JP2023504849A - バイオベースの材料をアップグレードするための方法およびアップグレードされた材料 - Google Patents
バイオベースの材料をアップグレードするための方法およびアップグレードされた材料 Download PDFInfo
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Abstract
Description
(A)バイオベースの新鮮なフィード材料の総計の重量に対して2wt.-%~60wt.-%のグリセロール当量を有するバイオ再生可能なオイルおよび/または脂肪のバイオベースの新鮮なフィード材料を提供する工程、
(B)水素化処理された流出物を得るために、バイオベースの新鮮なフィード材料および任意には希釈剤を含む水素化処理フィードを、金属硫化物触媒および水素(H2)の存在下でHDOを含む水素化処理へと付す工程であって、該水素化処理フィードがS元素として算出されて10~10000wt.-ppmの硫黄含有化合物を含む工程、
(C)H2、バイオプロパン、H2O、H2S、CO2、およびCOを含む気体の水素化処理された材料、ならびにパラフィン系炭化水素を含む液体の水素化処理された材料を提供するように、該水素化処理された流出物を気-液分離に付す工程、
(D)任意の第2の水素化処理の後に、該液体の水素化処理された材料を分画に付し、および、少なくともディーゼルおよび/またはケロシン範囲のパラフィン系炭化水素材料を回収する工程、
(E)H2SおよびCO2の枯渇した気体ストリームを得るために、該気体の水素化処理された材料をH2SおよびCO2を除去するための精製工程に付す工程、
(F)乾燥されたH2SおよびCO2の枯渇した気体ストリームを得るために、該H2SおよびCO2の枯渇した気体ストリームを、H2回収および乾燥に付す工程、
(G)バイオ-プロパン気体組成物を回収するために、該乾燥されたH2S、CO2およびH2の枯渇した気体ストリームを分画し、および任意には、液化されたバイオ-プロパン組成物を得るために該バイオ-プロパン気体組成物を圧縮する工程
を含む方法。
該バイオベースの新鮮なフィード材料が、4wt.-%~50wt.-%、好ましくは6wt.-%~40wt.-%、または7wt.-%wt.-%~30wt.-%であるグリセロール当量を有する項目1または2に記載の方法。
40℃で1200~1500kPaの蒸気圧および15℃で495~520kg/m3の密度を有する液化されたバイオ-プロパン組成物であって、
少なくとも94wt.-%のバイオ-プロパン、
最大で2000wt.-ppmのCO2、
最大で1000wt.-ppmのCO、
S元素として算出されて、最大で15wt.-ppmのS含有化合物、
最大で1500wt.-ppmの不飽和炭化水素、
最大で5.5wt.-%の3つ以上の炭素原子を有する炭化水素(C3+炭化水素)、ここで、(液化されたバイオプロパン組成物に対して)最大1.4wt.-%が、5つ以上の炭素原子を有する炭化水素である
を含むバイオ-プロパン組成物。
液化されたバイオプロパン組成物は、完全に再生可能なバイオプロパン組成物であってもよく、また、再生可能な材料と化石材料とのブレンドであるバイオ-プロパン組成物であってもよい。液化されたバイオ-プロパン組成物は、好ましくは、少なくとも5%、より好ましくは少なくとも10%、少なくとも50%、少なくとも75%、少なくとも90%、または約100%の生物起源炭素含有量(後述する)を有する。
40℃で1250~1450kPa、好ましくは1300~1430kPaの蒸気圧を有し;および/または
15℃で500~515kg/m3、より好ましくは500~510kg/m3の密度を有し;および/または
少なくとも95wt.-%のバイオプロパン、好ましくは少なくとも96wt.-%のバイオプロパンを含み;および/または
最大で1800wt.-ppm、好ましくは最大で1500wt.-ppm、より好ましくは最大で1000wt.-ppm、さらに好ましくは最大で500wt.-ppmのCO2(二酸化炭素)を含み;および/または
最大で500wt.-ppm、好ましくは最大で100wt.-ppm、より好ましくは最大で50wt.-ppmのCO(一酸化炭素)を含む
バイオ-プロパン組成物。
