CN111153839A - Sulfone-containing dihydric alcohol and preparation method thereof - Google Patents
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- C07C317/16—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C317/22—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
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Abstract
The invention relates to the technical field of organic compound process application, in particular to a sulfone-containing dihydric alcohol and a preparation method thereof. The invention provides a sulfone-containing diol which has a structure shown in a formula (I). The dihydric alcohol containing the sulfone group has high thermal stability and good radiation resistance, and the alcoholic hydroxyl group can be combined with various substances and have polymerization reaction, so that the sulfone group benzene ring conjugated structure is introduced into other compounds or polymers, and the defects of common amine and alcohol chain extenders are avoided. The sulfone-containing diol is used as a chain extender for synthesizing polyurethane, and the synthesized polyurethane has excellent mechanical property, heat resistance and aging resistance.
Description
Technical Field
The invention relates to the technical field of organic compound process application, in particular to a sulfone-containing dihydric alcohol and a preparation method thereof.
Background
Chain extenders adopted in traditional polyurethane synthesis can be divided into alcohol and amine chain extenders, and MOCA is largely used as the chain extender in the current industrial production. The chemical name of MOCA is 3,3 '-dichloro-4, 4' -diaminodiphenylmethane, which is the most popular aromatic diamine chain extender currently used, and the sales amount of MOCA always occupies absolute advantage. MOCA is mainly used as a chain extension curing agent of TDI based prepolymer, is widely applied to the mechanical industry, the automobile and airplane manufacturing industry, the mining industry, sports facilities and various light industry manufacturing industries, and can also be used as a cross-linking agent of PU coating and adhesive, a curing agent of epoxy resin, a high-electric-resistance product and the like. However, the MOCA chain-extended MDI-based prepolymer can obtain a polyurethane elastomer with high temperature resistance and high tearing resistance, but the chain extension curing reaction is too fast, and the reaction process is not easy to control, so that the MOCA chain-extended MDI-based prepolymer is generally not accepted by people. And the polyurethane elastomer prepared by using the alcohol chain extender, such as 1, 4-Butanediol (BDO), as the chain extender has no high temperature resistance and high tearing resistance compared with the polyurethane elastomer prepared by MOCA.
Disclosure of Invention
In view of the above, the technical problem to be solved by the present invention is to provide a sulfone-containing diol and a preparation method thereof, the sulfone-containing diol provided by the present invention can be used as a chain extender for synthesizing polyurethane, and the synthesized polyurethane has excellent mechanical properties and heat resistance.
The invention provides a sulfone-containing diol which has a structure shown in a formula (I):
the invention also provides a preparation method of the sulfone-containing dihydric alcohol, which comprises the following steps:
A) under the condition of protective gas, mixing 4, 4-dihydroxy diphenyl sulfone, an acid-binding agent and absolute ethyl alcohol, and heating to obtain a mixed solution;
B) mixing the mixed solution with 3-chloro-1-propanol, and reacting at 50-80 ℃ to obtain the sulfone-containing diol with the structure shown in the formula (I):
preferably, the ratio of the sum of the molar contents of the 4, 4-dihydroxy diphenyl sulfone and the acid binding agent to the amount of absolute ethyl alcohol is 0.1-0.5 mol: 150-200 mL.
Preferably, the molar ratio of the 4, 4-dihydroxy diphenyl sulfone to the acid-binding agent to the 3-chloro-1-propanol is 1: 2-6: 2 to 6.
Preferably, the acid-binding agent comprises one or more of potassium hydroxide, sodium hydroxide and potassium carbonate.
Preferably, the shielding gas is nitrogen.
Preferably, in step a), the temperature after heating is a reflux temperature.
Preferably, in the step B), the reaction time is 1-48 h.
Preferably, step B) further comprises, after the reaction is completed:
and (3) carrying out rotary evaporation on the obtained product solution, carrying out acid washing and water washing on the rotary evaporated product, and carrying out vacuum drying to obtain the sulfone-containing diol with the structure shown in the formula (I).
The invention provides a sulfone-containing diol which has a structure shown in a formula (I):
the dihydric alcohol containing the sulfone group has high thermal stability and good radiation resistance, and the alcoholic hydroxyl group can be combined with various substances and have polymerization reaction, so that the sulfone group benzene ring conjugated structure is introduced into other compounds or polymers, and the defects of common amine and alcohol chain extenders are avoided. The sulfone-containing diol is used as a chain extender for synthesizing polyurethane, and the synthesized polyurethane has excellent mechanical property, heat resistance and aging resistance.
