TW201430002A - 製造低硫分散劑聚合物的方法 - Google Patents
製造低硫分散劑聚合物的方法 Download PDFInfo
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- TW201430002A TW201430002A TW102139080A TW102139080A TW201430002A TW 201430002 A TW201430002 A TW 201430002A TW 102139080 A TW102139080 A TW 102139080A TW 102139080 A TW102139080 A TW 102139080A TW 201430002 A TW201430002 A TW 201430002A
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- 150000002084 enol ethers Chemical class 0.000 description 1
- XHFTUXTZBNFJAE-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate;morpholine Chemical compound C1COCCN1.CCOC(=O)C(C)=C XHFTUXTZBNFJAE-UHFFFAOYSA-N 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000009715 pressure infiltration Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 239000010802 sludge Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
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- KVWOTUDBCFBGFJ-UHFFFAOYSA-N tert-butyl 2-methylpropanoate Chemical compound CC(C)C(=O)OC(C)(C)C KVWOTUDBCFBGFJ-UHFFFAOYSA-N 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- SWAXTRYEYUTSAP-UHFFFAOYSA-N tert-butyl ethaneperoxoate Chemical compound CC(=O)OOC(C)(C)C SWAXTRYEYUTSAP-UHFFFAOYSA-N 0.000 description 1
- FQFILJKFZCVHNH-UHFFFAOYSA-N tert-butyl n-[3-[(5-bromo-2-chloropyrimidin-4-yl)amino]propyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCNC1=NC(Cl)=NC=C1Br FQFILJKFZCVHNH-UHFFFAOYSA-N 0.000 description 1
- BWSZXUOMATYHHI-UHFFFAOYSA-N tert-butyl octaneperoxoate Chemical compound CCCCCCCC(=O)OOC(C)(C)C BWSZXUOMATYHHI-UHFFFAOYSA-N 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
Classifications
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- C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
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- C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
- C08F265/04—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of esters
- C08F265/06—Polymerisation of acrylate or methacrylate esters on to polymers thereof
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- C08L51/00—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
- C08L51/003—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers grafted on to macromolecular compounds obtained by reactions only involving unsaturated carbon-to-carbon bonds
