CN101120040A - 配混缩聚物的方法 - Google Patents
配混缩聚物的方法 Download PDFInfo
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- CN101120040A CN101120040A CNA2006800051115A CN200680005111A CN101120040A CN 101120040 A CN101120040 A CN 101120040A CN A2006800051115 A CNA2006800051115 A CN A2006800051115A CN 200680005111 A CN200680005111 A CN 200680005111A CN 101120040 A CN101120040 A CN 101120040A
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Abstract
本发明涉及一种在含环氧基的苯乙烯和/或(甲基)丙烯酸类单体、双酚A环氧化物或含环氧基的天然油或脂肪酸酯存在下配混选自聚酰胺、聚酯和聚碳酸酯的缩聚物的方法。本发明的特征在于在小于/等于220℃的温度下和在选自锌化合物、钛化合物和C1-C12烷基三苯基卤化的活化剂存在下进行配混。
Description
本发明涉及一种在含环氧基的苯乙烯和/或(甲基)丙烯酸类单体或含环氧基的天然油或脂肪酸酯存在下配混选自聚酰胺、聚酯和聚碳酸酯的均聚或共聚缩聚物的改进方法。
在含环氧基的苯乙烯和/或(甲基)丙烯酸类单体存在下配混PET的方法例如由US2004/0147678已知。PET的典型加工温度为240-300℃。
然而,许多聚合物必须在较低温度下配混。尤其是生物聚合物如聚羟基链烷酸酯在明显高于200℃的温度下分解。其它生物聚合物在高于200℃的温度下明显分解。熔融体积流速(MVR)升高。对于某些应用如吹塑而言不再能够加工高粘性熔体。
本发明的目的为找到一种不具有由US2004/0147678已知方法的缺点的方法。
令人惊讶的是该目的通过将锌化合物、钛化合物或C1-C12烷基三苯基卤化加入熔体而实现。含环氧基的增容剂通过上述化合物激活且甚至可在低于220℃的温度下抵抗链降解。
原则上该方法适合配混选自聚酰胺、聚酯和聚碳酸酯的缩聚物。
本发明方法尤其适合制备选自聚交酯、聚己内酯、聚羟基链烷酸酯以及由脂族和/或芳族二元羧酸和脂族二醇组成的聚酯的可生物降解的均聚酯或共聚酯。
已知为部分芳族聚酯的所有基于脂族和芳族二元羧酸和脂族二羟基化合物的聚酯也是有用的。应理解的是多种这类聚酯的混合物也适合作为缩聚物。
根据本发明,部分芳族聚酯还应理解为聚酯衍生物如聚醚酯、聚酯酰胺或聚醚酯酰胺。合适的部分芳族聚酯包括线性、未增链的聚酯(WO92/09654)。优选增链和/或支化的部分芳族聚酯。后者由作为参考完全引入的文献WO96/15173-15176,21689-21692,25446,25448和WO98/12242已知。不同的部分芳族聚酯的混合物同样有用。部分芳族聚酯尤其包括诸如Ecoflex(BASF Aktiengesellschaft)和EastarBio(Novamont)的产品。
尤其优选的部分芳族聚酯包括其中包含如下物质作为主要组分的聚酯:
A)由如下物质组成的酸组分:
a1)30-99摩尔%的至少一种脂族二元羧酸或至少一种脂环族二元羧酸或其形成酯的衍生物或其混合物,
a2)1-70摩尔%的至少一种芳族二元羧酸或其形成酯的衍生物或其混合物,和
a3)0-5摩尔%的含磺酸根的化合物,
B)选自至少一种C2-C12链烷二醇和至少一种C5-C10环烷二醇或其混合物的二醇组分,
以及如果需要的话额外的一种或多种选自如下的组分:
C)选自如下的组分:
c1)包含至少一个醚官能团并具有式I的二羟基化合物:
HO-[(CH2)n-O]m-H (I)
其中n为2、3或4且m为2-250的整数,
c2)至少一种式IIa或IIb的羟基羧酸:
其中p为1-1500的整数,r为1-4的整数,G为选自亚苯基、-(CH2)q-、-C(R)H-和-C(R)HCH2的基团,其中q为1-5的整数,R为甲基或乙基,
c3)至少一种氨基-C2-C12链烷醇或至少一种氨基-C5-C10环烷醇或其混合物,
c4)至少一种二氨基-C1-C8链烷烃,
c5)至少一种通式III的2,2’-双唑啉:
其中R1为单键,其中z=2、3或4的(CH2)z-亚烷基或亚苯基,c6)至少一种选自天然氨基酸、可由具有4-6个碳原子的二元羧酸
和具有4-10个碳原子的二胺缩聚得到的聚酰胺、式IVa和IVb
化合物的氨基羧酸:
其中s为1-1500的整数,t为1-4的整数,T为选自如下的基团:亚苯基、其中u为1-12的整数的-(CH2)u-、其中R2为甲基或乙基的-C(R2)H-和-C(R2)HCH2,和具有重复单元V的聚唑啉:
其中R3为氢、C1-C6烷基、C5-C8环烷基、未取代或由C1-C4烷基至多三取代的苯基,或四氢呋喃基,
或c1-c6的混合物,
和
D)选自如下的组分:
d1)至少一种具有至少三个能形成酯的基团的化合物,
d2)至少一种异氰酸酯,
d3)至少一种二乙烯基醚,
或d1)-d3)的混合物。
在优选实施方案中,部分芳族聚酯的酸组分A包含30-70摩尔%,尤其是40-60摩尔%a1,以及30-70摩尔%,尤其是40-60摩尔%a2。
有用的脂族酸和相应的衍生物a1通常为具有2-10个碳原子,优选4-6个碳原子的那些。它们可为线性或支化。可用于本发明上下文中的脂环族二元羧酸通常为具有7-10个碳原子,尤其是具有8个碳原子的那些。然而,原则上还可使用具有较大数目碳原子如具有至多30个碳原子的二元羧酸。
实例包括:马来酸、琥珀酸、戊二酸、2-甲基戊二酸、3-甲基戊二酸、己二酸、庚二酸、壬二酸、癸二酸、富马酸、2,2-二甲基戊二酸、辛二酸、1,3-环戊烷二羧酸、1,4-环己烷二羧酸、1,3-环己烷二羧酸、二甘醇酸、衣康酸、马来酸和2,5-降冰片烷二羧酸。
同样可用的上述脂族或脂环族二元羧酸的形成酯的衍生物尤其为二C1-C6烷基酯如二甲基酯、二乙基酯、二正丙基酯、二异丙基酯、二正丁基酯、二异丁基酯、二叔丁基酯、二正戊基酯、二异戊基酯或二正己基酯。同样可使用二元羧酸的酸酐。
二元羧酸或其形成酯的衍生物可单独使用或以其两种或更多种的混合物使用。
特别优选使用己二酸、癸二酸或其特定的形成酯的衍生物或其混合物。特别优选使用己二酸或其形成酯的衍生物如其烷基酯或其混合物。
合适的芳族二元羧酸a2通常为具有8-12个碳原子,优选具有8个碳原子的那些。实例包括对苯二甲酸、间苯二甲酸、2,6-萘甲酸和1,5-萘甲酸以及其形成酯的衍生物。尤其应提及二C1-C6烷基酯,例如二甲基酯、二乙基酯、二正丙基酯、二异丙基酯、二正丁基酯、二异丁基酯、二叔丁基酯、二正戊基酯、二异戊基酯或二正己基酯。二元羧酸a2的酸酐与形成酯的衍生物一样适合。
然而,原则上还可使用具有较大数目碳原子如至多20个碳原子的芳族二元羧酸a2。
芳族二元羧酸或其形成酯的衍生物a2可单独使用或以其两种或更多种的混合物使用。特别优选使用对苯二甲酸或其形成酯的衍生物如对苯二甲酸二甲酯。
所用的含磺酸根的化合物通常为含磺酸根的二元羧酸或其形成酯的衍生物的碱金属或碱土金属盐,优选5-磺基间苯二甲酸的碱金属盐或其混合物,更优选钠盐。
在一个优选实施方案中,酸组分A包含40-60摩尔%a1,40-60摩尔%a2以及0-2摩尔%a3。在另一优选实施方案中,酸组分A包含40-59.9摩尔%a1,40-59.9摩尔%a2以及0.1-1摩尔%a3,尤其是40-59.8摩尔%a1,40-59.8摩尔%a2以及0.2-0.5摩尔%a3。
通常而言,二醇B选自具有2-12个碳原子,优选4-6个碳原子的支化或线性链烷二醇,或具有5-10个碳原子的环烷二醇。
合适的链烷二醇的实例为乙二醇、1,2-丙二醇、1,3-丙二醇、1,2-丁二醇、1,4-丁二醇、1,5-戊二醇、2,4-二甲基-2-乙基己烷-1,3-二醇、2,2-二甲基-1,3-丙二醇、2-乙基-2-丁基-1,3-丙二醇、2-乙基-2-异丁基-1,3-丙二醇、2,2,4-三甲基-1,6-己二醇,尤其是乙二醇、1,3-丙二醇、1,4-丁二醇和2,2-二甲基-1,3-丙二醇(新戊二醇);环戊二醇、1,4-环己二醇、1,2-环己烷二甲醇、1,3-环己烷二甲醇、1,4-环己烷二甲醇或2,2,4,4-四甲基-1,3-环丁二醇。还可使用不同链烷二醇的混合物。
取决于是否需要过量的酸或OH端基,可使用过量的组分A或组分B。在优选实施方案中,所用组分A和B的摩尔比为0.4∶1-1.5∶1,优选0.6∶1-1.1∶1。
除了组分A和B之外,本发明聚酯混合物所基于的聚酯可包含其它组分。
