CN1068812A - 水溶性生物降解聚碳酸酯的制备方法 - Google Patents
水溶性生物降解聚碳酸酯的制备方法 Download PDFInfo
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Abstract
通式如下的水溶性生物降解聚碳酸酯,
以及其作为合成纤维的制剂和润滑剂的用途。
Description
本发明涉及新的水溶及生物降解碳酸聚酯(聚碳酸酯)及它们作为合成纱的制剂和润滑剂的用途。
为了使由聚酯、聚酰胺、聚丙烯、聚丙烯腈,甚至再生纤维素所制合成纤维和合成纱能在高速下进行机械加工,而不会磨损和断裂,使用具有低挥发度和高闪点的抗静电,降摩擦油。一般来说,使用稀稠度的水不溶矿物油,酯油或聚醚作为这种“纺纱助剂”的基本成份(例如在美国专利3338830中所描述的);根据有关的要求,将它们用乳化剂调节成水混溶性的。
当合成纤维机械加工的速度提高时,特别是在摩擦卷曲的严酷条件下,纤维加工剂的机械和热稳定性变得更加重要了。在使用矿物油基产品时,在加热导轨上所产生的不期望的裂化渣油或焦油沉积,常常会给生产造成代价很高的中断。日本专利195437/83或欧洲专利0146234分别揭示了用某种类型的聚亚烷基二醇醚碳酸酯解决这一问题。然而根据结构和合成,仅能得到水不溶产品或在水中可乳化的那些产品。已证明使用在水中可自乳化的脂肪醇的环氧乙烷(环氧丙烷)加合物是有益的。它们可以以嵌段或无规加合物(带有无规链区)的形式存在。不过,由于它们的结构,它们缺乏润湿能力以及生物降解性能。
因此,本发明的目的是提供一种具有优异润湿性能和高的热稳定性的稀稠度水溶和可生物降解的产物,它适于用作纺纱助剂,即合成纱的制剂及润湿剂。
根据本发明,以下列通式的新型聚碳酸酯达到本发明的目的:
其中
R1是一个含6~22个碳原子的直链,或支链的,饱和或单不饱和的烷基,
R2是氢或甲基,
n是0~10的整数,
m是5~16的整数,
z是1~3的整数。
与通常制造的产品相比,此新型低聚低粘度聚亚烷基二醇的聚碳酸酯具有较低的凝固点,更良好的稠度(在室温下),改进的亲水性。它们显示润湿作用并且是可生物降解的。
本发明是基于下面的惊人发现:通过以碳酸酯基的形式引入酯基,水不溶伯醇及这种醇的部分水溶烷基-聚-乙二醇醚与聚亚烷基二醇的缩合反应可以如下方式进行;憎水性没有增强(这在酯的形成中是正常的),而且不是得到水溶化合物。正如在缩聚反应中是很正常的,单官能伯醇的作用是限制整个分子的分子量。因此获得了作为新型纤维制剂的如下结构:
a)完全缩合:
它们具有以下定义:
R1:含有6~22个碳原子的直链或支链的,饱和或单不饱和的烷基,
R2:氢或甲基,
n:0~10的整数,
m:5~16的整数,
z:1~3的整数。
如果包含在聚亚烷基二醇醚嵌段中的取代基R2重复出现,则在每种情况下它可以相同也可以不相同。在后一种情况下,它们是带有嵌段或无规链区的环氧乙烷和环氧丙烷的加合物。
由完全缩合所得到的分子可以分为中心亲水嵌段和两个端部的疏水基。因此优选聚乙二醇用作缩合物组份。用环氧丙烷制成的加合物含有至少80摩尔%的环氧乙烷,否则,聚碳酸酯的亲水性以及润湿性将会降低太多。
根据本发明的聚碳酸酯可用简单方式获得,即在碱催化剂下,使低沸点醇的碳酸酯例如碳酸二甲酯和碳酸二乙酯分别与聚亚烷基二醇及高分子醇或相应的烷基(聚一)-乙二醇醚发生酯基转移反应,将低分子醇经分馏柱蒸去。此反应可在有部分羟基化合物存在下进行,也可用所需的羟基化合物混合物直接进行。这样可以先制成高分子碳酸二烷基酯,然后使它与聚亚烷基二醇及低分子碳酸二烷基酯反应,并使之达到平衡。在反应终止后,需把碱性催化剂滤去,因为它不溶于产品中,因此可能造成混浊。假若使用碱土氧化物例如CaO作为酯基转移反应催化剂的话,这也可以很简单地进行。
另一方面,高分子量碳酸二烷基酯或聚碳酸酯的大规模制备可以在有足够的安全措施条件下分别用醇和聚亚烷基二醇的光气化反应来进行。
为了用烯化氧制备聚亚烷基二醇,通常用二醇作为原料,在最简单的情况下,使用水或乙二醇,然而也可用任何别的二价醇,例如1,2-丙二醇,1,3-丙二醇,1,2-丁二醇,1,4-丁二醇,1,6-己二醇,二乙二醇醚,或三乙二醇醚。
在这种情况下可以将碱类用作催化剂,例如氢氧化钠,氢氧化钾或它们的混合物,以及特殊的金属络合物例如六氰基钴酸钴。根据羟基数,被连接的聚醚的平均摩尔量应限于最高值为800,因为在多重连接的情况下,较高分子的加合物会导致所不希望的结构液体粘度的增加。
如果使用环氧乙烷和环氧丙烷的聚亚烷基二醇作为中心基团,则对于相应的分子结构没有限制。嵌段加合物和无规加合物均可使用,根据这一点,每一个双价二醇都能形成中心单元。
