CN113638225B - Triazine ultraviolet-resistant finishing agent and preparation method thereof - Google Patents
Triazine ultraviolet-resistant finishing agent and preparation method thereof Download PDFInfo
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- CN113638225B CN113638225B CN202111114749.5A CN202111114749A CN113638225B CN 113638225 B CN113638225 B CN 113638225B CN 202111114749 A CN202111114749 A CN 202111114749A CN 113638225 B CN113638225 B CN 113638225B
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- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 title claims abstract description 31
- 238000002360 preparation method Methods 0.000 title abstract description 12
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 45
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims abstract description 38
- 150000001875 compounds Chemical class 0.000 claims abstract description 30
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 claims abstract description 28
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 claims abstract description 26
- ZXDDPOHVAMWLBH-UHFFFAOYSA-N 2,4-Dihydroxybenzophenone Chemical compound OC1=CC(O)=CC=C1C(=O)C1=CC=CC=C1 ZXDDPOHVAMWLBH-UHFFFAOYSA-N 0.000 claims abstract description 18
- CCJAYIGMMRQRAO-UHFFFAOYSA-N 2-[4-[(2-hydroxyphenyl)methylideneamino]butyliminomethyl]phenol Chemical compound OC1=CC=CC=C1C=NCCCCN=CC1=CC=CC=C1O CCJAYIGMMRQRAO-UHFFFAOYSA-N 0.000 claims abstract description 6
- 230000035484 reaction time Effects 0.000 claims abstract description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 84
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 72
- 238000006243 chemical reaction Methods 0.000 claims description 63
- 238000001816 cooling Methods 0.000 claims description 21
- 238000000967 suction filtration Methods 0.000 claims description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 16
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 14
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 12
- 239000000243 solution Substances 0.000 claims description 10
- 239000004753 textile Substances 0.000 claims description 8
- 239000000675 fabric finishing Substances 0.000 claims description 7
- 238000009962 finishing (textile) Methods 0.000 claims description 7
- 239000012224 working solution Substances 0.000 claims description 7
- 239000011780 sodium chloride Substances 0.000 claims description 6
- 230000000149 penetrating effect Effects 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 abstract description 3
- 238000003786 synthesis reaction Methods 0.000 abstract description 3
- CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 description 12
- 239000004744 fabric Substances 0.000 description 12
- 230000006750 UV protection Effects 0.000 description 11
- 238000010521 absorption reaction Methods 0.000 description 7
- 229920000742 Cotton Polymers 0.000 description 3
- 230000006378 damage Effects 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 3
- 239000002250 absorbent Substances 0.000 description 2
- 230000002745 absorbent Effects 0.000 description 2
- 239000006096 absorbing agent Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 208000000453 Skin Neoplasms Diseases 0.000 description 1
- 150000008378 aryl ethers Chemical class 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- 150000001565 benzotriazoles Chemical class 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- RSIPQHOWTCNEBI-UHFFFAOYSA-N n-hydroxypropanamide Chemical compound CCC(=O)NO RSIPQHOWTCNEBI-UHFFFAOYSA-N 0.000 description 1
- 230000004224 protection Effects 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 150000003870 salicylic acids Chemical class 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 201000000849 skin cancer Diseases 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000009988 textile finishing Methods 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 230000037303 wrinkles Effects 0.000 description 1
Images
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
- D06M2200/25—Resistance to light or sun, i.e. protection of the textile itself as well as UV shielding materials or treatment compositions therefor; Anti-yellowing treatments
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Abstract
The invention relates to a triazine ultraviolet-resistant finishing agent and a preparation method thereof, and the invention realizes the synthesis of a novel triazine ultraviolet-resistant finishing agent by controlling the molar ratio of cyanuric chloride to resorcinol, the molar ratio of a compound I to a compound 2,4-dihydroxy benzophenone, the molar ratio of a compound II to N-hydroxymethyl acrylamide and reaction time.
Description
Technical Field
The invention belongs to the field of textile chemical auxiliaries, and particularly relates to a triazine ultraviolet-resistant finishing agent and a preparation method thereof.
Background
The development of science and technology is better and better, the living standard of people is higher and higher, and the requirements on textiles are increased along with the development. However, with the destruction of the ozone layer, a large amount of ultraviolet radiation irradiates the ground, causing certain damage to the human body and even inducing skin cancer, which causes the requirements of people on the clothes textile to be increased from the initial covering, body protection and warm keeping to ultraviolet resistance, antibiosis and the like; therefore, the research on the ultraviolet resistant textile is particularly important.
