CN102050944A - 生产烯化氧的聚合催化剂和聚(烯化氧)的方法 - Google Patents
生产烯化氧的聚合催化剂和聚(烯化氧)的方法 Download PDFInfo
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- CN102050944A CN102050944A CN2010105415686A CN201010541568A CN102050944A CN 102050944 A CN102050944 A CN 102050944A CN 2010105415686 A CN2010105415686 A CN 2010105415686A CN 201010541568 A CN201010541568 A CN 201010541568A CN 102050944 A CN102050944 A CN 102050944A
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- Prior art keywords
- alkylene oxide
- poly
- acid
- propylene oxide
- compound
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- 229920000233 poly(alkylene oxides) Polymers 0.000 title claims abstract description 19
- 238000000034 method Methods 0.000 title claims description 37
- 230000008569 process Effects 0.000 title claims description 3
- 239000002685 polymerization catalyst Substances 0.000 title abstract 6
- 230000000379 polymerizing effect Effects 0.000 claims abstract description 27
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- 238000006116 polymerization reaction Methods 0.000 claims description 33
- 239000003054 catalyst Substances 0.000 claims description 32
- -1 aluminium alkoxide compound Chemical class 0.000 claims description 29
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- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
- C08G65/06—Cyclic ethers having no atoms other than carbon and hydrogen outside the ring
- C08G65/08—Saturated oxiranes
- C08G65/10—Saturated oxiranes characterised by the catalysts used
- C08G65/12—Saturated oxiranes characterised by the catalysts used containing organo-metallic compounds or metal hydrides
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2642—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds characterised by the catalyst used
