CN112143280B - Composition containing reactive anionic surfactant and preparation method thereof - Google Patents

Composition containing reactive anionic surfactant and preparation method thereof Download PDF

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CN112143280B
CN112143280B CN202011091617.0A CN202011091617A CN112143280B CN 112143280 B CN112143280 B CN 112143280B CN 202011091617 A CN202011091617 A CN 202011091617A CN 112143280 B CN112143280 B CN 112143280B
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anionic surfactant
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reactive anionic
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CN112143280A (en
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王念贵
汤诚
华成明
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Wuhan Shiquanxing New Material Science And Technology Co ltd
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/60—Additives non-macromolecular
    • C09D7/63—Additives non-macromolecular organic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
    • C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
    • C07C211/27—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring having amino groups linked to the six-membered aromatic ring by saturated carbon chains
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
    • C07D251/30—Only oxygen atoms
    • C07D251/34—Cyanuric or isocyanuric esters

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Abstract

The invention provides a composition containing a reactive anionic surfactant and a preparation method thereof. The composition comprises a reactive anionic surfactant and a diluent, wherein the anionic surfactant is an organic sulfonate and accounts for 1-10% of the weight of the composition. The preparation method of the composition comprises the following steps: mixing trimeric hexamethylene diisocyanate, sulfamic acid, tertiary amine and a diluent in a certain ratio, and heating and stirring the mixture to react under the condition of nitrogen; and cooling to room temperature after the reaction is stopped to obtain the composition containing the anionic surfactant with the reaction activity. The composition containing the anionic surfactant with reactivity is used as a sulfonic acid type waterborne polyurethane curing agent, has simple components, is easy to disperse in water, has good storage stability, and improves the overall performance of a prepared paint film compared with a paint film prepared by a current commercially available curing agent. The preparation method of the composition has the advantages of low requirement on reaction conditions, simplicity, easiness in operation and short reaction time.

Description

Composition containing reactive anionic surfactant and preparation method thereof
Technical Field
The invention relates to a surfactant composition and a preparation method thereof, in particular to a composition containing an anionic surfactant with reactivity and a preparation method thereof, which are applied to the fields of aqueous resin coatings, adhesives and the like.
Background
The water-based resin uses water as a dispersing agent, has the advantages of environmental protection, saving money, fire prevention, easy construction and the like, and is widely applied to the fields of paint, adhesion, coating, printing and dyeing, leather finishing and the like. However, due to the linear molecular structure and the hydrophilic group attached to the water-based resin, the water-based resin is low in paint film strength and poor in water resistance after being cured into a film.
Therefore, the water-based curing agent is used by being matched with water-based resin, and the water-based curing agent is separately stored before use; when in use, the paint is mixed with water-based resin, is constructed within a certain time, and forms a cross-linked network structure with the resin through chemical reaction, so that the strength and the water resistance of a paint film are improved. The application range of the water-based curing agent is enlarged year by year, and the dosage is increased year by year. The water-based curing agent has the largest use amount currently comprising a water-based epoxy curing agent and a water-based polyurethane curing agent, wherein the water-based epoxy curing agent is matched with water-based epoxy resin for use, and the water-based polyurethane curing agent is matched with water-based resin containing active hydrogen for use.
The waterborne polyurethane curing agent is a molecule which contains both hydrophilic groups and isocyanate groups and is generated by the reaction of polyisocyanate and hydrophilic monomers containing active hydrogen. There are two main classes, one anionic and the other nonionic. Anionic types are divided into carboxylic acid types and sulfonic acid types. The carboxylic acid-modified polyisocyanates are not dispersible in systems having a pH of less than 5 and, in addition, have poor storage stability. Therefore, the sulfonic acid type waterborne polyurethane curing agent is a waterborne polyurethane curing agent widely used at present, but the current sulfonic acid type waterborne polyurethane curing agent has complex components, is not easy to disperse water, has harsh reaction conditions for preparation, complicated preparation process, long reaction time and high cost, and has a space for improving the properties of strength, hardness and the like of a prepared paint film.
Disclosure of Invention
In order to solve the defects in the prior art, the invention provides a composition containing an anionic surfactant with reaction activity and a preparation method thereof.
