CN101970530A - 生物基聚对苯二甲酸乙二醇酯聚合物及制备其的方法 - Google Patents
生物基聚对苯二甲酸乙二醇酯聚合物及制备其的方法 Download PDFInfo
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- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 claims abstract description 39
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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Abstract
一种生物基聚对苯二甲酸乙二醇酯聚合物,其包括约25到约75重量百分比的对苯二甲酸酯组分和约20到约50重量百分比的二醇组分,其中至少约1重量百分比的对苯二甲酸酯和/或二醇组分中的至少一种源自至少一种生物基材料。一种生产生物基聚对苯二甲酸乙二醇酯聚合物的方法,所述方法包括获得包括乙二醇的二醇组分;获得包括对苯二甲酸的对苯二甲酸酯组分,其中二醇组分和/或二醇组分中的至少一种源自至少一种生物基材料;以及使二醇组分和对苯二甲酸酯组分反应以形成生物基聚对苯二甲酸乙二醇酯聚合物,所述生物基聚对苯二甲酸乙二醇酯聚合物包括约25到约75重量百分比的对苯二甲酸酯组分和约20到约50重量百分比的二醇组分。
Description
相关申请资料
本申请根据35U.S.C.§119(e)要求标题为“Bio-based PolyethyleneTerephthalate and Articles Made from Bio-based Polyethylene Terephthalate(生物基聚对苯二甲酸乙二醇酯和由生物基聚对苯二甲酸乙二醇酯制成的制品)”且在2008年3月28号提交的美国临时申请号61/040349的优先权。
发明领域
本发明通常涉及生物基聚对苯二甲酸乙二醇酯聚合物,其包含部分地或全部地源自生物基材料的对苯二甲酸酯和/或二醇组分。
背景
聚对苯二甲酸乙二醇酯及其共聚多酯(下文共同地称为“PET”或“聚对苯二甲酸乙二醇酯”)是用于制备包装制品的广泛使用的原材料,这部分地因为它们的透明度、机械性质和阻气性质的优良组合。PET产品的实例包括但不限于用于包装食品、软饮料、酒精饮料、洗涤剂、化妆品、药品和食用油的瓶子和容器。
大多数商业方法用石油化学衍生的原材料来生产PET。因此,生产成本与石油价格紧密相关。石油化学衍生的PET增加了温室排放物,这是由于其高的石油衍生的碳含量。此外,石油化学产品需要几十万年来自然形成,这使得石油化学衍生的产品是不可再生的,这意味着它们不能够以可与其消费比拟的速率来重新制造、重新生长或再生。
取代石油化学衍生的PET的一种方法是从诸如玉米、水稻或其他产生糖和淀粉的植物的生物基材料生产聚乳酸(PLA)生物塑料。参见例如美国专利第6,569,989号。如在美国专利第5,409,751号和美国专利申请第20070187876号中描述的,已经进行将PLA树脂用于注射拉伸成型工艺(injection stretch molding process)以便生产容器的尝试。然而,在许多应用中,通常难以使得PLA适合于当前的PET生产线或者令人满意地用PLA取代PET,这是由于PLA和PET之间显著不同的性质。例如,PLA通常比PET具有更低的阻气性质,这使得PLA容器较不适用于存储诸如充碳酸气的饮料或对氧气敏感的饮料的物品。此外,当前使用的大多数再循环系统是为PET而设计的,如果引入PLA的话,所述系统会被污染。这一问题可以通过诸如使用在PLA和PET之间有区别的瓶子类型的昂贵的解决方案或通过投资于合适的分选技术或新的再循环流来克服。