The anti-ultraviolet finishing agent is attached to the textile by a chemical method, so that the textile has an anti-ultraviolet function; the ultraviolet-resistant finishing agent comprises an ultraviolet absorber and an ultraviolet screening agent. Examples of the ultraviolet absorber include triazines, benzophenones, benzotriazoles, and salicylic acids. Triazine ultraviolet absorbers are a new developed class of products that have a broad spectrum of ultraviolet resistance. Although triazine ultraviolet absorbers are in the development stage, the research thereof also has good prospects; for those skilled in the art, how to determine the optimal synthesis method to prepare the novel triazine ultraviolet-resistant finishing agent to improve the ultraviolet resistance of the fabric is the most critical issue.
Disclosure of Invention
In order to prevent the harm of ultraviolet rays to human bodies and improve the ultraviolet resistance of fabrics, the invention uses cyanuric chloride, resorcinol, 2,4-dihydroxy benzophenone and N-hydroxymethyl acrylamide to react according to the ultraviolet resistance mechanism of the triazine ultraviolet absorbent to generate the novel triazine ultraviolet absorbent.
One of the purposes of the invention is to provide a novel triazine uvioresistant finishing agent.
The second purpose of the invention is to provide a preparation method of the anti-ultraviolet finishing agent.
The invention also aims to provide the application of the uvioresistant finishing agent in the textile finishing process.
In order to realize the purpose of the invention, the following scheme is adopted:
the invention provides a triazine ultraviolet-resistant finishing agent, which has the structure as follows:
the invention provides a preparation method of the ultraviolet-resistant finishing agent, which comprises the following steps:
1) Adding cyanuric chloride and acetone solution into a reaction kettle with the water bath temperature of 45-60 ℃, adding anhydrous aluminum trichloride, and dropwise adding resorcinol dissolved in acetone into the reaction kettle; reacting at constant temperature for 5-8h, cooling to room temperature after the reaction is finished, performing suction filtration, and purifying to obtain a compound I;
2) Adding the compound I, acetone solution and sodium hydroxide into a reaction kettle with the water bath temperature of 60-80 ℃; adding 2,4-dihydroxy benzophenone dissolved in acetone into a reaction kettle; reacting at constant temperature for 5-8h, cooling to room temperature after the reaction is finished, performing suction filtration, and purifying to obtain a compound II;
3) Adding a compound II, an acetone solution and sodium hydroxide into a reaction kettle with a water bath temperature of 50-65 ℃; adding N-hydroxymethyl acrylamide dissolved in acetone into a reaction kettle; reacting at constant temperature for 5-8h, cooling to room temperature after the reaction is finished, performing suction filtration, and purifying to obtain the product.
Preferably, the molar ratio of the cyanuric chloride to the anhydrous aluminum trichloride in the step 1) is (1.1-2): 1.0; more preferably, the molar ratio is 1.1.
Preferably, the molar ratio of cyanuric chloride to resorcinol in step 1) is (0.8-1): 1.0, more preferably, the molar ratio is 1:1.
Preferably, the molar ratio of compound I to 2,4-dihydroxybenzophenone in step 2) is (0.75-1): 1; more preferably, the molar ratio is 1:1.
Preferably, the molar ratio of the compound II to the N-methylolacrylamide in the step 3) is 1 (3-4), more preferably, the molar ratio is 1:3.
Preferably, the reaction temperature in step 1) is 60 ℃.
Preferably, the reaction temperature in step 2) is 80 ℃.
Preferably, the reaction temperature in step 3) is 60 ℃.
Preferably, the reaction time in steps 1), 2) and 3) is 6h.
The invention also provides application of the ultraviolet-resistant finishing agent in ultraviolet-resistant finishing of textiles.
The invention also provides a fabric finishing working solution which comprises the anti-ultraviolet finishing agent.
Preferably, the fabric finishing working solution also contains a penetrating agent (penetrating agent JFC-1) and sodium chloride.
The invention also provides a preparation method of the fabric finishing working solution, which comprises the step of uniformly stirring and mixing the ultraviolet-resistant finishing agent, the penetrating agent and the sodium chloride prepared by the method.