- C08G65/2645—Metals or compounds thereof, e.g. salts
- C08G65/2654—Aluminium or boron; Compounds thereof
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- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
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Abstract
生产烯化氧的聚合催化剂和聚(烯化氧)的方法。一种烯化氧的聚合催化剂的生产方法,其包含步骤:将铝氧烷化合物与具有羟基基团的化合物接触;其预聚的聚合催化剂的生产方法,包含步骤:在上述聚合催化剂的存在下预聚合烯化氧;和聚(烯化氧)的生产方法,包含步骤:在上述的聚合催化剂或者预聚的聚合催化剂存在下,聚合烯化氧。
Description
技术领域
本发明涉及一种生产烯化氧的聚合催化剂的方法,和一种生产高分子量的聚(烯化氧)的方法。
背景技术
使用有机铝化合物的烯化氧的聚合方法是已知的。这样的聚合方法的例子是:(1)使用氧化双(二乙基铝)的聚合方法,其公开在Journal of the American Chemical Society/89:1/1967年1月4日,173-174,(2)使用三异丁基铝改性的甲基铝氧烷,或者使用固态甲基铝氧烷的聚合方法,其公开在Macromolecules 2003,36,5470-5481中,和(3)聚合方法,其包含步骤:将烯化氧,镧系元素络合物和有机铝化合物彼此接触,其公开在JP11-12351A,JP11-12352A或者JP11-12353A中。
发明内容
但是,上述聚合方法仅仅生产低分子量聚(烯化氧)。因此这里期望一种能够生产高分子量聚(烯化氧)的聚合方法。
由于上述的情况,本发明的一个目标是提供一种生产烯化氧的聚合催化剂的方法,和一种使用通过这样的方法生产的聚合催化剂来生产高分子量聚(烯化氧)的方法。
本发明是一种生产烯化氧的聚合催化剂的方法,其包含步骤:将铝氧烷(alumoxane)化合物与具有羟基基团的化合物接触。这种方法在下文中称作“催化剂生产方法-1”。
同样,本发明是一种生产聚(烯化氧)的方法,其包含步骤:在通过上述的催化剂生产方法-1所生产的烯化氧的聚合催化剂存在下,聚合烯化氧。这种方法在下文中称作“聚合物生产方法-1”。
此外,本发明是一种生产烯化氧的预聚的聚合催化剂的方法,其包含步骤:
(1)将铝氧烷化合物与具有羟基基团的化合物接触,由此形成烯化氧的聚合催化剂;和
(2)在烯化氧的聚合催化剂存在下,对烯化氧进行预聚合,该进行预聚合的烯化氧的量是0.1-10mol,基于烯化氧的聚合催化剂中所包含的每1mol的铝原子。这种方法在下文中称作“催化剂生产方法-2”。
仍然此外的,本发明是一种生产聚(烯化氧)的方法,其包含步骤:在通过上述催化剂生产方法-2生产的烯化氧的预聚的聚合催化剂存在下,对烯化氧进行聚合。这种方法在下文中称作“聚合物生产方法-2”。
上述的“具有羟基基团的化合物”在下文中称作“具有羟基基团的化合物”。
具体实施方式
本发明的铝氧烷化合物是这样的化合物,其具有铝原子到碳原子和到氧原子的直接连接(direct linkage)。该铝氧烷化合物的例子是下式(1)或者(2)所代表的那些:
{-Al(E1)-O-}b (1)
E2{-Al(E2)-O-}cAlE2 2 (2)
其中E1是烃基基团,并且多个E1彼此是相同的或者不同的;b是2或者更大的整数;E2是烃基基团,并且多个E2彼此是相同的或者不同的;和c是1或者更大的整数。
E1优选是具有1-20个碳原子的烃基基团,和更优选是具有1-20个碳原子的烷基基团。该烷基基团的例子是甲基,乙基,正丙基,异丙基,正丁基,异丁基,正戊基和新戊基。在它们中,优选的是甲基或者异丁基。上述b优选是2-40的整数。
