CN107011681A - A kind of method that polypropylene glycol improves polypropylene sorrel water resistance and compliance with PPDO - Google Patents
A kind of method that polypropylene glycol improves polypropylene sorrel water resistance and compliance with PPDO Download PDFInfo
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Abstract
本发明公开一种聚丙二醇与聚对二氧环己酮改良聚丙烯酸膜耐水性及柔顺性的方法，采用以下步骤：1）干燥反应器内加入羟基封端的聚丙二醇单丁醚、溶剂、缩合剂和聚丙烯酸，反应2～4天，得到聚丙烯酸‑聚丙二醇接枝共聚物；2）干燥反应器内加入接枝共聚物、羟基封端的聚对二氧环己酮单十二烷基醚、溶剂和缩合剂，反应2～4天，得到聚丙烯酸‑聚丙二醇‑聚对二氧环己酮双接枝共聚物；3）干燥反应器内加入双接枝共聚物、聚对二氧环己酮单十二烷基醚和溶剂，混合50～60分钟后，用流延法成膜并干燥，得到本发明目标物。本发明制备工艺简单、易于掌握，所得改性膜耐水性及柔顺性有了很大的提高。The invention discloses a method for improving the water resistance and flexibility of polyacrylic acid film with polypropylene glycol and polydioxanone. Mixture and polyacrylic acid, react for 2 to 4 days to obtain polyacrylic acid-polypropylene glycol graft copolymer; 2) Add graft copolymer and hydroxyl-terminated polydioxanone monolauryl ether into the drying reactor , solvent and condensing agent, react for 2 to 4 days to obtain polyacrylic acid-polypropylene glycol-polydioxanone double graft copolymer; 3) add double graft copolymer, polydioxane Hexanone monododecyl ether and solvent are mixed for 50 to 60 minutes, then cast into a film and dried to obtain the object of the present invention. The preparation process of the invention is simple and easy to master, and the water resistance and flexibility of the obtained modified membrane are greatly improved.
Description
技术领域technical field
本发明涉及一种对聚丙烯酸膜耐水性及柔顺性进行改良的方法，属于聚合物薄膜制备技术领域。The invention relates to a method for improving the water resistance and flexibility of polyacrylic acid films, and belongs to the technical field of polymer film preparation.
背景技术Background technique
聚丙烯酸是一种具有良好的生物相容性和生物可降解性的生物材料，聚丙烯酸膜可用作人造皮肤等，但聚丙烯酸膜亲水性太强且较僵硬，缺乏较好的耐水性及柔顺性，从而一定程度上限制了其应用。聚丙二醇（分子量2000以上）和聚对二氧环己酮是具有优良的生物相容性和生物可降解性的生物材料，具有疏水性和柔顺性。先将聚丙二醇链段接枝到聚丙烯酸分子链上得到聚丙烯酸-聚丙二醇接枝共聚物，再将聚对二氧环己酮链段接枝到聚丙烯酸-聚丙二醇接枝共聚物中的聚丙烯酸链段上形成聚丙烯酸-聚丙二醇-聚对二氧环己酮双接枝共聚物，然后再将聚对二氧环己酮链段加入聚丙烯酸-聚丙二醇-聚对二氧环己酮双接枝共聚物形成共混物，制得改性聚丙烯酸膜，从而极大地提高了聚丙烯酸膜的耐水性及柔顺性。Polyacrylic acid is a biomaterial with good biocompatibility and biodegradability. Polyacrylic acid film can be used as artificial skin, etc., but polyacrylic acid film is too hydrophilic and stiff, and lacks good water resistance. and flexibility, which limits its application to a certain extent. Polypropylene glycol (more than 2000 molecular weight) and polydioxanone are biomaterials with excellent biocompatibility and biodegradability, and are hydrophobic and flexible. First, the polypropylene glycol segment is grafted onto the polyacrylic acid molecular chain to obtain a polyacrylic acid-polypropylene glycol graft copolymer, and then the polydioxanone segment is grafted into the polyacrylic acid-polypropylene glycol graft copolymer. Polyacrylic acid-polypropylene glycol-polydioxanone double graft copolymer is formed on the polyacrylic acid segment, and then the polydioxanone segment is added to the polyacrylic acid-polypropylene glycol-polydioxanone The ketone double-graft copolymer forms a blend to prepare a modified polyacrylic acid film, thereby greatly improving the water resistance and flexibility of the polyacrylic acid film.
