CN116444783A - Polyether amine ethyl sodium sulfonate, preparation method and application thereof - Google Patents

Polyether amine ethyl sodium sulfonate, preparation method and application thereof Download PDF

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Publication number
CN116444783A
CN116444783A CN202310394263.4A CN202310394263A CN116444783A CN 116444783 A CN116444783 A CN 116444783A CN 202310394263 A CN202310394263 A CN 202310394263A CN 116444783 A CN116444783 A CN 116444783A
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sodium
polyetheramine
polyether amine
reaction
preparation
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Inventor
王峤
胡展
孙中平
乔小飞
邵江
贾海兵
何东荣
吕成戈
秦永涛
隋宝华
邵仁龙
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Wanhua Chemical Group Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32—Polymers modified by chemical after-treatment
    • C08G65/329—Polymers modified by chemical after-treatment with organic compounds
    • C08G65/334—Polymers modified by chemical after-treatment with organic compounds containing sulfur
    • C08G65/3344—Polymers modified by chemical after-treatment with organic compounds containing sulfur containing oxygen in addition to sulfur
    • C08G65/3346—Polymers modified by chemical after-treatment with organic compounds containing sulfur containing oxygen in addition to sulfur having sulfur bound to carbon and oxygen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/50—Polyethers having heteroatoms other than oxygen
    • C08G18/5072—Polyethers having heteroatoms other than oxygen containing sulfur
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/52—Natural or synthetic resins or their salts

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention provides polyether amine ethyl sodium sulfonate which has a structure shown in a formula (I). The invention also provides a preparation method and application of the polyether amine ethyl sodium sulfonate. The polyether amine ethyl sodium sulfonate provided by the invention has a novel structure, can be used as a chain extender and a surfactant of aqueous polyurethane dispersoid, has a simple and convenient preparation process, does not need to use high-toxicity and high-risk raw materials, is environment-friendly and strong in operability, and has a simple and convenient post-treatment process. The polyether amine ethyl sodium sulfonate provided by the invention has various functions, is safe and simple to manufacture, is suitable for industrial production, and is beneficial to improving the preparation and application of the aqueous polyurethane, so that the polyether amine ethyl sodium sulfonate has very important economic and social values, and NaO 3 SCH 2 CH 2 NH‑(CH 2 ‑CH 2 ‑O‑) n ‑CH 2 ‑CH 2 ‑NH 2 Formula (I).