A composition containing reactive anionic surfactant, comprising reactive anionic surfactant and trimerized hexamethylene diisocyanate, wherein the weight ratio of the anionic surfactant to the composition is 1-10%, and the structural formula of the composition is as follows:
Figure BDA0002722305790000021
wherein n is 1, 2; wherein R is1、R2And R3Aliphatic and/or alicyclic substituent groups. The diluent comprises one or more of trimeric hexamethylene diisocyanate, ethyl acetate, dimethyl carbonate, trimeric isophorone diisocyanate, methyl stearate, methyl palmitoleate, propylene glycol methyl ether acetate, dipropylene glycol methyl ether acetate, ethylene glycol methyl ether acetate and diethylene glycol methyl ether acetate. The diluent is preferably a mixture of polyhexamethylene diisocyanate and other components in a weight ratio of 41:8, and the other components are preferably ethylene in a weight ratio of 3:1A mixture of ethyl acid and dimethyl carbonate. In the structural formula of the anionic surfactant, n ═ 1 is preferred.
A method for preparing a composition comprising a reactive anionic surfactant, comprising the steps of:
(1) three reactants, trimeric hexamethylene diisocyanate, the structural formula of which is Ph (CH)2)n NH(CH2)3SO3Weighing the sulfamic acid and the tertiary amine of H according to the molar ratio of 1:1: 1; weighing 9-99 times of diluent in the total weight of the three reactants, wherein n in sulfamic acid is 1, 2;
(2) adding trimeric hexamethylene diisocyanate, sulfamic acid, tertiary amine and diluent into a reaction vessel filled with nitrogen, heating to 85-115 ℃, and stirring for 2-4 h;
(3) stopping the reaction, and cooling to room temperature to obtain the composition containing the anionic surfactant with the reaction activity.
The diluent comprises one or more of trimeric hexamethylene diisocyanate, ethyl acetate, dimethyl carbonate, trimeric isophorone diisocyanate, methyl stearate, methyl palmitoleate, propylene glycol methyl ether acetate, dipropylene glycol methyl ether acetate, ethylene glycol methyl ether acetate and diethylene glycol methyl ether acetate. The diluent is preferably prepared by mixing polyhexamethylene diisocyanate with a mixture of ethyl acetate and dimethyl carbonate, and the weight ratio of the polyhexamethylene diisocyanate to the mixture of ethyl acetate and dimethyl carbonate is 41: 8. The weight ratio of the ethyl acetate to the dimethyl carbonate is preferably 3: 1. The tertiary amine is aliphatic and/or alicyclic substituted tertiary amine, preferably one or more of triethylamine, N-dimethylcyclohexylamine, N-dimethylbenzylamine and N-methylmorpholine.
The diluent is mainly used as a dispersant in the reaction system, and the diluent promotes the reaction during the reaction and enables the anionic surfactant with the reaction activity to be dispersed more uniformly in the composition after the reaction. Tests show that under the same other conditions, the mixture of the polyhexamethylene diisocyanate and other substances is used as a dispersing agent, particularly the mixture of the polyhexamethylene diisocyanate, the ethyl acetate and the dimethyl carbonate in the weight ratio of 41:6:2 is used as the dispersing agent, the dispersibility of the mixture is slightly better than that of a single component or other components, and the overall performance of a paint film prepared from the obtained composition is optimal.
Under the same other conditions, the structural formula is PhCH2NH(CH2)3SO3Sulfamic acid of H as a reactant, the properties of the resulting composition and Ph (CH)2)2NH(CH2)3SO3H is used as a reactant to prepare compositions without distinction, but the cost is much lower.
The composition containing the anionic surfactant with reactivity is used as a sulfonic acid type waterborne polyurethane curing agent, has simple components, is easy to disperse in water, has good storage stability, is matched with waterborne resin containing active hydrogen for use, and the prepared mixture has longer activation period, high drying speed, good strength and high hardness of a dried and formed material, good water resistance and high glossiness. The preparation reaction condition of the composition is low, the operation is simple and easy, and the reaction time is short.
Detailed Description
The present invention will be described in further detail with reference to specific examples. It should be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention.
