CA2883372C - Formation of [2,2] paracyclophane and related compounds and methods for the formation of polymers from cyclophanes - Google Patents
Formation of [2,2] paracyclophane and related compounds and methods for the formation of polymers from cyclophanes Download PDFInfo
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- CA2883372C CA2883372C CA2883372A CA2883372A CA2883372C CA 2883372 C CA2883372 C CA 2883372C CA 2883372 A CA2883372 A CA 2883372A CA 2883372 A CA2883372 A CA 2883372A CA 2883372 C CA2883372 C CA 2883372C
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- 238000000034 method Methods 0.000 title claims abstract description 96
- 230000015572 biosynthetic process Effects 0.000 title claims abstract description 28
- 150000001875 compounds Chemical class 0.000 title claims description 35
- 229920000642 polymer Polymers 0.000 title claims description 31
- OOLUVSIJOMLOCB-UHFFFAOYSA-N 1633-22-3 Chemical compound C1CC(C=C2)=CC=C2CCC2=CC=C1C=C2 OOLUVSIJOMLOCB-UHFFFAOYSA-N 0.000 title abstract description 8
- 238000006243 chemical reaction Methods 0.000 claims abstract description 112
- GQPLMRYTRLFLPF-UHFFFAOYSA-N Nitrous Oxide Chemical compound [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 claims abstract description 67
- 239000007789 gas Substances 0.000 claims abstract description 51
- 239000001272 nitrous oxide Substances 0.000 claims abstract description 32
- 239000008096 xylene Substances 0.000 claims abstract description 19
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims abstract description 18
- 238000004519 manufacturing process Methods 0.000 claims abstract description 7
- 239000007858 starting material Substances 0.000 claims description 40
- 239000007795 chemical reaction product Substances 0.000 claims description 38
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 32
- 239000001301 oxygen Substances 0.000 claims description 32
- 229910052760 oxygen Inorganic materials 0.000 claims description 32
- 238000009833 condensation Methods 0.000 claims description 26
- 230000005494 condensation Effects 0.000 claims description 26
- 239000000178 monomer Substances 0.000 claims description 25
- 125000003118 aryl group Chemical group 0.000 claims description 24
- 230000005291 magnetic effect Effects 0.000 claims description 23
- 239000000539 dimer Substances 0.000 claims description 21
- 230000005684 electric field Effects 0.000 claims description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
- 239000011261 inert gas Substances 0.000 claims description 17
- 238000001816 cooling Methods 0.000 claims description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- 239000000758 substrate Substances 0.000 claims description 8
- 230000003647 oxidation Effects 0.000 claims description 6
- 238000007254 oxidation reaction Methods 0.000 claims description 6
- 239000013638 trimer Substances 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 4
- 230000002708 enhancing effect Effects 0.000 claims 2
- 230000008569 process Effects 0.000 abstract description 31
- 239000012048 reactive intermediate Substances 0.000 abstract description 21
- 239000000543 intermediate Substances 0.000 abstract description 11
- 238000000197 pyrolysis Methods 0.000 abstract description 11
- 230000008021 deposition Effects 0.000 abstract description 8
- 239000012159 carrier gas Substances 0.000 abstract description 5
- 238000007429 general method Methods 0.000 abstract description 4
- 239000000463 material Substances 0.000 description 28
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 22
- 238000006116 polymerization reaction Methods 0.000 description 21
- 239000007787 solid Substances 0.000 description 19
- 239000000047 product Substances 0.000 description 18
- NRNFFDZCBYOZJY-UHFFFAOYSA-N p-quinodimethane Chemical group C=C1C=CC(=C)C=C1 NRNFFDZCBYOZJY-UHFFFAOYSA-N 0.000 description 17
- -1 poly(p-xylylene) Polymers 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 12
- 229920000052 poly(p-xylylene) Polymers 0.000 description 12
- 229910052786 argon Inorganic materials 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- 230000006872 improvement Effects 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- 230000004048 modification Effects 0.000 description 9