(A)バイオベースの新鮮なフィード材料の総重量に対して2wt.-%~60wt.-%のグリセロール当量を有するバイオ再生可能なオイルおよび/または脂肪のバイオベースの新鮮なフィード材料を提供する工程、
(B)水素化処理された流出物を得るために、バイオベースの新鮮なフィード材料および任意には希釈剤を含む水素化処理フィードを金属硫化物触媒および水素(H2)の存在下でHDOを含む水素化処理へと付す工程であって、該水素化処理フィードがS元素として算出されて10~10000wt.-ppmの硫黄含有化合物を含む工程、
(C)H2、バイオプロパン、H2O、H2S、CO2、およびCOを含む気体の水素化処理された材料、ならびにパラフィン系炭化水素を含む液体の水素化処理された材料を提供するように、該水素化処理された流出物を気-液分離に付す工程、
(D)任意の第2の水素化処理の後に、該液体の水素化処理された材料を分画に付し、および、少なくともディーゼルおよび/またはケロシン範囲のパラフィン系炭化水素材料を回収する工程、
(E)H2SおよびCO2の枯渇した気体ストリームを得るために、該気体の水素化処理された材料をH2SおよびCO2を除去するための精製工程に付す工程、
(F)乾燥されたH2SおよびCO2の枯渇した気体ストリームを得るために、該H2SおよびCO2の枯渇した気体ストリームを、H2回収および乾燥に付す工程、
(G)バイオ-プロパン気体組成物を回収するために、該乾燥されたH2S、CO2およびH2の枯渇した気体ストリームを分画し、および任意には、液化されたバイオ-プロパン組成物を得るために該バイオ-プロパン気体組成物を圧縮する工程、
(H)バイオ-プロピレンを含む脱水素化流出物を得るために、バイオ-プロパンガス組成物および/または液化されたバイオ-プロパン組成物の少なくとも一部を、触媒的脱水素を含む変換に付す工程、
(I)該脱水素化流出物から、バイオ-プロピレン組成物を回収し、および任意には精製する工程
を含む方法。
グリセロール当量=
(グリセロールベース部位のモル量[mol])×89.07g/mol/
(バイオベースの新鮮なフィード材料の総計の重量[g])
本発明の方法は、バイオ再生可能なオイルおよび/または脂肪のバイオベースの新鮮なフィード材料を提供する工程、すなわち準備工程(A)を提供する。
本発明の方法は、前処理工程(A’)を含み得る。
本発明の方法は、水素化処理された流出物を提供するための、バイオベースの新鮮なフィード材料、任意の希釈剤を含む水素化処理フィードを、金属硫化物触媒および水素(H2)の存在下でHDOを含む水素化処理に付す水素化処理ステップ(B)を含む。
1)水素化脱酸素(HDO)、酸素結合の水素化-酸素をH2Oとして除去する、
2)酸素がCO2の形で除去される脱炭酸、および
3)酸素がCOの形で除去される脱カルボニル化。
本発明の方法は、気-液分離工程(C)を含む。
工程(D)は、液体の水素化処理された材料を、任意的な第2の水素化処理の後に分画に付すこと、および、少なくともディーゼルおよび/またはケロシン範囲のパラフィン系炭化水素材料、特には自動車ディーゼル燃料のEN 590要件を満たすディーゼル範囲のパラフィン系炭化水素材料、および/または、航空タービン燃料の要件を満たす、ASTM D7566-16b、Annex A2を満たすケロシン範囲のパラフィン系炭化水素材料を回収することを含む。
気体の水素化処理された材料の組成に依存して、それが水素から分離され、および乾燥される前に、精製工程(E)を行うべきである。
本発明のプロセスは、工程(E)で提供されるH2SおよびCO2が枯渇したガス流を使用するH2回収および乾燥工程(F)を含む。
本発明の実施形態による水素を回収する(および同時にH2が枯渇した気体流を提供する)方法は、膜を提供する工程を含む。膜は、供給側および透過側を有する。膜は、水素の大部分を優先的に透過し、プロパンの大部分を拒むという点で、プロパンよりも水素に対して選択的であることによって機能する。存在する場合、一または複数のさらなるガスはCOおよび軽質炭化水素(プロパンと共に拒まれる)、H2O、CO2、H2SおよびNH3(拒まれるかまたは膜のタイプならびに例えば温度および圧力などの条件に依存して部分的にのみ拒まれる)からなる群より選択される。