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Abstract
本發明關於一種製造於聚合物主鏈以及接枝層中含有分散劑重複單元的經接枝之聚(甲基)丙烯酸烷酯(PAMA)的方法，該聚合物係以低硫含量為特徵，關於以此方法可取得的產物及彼等作為燃料(尤其為中間餾出物和其摻合物)之添加劑的用途。本發明進一步關於包含根據本發明的方法所製得的經接枝之聚(甲基)丙烯酸烷酯的組成物及該組成物作為燃料(尤其為中間餾出物和其摻合物)之添加劑組份及改進燃料油和燃料油組成物(尤其為中間餾出物燃料和其摻合物)之冷流動性質的用途。
Description
本發明關於一種製造於聚合物主鏈以及接枝層中含有分散劑重複單元的經接枝之聚(甲基)丙烯酸烷酯(PAMA)的方法，該聚合物係以低硫含量為特徵，關於以此方法可取得的產物及彼等作為燃料(尤其為中間餾出物和其摻合物)之添加劑的用途。本發明進一步關於包含根據本發明的方法所製得的經接枝之聚(甲基)丙烯酸烷酯的組成物及該組成物作為燃料(尤其為中間餾出物和其摻合物)之添加劑組份及改進燃料油和燃料油組成物(尤其為中間餾出物燃料和其摻合物)之冷流動性質的用途。
那些熟諳此項技術者熟知以柴油(例如，加熱油)、航空燃料、燃料油、煤油等等為代表的中間餾出物燃料在促成固體沉積物形成的不利條件下可以長期地貯存。
在室溫下的貯存期間於空氣的存在下所產生的該等沉積物積聚在與油接觸的濾器、濾網、篩網等等上及最終以操作所生成的麻煩物堵塞開口。
不可溶之沉降物的形成導致例如降低的濾網流速或增加的噴嘴堵塞。
為了避免老化產物和沉降物的形成，在無機油提煉廠中、在燃料輸運站或在燃料摻合機中將特定的添加劑添加至柴油燃料和加熱油中。典型使用的添加劑套組包含抗氧化劑、清潔劑添加劑和隨意的十六烷值改進劑作為主要成分，以及冷流動改進劑和抗結冰添加劑。
驚訝地發現於聚合物主鏈以及接枝側鏈兩者中含有N-分散劑單體的經接枝之聚(甲基)丙烯酸烷酯共聚物可被用於穩定中間餾出物之添加劑套組。
聚合物可分散粒子、老化之組份(像是淤渣和膠)及/或正石蠟晶體。
目前的燃料規格限制硫含量至數ppm。此意謂著以穩定燃料或在其他方面改進燃料性能所添加之添加劑較佳地應該不含有任何硫。
眾所週知的是含有鹼性氮取代基的聚合物可被用作為油溶性表面活性劑(C.B.Biswell等人之"New Polymeric Dispersants for Hydrocarbon Systems",Industrial and Engineering Chemistry 1955,47,8,1598-1601)。
此等N-分散劑聚合物可藉由共聚合含N-單體而製得。
目前的分散劑產品含有約750ppm硫。
美國專利第5,035,719號說明分散劑聚(甲基)丙烯酸烷酯改進中間餾出物貯存穩定性的用途。該專利未主張
所製得的聚合物之硫含量，亦未提出製造該等聚合物的方法。
因此，本發明的目的係尋得製造幾乎不含硫之N-分散劑聚(甲基)丙烯酸烷酯的方法。
本發明方法應包括下列者作為關鍵步驟：．使用低硫含量的聚合油及稀釋油；．從配方移除硫醇鏈轉移劑；及．修改方法條件，以便控制在移除硫醇鏈轉移劑之後的分子量。
依照本發明的第一觀點，其係提供一種製造經接枝之聚(甲基)丙烯酸烷酯共聚物(A)的方法，該共聚物含有包含下列者之聚合物主鏈單體單元：(A1)0重量%至40重量%的一或多種式(I)之乙烯系不飽和酯化合物
其中R為H或CH3，R1代表具有1至5個碳原子的直鏈或支鏈、飽和或不飽和烷基或具有3至5個碳原子的環烷基，
R2和R3獨立代表H或式-COOR'之基團，其中R'為H或具有1至5個碳原子的直鏈或支鏈、飽和或不飽和烷基或具有3至5個碳原子的環烷基，(A2)20重量%至93.5重量%的一或多種式(II)之乙烯系不飽和酯化合物
其中R為H或CH3，R4代表具有6至15個碳原子的直鏈或支鏈、飽和或不飽和烷基，R5和R6獨立代表H或式-COOR"之基團，其中R"為H或具有6至15個碳原子的直鏈或支鏈、飽和或不飽和烷基，(A3)5重量%至60重量%的一或多種式(III)之乙烯系不飽和酯化合物
其中R為H或CH3，R7代表具有16至30個碳原子的直鏈或支鏈、飽和
或不飽和烷基，R8和R9獨立代表H或式-COOR'''之基團，其中R'''為H或具有16至30個碳原子的直鏈或支鏈、飽和或不飽和烷基，及(A4)1重量%至40重量%的至少一種選自由下列者所組成之群組的N-分散劑單體：乙烯基吡啶、N-乙烯基咪唑、N-乙烯基吡咯啶酮(NVP)、甲基丙烯酸嗎啉乙酯、N-乙烯基己內醯胺、甲基丙烯酸N,N-二甲基胺基乙酯(DMAEMA)、甲基丙烯酸第三丁基胺基乙酯、N,N-二甲基胺基丙基甲基丙烯醯胺(DMAPMAm)、二甲基胺基丙基丙烯醯胺和二甲基胺基乙基丙烯醯胺，其中組份(A1)至(A4)加總至100重量%；及(A5)0.5重量%至10重量%的至少一種選自由下列者所組成之群組的N-分散劑單體，其接枝在聚合物主鏈上：乙烯基吡啶、N-乙烯基咪唑、N-乙烯基吡咯啶酮(NVP)、甲基丙烯酸嗎啉乙酯、N-乙烯基己內醯胺、甲基丙烯酸N,N-二甲基胺基乙酯(DMAEMA)、甲基丙烯酸第三丁基胺基乙酯、N,N-二甲基胺基丙基甲基丙烯醯胺(DMAPMAm)、二甲基胺基丙基丙烯醯胺和二甲基胺基乙基丙烯醯胺，其中組份(A1)至(A5)加總至100重量%，該方法包含以下步驟：
