CN117449097A - Diamine modified cationic film and preparation method thereof - Google Patents
Diamine modified cationic film and preparation method thereof Download PDFInfo
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- CN117449097A CN117449097A CN202311349236.1A CN202311349236A CN117449097A CN 117449097 A CN117449097 A CN 117449097A CN 202311349236 A CN202311349236 A CN 202311349236A CN 117449097 A CN117449097 A CN 117449097A
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- dripping
- acid
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- diethylenetriamine
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- 238000002360 preparation method Methods 0.000 title claims abstract description 14
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims abstract description 22
- 235000021355 Stearic acid Nutrition 0.000 claims abstract description 22
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims abstract description 22
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims abstract description 22
- 239000008117 stearic acid Substances 0.000 claims abstract description 22
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 21
- 238000006243 chemical reaction Methods 0.000 claims abstract description 19
- 238000010438 heat treatment Methods 0.000 claims abstract description 17
- 238000001816 cooling Methods 0.000 claims abstract description 14
- 239000002253 acid Substances 0.000 claims abstract description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229960000583 acetic acid Drugs 0.000 claims abstract description 10
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000012362 glacial acetic acid Substances 0.000 claims abstract description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 9
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims abstract description 7
- 238000007599 discharging Methods 0.000 claims abstract description 7
- 238000002844 melting Methods 0.000 claims abstract description 6
- 230000008018 melting Effects 0.000 claims abstract description 6
- 238000005070 sampling Methods 0.000 claims abstract description 6
- 239000007787 solid Substances 0.000 claims abstract description 6
- 238000003756 stirring Methods 0.000 claims abstract description 6
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 5
- 238000010992 reflux Methods 0.000 claims abstract description 5
- 125000002091 cationic group Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000002752 cationic softener Substances 0.000 abstract description 5
- 230000001276 controlling effect Effects 0.000 description 14
- 239000004744 fabric Substances 0.000 description 9
- 239000006260 foam Substances 0.000 description 7
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 229930195729 fatty acid Natural products 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- -1 fatty acid salt Chemical class 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 3
- 230000006641 stabilisation Effects 0.000 description 3
- 238000011105 stabilization Methods 0.000 description 3
- 239000004753 textile Substances 0.000 description 3
- 238000004383 yellowing Methods 0.000 description 3
- 239000004902 Softening Agent Substances 0.000 description 2
- 230000002152 alkylating effect Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000012752 auxiliary agent Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- QWXYZCJEXYQNEI-OSZHWHEXSA-N intermediate I Chemical compound COC(=O)[C@@]1(C=O)[C@H]2CC=[N+](C\C2=C\C)CCc2c1[nH]c1ccccc21 QWXYZCJEXYQNEI-OSZHWHEXSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000002736 nonionic surfactant Substances 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 238000009987 spinning Methods 0.000 description 2
- 229920002972 Acrylic fiber Polymers 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000007112 amidation reaction Methods 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000009954 braiding Methods 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 229940085805 fiberall Drugs 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- JVKAWJASTRPFQY-UHFFFAOYSA-N n-(2-aminoethyl)hydroxylamine Chemical compound NCCNO JVKAWJASTRPFQY-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000009941 weaving Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 238000004804 winding Methods 0.000 description 1
Classifications
-
- 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
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/372—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen containing etherified or esterified hydroxy groups ; Polyethers of low molecular weight
-
- 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
Abstract
The invention discloses a diamine modified cationic film and a preparation method thereof, firstly, 500-700g of stearic acid is heated to 100 ℃ for melting, 18-28g of 2,2' -dihydroxydiethylamine and 8-10g of p-toluenesulfonic acid are added after the solid stearic acid is completely melted, nitrogen is introduced for protection, reflux condensed water is opened, stirring is started, and the temperature is raised to 180-200 ℃ for reaction for 2-4 hours; then cooling the reaction product to 85-100 ℃ to start dripping diethylenetriamine, controlling the dripping temperature to be 100-120 ℃, controlling the dripping amount of diethylenetriamine to be 71-81g, controlling the dripping time to be within 1 hour, heating to 170 ℃ to perform constant temperature reaction for 6 hours after dripping is completed, sampling and analyzing the acid value, cooling to 100 ℃ to add 15-21g glacial acetic acid to perform reaction for 60 minutes when the acid value is close to or reaches a theoretical value, and discharging and slicing. The content of the two cationic softeners is controlled, so that the softness, the fluffiness and the smoothness are improved, the addition amount of glacial acetic acid is controlled, and the softness is not influenced and meanwhile, the hydrophilic performance is good.