Description

Polyether amine ethyl sodium sulfonate, preparation method and application thereof
Technical Field
The invention relates to the field of fine chemicals, in particular to polyether amine ethyl sodium sulfonate, a preparation method and application thereof.
Background
The chain extender used for synthesizing the waterborne polyurethane is mainly a hydrophilic chain extender, and the structure of the chain extender can influence the bonding strength of the waterborne polyurethane, so that the chain extender has very important effect in the preparation process of the waterborne polyurethane. Hydrophilic chain extenders, that is, chain extenders containing hydrophilic groups, wherein hydrophilic chain extenders containing anions mainly include carboxylic acid type chain extenders and sulfonic acid type chain extenders.
The ethylenediamine sodium ethanesulfonate belongs to a sulfonic acid type chain extender, has excellent hydrophilicity, can be used for preparing waterborne polyurethane as the hydrophilic chain extender, and is suitable for industries such as paint, printing ink, adhesive, leather finishing agent and the like. Polyurethane dispersion prepared by using ethylenediamine sodium ethanesulfonate has good hydrolytic stability and good compatibility with other anionic or nonionic aqueous dispersion. However, sodium ethylenediamine-based ethanesulfonate has little effect of surface activity.
Chinese patent CN 107935892a discloses a process for preparing sodium ethylenediamine-based ethanesulfonate, which comprises the steps of: and (3) performing Mannich reaction on taurine, nitromethane and formaldehyde to generate N- (2-nitroethyl) taurine, and then performing alkali neutralization and hydrogenation on the N- (2-nitroethyl) taurine to obtain sodium ethylenediamine ethanesulfonate. The reaction uses flammable and explosive raw materials such as nitromethane and the like, has high risk and has more process steps. Chinese patent CN 106187829a discloses a method for preparing ethylenediamine ethanesulfonate, which uses hydroxy acetonitrile and taurine as raw materials, or uses hydroxy acetonitrile, taurine and alkali metal hydroxide as raw materials, and prepares cyanoethyl taurine through dehydration condensation reaction; then hydrogenation is carried out under the action of a hydrogenation catalyst to prepare ethylenediamine-based ethanesulfonate hydrogenation liquid; and removing the solvent to obtain the product ethylenediamine ethanesulfonate. The material hydroxy acetonitrile used in the method has higher toxicity, so the reaction risk is higher.
Thus, although sodium ethylenediamine-based ethanesulfonate has been found to have good effects with respect to the sulfonic acid-type chain extender, it is limited by the preparation process thereof, and thus, more novel sulfonic acid-type chain extenders have been required to be developed to better meet the production requirements of aqueous polyurethane.
Disclosure of Invention
In order to make up the defects in the prior art, the invention aims to provide polyether amine ethyl sodium sulfonate which can be used as a novel sulfonic acid type chain extender for synthesizing aqueous polyurethane, has good surface activity and can be used as a novel surfactant.
Another object of the invention is to provide a process for the preparation and use of said sodium polyetheraminoethylsulfonate.
In a first aspect, the present invention provides a sodium polyetheraminoethyl sulfonate having the structure of formula (I):
NaO 3 SCH 2 CH 2 NH-(CH 2 -CH 2 -O-) n -CH 2 -CH 2 -NH 2
(I)
Wherein n represents 5 to 50.
The polyether amine ethyl sodium sulfonate provided by the invention contains amino and imino in the molecular chain, has the capability of reacting with active substances such as isocyanate and the like, and has the reactivity equivalent to that of common sulfonic acid type chain extender sodium ethylenediamine ethyl sulfonate, so that the polyether amine ethyl sodium sulfonate can be used as a chain extender of aqueous polyurethane dispersion. Compared with the sodium ethylenediamine ethanesulfonate with the defects of high raw material risk, long preparation flow and the like, the polyether amine ethanesulfonate provided by the invention has the advantages of abundant raw material sources, good safety, simple preparation process and suitability for large-scale industrial production.
In addition, the polyether amine ethyl sulfonate provided by the invention can be used as a novel surfactant, and has excellent hydrophilicity due to the sulfonate group contained in the molecular structure, and meanwhile, the organic chain segment is amphiphilic, so that compared with the conventional polyether surfactant (such as polysorbate-80), the polyether amine ethyl sulfonate provided by the invention has better surface activity and is more suitable for dispersing an O/W emulsion system.
In some preferred embodiments, n in formula (i) may represent 5 to 30, including 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30. In some more preferred embodiments, n in formula (I) may represent from 5 to 20. In some further preferred embodiments, n in formula (I) may represent 6 to 15.
The second aspect of the invention provides a preparation method of the polyether amine ethyl sulfonate according to any one of the technical schemes, which comprises the following steps: reacting polyetheramine with a structure shown as a formula (I') with sodium isethionate in the presence of water as a catalyst to obtain sodium polyetheramine isethionate;
NH 2 -(CH 2 -CH 2 -O-) n -CH 2 -CH 2 -NH 2
(I')
Wherein n is as defined in any one of the above technical schemes.
The chemical reaction equation of the preparation method provided by the invention is as follows:
H 2 N-(CH 2 -CH 2 -O-) n -CH 2 -CH 2 -NH 2 +HOCH 2 CH 2 SO 3 Na
→NaO 3 SCH 2 CH 2 NH-(CH 2 -CH 2 -O-) n -CH 2 -CH 2 -NH 2 +H 2 O
wherein n is as defined in any one of the above technical schemes.
In some preferred embodiments, the polyetheramine may be one or both of a propylpolyetheramine, a Ding Jumi amine. In some more preferred embodiments, the polyetheramine may be one or both of polyetheramines D400, D2000. In some further preferred embodiments, the polyetheramine may be polyetheramine D400.