带有多于6个碳原子的合成直链或支链伯醇适于限制聚酯的摩尔量,这些伯醇的例子包括:己醇,辛醇,壬醇,癸醇,十一烷醇,十二烷醇,十三烷醇,十四烷醇,十五烷醇,十六烷醇,十七烷醇,十八烷醇,十九烷醇,二十烷醇,二十一烷醇和二十二烷醇,以及由天然脂肪得到的直链醇,例如己醇,庚醇,辛醇,壬醇,癸醇,月桂醇,肉豆寇醇,鲸蜡醇,硬脂醇,花生醇,和山嵛醇,以及单不饱和醇,例如油醇。它们可以未变化的形式使用,也可以羟乙基醚的形式使用。羟乙基醚是环氧乙烷的加成产物。每一摩尔醇类所加的环氧乙烷最大摩尔数为10,若数量超过这一限制,会导致最终产物的粘度太高。
根据本发明的水溶聚碳酸酯可用作合成纤维的润湿剂及制剂,特别是在摩擦卷曲工序,而不必加入其它组份或与其它组份一起混合。普通的添加剂是抗静电剂,抗腐蚀剂,防沫剂,防腐剂,还可以有增溶剂。
在纤维的纺丝过程中,当离开纺丝仓时,聚碳酸酯可以通过计量泵或给油辊而直接应用。此化合物可以实体应用,也可以水溶液应用。与使用至今的油形成对照,由于其高水溶性和润湿特性,已不再需要加入乳化剂。因为缩合产物是可完全生物降解的,所以在随后的洗涤操作中,当把本发明的制剂从纤维材料上部分洗去时,不存在环境问题。这样废水的处理就可以按照与通常洗涤剂和清洁剂所用的相同标准来进行。
本发明具有以下优点:
-与公知的水乳化油相比,由于更好的纤维润湿性和表面涂层,因此滑移性能得到改善。
-使用水溶和无乳化剂油的结果是在所有重要机器部件上的焦油和粘稠物沉积都同时减少了。由此细的和最细的纱的加工容易了,而且因高速而引起的静电问题减少了。
本发明将用下面的实施例作更详细的解释。
A)生产本发明的聚碳酸酯
例1
在一个带搅拌器,回流冷凝器和温度计的玻璃烧瓶中,将240克十二烷醇(Alfol 10,Condea AG)与150克碳酸二甲酯和8克氧化钙一起回流2小时。然后把回流冷凝器换成精馏柱,并把混合物在搅拌下慢慢加热至100℃。在精馏柱的顶部收集到酯基转移反应放出的甲醇及伴随的碳酸二甲酯。随后加入分子量为400的聚乙二醇600克和碳酸二甲酯100克。把混合物再回流2小时,然后把温度升至120℃,此间再有一些甲醇/碳酸二甲酯混合物被蒸出。最后使反应体系在短时间内处于真空状态。冷至室温后,过滤反应产物。它是一种清亮,无色,稀稠度的油。
例2
在例1的玻璃设备中,首先在搅拌条件下使365克乙氧基化癸醇(结合有2摩尔环氧乙烷的Alfol 10,Condea AG)与150克碳酸二甲酯及8克氧化钙缓慢回流,然后加热到100℃,此间释放出的甲醇与碳酸二甲酯一起被蒸出。然后加入600克聚乙二醇(分子量400)和100克碳酸二甲酯,此混合物按例1那样进行处理。把催化剂滤去后,得到一种清亮,稀稠度的无色油。
例3及以下的几例
反应条件及反应剂之间的摩尔比均与上述的相同。与碳酸二甲酯缩合的组分可取自下表1。
表1
反应剂1 反应剂2
例3 PEG 400 4EO-ALFOL10
例4 PEG 600 正 十二烷醇
例5 PEG/PPG 600 2 EO-ALFOL10
(80/20,无规)
某些产物数据与标样的比较
表2
纤维制剂 标样*1 2 3 4 5
粘度(布洛克菲尔德,mpas*) 180 150 150 160 170 170
表面张力(mN/m 10%) 29 30 29 29 29 30
水溶解度(10%) ······清亮······
裂化渣油(220℃,24小时,%) 1 1 1 1 1 1
标样*=Puropol FT 509(Stockhausen GmbH)。因为这样的产品没有表面活性或界面活性,故加入2%非离子润湿剂(乙氧基化脂肪醇Intrasol FA 1218/10)。
B)用作纺丝助剂
a)摩擦系数的测定:
用聚碳酸酯按照例1~5从水溶液中制备PES长丝(对苯二甲酸酯,167dtex 32f),其方式是要获得0.5%的油涂覆。
在20℃和65%相对湿度中进行空调24小时后,用F计(Rothschild)测定滑动摩擦系数,摩擦体由镀铬和抛光钢组成。
在17cN予拉伸下的摩擦系数:
第1批:纤维/金属(50米/分);抱合角180°
第2批:纤维/纤维(20米/分);抱合角6×180°
标样 1 2 3 4 5
1)0.41 0.40 0.40 0.41 0.41 0.41
2)0.31 0.31 0.30 0.30 0.31 0.31
b)聚酯一部分取向丝(纤度290dtex 32f)的制备:
当熔融聚合物从纺丝仓中的纺丝喷嘴出来后立即施加制剂,方法是用计量泵施以配成的10%水溶液。
卷绕速度为3200米/分。覆在部分取向丝材料上的制剂为0.4%。
c)摩擦变形(最终纤度167dtex 32f):
在下列条件下进行变形:
加热器长度:2.0米
加热器温度:210℃
冷却板:1.5米
摩擦单元:8块陶瓷片
拉出速度:700米/分
D/Y比率:2.2
拉伸率:1.608
得到下列测定值:
标样 例1~5
1 2 3 4 5
强度(cN、dtex): 3.63 3.65 3.66 3.64 3.66 3.64