发明内容Contents of the invention
本发明的目的在于提供一种操作简单及效果较好的对聚丙烯酸膜耐水性及柔顺性进行改良的方法。其技术方案为：The object of the present invention is to provide a method for improving the water resistance and flexibility of polyacrylic film with simple operation and good effect. Its technical solution is:
一种聚丙二醇与聚对二氧环己酮改良聚丙烯酸膜耐水性及柔顺性的方法，其特征在于：改性膜中聚丙烯酸链段的分子量为80000～93000，聚丙二醇链段的分子量为2500～2700，聚对二氧环己酮链段的分子量为2300～2500；其改性方法采用以下步骤：A method for improving the water resistance and flexibility of polyacrylic acid films with polypropylene glycol and polydioxanone, characterized in that: the molecular weight of polyacrylic acid segments in the modified film is 80,000 to 93,000, and the molecular weight of polypropylene glycol segments is 2500-2700, the molecular weight of the polydioxanone segment is 2300-2500; the modification method adopts the following steps:
1）聚丙烯酸-聚丙二醇接枝共聚物的合成：在干燥反应器内加入羟基封端的聚丙二醇单丁醚、溶剂、缩合剂和聚丙烯酸，惰性气氛下，于27～35℃搅拌反应2～4天，终止反应，通过过滤、透析、干燥，得到目标物；1) Synthesis of polyacrylic acid-polypropylene glycol graft copolymer: Add hydroxyl-terminated polypropylene glycol monobutyl ether, solvent, condensing agent and polyacrylic acid into a dry reactor, and stir at 27-35°C for 2- After 4 days, the reaction was terminated, and the target object was obtained by filtration, dialysis, and drying;
2）聚丙烯酸-聚丙二醇-聚对二氧环己酮双接枝共聚物的合成：在干燥反应器内加入聚丙烯酸-聚丙二醇接枝共聚物、羟基封端的聚对二氧环己酮单十二烷基醚、溶剂和缩合剂，惰性气氛下，于27～33℃搅拌反应2～4天，终止反应，通过过滤、透析、干燥，得到目标物；2) Synthesis of polyacrylic acid-polypropylene glycol-polydioxanone double graft copolymer: add polyacrylic acid-polypropylene glycol graft copolymer, hydroxyl-terminated polydioxanone Lauryl ether, solvent and condensing agent, under an inert atmosphere, stirred and reacted at 27-33°C for 2-4 days, terminated the reaction, and obtained the target product by filtration, dialysis and drying;
3）聚丙二醇与聚对二氧环己酮改良的聚丙烯酸膜的制备：在干燥反应器内加入聚丙烯酸-聚丙二醇-聚对二氧环己酮双接枝共聚物、聚对二氧环己酮单十二烷基醚和溶剂，惰性气氛下，于47～53℃搅拌混合50～60分钟后，用流延法成膜并干燥，得到目标物。3) Preparation of polyacrylic acid film modified by polypropylene glycol and polydioxanone: add polyacrylic acid-polypropylene glycol-polydioxanone double graft copolymer, polydioxanone Hexanone monododecyl ether and a solvent are stirred and mixed at 47-53° C. for 50-60 minutes under an inert atmosphere, and then formed into a film by casting method and dried to obtain the target product.