- 238000012986 modification Methods 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- 238000000354 decomposition reaction Methods 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- 238000000151 deposition Methods 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 229910001882 dioxygen Inorganic materials 0.000 description 6
- 230000007246 mechanism Effects 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 230000000704 physical effect Effects 0.000 description 6
- 238000006467 substitution reaction Methods 0.000 description 6
- 230000004913 activation Effects 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 230000009257 reactivity Effects 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000009834 vaporization Methods 0.000 description 5
- 230000008016 vaporization Effects 0.000 description 5
- 125000006839 xylylene group Chemical group 0.000 description 5
- GWHJZXXIDMPWGX-UHFFFAOYSA-N 1,2,4-trimethylbenzene Chemical compound CC1=CC=C(C)C(C)=C1 GWHJZXXIDMPWGX-UHFFFAOYSA-N 0.000 description 4
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 150000007524 organic acids Chemical class 0.000 description 4
- 235000005985 organic acids Nutrition 0.000 description 4
- 238000005086 pumping Methods 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 239000007790 solid phase Substances 0.000 description 4
- 238000007711 solidification Methods 0.000 description 4
- 230000008023 solidification Effects 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 150000002829 nitrogen Chemical class 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 2
- 229910000990 Ni alloy Inorganic materials 0.000 description 2
- 230000003190 augmentative effect Effects 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 125000001743 benzylic group Chemical group 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 239000007805 chemical reaction reactant Substances 0.000 description 2
- 239000004020 conductor Substances 0.000 description 2
- 239000000112 cooling gas Substances 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 239000003989 dielectric material Substances 0.000 description 2
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 2
- 230000005284 excitation Effects 0.000 description 2
- 230000004907 flux Effects 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 238000010574 gas phase reaction Methods 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 229910001026 inconel Inorganic materials 0.000 description 2
- 230000006698 induction Effects 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 150000002688 maleic acid derivatives Chemical class 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 229910003455 mixed metal oxide Inorganic materials 0.000 description 2
- 229910001172 neodymium magnet Inorganic materials 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 2
- 239000012495 reaction gas Substances 0.000 description 2
- 230000006641 stabilisation Effects 0.000 description 2
- 238000011105 stabilization Methods 0.000 description 2
- 238000005979 thermal decomposition reaction Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 229910000619 316 stainless steel Inorganic materials 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 238000005985 Hofmann elimination reaction Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000003416 augmentation Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 239000007772 electrode material Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000013461 intermediate chemical Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
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- 239000012071 phase Substances 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000011369 resultant mixture Substances 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/02—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/12—Polycyclic non-condensed hydrocarbons
- C07C15/18—Polycyclic non-condensed hydrocarbons containing at least one group with formula
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/76—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation of hydrocarbons with partial elimination of hydrogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/92—Systems containing at least three condensed rings with a condensed ring system consisting of at least two mutually uncondensed aromatic ring systems, linked by an annular structure formed by carbon chains on non-adjacent positions of the aromatic system, e.g. cyclophanes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13/599,996 | 2012-08-30 | ||