所用二羟基化合物c1优选为二甘醇、三甘醇、聚乙二醇、聚丙二醇和聚四氢呋喃(聚THF),更优选二甘醇、三甘醇和聚乙二醇,且还可使用其混合物,或例如可通过首先使环氧乙烷,然后使环氧丙烷通过本身已知的方法聚合而获得的具有不同变量n的化合物(参见式I)如包含亚丙基单元(n=3)的聚乙二醇,更优选基于具有不同变量n的聚乙二醇的聚合物,其中的单元主要由环氧乙烷形成。通常在250-8000g/mol,优选600-3000g/mol的范围内选择聚乙二醇的分子量(Mn)。
在一个优选实施方案中,可将例如基于B和c1摩尔量为15-98摩尔%,优选60-99.5摩尔%二醇B,以及0.2-85摩尔%,优选0.5-30摩尔%二羟基化合物c1用于制备部分芳族聚酯。
在优选实施方案中,所用的羟基羧酸c2)为:乙醇酸,D-、L-或D,L-乳酸,6-羟基己酸,其环状衍生物如乙交酯(1,4-二烷-2,5-二酮),D-或L-双丙交酯(3,6-二甲基-1,4-二烷-2,5-二酮),对羟基苯甲酸,或其低聚物和聚3-羟基链烷酸酯如聚羟基丁酸、聚羟基戊酸、聚交酯(例如可以EcoPLA2000D(Cargill)获得),或聚3-羟基丁酸和聚羟基戊酸的混合物(其中后者可以Biopol从Zeneca获得),或聚3-羟基丁酸和聚羟基链烷酸如聚羟基己酸或聚羟基辛酸的其它共聚物;为制备部分芳族聚酯,特别优选其低分子量和环状的衍生物。
羟基羧酸的用量基于A和B的量例如可为0.01-50重量%,优选0.1-40重量%。
所用氨基-C2-C12链烷醇或意欲包括4-氨基甲基环己烷甲醇的氨基-C5-C10环烷醇(组分c3)优选为氨基-C2-C6链烷醇如2-氨基乙醇、3-氨基丙醇、4-氨基丁醇、5-氨基戊醇或6-氨基己醇,或氨基-C5-C6环烷醇如氨基环戊醇和氨基环己醇,或其混合物。
所用的二氨基-C1-C8链烷烃(组分c4)优选为二氨基-C4-C6链烷烃如1,4-二氨基丁烷、1,5-二氨基戊烷或1,6-二氨基己烷(六亚甲基二胺,“HMD”)。
在制备部分芳族聚酯的优选实施方案中,可使用基于B的摩尔量为0.5-99.5摩尔%,优选0.5-50摩尔%c3,以及基于B的摩尔量为0-50摩尔%,优选0-35摩尔%c4。
通式III的2,2’-双唑啉c5通常可经由Angew Chem.Int.Edit.,第11卷(1972),第287-288页的方法获得。特别优选的双唑啉为其中R1为单键,其中z=2、3或4的(CH2)z-亚烷基如亚甲基、乙烷-1,2-二基、丙烷-1,3-二基或丙烷-1,2-二基或亚苯基的那些。特别优选的双唑啉包括2,2’-双(2-唑啉)、双(2-唑啉基)甲烷、1,2-双(2-唑啉基)乙烷、1,3-双(2-唑啉基)丙烷和1,4-双(2-唑啉基)丁烷,尤其是1,4-双(2-唑啉基)苯、1,2-双(2-唑啉基)苯或1,3-双(2-唑啉基)苯。
为制备部分芳族聚酯,在每种情况下基于组分B、c3、c4和c5的总摩尔量,例如可使用70-98摩尔%B,至多30摩尔%c3和0.5-30摩尔%c4以及0.5-30摩尔%c5。在另一优选实施方案中,基于A和B的总重量可使用0.1-5重量%,优选0.2-4重量%的c5。
所用组分c6可为天然产生的氨基羧酸。这些包括缬氨酸、亮氨酸、异亮氨酸、苏氨酸、蛋氨酸、苯基丙氨酸、色氨酸、赖氨酸、丙氨酸、精氨酸、天冬氨酸、半胱氨酸、谷氨酸、甘氨酸、组氨酸、脯氨酸、丝氨酸、酪氨酸、天冬酰胺和谷氨酰胺。
优选的通式IVa和IVb的氨基羧酸为其中s为1-1000的整数,t为1-4,优选1或2的整数,且T选自亚苯基和其中u为1、5或12的-(CH2)u-的那些。
c6还可为通式V的聚唑啉。然而,c6还可为不同氨基羧酸和/或聚唑啉的混合物。
在优选实施方案中,c6的用量基于组分A和B的总量为0.01-50重量%,优选0.1-40重量%。
可任选用于制备部分芳族聚酯的其它组分包括包含至少三个能形成酯的基团的化合物d1。
化合物d1优选包含3-10个能形成酯键的官能团。特别优选的化合物d1在分子中具有3-6个这类官能团,尤其是3-6个羟基和/或羧基。实例包括:
酒石酸、柠檬酸、马来酸;
三羟甲基丙烷、三羟甲基乙烷;
季戊四醇;
聚醚三醇;
甘油;
1,3,5-苯三酸;
偏苯三酸、偏苯三酸酐;
苯均四酸、苯均四酸二酐,和
羟基间苯二甲酸。
化合物d1的用量通常基于组分A为0.01-15摩尔%,优选0.05-10摩尔%,更优选0.1-4摩尔%。