因而,存在对具有与石油衍生的PET相似的性质的源自可再生资源的PET的需求。在一些应用中,如果源自可再生资源的PET可以通过现有PET制造设施来加工,和/或可以通过被设计用于再循环石油衍生的PET的系统来容易地再循环,那么这还将是期望的。
从下面的详述、附图和权利要求中,本发明的其他目的、特征和优点将是明显的。
附图简述
图1是制造部分地或全部地源自生物基材料的生物基聚对苯二甲酸乙二醇酯产品的方法的流程图。
本发明的详述
如本申请中所使用的术语“生物基”表示包括源自至少一种生物基材料的一些组分。例如,“生物基PET聚合物”将是包括部分地或全部地源自至少一种生物基材料的至少一种组分的PET聚合物。
生物基PET聚合物
本发明的一个实施方案包括生物基PET聚合物,其包括约25到约75重量百分比的对苯二甲酸酯组分和约20到约50重量百分比的二醇组分,其中至少约1重量百分比的对苯二甲酸酯组分和/或二醇组分中的至少一种源自至少一种生物基材料。在一个更特定的实施方案中,至少约20重量百分比的对苯二甲酸酯组分和/或二醇组分中的至少一种源自至少一种生物基材料。
在一个实施方案中,生物基PET聚合物包括约30到约70重量百分比的对苯二甲酸酯组分。在一个更特定的实施方案中,生物基PET聚合物包括约40到约65重量百分比的对苯二甲酸酯组分。在另一个实施方案中,生物基PET聚合物包括约25到约45重量百分比的二醇组分。在一个更特定的实施方案中,生物基PET聚合物包括约25到约35重量百分比的二醇组分。
根据本发明的一个特定实施方案,对苯二甲酸酯组分选自对苯二甲酸、对苯二甲酸二甲酯、间苯二甲酸及其组合。在一个更特定的实施方案中,至少约10重量百分比的对苯二甲酸酯组分源自至少一种生物基材料。在一个实施方案中,对苯二甲酸酯组分包括至少约70重量百分比的对苯二甲酸。在一个更特定的实施方案中,至少约1重量百分比、优选至少约10重量百分比的对苯二甲酸由至少一种生物基材料制成。
在另一个实施方案中,二醇组分选自乙二醇、环己烷二甲醇及其组合。在一个更特定的实施方案中,二醇组分包括至少约1重量百分比的环己烷二甲醇。在另一个实施方案中,至少约10重量百分比的二醇组分源自至少一种生物基材料。
可以将其他成分加入到生物基PET聚合物中。本领域的普通技术人员将能够容易地选择合适的成分来加入到生物基PET聚合物中,以便改进所期望的性质,这可以取决于所预期的应用类型。在一个特定的实施方案中,生物基PET聚合物还可以包括补充组分,补充组分选自至少一种着色剂、至少一种快速再热添加剂、至少一种阻气添加剂、至少一种UV阻挡添加剂及其组合。
生物基PET聚合物可以用于形成生物基树脂,使用包括但不限于注射成型和拉伸吹塑的方法,生物基树脂可以进一步被加工成生物基容器。本发明的实施方案包括生物基容器,该生物基容器包括上述实施方案的生物基PET聚合物。为适用于某些应用,容器具有某种特性粘度以抵抗移动、倾斜和其他要求。在本发明的一个更特定的实施方案中,生物基容器具有约0.45dL/g到约1.0dL/g的特性粘度。
本领域中已知具有约5,700年的半衰期的碳-14(C-14)存在于生物基材料中但不存在于化石燃料中。因而,“生物基材料”是指其中碳来自非化石生物源的有机材料。生物基材料的例子包括但不限于糖、淀粉、玉米、自然纤维、甘蔗、甜菜、柑橘类果实、木本植物、纤维素、木质纤维(lignocelluosic)、半纤维素、马铃薯、植物油、其他多聚糖及其组合,其他多聚糖诸如果胶、甲壳质、果聚糖和支链淀粉。根据一个特定的实施方案,至少一种生物基材料选自玉米、甘蔗、甜菜、马铃薯、淀粉、柑橘类果实、木本植物、纤维素木质素、植物油、天然纤维、油质木材原料及其组合。