Description
Technical field:
the invention belongs to the technical field of textile assistants, and particularly relates to a diamine modified cationic film and a preparation method thereof.
The background technology is as follows:
the soft sheet is used as a textile softener, can obtain soft, fluffy and plump hand feeling when used for finishing fabrics, and can improve the friction resistance and tearing strength of the fabrics. The spinning, stretching, winding drum, braiding, spinning and weaving processes of the chemical fiber all use softening agents, and the main functions of the softening agents are to meet the different handfeel, different styles and requirements of various textiles. The fatty acid salt cationic softener generated by amidation reaction of stearic acid and amine is one of common softeners, has the advantages of convenient transportation, use and storage, but has large dosage and higher cost, and the prior art cannot realize cost reduction, and has extremely limited or even no anti-yellowing and antibacterial capabilities. The following are some of the prior art fatty acid salt cationic softeners.
The invention patent with the application number of CN201710578256.4 discloses an acrylic fiber softener and a preparation method thereof, wherein stearic acid and diethylenetriamine are reacted at 150-160 ℃ firstly, and then are reacted with hydroxyethylenediamine at 180-190 ℃ to generate a diamine modified cationic softener, which has better hydrophilicity and softness, but has higher price.
The invention patent with application number 201810443726.0 discloses a preparation process of a soft film of a softener, stearic acid and diethylenetriamine are reacted at 125-140 ℃ to obtain an intermediate I, the intermediate I is cooled to 75-85 ℃, epichlorohydrin is added dropwise, the temperature is raised to 125-140 ℃ after the dripping is finished, a secondary heat preservation reaction is carried out, the temperature is lowered to 75-85 ℃ after the reaction is finished, an intermediate II is obtained, glacial acetic acid is added to regulate the pH value, and the soft film of the softener is obtained after freezing and slicing, however, the hand feeling of the soft film is still to be improved.
The invention patent with the application number of CN200910105694.4 discloses a preparation method of a cationic fatty acid softener, which comprises the following steps: heating stearic acid to be molten, adding diethylenetriamine into the molten liquid of the stearic acid to obtain a mixed liquid of the diethylenetriamine and the stearic acid, and adding a catalyst into the mixed liquid to perform an amide condensation reaction; adding an alkylating reagent into the product of the amide condensation reaction to carry out alkylation reaction; adding a nonionic surfactant and polyvinylpyrrolidone into the product of the alkylation reaction, and cooling to obtain the cationic fatty acid softener. The softness is improved by adopting an alkylating reagent with stronger cation than acetic acid; polyvinyl pyrrolidone is added to improve whiteness; and a nonionic surfactant is used in the preparation process, so that the prepared softener can be used together with an anionic auxiliary agent in a same bath, the defects of the prior art are overcome, and the cationic fatty acid soft sheet softener with good hand feeling, high whiteness and low yellowing is obtained.
The invention comprises the following steps:
the invention aims to overcome the defects of the prior art, and seeks to design a diamine modified cationic film and a preparation method thereof, wherein the diamine modified cationic film has better hand feeling than a common film, is soft and has improved bulk, and can obtain a new hand feeling, and the finished fabric has unique fine and smooth sense and soft waxy sense, so that comfortable experience is brought to people.
In order to achieve the above purpose, the preparation method of the diamine modified cationic film according to the invention specifically comprises the following steps:
(1) Heating 500-700g stearic acid to 100 ℃ for melting, adding 18-28g 2,2' -dihydroxydiethylamine and 8-10g p-toluenesulfonic acid after the solid stearic acid is completely melted, introducing nitrogen for protection, opening reflux condensed water, starting stirring, and heating to 180-200 ℃ for reaction for 2-4h;
(2) And (3) cooling the reaction product obtained in the step (1) to 85-100 ℃ to start dripping diethylenetriamine, controlling the dripping temperature to 100-120 ℃, controlling the dripping amount of diethylenetriamine to 71-81g, controlling the dripping time to be within 1 hour, heating to 170 ℃ to perform constant temperature reaction for 6 hours after dripping is completed, sampling and analyzing the acid value, cooling to 100 ℃ to react for 60 minutes after 15-21g glacial acetic acid is added when the acid value is close to or reaches a theoretical value, and discharging and slicing.