所用组分d2为一种异氰酸酯或不同异氰酸酯的混合物。可使用芳族或脂族二异氰酸酯。然而,还可使用较高官能度的异氰酸酯。
在本发明上下文中,芳族二异氰酸酯d2尤其为甲苯2,4-二异氰酸酯、甲苯2,6-二异氰酸酯、二苯基甲烷2,2’-二异氰酸酯、二苯基甲烷2,4’-二异氰酸酯、二苯基甲烷4,4’-二异氰酸酯、亚萘基1,5-二异氰酸酯或苯二亚甲基二异氰酸酯。
其中,特别优选二苯基甲烷2,2’-二异氰酸酯、二苯基甲烷2,4’-二异氰酸酯和二苯基甲烷4,4’-二异氰酸酯作为组分d2。后一二异氰酸酯通常以混合物使用。
也可使用的三环异氰酸酯d2为三(4-异氰基苯基)甲烷。多环芳族二异氰酸酯例如在制备一环或二环二异氰酸酯的过程中获得。
组分d2还可包含少量,例如基于组分d2的总重量至多5重量%的缩脲二酮基用于封端异氰酸酯基。
在本发明上下文中,脂族二异氰酸酯d2尤其为具有2-20个碳原子,优选3-12个碳原子的线性或支化亚烷基二异氰酸酯或亚环烷基二异氰酸酯,例如六亚甲基1,6-二异氰酸酯、异佛尔酮二异氰酸酯或亚甲基双(4-异氰酸根合环己烷)。特别优选的脂族二异氰酸酯d2为六亚甲基1,6-二异氰酸酯和异佛尔酮二异氰酸酯。
优选的异氰脲酸酯包括源于具有2-20个碳原子,优选3-12个碳原子的亚烷基二异氰酸酯或亚环烷基二异氰酸酯如异佛尔酮二异氰酸酯或亚甲基双(4-异氰酸根合环己烷)的脂族异氰脲酸酯。亚烷基二异氰酸酯可为线性或支化。特别优选基于正六亚甲基二异氰酸酯的异氰脲酸酯,例如正六亚甲基二异氰酸酯的环状三聚体、五聚体或更高的低聚物。
通常而言,组分d2的用量基于A和B的总摩尔量为0.01-5摩尔%,优选0.05-4摩尔%,更优选0.1-4摩尔%。
所用二乙烯基醚d3通常可为任何常规且可市购的二乙烯基醚。优选使用1,4-丁二醇二乙烯基醚、1,6-己二醇二乙烯基醚或1,4-环己烷二甲醇二乙烯基醚或其混合物。
二乙烯基醚的用量基于A和B的总重量优选为0.01-5重量%,尤其是0.2-4重量%。
优选的部分芳族聚酯的实例基于如下组分:
A、B、d1
A、B、d2
A、B、d1、d2
A、B、d3
A、B、c1
A、B、c1、d3
A、B、c3、c4
A、B、c3、c4、c5
A、B、d1、c3、c5
A、B、c3、d3
A、B、c3、d1
A、B、c1、c3、d3
A、B、c2
其中,特别优选基于A、B和d1,或A、B和d2,或A、B、d1和d2的部分芳族聚酯。在另一优选实施方案中,部分芳族聚酯基于A、B、c3、c4和c5或A、B、d1、c3和c5。
所提及的部分芳族聚酯和本发明聚酯混合物通常可生物降解。
在本发明上下文中,当物质或物质混合物在DIN V 54900-2(1998年9月的预备标准)中所定义三个方法中的至少一个中具有至少60%的生物降解度时,则该物质或物质混合物具有“生物降解性”的特征。
通常而言,生物降解性导致聚酯或聚酯混合物在合适和可证实的时间内断裂。降解可以酶催化、水解、氧化和/或通过电磁辐射如UV辐射的作用进行,且通常主要由微生物如细菌、酵母、真菌和藻类的作用引起。生物降解性例如可通过将聚酯和堆肥混合并储存一定时间而量化。例如根据DIN EN 13432或DIN V 54900-2的方法3,使不含CO2的空气在堆肥过程中通过熟化的堆肥并使堆肥经受所定义的温度分布。在该情况下,生物降解性经由试样中释放的CO2的净量(减去无试样情况下堆肥释放的CO2量之后)与试样释放的CO2的最大可能量(由试样中碳含量计算)之比而测定,其中将该比例定义为生物降解性百分数。甚至在堆肥数天之后,可生物降解的聚酯或可生物降解的聚酯混合物通常显示显著的降解迹象如霉菌生长、开裂和穿孔。
测定生物降解性的其它方法例如描述在ASTM D 5338和ASTM D6400中。
部分芳族聚酯的制备本身已知或可通过本身已知的方法进行。
优选的部分芳族聚酯的特征为其分子量(Mn)为1000-100000g/mol,尤其是9000-75000g/mol,优选10000-50000g/mol,且其熔点为60-170℃,优选80-150℃。
所述部分芳族聚酯可以具有任何所需比例的羟基和/或羧基端基。所提及的部分芳族聚酯还可端基改性。例如OH端基可通过与邻苯二甲酸、邻苯二甲酸酐、偏苯三酸、偏苯三酸酐、苯均四酸或苯均四酸酐的反应而酸改性。
合适的缩聚物还优选为选自聚交酯、聚己内酯、聚羟基链烷酸酯和脂族二元羧酸与脂族二醇的聚酯的均聚酯或共聚酯的可生物降解的聚酯混合物。