(a)將無機油裝入反應容器中；(b)製備如上文所述之單體單元(A1)至(A4)與第一反應引發劑之單體混合物；(c)將以步驟(b)所製得的混合物添加至步驟(a)之無機油中，較佳地經1至5小時期間，更佳地經2至3小時期間；(d)將以步驟(c)所獲得的混合物聚合，較佳地在沒有任何鏈轉移劑的存在下；(e)隨意地分離以步驟(c)所獲得的聚合物；(f)添加如上文所述之單體單元(A5)；(g)添加第二反應引發劑；(h)將以步驟(g)所獲得的混合物聚合；(i)隨意地分離以步驟(h)所獲得的聚合物；及/或(j)將以步驟(h)所獲得的聚合物混合物或以步驟(i)所獲得的經分離之聚合物以無機油稀釋，以達成聚合物在油中的所欲濃度。
在本發明的上下文範圍內，術語〝(甲基)丙烯酸烷酯〞係指丙烯酸烷酯和甲基丙烯酸烷酯種類二者或其混合物。以甲基丙烯酸烷酯較佳。
組份(A1)的非限制性實例包括衍生自飽和醇的丙烯酸酯、甲基丙烯酸酯、反丁烯二酸酯和順丁烯二酸酯，諸
如(甲基)丙烯酸甲酯、(甲基)丙烯酸乙酯、(甲基)丙烯酸正丙酯、(甲基)丙烯酸異丙酯、(甲基)丙烯酸正丁酯、(甲基)丙烯酸第三丁酯和(甲基)丙烯酸戊酯；(甲基)丙烯酸環烷酯，像是(甲基)丙烯酸環戊酯、(甲基)丙烯酸環己酯和(甲基)丙烯酸3-乙烯基環己酯；衍生自不飽和醇的(甲基)丙烯酸酯，像是(甲基)丙烯酸2-丙炔酯、(甲基)丙烯酸烯丙酯和(甲基)丙烯酸乙烯酯；及對應之反丁烯二酸酯和順丁烯二酸酯。
單體(A1)係以組份(A1)、(A2)、(A3)與(A4)之總重量為基準計為0重量%至40重量%的量存在，較佳為1重量%至20重量%。
在本發明進一步的具體實例中，組份(A1)包含一或多種式(I)之乙烯系不飽和酯化合物的單體單元
其中R為H或CH3，較佳為CH3，R1代表具有1至5個碳原子的直鏈或支鏈、飽和或不飽和烷基或具有3至5個碳原子的環烷基，及R2和R3獨立代表H。
組份(A2)的非限制性實例包括衍生自飽和醇的(甲基)丙烯酸酯、反丁烯二酸酯和順丁烯二酸酯，諸如(甲基)丙烯酸己酯、(甲基)丙烯酸2-乙基己酯、(甲基)
丙烯酸庚酯、(甲基)丙烯酸辛酯和(甲基)丙烯酸壬酯、(甲基)丙烯酸2-第三丁基庚酯、(甲基)丙烯酸3-異丙基庚酯、(甲基)丙烯酸2-正丙基庚酯、(甲基)丙烯酸癸酯、(甲基)丙烯酸十一酯、(甲基)丙烯酸5-甲基十一酯、(甲基)丙烯酸十二酯、(甲基)丙烯酸2-甲基十二酯、(甲基)丙烯酸十三酯、(甲基)丙烯酸5-甲基十三酯、(甲基)丙烯酸十四酯和(甲基)丙烯酸十五酯；(甲基)丙烯酸環烷酯，諸如(甲基)丙烯酸莰酯、(甲基)丙烯酸2,4,5-三-第三丁基-3-乙烯基環己酯、(甲基)丙烯酸2,3,4,5-四-第三丁基環己酯；甲基丙烯酸環氧乙酯，諸如甲基丙烯酸10,11-環氧基十六酯；及對應之反丁烯二酸酯和順丁烯二酸酯。
單體(A2)係以組份(A1)、(A2)、(A3)與(A4)之總重量為基準計為20重量%至93.5重量%的量存在，較佳為30重量%至60重量%。
在進一步的具體實例中，單體(A2)為(甲基)丙烯酸C8-15-烷酯(較佳為市售的(甲基)丙烯酸月桂酯)或(甲基)丙烯酸C10-15-烷酯部分。主鏈單體更佳為甲基丙烯酸C8-15-烷酯(較佳為市售的甲基丙烯酸月桂酯)或甲基丙烯酸酯C10-15-烷酯部分。
在本發明進一步的具體實例中，組份(A2)包含一或多種式(II)之乙烯系不飽和酯化合物的單體單元
其中R為H或CH3，較佳為CH3，R4代表具有6至15個碳原子的直鏈或支鏈、飽和或不飽和烷基，及R5和R6獨立代表H。
組份(A3)的非限制性實例包括衍生自飽和醇的(甲基)丙烯酸酯，諸如(甲基)丙烯酸十六酯、(甲基)丙烯酸2-甲基十六酯、(甲基)丙烯酸十七酯、(甲基)丙烯酸5-異丙基十七酯、(甲基)丙烯酸4-第三丁基十八酯、(甲基)丙烯酸5-乙基十八酯、(甲基)丙烯酸3-異丙基十八酯、(甲基)丙烯酸十八酯、(甲基)丙烯酸十九酯、(甲基)丙烯酸二十酯、(甲基)丙烯酸二十二酯、(甲基)丙烯酸十六基二十酯、(甲基)丙烯酸硬脂基二十酯和(甲基)丙烯酸二十基四-三十酯；以及對應之反丁烯二酸酯和順丁烯二酸酯；及衍生自不飽和醇的(甲基)丙烯酸酯，諸如(甲基)丙烯酸十八烯酯。
單體(A3)係以組份(A1)、(A2)、(A3)與(A4)之總重量為基準計為5重量%至60重量%的量存在，較佳為20重量%至50重量%。
在本發明進一步的具體實例中，份(A3)包含一或多種式(III)之乙烯系不飽和酯化合物的單體單元
其中R為H或CH3，較佳為CH3，R7代表具有16至30個碳原子的直鏈或支鏈、飽和或不飽和烷基，R8和R9獨立代表H。
N-分散劑單體(A4)尤其可為至少一種選自由下列者所組成之群組的單體：乙烯基吡啶、N-乙烯基咪唑、N-乙烯基吡咯啶酮(NVP)、甲基丙烯酸嗎啉乙酯、N-乙烯基己內醯胺、甲基丙烯酸N,N-二甲基胺基乙酯(DMAEMA)、甲基丙烯酸第三丁基胺基乙酯、N,N-二甲基胺基丙基甲基丙烯醯胺(DMAPMAm)、二甲基胺基丙基丙烯醯胺、二甲基胺基乙基丙烯醯胺和第三丁基丙烯醯胺或其混合物。
在進一步的具體實例中，N-分散劑單體(A4)係選自由下列者所組成之群組：N-乙烯基吡咯啶酮(NVP)、甲基丙烯酸N,N-二甲基胺基乙酯(DMAEMA)和N,N-二甲基胺基丙基甲基丙烯醯胺(DMAPMAm)；尤其較佳為N-乙烯基吡咯啶酮。