In some preferred embodiments, the molar ratio of the polyetheramine to the sodium isethionate may be from 1.05 to 10:1, including but not limited to about 1.05:1, about 1.1:1, about 1.2:1, about 1.5:1, about 1.8:1, about 2:1, about 2.2:1, about 2.5:1, about 2.8:1, about 3:1, about 3.2:1, about 3.5:1, about 4:1, about 4.5:1, about 5:1, about 6:1, about 7:1, about 8:1, about 9:1, about 10:1 equimolar ratio, or any molar ratio interval. In some more preferred embodiments, the molar ratio of the polyetheramine to the sodium isethionate may be 1.1 to 3.5:1. In some further preferred embodiments, the molar ratio of the polyetheramine to the sodium isethionate may be 1.1 to 1.5:1. The proper excess of polyetheramine can improve the selectivity of polyetheramine sodium ethylsulfonate (i.e. monosubstituted), and avoid the formation of a large amount of disubstituted byproducts (i.e. NaO) 3 SCH 2 CH 2 NH-(CH 2 -CH 2 -O-) n -CH 2 -CH 2 -NHCH 2 CH 2 SO 3 Na)。
In some preferred embodiments, the catalyst (i.e., water) may be used in an amount of 0.1 to 30wt.% of the polyetheramine, including, but not limited to, about 0.1wt.%, about 0.5wt.%, about 1wt.%, about 2wt.%, about 5wt.%, about 8wt.%, about 10wt.%, about 12wt.%, about 15wt.%, about 18wt.%, about 20wt.%, about 22wt.%, about 28wt.%, about 30wt.%, etc., or any weight percentage interval. In some more preferred embodiments, the catalyst may be used in an amount of 0.5 to 20wt.% of the polyetheramine. In some further preferred embodiments, the catalyst may be used in an amount of 1 to 10wt.% of the polyetheramine.
In some preferred embodiments, the reaction temperature of the reaction may be 150 to 350 ℃. In some more preferred embodiments, the reaction temperature of the reaction may be 160 to 300 ℃. In some further preferred embodiments, the reaction temperature of the reaction may be 170 to 250 ℃.
In some preferred embodiments, the reaction time of the reaction may be 0.1 to 10 hours. In some more preferred embodiments, the reaction time of the reaction may be 0.2 to 5 hours. In some further preferred embodiments, the reaction time of the reaction may be 0.3 to 1 hour.
The preparation method provided by the invention can further comprise the following steps: after the reaction is finished, the obtained reactant is injected into water, filter aid is added and filtration is carried out, so that the aqueous solution of polyether amine sodium ethyl sulfonate with the concentration of 20-60 wt.% is obtained. The preparation method provided by the invention is characterized in that reactants obtained by reaction are injected into water, and the unreacted polyether amine raw material and a small amount of di-substituent byproducts can be removed only by filtration by utilizing the principle that the polyether amine sodium ethylsulfonate product is dissolved in water and the water solubility of macromolecular polyether amine is lower, so that a product solution with higher purity is obtained.
In some preferred embodiments, the mass ratio of water to the reaction product may be from 0.2 to 5:1. In some more preferred embodiments, the mass ratio of water to reactant may be from 0.5 to 3:1. In some further preferred embodiments, the mass ratio of water to reactant may be 1-2:1.
In some preferred embodiments, the filter aid may be one or more of diatomaceous earth, activated carbon, and white carbon, and may function to adsorb impurities and aid filtration.
In some preferred embodiments, the reactants may be injected below the water surface through a feed tube with a heat retaining jacket. The reactant obtained by the reaction has higher melting point, is easy to solidify at low temperature and has higher viscosity, and the part below the liquid level is easy to solidify at low temperature by directly introducing the reactant into water. In some more preferred embodiments, the temperature of the heat-insulating medium in the heat-insulating jacket may be 130-200 ℃, and the heat-insulating medium may be water vapor, organic heat-conducting medium or other common heat-insulating medium.
The preparation method provided by the invention can be operated in batch mode or continuous mode, and can be suitable for common reaction devices including, but not limited to, one-stage or multi-stage kettle reactors, tubular reactors, tower reactors and the like.
In a third aspect the present invention provides the use of a sodium polyetheraminoethylsulfonate according to any one of the preceding claims as a surfactant or chain extender.
In some preferred embodiments, the chain extender is a chain extender for the synthesis of aqueous polyurethane.
The technical scheme provided by the invention has the following advantages:
1) The polyether amine ethyl sodium sulfonate provided by the invention has a novel structure, can be used as a chain extender and a surfactant of aqueous polyurethane dispersion, expands the types of the sulfonic acid chain extender and the surfactant and improves the performance.
2) The preparation process of the polyether amine ethyl sodium sulfonate provided by the invention is simple and convenient, the process route is short, high-toxicity and high-risk raw materials are not needed, and the polyether amine ethyl sodium sulfonate is environment-friendly, low in cost and high in operability.
3) The polyether amine ethyl sodium sulfonate provided by the invention also has a simple post-treatment process, and can be purified conveniently by utilizing different solubilities of products and raw materials in water, so that the preparation process is further simplified, the preparation efficiency is improved, and the preparation cost is reduced.
In conclusion, the polyether amine ethyl sodium sulfonate provided by the invention has various functions, is safe and simple to manufacture, is suitable for industrial production, and is beneficial to improving the preparation and application of the aqueous polyurethane, so that the polyether amine ethyl sodium sulfonate has very important economic and social values.
Detailed Description
The technical scheme of the invention is further described in detail below with reference to specific embodiments.
The polyetheramine D400 used in the examples of the present invention is a terminal amine polyoxyethylene ether having a molecular weight of about 400, and other materials or reagents are commercially available products unless otherwise specified.