优选的缩聚物也为聚交酯(PLA)和聚羟基链烷酸酯,在此尤其是聚羟基丁酸酯(PHB)和聚羟基丁酸戊酸共聚酯(PHBV)。尤其包括的产品例如为NatureWorks(购自Cargill Dow的聚交酯)、Biocycle(购自PHB Ind.的聚羟基丁酸酯);Enmat(购自Tianan的聚羟基丁酸戊酸共聚酯)。
优选的增容剂例如为含环氧基的苯乙烯和/或(甲基)丙烯酸类单体。该化合物在分子中通常具有两个或更多个环氧基。尤其合适的是低聚或聚合的环氧化化合物如由Johnson Polymers以牌号JoncrylADR 4367或JoncrylADR 4368出售的二-或更多元羧酸的二-或聚缩水甘油酯,或二-或更多元醇的二-或聚缩水甘油醚,或苯乙烯和(甲基)丙烯酸缩水甘油酯的共聚物,或由Resolution Performance Products例如以Epikote828出售的双酚A的缩水甘油醚。
其它优选的增容剂为分子中包含至少一个碳-碳双键或叁键和至少一个环氧基的化合物。丙烯酸缩水甘油酯和甲基丙烯酸缩水甘油酯尤其适合。
还优选由含环氧基(环氧化的)天然油或脂肪酸酯组成的增容剂。天然油例如应理解为橄榄油、亚麻子油、豆油、棕榈油、花生油、椰子油、海藻油、鱼油或这些化合物的混合物。尤其优选环氧化的豆油(例如购自Hobum,Hamburg的MerginatESBO,或购自Cognis,Dusseldorf的EdenolB 316)或环氧化的亚麻子油(例如购自Hobum,Hamburg的MerginatELO)。
优选本发明方法适合制备例如包含作为组分i的Ecoflex和例如作为组分ii的Biocycle、NatureWorks、Biopol或Enmat的可生物降解的聚酯混合物。这些混合物通常包含5-90重量%,优选10-70重量%,更优选15-60重量%,尤其是20-50重量%的组分i,以及10-95重量%,优选30-90重量%,更优选40-85重量%,最优选50-80重量%的组分ii,其中各重量百分数均基于组分i-ii的总重量且其和为100重量%。
对于膜的生产,泡稳定性具有很大的重要性。现在已发现其中组分i形成连续相且组分ii以分开区域嵌入该相的混合物具有良好的泡稳定性。混合物在每种情况下基于组分i和ii(缩聚物)的总重量具有超过45重量%,优选超过50重量%的组分i,从而使组分i形成连续相。
另外本发明方法通常在0.1-5重量%,优选0.1-2重量%,更优选0.3-1重量%增容剂存在下进行,其中各重量百分数均基于缩聚物的总重量。
对本发明而言,活化剂为锌化合物、钛化合物或C1-C12烷基三苯基卤化。有用的活化剂尤其为硬脂酸锌,原钛酸四C1-C6烷基酯如原钛酸四丁基酯,或乙基三苯基溴化。
活化剂以基于缩聚物为0.1-10重量%,优选0.1-5重量%,更优选0.1-1重量%的浓度使用。
可将本领域熟练技术人员已知但非本发明必需的其它组分加入本发明熔体配混物中,所述其它组分例如为塑料技术中的常规添加剂如稳定剂、中和剂、润滑剂和脱模剂、防粘剂、染料或填料。有用的稳定剂例如包括抗氧化剂如空间位阻酚。这可抵抗缩聚物的其它氧化降解。
本发明的可生物降解聚酯混合物可通过已知方法(EP 792 309和US5,883,199)由各组分制备。
例如可在升高的温度如120-220℃下,在本领域熟练技术人员已知的混合设备如捏合机或挤出机中将所有组分i、ii和增容剂在一个工艺步骤中混合并反应。
借助本发明方法,得到了可毫无困难地(具有稳定的泡)加工产生耐刺穿膜的可生物降解的聚合物混合物。
实施例:
性能测试:
如下测定部分芳族聚酯的分子量Mn:
将15mg部分芳族聚酯溶解在10ml六氟代异丙醇(HFIP)中。在每种情况下借助凝胶渗透色谱法(GPC)分析125μl该溶液。在室温下进行测量。将HFIP+0.05重量%三氟乙酸钾用于洗脱。洗脱速率为0.5ml/min。使用如下柱组合(所有柱由日本的Showa Denko Ltd.制造):ShodexHFIP-800P(直径8mm,长度5cm),ShodexHFIP-803(直径8mm,长度30cm),ShodexHFIP-803(直径8mm,长度30cm)。借助RI检测器(差示折光法)检测部分芳族聚酯。用分子量Mn=505至Mn=2740000的窄范围的聚甲基丙烯酸甲酯标准试样校正。在所述区间之外,洗脱范围由外推法测定。
部分芳族聚酯的熔点用购自Seiko的Exstet DSC 6200R单元由DSC测量法测定:
在氮气气氛下,以20℃/min的加热速率将10-15mg具体试样由-70℃加热至200℃。所报告的试样熔点为所观察到熔融峰的峰值温度。在每种情况下所用参比物为空的试样坩埚。
组分i、ii和增容剂的混合物以及所制备的用于对比的混合物的均匀性通过在每种情况下将这些混合物在190℃下压成厚度为30μm的膜而测定。视觉评价这些膜中未分散组分ii的分数。
原料:
组分i:
i-1:为制备聚酯i-1,将87.3kg对苯二甲酸二甲酯、80.3kg己二酸、117kg 1,4-丁二醇和0.2kg甘油与0.028kg原钛酸四丁基酯(TBOT)混合,且醇组分和酸组分的摩尔比为1.30。将反应混合物加热至温度为180℃并在该温度下反应6小时。随后,使温度升高至240℃并在减压下经3小时将过量二羟基化合物蒸出。随后,在240℃在1小时内缓慢计量加入0.9kg六亚甲基二异氰酸酯。
如此得到的聚酯i-1具有119℃的熔点和23000g/mol的分子量(Mn)。组分ii:
ii-1:PHB/V(3%)(Enmat)
增容剂:
购自Johnson Polymer的JoncrylADR 4368。
ESBO:环氧化的豆油(例如购自Hobum,Hamburg的Merginat
ESBO,或购自Cognis,Dusseldorf的EdenolB 316)。
实施例1-4):
研究60重量%Ecoflex和40重量%PHB/V(3%)Enmat的共混物(混合物):
实验程序:
将聚合物(Ecoflex-Enmat共混物)称重入分析天平上的玻璃容器内。随后,在其中加入增容剂(以及在稳定实验中额外的稳定剂),随后加入活化剂。在对比例中,在无活化剂或仅具有稳定剂情况下进行配混。
仅在紧邻进料程序之前滴加入以液体形式存在的催化剂。将混合物装入圆柱体进料附件的漏斗中并借助圆柱体中的模具将其引入挤出机。使熔体在回路中循环3分钟,然后将其由挤出机排出。
温度:170-171℃,旋转速率:80rpm,停留时间:3分钟,重量:17g(聚合物/增容剂、聚合物/增容剂/活化剂、聚合物/稳定剂、聚合物/增容剂/活化剂/稳定剂的混合物)
MVR测量:170℃/2.16kg
实施例 | 缩聚物[重量%] | 增容剂[重量%] | 活化剂[重量%] | 稳定剂[重量%] | 流动速率MVR[cm3/10min]170℃/2.16kg |
对比例1 | 99(Ecoflex F/Enmat-Blend) | 1(JoncrylADR4368) | -- | -- | 51.4 |
实施例2 | 98.5 | 1 | 0.5硬脂酸锌 | -- | 20.1 |
实施例3 | 97.5 | 1 | 0.5硬脂酸锌 | 1Irganox 1010 | 20.0 |
实施例4 | 98.5 | 1 | 0.5原钛酸四丁基酯 | -- | 29.2 |
实施例5 | 98.5 | 1 | 0.5乙基三苯基溴化 | -- | 18.0 |
实施例6 | 94.5 | 5(Merginat) | 0.5硬脂酸锌 | -- | 39.3 |
实施例7 | 98.5 | 1(Epikote828) | 0.5硬脂酸锌 | -- | 31.0 |
与包含增容剂但不含活化剂的对比例1相比,除增容剂外还包含活化剂的实施例2-7显示了明显较低的流动速率(MVR)。
Claims (10)
1.一种在含环氧基的苯乙烯和/或(甲基)丙烯酸类单体、双酚A环氧化物或含环氧基的天然油或脂肪酸酯存在下配混选自聚酰胺、聚酯和聚碳酸酯的缩聚物的方法,其包括在小于/等于220℃的温度下和在选自锌化合物、钛化合物和C1-C12烷基三苯基卤化的活化剂存在下进行配混。
2.根据权利要求1的方法,其中所述缩聚物为一种或多种选自聚交酯、聚己内酯、聚羟基链烷酸酯以及由脂族和/或芳族二元羧酸和脂族二醇组成的聚酯的可生物降解的均聚酯或共聚酯。
3.根据权利要求1或2的方法,其中所述缩聚物为一种或多种选自聚交酯、聚β-羟基丁酸酯、β-羟基丁酸酯-链烷酸酯共聚物和聚酯的可生物降解的均聚酯或共聚酯,其中所述聚酯具有如下组成:
A)由如下物质组成的酸组分:
a1)30-99摩尔%的至少一种脂族二元羧酸或至少一种脂环族二元羧酸或其形成酯的衍生物或其混合物,
a2)1-70摩尔%的至少一种芳族二元羧酸或其形成酯的衍生物或其混合物,和
a3)0-5摩尔%的含磺酸根的化合物,
其中组分a1)-a3)的摩尔百分数之和为100%,和