如先前所解释的,C-14的检测指示生物基材料。C-14水平可以通过经由液体闪烁计数来测量其衰变过程(衰变每分钟每克碳或dpm/gC)来确定。在本发明的一个实施方案中,生物基PET聚合物包括至少约0.1dpm/gC(衰变每分钟每克碳)的C-14。
通过以下实施例进一步阐释本发明,实施例不以任何方式被解释成对本发明的范围强加限制。相反,应清楚理解,可以采取本领域的技术人员在阅读本文的描述之后可以看出的各种其他实施方案、修改及其等效物而不偏离本发明的精神和/或所附权利要求的范围。
实施例I
以盲试验方式测量以下样品,以通过液体闪烁计数确定C-14含量的存在。所检测的水平被归一化至可在佐治亚大学得到的现有数据,该现有数据使C-14水平与生物基百分比相互关联。结果在表1中示出。
表1
如表1所示的,全部源自石油的样品(样品2、3和4)包含可忽略的量的C-14,表示样品的约零百分比由生物基材料制成。相比之下,包含已知部分地或全部地源自生物基材料(玉米或糖)的材料的样品显示更高水平的C-14。根据数据,约0.14dpm/gC对应于样品中约1百分比的生物基材料。
制备聚对苯二甲酸乙二醇酯聚合物的方法
参考图1,本发明的实施方案还包括一种用于生产生物基PET聚合物16的工艺,所述工艺包括获得包括乙二醇12a的二醇组分12[步骤20];获得包括对苯二甲酸的对苯二甲酸酯组分14[步骤22],其中至少约1重量百分比的二醇组分和/或对苯二甲酸酯组分(12,14)中的一种源自至少一种生物基材料10;使二醇组分12和对苯二甲酸酯组分14反应以形成生物基PET聚合物16[步骤24],其中生物基PET聚合物16包括约25到约75重量百分比的对苯二甲酸酯组分14和约20到约50重量百分比的二醇组分12。在一个更特定的实施方案中,如反应I所阐述的,步骤24还包括使二醇组分12和对苯二甲酸酯组分14通过酯化反应来反应,以形成生物基PET单体16a,生物基PET单体16a随后经历聚合以形成生物基PET聚合物16。
反应I
在一个特定的实施方案中,至少约1重量百分比的二醇组分12源自至少一种生物基材料10。在一个更特定的实施方案中,至少10重量百分比的二醇组分12源自至少一种生物基材料10。在一个还更特定的实施方案中,至少30重量百分比的二醇组分12源自至少一种生物基材料10。
可以使用任何工艺使二醇组分12部分地或全部地源自至少一种生物基材料。在一个实施方案中,步骤20包括从至少一种生物基材料获得糖或其衍生物以及将糖或其衍生物发酵为乙醇。在另一个实施方案中,步骤20包括气化至少一种生物基材料10以生产合成气,合成气被转化为乙醇。在一个更特定的实施方案中,如通过反应II所阐述的,步骤20还包括使乙醇脱水为乙烯,将乙烯氧化为环氧乙烷以及将环氧乙烷转化为乙二醇。
反应II
在另一个实施方案中,步骤20包括从至少一种生物基材料获得糖或其衍生物以及将糖或其衍生物转化为包括乙二醇和除乙二醇之外的至少一种二醇的混合物。步骤20还包括从混合物中分离出乙二醇。使混合物重复地反应以获得更高收率的乙二醇。在一个更特定的实施方案中,至少一种二醇选自丁二醇、丙二醇和甘油。
根据另一个实施方案,至少约1重量百分比的对苯二甲酸酯组分14源自至少一种生物基材料10。在一个更特定的实施方案中,至少10重量百分比的对苯二甲酸酯组分14源自至少一种生物基材料10。在一个还更特定的实施方案中,至少30重量百分比的对苯二甲酸酯组分14源自至少一种生物基材料10。
可以使用任何工艺使对苯二甲酸酯组分14部分地或全部源自至少一种生物基材料。在一个实施方案中,如反应III中所阐述的,步骤22包括从油质木材原料提取蒈烯;通过脱氢和芳构化将蒈烯转化为对伞花烃和间伞花烃;以及将对伞花烃和间伞花烃氧化为对苯二甲酸和间苯二甲酸。
