CN113501962B - Low-yellowing hydrophilic block polyether amino silicone oil and preparation method thereof - Google Patents
Low-yellowing hydrophilic block polyether amino silicone oil and preparation method thereof Download PDFInfo
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- CN113501962B CN113501962B CN202110904379.9A CN202110904379A CN113501962B CN 113501962 B CN113501962 B CN 113501962B CN 202110904379 A CN202110904379 A CN 202110904379A CN 113501962 B CN113501962 B CN 113501962B
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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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/42—Block-or graft-polymers containing polysiloxane sequences
- C08G77/46—Block-or graft-polymers containing polysiloxane sequences containing polyether sequences
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/643—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
- D06M15/647—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain containing polyether sequences
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
- D06M2200/50—Modified hand or grip properties; Softening compositions
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Abstract
The invention provides low-yellowing hydrophilic block polyether amino silicone oil and a preparation method thereof, wherein epoxy-terminated polyether silicone oil and diethylenetriamine are adopted according to the weight ratio of 1: 1.2-2.1, adding a solvent A (accounting for 0-20 wt% of reactants), heating to 60-90 ℃, reacting for 3-12h, adding fatty acid or fatty acid lactone (0.3-1.0 mol of diethylenetriamine), heating to 220 ℃, vacuumizing and dehydrating until no water is separated, cooling to 25-80 ℃, adding a solvent B (10-50%) and dimethyl sulfate (0.5-2.0 mol of diethylenetriamine), and thus obtaining the low-yellowing hydrophilic block polyether amino silicone oil. According to the invention, a quaternary ammonium salt structure is introduced to replace the original primary-secondary amine structure, so that the yellowing performance of the block polyether amino silicone oil can be improved, and the hydrophilic performance of the silicone oil can also be improved. On the other hand, long-chain alkyl is introduced into the organic silicon main chain, so that the softness of the silicone oil can be further improved, and the problem of reduction of the softness caused by a quaternary ammonium salt structure is avoided.
Description
Technical Field
The invention relates to the technical field of silicone oil synthesis, in particular to low-yellowing hydrophilic block polyether amino silicone oil and a preparation method thereof.
Background
The ternary block silicone oil mainly comprises a polysiloxane chain segment, a polyether chain segment and an amino group. Compared with the traditional amino silicone oil, the polyether chain segment of the ternary block silicone oil not only can provide emulsification assistance, but also endows the unique hand feeling finishing style. However, the primary amine group on the main chain of the block silicone oil still has the same fabric yellowing problem as the amino silicone oil, so that the main chain quaternized polyether block amino silicone oil can be prepared by introducing a quaternary ammonium group to the main chain of the block polyether amino silicone oil to replace the primary amine group, mainly taking epoxy silicone oil and polyether amine as raw materials and carrying out cationic modification by adopting a quaternizing agent, wherein the quaternizing agent comprises epoxypropyltrimethylammonium chloride, dimethyl sulfate, epichlorohydrin, ethyl chloroacetate, epoxy polyether and the like. Thus, while the hydrophilicity of the target silicone oil is improved and the yellowing thereof is reduced, the softening performance is greatly reduced. The long-chain quaternary ammonium salt containing imidazoline rings is one of cationic surfactants and is a non-silicon softening agent which can provide soft hand feeling of fabrics, and although the softening performance of the long-chain quaternary ammonium salt is different from that of an organic silicon softening agent in certain quantity, the softening agent is low in price, simple in package and convenient to transport, so that the long-chain quaternary ammonium salt containing imidazoline rings is widely applied to textile softening finishing. The inventor of the application tries to prepare the hydrophilic block polyether amino silicone oil with low yellowing performance by reacting polyether epoxy silicone oil with diethylenetriamine to generate block polyether amino silicone oil, then dehydrating the block polyether amino silicone oil with long-chain fatty acid or alkyl lactone at high temperature to form a ring, and finally adding a quaternizing agent to solve the problems.
Disclosure of Invention
The invention aims to provide low-yellowing hydrophilic block polyether amino silicone oil and a preparation method thereof, so as to overcome the defects of the prior art.