E2优选是具有1-20个碳原子的烃基基团,和更优选是具有1-20个碳原子的烷基基团。该烷基基团的例子是甲基,乙基,正丙基,异丙基,正丁基,异丁基,正戊基和新戊基。在它们中,优选的是甲基或者异丁基。上述c优选是1-40的整数。
生产式(1)或者(2)表示的化合物的方法的例子是:(i)方法,其包含步骤:将水与三烷基铝(例如三甲基铝)在有机溶剂(例如苯和脂肪族烃)中的溶液接触,和(ii)方法,其包含步骤:将含有结晶水的金属盐(例如水合硫酸铜)与三烷基铝(例如三甲基铝)接触,这两种方法都是本领域已知的。
上述的铝氧烷化合物可以是市售品。市售品的例子是由三甲基铝生产的PMAO-S和TMAO-211;由三甲基铝和三异丁基铝的混合物生产的MMAO-3A,MMAO-4和TMAO-341;和由三异丁基铝生产的PBAO,它们全部都是由TOSOH FINECHEM CORPORATION生产的。市售品另外的例子是30%的MAO的甲苯溶液,和10%的MAO的甲苯溶液,二者都是由三甲基铝,由Albemarle Corp.生产的。该铝氧烷化合物优选是甲基铝氧烷。
本发明中具有羟基基团的化合物是在它的分子中具有一个或多个羟基基团的化合物。具有羟基基团的化合物的例子是水,醇类,酚类,羧酸,和糖类。
醇类的例子是单羟基醇例如甲醇,乙醇,正丙醇,异丙醇,正丁醇,异丁醇,仲丁醇,叔丁醇,正戊醇,正己醇,正庚醇和正辛醇;和二羟基醇例如乙二醇和丙二醇。这些醇类可以用卤素原子例如氟原子,氯原子,溴原子和碘原子取代。卤素原子取代的醇的例子是氟甲醇,氯甲醇,溴甲醇,碘甲醇,二氟甲醇,二氯甲醇,二溴甲醇,二碘甲醇,三氟甲醇,三氯甲醇,三溴甲醇,三碘甲醇,2,2,2-三氟乙醇,2,2,2-三氯乙醇,2,2,2-三溴乙醇,2,2,2-三碘乙醇,2,2,3,3,3-五氟丙醇,2,2,3,3,3-五氯丙醇,2,2,3,3,3-五溴丙醇,2,2,3,3,3-五碘丙醇,2,2,2-三氟-1-三氟甲基乙醇,2,2,2-三氯-1-三氯甲基乙醇,2,2,2-三溴-1-三溴甲基乙醇,2,2,2-三碘-1-三碘甲基乙醇,1,1-双(三氟甲基)-2,2,2-三氟乙醇,1,1-双(三氯甲基)-2,2,2-三氯乙醇,1,1-双(三溴甲基)-2,2,2-三溴乙醇,和1,1-双(三碘甲基)-2,2,2-三碘乙醇。
上述酚类的例子是酚和具有取代基的酚。该取代基优选是卤素原子(例如氟原子,氯原子,溴原子和碘原子),烷基,芳烷基,芳基,甲硅烷基,烷氧基,芳烷氧基,芳氧基,或者甲硅烷氧基。全部这些基团可以用卤素原子取代。酚具体的例子是2-甲基苯酚,2-乙基苯酚,2-正丁基苯酚,2-异丁基苯酚,2-叔丁基苯酚,2-正丙基苯酚,2-异丙基苯酚,2-苯基苯酚,2,6-二甲基苯酚,2,6-二乙基苯酚,2,6-二正丁基苯酚,2,6-二异丁基苯酚,2,6-二叔丁基苯酚,2,6-二正丙基苯酚,2,6-二异丙基苯酚,2,6-二苯基苯酚,3,4,5-三氟苯酚,3,4,5-三(三氟甲基)苯酚,3,4,5-三(五氟苯基)苯酚,3,5-二氟-4-五氟苯基苯酚,4,5,6,7,8-五氟-2-萘酚,3,4,5-三氯苯酚,3,4,5-三(三氯甲基)苯酚,3,4,5-三(五氯苯基)苯酚,3,5-二氯-4-五氯苯基苯酚,4,5,6,7,8-五氯-2-萘酚,3,4,5-三溴苯酚,3,4,5-三(三溴甲基)苯酚,3,4,5-三(五溴苯基)苯酚,3,5-二溴-4-五溴苯基苯酚,4,5,6,7,8-五溴-2-萘酚,3,4,5-三碘苯酚,3,4,5-三(三碘甲基)苯酚,3,4,5-三(五碘苯基)苯酚,3,5-二碘-4-五碘苯基苯酚,4,5,6,7,8-五碘-2-萘酚,3,5-二氟-4-硝基苯酚,3,5-二氯-4-硝基苯酚,3,5-二溴-4-硝基苯酚,3,5-二碘-4-硝基苯酚,3,5-二氟-4-氰基苯酚,3,5-二氯-4-氰基苯酚,3,5-二溴-4-氰基苯酚,3,5-二碘-4-氰基苯酚,2,3,5,6-四氯苯酚,2,3,5,6-四溴苯酚,2,3,5,6-四碘苯酚,五氟苯酚,五氯苯酚,五溴苯酚和五碘苯酚。
