CN110685151A - Anti-ultraviolet finishing agent with reaction activity and preparation method thereof - Google Patents

Anti-ultraviolet finishing agent with reaction activity and preparation method thereof Download PDF

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Publication number
CN110685151A
CN110685151A CN201810727778.0A CN201810727778A CN110685151A CN 110685151 A CN110685151 A CN 110685151A CN 201810727778 A CN201810727778 A CN 201810727778A CN 110685151 A CN110685151 A CN 110685151A
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ultraviolet
finishing agent
reactive
naphthol
tetrahydrofuran
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CN201810727778.0A
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张平
粟斯伟
蔡映杰
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Wuhan Textile University
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Wuhan Textile University
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    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322Treating 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
    • D06M13/35Heterocyclic compounds
    • D06M13/355Heterocyclic compounds having six-membered heterocyclic rings
    • D06M13/358Triazines
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D251/00Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12Heterocyclic 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
    • C07D251/26Heterocyclic 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
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2101/00Chemical constitution of the fibres, threads, yarns, fabrics or fibrous goods made from such materials, to be treated
    • D06M2101/02Natural fibres, other than mineral fibres
    • D06M2101/04Vegetal fibres
    • D06M2101/06Vegetal fibres cellulosic
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2200/00Functionality of the treatment composition and/or properties imparted to the textile material
    • D06M2200/25Resistance to light or sun, i.e. protection of the textile itself as well as UV shielding materials or treatment compositions therefor; Anti-yellowing treatments

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Abstract

The invention belongs to the technical field of textile chemistry, and particularly relates to an anti-ultraviolet finishing agent with reactivity and a preparation method thereof. The invention takes 2-naphthol and cyanuric chloride as main raw materials, realizes the reaction of the 2-naphthol and the cyanuric chloride in an alkali solution under the ice bath condition, and prepares the anti-ultraviolet finishing agent. The uvioresistant finishing agent can be applied to uvioresistant finishing of cellulose-containing fabrics, such as: cotton fabrics, hemp fabrics, and the like. The UPF value of the cotton fabric finished by the uvioresistant finishing agent can reach 69, which is 430% higher than that of the cotton fabric before finishing. The uvioresistant finishing agent has similar reactivity and stability as active dye, and the uvioresistant effect of cotton fabric after being washed for many times is still good.