N-分散劑單體(A4)的量通常係以組份(A1)、(A2)、(A3)與(A4)之總重量為基準計從1重量%至40重量%，較佳為從2重量%至30重量%。
接枝在聚合物主鏈上的N-分散劑單體(A5)尤其可為至少一種選自由下列者所組成之群組的單體：乙烯基吡啶、N-乙烯基咪唑、N-乙烯基吡咯啶酮(NVP)、甲基丙烯酸嗎啉乙酯、N-乙烯基己內醯胺、甲基丙烯酸N,N-二甲基胺基乙酯(DMAEMA)、甲基丙烯酸第三丁基胺基乙酯、N,N-二甲基胺基丙基甲基丙烯醯胺(DMAPMAm)、二甲基胺基丙基丙烯醯胺和二甲基胺基乙基丙烯醯胺。
在進一步的具體實例中，N-分散劑單體(A5)係選自由下列者所組成之群組：N-乙烯基吡咯啶酮(NVP)、甲基丙烯酸N,N-二甲基胺基乙酯(DMAEMA)和N,N-二甲基胺基丙基甲基丙烯醯胺(DMAPMAm)；尤其較佳為N-乙烯基吡咯啶酮。
依照本發明，較佳的烷基包括甲基、乙基、丙基、異丙基、1-丁基、2-丁基、2-甲基丙基、第三丁基、戊基、2-甲基丁基、1,1-二甲基丙基、己基、庚基、辛基、1,1,3,3-四甲基丁基、壬基、1-癸基、2-癸基、十一烷基、十二烷基、十五烷基和二十烷基。
較佳的環烷基包括環丙基、環丁基、環戊基、環己基、環庚基和環辛基，其隨意地經支鏈或非支鏈烷基取代。
較佳的烯基包括乙烯基、烯丙基、2-甲基-2-丙烯、2-丁烯基、2-戊烯基、2-癸烯基和2-二十烯基。
根據本發明的聚(甲基)丙烯酸烷酯通常具有從
3000至150000之數量平均分子量Mn，較佳為10000至100000，如以粒徑排阻層析術所測量，其係相對於聚苯乙烯標準物進行校準。
聚(甲基)丙烯酸烷酯聚合物之多分散性Mw/Mn較佳地在從1至8之範圍內，尤其從1.5至5.0。重量平均分子量Mw、數量平均分子量Mn及多分散性Mw/Mn可以使用聚苯乙烯作為標準物的GPC測定。
分子量及多分散性可以已知的方法測定。例如，可使用凝膠滲透層析術(GPC)。同樣有可能使用壓滲測定法來測定分子量，例如蒸氣相滲壓測定法。所述及之方法例如說明於：P.J.Flory,"Principles of Polymer Chemistry" Cornell University Press(1953),Chapter VII,266-316 and "Macromolecules,an Introduction to Polymer Science"，F.A.Bovey和F.H.Winslow,Editors,Academic Press(1979),296-312，及W.W.Yau,J.J.Kirkland和D.D.Bly,"Modern Size Exclusion Liquid Chromatography,John Wiley and Sons,New York,1979。為了測定本案所示之聚合物的分子量，優先選擇使用凝膠滲透層析術。較佳地應比對聚甲基丙烯酸酯或聚苯乙烯標準物進行測量。
聚(甲基)丙烯酸烷酯聚合物之聚合物主鏈的構造對許多應用及性質並不重要。據此，該等聚合物可為無規共聚物、梯度共聚物、嵌段共聚物、星形聚合物、超分支聚合物及/或接枝共聚物。嵌段共聚物和梯度共聚物可以例如藉由在鏈成長期間不連續地改變單體組成物而獲得。根
據本發明，製造無規共聚物作為聚合物主鏈。
聚合物主鏈可以一或多個步驟製得，且有可能使用不同的單體組成物(A1)至(A4)，該等可能不同。這能產生可有利於依照本發明使用的聚合物主鏈之混合物。
為了從步驟1中所獲得的通常包含至少一個主鏈聚合物之組成物製造接枝聚合物，將至少一種單體組成物(A5)接枝在藉由聚合組份(A1)至(A4)之混合物而製得的聚合物主鏈上。
假定接枝形成在聚合物主鏈上的側鏈，使得該接枝的至少一部分與聚合物主鏈共價鍵結。
接枝可以一或多個步驟實現。在此上下文中，尤其有可能改變單體組成物(A5)的組成。例如，可使用具有含氮基團的不同單體。
接枝共聚合反應的效能為常見的知識且詳細說明於例如Ullmann's Encyclopedia of Industrial Chemistry,Sixth Edition和Römpp Chemie-Lexikon on CD version 2.0中，其中提及更多文獻。
尤其適合於製造接枝共聚物之習用的自由基聚合反應詳細說明於K.Matyjaszewski,T.P.Davis,Handbook of Radical Polymerization,Wiley Interscience,Hoboken 2002中。就此目的通常使用聚合引發劑及鏈轉移劑。
聚合反應係在作為溶劑的無機油中進行。如上述方法的步驟(a)中所述，裝入反應容器中的無機油可選自由下列者所組成之群組：API(美國石油協會(American
Petroleum Institute))第II族油、API第III族油及API第IV族油，且以低於50ppm之硫含量為特徵，較佳為低於10ppm。
在較佳的具體實例中，無機油係選自由下列者所組成之群組：Purity 1017(Petro Canada；硫含量低於10ppm)、Nebase 3043(Neste Oil)、Yubase 3(硫含量低於10ppm)和Yubase 4(硫含量低於10ppm)。