上述羧酸的例子是饱和脂肪族羧酸例如甲酸,乙酸,丙酸,丁酸,戊酸,己酸,月桂酸和硬脂酸;卤代的和饱和的脂肪族羧酸例如三氟乙酸,三氯乙酸,全氟丙酸,全氟丁酸,全氟戊酸,全氟己酸,全氟月桂酸和全氟硬脂酸;不饱和脂肪族羧酸例如油酸(oleic acid),亚油酸(linoleic acid),亚麻酸(linolenic acid),二十二碳六烯酸(docosahexaenoic acid)和二十碳五烯酸(eicosapentaenoic acid);脂肪族二羧酸例如草酸,丙二酸,丁二酸,富马酸,马来酸,戊二酸和己二酸;芳香族羧酸例如苯甲酸,邻苯二甲酸,间苯二甲酸,对苯二甲酸,水杨酸和肉桂酸;和卤代芳族羧酸例如全氟苯甲酸,全氟邻苯二甲酸,全氟间苯二甲酸,全氟对苯二甲酸和全氟水杨酸。
上述糖类的例子是下面的(1)-(6):
(1)式CnH2mOm表示的糖;
(2)多羟基醇;
(3)上述糖(1)的醛衍生物,酮衍生物或者羧酸衍生物;
(4)上述多羟基醇(2)的醛衍生物,酮衍生物或者羧酸衍生物;
(5)上述的(1),(2),(3)或者(4)的缩醛(acetal)保护的产物;和
(6)上述的(1),(2),(3)或者(4)的缩酮(ketal)保护的产物。
上述糖类具体的例子是醛糖(aldoses)例如甘油醛(glyceraldehyde),赤藓糖(erythrose),苏糖(threose),核糖(ribose),阿糖(arabinose),木糖(xylose),来苏糖(lyxose),阿洛糖(allose),阿卓糖(altrose),葡萄糖(glucose),甘露糖(mannose),古洛糖(gulose),艾杜糖(idose),和半乳糖(galactose);酮糖(ketoses)例如二羟丙酮(dihydroxyacetone),赤藓酮糖(erythrulose),核酮糖(ribulose),木酮糖(xylulose),阿洛酮糖(psicose),果糖(fructose),山梨糖(sorbose),塔格糖(tagatose),景天庚酮糖(sedoheptulose),和马桑糖(coriose);二糖类(disaccharides)例如海藻糖(trehalose),异海藻糖(isotrehalose),曲二糖(kojibiose),槐糖(sophorose),黑曲霉二糖(nigerose),昆布二糖(laminaribiose),麦芽糖(maltose),纤维二糖(cellobiose),异麦芽糖(isomaltose),龙胆二糖(gentiobiose),乳糖(lactose)和蔗糖(sucrose);低聚糖(oligosaccharides)例如低聚果糖(fructo-oligosaccharide),低聚半乳糖(galacto-oligosaccharide)和(低聚)乳果糖(lactosucrose);多糖(polysaccharides)例如淀粉(starch),直链淀粉(amylose),支链淀粉(amylopectin),糖原(glycogen),纤维素(cellulose),果胶(pectin),和葡甘露聚糖(glucomannan);内酯(lactones)例如抗坏血酸(ascorbic acid),葡糖醛酸内酯(glucuronolactone),和葡糖酸内酯(gluconolactone);糖醇(sugar alcohols)例如甘油(glycerin),木糖醇(xylitol)和山梨糖醇(sorbitol);氨基酸例如葡糖胺(glucosamine)和半乳糖胺(galactosamine);糖醛酸(uronic acids)例如葡糖醛酸(glucuronic acid)和半乳糖醛酸(galacturonic acid);和脱氧糖(deoxysugars)例如脱氧核糖(deoxyribose),岩藻糖(fucose)和鼠李糖(rhamnose)。
具有羟基基团的化合物优选是水,醇,酚或者羧酸,更优选是水,酚或者羧酸,和另外优选是水,五氟苯酚或者五氟苯甲酸。
该具有羟基基团的化合物的用量优选是0.05至2mol-OH/mol-Al,和更优选0.1至1mol-OH/mol-Al,根据在所用的具有羟基基团的化合物中包含的羟基基团的mol量(mol-OH)/在所用的铝氧烷化合物中包含的每1mol的铝原子(mol-Al)。
