CN113512191A - Perfluoropolyether carboxylic acid compound and preparation method thereof - Google Patents
Perfluoropolyether carboxylic acid compound and preparation method thereof Download PDFInfo
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Abstract
The invention relates to the technical field of synthesis of high molecular compounds, and particularly relates to a perfluoropolyether carboxylic acid compound and a preparation method thereof. A method for preparing a perfluoropolyether carboxylic acid compound, comprising the steps of: (1): completely dissolving perfluoropolyether alcohol in a solvent; (2): adding cyclic anhydride and a catalyst, heating to 40-80 ℃, performing reflux reaction for 2-5h, and washing with water; (3): carrying out reduced pressure distillation to obtain a perfluoropolyether carboxylic acid compound; the solvent is a fluorine-containing solvent capable of dissolving perfluoropolyether. The preparation method of the perfluoropolyether carboxylic acid compound has short synthetic route and does not generate strong irritant solvent and metal salt. A perfluoropolyether carboxylic acid compound has high purity, can generate alcoholysis and aminolysis to generate corresponding derivatives such as ester and amide, can further prepare compounds such as perfluoropolyether siloxane, and is an intermediate with wide application.
Description
Technical Field
The invention relates to the technical field of synthesis of high molecular compounds, and particularly relates to a perfluoropolyether carboxylic acid compound and a preparation method thereof.
Background
The perfluoropolyether is a colorless transparent oily substance, and the main chain of the perfluoropolyether is formed by-CF2-O-CF2Such ether chain constituents, have excellent flexibility, heat resistance, chemical stability and non-flammability, and such materials are very safe. The perfluoropolyether fingerprint-resistant technology is mainly characterized in that siloxane active groups are introduced at the tail ends of perfluoropolyether chains, and the siloxane is hydrolyzed and then is subjected to dehydration condensation with silicon hydroxyl groups on the surface of a substrate to form firm-Si-O-Si-bonds, so that a layer of perfluoropolyether coating is introduced on the surface of the substrate, and the substrate is endowed with excellent water resistance, oil resistance, antifouling property, wear resistance and anti-fingerprint propertyScratch resistance, and further achieve the purpose of fingerprint resistance.
However, due to the special nature of perfluoropolyether chains, it is not easy to introduce siloxane reactive groups at their ends by chemical reaction. the-COOH at the tail end of the perfluoropolyether carboxylic acid has higher reaction activity, the formed carboxylate can be used as a perfluoropolyether surfactant, the perfluoropolyether carboxylic acid can be further prepared into perfluoropolyether methyl ester and perfluoropolyether acyl chloride (or acyl fluoride), and the perfluoropolyether methyl ester and the perfluoropolyether acyl chloride (or acyl fluoride) are important intermediates of perfluoropolyether polyurethane, perfluoropolyether acrylic monomers and anti-fingerprint agents.
The perfluoropolyether polyurethane synthesized in patent CN101146840B from 3M company can be used as a hard coating additive, and can also be directly used as a protective coating to be applied to various mobile and non-mobile information display products, including mobile phones, LCD televisions, touch screens, automobile navigation systems and the like. Chinese patent CN104876823A adopts perfluoropolyether acyl fluoride to react with allyl alcohol to prepare perfluoropolyether allyl compound with double bonds, can be used as monomers for solution polymerization, emulsion polymerization and photoinitiated polymerization, and is suitable for the field of coatings. A novel perfluoropolyether amido siloxane anti-fingerprint agent is proposed in great golden patent CN106661436A, and the anti-fingerprint agent synthesized by adopting perfluoropolyether acyl fluoride has better friction resistance. Chinese patent CN109071793A discloses a method for synthesizing an anti-fingerprint agent, which uses perfluoropolyether alcohol to prepare the anti-fingerprint agent through substitution esterification, high temperature hydrolysis and amidation reactions, wherein the steel wool and rubber friction resistance of the product respectively reaches 20000 times and 8000 times, the product performance is good, but the route for preparing perfluoropolyether carboxylic acid is complicated, and specifically, strong base is needed to be used for many times in the reaction, such as: the potassium salt formed by sodium hydroxide and potassium hydroxide is difficult to completely remove in the post-treatment process, and the temperature in the hydrolysis process is higher (above 100 ℃), so that the method has certain danger. Tetrahydrofuran and glycol dimethyl ether with large pungent smell are needed to be used in the synthesis process, which causes discomfort to experimenters.