所述的一种聚丙二醇与聚对二氧环己酮改良聚丙烯酸膜耐水性及柔顺性的方法，步骤1）中，聚丙二醇单丁醚与聚丙烯酸的摩尔比为15～25:1。In the method for improving the water resistance and flexibility of polyacrylic acid film with polypropylene glycol and polydioxanone, in step 1), the molar ratio of polypropylene glycol monobutyl ether to polyacrylic acid is 15-25:1.
所述的一种聚丙二醇与聚对二氧环己酮改良聚丙烯酸膜耐水性及柔顺性的方法，步骤1）中，缩合剂采用N,N’-二环己基碳二亚胺、N,N’-二异丙基碳二亚胺或3-乙基-1-（3-二甲氨丙基）碳二亚胺，缩合剂与聚丙烯酸的摩尔比为1.06～1.8:1，溶剂采用二甲基亚砜，反应物溶液浓度为5～15 g:100 ml。In the method for improving the water resistance and flexibility of polyacrylic acid film with polypropylene glycol and polydioxanone, in step 1), the condensing agent is N,N' -dicyclohexylcarbodiimide, N, N' -diisopropylcarbodiimide or 3-ethyl-1-(3-dimethylaminopropyl)carbodiimide, the molar ratio of condensing agent to polyacrylic acid is 1.06～1.8:1, and the solvent is Dimethyl sulfoxide, the concentration of the reactant solution is 5-15 g:100 ml.
所述的一种聚丙二醇与聚对二氧环己酮改良聚丙烯酸膜耐水性及柔顺性的方法，步骤2）中，聚对二氧环己酮单十二烷基醚与聚丙烯酸-聚丙二醇接枝共聚物中聚丙烯酸链段的摩尔比为15～25:1。The method for improving the water resistance and flexibility of polyacrylic acid film with polypropylene glycol and polydioxanone, in step 2), polydioxanone monolauryl ether and polyacrylic acid-poly The molar ratio of the polyacrylic acid segment in the propylene glycol graft copolymer is 15-25:1.
所述的一种聚丙二醇与聚对二氧环己酮改良聚丙烯酸膜耐水性及柔顺性的方法，步骤2）中，缩合剂采用N,N’-二环己基碳二亚胺、N,N’-二异丙基碳二亚胺或3-乙基-1-（3-二甲氨丙基）碳二亚胺，缩合剂与聚丙烯酸-聚丙二醇接枝共聚物中聚丙烯酸链段的摩尔比为1.06～1.8:1，溶剂采用二甲基亚砜，反应物溶液浓度为5～15 g:100 ml。In the method for improving the water resistance and flexibility of polyacrylic acid film with polypropylene glycol and polydioxanone, in step 2), the condensing agent is N,N' -dicyclohexylcarbodiimide, N, N' -diisopropylcarbodiimide or 3-ethyl-1-(3-dimethylaminopropyl)carbodiimide, condensing agent and polyacrylic acid segment in polyacrylic acid-polypropylene glycol graft copolymer The molar ratio is 1.06-1.8:1, the solvent is dimethyl sulfoxide, and the concentration of the reactant solution is 5-15 g:100 ml.
所述的一种聚丙二醇与聚对二氧环己酮改良聚丙烯酸膜耐水性及柔顺性的方法，步骤3）中，聚对二氧环己酮单十二烷基醚在改性膜中的质量百分比为2～4%，溶剂采用二甲基亚砜，混合物溶液浓度为25～30 g:100 ml。In the method for improving the water resistance and flexibility of polyacrylic acid film with polypropylene glycol and polydioxanone, in step 3), polydioxanone monolauryl ether is added to the modified film The mass percentage is 2-4%, the solvent is dimethyl sulfoxide, and the concentration of the mixture solution is 25-30 g:100 ml.