The technical scheme for solving the technical problem is as follows: the low-yellowing hydrophilic block polyether amino silicone oil has the molecular structural formula shown in the specification,
wherein z = 30-300;
the structure of R1 is as follows:
wherein, (x + y) = 10-50, and is an integer;
r2= H or CH 3;
r3 is a saturated linear or branched hydrocarbon chain segment with carbon number of 7-25, and carbon atom is substituted by hydroxyl.
A preparation method of low-yellowing hydrophilic block polyether amino silicone oil comprises the following steps: feeding the end polyether epoxy silicone oil and diethylenetriamine according to a certain molar ratio, adding a solvent A, wherein the solvent A accounts for 0-20% of the weight of the end polyether epoxy silicone oil, heating to 60-90 ℃, reacting for 3-12h, then adding fatty acid or fatty acid lactone, wherein the proportion of the fatty acid or the fatty acid accounts for 0.3-1.0% of the molar number of the diethylenetriamine, heating to 120-220 ℃, vacuumizing for dehydration until no water is separated, then cooling to 25-80 ℃, adding a solvent B and dimethyl sulfate, wherein the proportion of the solvent B accounts for 10-50% of the weight of the end polyether epoxy silicone oil, and the proportion of the dimethyl sulfate accounts for 0.5-2.0 of the molar number of the diethylenetriamine, and obtaining the low-yellowing hydrophilic block polyether amino silicone oil; the mol ratio of the polyether-terminated epoxy silicone oil to the diethylenetriamine is 1: 1.2-2.1; the structural formula of the polyether-terminated epoxy silicone oil is as follows,
wherein the content of the first and second substances,
z= 30~300；
wherein, R1 has the structural formula as follows,
in the above formula, (x + y) =10~50, and is an integer.
Further, the solvents A and B are alcohol ether solvents, including one or more of ethylene glycol monobutyl ether, diethylene glycol monoethyl ether, diethylene glycol monopropyl ether, diethylene glycol monobutyl ether, diethylene glycol mono-tert-butyl ether, diethylene glycol hexyl ether, dipropylene glycol methyl ether, propylene glycol butyl ether, glycol monoisooctyl ether, dimethyl-1, 3-dioxolane-4-methanol, methyl-2, 4-pentanediol, methoxy-3-methylbutanol, ethylene glycol phenyl ether, and propylene glycol phenyl ether.
Further, the fatty acid includes one or more of caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, arachidic acid, and the like.
Further, the fatty acid lactone comprises one or more of beta-propionyl lactone, gamma-butyrolactone, gamma-valerolactone, epsilon-caprolactone and the like.
The invention has the beneficial effects that:
according to the invention, the quaternary ammonium salt structure is introduced to replace the original primary-secondary amine structure, so that the yellowing performance of the block polyether amino silicone oil can be improved, and the hydrophilic performance of the silicone oil can also be improved. On the other hand, long-chain alkyl is introduced into the organic silicon main chain, so that the softness of the silicone oil can be further improved, and the problem of reduction of the softness caused by a quaternary ammonium salt structure is avoided.
Detailed Description
The following detailed description of embodiments of the invention is intended to be illustrative, but not limiting, of the invention.
Example 1
100 g of polyether-terminated epoxy silicone oil (x =10, y =0, z = 30) and 6.61 parts of diethylenetriamine (64 mmol) are added into a four-neck flask provided with a thermometer and a reflux condenser tube, no solvent A is added, stirring is carried out at 60 ℃ for reaction for 3 hours, then 5.47 parts of stearic acid (19 mmol) is added, the temperature is raised to 120 ℃, vacuum dehydration is carried out until no water is removed, the temperature is reduced to 25 ℃ at room temperature, 10 parts of diethylene glycol monobutyl ether and 16.18 parts of dimethyl sulfate (128 mmol) are added, and stirring is carried out, so that the low-yellowing hydrophilic block polyether amino silicone oil is obtained.
