secretary Of Agriculture | Highly absorbent starch-containing polymeric compositions |
| FR2337738A1 (fr) | 1976-01-09 | 1977-08-05 | Nitto Chemical Industry Co Ltd | Procede pour reduire l'adhesivite d'un hydrogel d'un polymere ou copolymere d'acrylamide hydrosoluble |
| US4552940A (en) | 1984-03-02 | 1985-11-12 | Monsanto Company | Styrene viscosity modifier of grafted starch polymer solutions |
| US4873086A (en) * | 1986-03-03 | 1989-10-10 | Ciba-Geigy Corporation | Hydrogels with increased organic solvent soluble active agent loading capacity, their preparation and the use thereof |
| US4783510A (en) | 1986-06-04 | 1988-11-08 | Taiyo Fishery Co., Ltd. | Process for improving a water absorbent polyacrylic acid polymer and an improved polymer produced by said process |
| JPS63207844A (ja) | 1987-02-23 | 1988-08-29 | Hayashikane Zosen Kk | 吸水性樹脂を形成する水性組成物 |
| JPS63280001A (ja) | 1987-05-12 | 1988-11-17 | Dai Ichi Kogyo Seiyaku Co Ltd | 種子のコ−ティング組成物 |
| US5039459A (en) | 1988-11-25 | 1991-08-13 | Johnson & Johnson Vision Products, Inc. | Method of forming shaped hydrogel articles including contact lenses |
| US5079354A (en) | 1989-10-27 | 1992-01-07 | Kimberly-Clark Corporation | Method for making absorbent starch |
| US5360419A (en) | 1989-12-08 | 1994-11-01 | Kimberly-Clark Corporation | Absorbent structure possessing improved integrity |
| US5385983A (en) | 1992-11-12 | 1995-01-31 | The Dow Chemical Company | Process for preparing a water-absorbent polymer |
| US5523372A (en) | 1994-06-29 | 1996-06-04 | Uni-Star Industries Ltd. | Starch graft copolymer from prime starch |
| US5572827A (en) | 1995-05-05 | 1996-11-12 | Ball Horticultural Company | Method for applying hydrogel coatings to embryonic plants |
| US5883211A (en) | 1996-01-19 | 1999-03-16 | Aclara Biosciences, Inc. | Thermoreversible hydrogels comprising linear copolymers and their use in electrophoresis |
| KR100478742B1 (ko) | 1996-08-01 | 2005-03-28 | 메비올 가부시키가이샤 | 식물 보수용 담체 |
| US6271278B1 (en) | 1997-05-13 | 2001-08-07 | Purdue Research Foundation | Hydrogel composites and superporous hydrogel composites having fast swelling, high mechanical strength, and superabsorbent properties |
| PT1003476E (pt) | 1997-08-11 | 2005-05-31 | Alza Corp | Forma de dosagem de agente activo de libertacao prolongada adaptada para retencao gastrica |
| US6153210A (en) * | 1997-08-14 | 2000-11-28 | Periodontix, Inc. | Use of locally delivered metal ions for treatment of periodontal disease |
| US6339039B1 (en) | 1998-06-12 | 2002-01-15 | Jerker Porath | Hydrogel product for adsorption purposes |
| JP2960927B1 (ja) * | 1998-07-21 | 1999-10-12 | 株式会社日本吸収体技術研究所 | シート状高吸水性複合体の製造法 |
| EP1145621B8 (en) | 1998-11-06 | 2008-10-15 | Mebiol Inc. | Water-holding carriers for plants and water-holding materials for growing plants |
| KR100698559B1 (ko) | 1999-06-11 | 2007-03-21 | 넥타르 테라퓨틱스 에이엘, 코포레이션 | 키토산 및 폴리(에틸렌 글리콜) 또는 관련 폴리머로부터유래되는 하이드로겔 |
| JP2001152131A (ja) | 1999-11-26 | 2001-06-05 | Nippon Kayaku Co Ltd | 漏水防止方法 |
| US6557298B2 (en) | 2000-09-15 | 2003-05-06 | Monsanto Technology, Llc | Treatment of seeds with coatings containing hydrogel |
| TWI324933B (en) | 2001-06-27 | 2010-05-21 | Hisamitsu Pharmaceutical Co | Sheet-type packs |
| US6822135B2 (en) | 2002-07-26 | 2004-11-23 | Kimberly-Clark Worldwide, Inc. | Fluid storage material including particles secured with a crosslinkable binder composition and method of making same |
| US7150975B2 (en) * | 2002-08-19 | 2006-12-19 | Animas Technologies, Llc | Hydrogel composition for measuring glucose flux |