本发明与现有技术相比，其优点为：Compared with the prior art, the present invention has the advantages of:
1、所述的一种聚丙二醇与聚对二氧环己酮改良聚丙烯酸膜耐水性及柔顺性的方法，采用两步酯化反应和共混相结合的手段，操作简单、易于掌握；1. The method for improving the water resistance and flexibility of polyacrylic acid films with polypropylene glycol and polydioxanone adopts the means of combining two-step esterification and blending, which is simple to operate and easy to master;
2、所述的聚丙烯酸改良膜耐水性及柔顺性有了较大的提高。2. The water resistance and flexibility of the polyacrylic acid modified film have been greatly improved.
具体实施方式detailed description
实施例1Example 1
1）聚丙烯酸-聚丙二醇接枝共聚物的制备1) Preparation of polyacrylic acid-polypropylene glycol graft copolymer
在干燥反应器内加入15.3克聚丙烯酸（分子量为80000）、8.8克羟基封端的聚丙二醇单丁醚（分子量为2500），加入241 ml二甲基亚砜，再加入0.049克N,N’-二环己基碳二亚胺，惰性气氛下，于27℃搅拌反应2天，终止反应，通过过滤、透析、干燥，得到目标物；Add 15.3 g of polyacrylic acid (molecular weight: 80,000), 8.8 g of hydroxyl-terminated polypropylene glycol monobutyl ether (molecular weight: 2,500), 241 ml of dimethyl sulfoxide, and 0.049 g of N,N'- Dicyclohexylcarbodiimide, under an inert atmosphere, stirred and reacted at 27°C for 2 days, terminated the reaction, and obtained the target product by filtration, dialysis, and drying;
2）聚丙烯酸-聚丙二醇-聚对二氧环己酮双接枝共聚物的制备2) Preparation of polyacrylic acid-polypropylene glycol-polydioxanone double graft copolymer
在干燥反应器内加入12.1克聚丙烯酸-聚丙二醇接枝共聚物、6.5克羟基封端的聚对二氧环己酮单十二烷基醚（分子量为2300），加入186 ml二甲基亚砜，再加入0.036克N,N’-二环己基碳二亚胺，惰性气氛下，于27℃搅拌反应2天，终止反应，通过过滤、透析、干燥，得到目标物；Add 12.1 grams of polyacrylic acid-polypropylene glycol graft copolymer, 6.5 grams of hydroxyl-terminated polydioxanone monolauryl ether (molecular weight: 2300), and 186 ml of dimethyl sulfoxide into the dry reactor , then add 0.036 g of N,N' -dicyclohexylcarbodiimide, under an inert atmosphere, stir and react at 27°C for 2 days, terminate the reaction, and obtain the target compound by filtration, dialysis and drying;
3）聚丙二醇与聚对二氧环己酮改良的聚丙烯酸膜的制备3) Preparation of polyacrylic acid film modified by polypropylene glycol and polydioxanone
在干燥反应器内加入10克聚丙烯酸-聚丙二醇-聚对二氧环己酮双接枝共聚物和37 ml二甲基亚砜溶剂，另加入占改性膜总重量2%的聚对二氧环己酮单十二烷基醚（分子量为2300），惰性气氛下，于47℃搅拌混合50分钟，用流延法成膜，在50℃真空干燥箱中干燥得到目标物。Add 10 grams of polyacrylic acid-polypropylene glycol-polydioxanone double-graft copolymer and 37 ml of dimethyl sulfoxide solvent in the dry reactor, and add 2% of the total weight of the modified membrane. Oxycyclohexanone monolauryl ether (molecular weight: 2300), stirred and mixed at 47°C for 50 minutes under an inert atmosphere, formed a film by casting method, and dried in a vacuum oven at 50°C to obtain the target product.
经测试：本发明目标物与水的表面接触角及其断裂伸长率分别比改性前提高了12.2°和9.2%。After testing: the surface contact angle of the object of the present invention and water and its elongation at break are respectively increased by 12.2° and 9.2% compared with those before modification.