Example 2
100 g of end polyether epoxy silicone oil (x =25, y =25, z = 108) and 1.41 parts of diethylenetriamine (14 mmol) are added into a four-neck flask provided with a thermometer and a reflux condenser, 10 parts of solvent ethylene glycol monobutyl ether is added under the stirring condition, the mixture is stirred and reacted for 6 hours at 80 ℃, then 2.19 parts of lauric acid (11 mmol) are added, the temperature is increased to 180 ℃, vacuum dehydration is carried out until no water is removed, the temperature is reduced to 60 ℃ at room temperature, 20 parts of ethylene glycol butyl ether and 2.58 parts of dimethyl sulfate (21 mmol) are added, and stirring is carried out, thus obtaining the low-yellowing hydrophilic block polyether amino silicone oil.
Example 3
100 g of terminal polyether epoxy silicone oil (x =13, y =6, z = 135) and 1.38 parts of diethylenetriamine (13 mmol) are added into a four-neck flask provided with a thermometer and a reflux condenser, 10 parts of solvent ethylene glycol phenyl ether is added under the stirring condition, the mixture is stirred and reacted for 8 hours at 80 ℃, then, 0.77 part of butyrolactone (11 mmol) is added, the temperature is increased to 180 ℃, vacuum dehydration is carried out until no water is removed, the temperature is reduced to 60 ℃, 20 parts of ethylene glycol butyl ether and 2.53 parts of dimethyl sulfate (20 mmol) are added, and stirring is carried out, so that the low-yellowing hydrophilic block polyether amino silicone oil is obtained.
Example 4
Adding 100 g of end polyether epoxy silicone oil (x =8, y =3, z = 300) and 0.53 part of diethylenetriamine (5 mmol) into a four-neck flask provided with a thermometer and a reflux condenser, adding 20 parts of solvent butyl cellosolve under the stirring condition, stirring and reacting at 90 ℃ for 12 hours, then adding 0.51 part of caprolactone (5 mmol), heating to 220 ℃, carrying out vacuum dehydration until no water is removed, cooling to room temperature of 80 ℃, adding 50 parts of butyl cellosolve and 0.65 part of dimethyl sulfate (5 mmol), and stirring to obtain the low-yellowing hydrophilic block polyether amino silicone oil.
Example 5
100 g of end polyether epoxy silicone oil (x =8, y =3, z = 175) and 1.45 parts of diethylenetriamine (14 mmol) are added into a four-neck flask provided with a thermometer and a reflux condenser, 10 parts of solvent butyl glycol ether is added under the stirring condition, the mixture is stirred and reacted for 8 hours at 70 ℃, then 4.01 parts of stearic acid (14 mmol) is added, the temperature is increased to 180 ℃, vacuum dehydration is carried out until no water is removed, the temperature is reduced to 60 ℃ at room temperature, 20 parts of butyl glycol ether and 2.67 parts of dimethyl sulfate (21 mmol) are added, and stirring is carried out, so that the low-yellowing hydrophilic block polyether amino silicone oil is obtained.
Comparative example
100 g of polyether-terminated epoxy silicone oil (x =8, y =3, z = 175) and 1.45 parts of diethylenetriamine (14 mmol) are added into a four-neck flask provided with a thermometer and a reflux condenser tube, 30 parts of ethylene glycol monobutyl ether is added under the stirring condition, the mixture is stirred and reacted for 8 hours at 70 ℃, 2.5 parts of glacial acetic acid is added, and the mixture is stirred to obtain the common block polyether amino silicone oil.
Adding 100 parts of the polyether amino silicone oil copolymer into an emulsifying kettle, adding 20 parts of emulsifier TO-10, adding 10 parts of cosolvent glycerol, starting an emulsifying machine and setting the rotating speed TO be 500 r/min; then adding 0.1 part of acetic acid into the emulsifying kettle for 3 times, wherein the interval between every two times is 1min, and the stirring time is 3 min/time; adding 1/5 of 150 parts of water into an emulsifying kettle, and stirring for 5 min/time; and finally, increasing the rotating speed to 1600r/min, adding the rest water into the emulsifying kettle for 10 times, and stirring for 8 min/time to obtain the soft finishing agent.
The invention compares the above examples and comparative examples.