Drawings
FIG. 1 is an infrared spectrum of a sulfone group-containing diol prepared in example 1 of the present invention;
FIG. 2 shows a process for preparing a sulfone group-containing diol prepared in example 1 of the present invention1H NMR spectrum.
Detailed Description
The technical solutions of the present invention will be described clearly and completely with reference to the following embodiments of the present invention, and it should be understood that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
The invention provides a sulfone-containing diol which has a structure shown in a formula (I):
the sulfone-containing dihydric alcohol (BHPPS) provided by the invention has high thermal stability and good radiation resistance, and alcoholic hydroxyl can be subjected to chemical combination and polymerization with various substances, so that a sulfone-containing benzene ring conjugated structure is introduced into other compounds or polymers, and the defects of common amine and alcohol chain extenders are avoided. The sulfone-containing diol is used as a chain extender for synthesizing polyurethane, and the synthesized polyurethane has excellent mechanical property, heat resistance and aging resistance.
The invention also provides a preparation method of the sulfone-containing diol, which comprises the following steps:
A) under the condition of protective gas, mixing 4, 4-dihydroxy diphenyl sulfone, an acid-binding agent and absolute ethyl alcohol, and heating to obtain a mixed solution;
B) mixing the mixed solution with 3-chloro-1-propanol, and reacting at 50-80 ℃ to obtain the sulfone-containing diol with the structure shown in the formula (I):
in the invention, 4-dihydroxy diphenyl sulfone (bisphenol S), an acid binding agent and absolute ethyl alcohol are mixed under the condition of protective gas, and a mixed solution is obtained after heating.
In certain embodiments of the invention, the shielding gas comprises nitrogen.
In certain embodiments of the invention, the acid scavenger comprises one or more of potassium hydroxide, sodium hydroxide, and potassium carbonate.
In some embodiments of the invention, the ratio of the sum of the molar contents of the 4, 4-dihydroxy diphenyl sulfone and the acid-binding agent to the amount of the absolute ethyl alcohol is 0.1-0.5 mol: 150-200 mL. In certain embodiments, the ratio of the sum of the molar contents of the 4, 4-dihydroxydiphenyl sulfone and the acid scavenger to the amount of absolute ethanol is 0.2 mol: 175mL or 0.12 mol: 150 mL.
In certain embodiments of the present invention, mixing 4, 4-dihydroxydiphenyl sulfone, an acid-binding agent, and absolute ethanol is mixing 4, 4-dihydroxydiphenyl sulfone, an acid-binding agent, and absolute ethanol with stirring. In some embodiments of the invention, the rotation speed of the stirring and mixing is 150 to 300 r/min. In certain embodiments, the rotational speed of the agitating mixing is 200r/min, 300r/min, or 150 r/min. In certain embodiments of the invention, the agitating mixing is performed in an agitator.
In certain embodiments of the invention, the heated temperature is the reflux temperature. The solid mixture was completely dissolved by heating to obtain a mixed solution.
And (3) after obtaining a mixed solution, mixing the mixed solution with 3-chloro-1-propanol, and reacting at 50-80 ℃ to obtain the sulfone-containing dihydric alcohol with the structure shown in the formula (I).
In certain embodiments of the invention, the molar ratio of 4, 4-dihydroxydiphenyl sulfone, acid scavenger, and 3-chloro-1-propanol is 1: 2-6: 2 to 6. In certain embodiments, the molar ratio of 4, 4-dihydroxydiphenyl sulfone, acid scavenger, and 3-chloro-1-propanol is 1: 4: 4. 1: 2: 4 or 1: 4: 2.
in the invention, the reaction temperature is 50-80 ℃, and in some embodiments of the invention, the reaction time is 1-48 h. In certain embodiments of the invention, the temperature of the reaction is 70 ℃, 50 ℃ or 80 ℃ and the time of the reaction is 24 hours or 12 hours.
In some embodiments of the present invention, after the reaction is completed, the method further comprises:
and (3) carrying out rotary evaporation on the obtained product solution, carrying out acid washing and water washing on the rotary evaporated product, and carrying out vacuum drying to obtain the sulfone-containing diol with the structure shown in the formula (I).
In certain embodiments of the invention, the product solution further comprises cooling prior to rotary evaporation. The cooling method is not particularly limited, and may be a cooling method known to those skilled in the art, and in some embodiments, the temperature after cooling is room temperature.