反应III
在另一个实施方案中,如反应IV中所阐述的,步骤22包括从至少一种生物基材料提取苧烯;将苧烯转化为至少一种萜;将萜转化为对伞花烃以及将对伞花烃氧化为对苯二甲酸。在一个更特定的实施方案中,至少一种萜选自萜品烯、二戊烯、萜品油烯及其组合。在一个还更特定的实施方案中,至少一种生物基材料选自柑橘类果实、木本植物或其组合。
反应IV
在本发明的一个实施方案中,如反应V中所描述的,步骤22包括从生物基材料提取羟甲基糠醛;将羟甲基糠醛转化为第一中间体;使第一中间体与乙烯反应以形成第二中间体;在催化剂的存在下用酸处理第二中间体以形成羟甲基苯甲醛;以及将羟甲基苯甲醛氧化为对苯二甲酸。在一个更特定的实施方案中,从选自玉米糖浆、糖、纤维素及其组合的生物基材料提取羟甲基糠醛。在一个还更特定的实施方案中,乙烯源自至少一种生物基材料。
反应V
在另一个实施方案中,步骤22包括气化至少一种生物基材料10以生产合成气;将合成气转化为对二甲苯;以及在酸中氧化对二甲苯以形成对苯二甲酸。
在一个实施方案中,至少约1重量百分比的对苯二甲酸酯组分14源自至少一种生物基材料10,且至少约1重量百分比的二醇组分12源自至少一种生物基材料10。在一个更特定的实施方案中,至少约25重量百分比的对苯二甲酸酯组分14源自至少一种生物基材料10。在一个还更特定的实施方案中,至少约70重量百分比的二醇组分12源自至少一种生物基材料10。根据一个特定的实施方案,生物基材料选自玉米、甘蔗、甜菜、马铃薯、淀粉、柑橘类果实、木本植物、纤维素木质素、植物油、天然纤维、油质木材原料及其组合。
在另一个实施方案中,所述方法还包括由生物基PET聚合物16制造生物基PET产品18。生物基PET产品18可以用于各种应用,所述应用包括但不限于,作为饮料容器。在另一个实施方案中,生物基PET产品18可以通过被设计用于石油衍生的PET产品的再循环系统来循环或再使用[步骤26]。
应理解,前述内容涉及本发明的特定实施方案,且可以在其中进行许多变化,而不偏离如由下面的权利要求界定的本发明的范围。
Claims (17)
1.一种生物基聚对苯二甲酸乙二醇酯聚合物,所述生物基聚对苯二甲酸乙二醇酯聚合物包括:
约25到约75重量百分比的对苯二甲酸酯组分,其中所述对苯二甲酸酯组分选自对苯二甲酸、对苯二甲酸二甲酯、间苯二甲酸及其组合;以及
约20到约50重量百分比的二醇组分,其中所述二醇组分选自乙二醇、环己烷二甲醇及其组合;
其中至少约1重量百分比的所述对苯二甲酸酯和/或所述二醇组分中的至少一种源自至少一种生物基材料。
2.根据权利要求1所述的生物基聚对苯二甲酸乙二醇酯聚合物,其中至少约10重量百分比的所述二醇组分源自至少一种生物基材料。
3.根据权利要求1-2所述的生物基聚对苯二甲酸乙二醇酯聚合物,其中至少约10重量百分比的所述对苯二甲酸酯组分源自至少一种生物基材料。
4.根据权利要求1-2所述的生物基聚对苯二甲酸乙二醇酯聚合物,其中所述对苯二甲酸酯组分包括至少约70重量百分比的对苯二甲酸,且其中至少约10重量百分比的所述对苯二甲酸源自至少一种生物基材料。
5.根据权利要求1-4所述的生物基聚对苯二甲酸乙二醇酯聚合物,其中所述至少一种生物基材料选自玉米、甘蔗、甜菜、马铃薯、淀粉、柑橘类果实、木本植物、纤维素木质素、植物油、天然纤维、油质木材原料及其组合。
6.根据权利要求1-5所述的生物基聚对苯二甲酸乙二醇酯聚合物,所述生物基聚对苯二甲酸乙二醇酯聚合物还包括补充组分,所述补充组分选自至少一种着色剂、至少一种耐快速再热添加剂、至少一种阻气添加剂、至少一种UV阻挡添加剂及其组合。
7.一种生物基容器,所述生物基容器包含权利要求1-6的生物基聚对苯二甲酸乙二醇酯聚合物。