硫含量通常可根據ASTM D2622測定(以波長分散型X-射線螢光質譜法用於石油產品中的硫之標準試驗方法(Standard Test Method for Sulfur in Petroleum Products by Wavelength Dispersive X-ray Fluorescence Spectrometry))。
在步驟(b)中，將若存在的單體單元(A1)至(A4)與第一反應引發劑混合。
可用的反應引發劑包括在技術領域中廣為已知的偶氮引發劑，諸如AIBN和1,1-偶氮雙環己烷甲腈，及亦包括過氧化合物，諸如過氧化甲基乙酮、過氧化乙醯基丙酮、
二月桂醯基過氧化物、過-2-乙基己酸第三丁酯、過氧化酮、過辛酸第三丁酯、過氧化甲基異丁酮、過氧化環己酮、二苯甲醯基過氧化物、過氧苯甲酸第三丁酯、過氧異丙基碳酸第三丁酯、2,5-雙(2-乙基己醯基過氧基)-2,5-二甲基己烷、過氧-2-乙基己酸第三丁酯、過氧乙酸第三丁酯、過氧-3,5,5-三甲基己酸第三丁酯、二異丙苯基過氧化物、1,1-雙(第三丁基過氧基)環己烷、1,1-雙(第三丁基過氧基)-3,3,5-三甲基環己烷、異丙苯基過氧化氫、第三丁基過氧化氫、過氧二碳酸雙(4-第三丁基環己基)酯、前述化合物中之二或多者相互的混合物、及前述化合物與未述及但同樣可形成自由基之化合物的混合物。
其他有效類型的引發劑係選自由下列者所組成之群組：2,2-二(第三戊基過氧基)丙烷、過氧乙酸第三丁酯、二異丙苯基過氧化物、過氧異丁酸第三丁酯、過氧-2-乙基己酸第三戊酯、二苯甲醯基過氧化物和1,1-二(第三戊基過氧基)環己烷。
根據本發明，在上述方法之步驟(b)中所使用的第一反應引發劑與在上述方法之步驟(g)中所使用的第二反應引發劑可相同或不同。
該等較佳地選自由下列者所組成之群組：過氧-2-乙基己酸第三丁酯和過乙酸第三丁酯。
在步驟(b)中所使用的第一反應引發劑添加以組份(A1)至(A4)之總量為基準計從0.5重量%至1.5重量%的量，較佳為從0.8重量%至1.2重量%的量。
在步驟(g)中所使用的第二反應引發劑添加以組份(A5)之總量為基準計從5重量%至15重量%的量，較佳為從8重量%至12重量%的量。
以步驟(c)中所述的混合物添加較佳地經1至5小時期間完成，更佳地經2至3小時期間。
以步驟(c)所獲得的混合物之聚合反應及以步驟(d)所述的該聚合反應可在有或沒有鏈轉移劑的存在下進行。
適合的鏈轉移劑特別為不含硫化合物，其本身為已知。該等化合物包括例如(沒有任何應強加限制的意圖)二聚合α-甲基苯乙烯(2,4-二苯基-4甲基-1-戊烯)、脂族及/或環脂族醛之烯醇醚、萜烯、α-萜品烯、萜品醇、1,4-環己二烯、1,4-二氫萘、1,4,5,8-四氫萘、2,5-二氫呋喃、2,5-二甲基呋喃及/或3,6-二氫-2H-吡喃；優先選擇為二聚合α-甲基苯乙烯。
該等鏈轉移劑可於市場上取得。該等亦可以那些熟諳此項技術者已知的方式製得。例如，二聚合α-甲基苯乙烯的製造說明於專利DE 966 375中。脂族及/或環脂族醛之烯醇醚揭示於專利DE 3 030 373中。萜烯的製造解釋於EP 80 405中。發表之說明書JP 78/121 891和JP 78/121 890解釋α-萜品烯、萜品醇、1,4-環己二烯、1,4-二氫萘、1,4,5,8-四氫萘的製造。2,5-二氫呋喃、2,5-二甲基呋喃和3,6-二氫-2H-吡喃的製造解釋於發表之說明書DE 2 502 283中。
在本發明較佳的觀點中，步驟(d)的聚合反應係在沒有任何鏈轉移劑的存在下運作。
聚合物主鏈的聚合反應可在標準的壓力、減壓或升壓下執行。聚合溫度不應超過200℃。然而，其通常係在-20℃至200℃之範圍內，較佳為50℃至150℃，而更佳為80℃至130℃。
以步驟(d)所獲得的聚合物可分離或不以任何額外的分離及/或純化步驟而直接接枝。
以步驟(h)所獲得的聚合物亦可分離或不以任何額外的分離及/或純化步驟而直接接枝。
在本發明較佳的具體實例中，兩步驟方法係以一鍋反應來進行。
本發明的第二觀點係指向如上述方法所製造的經接枝之聚(甲基)丙烯酸烷酯共聚物，其以至多100ppm(0至100ppm)之硫含量為特徵，較佳為至多50ppm(0至50ppm)，而更佳為至多40ppm(0至40ppm)。
本發明的第三觀點係指向如上文定義的經接枝之聚(甲基)丙烯酸烷酯共聚物作為添加劑套組(尤其為用於中間餾出物之添加劑套組)之相容劑的用途。
本發明的第四觀點係指向如上文定義的經接枝之聚(甲基)丙烯酸烷酯共聚物作為添加劑套組中用以穩定中間餾出物之組份的用途。
本發明的第五觀點係指向如上文定義的經接枝之聚(甲基)丙烯酸烷酯共聚物改進中間餾出物之冷流動性質
的用途。
本發明進一步的目的係指向改進燃料油組成物之冷流動性質的方法，其包含以下步驟：將至少一種如上述的經接枝之聚(甲基)丙烯酸烷酯共聚物添加至燃料中，尤其至中間餾出物燃料和其摻合物中，及將所得組成物混合。
添加較佳地在完全高於所使用的燃料之濁點的溫度下完成，較佳為比濁點高至少10℃。
本發明的第六觀點係指向如上文定義的經接枝之聚(甲基)丙烯酸烷酯共聚物降低正石蠟沉降在中間餾出物中的用途，較佳地在柴油燃料和其摻合物中。
已概括說明本發明，但是參考在本文僅以例證為目的，而不意欲為限制的某些特定實施例可獲得進一步的瞭解，除非另有其他的指明。
將以下的物質用於聚合物的合成方法中：
ALFOL® 1214-同系物分布
ALFOL® 1620-同系物分布