Disclosure of Invention
In order to overcome the defects and shortcomings in the prior art, the invention aims to provide a perfluoropolyether carboxylic acid compound and a preparation method thereof, the preparation method of the perfluoropolyether carboxylic acid compound is short in synthetic route and free from generation of strong irritant solvents and metal salts, and the invention aims to provide a perfluoropolyether carboxylic acid compound which is high in purity, can generate alcoholysis and aminolysis to generate corresponding derivatives such as esters and amides, can further prepare compounds such as perfluoropolyether siloxane and is an intermediate with wide application.
The purpose of the invention is realized by the following technical scheme:
a method for preparing a perfluoropolyether carboxylic acid compound, comprising the steps of:
(1): completely dissolving perfluoropolyether alcohol in a solvent;
(2): adding cyclic anhydride and a catalyst, heating to 40-80 ℃, performing reflux reaction for 2-5h, and washing with water;
(3): carrying out reduced pressure distillation to obtain a perfluoropolyether carboxylic acid compound;
the solvent is a fluorine-containing solvent capable of dissolving perfluoropolyether.
Preferably, the solvent is one or more of m-ditrifluorotoluene, methyl nonafluorobutyl ether, ethyl nonafluorobutyl ether, trifluorotrichloromethane, perfluorohexane and trimeric hexafluoropropene.
Preferably, the cyclic anhydride is an internal anhydride having three or more membered rings.
Preferably, the cyclic anhydride is one or more of succinic anhydride, maleic anhydride or glutaric anhydride.
Preferably, the cyclic anhydride is a mixture of succinic anhydride and glutaric anhydride in a molar ratio of 1: 1-2.
Preferably, the amount of the cyclic anhydride added is 1.05 to 8 times the molar amount of the perfluoropolyether alcohol.
Preferably, the amount of the cyclic anhydride added is 1.5 to 3 times the molar amount of the perfluoropolyether alcohol.
Preferably, the catalyst is an organic base compound.
Preferably, the catalyst is one of dimethylaminopyridine, dicyclohexylcarbodiimide or N, N-diisopropylethylamine.
Preferably, the catalyst is a mixture of dimethylaminopyridine and N, N-diisopropylethylamine in a molar ratio of 1: 1.
Preferably, the catalyst is used in an amount of 0.05 wt% to 10 wt% of the perfluoropolyether alcohol.
Preferably, the catalyst is used in an amount of 0.5 wt% to 2 wt% of the perfluoropolyether alcohol.
The structural formula of the perfluoropolyether carboxylic acid compound is shown as follows,
wherein Rf is F- (CF)2)m-(OC4F8)n-(OC3F6)s-(OC2F4)p-(OCF2)q-O(CF2)uWhere n, s, p and q are each an integer of 0 or more and 100 or less, the sum of n, s, p and q is at least 1, and the order of the presence of the respective repeating units, bracketed by brackets, with m, n, s, p and q is arbitrary in the formula: m and u are each an integer of 0 to 20 inclusive; x1Is a fluorine-containing or non-fluorine-containing alkyl group, X2Is a fluorine-containing or non-fluorine-containing alkyl group, or an alkyl group with N, O, S heteroatoms.