膜分離は、少なくともプロパンおよび水素(H2)を含む気体流を、水素選択性である膜の供給側を通して通過させることを含む。膜透過の駆動力は、透過側と比較してより高い供給側の圧力によって提供される。例えば、供給側の圧力は、10bar以上、例えば20bar以上、または30bar以上、または40bar以上、または50bar以上などの圧力を含み得、および、透過側の圧力は、例えば5bar以下、または10bar以下、または20bar以下、または30bar以下などの供給側より少なくとも1barより低い圧力を含み得る。膜は、例えば酢酸セルロース、ポリスルホン、ポリイミド、ポリアミド、ゼオライト、またはパラジウムなどの膜科学の技術分野でよく知られている高分子材料、セラミック材料または金属材料から作製され得、および、螺旋巻き膜、中空糸膜、チューブまたはプレートの形態であり得る。
膜分離段階の後、粗気体流に比べて水素が枯渇し、プロパンが富化された残余のストリームが供給側から引き出され得る。
膜分離段階の後、粗気体流に比べて水素に富み、およびプロパンに枯渇した透過流は、透過側から引き出され得る。
工程(G)で得られる乾燥された、H2S、CO2およびH2が枯渇した気体流は、バイオプロパンガス組成物を回収するために分画工程(F)に送られる。
好ましい膜分離プロセスで使用される膜は、水素を選択的に透過させるという点で、水素選択的である。様々な水素透過性膜が当該技術分野において知られており、およびいくつかの膜は、膜科学の技術分野でよく知られている高分子、セラミックまたは金属材料、例えばポリスルホン、ポリイミド、ポリアミド、酢酸セルロース、ゼオライトまたはパラジウムに基づくものである。膜は、任意の適切な形状およびサイズを有し得、例えば、螺旋巻き膜、中空糸膜、チューブ膜またはプレート膜の形態であり得る。プロパンに対する水素の実際の選択性は、膜を形成している材料、および供給側と透過側それぞれの温度および圧力を含むプロセス条件に依存する。
本発明のバイオプロパン組成物は、プロピレン組成物を製造するために、脱水素化工程に付され得る。
用語「バイオ-プロピレン組成物(bio-propylene composition)」は、脱水素化流出物から回収される生成物を意味し、一方、用語「脱水素化流出物(dehydrogenation effluent)」は、脱水素化工程後に直接得られる生成物を意味する。本明細書で使用される場合、用語「脱水素化生成物(dehydrogenation product)」はまた、そのような脱水素化工程の後に直接得られる炭化水素の混合物も意味する。
本発明の実施形態を用いて得られる、または得られ得るバイオ-プロピレン組成物は、従来の石油化学、および高分子工業の原料として特に好適である。したがって、生産プロセスの大幅な改変を必要としないまま、既知の付加価値連鎖にプロピレンが添加され得る。
本発明の方法は、CO、CO2、またはジエン/アルキンの少なくとも1つを除去するために、プロピレンに富んだ脱水素化生成物(バイオ-プロピレン組成物)の少なくとも一部を精製処理に付すことをさらに含み得る。本発明の方法の利点は、CO、CO2、およびジエン/アルキンの低い総計の量、およびその結果の、プロピレンに富んだ脱水素化生成物からのCO、CO2、ジエン/アルキン、またはそれらの組み合わせの除去の低減された負担である。これは、プロピレンに富んだ脱水素化生成物の少なくとも一部が重合処理に付される実施形態において特に有利である。
バイオベースの新鮮なフィード
約40wt.-%の飽和C16脂肪酸、約50wt.-%の不飽和C18脂肪酸を含み、約10wt.-%のグリセロール当量を有する植物および動物オイルの混合物を含むトリグリセリドフィードが、漂白により元素不純物を除去するために、初めに前処理された。この後、前処理された原料流(バイオベースの新鮮なフィード原料)が希釈された。この希釈混合物が、水素化処理流出物を製造するために、以下で特定される条件下、水素化脱酸素(HDO)を通して処理された。この水素化処理された流出物が、バイオ-プロパン組成物およびディーゼル範囲のパラフィン系炭化水素を提供するために、分離および精製された。
バイオ再生可能なオイル/脂肪材料が、従来の漂白プロトコルを用いて漂白された。2000ppmのクエン酸、0.2wt.-%の水、および1wt.-%の漂白土が、予熱されたバイオ再生可能なオイル/脂肪材料に添加され、続いて80℃で20分間混合され、減圧を用いて脱水され、および濾過された。漂白されたバイオ再生可能なオイル/脂肪材料中の不純物濃度が以下の表に示されている。