Description

Anti-ultraviolet finishing agent with reaction activity and preparation method thereof
Technical Field
The invention belongs to the technical field of textile chemistry, and particularly relates to an anti-ultraviolet finishing agent with reactivity and a preparation method thereof.
Background
Ultraviolet rays are electromagnetic radiation, and the international commission on illumination (CIE) divides ultraviolet rays in solar radiation into 3 wavelength bands: (a) long-wavelength ultraviolet UV-A (wavelength is 315-400 nm), wherein the UV-A accounts for 90% of the total amount of the ultraviolet reaching the ground; (b) medium-wavelength ultraviolet UV-B (wavelength 290-315 nm), which is a source of sunburn of the skin; (c) short wavelength ultraviolet UV-C (wavelength 180-290 nm), ultraviolet can be absorbed by the ozone layer, can not reach the ground. In order to prevent ultraviolet rays from damaging human skin, people have begun to consider the ultraviolet resistance of fabrics and garments. The anti-ultraviolet finishing principle is that a fabric is applied with a material which can reflect or strongly and selectively absorb ultraviolet rays and can convert energy into heat energy or other harmless low-energy radiation.
At present, a small number of reports of cotton fabric uvioresistant agents are reported on the market, for example, patent application No. 201611068659.6 discloses a cotton fabric uvioresistant finishing agent of modified chitosan and an uvioresistant cotton fabric thereof, the cotton fabric uvioresistant finishing agent is a uniform mixture of 3, 4, 5-trimethoxybenzoyl chitosan, a cross-linking agent, a penetrating agent and an acetic acid or lactic acid solution, the uvioresistant finishing agent belongs to a compound product, and the raw material components of the uvioresistant finishing agent are complex. Patent application No. 201510631490.X discloses a black rice anthocyanin-based cotton fabric uv resistant finish, which comprises the following raw materials: the black rice anthocyanin extract, the organic polycarboxylic acid, the sodium citrate, the sodium sulfate and the penetrating agent, the components of the ultraviolet-resistant finishing agent are complex, and the ultraviolet-resistant mechanism is not clear. According to the anti-ultraviolet finishing principle, the invention provides and prepares the anti-ultraviolet finishing agent with reactivity, and the anti-ultraviolet finishing agent can effectively absorb ultraviolet rays, thereby achieving the purpose of resisting ultraviolet rays of fabrics. In addition, the uvioresistant finishing agent has the same reactivity as that of reactive dye, can chemically react with cellulose, and can keep stable uvioresistant performance after being washed for many times.
Disclosure of Invention
The fabric containing cellulose is widely applied, such as cotton fabric, polyester-cotton blended fabric, hemp fabric and the like, contains a large amount of cellulose, the cellulose contains a large amount of hydroxyl and has strong reaction activity, and the anti-ultraviolet finishing agent prepared by the invention can effectively perform chemical reaction with the hydroxyl of the cellulose, so that the anti-ultraviolet performance of the fabric is improved. In order to achieve the first object of the present invention, the inventors have conducted extensive experimental studies to develop a reactive uv-resistant finishing agent which is applied to uv-resistant finishing of cellulose-containing fabrics. The structural formula of the reactive ultraviolet resistant finishing agent is as follows:
Figure BDA0001720117860000021
another object of the present invention is to provide a method for preparing the reactive ultraviolet resistant finishing agent, wherein the method comprises the following steps:
under the ice bath condition, adding a proper amount of 2-naphthol into a three-neck flask filled with 50-100mL of tetrahydrofuran, dissolving a proper amount of cyanuric chloride and 5-10g of potassium carbonate into 30-100mL of tetrahydrofuran to obtain a mixed solution, then dropwise adding the mixed solution into the three-neck flask filled with 2-naphthol within a certain time, continuing stirring and reacting for a period of time after dropwise adding is finished, removing the tetrahydrofuran solvent in the reaction solution by using a rotary evaporator, washing the reaction product for multiple times by using deionized water, and finally drying the product under a certain condition to obtain the anti-ultraviolet finishing agent with reaction activity.
Further, the mass ratio of the 2-naphthol to the cyanuric chloride in the technical scheme is 1: 0.2-1.
Further, in the technical scheme, the dripping time is 1-3h, and the time for continuously stirring and reacting after the dripping is finished is 2-3 h.
Further, the drying conditions in the above technical scheme are as follows: vacuum drying at 30-50 deg.C for 10-20 hr.
The preparation method of the reactive ultraviolet resistant finishing agent of the invention relates to the following chemical reactions:
Figure BDA0001720117860000022
compared with the prior art, the invention has the following beneficial effects:
(1) the anti-ultraviolet finishing agent disclosed by the invention is simple in preparation process, convenient to use and obvious in anti-ultraviolet effect.
(2) The anti-ultraviolet finishing agent has similar reactivity with reactive dye, and the UPF value of the cotton fabric finished by the anti-ultraviolet finishing agent can reach 69; after the cotton fabric is washed for many times, the anti-ultraviolet effect is still good.