该铝氧烷化合物和该具有羟基基团的化合物彼此通常是在-80到100℃,优选-30到50℃,和更优选0-30℃的温度接触的。
上述接触可以在溶剂中进行。溶剂的例子是芳烃溶剂例如苯,甲苯和二甲苯;脂肪族烃溶剂例如正己烷和正庚烷;和脂环烃溶剂例如环己烷;卤代烃溶剂例如二氯甲烷,二氯乙烷,氯苯和二氯苯;以及其两种或多种的组合。在它们中,优选的是芳烃溶剂,脂肪族烃溶剂或者脂环烃溶剂,和更优选的是甲苯,二甲苯,正己烷,环己烷或者正庚烷。溶剂的用量通常是10-2,000重量份,和优选100-1,000重量份,基于1重量份的铝氧烷化合物。
本发明的烯化氧的例子是氧化乙烯,氧化丙烯,1-氧化丁烯,2-氧化丁烯,氧化异丁烯,1-氧化戊烯,2-氧化戊烯,1-氧化己烯,1-氧化辛烯,1-氧化癸烯,氧化环戊烯,氧化环己烯,氧化苯乙烯,氧化乙烯基环己烷,3-苯基氧化丙烯,3,3,3-三氟氧化丙烯,3-萘基氧化丙烯,3-苯氧基氧化丙烯,3-萘氧基氧化丙烯,一氧化丁二烯(butadiene monoxide),3-乙烯氧基氧化丙烯,3-三甲基甲硅烷氧基氧化丙烯,甲基缩水甘油基碳酸酯(methylglycidyl carbonate),乙基缩水甘油基碳酸酯(ethylglycidyl carbonate),胆甾醇基缩水甘油基碳酸酯(cholesterylglycidyl carbonate),和其两种或多种的组合。在它们中,优选的是氧化乙烯,氧化丙烯,1-氧化丁烯,2-氧化丁烯,氧化异丁烯,1-氧化己烯,1-氧化辛烯,1-氧化癸烯或者氧化环己烯,和更优选的是氧化丙烯。
本发明的聚合物生产方法-1和-2是例如通过溶液或者浆体聚合方法,使用溶剂来进行的,或者通过在作为单体的烯化氧的沸点或者更高的温度进行的气相聚合方法来进行的。那些聚合方法是连续的或者分批的方法。上述溶剂的例子是脂肪族烃例如丁烷,戊烷,己烷,庚烷和辛烷;芳烃例如苯和甲苯;和卤代烃例如二氯甲烷。
烯化氧优选是在-70到150℃,和更优选0-50℃聚合的。它的聚合时间通常适宜的根据下面来确定:(i)烯化氧向聚(烯化氧)的转化率,(ii)聚合温度,和(iii)聚合液体中的单体浓度,并且通常是1分钟-100小时,优选1-80小时,和更优选24-80小时。
在催化剂生产方法-2中,烯化氧的预聚是在催化剂生产方法-1生产的聚合催化剂存在下进行的,由此生产了预聚的聚合催化剂,其用于在聚合物生产方法-2中聚合烯化氧。在先术语“烯化氧的预聚”是相对于在后的术语“聚合烯化氧”使用的。所以,在后的聚合可以称作与“预聚”相对的“主聚合”。在预聚中,烯化氧是以0.1-10mol/通过催化剂生产方法-1所生产的聚合催化剂中所包含的1mol的铝原子的量聚合的,该量远小于主聚合中的量。当使用预聚的聚合催化剂时,提高了聚(烯化氧)的产率;即,使用预聚的聚合催化剂的聚合物生产方法-2在它的聚(烯化氧)产率方面高于聚合物生产方法-1。
通过聚合物生产方法-1或者-2所生产的聚(烯化氧)是高分子量的。它的数均分子量(Mn)优选是100,000或者更高,更优选500,000或者更高,和另外优选是5,000,000或者更高。
聚合物生产方法-1或者-2可以通过聚合烯化氧例如氧化丙烯,1-氧化丁烯,1-氧化己烯,氧化苯乙烯和氧化环己烯,来生产有规立构的、全同立构的(stereoregular isotactic)聚(烯化氧)。立构规整性(stereoregularity)可以通过13C-NMR方法来测量。例如,聚(氧化丙烯)的立构规整性通常是基于它的次甲基碳(methine carbon)的积分值,根据在American Chemical Society所编辑的Macromolecules,Vol.19,No.5,第1337-1343页(1986年9月)中详细公开的方法来测量的。聚(烯化氧)的立构规整性越高,聚(烯化氧)的结晶度越高。该立构规整性是通过全同立构三单元组分数(triad fraction)(mm)来表示的。在本发明中,该全同立构三单元组分数优选是81%或者更高,并且当使用聚(氧化丙烯)例如作为薄膜时,它更优选是90%或者更高,和另外优选是99%或者更高。