伸长率(%): 25.0 25.0 25.1 25.1 25.2 25.1
沸腾时的收缩(%): 8.5 8.7 8.7 8.6 8.7 8.6
卷曲E(%) 41.2 41.1 41.2 41.2 41.2 41.1
卷曲K(%) 24.7 24.9 24.9 24.8 24.7 24.8
在测试条件下连续运行10天之后,在加热器内未发现沉积物。
d)生物降解性能:
为了测定生物降解性,将标准产物和根据例1~5的聚碳酸酯按OECO进行“证实检定”,28天之后,得到下列结果:
标准物 例1~5
生物降解(%) 20 80
应该理解,说明书和实例是用于说明本发明而不是对其加以限制的,在本发明的精神和范围内本技术领域熟练人员可以提出一些其它具体实例。
例6~10
6)在一个例1的玻璃设备中,将366克正己醇(结合有6摩尔环氧乙烷)与150克碳酸二甲酯和8克氧化钙一起加热。2小时后,加入600克聚乙二醇(m=400),再加入220克碳酸二甲酯。将混合物再回流2小时,然后把甲醇与碳酸二甲酯的共沸混合物蒸去。最后,使反应体系在短时间内处于真空状态。冷却后,把反应产物滤出,得到一种清亮,颜色鲜明,水不溶的油。
7)按照例6,使482克2-乙基己醇(结合8摩尔环氧乙烷)与300克聚乙二醇(m=600)及总数为210克(150/60)的碳酸二甲酯反应。待共沸混合物被蒸出并除去催化剂之后,得到一种颜色鲜明的油,此油在贮存时生成少量固体沉积物。
8)按照例6,将620克已与8摩尔环氧乙烷反应的油醇(Ocenol 60/65,Henkel KGaA)与150克碳酸二甲酯及8克氧化钙一起加热。随后,加入1200克聚乙二醇(m=600)并再加入220克碳酸二甲酯,并把释放出的甲醇作为共沸混合物蒸掉。在60℃把产物过滤后,得到一种蜡。其在室温下是软的,且是水溶的。
9)按照例6,将422克已与6摩尔环氧乙烷反应的正癸醇(Alfol 10,Condea AG)与600克聚乙二醇(m=200)及450克碳酸二甲酯(150/300)一起加热。在蒸去共沸混合物及除去催化剂后,得到一种颜色鲜明,稀稠度的水溶性油。
10)按照例6,将756克山嵛醇(附有10摩尔环氧乙烷)与1200克聚乙二醇(m=600)及总数为370克的碳酸二甲酯反应。在60℃反应后,得到一种颜色鲜明的水溶性蜡。
例6~10的测试结果
Claims (3)
3、一种生产合成纤维的制剂和润滑剂的方法,其特征在于往根据权利要求1~2所得到的聚碳酸酯中加入作为必要成分的抗静电剂,抗腐蚀剂,防沫剂,防腐剂,和/或增溶剂。
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DEP4113889.9 | 1991-04-27 | ||
DE4113889A DE4113889C2 (de) | 1991-04-27 | 1991-04-27 | Neue wasserlösliche biologisch abbaubare Kohlensäurepolyester und ihre Verwendung als Präparations- und Gleitmittel für Synthesegarne |
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US (1) | US5569408A (zh) |
EP (2) | EP0582602A1 (zh) |
JP (1) | JP2651510B2 (zh) |
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DE (2) | DE4113889C2 (zh) |
DK (1) | DK0511589T3 (zh) |
ES (2) | ES2061417T1 (zh) |
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CN111978531A (zh) * | 2020-08-26 | 2020-11-24 | 烟台大学 | 纤维素接枝型全生物降解高分子材料及其制备方法 |
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- 1991-04-27 DE DE4113889A patent/DE4113889C2/de not_active Revoked
-
1992
- 1992-04-23 EP EP92909074A patent/EP0582602A1/de active Pending
- 1992-04-23 WO PCT/EP1992/000894 patent/WO1992019664A1/de not_active Application Discontinuation