漂白されたバイオ再生可能なオイル/脂肪材料が、水素化処理されたフィードを生成するために、漂白されたバイオ再生可能なオイル/脂肪材料1w部に対して5w部のバイオベースのパラフィン系炭化水素を混合することにより希釈され、DMDS(ジメチルジスルフィド)を用いて20~100wt.-ppmのS(S元素として算出されて)を含むように調整され、金属硫化物触媒を用いて、285℃の温度、約50barのH2圧、および約0.5~1g/g×h-1の空間速度で、水素化脱酸素された。HDO流出物は、約40℃の温度で、反応器圧力で、ガス流および液体流とに分離され、および、パラフィン系炭化水素を得るために、液体流から水が分離され、捨てられた。
パラフィン系炭化水素が、従来の白金ベースの異性化触媒を用いて、および従来のプロセス条件で、水素化異性化に付された。得られたイソパラフィン系炭化水素材料が、分画に供された。自動車用ディーゼル燃料のEN 590要件を満たすディーゼル範囲の炭化水素材料が、バイオベースの新鮮なフィード材料の約83wt.-%に相当する量で回収された。
プロパンに富んだ気体流が、以下の条件下で、初めにアミン洗浄(工程(D))に付された:
-アミンフロー対ガスフロー、サワーガス1トン当たり5.8t/hのアミン溶液、
-アミン水溶液は、吸収材中のCO2吸収を促進するための400ppmのピペラジンを含む、50wt%のメチルジエチルアミン(MDEA)である、
-4MPaの処理圧力、
-ガス入口温度:約40℃、アミン入口温度:約60℃。
脱水素化試験に使用されたプロパンサンプルは、標準の化石プロパン組成物、参照バイオ-プロパン組成物、および本発明によるバイオ-プロパン組成物を含んでいた。本発明によるバイオ-プロパン組成物は、上述の手順を用いて調製された。参照バイオ-プロパン組成物は、他の同様の手順を用いて調製されたバイオプロパンを代表するものであるが、より低いグリセロール当量をもつバイオ再生可能なオイル/脂肪材料から出発し、HDOステップにおいてデカーブ反応に有利な条件(高温、より低いH2圧を含む)を用いたものであった。
1.N2中50%のH2を用いて、550℃で2時間、触媒システムの還元
2.N2フラッシュ、および、オーブン温度の575℃である反応温度への変更
3.575℃での30分の反応
4.N2フラッシュ、および、オーブンを少なくとも30分間600℃である再生温度に変更
5.600℃で15分間、N2中1.5%のO2を用いて再生
6.N2フラッシュ、および、15分以上のオーブン温度の変更。
・希ガスがマイクロGCで測定された:Varian CP-4900、TCD、チャンネル1(H2、N2、CH4、CO):105℃、キャリヤガス Ar、カラム MS5A、チャンネル2(CO2、C2H4、C2H6):80℃、キャリヤガス He、カラム PPU、チャンネル3(C3およびC4化合物:80℃、キャリヤガス He、カラム Al2O3。
・炭化水素組成が以下のGCで測定された:Shimadzu GC2010 Plus、FID、カラム Rt-Alumina BOND/MAPD、プログラム、キャリヤガス He、プログラム。70℃ 2分-4℃/分-140℃-10℃/分-230℃ 9分。
・硫黄化合物が以下の装置で測定された:Agilent 7890B、FPD、カラムGS Gaspro、キャリヤガス He、プログラム:100℃ 2.5分-15℃/分-220℃ 15分。
Claims (15)
- バイオベースの材料をアップグレードするための方法であって、
(A)バイオベースの新鮮なフィード材料の総計の重量に対して2wt.-%~60wt.-%のグリセロール当量を有するバイオ再生可能なオイルおよび/または脂肪のバイオベースの新鮮なフィード材料を提供する工程、
(B)水素化処理された流出物を得るために、前記バイオベースの新鮮なフィード材料および任意には希釈剤を含む水素化処理フィードを、金属硫化物触媒および水素(H2)の存在下でHDOを含む水素化処理へと付す工程であって、前記水素化処理フィードがS元素として算出されて10~10000wt.-ppmの硫黄含有化合物を含む工程、
(C)H2、バイオプロパン、H2O、H2S、CO2、およびCOを含む気体の水素化処理された材料、ならびにパラフィン系炭化水素を含む液体の水素化処理された材料を提供するように、前記水素化処理された流出物を気-液分離に付す工程、