In some embodiments of the invention, the temperature of the rotary evaporation is 70-90 ℃, the rotation speed of the rotary evaporation is 20-40 r/min, and the rotary evaporation time is 10-20 min. In certain embodiments, the temperature of the rotary evaporation is 80 ℃, the rotation rate of the rotary evaporation is 30 revolutions/min, and the time of the rotary evaporation is 15 min. The rotary evaporation was used to remove ethanol.
In certain embodiments of the invention, the acid wash comprises:
mixing the rotary evaporated product with hydrochloric acid, and carrying out acid washing;
the pH value of the mixed liquid is 1-3.
In some embodiments of the invention, the pH of the mixed liquor after mixing is 3.
In some embodiments of the present invention, the number of acid washing is 2 to 4.
The acid wash is used to remove unreacted acid-binding agent, water soluble salts and 3-chloro-1-propanol.
In certain embodiments of the present invention, the water wash is a deionized water wash. In some embodiments of the present invention, the number of the water washing is 2 to 3.
The method and parameters of the vacuum drying are not particularly limited in the present invention, and those known to those skilled in the art can be used.
In the preparation method of the sulfone-containing dihydric alcohol, the applied solvent is less in dosage, the recovery rate is high, the cost is low, the product purity is higher, the generated three wastes are less, and the pollution degree is low.
The applicant creatively finds that the synthesized polyurethane has better mechanical property, heat resistance and aging resistance by taking the sulfone-containing diol as a chain extender of the synthesized polyurethane.
In order to further illustrate the present invention, the following examples are provided to describe in detail a sulfone group-containing diol and a preparation method thereof, but they should not be construed as limiting the scope of the present invention.
The starting materials used in the following examples are all generally commercially available.
Example 1
(1) In a 500mL three-necked flask, the molar ratio of bisphenol S to KOH was 1: 4, bisphenol S10g (0.04mol), KOH 8.96g (0.16mol) were added successively, followed by 175mL of absolute ethanol, the stirrer speed was set at 200r/min, and the mixture was heated to reflux until the solid mixture was completely dissolved.
(2) 15.12g of 3-chloro-1-propanol (0.16mol) were subsequently introduced into a three-necked flask and reacted at 70 ℃ for 24 hours.
(3) After the reaction is finished, stopping heating, cooling to room temperature, and carrying out rotary evaporation on the reaction mixed liquid at 80 ℃ for 15min at the rotary evaporation rate of 30 revolutions per minute. And then adding hydrochloric acid into the reaction system, adjusting the pH value to 3, washing for 3 times, then adding deionized water, washing for 2 times, and drying in vacuum to obtain the sulfone-containing diol BHPPS. The yield was 98%.
In the preparation method provided by the embodiment, the used solvent absolute ethyl alcohol is less in use amount, the recovery rate of the ethyl alcohol reaches 95%, and the product purity reaches 98%.
In this example, the obtained diol containing sulfone group was subjected to infrared analysis to obtain an infrared spectrum of the diol containing sulfone group, as shown in fig. 1. FIG. 1 shows a sulfone group-containing diol prepared in example 1 of the present inventionAnd the infrared spectrum of the raw material bisphenol S. As can be seen from FIG. 1, the hydroxyl absorption peak of the sulfone group-containing diol is significantly shifted to a high wavenumber region at 2950cm, as compared with that of the starting bisphenol S-1And 2880cm-1A methylene absorption peak appears at 1150cm-1new-SO appears2Symmetric absorption Peak, 1315cm-1new-SO appears2Asymmetric absorption peak, which indicates that we successfully synthesized the target product.
This example also performed NMR analysis on the resulting sulfone group-containing diol to obtain a sulfone group-containing diol1HNMR spectrum, as shown in FIG. 2. FIG. 2 shows a process for preparing a sulfone group-containing diol prepared in example 1 of the present invention1H NMR spectrum. As can be seen from FIG. 2, the double peaks appear at 7.825 and 7.10ppm, which are hydrogen atoms on the benzene ring, because the sulfone group has an electron-withdrawing effect, the wave number of the hydrogen atom absorption peak close to the sulfone group is increased, and the position of the hydrogen atom on the benzene ring is finally determined by calculating according to the number of the absorption peaks; similarly, the hydroxyl has an electron withdrawing effect, so that the wave number of a hydrogen atom absorption peak close to the hydroxyl is increased, calculation is performed according to the number of the absorption peaks, and finally the positions of the hydrogen atoms on the carbon chain and the hydroxyl are determined, and the result shows that all nuclear magnetic spectrum peaks have good attribution, which indicates that the BHPPS is successfully synthesized.