Example 1
The preparation of composition I containing a reactive anionic surfactant was as follows:
(1) 50.4g (0.1mol) of trimeric hexamethylene diisocyanate are weighed; 22.9g (0.1mol) of sulfamic acid of the formula PhCH2NH(CH2)3SO3H; 13.5g (0.1mol) of N, N-dimethylbenzylamine are weighed; 3430g of trimeric hexamethylene diisocyanate are weighed;
(2) adding all the weighed trimeric hexamethylene diisocyanate into a four-neck round-bottom flask provided with a mechanical stirrer, a reflux pipe, a thermometer and a nitrogen inlet and outlet, and adding the weighed PhCH2NH(CH2)3SO3H and N, N-dimethylbenzylamine, heating in water bath while stirring to 95 deg.c within 30min, and stirring at 95-105 deg.c for 3 hr at 300-500 rmp;
(3) the water bath was removed and the stirrer was turned off, the reaction was stopped and the reaction product was cooled to room temperature to give composition I containing the reactive anionic surfactant.
The preparation process involves the reaction of trimeric hexamethylene diisocyanate with PhCH2NH(CH2)3SO3H in the presence of N, N-dimethylbenzylamine to form a reactive anionic surfactant:
Figure BDA0002722305790000051
ideally, the composition I containing the reactive anionic surfactant comprises the following components:
86.8g (0.1mol) of reactive anionic surfactant, and the structural formula of the surfactant is as follows:
Figure BDA0002722305790000061
② trimerized hexamethylene diisocyanate, the weight is 3430 g.
From the above, it can be calculated that the weight ratio of the anionic surfactant having reactivity to the composition I is 2.47%.
Example 2
Composition II containing a reactive anionic surfactant was prepared as follows:
(1) 50.4g (0.1mol) of trimeric hexamethylene diisocyanate are weighed; 24.3g (0.1mol) of sulfamic acid is weighed, and the structural formula is Ph (CH)2)2NH(CH2)3SO3H; 13.5g (0.1mol) of N, N-dimethylbenzylamine are weighed; 3430g of trimeric hexamethylene diisocyanate are weighed;
(2) burning at four-port round bottom with mechanical stirrer, reflux pipe, thermometer and nitrogen inlet and outletAdding all the weighed trimeric hexamethylene diisocyanate and propylene glycol monomethyl ether acetate into a bottle, and adding the weighed Ph (CH)2)2NH(CH2)3SO3H and N, N-dimethylbenzylamine, heating in water bath while stirring to 85 deg.c within 30min, and stirring at 300-500 rmp for 4 hr at 85-95 deg.c;
(3) the water bath was removed and the stirrer was then turned off, the reaction was stopped and the reaction product was cooled to room temperature to provide composition II containing the reactive anionic surfactant.
The preparation involves the reaction of trimerized hexamethylene diisocyanate with Ph (CH)2)2NH(CH2)3SO3H in the presence of N, N-dimethylbenzylamine to form a reactive anionic surfactant:
Figure BDA0002722305790000071
ideally, the composition II containing the reactive anionic surfactant comprises the following components:
(ii) 88.2g (0.1mol) of a reactive anionic surfactant having the formula:
Figure BDA0002722305790000072
② trimerized hexamethylene diisocyanate, the weight is 3430 g.
From the above, it can be calculated that the weight ratio of the anionic surfactant having reactivity to the composition II is 2.51%.
Example 3
The preparation of composition III containing a reactive anionic surfactant was as follows:
(1) 50.4g (0.1mol) of trimerized hexamethylene diisocyanate are weighed; 22.9g (0.1mol) of sulfamic acid of the formula PhCH2NH(CH2)3SO3H; 13.5g (0.1mol) of N, N-dimethyl are weighed outBenzylamine; weighing 3430g of trimeric isophorone diisocyanate;
(2) adding all the weighed trimeric isophorone diisocyanate into a four-neck round-bottom flask provided with a mechanical stirrer, a reflux pipe, a thermometer and a nitrogen inlet and outlet, and adding the weighed trimeric hexamethylene diisocyanate and PhCH2NH(CH2)3SO3H and N, N-dimethylbenzylamine, heating in water bath while stirring to 105 deg.c within 30min, and stirring at 300-500 rmp for 2 hr at 105-115 deg.c;
(3) the water bath was removed and the stirrer was turned off, the reaction was stopped and the reaction product was cooled to room temperature to provide composition III containing the reactive anionic surfactant.
The preparation process involves the reaction of trimeric hexamethylene diisocyanate with PhCH2NH(CH2)3SO3H in the presence of N, N-dimethylbenzylamine to form a reactive anionic surfactant:
Figure BDA0002722305790000091
ideally, the composition III containing the reactive anionic surfactant comprises:
(ii) a reactive anionic surfactant weighing 86.8g (0.1mol) and having the formula:
Figure BDA0002722305790000092
② trimerization isophorone diisocyanate, the weight is 3430 g.