(D)任意の第2の水素化処理の後に、前記液体の水素化処理された材料を分画に付し、および、少なくともディーゼルおよび/またはケロシン範囲のパラフィン系炭化水素材料を回収する工程、
(E)H2SおよびCO2の枯渇した気体ストリームを得るために、前記気体の水素化処理された材料をH2SおよびCO2を除去するための精製工程に付す工程、
(F)乾燥されたH2SおよびCO2の枯渇した気体ストリームを得るために、前記H2SおよびCO2の枯渇した気体ストリームを、H2回収および乾燥に付す工程、
(G)バイオ-プロパン気体組成物を回収するために、前記乾燥されたH2S、CO2およびH2の枯渇した気体ストリームを分画し、および任意には、液化されたバイオ-プロパン組成物を得るために前記バイオ-プロパン気体組成物を圧縮する工程
を含む方法。 - 前記バイオベースの新鮮なフィード材料が、少なくとも3wt.-%、好ましくは少なくとも4wt.-%、より好ましくは少なくとも5wt.-%、さらにより好ましくは少なくとも6wt.-%、最も好ましくは少なくとも7wt.-%、または少なくとも8wt.-%であるグリセロール当量を有し、および/または
前記バイオベースの新鮮なフィード材料が、55wt.-%以下、好ましくは50wt.-%以下、または45wt.-%以下、または40wt.-%以下、または35wt.-%以下、または30wt.-%以下、または25wt.-%以下、または20wt.-%以下であるグリセロール当量を有し、および/または
前記バイオベースの新鮮なフィード材料が、4wt.-%~50wt.-%、好ましくは6wt.-%~40wt.-%、または7wt.-%wt.-%~30wt.-%であるグリセロール当量を有する請求項1記載の方法。 - 前記水素化処理フィードが、S元素で算出されて、10~1000wt.-ppm、好ましくは10~500wt.-ppm、より好ましくは10~300wt.-ppmの硫黄含有化合物を含む請求項1または2記載の方法。
- 前記工程(D)において、水素異性化を含む第2の水素化処理の後に前記液体の水素化処理された材料を分画に付すこと、および、少なくともディーゼルおよび/またはケロシン範囲のイソ-パラフィン系炭化水素材料を回収することを含む請求項1~3のいずれか1項に記載の方法。
- 工程(A)が、前記バイオベースの新鮮なフィード材料を製造するために、オイルおよび/または脂肪中の汚染物質を減少させるために、再生可能なオイルおよび/または脂肪を前処理する工程(A’)を含む請求項1~4のいずれか1項に記載の方法。
- 前記精製工程(E)が、気体の水素化処理された材料から除去されたH2Sを回収し、および回収されたH2Sを水素化処理フィードへとリサイクルする工程(E’)をさらに含む請求項1~5のいずれか1項に記載の方法。
- 前記バイオ-プロパン気体組成物および/または液化されたバイオ-プロパン組成物が、少なくとも90wt.-%、少なくとも91wt.-%、少なくとも92wt.-%、少なくとも93wt.-%、少なくとも94wt.-%、少なくとも95wt.-%、少なくとも96wt.-%、または少なくとも97wt.-%のプロパン含有量を有する請求項1~6のいずれか1項に記載の方法。
- 脱水素化された流出物を得るために、前記バイオ-プロパン気体組成物および/または前記液化されたバイオ-プロパン流出物の少なくとも一部を、触媒脱水素化を含む変換に付し、続いて、任意の精製の後に、バイオ-プロパン組成物を得るために、前記脱水素化された流出物中の少なくともバイオ-プロパンを回収することを含む請求項1~7のいずれか1項に記載の方法。
- バイオ-プロピレン組成物の少なくともバイオ-プロピレンおよび/またはバイオ-プロピレン組成物のバイオ-プロピレンの少なくとも誘導体、任意には他の(共)モノマーと共に、バイオ-ポリマーを製造するために(共)重合することをさらに含む請求項1~8のいずれか1項に記載の方法。
- 40℃で1200~1500kPaの蒸気圧および15℃で495~520kg/m3の密度を有する液化されたバイオ-プロパン組成物であって、
少なくとも94wt.-%のバイオ-プロパン、
最大で2000wt.-ppmのCO2、
最大で1000wt.-ppmのCO、
S元素として算出されて、最大で15wt.-ppmのS含有化合物、
最大で1500wt.-ppmの不飽和炭化水素、