By adopting the technical scheme, the invention has the following advantages:
the invention realizes the synthesis of the novel triazine ultraviolet-resistant finishing agent by controlling the molar ratio of cyanuric chloride to resorcinol, the molar ratio of the compound I to the compound 2,4-dihydroxy benzophenone, the molar ratio of the compound II to the N-hydroxymethyl acrylamide and the reaction time, has simple synthesis method and easily obtained raw materials, improves the ultraviolet resistance of fabrics and has good industrial production prospect.
Drawings
FIG. 1 is an infrared spectrum of the novel triazine ultraviolet resistant finishing agent prepared in example 5.
Detailed Description
The present invention is further described below in conjunction with examples, which are to be understood as being illustrative only and in no way limiting.
The experimental instruments in the invention are all conventional equipment in the field.
Except that the anti-ultraviolet finishing agent (innovation of the invention) is self-made, the materials and chemical reagents used in the invention can be purchased in the market.
The synthesis of the anti-ultraviolet finishing agent is completed by respectively replacing chlorine of cyanuric chloride with resorcinol and 2,4-dihydroxy benzophenone, opening double bonds in N-hydroxy propionamide to react with resorcinol, and comprises the following specific steps:
example 1
A preparation method of an anti-ultraviolet finishing agent comprises the following steps:
A. 3g of cyanuric chloride and 20ml of acetone are added into a reaction kettle with a water bath temperature of 60 ℃.
B. Adding anhydrous aluminum trichloride, wherein the molar ratio of cyanuric chloride to anhydrous aluminum trichloride is 1.1.
C. Slowly dripping resorcinol dissolved in 20ml of acetone into the reaction kettle, wherein the molar ratio of cyanuric chloride to resorcinol is 0.8:1.
D. reacting at constant temperature for 6h, cooling to room temperature after the reaction is finished, performing suction filtration, and purifying to obtain a compound I.
E. Adding 30ml of acetone, a compound I and sodium hydroxide into a reaction kettle with a water bath temperature of 80 ℃, wherein the molar ratio of the compound I to the sodium hydroxide is 1:3.
F. 2,4-dihydroxybenzophenone dissolved in 10ml acetone was added to the reaction kettle in a molar ratio of compound I to 2,4-dihydroxybenzophenone of 1:1.
G. Reacting at constant temperature for 6h, cooling to room temperature after the reaction is finished, performing suction filtration, and purifying to obtain a compound II.
H. In a reaction kettle with the water bath temperature of 60 ℃, 25ml of acetone, a compound II and sodium hydroxide are added, and the molar ratio of the compound II to the sodium hydroxide is 1:6.
I. N-methylolacrylamide dissolved in 15ml of acetone was added to the kettle in a molar ratio of 1:3 of compound II to N-methylolacrylamide.
J. Reacting for 6 hours at constant temperature, cooling to room temperature after the reaction is finished, performing suction filtration, and purifying to obtain the product.
Example 2
A preparation method of an anti-ultraviolet finishing agent comprises the following steps:
A. in a reaction kettle with a water bath temperature of 60 ℃, 3g of cyanuric chloride and 20ml of acetone solution are added.
B. Adding anhydrous aluminum trichloride, wherein the molar ratio of cyanuric chloride to anhydrous aluminum trichloride is 1.1.
C. Resorcinol dissolved in 20ml acetone was slowly added dropwise to the reactor in a molar ratio of cyanuric chloride to resorcinol of 1:1.
D. Reacting at constant temperature for 6h, cooling to room temperature after the reaction is finished, performing suction filtration, and purifying to obtain a compound I.
E. Adding 30ml of acetone, a compound I and sodium hydroxide into a reaction kettle with a water bath temperature of 80 ℃, wherein the molar ratio of the compound I to the sodium hydroxide is 1:3.
F. 2,4-dihydroxybenzophenone dissolved in 10ml acetone was added to the kettle in a molar ratio of compound i to 2,4-dihydroxybenzophenone of 1:1.
G. And (5) reacting at constant temperature for 6h, cooling to room temperature after the reaction is finished, performing suction filtration, and purifying to obtain a compound II.
H. In a reaction kettle with the water bath temperature of 60 ℃, 25ml of acetone, a compound II and sodium hydroxide are added, and the molar ratio of the compound II to the sodium hydroxide is 1:6.
I. N-methylolacrylamide dissolved in 15ml of acetone was added to the kettle in a molar ratio of 1:3 of compound II to N-methylolacrylamide.