B)由至少一种C2-C12链烷二醇或C5-C10环烷二醇或其混合物组成的二醇组分,
以及如果需要的话额外的一种或多种选自如下的组分:
C)选自如下的组分:
c1)包含至少一个醚官能团并具有式I的二羟基化合物:
HO-[(CH2)n-O]m-H (I)
其中n为2、3或4且m为2-250的整数,
c2)至少一种式IIa或IIb的羟基羧酸:
HOC(OG-OpH
(IIa) (IIb)
其中p为1-1500的整数,r为1-4的整数,G为选自亚苯基、-(CH2)q-、-C(R)H-和-C(R)HCH2的基团,其中q为1-5的整数,R为甲基或乙基,
c3)至少一种氨基-C2-C12链烷醇或至少一种氨基-C5-C10环烷醇或其混合物,
c4)至少一种二氨基-C1-C8链烷烃,
c5)至少一种通式III的2,2’-双唑啉:
其中R1为单键,其中z=2、3或4的(CH2)z-亚烷基或亚苯基,c6)至少一种选自天然氨基酸、可由具有4-6个碳原子的二元羧酸和
具有4-10个碳原子的二胺缩聚得到的聚酰胺、式IVa和IVb化合物的氨基羧酸:
(IVa) (IVb)
其中s为1-1500的整数,t为1-4的整数,T为选自如下的基团:
亚苯基、其中u为1-12的整数的-(CH2)u-、其中R2为甲基或乙基的-C(R2)H-和-C(R2)HCH2,
和具有重复单元V的聚唑啉:
其中R3为氢,C1-C6烷基,C5-C8环烷基,未取代或由C1-C4烷基至多三取代的苯基,或四氢呋喃基,
或c1-c6的混合物,
和
D)选自如下的组分:
d1)至少一种具有至少三个能形成酯的基团的化合物,
d2)至少一种异氰酸酯,
d3)至少一种二乙烯基醚,
或d1)-d3)的混合物。
4.根据权利要求1-3中任一项的方法,其中含环氧基的苯乙烯和/或(甲基)丙烯酸类单体为丙烯酸缩水甘油酯和/或甲基丙烯酸缩水甘油酯。
5.根据权利要求1-3中任一项的方法,其中含环氧基的天然油为环氧化的橄榄油、亚麻子油、豆油、棕榈油、花生油、椰子油、海藻油、鱼油或这些化合物的混合物。
6.根据权利要求1-5中任一项的方法,其中含环氧基的苯乙烯和/或(甲基)丙烯酸类单体或含环氧基的天然油或脂肪酸酯以基于所述缩聚物为0.1-2重量%的浓度使用。
7.根据权利要求1-6中任一项的方法,其中所述活化剂以基于所述缩聚物为0.3-5重量%的浓度使用。
8.根据权利要求1-6中任一项的方法,其中所用活化剂为原钛酸四C1-C6烷基酯。
9.根据权利要求1-6中任一项的方法,其中所用活化剂为硬脂酸锌。
10.根据权利要求1-6中任一项的方法,其中所用活化剂为乙基三苯基溴化。
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JP4311916B2 (ja) * | 2002-06-05 | 2009-08-12 | アキレス株式会社 | 耐加水分解性に優れた生分解性樹脂製フィルムまたはシート |
JP4423947B2 (ja) * | 2002-11-29 | 2010-03-03 | 東レ株式会社 | 樹脂組成物 |
US7150321B2 (en) * | 2002-12-10 | 2006-12-19 | Halliburton Energy Services, Inc. | Zeolite-containing settable spotting fluids |
US20040147678A1 (en) | 2003-01-29 | 2004-07-29 | Clariant International, Ltd. | Solid concentrate composition for polymeric chain extension |
JP2004323554A (ja) * | 2003-04-21 | 2004-11-18 | Toyobo Co Ltd | 押出発泡成形加工用ポリエステル樹脂組成物、その成形品およびその製造方法 |
WO2004101642A1 (en) * | 2003-05-13 | 2004-11-25 | E.I. Dupont De Nemours And Company | Toughened polyoxymethylene-poly(lactic acid) compositions |