Example 2
The preparation method of the sulfone-containing dihydric alcohol BHPPS comprises the following steps:
(1) in a 500mL three-necked flask according to bisphenol S: the molar ratio of KOH is 1: 2, bisphenol S10g (0.04mol), KOH 4.48g (0.08mol) were added successively, 150mL of absolute ethanol was added, the stirring speed of the stirrer was set to 200r/min, and the mixture was heated to reflux until the solid mixture was completely dissolved.
(2) 15.12g of 3-chloro-1-propanol (0.16mol) were subsequently introduced into a three-necked flask and reacted at 70 ℃ for 24 hours.
(3) After the reaction is finished, stopping heating, cooling to room temperature, and carrying out rotary evaporation on the reaction mixed liquid at 80 ℃ for 15min at the rotary evaporation rate of 30 revolutions per minute. And then adding hydrochloric acid into the reaction system, adjusting the pH value to 3, washing for 3 times, then adding deionized water, washing for 2 times, and drying in vacuum to obtain the sulfone-containing diol BHPPS. The yield was 90%.
In the preparation method provided by the embodiment, the used solvent absolute ethyl alcohol is less in use amount, the recovery rate of the ethyl alcohol reaches 95%, and the product purity reaches 90%.
Example 3
The preparation method of the sulfone-containing dihydric alcohol BHPPS comprises the following steps:
(1) in a 500mL three-necked flask according to bisphenol S: the molar ratio of KOH is 1: 4, bisphenol S10g (0.04mol), KOH 8.96g (0.16mol) were added successively, followed by 175mL of absolute ethanol, the stirrer speed was set at 200r/min, and the mixture was heated to reflux until the solid mixture was completely dissolved.
(2) 7.56g of 3-chloro-1-propanol (0.08mol) were subsequently introduced into a three-necked flask and reacted at 70 ℃ for 24 hours.
(3) And after the reaction is finished, stopping heating, cooling to room temperature, carrying out rotary evaporation on the reaction mixed solution, and carrying out rotary evaporation on the reaction mixed solution at 80 ℃ for 15min at the rotary evaporation rate of 30 revolutions per minute. And then adding hydrochloric acid into the reaction system, adjusting the pH value to 3, washing for 3 times, then adding deionized water, washing for 2 times, and drying in vacuum to obtain the sulfone-containing diol BHPPS. The yield was 87%.
In the preparation method provided by the embodiment, the used solvent absolute ethyl alcohol is less in use amount, the recovery rate of the ethyl alcohol reaches 95%, and the product purity reaches 87%.
Example 4
The preparation method of the sulfone-containing dihydric alcohol BHPPS comprises the following steps:
(1) in a 500mL three-necked flask according to bisphenol S: the molar ratio of KOH is 1: 4, bisphenol S10g (0.04mol), KOH 8.96g (0.16mol) were added successively, followed by 175mL of absolute ethanol, the stirrer speed was set at 300r/min, and the mixture was heated to reflux until the solid mixture was completely dissolved.
(2) 15.12g of 3-chloro-1-propanol (0.16mol) were subsequently introduced into a three-necked flask and reacted at 50 ℃ for 24 hours.
(3) After the reaction is finished, stopping heating, cooling to room temperature, and carrying out rotary evaporation on the reaction mixed liquid at 80 ℃ for 15min at the rotary evaporation rate of 30 revolutions per minute. And then adding hydrochloric acid into the reaction system, adjusting the pH value to 3, washing for 3 times, then adding deionized water, washing for 2 times, and drying in vacuum to obtain the sulfone-containing diol BHPPS. The yield was 90%.
In the preparation method provided by the embodiment, the used solvent absolute ethyl alcohol is less in use amount, the recovery rate of the ethyl alcohol reaches 96%, and the product purity reaches 91%.
Example 5
The preparation method of the sulfone-containing dihydric alcohol BHPPS comprises the following steps:
(1) in a 500mL three-necked flask according to bisphenol S: the molar ratio of KOH is 1: 4, bisphenol S10g (0.04mol), KOH 8.96g (0.16mol) were added successively, followed by 175mL of absolute ethanol, the stirrer speed was set at 200r/min, and the mixture was heated to reflux until the solid mixture was completely dissolved.
(2) 15.12g of 3-chloro-1-propanol (0.16mol) were subsequently introduced into a three-necked flask and reacted at 80 ℃ for 24 hours.