The percentages used in the examples of the present invention are mass percentages unless otherwise indicated.
Example 1
80kg of sodium isethionate, 300kg of polyetheramine D400 and 20kg of water were added to the reaction vessel, mixed and heated to 250℃for 0.75 hours.
Continuously adding the reacted materials in a reaction kettle into a stirring kettle containing 400kg of water through a feed pipe with a heat preservation jacket, wherein the temperature of a heat preservation medium in the heat preservation jacket is 130 ℃, inserting a pipe orifice of the feed pipe below the water surface, directly injecting the materials into the water, cooling to 60 ℃, dissolving reaction products, separating out unreacted polyether amine and a small amount of disubstituted matters, adding diatomite accounting for 0.5% of the total mass of the system into the water, filtering with active carbon, and obtaining polyether amine sodium ethyl sulfonate solution with the concentration of about 50% after filtering. The conversion of sodium isethionate was 98% and the selectivity of the target product (monosubstituted) was 92%.
The structure of the target product is characterized as follows: 1 H-NMR(CDCl 3 ，300MHz)δ：5.10～5.15(m，2H，N-H)，3.75～3.76(m，2H，C-H)，3.62～3.65(m，2H，C-H)，3.53～3.54(m，14H，C-H)，3.07～3.11(m，4H，C-H)，2.70～2.75(m，2H，C-H)，1.95～2.03(m，1H，N-H)。
example 2
Sodium isethionate, polyetheramine D400 and water were mixed by a preheater at feed rates of 200kg/h, 640kg/h and 20kg/h respectively and heated to 170℃and then the mixed material was fed into a tubular reactor for reaction with a residence time of 0.5h.
Continuously adding the reacted materials in the tubular reactor into a stirred tank containing water through a feed pipe with a heat preservation jacket, wherein the temperature of a heat preservation medium in the heat preservation jacket is 130 ℃, inserting a pipe orifice of the feed pipe below the water surface, directly injecting the materials into the water, cooling to 60 ℃, dissolving reaction products, precipitating unreacted polyether amine and a small amount of disubstituted matters, adding diatomite accounting for 0.5% of the total mass of the system into the water for auxiliary filtration, and filtering to obtain a product solution with the concentration of about 45%. The conversion rate of sodium isethionate is 97%, and the selectivity of the target product is 90%.
Example 3
Sodium isethionate, polyetheramine D400 and water were mixed by a preheater at feed rates of 25kg/h, 100kg/h and 20kg/h respectively and heated to 160℃and then the mixed material was fed into a first stage stirred tank reactor for reaction with a residence time of 0.5h.
The reacted material in the first-stage stirred tank reactor and polyetheramine D400 with the feeding speed of 120kg/h are mixed by a preheater and heated to 180 ℃, and then the mixed material enters the second-stage stirred tank reactor for reaction, wherein the retention time of the material is 0.5h.
Continuously adding the reacted materials in the second-stage stirred tank reactor into a stirred tank containing water through a feed pipe with a heat preservation jacket, wherein the temperature of a heat preservation medium in the heat preservation jacket is 130 ℃, inserting a pipe orifice of the feed pipe below the water surface, directly injecting the materials into the water, cooling to 60 ℃, dissolving reaction products, precipitating unreacted polyether amine and a small amount of disubstituted matters, adding diatomite accounting for 0.5% of the total mass of the system into the water for auxiliary filtration, and filtering to obtain a product solution with the concentration of about 38%. The conversion rate of sodium isethionate is 97%, and the selectivity of the target product is 93%.
Test example 1
The product solutions prepared in examples 1 to 3 were each formulated with other usual surfactants (sodium dodecyl benzene sulfonate SDBS, sodium dodecyl sulfate SDS and polysorbate-80) as an aqueous solution at a concentration of 0.1% by weight, and foam test was carried out at a rotation speed of 60 rpm using a 1L rotary foam machine, foam height at the beginning of the test and after 5 minutes of rotation.
Table 1 foam test results
Sample of Composition of the components Initial foam height Foam height after 5 minutes
1 SDBS 260 230
2 SDS 230 210
3 The product obtained in example 1 185 165
4 The product obtained in example 2 180 165
5 The product obtained in example 3 190 170
6 Polysorbate-80 170 160
As can be seen from the results in Table 1, the sodium polyetheramine ethylsulfonate product of the present invention has a stronger surface activity than the conventional polyether surfactant polysorbate-80, based on the comparison of the foam height as the surface activity, and the ethylenediamine ethylsulfonate has little surface activity.
Test example 2
The product solutions prepared in examples 1 to 3 and sodium ethylenediamine-based sulfonate (comparative solution) were each formulated as a 10wt.% strength solution, and then mixed and stirred with the same mass of 50% solids polyurethane dispersion at 30 ℃ to test the-NCO group content for various times to test the chain extension effect.
TABLE 2 chain extension test results
From the results in Table 2, the reactivity is characterized by the chain extension effect, and the reactivity of the polyether amine sodium ethanesulfonate product is equivalent to that of ethylenediamine sodium ethanesulfonate, so that the polyether amine sodium ethanesulfonate product can be used as a novel sulfonic acid type chain extender for synthesizing water-based polyurethane. The product of the invention also has surface activity, is used in a dispersion system, and has better dispersion performance and stability compared with a comparison solution.
Unless otherwise defined, all terms used herein are intended to have the meanings commonly understood by those skilled in the art.
The described embodiments of the present invention are intended to be illustrative only and not to limit the scope of the invention, and various other alternatives, modifications, and improvements may be made by those skilled in the art within the scope of the invention, and therefore the invention is not limited to the above embodiments but only by the claims.