- 1992-04-23 DE DE59209726T patent/DE59209726D1/de not_active Expired - Fee Related
- 1992-04-23 EP EP19920106958 patent/EP0511589B1/de not_active Expired - Lifetime
- 1992-04-23 ES ES92909074T patent/ES2061417T1/es active Pending
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- 1992-04-23 UA UA94041000A patent/UA39928C2/uk unknown
- 1992-04-23 DK DK92106958T patent/DK0511589T3/da active
- 1992-04-23 ES ES92106958T patent/ES2136607T3/es not_active Expired - Lifetime
- 1992-04-23 AT AT92106958T patent/ATE182343T1/de not_active IP Right Cessation
- 1992-04-23 US US08/140,048 patent/US5569408A/en not_active Expired - Fee Related
- 1992-04-27 CN CN92103992A patent/CN1041837C/zh not_active Expired - Fee Related
- 1992-05-08 TW TW081103600A patent/TW374778B/zh active
-
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CN102597361A (zh) * | 2009-09-03 | 2012-07-18 | 帝人芳纶有限公司 | 由芳族聚酰胺纤维制成的织物及其用途 |
CN102597361B (zh) * | 2009-09-03 | 2014-07-16 | 帝人芳纶有限公司 | 由芳族聚酰胺纤维制成的织物及其用途 |
CN103339240A (zh) * | 2011-02-10 | 2013-10-02 | 株式会社Moresco | 轴承用润滑剂及其应用 |
US8916509B2 (en) | 2011-02-10 | 2014-12-23 | Moresco Corporation | Bearing lubricant and use thereof |
CN104499289A (zh) * | 2014-12-17 | 2015-04-08 | 义乌市金通化工有限公司 | 一种以碳酸酯为基础原料的涤纶纺丝油剂 |
CN111978531A (zh) * | 2020-08-26 | 2020-11-24 | 烟台大学 | 纤维素接枝型全生物降解高分子材料及其制备方法 |
Also Published As
Publication number | Publication date |
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JP2651510B2 (ja) | 1997-09-10 |
CN1041837C (zh) | 1999-01-27 |
DE4113889C2 (de) | 1994-05-11 |
GR940300019T1 (en) | 1994-04-29 |
EP0511589B1 (de) | 1999-07-21 |
US5569408A (en) | 1996-10-29 |
EP0511589A1 (de) | 1992-11-04 |
GR3031566T3 (en) | 2000-01-31 |
WO1992019664A1 (de) | 1992-11-12 |
ES2136607T3 (es) | 1999-12-01 |
TW374778B (en) | 1999-11-21 |
JPH06509593A (ja) | 1994-10-27 |
UA39928C2 (uk) | 2001-07-16 |
ES2061417T1 (es) | 1994-12-16 |
ATE182343T1 (de) | 1999-08-15 |
DE4113889A1 (de) | 1992-10-29 |
DK0511589T3 (da) | 2000-02-07 |
EP0582602A1 (de) | 1994-02-16 |
DE59209726D1 (de) | 1999-08-26 |
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