Detailed Description
The present invention will be described in detail with reference to specific embodiments in order to make those skilled in the art better understand the technical solutions of the present invention.
Example 1:
under the ice bath condition, adding 1g of 2-naphthol into a three-neck flask containing 50mL of tetrahydrofuran, dissolving 0.5g of cyanuric chloride and 5g of potassium carbonate into 100mL of tetrahydrofuran to obtain a mixed solution, then dropwise adding the 100mL of tetrahydrofuran mixed solution into the three-neck flask containing 50mL of tetrahydrofuran within 2h, continuing stirring and reacting for 2h after dropwise adding is finished, removing the tetrahydrofuran solvent in the reaction solution by a rotary evaporator, washing the reaction product for multiple times by deionized water, and finally drying the product under certain conditions to obtain the anti-ultraviolet finishing agent a with reaction activity.
Example 2:
under the ice bath condition, adding 1g of 2-naphthol into a three-neck flask containing 50mL of tetrahydrofuran, dissolving 1g of cyanuric chloride and 5g of potassium carbonate into 100mL of tetrahydrofuran to obtain a mixed solution, then dropwise adding the 100mL of tetrahydrofuran mixed solution into the three-neck flask containing 50mL of tetrahydrofuran within 3h, continuing stirring and reacting for 3h after dropwise adding is finished, removing the tetrahydrofuran solvent in the reaction solution by using a rotary evaporator, washing the reaction product for multiple times by using deionized water, and finally drying the product under certain conditions to obtain the anti-ultraviolet finishing agent b with reaction activity.
Example 3:
under the ice bath condition, 1g of 2-naphthol is added into a three-neck flask filled with 50mL of tetrahydrofuran, 0.8g of cyanuric chloride and 5g of potassium carbonate are dissolved in 100mL of tetrahydrofuran to obtain a mixed solution, then the 100mL of tetrahydrofuran mixed solution is dripped into the three-neck flask filled with 50mL of tetrahydrofuran within 3h, stirring and reacting are continued for 3h after dripping is finished, a rotary evaporator is used for removing the tetrahydrofuran solvent in the reaction solution, the reaction product is washed with deionized water for multiple times, and finally the product is dried under certain conditions to obtain the anti-ultraviolet finishing agent c with reaction activity.
The anti-ultraviolet performance test is carried out on the anti-ultraviolet finishing agents a, b and c with reactivity, which are prepared by the invention:
(1) carrying out anti-ultraviolet finishing on the cotton fabric: weighing 2g of cotton fabric and 0.3g of anti-ultraviolet finishing agent, placing the cotton fabric and the anti-ultraviolet finishing agent in 100mL of water for reaction, firstly adding 4g of sodium chloride, and reacting for 20min at normal temperature; then adding 1g of sodium carbonate, heating to 60 ℃, reacting for 1h, and finally washing and drying. And respectively carrying out anti-ultraviolet finishing on the cotton fabrics by using the anti-ultraviolet finishing agents a, b and c to obtain three cotton fabrics which are finished by the anti-ultraviolet finishing agents a, b and c, and then testing the anti-ultraviolet performance of the three cotton fabrics.
(2) And (3) testing ultraviolet resistance: according to the standard of the sunlight ultraviolet protection performance of EU textiles, RrEN13758-2001, an HB902 ultraviolet transmittance tester is adopted, the ultraviolet protection coefficient (UPF value) and the ultraviolet transmittance of the textiles are measured within the range of 250-450nm, each sample is tested for 3 times, and the average value is taken. The smaller the transmittance is, the larger the UPF value is, and the better the ultraviolet-proof effect is. And respectively measuring the UPF value of the cotton fabric which is finished by the anti-ultraviolet finishing agents a, b and c. The test results are shown in table 1:
TABLE 1 results of evaluation of UV resistance of reactive UV-resistant finishing agents a, b, c for cotton fabrics in examples 1-3
Figure BDA0001720117860000031
Figure BDA0001720117860000041
The higher the UPF value, the better the UV resistance of the fabric. As can be seen from table 1: the UPF value of the cotton fabric finished by the anti-ultraviolet finishing agents a, b and c is obviously improved, which shows that the anti-ultraviolet finishing agents a, b and c have good anti-ultraviolet finishing performance on the cotton fabric.
After the cotton fabrics finished by the anti-ultraviolet finishing agents a, b and c are washed by water for multiple times, the anti-ultraviolet effect of the cotton fabrics is evaluated, and the results are shown in a table 2:
table 2 examples 1-3 evaluation results of uv resistance of reactive uv-resistant finishing agents a, b, c to cotton fabrics after finishing and multiple washings
Number of washes Unfinished samples Finish a Finishing agent b Finishing agent c
5 12.4 58.1 65.4 68.9
10 12.1 57.6 64.1 67.1
20 11.9 56.2 63.3 66.2
As can be seen from Table 2, the UPF value of the cotton fabric is not reduced after 5 times, 10 times and 20 times of washing, which indicates that the uvioresistant performance of the cotton fabric is not reduced after multiple times of washing.
Finally, it should be noted that the above-mentioned description is only a preferred embodiment of the present invention, and those skilled in the art can make various similar representations without departing from the spirit and scope of the present invention.

