JP2012530716A5 - - Google Patents
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- JP2012530716A5 JP2012530716A5 JP2012516318A JP2012516318A JP2012530716A5 JP 2012530716 A5 JP2012530716 A5 JP 2012530716A5 JP 2012516318 A JP2012516318 A JP 2012516318A JP 2012516318 A JP2012516318 A JP 2012516318A JP 2012530716 A5 JP2012530716 A5 JP 2012530716A5
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- Prior art keywords
- isoprene
- methyl
- catalyst
- bioisoprene composition
- composition
- Prior art date
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- RRHGJUQNOFWUDK-UHFFFAOYSA-N isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims 51
- 239000003054 catalyst Substances 0.000 claims 23
- -1 isoprene compound Chemical class 0.000 claims 15
- 239000000446 fuel Substances 0.000 claims 14
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-Methyl-2-butene Chemical group CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 claims 9
- IKHGUXGNUITLKF-UHFFFAOYSA-N acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 8
- 239000000126 substance Substances 0.000 claims 8
- 150000005673 monoalkenes Chemical class 0.000 claims 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 6
- 150000001875 compounds Chemical class 0.000 claims 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 6
- 230000000447 dimerizing Effects 0.000 claims 5
- QMVPMAAFGQKVCJ-SNVBAGLBSA-N (R)-(+)-citronellol Natural products OCC[C@H](C)CCC=C(C)C QMVPMAAFGQKVCJ-SNVBAGLBSA-N 0.000 claims 4
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims 4
- KXKVLQRXCPHEJC-UHFFFAOYSA-N Methyl acetate Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims 4
- ASUAYTHWZCLXAN-UHFFFAOYSA-N Prenol Chemical compound CC(C)=CCO ASUAYTHWZCLXAN-UHFFFAOYSA-N 0.000 claims 4
- 238000006471 dimerization reaction Methods 0.000 claims 4
- 229930008393 geraniol Natural products 0.000 claims 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N n-butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propanol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 4
- UHEPJGULSIKKTP-UHFFFAOYSA-N sulcatone Chemical compound CC(C)=CCCC(C)=O UHEPJGULSIKKTP-UHFFFAOYSA-N 0.000 claims 4
- GLZPCOQZEFWAFX-JXMROGBWSA-N β-Geraniol Chemical compound CC(C)=CCC\C(C)=C\CO GLZPCOQZEFWAFX-JXMROGBWSA-N 0.000 claims 4
- 229930004021 citronellol Natural products 0.000 claims 3
- 235000000484 citronellol Nutrition 0.000 claims 3
- 238000006074 cyclodimerization reaction Methods 0.000 claims 3
- 238000005984 hydrogenation reaction Methods 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 229910052763 palladium Inorganic materials 0.000 claims 3
- XMGQYMWWDOXHJM-UHFFFAOYSA-N (+-)-(RS)-limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 claims 2
- IHPKGUQCSIINRJ-CSKARUKUSA-N (E)-β-ocimene Chemical compound CC(C)=CC\C=C(/C)C=C IHPKGUQCSIINRJ-CSKARUKUSA-N 0.000 claims 2
- NEHNMFOYXAPHSD-JTQLQIEISA-N (S)-(-)-citronellal Natural products O=CC[C@@H](C)CCC=C(C)C NEHNMFOYXAPHSD-JTQLQIEISA-N 0.000 claims 2
- IHPKGUQCSIINRJ-NTMALXAHSA-N (Z)-β-ocimene Chemical compound CC(C)=CC\C=C(\C)C=C IHPKGUQCSIINRJ-NTMALXAHSA-N 0.000 claims 2