J. Reacting for 6 hours at constant temperature, cooling to room temperature after the reaction is finished, performing suction filtration, and purifying to obtain the product.
Example 3
A preparation method of an anti-ultraviolet finishing agent comprises the following steps:
A. in a reaction kettle with a water bath temperature of 60 ℃, 3g of cyanuric chloride and 20ml of acetone solution are added.
B. Adding anhydrous aluminum trichloride, wherein the molar ratio of cyanuric chloride to anhydrous aluminum trichloride is 1.1.
C. Slowly dropwise adding resorcinol dissolved in 20ml of acetone into the reaction kettle, wherein the molar ratio of cyanuric chloride to resorcinol is 0.8:1.
D. reacting at constant temperature for 6h, cooling to room temperature after the reaction is finished, performing suction filtration, and purifying to obtain a compound I.
E. Adding 30ml of acetone, a compound I and sodium hydroxide into a reaction kettle with a water bath temperature of 80 ℃, wherein the molar ratio of the compound I to the sodium hydroxide is 1:3.
F. 2,4-dihydroxybenzophenone dissolved in 10ml acetone was added to the reaction kettle in a 0.75 molar ratio of compound i to 2,4-dihydroxybenzophenone.
G. Reacting at constant temperature for 6h, cooling to room temperature after the reaction is finished, performing suction filtration, and purifying to obtain a compound II.
H. In a reaction kettle with the water bath temperature of 60 ℃, 25ml of acetone, a compound II and sodium hydroxide are added, and the molar ratio of the compound II to the sodium hydroxide is 1:6.
I. N-methylolacrylamide dissolved in 15ml of acetone was added to the kettle in a molar ratio of 1:3 of compound II to N-methylolacrylamide.
J. Reacting for 6 hours at constant temperature, cooling to room temperature after the reaction is finished, performing suction filtration, and purifying to obtain the product.
Example 4
A preparation method of an anti-ultraviolet finishing agent comprises the following steps:
A. in a reaction kettle with a water bath temperature of 60 ℃, 3g of cyanuric chloride and 20ml of acetone solution are added.
B. Adding anhydrous aluminum trichloride, wherein the molar ratio of cyanuric chloride to anhydrous aluminum trichloride is 1.1.
C. Slowly and dropwise adding resorcinol dissolved in acetone into the reaction kettle, wherein the molar ratio of cyanuric chloride to resorcinol is 0.8.
D. Reacting at constant temperature for 6h, cooling to room temperature after the reaction is finished, performing suction filtration, and purifying to obtain a compound I.
E. Adding 30ml of acetone, a compound I and sodium hydroxide into a reaction kettle with a water bath temperature of 80 ℃, wherein the molar ratio of the compound I to the sodium hydroxide is 1:3.
F. 2,4-dihydroxybenzophenone dissolved in 10ml acetone was added to the reaction kettle in a molar ratio of compound I to 2,4-dihydroxybenzophenone of 1:1.
G. And (5) reacting at constant temperature for 6h, cooling to room temperature after the reaction is finished, performing suction filtration, and purifying to obtain a compound II.
H. In a reaction kettle with the water bath temperature of 60 ℃, 25ml of acetone, a compound II and sodium hydroxide are added, and the molar ratio of the compound II to the sodium hydroxide is 1:6.
I. N-methylolacrylamide dissolved in 15ml of acetone was added to the kettle in a molar ratio of 1:4 of compound II to N-methylolacrylamide.
J. Reacting for 6 hours at constant temperature, cooling to room temperature after the reaction is finished, performing suction filtration, and purifying to obtain the product.
Example 5
A preparation method of an anti-ultraviolet finishing agent comprises the following steps:
A. in a reaction kettle with a water bath temperature of 60 ℃, 3g of cyanuric chloride and 20ml of acetone solution are added.
B. Adding anhydrous aluminum trichloride, wherein the molar ratio of cyanuric chloride to anhydrous aluminum trichloride is 1.1.
C. Slowly and dropwise adding resorcinol dissolved in acetone into the reaction kettle, wherein the molar ratio of cyanuric chloride to resorcinol is 0.8.
D. And (5) carrying out constant temperature reaction for 7h, cooling to room temperature after the reaction is finished, carrying out suction filtration, and purifying to obtain a compound I.