最大で5.5wt.-%の3つ以上の炭素原子を有する炭化水素(C3+炭化水素)、ここで、(液化されたバイオプロパン組成物に対して)最大1.4wt.-%が、5つ以上の炭素原子を有する炭化水素であり、
および、任意には、最大で1500wt.-ppm、好ましくは最大で1000wt.-ppm、より好ましくは最大で800wt.-ppm、さらにより好ましくは最大で500wt.-ppmであるプロピレン
を含むバイオ-プロパン組成物。 - 請求項1~7のいずれか1つに記載の方法によって製造される、請求項10記載の液化されたバイオ-プロパン組成物。
- バイオベースの材料をアップグレードするための方法であって、
(A)バイオベースの新鮮なフィード材料の総重量に対して2wt.-%~60wt.-%のグリセロール当量を有するバイオ再生可能なオイルおよび/または脂肪のバイオベースの新鮮なフィード材料を提供する工程、
(B)水素化処理された流出物を得るために、バイオベースの新鮮なフィード材料および任意には希釈剤を含む水素化処理フィードを金属硫化物触媒および水素(H2)の存在下でHDOを含む水素化処理へと付す工程であって、前記水素化処理フィードがS元素として算出されて10~10000wt.-ppmの硫黄含有化合物を含む工程、
(C)H2、バイオプロパン、H2O、H2S、CO2、およびCOを含む気体の水素化処理された材料、ならびにパラフィン系炭化水素を含む液体の水素化処理された材料を提供するように、前記水素化処理された流出物を気-液分離に付す工程、
(D)任意の第2の水素化処理の後に、前記液体の水素化処理された材料を分画に付し、および、少なくともディーゼルおよび/またはケロシン範囲のパラフィン系炭化水素材料を回収する工程、
(E)H2SおよびCO2の枯渇した気体ストリームを得るために、前記気体の水素化処理された材料をH2SおよびCO2を除去するための精製工程に付す工程、
(F)乾燥されたH2SおよびCO2の枯渇した気体ストリームを得るために、前記H2SおよびCO2の枯渇した気体ストリームを、H2回収および乾燥に付す工程、
(G)バイオ-プロパン気体組成物を回収するために、前記乾燥されたH2S、CO2およびH2の枯渇した気体ストリームを分画し、および任意には、液化されたバイオ-プロパン組成物を得るために前記バイオ-プロパン気体組成物を圧縮する工程、
(H)バイオ-プロピレンを含む脱水素化流出物を得るために、バイオ-プロパンガス組成物および/または液化されたバイオ-プロパン組成物の少なくとも一部を、触媒的脱水素を含む変換に付す工程、
(I)該脱水素化流出物から、バイオ-プロピレン組成物を回収し、および任意には精製する工程
を含む方法。 - 少なくとも1つのバイオ-プロピレン誘導体を得るために、前記バイオ-プロピレン組成物の少なくとも一部を誘導体化することをさらに含み、好ましくは、前記少なくとも1つのバイオ-プロピレン誘導体が、バイオ(メタ)アクリル酸、バイオアクリロニトリル、バイオアクロレインおよびバイオ-プロピレンオキシドからなる群より選ばれる請求項12記載の方法。
- バイオポリマー組成物を得るために、前記回収されたバイオ-プロピレン組成物の少なくとも一部および/またはその誘導体および、任意にはコモノマーおよび/または添加剤を含む混合物を(共)重合することをさらに含む請求項12または13記載の方法。
- 請求項14記載の方法により得られるバイオポリマー組成物。
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WO2021110524A1 (en) | 2021-06-10 |
US20230020748A1 (en) | 2023-01-19 |
CN114729268A (zh) | 2022-07-08 |
FI20196063A1 (en) | 2020-12-31 |
BR112022006058A2 (pt) | 2022-08-09 |
EP4069803A1 (en) | 2022-10-12 |
CA3155563A1 (en) | 2021-06-10 |
KR20220072865A (ko) | 2022-06-02 |
FI128819B (en) | 2020-12-31 |
CA3155563C (en) | 2024-05-28 |
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