- IAEGWXHKWJGQAZ-UHFFFAOYSA-N 2,3,5-trimethylpyrazine Chemical compound CC1=CN=C(C)C(C)=N1 IAEGWXHKWJGQAZ-UHFFFAOYSA-N 0.000 claims 2
- MNDSSKADVGDFDF-UHFFFAOYSA-N 2,4,5-trimethylpyridine Chemical compound CC1=CC(C)=C(C)C=N1 MNDSSKADVGDFDF-UHFFFAOYSA-N 0.000 claims 2
- CATSNJVOTSVZJV-UHFFFAOYSA-N 2-Heptanone Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 claims 2
- XNLICIUVMPYHGG-UHFFFAOYSA-N 2-Pentanone Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 claims 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims 2
- FVCDMHWSPLRYAB-UHFFFAOYSA-N 2-ethenyl-2-methyloxirane Chemical compound C=CC1(C)CO1 FVCDMHWSPLRYAB-UHFFFAOYSA-N 0.000 claims 2
- SEPQTYODOKLVSB-UHFFFAOYSA-N 3-methylbut-2-enal Chemical compound CC(C)=CC=O SEPQTYODOKLVSB-UHFFFAOYSA-N 0.000 claims 2
- XXIKYCPRDXIMQM-UHFFFAOYSA-N 3-methylbut-2-enyl acetate Chemical compound CC(C)=CCOC(C)=O XXIKYCPRDXIMQM-UHFFFAOYSA-N 0.000 claims 2
- OCUAPVNNQFAQSM-UHFFFAOYSA-N 3-methylbut-3-enyl acetate Chemical compound CC(=C)CCOC(C)=O OCUAPVNNQFAQSM-UHFFFAOYSA-N 0.000 claims 2
- GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 claims 2
- 239000005792 Geraniol Substances 0.000 claims 2
- MLFHJEHSLIIPHL-UHFFFAOYSA-N Isoamyl acetate Chemical compound CC(C)CCOC(C)=O MLFHJEHSLIIPHL-UHFFFAOYSA-N 0.000 claims 2
- PHTQWCKDNZKARW-UHFFFAOYSA-N Isoamyl alcohol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 claims 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N Isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims 2
- HNVRRHSXBLFLIG-UHFFFAOYSA-N Isoprenyl alcohol Chemical compound CC(C)(O)C=C HNVRRHSXBLFLIG-UHFFFAOYSA-N 0.000 claims 2
- YGHRJJRRZDOVPD-UHFFFAOYSA-N Isovaleraldehyde Chemical compound CC(C)CC=O YGHRJJRRZDOVPD-UHFFFAOYSA-N 0.000 claims 2
- STNJBCKSHOAVAJ-UHFFFAOYSA-N Methacrolein Chemical compound CC(=C)C=O STNJBCKSHOAVAJ-UHFFFAOYSA-N 0.000 claims 2
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N Methyl isopropyl ketone Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 claims 2
- FUSUHKVFWTUUBE-UHFFFAOYSA-N Methyl vinyl ketone Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 claims 2
- PMJHHCWVYXUKFD-SNAWJCMRSA-N Piperylene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 claims 2
- 239000005092 Ruthenium Substances 0.000 claims 2
- 239000003377 acid catalyst Substances 0.000 claims 2
- 125000004432 carbon atoms Chemical group C* 0.000 claims 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims 2
- 229910052804 chromium Inorganic materials 0.000 claims 2
- 239000011651 chromium Substances 0.000 claims 2
- QSJXEFYPDANLFS-UHFFFAOYSA-N diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 claims 2
- WDAXFOBOLVPGLV-UHFFFAOYSA-N ethyl isobutyrate Chemical compound CCOC(=O)C(C)C WDAXFOBOLVPGLV-UHFFFAOYSA-N 0.000 claims 2
- 229940113087 geraniol Drugs 0.000 claims 2
- NPFVOOAXDOBMCE-UHFFFAOYSA-N hex-3-enyl acetate Chemical compound CCC=CCCOC(C)=O NPFVOOAXDOBMCE-UHFFFAOYSA-N 0.000 claims 2
- 229910052742 iron Inorganic materials 0.000 claims 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims 2