所述之聚合物的分子量係以下列方法中之一測定：
(a)由配備有2414 RI型檢測器的Waters Alliance 2695系統所組成之GPC系統。兩個Waters Styragel 5E
管柱以1.0毫升THF/分鐘流速及40℃之溫度使用。校準係以寬的聚(甲基丙烯酸烷酯)執行。
(b)由配備有PSS SECcurity線上脫氣器的Agilent 1100 Series幫浦、Agilent 1100 Series RI(檢測溫度40℃)及UV檢測器(波長239奈米)所組成之GPC系統。使用五個SDV管柱及一個溶劑分離管柱，以1.0毫升/分鐘流速之THF作為溶析劑。校準係以從PSS(Mainz)所獲得的PMMA標準物執行。
將57.5公克無機油#1裝入配備有玻璃攪拌器、冷凝器及熱電偶的四頸玻璃圓底燒瓶中。製備251.5公克酯#1、190.5公克酯#2、77.7公克酯#3、32.8公克N-乙烯基吡咯啶酮(NVP)、0.86公克十二基異丁硫醇(DDM)與2.01公克LUPEROX 26之混合物。將336公克混合物添加至含有無機油#1的圓底燒瓶中。將反應加熱至115℃。將剩餘的混合物經由加料漏斗經90分鐘期間添加至圓底燒瓶中。在整個添加期間將反應混合物的溫度維持在115℃。在完成混合物的添加之後，將反應在115℃再保持30分鐘。接著將反應溫度上升至125℃，且添加23.0公克N-乙烯基吡咯啶酮，接著添加2.3公克LUPEROX 7M50。將反應混合物在125℃再保持120分鐘。最後，添加無機油#1，以達成聚合物在油中的所欲濃度。
Mw：220000公克/莫耳
Mn：81000公克/莫耳
PDI：2.72
氮含量：1.2%
硫含量：750ppm(根據ASTM D2622以XRF所測定)
將374.1公克無機油#2裝入配備有玻璃攪拌器、冷凝器及熱電偶的四頸玻璃圓底燒瓶中。將油加熱至115℃。製備251.5公克酯#1、190.5公克酯#2、77.7公克酯#3、32.8公克N-乙烯基吡咯啶酮與5.76公克LUPEROX 26之混合物。將整個混合物經由加料漏斗經120分鐘期間添加至圓底燒瓶中。將反應混合物的溫度在整個添加期間維持在115℃。在完成混合物的添加之後，將反應在115℃再保持30分鐘。接著將反應溫度上升至125℃，且添加23.0公克N-乙烯基吡咯啶酮，接著添加2.3公克LUPEROX 7M50。將反應混合物在125℃再保持120分鐘。最後，添加無機油#2，以達成聚合物在油中的所欲濃度。
Mw：119000公克/莫耳
Mn：47500公克/莫耳
PDI：2.51
氮含量：1.2%
硫含量：40ppm(根據ASTM D2622以XRF所測定)
Claims (24)
- 一種製造經接枝之聚(甲基)丙烯酸烷酯共聚物(A)之方法，該共聚物含有包含下列者之聚合物主鏈單體單元：(A1)0重量%至40重量%的一或多種式(I)之乙烯系不飽和酯化合物
- 根據申請專利範圍第1項之方法，其中在該組份(A1)之式(I)中，R2和R3各自為氫。
- 根據申請專利範圍第1項之方法，其中在該組份(A2)之式(II)中，R5和R6各自為氫。
- 根據申請專利範圍第1項之方法，其中在該組份(A3)之式(III)中，R8和R9各自為氫。
- 根據申請專利範圍第1項之方法，其中該組份(A4)之N-分散劑單體為N-乙烯基吡咯啶酮(NVP)。
- 根據申請專利範圍第1項之方法，其中接枝在組份(A1)至(A4)之聚合物主鏈上的該組份(A5)之N-分散劑單體為N-乙烯基吡咯啶酮(NVP)。
- 根據申請專利範圍第1項之方法，其中該聚(甲基)丙烯酸烷酯具有從3000至150000之數量平均分子量Mn。
- 根據申請專利範圍第1項之方法，其中在步驟(b)中所使用的該第一反應引發劑與在步驟(g)中所使用的該第二反應引發劑可相同或不同。
- 根據申請專利範圍第1項之方法，其中在步驟(b)中所使用的該第一反應引發劑添加以組份(A1)至 (A4)之總量為基準計從0.5重量%至1.5重量%的量，較佳為從0.8重量%至1.2重量%的量。
- 根據申請專利範圍第1項之方法，其中在步驟(g)中所使用的該第二反應引發劑添加以組份(A5)之總量為基準計從5重量%至15重量%的量，較佳為從8重量%至12重量%的量。
- 一種根據申請專利範圍第1至10項中任一項之方法所製得的經接枝之聚(甲基)丙烯酸烷酯共聚物，其特徵在於硫含量至多50ppm。
- 一種根據申請專利範圍第11項的經接枝之聚(甲基)丙烯酸烷酯共聚物的用途，其係作為添加劑套組的可相容劑，尤其用於中間餾出物之添加劑套組。
- 一種根據申請專利範圍第11項的經接枝之聚(甲基)丙烯酸烷酯共聚物的用途，其係作為添加劑套組中用以穩定中間餾出物的組份。
- 一種根據申請專利範圍第11項的經接枝之聚(甲基)丙烯酸烷酯共聚物的用途，其改進中間餾出物的冷流動性質。
- 一種根據申請專利範圍第11項的經接枝之聚(甲基)丙烯酸烷酯共聚物的用途，其降低正石蠟沉降在中間餾出物中，較佳地在柴油燃料中。
- 根據申請專利範圍第12、13、14或15項之用途，其中該中間餾出物為燃料，其包含：(a)從0重量%至99重量%，較佳為1重量%至20重量 %的至少一種生質燃料油，其係以脂肪酸酯為底質，及(b)從1重量%至100重量%，較佳為80重量%至99重量%的化石來源及/或植物及/或動物來源之中間餾出物，其基本上為烴混合物且不含脂肪酸酯，其中組份(a)及(b)加總至100重量%。