实施例2Example 2
1）聚丙烯酸-聚丙二醇接枝共聚物的制备1) Preparation of polyacrylic acid-polypropylene glycol graft copolymer
在干燥反应器内加入15克聚丙烯酸（分子量为87000）、8.7克羟基封端的聚丙二醇单丁醚（分子量为2600），加入236 ml二甲基亚砜，再加入0.028克N,N’-二异丙基碳二亚胺，惰性气氛下，于30℃搅拌反应3天，终止反应，通过过滤、透析、干燥，得到目标物；Add 15 grams of polyacrylic acid (molecular weight: 87,000), 8.7 grams of hydroxyl-terminated polypropylene glycol monobutyl ether (molecular weight: 2,600), 236 ml of dimethyl sulfoxide, and 0.028 grams of N,N'- Diisopropylcarbodiimide, under an inert atmosphere, stirred and reacted at 30°C for 3 days, terminated the reaction, and obtained the target product by filtration, dialysis, and drying;
2）聚丙烯酸-聚丙二醇-聚对二氧环己酮双接枝共聚物的制备2) Preparation of polyacrylic acid-polypropylene glycol-polydioxanone double graft copolymer
在干燥反应器内加入12.2克聚丙烯酸-聚丙二醇接枝共聚物、6.4克羟基封端的聚对二氧环己酮单十二烷基醚（分子量为2400），加入186 ml二甲基亚砜，再加入0.022克N,N’-二异丙基碳二亚胺，惰性气氛下，于30℃搅拌反应3天，终止反应，通过过滤、透析、干燥，得到目标物；Add 12.2 grams of polyacrylic acid-polypropylene glycol graft copolymer, 6.4 grams of hydroxyl-terminated polydioxanone monolauryl ether (molecular weight: 2400), and 186 ml of dimethyl sulfoxide into the dry reactor , then add 0.022 g of N,N' -diisopropylcarbodiimide, under an inert atmosphere, stir and react at 30°C for 3 days, terminate the reaction, and obtain the target product by filtration, dialysis and drying;
3）聚丙二醇与聚对二氧环己酮改良的聚丙烯酸膜的制备3) Preparation of polyacrylic acid film modified by polypropylene glycol and polydioxanone
在干燥反应器内加入9.9克聚丙烯酸-聚丙二醇-聚对二氧环己酮双接枝共聚物和36ml二甲基亚砜溶剂，另加入占改性膜总重量3%的聚对二氧环己酮单十二烷基醚（分子量为2400），惰性气氛下，于49℃搅拌混合55分钟，用流延法成膜，在50℃真空干燥箱中干燥得到目标物。Add 9.9 grams of polyacrylic acid-polypropylene glycol-polydioxanone double-graft copolymer and 36ml of dimethyl sulfoxide solvent in the drying reactor, and add 3% of the modified membrane gross weight in addition. Cyclohexanone monododecyl ether (molecular weight: 2400), stirred and mixed at 49°C for 55 minutes under an inert atmosphere, formed a film by casting method, and dried in a vacuum oven at 50°C to obtain the target product.
经测试：本发明目标物与水的表面接触角及其断裂伸长率分别比改性前提高了12.8°和10.1%。After testing: the surface contact angle of the object of the present invention with water and the elongation at break are respectively increased by 12.8° and 10.1% compared with those before modification.