From the above, it can be calculated that the weight ratio of the anionic surfactant having reactivity to the composition III is 2.47%.
Example 4
Composition IV containing a reactive anionic surfactant was prepared as follows:
(1) 50.4g (0.1mol) of polyhexamethylene are weighed outMethyl diisocyanate; 22.9g (0.1mol) of sulfamic acid of the formula PhCH2NH(CH2)3SO3H; 13.5g (0.1mol) of N, N-dimethylbenzylamine are weighed; then 2870g of trimeric hexamethylene diisocyanate and 560g of methyl stearate are weighed;
(2) adding all the weighed trimeric hexamethylene diisocyanate and methyl stearate into a four-neck round-bottom flask provided with a mechanical stirrer, a reflux pipe, a thermometer and a nitrogen inlet and outlet, and adding the weighed PhCH2NH(CH2)3SO3H and N, N-dimethylbenzylamine, heating in water bath while stirring to 95 deg.c within 30min, and stirring at 95-105 deg.c for 3 hr at 300-500 rmp;
(3) the water bath was removed and the stirrer was turned off to stop the reaction and the reaction product was cooled to room temperature to give composition IV containing the reactive anionic surfactant.
The preparation process involves the reaction of trimeric hexamethylene diisocyanate with PhCH2NH(CH2)3SO3H in the presence of N, N-dimethylbenzylamine to form a reactive anionic surfactant:
Figure BDA0002722305790000101
ideally, the composition IV containing the reactive anionic surfactant comprises the following components:
(ii) a reactive anionic surfactant weighing 86.8g (0.1mol) and having the formula:
Figure BDA0002722305790000111
2870g of trimerized hexamethylene diisocyanate;
③ methyl stearate, 560 g.
From the above, it can be calculated that the weight ratio of the anionic surfactant having reactivity to the composition IV is 2.47%.
Example 5
Composition V, containing a reactive anionic surfactant, was prepared as follows:
(1) 50.4g (0.1mol) of trimeric hexamethylene diisocyanate are weighed; 22.9g (0.1mol) of sulfamic acid, the structural formula of which is PhCH, are weighed2NH(CH2)3SO3H; 13.5g (0.1mol) of N, N-dimethylbenzylamine are weighed; then 2870g of trimeric hexamethylene diisocyanate, 420g of ethyl acetate and 140g of dimethyl carbonate are weighed;
(2) adding all the weighed trimeric hexamethylene diisocyanate, ethyl acetate and dimethyl carbonate into a four-neck round-bottom flask provided with a mechanical stirrer, a reflux pipe, a thermometer and a nitrogen inlet and outlet, and adding the weighed PhCH2NH(CH2)3SO3H and N, N-dimethylbenzylamine, heating in water bath while stirring to 95 deg.c within 30min, and stirring at 95-105 deg.c for 3 hr at 300-500 rmp;
(3) the water bath was removed and the stirrer was turned off, the reaction was stopped and the reaction product was cooled to room temperature to provide composition V containing the reactive anionic surfactant.
The preparation process involves the reaction of trimeric hexamethylene diisocyanate with PhCH2NH(CH2)3SO3H in the presence of N, N-dimethylbenzylamine to form a reactive anionic surfactant:
Figure BDA0002722305790000121
ideally, the composition V containing the reactive anionic surfactant comprises the following components:
(ii) a reactive anionic surfactant weighing 86.8g (0.1mol) and having the formula:
Figure BDA0002722305790000122
2870g of trimerized hexamethylene diisocyanate;
③ Ethyl propyl acetate, the weight is 420 g;
dimethyl carbonate, 140g in weight.
From the above, it can be calculated that the weight ratio of the anionic surfactant having reactivity to the composition V was 2.47%.
The paint films prepared from the compositions prepared in the above 5 examples and commercial curing agents were subjected to various performance tests. In the performance test, the adopted commercial curing agent is a curing agent which is widely applied at present and prepared by adopting aminopropanesulfonic acid and isocyanate. The preparation method of the test sample plate comprises the following steps: the preparation method comprises the steps of preparing a varnish by matching a curing agent with a commercially available hydroxyl acrylic dispersion, preparing a paint film sample according to GB1727-1992 general paint film preparation method, wherein the thickness of the paint film is 30 mu m, and after the paint film is flashed for 15min in a thermostatic chamber at 25 ℃, the paint film is dried at 80 ℃ for 30 min.