Wherein the repeating unit-OC3F6Is OCF2CF2CF2-or-OCF (CF)3)CF2-。
Preferably, X1is-CH2-、-CHCH3-、-(CH2)2-、-(CH2)3-、-(CH2)4-、-(CH2)5、-CHF-、-CFCH3-、-(CHF)2-or- (CHF)3-。
Preferably, X2is-CH2-、-CHCH3-、-(CH2)2-、-CH2-NH-、-CH2-O-CH2-、-CH2-S-CH2-、-(CH2)3-、
-CH＝CH-、-(CH2)4-、-(CH2)5-、-CH2C6H4-or a group in which the H atom of the above group is incompletely substituted with F.
Preferably, wherein Rf is preferably represented by the following formula (a), (b), (c) or (d),
(a)CF3-(OC2F4)p-(OCF2)q-OCF2-, wherein the sum of p and q is an integer of 10 or more and 200 or less;
(b)F-(CF2)3-(OCF(CF3)CF2)s-OCF(CF3) -, wherein s is an integer of 10 to 200;
(c)CF3-(OCF(CF3)CF2)s-(OCF2)q-OCF2-, wherein the sum of s and q is an integer of 10 or more and 200 or less;
(d)F-(CF2)3-(OCF2CF2CF2)s-O(CF2)2in the formula, s is an integer of 10 to 200.
The invention has the beneficial effects that:
1. the perfluoropolyether alcohol and the cyclic anhydride are selected to react in one step to obtain the perfluoropolyether carboxylic acid compound, so that the loss caused by multi-step reaction is avoided, and the reaction yield is high; meanwhile, the reaction time can be shortened, and the production efficiency can be improved.
2. The used anhydride reagent is solid, is convenient to store, has low price, lower toxicity and mild reaction conditions, can save the cost of the reagent, is safe and reliable, and is suitable for industrial production.
3. The perfluoropolyether alcohol is reacted in one step to obtain the perfluoropolyether carboxylic acid compound, so that the metal inorganic salt introduced by high-temperature hydrolysis of esters can be avoided.
4. The post-treatment of carboxylic acid only uses water washing, and is safe and environment-friendly.
Drawings
FIG. 1 shows a perfluoropolyether carboxylic acid compound (A) synthesized in example 1 of the present invention1) Nuclear magnetic resonance spectrogram;
FIG. 2 shows the perfluoropolyether carboxylic acid compound (A) synthesized in example 2 of this invention2) Nuclear magnetic resonance spectrogram;
FIG. 3 shows the perfluoropolyether carboxylic acid compound (A) synthesized in example 3 of this invention3) Nuclear magnetic resonance spectrogram;
FIG. 4 shows the perfluoropolyether carboxylic acid compound (A) synthesized in example 4 of this invention4) Nuclear magnetic resonance spectrogram;
FIG. 5 shows a perfluoropolyether ester-based compound (B) synthesized in comparative example 1 of the present invention1) Nuclear magnetic resonance spectrogram;
FIG. 6 shows a perfluoropolyether carboxylic acid compound (B) synthesized in comparative example 1 of the present invention2) Nuclear magnetic resonance spectrogram;
FIG. 7 shows a perfluoropolyether siloxane compound (Y) synthesized in application example 1 of the present invention1) Nuclear magnetic resonance spectrogram;
FIG. 8 is a nuclear magnetic resonance spectrum of impurities in trifluorotrichloroethane as a nuclear magnetic sample feeding solvent.
Detailed Description
The present invention will be further described with reference to the following examples for facilitating understanding of those skilled in the art, and the description of the embodiments is not intended to limit the present invention.
Example 1
A100 mL three-necked flask equipped with a stirrer was charged with 10g (2.86mmol) of a compound having an average composition of CF3(OCF2CF2)p(OCF2)qOCF2CH2OH perfluoropolyether alcohol (p and q sum is 36, number average molecular weight is 3500, produced by SOLVAY company), 15mL m-ditrifluorotoluene, 0.43g (4.29mmol, 1.5equ) succinic anhydride, 0.05g (0.5 wt% in perfluoropolyether alcohol) dimethylaminopyridine, heating to 40 ℃, stirring for reaction for 5h, extracting with water and distilling under reduced pressure to obtain 10.08g of colorless transparent product, wherein the yield is 98%, and the product is the perfluoropolyether carboxylic acid compound (A)1)CF3(OCF2CF2)p(OCF2)qOCF2CH2OCOCH2CH2COOH, reaction formula as follows.
