WO2018022228A1 - Water based sealer with superior durability - Google Patents
Water based sealer with superior durability Download PDFInfo
- Publication number
- WO2018022228A1 WO2018022228A1 PCT/US2017/038913 US2017038913W WO2018022228A1 WO 2018022228 A1 WO2018022228 A1 WO 2018022228A1 US 2017038913 W US2017038913 W US 2017038913W WO 2018022228 A1 WO2018022228 A1 WO 2018022228A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- component
- sealer composition
- acrylic resin
- sealer
- substrate
- Prior art date
Links
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims abstract description 22
- 239000000203 mixture Substances 0.000 claims abstract description 62
- 239000000758 substrate Substances 0.000 claims abstract description 44
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 36
- 229920000178 Acrylic resin Polymers 0.000 claims abstract description 29
- 239000004925 Acrylic resin Substances 0.000 claims abstract description 29
- 239000004971 Cross linker Substances 0.000 claims abstract description 21
- 239000004593 Epoxy Substances 0.000 claims abstract description 21
- 229910000077 silane Inorganic materials 0.000 claims abstract description 21
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims abstract description 19
- 238000000576 coating method Methods 0.000 claims description 36
- 239000011248 coating agent Substances 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 16
- -1 defoamers Substances 0.000 claims description 12
- 239000003973 paint Substances 0.000 claims description 7
- 229920000642 polymer Polymers 0.000 claims description 7
- 239000000654 additive Substances 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 claims description 5
- 239000004908 Emulsion polymer Substances 0.000 claims description 4
- 239000003139 biocide Substances 0.000 claims description 4
- 239000002270 dispersing agent Substances 0.000 claims description 4
- 239000001023 inorganic pigment Substances 0.000 claims description 4
- 239000012860 organic pigment Substances 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 239000006254 rheological additive Substances 0.000 claims description 4
- 239000004094 surface-active agent Substances 0.000 claims description 4
- 229920000058 polyacrylate Polymers 0.000 claims description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 2
- 239000002969 artificial stone Substances 0.000 claims description 2
- 238000009472 formulation Methods 0.000 claims description 2
- 239000012855 volatile organic compound Substances 0.000 claims description 2
- 230000000996 additive effect Effects 0.000 claims 2
- 239000000523 sample Substances 0.000 description 13
- 229910052782 aluminium Inorganic materials 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- 239000000470 constituent Substances 0.000 description 5
- 239000006224 matting agent Substances 0.000 description 5
- 0 C[C@@]1C*CCC1 Chemical compound C[C@@]1C*CCC1 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- 239000004606 Fillers/Extenders Substances 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 239000008199 coating composition Substances 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 239000003550 marker Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000010434 nepheline Substances 0.000 description 2
- 229910052664 nepheline Inorganic materials 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 239000013074 reference sample Substances 0.000 description 2
- 238000007789 sealing Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000010435 syenite Substances 0.000 description 2
- NIJWSVFNELSKMF-UHFFFAOYSA-N (2,3,4,5,6-pentafluorophenyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=C(F)C(F)=C(F)C(F)=C1F NIJWSVFNELSKMF-UHFFFAOYSA-N 0.000 description 1
- RFOWDPMCXHVGET-UHFFFAOYSA-N (2,3,4,5,6-pentafluorophenyl) prop-2-enoate Chemical compound FC1=C(F)C(F)=C(OC(=O)C=C)C(F)=C1F RFOWDPMCXHVGET-UHFFFAOYSA-N 0.000 description 1
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
- MLBWTXHUVGBPNL-UHFFFAOYSA-N 1-pyridin-4-ylheptan-1-one Chemical compound CCCCCCC(=O)C1=CC=NC=C1 MLBWTXHUVGBPNL-UHFFFAOYSA-N 0.000 description 1
- QTKPMCIBUROOGY-UHFFFAOYSA-N 2,2,2-trifluoroethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(F)(F)F QTKPMCIBUROOGY-UHFFFAOYSA-N 0.000 description 1
- VBHXIMACZBQHPX-UHFFFAOYSA-N 2,2,2-trifluoroethyl prop-2-enoate Chemical compound FC(F)(F)COC(=O)C=C VBHXIMACZBQHPX-UHFFFAOYSA-N 0.000 description 1
- ZNJXRXXJPIFFAO-UHFFFAOYSA-N 2,2,3,3,4,4,5,5-octafluoropentyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(F)(F)C(F)(F)C(F)(F)C(F)F ZNJXRXXJPIFFAO-UHFFFAOYSA-N 0.000 description 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- REEBWSYYNPPSKV-UHFFFAOYSA-N 3-[(4-formylphenoxy)methyl]thiophene-2-carbonitrile Chemical compound C1=CC(C=O)=CC=C1OCC1=C(C#N)SC=C1 REEBWSYYNPPSKV-UHFFFAOYSA-N 0.000 description 1
- ZLQGITSKRNWIOT-UHFFFAOYSA-N 5-(dimethylamino)furan-2-carbaldehyde Chemical compound CN(C)C1=CC=C(C=O)O1 ZLQGITSKRNWIOT-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 1
- IRXUFAGEXMCXHZ-UHFFFAOYSA-N bis(2,2,2-trifluoroethyl) 2-methylidenebutanedioate Chemical compound FC(F)(F)COC(=O)CC(=C)C(=O)OCC(F)(F)F IRXUFAGEXMCXHZ-UHFFFAOYSA-N 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D133/00—Coating compositions based on 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 only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