本发明的聚(烯化氧)具有这样的高分子量,即,该聚(烯化氧)在它的热分解温度方面是高的。所以,本发明的聚(烯化氧)能够适用于作为耐热薄膜。
实施例
本发明参考下面的实施例来更详细的描述,该实施例不限制本发明。
实施例1
使用50mL的用氮气吹扫的烧瓶,来称重对应于10.0mmol-Al的PMAO-S的量的PMAO-S(铝氧烷化合物)的甲苯溶液,该PMAO-S的甲苯溶液是由TOSOH FINECHEM CORPORATION制造的。将烧瓶中的甲苯溶液用20mL脱水甲苯稀释。将36mg(2.0mmol)的水(具有羟基基团的化合物,其已经事先在室温脱气)在搅拌下加入到该PMAO-S溶液中,然后将该混合物搅拌1小时。减压下除去该烧瓶中的挥发性成分,将所形成的材料真空干燥1小时,由此产生白色粉末(烯化氧的聚合催化剂)。
向100mL的用氮气吹扫的烧瓶中加入49.8mg的上面获得的白色粉末,然后向其中加入51.2mL的脱水甲苯,由此将该白色粉末溶解在甲苯中。将6.0mL的氧化丙烯(烯化氧)加入该甲苯溶液中。将该反应混合物在35℃搅拌72小时。该聚合反应是通过加入3.0mL的浓硫酸来猝灭的。用氢氧化钠水溶液中和该混合物,并且分离成为油层和含水层。使用旋转蒸发器除去油层中的挥发性成分,由此获得0.45g的聚(氧化丙烯)。
上面获得的聚(氧化丙烯)的GPC(凝胶渗透色谱法)测量显示了峰强度比为40.5∶59.5的两个峰。发现前者的峰对应于聚(氧化丙烯)(下文称作“聚合物(i)”),其的数均分子量(Mn)是15,320,000,重均分子量(Mw)是29,100,000(所以,它的分子量分布(Mw/Mn)=29,100,000/15,320,000=1.9),发现在后的峰对应于聚(氧化丙烯)(下文称作“聚合物(ii)”),其的数均分子量(Mn)是1,200,重均分子量(Mw)是2,300(所以,它的分子量分布(Mw/Mn)=2,300/1,200=1.9)。上面获得的聚(氧化丙烯)使用丙酮分离成为上述的聚合物(i)和聚合物(ii)。发现聚合物(i)是全同立构的聚(氧化丙烯),具有99%或者更高的全同立构三单元组,发现聚合物(ii)是无规立构的聚(氧化丙烯),通过13C-NMR方法测量。结果在表1中给出。
上面的数均分子量(Mn)和重均分子量(Mw)(所以,也称作Mw/Mn)是在下面的条件下通过凝胶渗透色谱法(GPC)来测量的,其使用通过使用标准聚苯乙烯所制备的校正曲线:
测量设备:LC-2000PLUS系列由JASCO Corporation制造;
柱:TSK-GELG-6000,G-5000,G-4000和G-3000HXL,由TOSOH Corporation制造,这四个柱是串联连接的;
测量温度:40℃;
溶剂:四氢呋喃;和
样品浓度:70mg/mL。
上面的13C-NMR方法是在下面的条件下进行的:
测量设备:400MHz-NMR,由JEOL Ltd.制造;
测量温度:23℃;
溶剂:氯仿-d;和
样品量:10mg。
实施例2
重复实施例1,例外是将水变为2.0mmol的五氟苯酚,由此获得了0.43g的聚(氧化丙烯)。
上面获得的聚(氧化丙烯)的GPC(凝胶渗透色谱法)测量显示了峰强度比为43.1∶56.9的两个峰。发现前者的峰对应于这样的聚(氧化丙烯),其的Mn是5,890,000,和Mw是50,100,000(所以,它的Mw/Mn=50,100,000/5,890,000=8.5),发现在后的峰对应于这样的聚(氧化丙烯),其的Mn是1,100,和Mw是1,800(所以,它的Mw/Mn=1,800/1,100=1.6)。结果在表1中给出。
实施例3
重复实施例1,例外是将水变为2.0mmol的五氟苯甲酸,由此获得了0.55g的聚(氧化丙烯)。
上面获得的聚(氧化丙烯)的GPC(凝胶渗透色谱法)测量显示了峰强度比为36.5∶63.5的两个峰。发现前者的峰对应于这样的聚(氧化丙烯),其的Mn是10,600,000,和Mw是21,200,000(所以,它的Mw/Mn=21,200,000/10,600,000=2.0),发现在后的峰对应于这样的聚(氧化丙烯),其的Mn是1,300,和Mw是1,800(所以,它的Mw/Mn=1,800/1,300=1.4)。结果在表1中给出。