Compared with the prior art, the invention has the following beneficial effects: (1) The adopted 2,2' -dihydroxydiethylamine and diethylenetriamine are environment-friendly products, so that the increasingly higher environmental protection requirements are met; (2) The diethylenetriamine is added dropwise, so that the diethylenetriamine can fully react with stearic acid, the content of free diethylenetriamine is reduced, the reaction rate of the diethylenetriamine and stearic acid is slowed down, the heat generated by the reaction is timely released, and the unstable system caused by suddenly generating a large amount of heat is avoided; (3) The p-toluenesulfonic acid plays a role of a catalyst and a protective agent, inhibits oxidation of raw materials and reduces yellowing; (4) Stearic acid reacts with 2,2' -dihydroxydiethylamine at 180-200 ℃ firstly, then reacts with diethylenetriamine at 100-120 ℃, and the softness, the fluffiness and the smoothness are improved by controlling the content of two cationic softeners, the addition amount of glacial acetic acid is controlled, and the softness is not influenced and meanwhile, the good hydrophilicity is ensured; (5) Stearic acid reacts with both amines, mixing the two different hand feel together to form a new hand feel that is more rich in layers.
The specific embodiment is as follows:
the invention is further described below by way of examples.
Example 1:
the preparation method of the diamine modified cationic film comprises the following steps:
(1) Heating 600g of stearic acid to 100 ℃ for melting, adding 23g of 2,2' -dihydroxydiethylamine and 9g of p-toluenesulfonic acid after the solid stearic acid is completely melted, introducing nitrogen for protection, opening reflux condensed water, starting stirring, and heating to 180-200 ℃ for reaction for 3 hours;
(2) And (3) cooling the reaction product obtained in the step (1) to 95 ℃ to start dripping diethylenetriamine, controlling the dripping temperature to be 100-120 ℃, controlling the dripping amount of diethylenetriamine to be 76g, controlling the dripping time to be within 1 hour, heating to 170 ℃ to perform constant temperature reaction for 6 hours after dripping is completed, sampling and analyzing the acid value, cooling to 100 ℃ to 18g glacial acetic acid to perform reaction for 60 minutes when the acid value is close to or reaches the theoretical value, and discharging and slicing.
Comparative example 1:
the preparation method of the diamine modified cationic film specifically comprises the following steps:
(1) Heating 400g of stearic acid to 100 ℃ for melting, cooling to 95 ℃ after the solid stearic acid is completely melted, starting dripping diethylenetriamine, controlling the dripping temperature to be 100-120 ℃, controlling the dripping amount of diethylenetriamine to be 76g, controlling the dripping time to be within 1 hour, heating to 170 ℃ for constant temperature reaction for 6 hours after the dripping is completed, sampling and analyzing the acid value, cooling to 100 ℃ for adding 18g of glacial acetic acid for reaction for 60 minutes when the acid value is close to or reaches a theoretical value, and discharging and slicing.
Comparative example 2:
the preparation method of the diamine modified cationic film comprises the following steps:
(1) Heating 600g of stearic acid to 100 ℃ for melting, adding 23g of 2,2' -dihydroxydiethylamine after the solid stearic acid is completely melted, introducing nitrogen for protection, opening reflux condensed water, starting stirring, and heating to 180-200 ℃ for reaction for 3 hours;
(2) And (3) cooling the reaction product obtained in the step (1) to 95 ℃ to start dripping diethylenetriamine, controlling the dripping temperature to be 100-120 ℃, controlling the dripping amount of diethylenetriamine to be 76g, controlling the dripping time to be within 1 hour, heating to 170 ℃ to perform constant temperature reaction for 6 hours after dripping is completed, sampling and analyzing the acid value, cooling to 100 ℃ to 18g glacial acetic acid to perform reaction for 60 minutes when the acid value is close to or reaches the theoretical value, and discharging and slicing.
The diamine modified cationic film prepared in example 1 and comparative examples 1 to 2 was subjected to performance test, and is specifically shown below.