AU2005258271B2 (en) * | 2004-06-23 | 2010-02-18 | Natureworks Llc | Branched polylactic acid polymers and method of preparing same |
JP4720142B2 (ja) * | 2004-10-20 | 2011-07-13 | 東レ株式会社 | 樹脂組成物およびそれからなる成形品 |
JP4645809B2 (ja) * | 2004-12-24 | 2011-03-09 | 東亞合成株式会社 | 熱可塑性樹脂組成物 |
-
2005
- 2005-02-17 DE DE102005007479A patent/DE102005007479A1/de not_active Withdrawn
-
2006
- 2006-02-15 WO PCT/EP2006/050966 patent/WO2006087346A1/de active Application Filing
- 2006-02-15 EP EP06708292.5A patent/EP1853648B1/de not_active Not-in-force
- 2006-02-15 JP JP2007555604A patent/JP5334419B2/ja not_active Expired - Fee Related
- 2006-02-15 US US11/815,582 patent/US20080312379A1/en not_active Abandoned
- 2006-02-15 CN CN2006800051115A patent/CN101120040B/zh not_active Expired - Fee Related
-
2007
- 2007-09-14 KR KR1020077021076A patent/KR101342237B1/ko not_active IP Right Cessation
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
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CN102112519A (zh) * | 2008-06-25 | 2011-06-29 | 梅塔玻利克斯公司 | 支链pha组成物,其制备方法及应用方面的用途 |
CN102112519B (zh) * | 2008-06-25 | 2014-08-13 | 梅塔玻利克斯公司 | 支链pha组成物,其制备方法及应用方面的用途 |
US10030135B2 (en) | 2012-08-17 | 2018-07-24 | Cj Cheiljedang Corporation | Biobased rubber modifiers for polymer blends |
US10669417B2 (en) | 2013-05-30 | 2020-06-02 | Cj Cheiljedang Corporation | Recyclate blends |
US10611903B2 (en) | 2014-03-27 | 2020-04-07 | Cj Cheiljedang Corporation | Highly filled polymer systems |
Also Published As
Publication number | Publication date |
---|---|
US20080312379A1 (en) | 2008-12-18 |
DE102005007479A1 (de) | 2006-08-31 |
JP5334419B2 (ja) | 2013-11-06 |
WO2006087346A1 (de) | 2006-08-24 |
CN101120040B (zh) | 2011-07-06 |
EP1853648B1 (de) | 2016-08-10 |
EP1853648A1 (de) | 2007-11-14 |
KR20070112185A (ko) | 2007-11-22 |
JP2008530328A (ja) | 2008-08-07 |
KR101342237B1 (ko) | 2013-12-20 |
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