Wherein Rf is CF3(OCF2CF2)p(OCF2)qOCF2-。
Example 2
A100 mL three-necked flask equipped with a stirrer was charged with 10g (2.03mmol) of a compound having an average composition of CF3(OCF2CF2)p(OCF2)qOCF2CH2OH perfluoropolyether alcohol (p and q sum is 49, number average molecular weight is 4930, produced by SOLVAY company), 15mL m-ditrifluorotoluene, 0.69g (6.09mmol, 3equ) glutaric anhydride, 0.2g (2 wt% in perfluoropolyether alcohol) N, N-diisopropylethylamine, heating to 60 ℃, refluxing and stirring for reaction for 4h, extracting with water and distilling under reduced pressure to obtain colorless transparent product 10.03g, yield 98%, namely perfluoropolyether carboxylic acid compound (A)2)CF3(OCF2CF2)p(OCF2)qOCF2CH2OCOCH2CH2CH2COOH, reaction formula as follows.
Wherein Rf is CF3(OCF2CF2)p(OCF2)qOCF2-。
Example 3
A100 mL three-necked flask equipped with a stirrer was charged with 10g (2.86mmol) of a compound having an average composition of CF3(OCF2CF2)p(OCF2)qOCF2CH2OH perfluoropolyether alcohol (p and q sum is 36, number average molecular weight is 3500, produced by SOLVAY company), 25mL m-ditrifluorotoluene, 2.12g (14.29mmol, 5equ) phthalic anhydride, 0.5g (5 wt% in perfluoropolyether alcohol) dimethylaminopyridine, heating to 80 ℃, stirring for reaction for 3h, extracting with water and distilling under reduced pressure to obtain 10.18g colorless transparent product with yield of 99%, namely perfluoropolyether carboxylic acid compound (A)3)，CF3(OCF2CF2)p(OCF2)qOCF2CH2OCOC6H4COOH, reaction formula as follows.
Wherein Rf is CF3(OCF2CF2)p(OCF2)qOCF2-
Example 4
A100 mL three-necked flask equipped with a stirrer was charged with 10g (2.24mmol) of a compound having an average composition of CF3CF2CF2(OCF(CF3)CF2)sOCF(CF3)CH2OH perfluoropolyether alcohol (s is 25, the number average molecular weight is 4460, the product is produced by Suzhou Binmu New Material Co., Ltd.), 15mL of m-ditrifluorotoluene, 1.79g (17.94mmol, 8equ) of succinic anhydride, 1.00g (10 wt% in perfluoropolyether alcohol) of N, N-diisopropylethylamine, the temperature is increased to 50 ℃, stirring reaction is carried out for 2 hours, colorless transparent products are obtained by water extraction and reduced pressure distillation, the yield is 97%, and the product is the perfluoropolyether carboxylic acid compound (A)4)，CF3CF2CF2(OCF(CF3)CF2)sOCF(CF3)CH2OCOCH2CH2COOH, reaction formula as follows.