(1) Viscosity test
Dissolving the above slice in water to obtain 10% solution, cooling to product standard required temperature (about 25deg.C), and adding into 300ml beaker; the level of the viscometer is regulated to enable the bubble of the level meter to be in the center, a clean rotor (the type of the rotor is selected according to the actual requirement of a product) is used for regulating the heights of the viscometer and the sample, so that the liquid level of the sample just submerges the scale mark of the rotor, after 20 seconds, the pointer is read after being stabilized (the pointer control rod is pressed down firstly during reading), and the viscosity is lower, and the use is convenient.
(2) Centrifugal stability
Diluting 10% diamine modified cationic film solution to 30g/L, loading into a centrifugal test tube, centrifuging at 3000r/min for 30min, standing to observe the state of the solution, and judging whether layering, aggregation, precipitation and the like occur.
| For 10 minutes | 20 minutes | 30 minutes | |
| Example 1 | Stabilization | Stabilization | Stabilization |
(3) Foam
Preparing 1000ml of 10% solution according to 25 g/L; placing the mixture in a constant-temperature water bath kettle, heating to 40 ℃, and controlling the temperature by a thermometer; the foam meter is preheated to 40 ℃, the foam meter is cleaned by clear water, then is rinsed by solution, and is read to zero (the bottom 250 ml). Transferring 200ml of solution, vertically dripping, discharging the solution, reading the foam height, and simultaneously pressing a stopwatch for timing; after 5 minutes, the foam height was again read.
| Concentration of auxiliary agent | Foam |
| Example 1 | 15-1 (bubble point foam height 15,5min after 1) |
(4) Assessment of hand feel
Preparing 600ml of 10g/L softener solution, weighing 600g (or 400 g) of ionized water, adding 3g of sample, uniformly stirring, adding 30g of fabric, immersing the fabric into the solution, treating for about 30 minutes at intervals, turning over the fabric, taking out, padding (the padding rate is about 80%), pre-drying at 80 ℃, and finally baking at 150 ℃. (in the process, the warp and weft of the cotton cloth are not damaged by pulling) the finished fabric is subjected to closed touch, 5-10 people are classified into a small group, the hand feeling is equally divided into 5 grades, and the higher the grade is, the softer the hand feeling is. Meanwhile, the whiteness is also classified into 5 grades, 5-10 people are classified into a group, and the whiteness is higher as the grade is higher.
The diamine softener is cationic in any medium, can obtain higher softness at a relatively lower application amount, has unique hand feeling, and is suitable for fabrics of various fibers.
Claims (2)
1. The preparation method of the diamine modified cationic film is characterized by comprising the following steps of:
(1) Heating 500-700g stearic acid to 100 ℃ for melting, adding 18-28g 2,2' -dihydroxydiethylamine and 8-10g p-toluenesulfonic acid after the solid stearic acid is completely melted, introducing nitrogen for protection, opening reflux condensed water, starting stirring, and heating to 180-200 ℃ for reaction for 2-4h;
(2) And (3) cooling the reaction product obtained in the step (1) to 85-100 ℃ to start dripping diethylenetriamine, controlling the dripping temperature to 100-120 ℃, controlling the dripping amount of diethylenetriamine to 71-81g, controlling the dripping time to be within 1 hour, heating to 170 ℃ to perform constant temperature reaction for 6 hours after dripping is completed, sampling and analyzing the acid value, cooling to 100 ℃ to react for 60 minutes after 15-21g glacial acetic acid is added when the acid value is close to or reaches a theoretical value, and discharging and slicing.
2. The diamine-modified cationic film produced by the production method of a diamine-modified cationic film according to claim 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202311349236.1A CN117449097A (en) | 2023-10-18 | 2023-10-18 | Diamine modified cationic film and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202311349236.1A CN117449097A (en) | 2023-10-18 | 2023-10-18 | Diamine modified cationic film and preparation method thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN117449097A true CN117449097A (en) | 2024-01-26 |
Family
ID=89593949
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202311349236.1A Pending CN117449097A (en) | 2023-10-18 | 2023-10-18 | Diamine modified cationic film and preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN117449097A (en) |
-
2023
- 2023-10-18 CN CN202311349236.1A patent/CN117449097A/en active Pending
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