- 根據申請專利範圍第12項之用途，其中該添加劑套組包含一或多種選自由下列者所組成之群組的添加劑：冷流動改進劑、分散劑、導電性改進劑、去乳化劑、消泡劑、潤滑性添加劑、抗氧化劑、十六烷值改進劑、清潔劑、染料、標示劑、腐蝕抑制劑、金屬減活劑、金屬鈍化劑、抗結冰添加劑、H2S-清除劑、殺生物劑、除臭劑及/或其他存在的可相容劑。
- 一種組成物，其包含：(A)10重量%至90重量%的根據申請專利範圍第17項的經接枝之聚(甲基)丙烯酸烷酯共聚物，及(B)10重量%至90重量%的烴溶劑或油或烴溶劑與油的混合物，其中組份(A)及(B)加總至100重量%。
- 一種根據申請專利範圍第18項之組成物的用途，其係作為中間餾出物之添加劑套組的可相容劑。
- 一種根據申請專利範圍第18項之組成物的用途，其係作為添加劑套組中用以穩定中間餾出物的組份。
- 一種根據申請專利範圍第18項之組成物的用 途，其改進中間餾出物的冷流動性質。
- 一種根據申請專利範圍第18項之組成物的用途，其降低正石蠟沉降在中間餾出物中，較佳地在柴油燃料中。
- 根據申請專利範圍第19、20、21或22項之用途，其中該中間餾出物為燃料，其包含：(a)從0重量%至99重量%，較佳為1重量%至20重量%的至少一種生質燃料油，其係以脂肪酸酯為底質，及(b)從1重量%至100重量%，較佳為80重量%至99重量%的化石來源及/或植物及/或動物來源之中間餾出物，其基本上為烴混合物且不含脂肪酸酯，其中組份(a)及(b)加總至100重量%。
- 根據申請專利範圍第19項之用途，其中該添加劑套組包含一或多種選自由下列者所組成之群組的添加劑：冷流動改進劑、分散劑、導電性改進劑、去乳化劑、消泡劑、潤滑性添加劑、抗氧化劑、十六烷值改進劑、清潔劑、染料、標示劑、腐蝕抑制劑、金屬減活劑、金屬鈍化劑、抗結冰添加劑、H2S-清除劑、殺生物劑、除臭劑及/或其他存在的可相容劑。
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| US20200270537A1 (en) * | 2017-09-21 | 2020-08-27 | The Lubrizol Corporation | Polyacrylate antifoam components for use in fuels |
| EP3898730A1 (en) * | 2018-12-20 | 2021-10-27 | Basf Se | Polyacrylate polymer |
| CN110172366B (zh) * | 2019-06-12 | 2021-08-17 | 上海应用技术大学 | 一种三元聚合物生物柴油降凝剂、制备及其应用 |
| WO2024120926A1 (en) * | 2022-12-07 | 2024-06-13 | Evonik Operations Gmbh | Sulfur-free dispersant polymers for industrial applications |
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| US2646424A (en) | 1951-05-25 | 1953-07-21 | Dow Chemical Co | Acrylonitrile compositions and process for making the same |
| JPS5347154B2 (zh) | 1974-01-23 | 1978-12-19 | ||
| JPS53121891A (en) | 1977-04-01 | 1978-10-24 | Mitsubishi Chem Ind Ltd | Preparation of methyl methacrylate polymer |
| JPS53121890A (en) | 1977-04-01 | 1978-10-24 | Mitsubishi Chem Ind Ltd | Preparation of methyl methacrylate polymer |
| US4161392A (en) | 1977-11-01 | 1979-07-17 | Texaco Inc. | Nitrogen containing polymers prepared from methacrylic esters as carburetor detergents and corrosion inhibitors |
| DE3010373A1 (de) | 1980-03-18 | 1981-10-01 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von methacrylsaeuremethylester-homo- oder -copolymerisaten |
| DE3607444A1 (de) | 1986-03-07 | 1987-09-10 | Roehm Gmbh | Additive fuer mineraloele mit stockpunktverbessernder wirkung |