(3) After the reaction is finished, stopping heating, cooling to room temperature, and carrying out rotary evaporation on the reaction mixed liquid at 80 ℃ for 15min at the rotary evaporation rate of 30 revolutions per minute. And then adding hydrochloric acid into the reaction system, adjusting the pH value to 3, washing for 3 times, then adding deionized water, washing for 2 times, and drying in vacuum to obtain the sulfone-containing diol BHPPS. The yield was 87%.
In the preparation method provided by the embodiment, the used solvent absolute ethyl alcohol is less in use amount, the recovery rate of the ethyl alcohol reaches 95%, and the product purity reaches 90%.
Example 6
The preparation method of the sulfone-containing dihydric alcohol BHPPS comprises the following steps:
(1) in a 500mL three-necked flask according to bisphenol S: the molar ratio of KOH is 1: 4, bisphenol S10g (0.04mol), KOH 8.96g (0.16mol) were added successively, followed by 175mL of absolute ethanol, the stirrer speed was set at 200r/min, and the mixture was heated to reflux until the solid mixture was completely dissolved.
(2) 15.12g of 3-chloro-1-propanol (0.16mol) were subsequently introduced into a three-necked flask and reacted at 80 ℃ for 12 hours.
(3) After the reaction is finished, stopping heating, cooling to room temperature, and carrying out rotary evaporation on the reaction mixed liquid at 80 ℃ for 15min at the rotary evaporation rate of 30 revolutions per minute. And then adding hydrochloric acid into the reaction system, adjusting the pH value to 3, washing for 3 times, then adding deionized water, washing for 2 times, and drying in vacuum to obtain the sulfone-containing diol BHPPS. The yield was 90%.
In the preparation method provided by the embodiment, the used solvent absolute ethyl alcohol is less in use amount, the recovery rate of the ethyl alcohol reaches 95%, and the product purity reaches 92%.
Example 7
The preparation method of the sulfone-containing dihydric alcohol BHPPS comprises the following steps:
(1) in a 500mL three-necked flask according to bisphenol S: the molar ratio of KOH is 1: 4, bisphenol S10g (0.04mol), KOH 8.96g (0.16mol) were added successively, followed by 175mL of absolute ethanol, the stirrer speed was set at 150r/min, and the mixture was heated to reflux until the solid mixture was completely dissolved.
(2) 15.12g of 3-chloro-1-propanol (0.16mol) were subsequently introduced into a three-necked flask and reacted at 70 ℃ for 48 h.
(3) After the reaction is finished, stopping heating, cooling to room temperature, and carrying out rotary evaporation on the reaction mixed liquid at 80 ℃ for 15min at the rotary evaporation rate of 30 revolutions per minute. And then adding hydrochloric acid into the reaction system, adjusting the pH value to 3, washing for 3 times, then adding deionized water, washing for 2 times, and drying in vacuum to obtain the sulfone-containing diol BHPPS. The yield was 93%.
In the preparation method provided by the embodiment, the used solvent absolute ethyl alcohol is less in use amount, the recovery rate of the ethyl alcohol reaches 95%, and the product purity reaches 93%.
Example 8
The chain extender BHPPS obtained in example 1, polytetrahydrofuran ether glycol (PTMG) and Toluene Diisocyanate (TDI) are prepared into the polyurethane elastomer by a one-step synthesis method, and the specific operation steps are as follows:
(1) dehydration treatment of diisocyanates
1.74g (0.01mol) of TDI was charged into a three-necked flask equipped with a mechanical stirrer, nitrogen blanket, constant pressure dropping funnel, heated in an oil bath and evacuated with a vacuum pump until dehydration was complete.
(2) Reaction process
Introducing nitrogen into a three-neck flask in advance, controlling the temperature in the three-neck flask to be 80 ℃, dropwise adding 5g of PTMG (0.005mol) into the three-neck flask by using a constant-pressure dropping funnel at the dropping speed of 3 drops/s, after the dropwise addition is finished, adding 9mL of toluene with the solid content of 49.20%, then slowly dropwise adding 0.45g of chain extender BDO (0.005mol), and reacting for 5 hours to obtain the target product.
(3) Subsequent treatment
The product is poured into distilled water with the temperature of 25 ℃ for soaking for 5h, filtered and crushed, boiled and washed respectively by distilled water and ethanol for 3 times, and dried in vacuum for 12h at the temperature of 60 ℃ to obtain 10.4g of refined off-white copolymer powder polyurethane, wherein the yield is 96%.