- 229930007650 limonene Natural products 0.000 claims 2
- 235000001510 limonene Nutrition 0.000 claims 2
- 229940087305 limonene Drugs 0.000 claims 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims 2
- 229910052707 ruthenium Inorganic materials 0.000 claims 2
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N 2,3-Dihydrogeraniol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 claims 1
- 240000003624 Cymbopogon nardus Species 0.000 claims 1
- 235000018791 Cymbopogon nardus Nutrition 0.000 claims 1
- 230000003197 catalytic Effects 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 229930003633 citronellal Natural products 0.000 claims 1
- 235000000983 citronellal Nutrition 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 229910052759 nickel Inorganic materials 0.000 claims 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims 1
- 229910052703 rhodium Inorganic materials 0.000 claims 1
- 239000010948 rhodium Substances 0.000 claims 1
Claims (28)
- (a)Bioisoprene組成物をイソプレンの二量体化に適した熱もしくは触媒条件に供してイソプレン二量体を産出してから、イソプレン二量体を触媒的に水素化して飽和C10燃料構成要素を形成すること;または
(b)(i)Bioisoprene組成物を一部水素化してイソアミレンを産出すること、(ii)イソアミレン、プロピレンおよびイソブテンからなる群から選択されるモノ−オレフィンとイソアミレンを二量体化してダイメートを形成すること、ならびに(iii)当該ダイメートを完全に水素化して燃料構成要素を産出すること、
によりBioisoprene組成物中イソプレン を非イソプレン化合物へ化学的変換することを含む、Bioisoprene組成物から燃料構成要素を産出する方法であって、当該Bioisoprene組成物は生物学的手段により得られたものである、方法 - 前記Bioisoprene組成物中イソプレンの少なくとも約95%を非イソプレン化合物に変換する、請求項1記載の方法。
- 前記Bioisoprene組成物を約150℃〜約250℃に加熱して不飽和環状イソプレン二量体を産出し、当該不飽和環状イソプレン二量体を触媒的に水素化して、飽和環状イソプレン二量体の燃料構成要素を産出する、請求項1記載の方法。
- 請求項1記載の方法であり、前記方法が以下(i)Bioisoprene組成物をイソプレンのシクロ二量体化を触媒するための触媒と接触させて、不飽和環状イソプレン二量体を産出し、当該不飽和環状イソプレン二量体を触媒的に水素化して、飽和環状イソプレン二量体の燃料構成要素を産出することとを含む請求項1記載の方法。
- イソプレンのシクロ二量体化を触媒するための前記触媒が、ニッケル触媒、鉄触媒およびクロム触媒からなる群から選択される触媒を含む、請求項4記載の方法。
- 前記Bioisoprene組成物の一部水素化工程が、Bioisoprene組成物を水素ガスおよびイソプレンの一部水素化を触媒するための触媒と接触させることを含む、請求項1記載の方法。
- イソプレンの一部水素化を触媒するための前記触媒がパラジウム触媒を含む、請求項6記載の方法。
- 前記モノ−オレフィンとイソアミレンの二量体化工程が、モノ−オレフィンの二量体化を触媒するための触媒の存在下でイソアミレンをモノ−オレフィンと接触させることを含む、請求項1記載の方法。
- モノ−オレフィンの二量体化を触媒するための前記触媒が酸触媒を含む、請求項8記載の方法。
- Bioisoprene組成物を燃料構成要素へ化学的変換する前にBioisoprene組成物からイソプレンを精製することをさらに含む、請求項1記載の方法。
- Bioisoprene組成物から燃料構成要素を産出する系であり、Bioisoprene組成物中イソプレン が、非イソプレン化合物に化学的変換され、Bioisoprene組成物を含む系であり、ならびに: (a)(i)Bioisoprene組成物中イソプレンを二量体化できる1以上の化学物質またはBioisoprene組成物中イソプレンを二量体化できる熱源;ならびに(ii)イソプレン二量体を水素化して飽和C10燃料構成要素を形成することができる触媒;または
(b)(i)Bioisoprene組成物中イソプレンを一部水素化してイソアミレンを産出することができる化学物質、(ii)イソアミレン、プロピレンおよびイソブテンからなる群から選択されるモノ−オレフィンとイソアミレンを二量体化してダイメートを形成することができる化学物質ならびに(iii)当該ダイメートを完全に水素化して燃料構成要素を産出することができる化学物質を含む系であり、当該Bioisoprene組成物は生物学的手段により得られるものである系。 - 前記Bioisoprene組成物が約2mg超のイソプレンを含み、かつ当該組成物中の全てのC5炭化水素の総重量と比べて、約99.94重量%または99.94重量%超のイソプレンを含む、請求項11記載の系。
- イソプレンを二量体化できる前記1以上の化学物質が、ルテニウム触媒、ニッケル触媒、鉄触媒およびクロム触媒からなる群から選択される触媒を含む、イソプレンのシクロ二量体化を触媒するための触媒を含む、請求項11記載の系。
- 不飽和イソプレン二量体の水素化のための前記触媒が、パラジウム触媒、ニッケル触媒、ルテニウム触媒およびロジウム触媒からなる群から選択される触媒を含む、請求項11記載の系。
- イソプレンを一部水素化できる前記化学物質がパラジウム触媒を含む、請求項11記載の系。
- イソアミレンをモノ−オレフィンと二量体化できる前記化学物質が酸触媒を含む、請求項11記載の系。
- 請求項1の方法により産出された燃料構成要素を含む、燃料組成物。
- 前記燃料組成物がイソプレンを実質的に含まない、請求項17記載の燃料組成物。