实施例4
重复实施例1,例外是将加入2.0mmol的水变为加入2.0mmol的水,然后搅拌1小时,然后加入2.0mmol的五氟苯酚,由此获得0.48g的聚(氧化丙烯)。
上面获得的聚(氧化丙烯)的GPC(凝胶渗透色谱法)测量显示了峰强度比为41.4∶58.6的两个峰。发现前者的峰对应于这样的聚(氧化丙烯),其的Mn是12,500,000,和Mw是161,000,000(所以,它的Mw/Mn=161,000,000/12,500,000=12.9),发现在后的峰对应于这样的聚(氧化丙烯),其的Mn是1,200,和Mw是1,700(所以,它的Mw/Mn=1,700/1,200=1.4)。结果在表1中给出。
实施例5
重复实施例1,例外是将PMAO-S变为10.0mmol-Al的由TOSOHFINECHEM CORPORATION制造的MMAO-3A,由此获得0.93g的聚(氧化丙烯)。
上面获得的聚(氧化丙烯)的GPC(凝胶渗透色谱法)测量显示了峰强度比为61.1∶38.9的两个峰。发现前者的峰对应于这样的聚(氧化丙烯),其的Mn是7,990,000,和Mw是17,600,000(所以,它的Mw/Mn=17,600,000/7,990,000=2.2),发现在后的峰对应于这样的聚(氧化丙烯),其的Mn是1,300,和Mw是1,800(所以,它的Mw/Mn=1,800/1,300=1.4)。结果在表1中给出。
实施例6
重复实施例1,例外是(i)将PMAO-S变为10.0mmol-Al的由TOSOH FINECHEM CORPORATION制造的MMAO-3A,和(ii)将2.0mmol水变为4.0mmol水,由此获得0.62g的聚(氧化丙烯)。
上面获得的聚(氧化丙烯)的GPC(凝胶渗透色谱法)测量显示了峰强度比为69.7∶30.3的两个峰。发现前者的峰对应于这样的聚(氧化丙烯),其的Mn是10,000,000,和Mw是24,100,000(所以,它的Mw/Mn=24,100,000/10,000,000=2.4),发现在后的峰对应于这样的聚(氧化丙烯),其的Mn是1,300,和Mw是1,800(所以,它的Mw/Mn=1,800/1,300=1.4)。结果在表1中给出。
实施例7
重复实施例1,例外是(i)将PMAO-S变为10.0mmol-Al的由TOSOH FINECHEM CORPORATION制造的MMAO-3A,和(ii)将2.0mmol水变为5.0mmol水,由此获得0.45g的聚(氧化丙烯)。
上面获得的聚(氧化丙烯)的GPC(凝胶渗透色谱法)测量显示了峰强度比为60.2∶39.8的两个峰。发现前者的峰对应于这样的聚(氧化丙烯),其的Mn是7,310,000,和Mw是18,300,000(所以,它的Mw/Mn=18,300,000/7,310,000=2.5),发现在后的峰对应于这样的聚(氧化丙烯),其的Mn是1,400,和Mw是2,100(所以,它的Mw/Mn=2,100/1,400=1.5)。结果在表1中给出。
实施例8
重复实施例1,例外是(i)将PMAO-S变为10.0mmol-Al的由TOSOH FINECHEM CORPORATION制造的MMAO-3A,和(ii)将2.0mmol水变为10.0mmol水,由此获得0.62g的聚(氧化丙烯)。
上面获得的聚(氧化丙烯)的GPC(凝胶渗透色谱法)测量显示了峰强度比为40.9∶59.1的两个峰。发现前者的峰对应于这样的聚(氧化丙烯),其的Mn是19,700,000,和Mw是39,400,000(所以,它的Mw/Mn=39,400,000/19,700,000=2.0),发现在后的峰对应于这样的聚(氧化丙烯),其的Mn是1,500,和Mw是2,300(所以,它的Mw/Mn=2,300/1,500=1.5)。结果在表1中给出。
实施例9