E. Adding 30ml of acetone, a compound I and sodium hydroxide into a reaction kettle with a water bath temperature of 80 ℃, wherein the molar ratio of the compound I to the sodium hydroxide is 1:3.
F. 2,4-dihydroxybenzophenone dissolved in 10ml acetone was added to the reaction kettle in a molar ratio of compound I to 2,4-dihydroxybenzophenone of 1:1.
G. And (5) reacting at constant temperature for 7h, cooling to room temperature after the reaction is finished, performing suction filtration, and purifying to obtain a compound II.
H. In a reaction kettle with the water bath temperature of 60 ℃, 25ml of acetone, a compound II and sodium hydroxide are added, and the molar ratio of the compound II to the sodium hydroxide is 1:6.
I. N-methylolacrylamide dissolved in 15ml of acetone was added to the reactor in a molar ratio of compound II to N-methylolacrylamide of 1:3.
J. Reacting for 7 hours at constant temperature, cooling to room temperature after the reaction is finished, performing suction filtration, and purifying to obtain the product.
2. Fabric treatment process
The novel triazine uvioresistant finishing agent is finished on fabrics.
A. A piece of cotton cloth was taken and weighed.
B. The cotton cloth was put into the prepared triazine ultraviolet absorber finishing liquid (20% owf), and 2g/L of a penetrant JFC-1 was added thereto, followed by dipping at 40 ℃ for 0.5 hour.
C. Heating to 80 deg.C, adding 1/2 sodium chloride (18 g/L), reacting for 15min, adding the rest 1/2 sodium chloride (18 g/L), and reacting for 15min.
D. And (3) placing the finished fabric in an oven, and drying at the temperature of 100 ℃.
3. Performance evaluation test
Ultraviolet protection factor UPF: the assay is defined in reference GB/T18830-2009; wrinkle recovery: reference GB/T3819-1997; breaking strength: the assay was performed as specified in GB/T2392.1-2013.
TABLE 1 UV protection factor of triazine UV-resistant finishes of the invention
TABLE 2 Properties of the UV-resistant finish of the invention
From the IR spectrum of FIG. 1, it can be seen that 3215.71cm-1 is the characteristic absorption peak of-OH on the benzene ring, 3102.5cm-1 is the stretching vibration peak of C-H on the benzene ring, 1609.90cm-1 is the stretching vibration peak of C = O on the triazine ring, 1489.15cm-1 is the characteristic absorption peak of C = C on the benzene ring, 1382.35cm-1 is the stretching vibration peak of C = N on the triazine ring, 1220.54cm-1 is the characteristic absorption peak of C-O on the aromatic ether, 844.07cm-1 is the characteristic absorption peak of C-H on the aromatic ring, wherein the characteristic absorption peak of the ether bond and the characteristic absorption peak of the hydroxyl group are broadened, indicating that benzophenone reacts with cyanuric chloride. 1149.14cm-1 is the characteristic absorption peak for C-O-C, indicating that hydroxyl groups on the aromatic ring have reacted with N-methylol acrylamide.
The novel triazine uvioresistant finishing agent prepared by the invention has good uvioresistant effect, the UPF value can reach 40+, the requirement of uvioresistant fabrics is met, and the novel triazine uvioresistant finishing agent can absorb ultraviolet light of 280nm-400 nm. The invention is finished on cotton fabrics, endows the fabrics with ultraviolet resistance, has the ultraviolet resistance effect reaching the national standard, and meets the requirement of the ultraviolet resistance finishing agent for the fabrics.
The above embodiments are merely exemplary, and do not limit the scope of the present invention in any way. It will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope of the invention, and that such changes and substitutions are intended to be included within the scope of the invention.
Claims (10)
1. A triazine ultraviolet-resistant finishing agent is characterized in that: the structure is as follows:
2. the process for preparing triazine ultraviolet-resistant finishing agents as defined in claim 1, wherein: the method comprises the following steps:
1) Adding cyanuric chloride and acetone solution into a reaction kettle with the water bath temperature of 45-60 ℃, adding anhydrous aluminum trichloride, and dropwise adding resorcinol dissolved in acetone into the reaction kettle; reacting at constant temperature for 5-8h, cooling to room temperature after the reaction is finished, performing suction filtration, and purifying to obtain a compound I;
2) Adding the compound I, acetone solution and sodium hydroxide into a reaction kettle with the water bath temperature of 60-80 ℃; adding 2,4-dihydroxy benzophenone dissolved in acetone into a reaction kettle; reacting at constant temperature for 5-8h, cooling to room temperature after the reaction is finished, performing suction filtration, and purifying to obtain a compound II;
3) Adding a compound II, an acetone solution and sodium hydroxide into a reaction kettle with a water bath temperature of 50-65 ℃; adding N-hydroxymethyl acrylamide dissolved in acetone into a reaction kettle; reacting for 5-8h at constant temperature, cooling to room temperature after the reaction is finished, performing suction filtration, and purifying to obtain the product.