- 前記燃料組成物が−22‰を上回るまたは−32〜−24‰の範囲内のδ13C値を有する、請求項17記載の燃料組成物。
- 請求項1の方法であって、Bioisoprene組成物中の約80%以上のイソプレンが非イソプレン化合物へ変換される方法。
- 請求項1の方法であって、当該Bioisoprene組成物は、エタノール、アセトン、C5プレニルアルコール、及び10以上の炭素原子をもつイソプレノイド化合物からなる群から選択された1以上の化合物を含むものである、方法。
- 請求項1の方法であって、当該Bioisoprene組成物はエタノール、アセトン、メタノール、アセトアルデヒド、メタクロレイン、メチルビニルケトン、2−メチル−2−ビニルオキシラン、cis−及びtrans−3−メチル−1,3−ペンタジエン、及びC5プレニルアルコールからなる群から選択された1以上の化合物を含むものである、方法。
- 請求項1の方法であって、当該Bioisoprene組成物は、2−ヘプタノン、6−メチル−5−ヘプテン−2−オン、2、4、5−トリメチルピリジン、2、3、5−トリメチルピラジン、シトロネラル、アセトアルデヒド、メタンチオール、メチルアセタート、1−プロパノール、ジアセチル、2−ブタノン、2−メチル−3−ブテン−2−オール、エチルアセタート、2−メチル−1−プロパノール、3−メチル−1−ブタナール、3−メチル−2−ブタノン、1−ブタノール、2−ペンタノン、3−メチル−1−ブタノール、イソ酪酸エチル、3−メチル−2−ブテナール、ブチルアセタート、3−メチルブチルアセタート、3-メチル-3-ブテン-1-イルアセタート、3-メチル-2-ブテン-1-イルアセタート、3−ヘキセン−1−オール、3−ヘキセン−1−イルアセタート、リモネン、ゲラニオール(trans-3、7−ジメチル−2,6−オクタジエン−1−オール)、シトロネロール(3、7−ジメチル−6−オクテン−1−オール)、(E)-3、7−ジメチル−1、3、6−オクタトリエン、(Z)−3、7−ジメチル−1、3、6−オクタトリエン及び2、3−シクロヘプテノルピリジンからなる群から選択された1以上の化合物を含むものである、方法。
- 請求項1の方法であって、当該Bioisoprene組成物中の当該イソプレンは連続的に、化学的に非イソプレン化合物ヘ変換される方法。
- 請求項11の系であって、当該Bioisoprene組成物中のイソプレンの80%以上が化学的に非イソプレン化合物へ変換される系。
- 請求項11の系であって、当該Bioisoprene組成物は、エタノール、アセトン、C5プレニルアルコール、及び10以上の炭素原子をもつイソプレノイド化合物からなる群から選択される1以上の化合物を含むものである系。
- 請求項11の系であって、当該Bioisoprene組成物は、エタノール、アセトン、メタノール、アセトアルデヒド、メタクロレイン、メチルビニルケトン、2−メチル−2ビニルオキシラン、cis-及びtrans-3−メチル1,3−ペンタジエン、及びC5プレニルアルコールからなる群から選択される1以上の化合物を含むものである系。
- 請求項11の系であり、当該Bioisoprene組成物は、2−ヘプタノン、6−メチル−5−ヘプテン−2−オン、2,4,5−トリメチルピリジン、2,3,5−トリメチルピラジン、シトロネラル、アセトアルデヒド、メタンチオール、メチルアセタート、1−プロパノール、ジアセチル、2−ブタノン、2−メチル−3−ブテン−2−オール、エチルアセタート、2−メチル−1−プロパノール、3−メチル−1−ブタナール、3−メチル−2−ブタノン、1−ブタノール、2−ペンタノン、3−メチル−1−ブタノール、イソ酪酸エチル、3−メチル−2−ブテナール、ブチルアセタート、3−メチルブチルアセタート、3−メチル−3−ブテン−1−イルアセタート、3−メチル−2−ブテン−1−イルアセタート、3−ヘキセン−1−オール、3−ヘキセン−1−イルアセタート、リモネン、ゲラニオール(trans-3、7−ジメチル−2,6−オクタジエン−1−オール)、シトロネロール(3、7−ジメチル−6−オクテン−1−オール)、(E)−3,7−ジメチル−1、3、6−オクタトリエン、及び(Z)−3、7−ジメチル−1、3、6−オクタトリエン、及び2、3−シクロヘプテノルピリジンからなる群から選択される1以上の化合物を含むものである、系。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US18795909P | 2009-06-17 | 2009-06-17 | |
US61/187,959 | 2009-06-17 | ||
PCT/US2010/039088 WO2010148256A1 (en) | 2009-06-17 | 2010-06-17 | Fuel compositions comprising isoprene derivatives |
Publications (3)
Publication Number | Publication Date |
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JP2012530716A JP2012530716A (ja) | 2012-12-06 |
JP2012530716A5 true JP2012530716A5 (ja) | 2013-08-15 |
JP5448220B2 JP5448220B2 (ja) | 2014-03-19 |
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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JP2012516318A Expired - Fee Related JP5448220B2 (ja) | 2009-06-17 | 2010-06-17 | イソプレン誘導体を含む燃料組成物 |
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- 2010-06-17 CA CA2765916A patent/CA2765916A1/en not_active Abandoned
- 2010-06-17 SG SG10201507749UA patent/SG10201507749UA/en unknown
- 2010-06-17 WO PCT/US2010/039088 patent/WO2010148256A1/en active Application Filing
-
2011
- 2011-12-20 ZA ZA2011/09375A patent/ZA201109375B/en unknown
-
2013
- 2013-04-26 US US13/872,006 patent/US20140148623A1/en not_active Abandoned
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