Claims (10)

1. A sodium polyetheramine ethyl sulfonate having the structure of formula (i):
NaO 3 SCH 2 CH 2 NH-(CH 2 -CH 2 -O-) n -CH 2 -CH 2 -NH 2
(I)
Wherein n represents 5 to 50.
2. The process for producing sodium polyetheraminoethylsulfonate according to claim 1, wherein the sodium polyetheraminoethylsulfonate is produced by reacting a polyetheramine having a structure represented by the formula (I') with sodium isethionate in the presence of water as a catalyst;
NH 2 -(CH 2 -CH 2 -O-) n -CH 2 -CH 2 -NH 2
(I')
Wherein n is as defined in claim 1.
3. The method of claim 2, wherein the polyetheramine is one or both of polyetheramines D400, D2000.
4. A method according to claim 2 or 3, characterized in that the molar ratio of polyetheramine to sodium isethionate is 1.05-10:1, preferably 1.1-3.5:1.
5. The preparation process according to any of claims 2 to 4, characterized in that the catalyst is used in an amount of 0.1 to 30wt.%, preferably 0.5 to 20wt.%, more preferably 1 to 10wt.% of the polyetheramine.
6. The preparation method according to any one of claims 2 to 5, wherein the reaction temperature of the reaction is 150 to 350 ℃, preferably 160 to 300 ℃, more preferably 170 to 250 ℃; and/or
The reaction time of the reaction is 0.1 to 10 hours, preferably 0.2 to 5 hours, more preferably 0.3 to 1 hour.
7. The production method according to any one of claims 2 to 6, characterized in that the production method further comprises: after the reaction is finished, the obtained reactant is injected into water, filter aid is added and filtration is carried out, so that the aqueous solution of polyether amine sodium ethyl sulfonate with the concentration of 20-60 wt.% is obtained.
8. The method according to claim 7, wherein the filter aid is one or more of diatomaceous earth, activated carbon, and white carbon.
9. The preparation method according to claim 7 or 8, wherein the reactants are injected below the water surface through a feed pipe with a heat-preserving jacket, and the temperature of the heat-preserving medium in the heat-preserving jacket is 130-200 ℃.
10. Use of the sodium polyetheramine ethyl sulfonate of claim 1 as a surfactant or chain extender.
CN202310394263.4A 2023-04-13 2023-04-13 Polyether amine ethyl sodium sulfonate, preparation method and application thereof Pending CN116444783A (en)

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CN202310394263.4A CN116444783A (en) 2023-04-13 2023-04-13 Polyether amine ethyl sodium sulfonate, preparation method and application thereof

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Application Number Priority Date Filing Date Title
CN202310394263.4A CN116444783A (en) 2023-04-13 2023-04-13 Polyether amine ethyl sodium sulfonate, preparation method and application thereof

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