- C09D133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09D133/062—Copolymers with monomers not covered by C09D133/06
- C09D133/066—Copolymers with monomers not covered by C09D133/06 containing -OH groups
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D7/00—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials
- B05D7/24—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials for applying particular liquids or other fluent materials
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D2210/00—Applying material to more than three types of substrate materials
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D2502/00—Acrylic polymers
Definitions
- the present invention is related to water based coatings from which a sealing coating can be formed.
- Paints and related coatings are ubiquitous finding numerous applications for both aesthetic and functional applications. In many applications, coatings are applied to improve the aesthetic appeal of a surface by providing a uniform and pleasing appearance. In other applications, coatings are used has a clear coat on various substrates to provide some degree of protection. In additional to the visual effects, paint coatings can also be applied to porous substrates such as concrete and masonry for sealing purposes.
- the present invention solves one or more problems of the prior art by providing a sealer composition for forming a coating on a substrate.
- the sealer composition includes a first component and a second component.
- the first component includes water and a hydroxyl functionalized acrylic resin.
- the second component includes an epoxy silane cross-linker. Characteristically, the first component and second component are mixed prior to application of the sealer composition to a substrate.
- a sealer composition for forming a coating on a substrate is provided.
- the sealer composition includes a first component and a second component.
- the first component includes water and a hydroxyl functionalized acrylic resin.
- the second component includes an epoxy silane cross-linker selected from the group consisting of:
- the first component and second component are mixed at most 40 hours prior to application of the sealer composition to a substrate.
- a method of applying the sealer composition set forth above to a substrate includes a first component and a second component.
- the first component includes water and a hydroxyl functionalized acrylic resin.
- the second component includes an epoxy silane cross-linker. Additional details of the first and second components and their constituents are set forth above.
- the sealer composition is applied by mixing the first component and the second component to form a coating mixture.
- the substrate is coated with the coating mixture to form an uncured coated substrate.
- the uncured coated substrate is allowed to cure to form a sealer coating on the substrate.
- the sealer composition of the present invention produces coatings exhibits improved scrub and scratch resistance when compared to prior art compositions.
- Figure 1 provides a bar chart comparing the scrub resistance of coating examples of the present invention compared to several prior art coatings.
- percent, "parts of,” and ratio values are by weight; the term “polymer” includes “oligomer,” “copolymer,” “terpolymer,” and the like; molecular weights provided for any polymers refers to weight average molecular weight unless otherwise indicated; the description of a group or class of materials as suitable or preferred for a given purpose in connection with the invention implies that mixtures of any two or more of the members of the group or class are equally suitable or preferred; description of constituents in chemical terms refers to the constituents at the time of addition to any combination specified in the description, and does not necessarily preclude chemical interactions among the constituents of a mixture once mixed; the first definition of an acronym or other abbreviation applies to all subsequent uses herein of the same abbreviation and applies mutatis mutandis to normal grammatical variations of the initially defined abbreviation; and, unless expressly stated to the contrary, measurement of a property is determined by the same technique as previously or later referenced for the same property.
- a sealer composition for forming a coating on a substrate includes a first component and a second component.
- the first component includes water and a hydroxyl functionalized acrylic resin.
- the pH of the first component is less than 7.
- the pH of the first component is from 4 to 6.
- the second component includes an epoxy silane cross-linker.
- the first component and second component are mixed prior to application of the sealer composition to a substrate.
- the first and second components are mixed at most 40 hours prior to application of the sealer composition to a substrate.
- the first and second components are mixed immediately prior to 40 hours prior to application of the sealer composition to a substrate.