Wherein Rf is CF3CF2CF2(OCF(CF3)CF2)sOCF(CF3)-
Comparative example 1
Reference is made to the method for synthesizing perfluoropolyether carboxylic acid in patent CN109071793A, and the specific experiment is as follows
Step 1:
a100 mL three-necked flask equipped with a stirrer was charged with 10g (2.86mmol) of a compound having an average composition of CF3(OCF2CF2)p(OCF2)qOCF2CH2OH perfluoropolyether alcohol (p and q sum is 36, number average molecular weight is 3500, produced by SOLVAY company), 15mL m-ditrifluoromethylene, 5mL ethylene glycol dimethyl ether and 2.6g of 50% potassium hydroxide solution are stirred for 3h at room temperature, then 3.8mL t-butyl bromoacetate and 0.42g tetrabutylammonium bromide are sequentially added into a reaction bottle, the mixture is stirred for 5h at 50 ℃, and colorless transparent products 9.6g are obtained by water extraction and reduced pressure distillation, the yield is 93%, namely the perfluoropolyether ester group compound (B)1)，CF3(OCF2CF2)p(OCF2)qOCF2CH2OCH2COOC4H9The reaction formula is as follows.
Wherein Rf is CF3(OCF2CF2)p(OCF2)qOCF2-
Step 2:
into a 100mL three-necked round-bottomed flask equipped with a thermometer and a stirrer were charged 9.6g of the perfluoropolyether ester-based compound (B) obtained in step 11) 17g of a 10% by weight potassium hydroxide solution, and stirring at 100 ℃ for 3 hours. After the temperature was lowered to room temperature, 10mL of tetrahydrofuran was added and the mixture was acidified with 2N hydrochloric acid, 30mL of hydrofluoroether HIE-7200 (manufactured by 3M Co.) was added and the mixture was stirred. The non-fluorinated phase (i.e., the upper layer solution) was removed, the fluorinated phase was washed 2 times with 2N hydrochloric acid, and finally distilled under reduced pressure to give 9.0g of a colorless transparent product in a yield of 95% (total yield of step 1 and step 2: 88.4%), which was the perfluoropolyether carboxylic acid compound (B)2)，CF3(OCF2CF2)p(OCF2)qOCF2CH2OCH2COOH, reaction formula as follows.
Wherein Rf is CF3(OCF2CF2)p(OCF2)qOCF2-。
Application example 1
Example 1 result A1The synthesis of the perfluoropolyether group-containing siloxane Compound Y can be carried out according to the following procedure1:CF3(OCF2CF2)p(OCF2)qOCF2CH2OCOCH2CH2 CON[(CH2)3Si(OCH3)3]2。
Into a 100mL four-necked round-bottomed flask equipped with a dropping funnel, a thermometer and a stirrer were charged 9.0g of the perfluoropolyether carboxylic acid compound (A) obtained in example 11) And 15mL of m-ditrifluorotoluene were sufficiently dissolved, and 0.32mL of oxalyl chloride and 0.10mL of DMF were dissolved in 5mL of m-ditrifluorotoluene, and the mixture was slowly dropped from the dropping funnel, and then heated to 50 ℃ to stir for 4 hours, and then dropped to room temperature to the room temperature, and then dropped slowly into a 250mL three-necked round bottom flask containing 10mL of m-ditrifluoromethyltoluene, 1.3mL of diisopropylethylamine and 2.2mL of bis (3-trimethoxysilylpropyl) amine, and stirred at room temperature for 5 hours. Adding 30mL of perfluorohexane, extracting with 50mL of methanol three times, distilling the fluorine phase under reduced pressure to remove volatile components to obtain colorless to pale yellow product, i.e., perfluoropolyether siloxane compound (Y) having trimethoxysilane at the end1)，CF3(OCF2CF2)p(OCF2)qOCF2CH2OCH2CON[(CH2)3Si(OCH3)3]2。
A obtained in the above example1，A2，A3And A4Both alcoholysis and aminolysis can occur to generate corresponding derivatives such as ester and amide. Perfluoropolyether siloxane Compound Y obtained in application example 11Can be used as a surface treating agent, such as an anti-fingerprint agent applied to mobile phone screens, glass panels, flat panel displays, automobile central screens and the like. As can be seen from the above examples and application examples, the perfluoropolyether carboxylic acid compound of the present invention is easy to prepare, and can further prepare compounds such as perfluoropolyether siloxanes, and is an intermediate having a wide range of uses.