| US13/599,996 US8633289B2 (en) | 2011-08-31 | 2012-08-30 | Formation of [2,2]paracyclophane and related compounds and methods for the formation of polymers from cyclophanes |
| PCT/US2012/072335 WO2014035456A2 (en) | 2012-08-30 | 2012-12-31 | Formation of [2,2] paracyclophane and related compounds and methods for the formation of polymers from cyclophanes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2883372A1 CA2883372A1 (en) | 2014-03-06 |
| CA2883372C true CA2883372C (en) | 2019-10-15 |
Family
ID=48173049
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2883372A Active CA2883372C (en) | 2012-08-30 | 2012-12-31 | Formation of [2,2] paracyclophane and related compounds and methods for the formation of polymers from cyclophanes |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US8633289B2 (enExample) |
| EP (1) | EP2890665B1 (enExample) |
| JP (1) | JP6195926B2 (enExample) |
| KR (1) | KR101717278B1 (enExample) |
| CN (1) | CN105026352B (enExample) |
| AU (1) | AU2012388717B2 (enExample) |
| BR (1) | BR112015004274B1 (enExample) |
| CA (1) | CA2883372C (enExample) |
| IN (1) | IN2015DN01925A (enExample) |
| MX (1) | MX371156B (enExample) |
| MY (1) | MY171391A (enExample) |
| SG (1) | SG11201501399WA (enExample) |
| WO (1) | WO2014035456A2 (enExample) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8432663B2 (en) | 2007-10-05 | 2013-04-30 | Carver Scientific, Inc. | High permittivity low leakage capacitor and energy storing device and method for forming the same |
| US8940850B2 (en) | 2012-08-30 | 2015-01-27 | Carver Scientific, Inc. | Energy storage device |
| US9011627B2 (en) | 2007-10-05 | 2015-04-21 | Carver Scientific, Inc. | Method of manufacturing high permittivity low leakage capacitor and energy storing device |
| US9214281B2 (en) | 2008-10-03 | 2015-12-15 | Carver Scientific, Inc. | Very thin dielectrics for high permittivity and very low leakage capacitors and energy storing devices |
| US9214280B2 (en) | 2008-10-03 | 2015-12-15 | Carver Scientific, Inc. | Very thin dielectrics for high permittivity and very low leakage capacitors and energy storing devices |
| US10227432B2 (en) | 2011-08-31 | 2019-03-12 | Carver Scientific, Inc. | Formation of xylylene type copolymers, block polymers, and mixed composition materials |
| US10199165B2 (en) | 2012-08-30 | 2019-02-05 | Carver Scientific, Inc. | Energy storage device |
| US9899846B2 (en) | 2012-08-30 | 2018-02-20 | Carver Scientific, Inc. | Entropic energy transfer methods and circuits |
| US9805869B2 (en) | 2012-11-07 | 2017-10-31 | Carver Scientific, Inc. | High energy density electrostatic capacitor |
| WO2016048811A1 (en) * | 2014-09-26 | 2016-03-31 | Carver Scientific, Inc. | Formation of xylylene type copolymers, block polymers, and mixed composition materials |
| WO2016100260A2 (en) | 2014-12-17 | 2016-06-23 | Carver Scientific, Inc. | Energy storage device |
| TWI690133B (zh) * | 2014-12-17 | 2020-04-01 | 美商卡福科學公司 | 熵能轉換方法及電路 |
| AU2016349470B2 (en) | 2015-11-06 | 2021-07-01 | Carver Scientific, Inc. | Electroentropic memory device |
| US10249409B2 (en) | 2016-06-21 | 2019-04-02 | Schlumberger Technology Corporation | Coated conductors |
| CA3044111A1 (en) | 2016-12-02 | 2018-06-07 | Carver Scientific, Inc. | Memory device and capacitive energy storage device |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3149175A (en) * | 1960-08-22 | 1964-09-15 | Union Carbide Corp | Preparation of di-para-xylylenes |
| US3198844A (en) * | 1961-07-12 | 1965-08-03 | Minnesota Mining & Mfg | Cyclic products of para-xylylene |
| US3271417A (en) | 1963-02-06 | 1966-09-06 | Eastman Kodak Co | 1, 2-thiazetidine-3-one-1-oxides and their preparation |
| US3271471A (en) * | 1965-03-23 | 1966-09-06 | Union Carbide Corp | Dimerization process |
| US3342754A (en) | 1966-02-18 | 1967-09-19 | Union Carbide Corp | Para-xylylene polymers |
| US3616314A (en) | 1969-11-24 | 1971-10-26 | Dow Chemical Co | Electrolytic process for preparing(2.2)-paracyclophane |
| US3907748A (en) | 1974-06-17 | 1975-09-23 | University Patents Inc | Paracyclophane polymers and the production thereof |