- the first and second components are mixed up to, in increasing order of preference, 40, 30, 20, 10, 5, 3, 2, 1, or 0.5 hours prior to application of the sealer composition to a substrate.
- the hydroxyl functionalized acrylic resin includes a hydroxyl functional acrylic polymer.
- the hydroxyl functionalized acrylic resin is a solution polymer.
- the hydroxyl functionalized acrylic resin is an emulsion polymer.
- Suitable hydroxyl functionalized acrylic resins are formed from hydroxyl derivatives of the monomers selected from the group consisting of methacrylate, methyl acrylate, ethyl acrylate, 2-chloroethyl vinyl ether, 2-ethylhexyl acrylate, hydroxyethyl methacrylate, butyl acrylate, butyl methacrylate, trimethylolpropane triacrylate, pentafluorophenyl methacrylate, pentafluorophenyl acrylate, 1, 1,1,3,3,3-hexafluoroisopropyl acrylate, bis-(2,2,2-trifluoroethyl) itaconate, bis-(l, 1, 1, 3,3,3- hexafluoroisopropyl), lH, lH,3H-hexafluorobutyl acrylate, lH,lH,7H-dodecafluoroheptyl methacrylate, 2,2,
- the sealer composition includes an epoxy alkoxy silane cross- linker.
- suitable epoxy alkoxy silane cross-linker include, but are not limited to:
- the hydroxyl functionalized acrylic resin is present in an amount of 75 to 95 percent of the dry weight of the combined weight of the first component and the second component, the epoxy silane cross-linker is present in an amount of 5 to 25 percent of the dry weight of the combined weight of the first component and the second component with the balance being water.
- the hydroxyl functionalized acrylic resin is present in an amount of 80 to 90 percent of the dry weight of the combined weight of the first component and the second component and the epoxy silane cross-linker is present in an amount of 10 to 20 percent of the dry weight of the combined weight of the first component and the second component with the balance being water.
- the first component further includes one or more additives selected from the group consisting of rheology modifiers, surfactants, defoamers, organic solvents, pH adjusters, UV stablizers, dispersants, coalescents, biocides, inorganic pigment, organic pigments, and combinations thereof.
- the hydroxyl functionalized acrylic resin is present in an amount of 75 to 95 percent of the dry weight of the combined weight of the first component and the second component
- the epoxy silane cross-linker is present in an amount of 5 to 25 percent of the dry weight of the combined weight of the first component and the second component
- the additives being present in an amount of 0.1 to 10 percent of the combined weight of the total formulation with the balance being water.
- volatile organic compounds are present in an amount less than 100 g/liter.
- the sealer composition can include a matting agent to adjust the gloss to a lower sheen.
- the matting agent can be any extender pigment that does not add opacity to the clear coat, such as silicas, nepheline syenite, and the like.
- the matting agent is present in an amount from about 0.2 to 8 percent of the dry weight of the combined weight of the first component and the second component.
- a method of applying the sealer compositions set forth above to a substrate includes a first component and a second component.
- the first component includes water and a hydroxyl functionalized acrylic resin.
- the second component includes an epoxy silane cross-linker. Additional details of the first and second components and their constituents are set forth above.
- the sealer composition is applied by mixing the first component and the second component to form a coating mixture.
- the substrate is coated with the coating mixture to form an uncured coated substrate.
- the uncured coated substrate is allowed to cure to form a sealer coating on the substrate.
- the substrate is a concrete or masonry substrate.
- the substrate is a pre-coated substrate with paint, coatings or stains, the sealer coating being a clear topcoat.
- the substrate is metal.
- the substrate is pavement, artificial stone and stucco.
- the sealer coating is topcoat over a paint or stain.
- the sealer coating is a dry erase coating.
- Table 1 provides compositions for four examples of embodiments of the invention. It should be appreciated that the resin and silane choices are not limited to the listed examples.
- the gloss was measured on 3 mil drawdown on Leneta 3B card with BYK-Gardner gloss meter.
- a matting agent is added into the high gloss formula to adjust the gloss to a lower sheen as shown in the compositions of Table 2.
- the matting agent can be any extender pigment that does not add opacity to the clear coat, such as silicas, nepheline syenite etc.
- the clear coat can be used on top of coated or uncoated surfaces, and exhibits excellent dry erase properties, while the other products in the sealer category do not have this property. This indicates the clear coat can be used as a dry erase coating.
- Figure 1 provides a bar chart comparing the scrub resistance of coating examples of the present invention compared to several prior art coatings.