Then fixing other reaction raw materials and proportioning, only changing the chain extender, respectively preparing polyurethane taking BPO as the chain extender and polyurethane taking MOCA as the chain extender by the same synthesis method, and then testing the glass transition temperature (Tg), the mechanical property and the aging resistance of the three synthesized polyurethane elastomers, wherein the performance data are shown in Table 1:
TABLE 1 comparison of the Properties of polyurethanes made from BHPPS, BPO, MOCA, respectively
From Table 1, it can be found that the polyurethane elastomer obtained from BHPPS has a glass transition temperature (Tg) of 91.5 ℃ and an elastic modulus of 45.4 MPa; after being aged for 100 hours by a xenon lamp, the glass transition temperature (Tg) of the polyurethane elastomer is 90.7 ℃, and the elastic modulus is 44.9 MPa. The corresponding properties of polyurethane elastomers prepared by adopting BPO or MOCA are obviously poorer. Therefore, the sulfone-containing diol is used as a chain extender for synthesizing polyurethane, and the prepared polyurethane elastomer has good heat resistance, mechanical property and aging resistance.
The above description of the embodiments is only intended to facilitate the understanding of the method of the invention and its core idea. Various modifications to these embodiments will be readily apparent to those skilled in the art, and the generic principles defined herein may be applied to other embodiments without departing from the spirit or scope of the invention. Thus, the present invention is not intended to be limited to the embodiments shown herein but is to be accorded the widest scope consistent with the principles and novel features disclosed herein.
Claims (9)
1. A sulfone group-containing diol having a structure represented by the formula (I):
2. a preparation method of a sulfone group-containing diol comprises the following steps:
A) under the condition of protective gas, mixing 4, 4-dihydroxy diphenyl sulfone, an acid-binding agent and absolute ethyl alcohol, and heating to obtain a mixed solution;
B) mixing the mixed solution with 3-chloro-1-propanol, and reacting at 50-80 ℃ to obtain the sulfone-containing diol with the structure shown in the formula (I):
3. the preparation method according to claim 2, wherein the ratio of the sum of the molar contents of the 4, 4-dihydroxydiphenyl sulfone and the acid-binding agent to the amount of absolute ethanol is 0.1-0.5 mol: 150-200 mL.
4. The method according to claim 2, wherein the molar ratio of the 4, 4-dihydroxydiphenyl sulfone to the acid-binding agent to the 3-chloro-1-propanol is 1: 2-6: 2 to 6.
5. The preparation method of claim 2, wherein the acid-binding agent comprises one or more of potassium hydroxide, sodium hydroxide and potassium carbonate.
6. The method of claim 2, wherein the shielding gas is nitrogen.
7. The method according to claim 2, wherein the temperature after heating in step a) is a reflux temperature.
8. The preparation method according to claim 2, wherein in the step B), the reaction time is 1-48 h.
9. The method according to claim 2, wherein the step B) further comprises, after the reaction is completed:
and (3) carrying out rotary evaporation on the obtained product solution, carrying out acid washing and water washing on the rotary evaporated product, and carrying out vacuum drying to obtain the sulfone-containing diol with the structure shown in the formula (I).
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN115286770A (en) * | 2022-08-11 | 2022-11-04 | 国科广化(南雄)新材料研究院有限公司 | Curing agent based on phenol-urethane bond and preparation method and application thereof |
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| JPS5967258A (en) * | 1982-10-12 | 1984-04-16 | Nikka Chem Ind Co Ltd | Preparation of bis(4-hydroxyalkoxyphenyl)sulfone |
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| US3810938A (en) * | 1968-05-15 | 1974-05-14 | Espe Pharm Praep | Novel diacrylic and dimethacrylic acid esters |
| JPS5967258A (en) * | 1982-10-12 | 1984-04-16 | Nikka Chem Ind Co Ltd | Preparation of bis(4-hydroxyalkoxyphenyl)sulfone |
Non-Patent Citations (1)
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN115286770A (en) * | 2022-08-11 | 2022-11-04 | 国科广化(南雄)新材料研究院有限公司 | Curing agent based on phenol-urethane bond and preparation method and application thereof |
| CN115286770B (en) * | 2022-08-11 | 2024-01-09 | 国科广化(南雄)新材料研究院有限公司 | Curing agent based on phenol-carbamate bond, and preparation method and application thereof |
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Application publication date: 20200515 |