The hardness test is carried out according to GB/T6739-2006 determination of paint film hardness by a colored paint and varnish pencil method; the surface dry time is tested according to GB/T1728-1979 method for measuring the dry time of paint films and putty films; the strength is tested according to GB/T1732-93 determination method for impact resistance of paint film; the water resistance is tested according to GB/T1733-93 determination method for water resistance of paint film; the gloss is tested according to GB/T9754-2007 determination of gloss of paint films; the viscosity is measured according to GB/T9751-1988, determination of the viscosity of coatings at high shear rates.
The test method of the activation period comprises the following steps: adding a defoaming agent, a leveling agent, a film-forming aid and deionized water into commercially available hydroxy acrylic acid dispersoid according to a certain proportion under medium-speed stirring, dispersing for 20-30min to obtain varnish, mixing a curing agent with hydroxy acrylic acid resin in the varnish according to the equivalent NCO/OH of 1.4/1.0, and mixing and dispersing for 5-10 min at the rotating speed of 600-800 r/min. After the mixture was obtained, a sample was taken to prepare a test plate, and the gloss was measured. Adjusting viscosity of the mixture to 300-350 cps with deionized water, and standing at 25 deg.C and 50% RH humidity. And starting timing, sampling every 30min to prepare a test sample, and then testing the gloss of the test sample until the gloss of the paint film is compared with the initial gloss and the light loss rate is less than 20%, wherein the timing time is the activation period.
Table 1 shows a comparison table of properties of paint films prepared from curing agents, and it can be seen that the paint films prepared from the compositions of the examples as curing agents have improved impact strength, higher hardness, shorter surface drying time, better water resistance, longer activation period, and higher gloss, i.e., the overall properties are improved, compared with the paint films prepared from the current commercially available curing agents.
In addition, the comparison of the properties of the composition I and the composition II shows that the sulfamic acid has different structures, and the overall properties of the paint films prepared from the obtained compositions are not greatly different. But using PhCH2NH(CH2)3SO3H is used as a reactant, so that the cost is lower. As can be seen from the comparison of the performances of the five compositions, when the diluent is a mixture of polyhexamethylene diisocyanate, ethyl acetate and dimethyl carbonate in a weight ratio of 41:6:2, the overall performance of the paint film prepared from the obtained composition is optimal, the surface drying time is relatively shortest, the activation period is relatively longest, and the glossiness of the prepared paint film is relatively highest.
TABLE 1 comparison of the Properties of the paint films obtained with the curing agents
Figure BDA0002722305790000141
Figure BDA0002722305790000151

Claims (4)

1. A composition comprising a reactive anionic surfactant, wherein: the composition comprises a reactive anionic surfactant and a diluent, wherein the anionic surfactant accounts for 1-10% of the composition by weight, and the structural formula of the composition is as follows:
Figure DEST_PATH_IMAGE001
wherein n =1, 2; wherein R is1、R2And R3Is an aliphatic and/or cycloaliphatic substituent; the diluent is a mixture of polyhexamethylene diisocyanate, ethyl acetate and dimethyl carbonate in a weight ratio of 41:6: 2.
2. A composition comprising a reactive anionic surfactant according to claim 1, wherein: in the structural formula of the anionic surfactant, n = 1.
3. A process for preparing a composition comprising a reactive anionic surfactant as claimed in claim 1 or claim 2, wherein: the preparation method comprises the following steps:
(1) three reactants, trimeric hexamethylene diisocyanate, the structural formula of which is Ph (CH)2)n NH(CH2)3SO3Weighing the sulfamic acid and the tertiary amine of H according to the molar ratio of 1:1: 1; weighing 9-99 times of diluent of the total weight of the three reactants, wherein n =1,2 in sulfamic acid;
(2) adding trimeric hexamethylene diisocyanate, sulfamic acid, tertiary amine and a diluent into a reaction vessel filled with nitrogen, heating to 85-115 ℃, and stirring for reaction for 2-4 hours;
(3) stopping the reaction, and cooling to room temperature to obtain the composition containing the anionic surfactant with the reaction activity.
4. A process for preparing a composition containing a reactive anionic surfactant according to claim 3, wherein: the tertiary amine is one or more of triethylamine, N-dimethylcyclohexylamine, N-dimethylbenzylamine and N-methylmorpholine.
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