| JP4222913B2 (ja) * | 2003-09-24 | 2009-02-12 | 積水化成品工業株式会社 | 粘着性ハイドロゲル |
| JP2005264046A (ja) | 2004-03-19 | 2005-09-29 | Sony Corp | 刺激応答性ハイドロゲル、刺激応答性ハイドロゲルの製造方法、及び刺激応答性ハイドロゲルを用いた高分子アクチュエータ |
| AU2005280088A1 (en) | 2004-08-27 | 2006-03-09 | Absorbent Technologies, Inc. | Superabsorbent polymers in agricultural applications |
| DE102004042946A1 (de) | 2004-09-02 | 2006-03-09 | Basf Ag | Verfahren zur Herstellung von Polymeren durch Sprühpolymerisation |
| AU2006216655B2 (en) * | 2005-02-23 | 2012-05-31 | Zimmer Technology, Inc. | Blend hydrogels and methods of making |
| US20070134307A1 (en) * | 2005-06-24 | 2007-06-14 | Xiao T D | Antimicrobial composite and method of manufacture and use |
| JP4989884B2 (ja) | 2005-09-22 | 2012-08-01 | 積水化成品工業株式会社 | 粘着性ハイドロゲル及び粘着性ハイドロゲル製造用組成物 |
| JP4162680B2 (ja) | 2005-10-21 | 2008-10-08 | 花王株式会社 | シート状組成物 |
| US20070098799A1 (en) * | 2005-10-28 | 2007-05-03 | Zimmer, Inc. | Mineralized Hydrogels and Methods of Making and Using Hydrogels |
| US20070122362A1 (en) * | 2005-11-26 | 2007-05-31 | Giniger Martin S | Hydrogel sheets and shapes for oral care |
| JP2007146000A (ja) | 2005-11-28 | 2007-06-14 | Fuji Xerox Co Ltd | 高分子ゲル組成物及びその製造方法、光学素子 |
| US7591974B2 (en) | 2006-01-25 | 2009-09-22 | Absorbent Technologies, Inc. | Methods for producing superabsorbent polymers for use in agricultural applications |
| US20080050436A1 (en) * | 2006-08-25 | 2008-02-28 | Chu Jack F | Methods and compounds for obliteration of vessels |
| DE102006058065A1 (de) * | 2006-12-07 | 2008-06-19 | Basf Se | Bewässerungsverfahren und -system für hydrogelhaltige Böden |
| US20080236037A1 (en) | 2007-03-26 | 2008-10-02 | Rose Agri-Seed, Inc. | Planting mix compositions and methods |
| JP2008247807A (ja) * | 2007-03-30 | 2008-10-16 | Lintec Corp | ゲルパック材およびゲルパック材の製造方法 |
| US20080294237A1 (en) | 2007-04-04 | 2008-11-27 | Jack Fa-De Chu | Inflatable devices and methods to protect aneurysmal wall |
| DE102007016919A1 (de) * | 2007-04-05 | 2008-10-16 | Evonik Stockhausen Gmbh | Vorrichtung und Verfahren zur Eintragung von Bodenverbesserungsmitteln |
| US7731988B2 (en) * | 2007-08-03 | 2010-06-08 | Zimmer, Inc. | Multi-polymer hydrogels |
| CN101433503A (zh) * | 2008-12-08 | 2009-05-20 | 广东名臣有限公司 | 一种保湿组合物及其制备方法 |
| WO2012128751A1 (en) | 2011-03-21 | 2012-09-27 | Momentive Performance Materials, Inc. | Organomodified carbosiloxane monomers containing compositions and uses thereof |
| US9353019B2 (en) | 2013-01-18 | 2016-05-31 | Oms Investments, Inc. | Coated seeds |
-
2011
- 2011-11-08 CN CN201180064079.9A patent/CN103429643B/zh not_active Expired - Fee Related
- 2011-11-08 AU AU2011326602A patent/AU2011326602B2/en not_active Ceased
- 2011-11-08 AP AP2013006915A patent/AP3590A/xx active
- 2011-11-08 WO PCT/US2011/059837 patent/WO2012064787A2/en not_active Ceased
- 2011-11-08 JP JP2013537944A patent/JP6085887B2/ja active Active
- 2011-11-08 US US13/884,218 patent/US9850379B2/en active Active
- 2011-11-08 EP EP20110840415 patent/EP2638101A4/en not_active Withdrawn
- 2011-11-08 CA CA2817229A patent/CA2817229A1/en not_active Abandoned
- 2011-11-08 BR BR112013011340A patent/BR112013011340A2/pt not_active IP Right Cessation
- 2011-11-08 MX MX2013004994A patent/MX346880B/es active IP Right Grant
-
2013
- 2013-05-07 IL IL226195A patent/IL226195A/en active IP Right Grant
- 2013-05-07 CL CL2013001259A patent/CL2013001259A1/es unknown
- 2013-05-31 ZA ZA2013/03997A patent/ZA201303997B/en unknown
-
2017
- 2017-10-02 US US15/722,932 patent/US20180086913A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| IL226195A0 (en) | 2013-07-31 |