8.根据权利要求7所述的生物基容器,其中所述生物基聚对苯二甲酸乙二醇酯聚合物包括至少约0.1dpm/gC的碳-14。
9.一种生物基容器,所述生物基容器包含生物基聚对苯二甲酸乙二醇酯聚合物,其中至少1重量百分比的所述聚对苯二甲酸乙二醇酯聚合物源自至少一种生物基材料,其中所述生物基容器具有约0.45dL/g到约1.0dL/g的特性粘度。
10.根据权利要求9所述的生物基容器,其中所述生物基聚对苯二甲酸乙二醇酯聚合物包括约25到约75重量百分比的对苯二甲酸酯组分,其中所述对苯二甲酸酯组分选自对苯二甲酸、对苯二甲酸二甲酯、间苯二甲酸及其组合;以及
约20到约50重量百分比的二醇组分,其中所述二醇组分选自乙二醇、环己烷二甲醇及其组合;
其中至少约10重量百分比的所述二醇组分源自至少一种生物基材料。
11.一种生产生物基聚对苯二甲酸乙二醇酯聚合物的方法,所述方法包括:
a.获得包括乙二醇的二醇组分;
b.获得包括对苯二甲酸的对苯二甲酸酯组分,
其中所述二醇组分和/或所述对苯二甲酸酯组分中的至少一种源自至少一种生物基材料;以及
c.使所述二醇组分和所述对苯二甲酸酯组分反应以形成生物基聚对苯二甲酸乙二醇酯聚合物,其中所述生物基聚对苯二甲酸乙二醇酯聚合物包括约25到约75重量百分比的所述对苯二甲酸酯组分和约20到约50重量百分比的所述二醇组分。
12.根据权利要求11所述的方法,其中所述至少一种生物基材料选自玉米、甘蔗、甜菜、马铃薯、淀粉、柑橘类果实、木本植物、纤维素木质素、油质木材原料及其组合。
13.根据权利要求11-12所述的方法,其中步骤(a)还包括:
i.从至少一种生物基材料获得糖或其衍生物;
ii.将糖或其衍生物发酵为乙醇;
iii.使乙醇脱水为乙烯;
iv.将乙烯氧化为环氧乙烷;以及
v.将环氧乙烷转化为乙二醇。
14.根据权利要求11-12所述的方法,其中步骤(a)还包括:
i.从至少一种生物基材料获得糖或其衍生物;
ii.使糖或衍生物反应以形成包括乙二醇和除乙二醇之外的至少一种二醇的混合物;以及
iii.从所述混合物中分离出乙二醇。
15.根据权利要求11-14所述的方法,其中步骤(b)还包括:
i.从至少一种生物基材料获得蒈烯;
ii.将蒈烯转化为伞花烃;以及
iii.将伞花烃氧化为对苯二甲酸。
16.根据权利要求11-14所述的方法,其中步骤(b)还包括:
i.从至少一种生物基材料获得苧烯;
ii.将所述苧烯转化为至少一种萜;
iii.将所述至少一种萜转化为伞花烃;以及
iv.将伞花烃氧化为对苯二甲酸。
17.一种通过权利要求11-16的方法生产的生物基聚对苯二甲酸乙二醇酯聚合物。
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Cited By (4)
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CN102875783A (zh) * | 2011-07-15 | 2013-01-16 | 东丽纤维研究所(中国)有限公司 | 一种聚酯、其制备方法及其用途 |
CN107922602A (zh) * | 2015-07-01 | 2018-04-17 | 诺沃梅尔公司 | 由生物基乙醇制造的聚合物组合物 |
CN109196020A (zh) * | 2016-05-31 | 2019-01-11 | 三得利控股株式会社 | 生物pet树脂的制造方法 |
CN110402308A (zh) * | 2016-11-09 | 2019-11-01 | 可口可乐公司 | 生物基meg和聚酯纤维组合物以及其制造方法 |
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