| US5035719A (en) | 1988-12-27 | 1991-07-30 | Texaco Inc. | Middle distillate containing storage stability additive |
| CA2013891C (en) * | 1989-04-18 | 2003-01-14 | Joseph M. Bollinger | Dispersant polymethacrylate viscosity index improvers |
| DE69025602T2 (de) * | 1990-01-05 | 1996-11-14 | The Lubrizol Corp., Wickliffe, Ohio | Universelle kraftübertragungsflüssigkeit |
| JPH07286189A (ja) * | 1994-04-18 | 1995-10-31 | Sanyo Chem Ind Ltd | 潤滑油添加剤及び潤滑油 |
| FR2735494B1 (fr) | 1995-06-13 | 1997-10-10 | Elf Antar France | Additif bifonctionnel de tenue a froid et composition de carburant |
| DE19927561C1 (de) | 1999-06-17 | 2000-12-14 | Clariant Gmbh | Verwendung hydroxylgruppenhaltiger Copolymere zur Herstellung von Brennstoffölen mit verbesserter Schmierwirkung |
| EP1533359A1 (en) * | 2003-11-13 | 2005-05-25 | Infineum International Limited | A method of inhibiting deposit formation in a jet fuel at high temperature |
| US7402186B2 (en) * | 2004-02-09 | 2008-07-22 | The Lubrizol Corporation | Fuel composition containing a medium substantially free of sulphur and process thereof |
| DE102004018093A1 (de) * | 2004-04-08 | 2005-10-27 | Rohmax Additives Gmbh | Polymere mit H-Brücken bildenden Funktionalitäten |
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| DE102006001380A1 (de) | 2006-01-11 | 2007-07-26 | Clariant International Limited | Additive für schwefelarme Mineralöldestillate, umfassend Pfropfcopolymere auf Basis von Ethylen-Vinylacetat-Copolymeren |
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| WO2014067749A1 (en) | 2014-05-08 |
| EP2914639B1 (en) | 2017-12-06 |
| SG11201503464SA (en) | 2015-06-29 |
| JP2015535016A (ja) | 2015-12-07 |
| EP2914639A1 (en) | 2015-09-09 |
| RU2650526C2 (ru) | 2018-04-16 |
| CN104768987B (zh) | 2018-10-16 |
| AR093316A1 (es) | 2015-05-27 |
| RU2015120689A (ru) | 2016-12-27 |
| CN104768987A (zh) | 2015-07-08 |
| US20150274875A1 (en) | 2015-10-01 |
| US9957342B2 (en) | 2018-05-01 |
| BR112015009706A2 (pt) | 2017-07-04 |
| KR102012063B1 (ko) | 2019-08-19 |
| BR112015009706B1 (pt) | 2021-04-13 |
| KR20150082242A (ko) | 2015-07-15 |
| JP6433906B2 (ja) | 2018-12-05 |
| ES2656641T3 (es) | 2018-02-27 |
| CA2890044A1 (en) | 2014-05-08 |
| CA2890044C (en) | 2020-10-06 |
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