| IL226195A (en) | 2017-12-31 |
| AP2013006915A0 (en) | 2013-06-30 |
| BR112013011340A2 (pt) | 2018-05-02 |
| AP3590A (en) | 2016-02-15 |
| JP2013544929A (ja) | 2013-12-19 |
| US9850379B2 (en) | 2017-12-26 |
| AU2011326602B2 (en) | 2017-05-25 |
| WO2012064787A3 (en) | 2012-08-16 |
| US20130303665A1 (en) | 2013-11-14 |
| EP2638101A4 (en) | 2014-09-03 |
| US20180086913A1 (en) | 2018-03-29 |
| CN103429643A (zh) | 2013-12-04 |
| JP6085887B2 (ja) | 2017-03-01 |
| WO2012064787A2 (en) | 2012-05-18 |
| MX2013004994A (es) | 2013-10-17 |
| CL2013001259A1 (es) | 2013-10-04 |
| EP2638101A2 (en) | 2013-09-18 |
| AU2011326602A1 (en) | 2013-07-04 |
| ZA201303997B (en) | 2014-08-27 |
| CN103429643B (zh) | 2016-07-06 |
| MX346880B (es) | 2017-04-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US9850379B2 (en) | Gels and hydrogels | |
| Yuan et al. | Thermosensitive and photocrosslinkable hydroxypropyl chitin-based hydrogels for biomedical applications | |
| Gombotz et al. | Protein release from alginate matrices | |
| Raafat et al. | Radiation synthesis of superabsorbent CMC based hydrogels for agriculture applications | |
| Feng et al. | Synthesis and swelling behaviors of yeast-g-poly (acrylic acid) superabsorbent co-polymer | |
| US20150299975A1 (en) | Prevention of topsoil erosion with hydrogels | |
| Khurma et al. | Swelling and thermal characteristics of genipin crosslinked chitosan and poly (vinyl pyrrolidone) hydrogels | |
| Chen et al. | Preparation of CMC-poly (N-isopropylacrylamide) semi-interpenetrating hydrogel with temperature-sensitivity for water retention | |
| Jumpapaeng et al. | Novel biodegradable nanocomposite hydrogels based on biopolymers and various montmorillonite contents as high-strength coating membranes for efficient slow-release fertilizers | |
| Liu et al. | Superabsorbent Sponge and membrane prepared by polyelectrolyte complexation of Carboxymethyl cellulose/hydroxyethyl cellulose-Al3+ | |
| Wu et al. | Rational design of a multifunctional hydrogel trap for water and fertilizer capture: a review | |
| EP3880770B1 (en) | Polymeric composition for use as soil conditioner with improved water absorbency during watering of the agricultural crops | |
| Milampure et al. | Effect of salt addition towards enhancement of water retention capacity of hydrogel | |
| US20150225646A1 (en) | Porous gels and uses thereof | |
| Lodhi et al. | Recent advances in polymer hydrogels for agricultural applications | |
| Nandal et al. | Novel molasses-grafted poly (sodium acrylate) hydrogel: A sustainable solution for water retention and controlled dinotefuran release | |
| JPS6081229A (ja) | 水膨潤性架橋重合体の製法 | |
| KR102732936B1 (ko) | 액상형 토양개질용 조성물 및 이를 이용한 토양 개질방법 | |
| CN120309827B (zh) | 一种农林用复合聚氨基酸型吸水树脂及其制备方法和应用 | |
| Yang et al. | A fully bio-derived superabsorbent polymer based on sodium alginate and konjac glucomannan | |
| Vishwakarma et al. | Designing of a Macro-Porous Film using Biomaterials to Evaluate their Degradation Nature and Enhance Mechanical Behavior for Various Industrial Purposes: Agriculture and Biomedical Field | |
| JP2001114803A (ja) | 吸水剤及びその製造方法 | |
| Saranya¹ et al. | Preparation and Evaluation of Alginate Based Hydrogel for Controlled Fertilizer Delivery | |
| Bouranis et al. | Effect of the swelling ability of a novel hydrolysed acrylonitrile‐sulfonated polystyrene network on growth of tomato and lettuce seedlings | |
| BR102019018540A2 (pt) | Hidrogel para uso em solos |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20161019 |
|
| FZDE | Discontinued |
Effective date: 20190806 |