实施例3Example 3
1）聚丙烯酸-聚丙二醇接枝共聚物的制备1) Preparation of polyacrylic acid-polypropylene glycol graft copolymer
在干燥反应器内加入15.8克聚丙烯酸（分子量为93000）、8.7克羟基封端的聚丙二醇单丁醚（分子量为2700），加入244 ml二甲基亚砜，再加入0.041克3-乙基-1-（3-二甲氨丙基）碳二亚胺，惰性气氛下，于35℃搅拌反应4天，终止反应，通过过滤、透析、干燥，得到目标物；Add 15.8 grams of polyacrylic acid (molecular weight: 93,000), 8.7 grams of hydroxyl-terminated polypropylene glycol monobutyl ether (molecular weight: 2,700), 244 ml of dimethyl sulfoxide, and 0.041 grams of 3-ethyl- 1-(3-Dimethylaminopropyl) carbodiimide, stirred and reacted at 35°C for 4 days under an inert atmosphere, the reaction was terminated, and the target product was obtained by filtration, dialysis and drying;
2）聚丙烯酸-聚丙二醇-聚对二氧环己酮双接枝共聚物的制备2) Preparation of polyacrylic acid-polypropylene glycol-polydioxanone double graft copolymer
在干燥反应器内加入11.6克聚丙烯酸-聚丙二醇接枝共聚物、5.8克羟基封端的聚对二氧环己酮单十二烷基醚（分子量为2500），加入173 ml二甲基亚砜，再加入0.028克3-乙基-1-（3-二甲氨丙基）碳二亚胺，惰性气氛下，于33℃搅拌反应4天，终止反应，通过过滤、透析、干燥，得到目标物；Add 11.6 grams of polyacrylic acid-polypropylene glycol graft copolymer, 5.8 grams of hydroxyl-terminated polydioxanone monolauryl ether (molecular weight: 2500), and 173 ml of dimethyl sulfoxide into the dry reactor , then add 0.028 g of 3-ethyl-1-(3-dimethylaminopropyl) carbodiimide, under an inert atmosphere, stir the reaction at 33°C for 4 days, terminate the reaction, and obtain the target thing;
3）聚丙二醇与聚对二氧环己酮改良的聚丙烯酸膜的制备3) Preparation of polyacrylic acid film modified by polypropylene glycol and polydioxanone
在干燥反应器内加入9.5克聚丙烯酸-聚丙二醇-聚对二氧环己酮双接枝共聚物和35ml二甲基亚砜溶剂，另加入占改性膜总重量4%的聚对二氧环己酮单十二烷基醚（分子量为2500），惰性气氛下，于53℃搅拌混合60分钟，用流延法成膜，在50℃真空干燥箱中干燥得到目标物。Add 9.5 grams of polyacrylic acid-polypropylene glycol-polydioxanone double-graft copolymer and 35ml of dimethyl sulfoxide solvent in the dry reactor, and add 4% of the modified membrane gross weight in addition. Cyclohexanone monododecyl ether (molecular weight: 2500), stirred and mixed at 53°C for 60 minutes under an inert atmosphere, formed into a film by casting method, and dried in a vacuum oven at 50°C to obtain the target product.
经测试：本发明目标物与水的表面接触角及其断裂伸长率分别比改性前提高了13.5°和10.8%。After testing: the surface contact angle of the object of the present invention with water and the elongation at break are respectively increased by 13.5° and 10.8% compared with those before modification.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104479158A (en) * | 2015-01-06 | 2015-04-01 | 山东理工大学 | Method for improving hydrophilia and flexibility of polypeptide membrane through polydioxanone and polyethylene glycol |
| CN105542207A (en) * | 2016-03-07 | 2016-05-04 | 山东理工大学 | Method for improving water resistance and flexibility of polyvinyl alcohol film through polypropylene glycol and polypeptide-polyvinylpyrrolidone |
| CN105670306A (en) * | 2016-03-07 | 2016-06-15 | 山东理工大学 | Method for improving water resistance and flexibility of polyvinyl alcohol film by using poly(p-dioxanone) and polypeptide |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104479158A (en) * | 2015-01-06 | 2015-04-01 | 山东理工大学 | Method for improving hydrophilia and flexibility of polypeptide membrane through polydioxanone and polyethylene glycol |
| CN105542207A (en) * | 2016-03-07 | 2016-05-04 | 山东理工大学 | Method for improving water resistance and flexibility of polyvinyl alcohol film through polypropylene glycol and polypeptide-polyvinylpyrrolidone |
| CN105670306A (en) * | 2016-03-07 | 2016-06-15 | 山东理工大学 | Method for improving water resistance and flexibility of polyvinyl alcohol film by using poly(p-dioxanone) and polypeptide |
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