- the scrub resistance is determined according to ASTM D2486; the entire disclosure of which is incorporated by reference. The results are reported as a percent with respect to a reference sample. The percent is the number of cycles to failure for the sample being measured divided by the number of cycles to failure for a reference sample time 100 percent.
- the coatings of the invention have a scrub resistance of 900 percent or greater.
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Materials Engineering (AREA)
- Sealing Material Composition (AREA)
- Paints Or Removers (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Description
Claims
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
MX2019001188A MX2019001188A (en) | 2016-07-29 | 2017-06-23 | Water based sealer with superior durability. |
EP17834925.4A EP3491085B1 (en) | 2016-07-29 | 2017-06-23 | Water based sealer with superior durability |
AU2017301461A AU2017301461B2 (en) | 2016-07-29 | 2017-06-23 | Water based sealer with superior durability |
CA3031647A CA3031647C (en) | 2016-07-29 | 2017-06-23 | Water based sealer with superior durability |
CN201780056250.9A CN109689808A (en) | 2016-07-29 | 2017-06-23 | Water base sealant with exceptional durability |
BR112019001761-5A BR112019001761B1 (en) | 2016-07-29 | 2017-06-23 | SEALING COMPOSITIONS |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US15/223,929 US10934449B2 (en) | 2016-07-29 | 2016-07-29 | Water based sealer with superior durability |
US15/223,929 | 2016-07-29 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2018022228A1 true WO2018022228A1 (en) | 2018-02-01 |
Family
ID=61012150
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US2017/038913 WO2018022228A1 (en) | 2016-07-29 | 2017-06-23 | Water based sealer with superior durability |
Country Status (7)
Country | Link |
---|---|
US (2) | US10934449B2 (en) |
EP (1) | EP3491085B1 (en) |
CN (1) | CN109689808A (en) |
AU (1) | AU2017301461B2 (en) |
CA (1) | CA3031647C (en) |
MX (1) | MX2019001188A (en) |
WO (1) | WO2018022228A1 (en) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP7398927B2 (en) | 2018-11-30 | 2023-12-15 | 中国塗料株式会社 | Sealing agent |
CN109988500A (en) * | 2019-04-29 | 2019-07-09 | 重庆亘祥科技有限公司 | A kind of high resiliency super low-temperature resistant water paint |
WO2021026001A1 (en) | 2019-08-02 | 2021-02-11 | Building Materials Investment Corporation | Water-resistant acrylic coatings |
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EP0562283A2 (en) | 1992-03-23 | 1993-09-29 | OECE Industrie Chimiche Spa | Three-component water-based varnish for glass for interior use |
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KR20060079517A (en) | 2004-12-31 | 2006-07-06 | 주식회사 케이씨씨 | Paint composition for coating non-metal |
US20070042192A1 (en) * | 2005-08-18 | 2007-02-22 | Nguyen Van N | Coated substrate having one or more cross-linked interfacial zones |
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WO1997022646A1 (en) | 1995-12-19 | 1997-06-26 | Ppg Industries, Inc. | Polyisocyanate cured ultradurable glossy coating compositions |
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2016
- 2016-07-29 US US15/223,929 patent/US10934449B2/en active Active
-
2017
- 2017-06-23 CA CA3031647A patent/CA3031647C/en active Active
- 2017-06-23 AU AU2017301461A patent/AU2017301461B2/en active Active
- 2017-06-23 WO PCT/US2017/038913 patent/WO2018022228A1/en active Application Filing
- 2017-06-23 CN CN201780056250.9A patent/CN109689808A/en active Pending
- 2017-06-23 MX MX2019001188A patent/MX2019001188A/en unknown
- 2017-06-23 EP EP17834925.4A patent/EP3491085B1/en active Active
-
2021
- 2021-01-26 US US17/158,727 patent/US11572487B2/en active Active
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Also Published As
Publication number | Publication date |
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AU2017301461B2 (en) | 2021-10-07 |
EP3491085A4 (en) | 2020-03-04 |
EP3491085B1 (en) | 2022-09-14 |
AU2017301461A1 (en) | 2019-03-14 |
CN109689808A (en) | 2019-04-26 |
CA3031647A1 (en) | 2018-02-01 |
MX2019001188A (en) | 2019-08-14 |
CA3031647C (en) | 2023-03-07 |
US11572487B2 (en) | 2023-02-07 |
US20210147705A1 (en) | 2021-05-20 |
EP3491085A1 (en) | 2019-06-05 |
BR112019001761A2 (en) | 2019-05-07 |
US20180030307A1 (en) | 2018-02-01 |
US10934449B2 (en) | 2021-03-02 |
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