3. The method for preparing the triazine ultraviolet-resistant finishing agent according to claim 2, characterized in that: in the step 1), the molar ratio of the cyanuric chloride to the anhydrous aluminum trichloride is (1.1-2): 1.0.
4. the method for preparing the triazine ultraviolet-resistant finishing agent as claimed in claim 2, wherein the method comprises the following steps: the molar ratio of cyanuric chloride to resorcinol in step 1) (0.8-1) is 1.0.
5. The method for preparing the triazine ultraviolet-resistant finishing agent as claimed in claim 2, wherein the method comprises the following steps: the molar ratio of the compound I to the 2,4-dihydroxybenzophenone in step 2) is (0.75-1): 1.
6. the method for preparing the triazine ultraviolet-resistant finishing agent as claimed in claim 2, wherein the method comprises the following steps: the molar ratio of the compound II to the N-hydroxymethyl acrylamide in the step 3) is 1 (3-4).
7. The method for preparing the triazine ultraviolet-resistant finishing agent as claimed in claim 2, wherein the method comprises the following steps: the reaction temperature in the step 1) is 60 ℃; the reaction temperature in the step 2) is 80 ℃; the reaction temperature in the step 3) is 60 ℃; the reaction time in the steps 1), 2) and 3) is 6h.
8. Use of the triazine uv-resistant finishing agent of claim 1 for uv-resistant finishing of textiles.
9. A fabric finishing working solution is characterized in that: the fabric finishing working solution comprises the triazine ultraviolet-resistant finishing agent as defined in claim 1; the fabric finishing working solution also contains a penetrating agent and sodium chloride.
10. A method for preparing the fabric finishing working solution as defined in claim 9, which is characterized in that: the finishing agent is prepared by uniformly mixing the triazine ultraviolet-resistant finishing agent prepared by the method of any one of claims 2 to 7, a penetrating agent and sodium chloride.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111114749.5A CN113638225B (en) | 2021-09-23 | 2021-09-23 | Triazine ultraviolet-resistant finishing agent and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111114749.5A CN113638225B (en) | 2021-09-23 | 2021-09-23 | Triazine ultraviolet-resistant finishing agent and preparation method thereof |
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| US5741905A (en) * | 1994-07-23 | 1998-04-21 | Ciba Specialty Chemicals Corporation | Triazine ultraviolet absorbers useful for improving the sun protection factor of textiles |
| US6855269B2 (en) * | 2001-11-09 | 2005-02-15 | Cytec Technology Corp. | Phenyl ether-substituted hydroxyphenyl triazine ultraviolet light absorbers |
| JP2006052329A (en) * | 2004-08-12 | 2006-02-23 | Fuji Photo Film Co Ltd | Cellulose acylate film |
| JP2010260014A (en) * | 2009-05-08 | 2010-11-18 | Nippon Bee Chemical Co Ltd | Method of forming coating film to carbon fiber-reinforced plastics |
| CN105131174B (en) * | 2015-08-20 | 2017-04-05 | 广东德美精细化工股份有限公司 | It is common to lasting uvioresistant finishing agent of cotton and terylene and preparation method thereof |
| CN107237143B (en) * | 2017-07-10 | 2019-08-09 | 南通纺织丝绸产业技术研究院 | It is a kind of for the uvioresistant soft finishing agent of textile, preparation method and applications |
| CN107988801B (en) * | 2017-12-31 | 2020-04-21 | 南通纺织丝绸产业技术研究院 | Reactive ultraviolet-resistant softening finishing agent for cotton fabrics and preparation method thereof |
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| CN110761091B (en) * | 2019-10-29 | 2022-10-11 | 浙江理工大学上虞工业技术研究院有限公司 | Water-soluble cross-linking color fixing agent with ultraviolet absorption function and preparation method thereof |
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