From the comparison of examples 1 to 4 with comparative example 1, it can be seen that the production method of the perfluoropolyether carboxylic acid compound of the present invention, compared with the production method of comparative example 1: the reaction route and the reaction time are shorter, and the production efficiency can be improved; the adopted anhydride reagent has low price, and the cost can be reduced; the reaction temperature is relatively low, only water is used for extraction in the post-treatment process, and no additional organic solvent is used, so that the method is safe and environment-friendly; the yield of perfluoropolyether carboxylic acid synthesized from perfluoropolyether alcohols is significantly higher because, on the one hand, the reaction route is short, and, on the other hand, no organic solvent is used for the post-treatment, reducing the product dissolution loss.
The above-described embodiments are preferred implementations of the present invention, and the present invention may be implemented in other ways without departing from the spirit of the present invention.
Claims (10)
1. A process for producing a perfluoropolyether carboxylic acid compound, characterized by: the method comprises the following steps:
(1): completely dissolving perfluoropolyether alcohol in a solvent;
(2): adding cyclic anhydride and a catalyst, heating to 40-80 ℃, performing reflux reaction for 2-5h, and washing with water;
(3): carrying out reduced pressure distillation to obtain a perfluoropolyether carboxylic acid compound;
the solvent is a fluorine-containing solvent capable of dissolving perfluoropolyether.
2. The process according to claim 1, wherein: the solvent is one or more of m-ditrifluorotoluene, methyl nonafluorobutyl ether, ethyl nonafluorobutyl ether, trifluorotrichloromethane, perfluorohexane and trimeric hexafluoropropylene.
3. The process according to claim 1, wherein: the cyclic anhydride is an internal anhydride with more than three membered rings.
4. The process according to claim 3, wherein: the cyclic anhydride is one or a mixture of succinic anhydride, maleic anhydride or glutaric anhydride.
5. The process according to claim 4, wherein: the amount of the cyclic acid anhydride added is 1.05 to 8 times the molar amount of the perfluoropolyether alcohol.
6. The process according to claim 1, wherein: the catalyst is an organic alkali compound.
7. The process according to claim 6, wherein: the catalyst is one of dimethylaminopyridine, dicyclohexylcarbodiimide or N, N-diisopropylethylamine.
8. The process according to claim 7, wherein: the amount of the catalyst is 0.05 wt% -10 wt% of the perfluoropolyether alcohol.
9. The perfluoropolyether carboxylic acid compound produced by the production method according to claims 1 to 8, characterized in that: the structural formula of the compound is shown as follows,
wherein Rf is F- (CF)2)m-(OC4F8)n-(OC3F6)s-(OC2F4)p-(OCF2)q-O(CF2)uWhere n, s, p and q are each an integer of 0 or more and 100 or less, the sum of n, s, p and q is at least 1, and the order of the presence of the respective repeating units, bracketed by brackets, with m, n, s, p and q is arbitrary in the formula: m and u are each an integer of 0 to 20 inclusive; x1Is a fluorine-containing or non-fluorine-containing alkyl group, X2Is a fluorine-containing or non-fluorine-containing alkyl group, or an alkyl group with N, O, S heteroatoms.
10. A perfluoropolyether carboxylic acid compound according to claim 9, characterized in that: wherein Rf is preferably represented by the following formula (a), (b), (c) or (d),
(a)CF3-(OC2F4)p-(OCF2)q-OCF2-, wherein the sum of p and q is an integer of 10 or more and 200 or less;
(b)F-(CF2)3-(OCF(CF3)CF2)s-OCF(CF3) -, wherein s is an integer of 10 to 200;
(c)CF3-(OCF(CF3)CF2)s-(OCF2)q-OCF2-, wherein the sum of s and q is an integer of 10 or more and 200 or less;
(d)F-(CF2)3-(OCF2CF2CF2)s-O(CF2)2in the formula, s is an integer of 10 to 200.
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