| FR2457709A1 (fr) | 1979-05-29 | 1980-12-26 | Anvar | Nouveaux agents d'adsorption de gaz utiles en particulier pour separer de l'hydrogene d'une phase le renfermant |
| DE3240303C1 (de) | 1982-10-30 | 1984-01-19 | Merck Patent Gmbh, 6100 Darmstadt | Verfahren zur Herstellung von [2,2]-Paracyclophan |
| US4500562A (en) | 1983-03-02 | 1985-02-19 | The United States Of America As Represented By The United States Department Of Energy | Di-p-xylylene polymer and method for making the same |
| IT1191632B (it) | 1985-10-30 | 1988-03-23 | Montedison Spa | Processo per la preparazione di (2,2)-paraciolofano |
| IT1191645B (it) | 1985-12-19 | 1988-03-23 | Montedison Spa | Processo per la preparazione di (2,2)-paraciclofano e suoi derivati |
| IT1190350B (it) | 1986-06-27 | 1988-02-16 | Montedison Spa | Processo per la preparazione di (2,2)-paraciclofano e suoi derivati |
| IT1190647B (it) | 1986-06-27 | 1988-02-16 | Montedison Spa | Processo per la preparazione di (2,2)-paraciclofano e suoi derivati |
| IT1203876B (it) | 1987-04-10 | 1989-02-23 | Montedison Spa | Processo per la preparazione di (2,2)-paraciclofano e suoi derivati |
| US4849559A (en) | 1987-05-15 | 1989-07-18 | Union Carbide Corporation | Process for the preparation of dichloro-[2,2]paracyclophane |
| US4806702A (en) | 1987-05-26 | 1989-02-21 | Union Carbide Corporation | Process for the preparation of the parylene dimer |
| US4769505A (en) | 1987-07-17 | 1988-09-06 | Union Carbide Corporation | Process for the preparation of the parylene dimer |
| IT1222683B (it) | 1987-09-18 | 1990-09-12 | Montedison Spa | Processo per la preparazione del triciclo 8.2.2.2. esadeca 4,6,10,12,13,15 esaene clorurato nei nuclei benzenici |
| US5110903A (en) | 1990-12-20 | 1992-05-05 | Union Carbide Chemicals & Plastics Technology Corporation | Process for the preparation of mixed parylene dimers free of alpha-halogens |
| US5324702A (en) * | 1991-11-22 | 1994-06-28 | Amoco Corporation | Catalytic oxidation and oxidative dehydrogenation using metal-compound-loaded, deboronated hams-1b crystalline borosilicate molecular sieve compositions |
| US5266291A (en) * | 1992-05-05 | 1993-11-30 | Praxair Technology, Inc. | Packed bed arrangement for oxidation reaction system |
| US6107184A (en) * | 1998-12-09 | 2000-08-22 | Applied Materials, Inc. | Nano-porous copolymer films having low dielectric constants |
-
2012
- 2012-08-30 US US13/599,996 patent/US8633289B2/en active Active
- 2012-12-31 JP JP2015529779A patent/JP6195926B2/ja active Active
- 2012-12-31 MX MX2015002577A patent/MX371156B/es active IP Right Grant
- 2012-12-31 WO PCT/US2012/072335 patent/WO2014035456A2/en not_active Ceased
- 2012-12-31 CA CA2883372A patent/CA2883372C/en active Active
- 2012-12-31 SG SG11201501399WA patent/SG11201501399WA/en unknown
- 2012-12-31 KR KR1020157007263A patent/KR101717278B1/ko active Active
- 2012-12-31 CN CN201280076532.2A patent/CN105026352B/zh active Active
- 2012-12-31 BR BR112015004274-0A patent/BR112015004274B1/pt not_active IP Right Cessation
- 2012-12-31 EP EP12883727.5A patent/EP2890665B1/en not_active Not-in-force
- 2012-12-31 IN IN1925DEN2015 patent/IN2015DN01925A/en unknown
- 2012-12-31 AU AU2012388717A patent/AU2012388717B2/en not_active Ceased
- 2012-12-31 MY MYPI2015700600A patent/MY171391A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA2883372A1 (en) | 2014-03-06 |
| SG11201501399WA (en) | 2015-03-30 |
| AU2012388717B2 (en) | 2017-03-09 |
| KR101717278B1 (ko) | 2017-03-16 |
| MX371156B (es) | 2020-01-20 |
| JP2015529205A (ja) | 2015-10-05 |
| EP2890665A4 (en) | 2016-05-25 |
| WO2014035456A3 (en) | 2015-06-25 |
| IN2015DN01925A (enExample) | 2015-08-07 |
| KR20150044955A (ko) | 2015-04-27 |
| AU2012388717A1 (en) | 2015-03-19 |
| US20130109827A1 (en) | 2013-05-02 |
| EP2890665B1 (en) | 2019-05-22 |
| HK1212322A1 (en) | 2016-06-10 |
| BR112015004274B1 (pt) | 2021-11-09 |
| WO2014035456A2 (en) | 2014-03-06 |
| BR112015004274A2 (pt) | 2017-07-04 |
| CN105026352A (zh) | 2015-11-04 |
| EP2890665A2 (en) | 2015-07-08 |
| US8633289B2 (en) | 2014-01-21 |
| MY171391A (en) | 2019-10-10 |
| JP6195926B2 (ja) | 2017-09-13 |
| MX2015002577A (es) | 2015-06-10 |
| CN105026352B (zh) | 2018-03-16 |
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