使用50mL的用氮气吹扫的烧瓶,来称重对应于10.0mmol-Al的PMAO-S的量的PMAO-S(铝氧烷化合物)的甲苯溶液,该PMAO-S的甲苯溶液是由TOSOH FINECHEM CORPORATION制造的。将烧瓶中的甲苯溶液用20mL脱水甲苯稀释。将36mg(2.0mmol)的水(具有羟基基团的化合物,其已经事先在室温脱气)在搅拌下加入到该PMAO-S溶液中,然后将该混合物搅拌1小时。将所形成的混合物冷却到-70℃,向其中加入1.4mL(20.0mmol)的氧化丙烯。将该混合物在室温搅拌4小时,然后减压下除去该烧瓶中的挥发性成分。将所形成的材料用每次20mL的脱水己烷洗涤2次,真空干燥1小时,由此产生白色粉末(烯化氧的预聚的聚合催化剂)。
向100mL的用氮气吹扫的烧瓶中加入177mg的上面获得的白色粉末,然后向其中加入51.2mL的脱水甲苯,由此将该白色粉末溶解在甲苯中。将6.0mL的氧化丙烯(烯化氧)加入该甲苯溶液中。将该反应混合物在35℃搅拌72小时。该聚合反应是通过加入3.0mL的浓硫酸来猝灭的。用氢氧化钠水溶液中和该混合物,并且分离成为油层和含水层。使用旋转蒸发器除去油层中的挥发性成分,由此获得0.59g的聚(氧化丙烯)。
上面获得的聚(氧化丙烯)的GPC(凝胶渗透色谱法)测量显示了峰强度比为67.3∶32.7的两个峰。发现前者的峰对应于这样的聚(氧化丙烯),其的Mn是9,570,000,和Mw是23,000,000(所以,它的Mw/Mn=23,000,000/9,570,000=2.4),发现在后的峰对应于这样的聚(氧化丙烯),其的Mn是1,300,和Mw是1,800(所以,它的Mw/Mn=1,800/1,300=1.4)。结果在表2中给出。
实施例10
重复实施例9,例外是将PMAO-S变为10.0mmol的MMAO-3A,由此获得0.99g的聚(氧化丙烯)。
上面获得的聚(氧化丙烯)的GPC(凝胶渗透色谱法)测量显示了峰强度比为74.2∶25.8的两个峰。发现前者的峰对应于这样的聚(氧化丙烯),其的Mn是5,480,000,和Mw是12,100,000(所以,它的Mw/Mn=12,100,000/5,480,000=2.2),发现在后的峰对应于这样的聚(氧化丙烯),其的Mn是1,600,和Mw是2,100(所以,它的Mw/Mn=2,100/1,200=1.3)。结果在表2中给出。
表2
Claims (10)
1.一种生产烯化氧的聚合催化剂的方法,其包含步骤:将铝氧烷化合物与具有羟基基团的化合物接触。
2.根据权利要求1的方法,其中该具有羟基基团的化合物是水,五氟苯酚或者五氟苯甲酸。
3.一种生产聚(烯化氧)的方法,其包含步骤:在通过权利要求1的方法所生产的烯化氧的聚合催化剂存在下,聚合烯化氧。
4.根据权利要求3的方法,其中该具有羟基基团的化合物是水,五氟苯酚或者五氟苯甲酸。
5.根据权利要求3的方法,其中该烯化氧是氧化丙烯。
6.一种生产烯化氧的预聚的聚合催化剂的方法,其包含步骤:
(1)将铝氧烷化合物与具有羟基基团的化合物接触,由此形成烯化氧的聚合催化剂;和
(2)在烯化氧的聚合催化剂存在下,对烯化氧进行预聚合,该进行预聚合的烯化氧的量是0.1-10mol,基于烯化氧的聚合催化剂中所包含的每1mol的铝原子。
7.根据权利要求6的方法,其中该具有羟基基团的化合物是水,五氟苯酚或者五氟苯甲酸。
8.一种生产聚(烯化氧)的方法,其包含步骤:在通过权利要求6的方法生产的烯化氧的预聚的聚合催化剂存在下,对烯化氧进行聚合。
9.根据权利要求8的方法,其中该具有羟基基团的化合物是水,五氟苯酚或者五氟苯甲酸。
10.根据权利要求8的方法,其中该烯化氧是氧化丙烯。
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NORIKAZU UEYAMA ET AL.: "Behavior of the R2AlOAlR2 Catalyst in the Polymerization of Propylene Oxide", 《MACROMOLECULES》, vol. 7, no. 2, 30 April 1974 (1974-04-30), pages 153 - 160 * |
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