The sample preparation method comprises the following steps: the soft finishing agents prepared in the above examples and comparative examples are respectively prepared into 20% aqueous solutions, pure white knitted cotton cloth is used as a cloth sample, the dosage is 60g/L, one immersion and one rolling are carried out, and the sample A, the sample B, the sample C, the sample D, the sample E and the comparative sample are respectively corresponding to the example A, the example II, the example III, the example IV, the example V and the comparative example after setting and drying for 90 seconds at 170 ℃.
And (3) hand feeling test: the hand touch method is adopted, the main performance is soft and smooth, the comprehensive ranking evaluation is carried out by 5 professionals, the grade is 1-5, the best grade is 5, and the worst grade is 1.
Moisture absorption: the static water pick-up time was characterized by dropping 1 drop of water from a height of 2 cm from the fabric to the surface of the flat laid fabric using a standard dropper (25 drops/mL) and the time taken for the fabric to take up the water drop was measured under static conditions.
Whiteness: according to the GB 8425-87 standard, the whiteness value is measured by a WSB-2 type digital whiteness meter, 5 different parts of a test cloth sample are selected to measure the whiteness value, and the average value is taken as a test result. The larger the whiteness data, the better the cloth-like whiteness.
The comparison results are as follows:
the above embodiments are preferred embodiments of the present invention, but the present invention is not limited to the above embodiments, and any other changes, modifications, substitutions, combinations, and simplifications which do not depart from the spirit and principle of the present invention should be construed as equivalents thereof, and all such modifications are intended to be included in the scope of the present invention.
Claims (2)
1. The low-yellowing hydrophilic block polyether amino silicone oil is characterized in that: the molecular structural formula is as follows,
wherein z is 30-300;
the structure of R1 is as follows:
wherein (x + y) is 10 to 50 and is an integer;
r2 ═ H or CH 3; r3 is a saturated linear or branched hydrocarbon chain segment with carbon number of 7-25, and carbon atom is substituted by hydroxyl.
2. The preparation method of the low-yellowing hydrophilic block polyether amino silicone oil according to claim 1, characterized in that: the polyether-terminated epoxy silicone oil and diethylenetriamine are mixed according to a molar ratio of 1: 1.2-2.1, adding a solvent A, wherein the using amount of the solvent A is 0-20% of the weight of the polyether-terminated epoxy silicone oil; heating to 60-90 ℃, reacting for 3-12h, adding fatty acid or fatty acid lactone, wherein the proportion of the fatty acid or the fatty acid is 0.3-1.0 of the mol number of the diethylenetriamine, heating to 120-220 ℃, vacuumizing and dehydrating until no water is separated, then cooling to 25-80 ℃, adding a solvent B and dimethyl sulfate, wherein the amount of the solvent B is 10-50% of the weight of the polyether-terminated epoxy silicone oil, and the proportion of the dimethyl sulfate is 0.5-2.0 of the mol number of the diethylenetriamine, thus obtaining the low-yellowing hydrophilic block polyether amino silicone oil; the structural formula of the polyether-terminated epoxy silicone oil is as follows,
wherein, the first and the second end of the pipe are connected with each other,
z is 30-300; the structural formula of R1 is as follows,
in the above formula, (x + y) is 10 to 50 and is an integer;
the solvents A and B are alcohol ether solvents, including one or more of ethylene glycol monobutyl ether, diethylene glycol monoethyl ether, diethylene glycol monopropyl ether, diethylene glycol monobutyl ether, diethylene glycol mono-tertiary butyl ether, diethylene glycol hexyl ether, dipropylene glycol methyl ether, propylene glycol butyl ether, glycol monoisooctyl ether, dimethyl-1, 3-dioxolane-4-methanol, methyl-2, 4-pentanediol, methoxy-3-methyl butanol, ethylene glycol phenyl ether, and propylene glycol phenyl ether;
the fatty acid comprises one or more of caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, and arachidic acid;
the fatty acid lactone comprises one or more of beta-propionyl lactone, gamma-butyrolactone, gamma-valerolactone and epsilon-caprolactone.
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