Claims (5)

1. A reactive UV-resistant finish, characterized by: the structural formula of the reactive ultraviolet resistant finishing agent is as follows:
Figure FDA0001720117850000011
2. a process for the preparation of a reactive uv-resistant finish according to claim 1, characterized in that: the method comprises the following steps:
under the ice bath condition, adding a proper amount of 2-naphthol into a three-neck flask filled with 50-100mL of tetrahydrofuran, dissolving a proper amount of cyanuric chloride and 5-10g of potassium carbonate into 30-100mL of tetrahydrofuran to obtain a mixed solution, then dropwise adding the mixed solution into the three-neck flask filled with 2-naphthol within a certain time, continuing stirring and reacting for a period of time after dropwise adding is finished, removing the tetrahydrofuran solvent in the reaction solution by using a rotary evaporator, washing the reaction product for multiple times by using deionized water, and finally drying the product under a certain condition to obtain the anti-ultraviolet finishing agent with reaction activity.
3. The process for preparing a reactive UV-resistant finish according to claim 2, characterized in that: the mass ratio of the 2-naphthol to the cyanuric chloride is 1: 0.2-1.
4. The process for preparing a reactive UV-resistant finish according to claim 2, characterized in that: the dripping time is 1-3h, and the time for continuously stirring and reacting after the dripping is finished is 2-3 h.
5. The process for preparing a reactive UV-resistant finish according to claim 2, characterized in that: the drying conditions are as follows: vacuum drying at 30-50 deg.C for 10-20 hr.
CN201810727778.0A 2018-07-05 2018-07-05 Anti-ultraviolet finishing agent with reaction activity and preparation method thereof Pending CN110685151A (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112593402A (en) * 2020-12-14 2021-04-02 江南大学 Anti-ultraviolet and anti-oxidation finishing agent and preparation method and application thereof

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1250829A (en) * 1998-10-12 2000-04-19 王志 Compound for printing and dyeing
US6800757B2 (en) * 2001-09-27 2004-10-05 Cytec Technology Corp. Red-shifted triazine ultravioletlight absorbers
CN101250164A (en) * 2007-02-25 2008-08-27 中国科学院化学研究所 Water-soluble triazine derivatives as well as preparation method and uses thereof
CN107237143A (en) * 2017-07-10 2017-10-10 南通纺织丝绸产业技术研究院 A kind of uvioresistant soft finishing agent for textile, preparation method and applications
CN107988801A (en) * 2017-12-31 2018-05-04 南通纺织丝绸产业技术研究院 A kind of response type uvioresistant soft finishing agent and preparation method for cotton fabric

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1250829A (en) * 1998-10-12 2000-04-19 王志 Compound for printing and dyeing
US6800757B2 (en) * 2001-09-27 2004-10-05 Cytec Technology Corp. Red-shifted triazine ultravioletlight absorbers
CN101250164A (en) * 2007-02-25 2008-08-27 中国科学院化学研究所 Water-soluble triazine derivatives as well as preparation method and uses thereof
CN107237143A (en) * 2017-07-10 2017-10-10 南通纺织丝绸产业技术研究院 A kind of uvioresistant soft finishing agent for textile, preparation method and applications
CN107988801A (en) * 2017-12-31 2018-05-04 南通纺织丝绸产业技术研究院 A kind of response type uvioresistant soft finishing agent and preparation method for cotton fabric

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112593402A (en) * 2020-12-14 2021-04-02 江南大学 Anti-ultraviolet and anti-oxidation finishing agent and preparation method and application thereof
CN112593402B (en) * 2020-12-14 2022-03-04 江南大学 Anti-ultraviolet and anti-oxidation finishing agent and preparation method and application thereof

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