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Fluorinated polyesters with low surface energy and preparation method thereof

A low surface energy, fluorine-containing polyester technology, applied in the field of polymer materials, can solve problems such as inability to melt, complicated construction process, and poor adhesion

Inactive Publication Date: 2008-03-12
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The excellent anti-fouling performance of fluorine-containing materials reflects the surface properties of the material. Only the surface of the material is required to have a high fluorine content. The fluorine contained in the material body cannot contribute to its surface properties. Moreover, the fluorine contained in the body In addition to the waste of fluorine resources, the fluorine element also brings other problems, such as the traditional polytetrafluoroethylene cannot be dissolved or melted, and the processability is poor. The process is complicated, and the adhesion with the substrate or other materials is poor, so its application range is limited to a certain extent
[0004] Chinese invention patent (CN1450091A) reports a preparation method of low surface energy fluorocarbon resin, which is obtained by polymerization of tetrafluoroethylene, chlorotrifluoroethylene and organosilicone ester compound monomers. Expensive raw materials lead to its Increased costs
Huang Weiyuan, Zhang Li (CN1171408A) reported that the fluorine-containing aromatic polyester uses hydroquinone and dibasic acid as raw materials, and introduces fluorine-containing side groups on the polycondensate, but the melting point of this series of fluorine-containing aromatic polyester is as high as 360 ° C. Not for use in powder coatings
Isbrandt, Russell R. etc. (EP10027) can produce insoluble gel during the preparation process of the acrylic structure fluorine-containing urethane, and the hydrophobic and oleophobic properties are not ideal

Method used

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  • Fluorinated polyesters with low surface energy and preparation method thereof
  • Fluorinated polyesters with low surface energy and preparation method thereof
  • Fluorinated polyesters with low surface energy and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Synthesis of N-hydroxyethyl perfluorooctylamide-terminated polybutylene isophthalate

[0035] Preheat the reaction system to 110°C, add 0.05mol dimethyl isophthalate, 0.047mol 1,4-butanediol, 0.003mol N-hydroxyethyl perfluorooctylamide and 0.1% (wt% )Tetrabutyl titanate. React at 160-180°C for 1 hour. Start vacuuming, and heat up at the same time, at a temperature of 200-215° C., a vacuum of 85 mmHg, and react for 1.5 hours. Vacuum degree rises to 14mmHg, raise reaction temperature at the same time, react between 240-248 ℃ for 1.5 hours, stop heating, wait for the temperature in the reaction bottle to drop below 100 ℃, stop vacuuming. Add 50ml of chloroform to the product to dissolve the heat, then filter it with suction, settle the filtrate with 500ml of ethanol, dry the obtained solid, and grind it to obtain a solid product. Yield: 86.5%. The reaction molecular formula is as follows (wherein x=y+z, y / x+y+z=0.03):

[0036]

[0037]

[0038]

[0039] Raise t...

Embodiment 3

[0044] Synthesis of N-hydroxyethyl perfluorooctylamide-terminated polybutylene isophthalate

[0045] Preheat the reaction system to 110°C, add 0.05mol dimethyl isophthalate, 0.044mol 1,3-propanediol, 0.006mol pentafluorooctyl alcohol, and 0.1% (wt%) iso-titanate together under stirring nitrogen Propyl ester. React at 160-180°C for 1 hour. Start vacuuming and heat up at the same time, at a temperature of 200-210° C. and a vacuum of 85 mmHg, react for 1.5 hours. Vacuum degree rises to 14mmHg, raise reaction temperature at the same time, react between 240-245 ℃ for 1.5 hours, stop heating, wait until the temperature in the reaction bottle drops below 100 ℃, stop vacuuming. Add 50ml of chloroform to the product to dissolve the heat, then filter it with suction, settle the filtrate with 500ml of ethanol, dry the obtained solid, and grind it to obtain a solid product. Yield: 88%. The reaction molecular formula is as follows (wherein x=y+z, y / x+y+z=0.06):

[0046]

[0047] ...

Embodiment 4

[0050] Synthesis of dodecafluoroheptanol-terminated polybutylene isophthalate

[0051] Preheat the reaction system to 110°C, add 0.05mol dimethyl isophthalate, 0.046mol 2,2-dimethyl-1,3 propanediol, 0.004mol N-hydroxyethyl perfluorodecylamide, and 0.1% (wt%) tetrabutyl titanate. React at 170-180°C for 1 hour. Start vacuuming, and heat up at the same time, at a temperature of 205-215° C., a vacuum of 100 mmHg, and react for 1.5 hours. The vacuum degree was raised to 15mmHg, and the reaction temperature was increased at the same time, and the reaction was between 240-248°C for 1.5 hours, and the heating was stopped. When the temperature in the reaction bottle dropped below 100°C, the vacuum was stopped. Add 50ml of chloroform to the product to dissolve the heat, then dissolve it with suction, settle the filtrate with 500ml of ethanol, dry the obtained solid, and grind it to obtain a solid product. Yield: 90%. The reaction molecular formula is as follows (wherein x=y+z, y / x+y...

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Abstract

The present invention belongs to the field of mnacromolecule, relating to the fluorine-containing polyester of low surface energy and the preparation method of the fluorine-containing polyester. The polyester has the following chemical structure (1): wherein R f C is the straight chain of 2 - 21 C or the branch-chain pseudo-perfluoroalkyl; R1, R2 is the alkyl, aryl, or naphthenic base of the C1-C8; E is -(CH2) m-; formula (3) or formula (4); R' is H or the straight chain or the branch-chain alkyl under C4; m is an integer between 0 or 10. The polyester preparation method is that dibasic acid or the correspondent diester, dihydric alcohol and perfluoroalkane, which are 0.05 percent to 10 percent of the total material weight, are fused and polymerized under vacuum condition. The polyester preparation method at the pseudo-perfluoroalkyl sealed end is simple, and is of good drainage and oil dredging properties. The present invention can be widely used in antifouling coatings, and is of important development and application value.

Description

technical field [0001] The invention belongs to the field of polymer materials, and relates to a fluorine-containing polyester with low surface energy and a preparation method thereof. In particular, dimethyl isophthalate and butanediol are transesterified by transesterification, and N-hydroxyethyl perfluorooctylamide, a fluorine-containing end-capping agent, is added to prepare polyester materials with low fluorine content and good stain resistance. Background technique [0002] Fluorocarbon paint has been widely used in the fields of military industry, petrochemical, avionics, machinery, construction and household products due to its outstanding stain resistance, weather resistance, high heat resistance, high acid and alkali resistance and many other excellent properties. It has become an indispensable key material in many major engineering supporting projects in modern industry. [0003] Although organic fluorine resins and their coatings have many excellent properties, ...

Claims

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Application Information

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IPC IPC(8): C08G63/682C08G63/16C08G63/85
Inventor 王忠刚李文娟由继业孙良
Owner DALIAN UNIV OF TECH
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