CN106521969B - A kind of fabric flame-retardant agent and its preparation method and application - Google Patents
A kind of fabric flame-retardant agent and its preparation method and application Download PDFInfo
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- CN106521969B CN106521969B CN201611029451.3A CN201611029451A CN106521969B CN 106521969 B CN106521969 B CN 106521969B CN 201611029451 A CN201611029451 A CN 201611029451A CN 106521969 B CN106521969 B CN 106521969B
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- organic solvent
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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
- 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
- D06M15/667—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing phosphorus in the main chain
- D06M15/673—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing phosphorus in the main chain containing phosphorus and nitrogen in the main chain
-
- 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
- C08G79/00—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule
- C08G79/02—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule a linkage containing phosphorus
- C08G79/04—Phosphorus linked to oxygen or to oxygen and carbon
-
- 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
- D06M16/00—Biochemical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. enzymatic
-
- 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
- D06M2200/30—Flame or heat resistance, fire retardancy properties
Abstract
The invention discloses a kind of fabric flame-retardant agent and its preparation method and application, which has following chemical structural formula：In structural formula：N=10~100；R1For H, C1‑6Aliphatic saturated hydrocarbon and C2‑6One kind in unsaturated alkyl；R2For H, C1‑6Aliphatic saturated hydrocarbon and C2‑6One kind in unsaturated alkyl.Fire retardant of the present invention can have both sterilization and anti-yellowing function while fire-retardant, realize that multifunction, the present invention prepare biological material used and be easy to get, natural reproducible, it is not petrochemical material, there is apparent advantage in cost, it may have highly important environmental protection and circular economy meaning.
Description
【Technical field】
The present invention relates to a kind of fabric flame-retardant agent and its preparation method and application more particularly to a kind of biology base antibacterial, resist
Xanthochromia contains N, P Type of Collective object fabric flame-retardant agent and its preparation method and application, belongs to finishing functions of textile fabrics technical field.
【Background technology】
High molecular material has lot of superiority energy, is widely used in the necks such as weaving, electronics, machinery, chemical industry, aerospace
Domain.With the enhancing of raising and disaster reduction and prevention theory that people realize fire disasters protection, flame-retardancy requirements of the people to material
It is more and more high, make the development of fire retardant, production and promote and apply to be rapidly developed, the kind of fire retardant increases increasingly, yield
It steeply rises.
Usually there are two types of modes for the preparation of flame retardant textiles, and one is addition types, i.e., mix fire retardant with spinning solution,
So that spun fabric has flame retardant property.Another kind is final finishing type, i.e., carries out flame-proof treatment to fabric.Current fabric resistance
Combustion agent can be divided into inorganic combustion inhibitor, halogen flame, phosphorus flame retardant, nitrogen-phosphorus flame retardant, also known as expansion type flame retardant.
The main harm of halogenated flame retardant is：When discarded burning, it is rotten that a large amount of dense smokes and dioxin, benzene furans etc. can be discharged
Corrosion toxic gas, these smog and gas have prodigious toxicity, may induce various diseases, and have strong carcinogenicity, right
The pollution of environment is larger.Halogenated flame retardant has gradually been used by limitation at present.Inorganic flame retardant have safety it is good, it is nontoxic,
Effect on environment is small, wide application and the advantages that abundant raw material, and portion increasingly increases on the market.But inorganic flame retardant
Especially aluminium compound fire retardant cannot play the role of preferable in the polymer, it is necessary to by a large amount of filling, can just play
Flame retardant effect, to affect the performance of material.The better heat stability of phosphorus flame retardant, not volatile, toxicity is low, to environment
Influence small, but red phosphorus combustion inhibitor will produce a certain amount of toxic gas when heated, keep the product color of gained deeper.Perhaps
It is halogen-free in more Intumescent Retardant Systems, when the classification material or product heated combustion of fire retardant, only releases a small amount of cigarette, and Halogen
Change the poison gases such as hydrogen to release.Expansion type flame retardant for high molecular material will be as current fire retardant research field the most active
One of, it is using nitrogen, phosphorus as a big based flame retardant of ignition-proof element, it can be avoided by the synergistic effect between nitrogen P elements
Using antimony as synergist, the use of halogens can also be avoided, is a kind of environmentally friendly fire proofing, is to hinder now
Fire the emphasis of agent research and development.
On the other hand, fabric-treating agent domestic at present can be only done washing, softness, low bacterium, low-yellowing, fire-retardant etc. mostly
, there is the problems such as having a single function, efficiency is low, of high cost, time-consuming, and waste discharge amount is big, and environmental pollution is serious in a certain item function,
This proposes to build a resource-conserving and environment-friendly society inconsistent with country.In view of expansion type flame retardant is mostly nitrogenous
Phosphoric acid ester substance, in addition, the substance of some low-yellowings be also some contain nitrogen compound, some have sterilization substances
It is some compounds of class containing ammonium.It can be realized so if some introduce fire retardant with low-yellowing and the nitrogen-containing group of bactericidal effect
The multifunction of fire retardant.Suchization can substantially reduce the cost of fabric treating, reduce the degree of environmental pollution.
It is support that the development of human material's civilization at present, which is to consume non-renewable resources on the earth,.It is tellurian can not
Regenerated resources limited amount, the period of formation are very long and it is just disappeared with the speed that is getting faster.In addition, excessively use can not be again
The series of problems such as energy crisis, environmental pollution and climatic variation are brought to the whole world in production-goods source.It finds new resources and realizes
It efficiently has become current governmental and the very urgent missions and goals of academia with clean using technology.Many institute's weeks
Know, tellurian biomass resource quantity is very huge and can be constantly regenerating, main component C, and H, O are also modernization
Learn conversion or most frequently used three kinds of elements in industry.As can either for bio-fuel by biomass resource Efficient Conversion
The starting material that can be utilized by chemical industry, biomass resource will play the part of even more important role in human resource structure.Cause
This prepares various chemicals from biomass and has become the important means that biomass resource efficiently utilizes, and countries in the world all will
The strategic plan important as its of Developing Biomass Chemical Engineering Technology simultaneously puts into a large amount of manpower and is researched and developed with material resources.
【Invention content】
It is of the existing technology the purpose of the invention is to overcome the problems, such as, a kind of raw material is provided and is easy to get, is at low cost, is had
There is reproducible biology base to realize the intumescent fabric flame-retardant agent for having both sterilization and low-yellowing.
It is another object of the present invention in order to provide the preparation method of the fire retardant.
Third object of the present invention is to provide a kind of applications of the fire retardant
The present invention uses following scheme：
A kind of fabric flame-retardant agent, it is characterised in that the fire retardant has following chemical structural formula：
In structural formula：N=10~100；
R1For H, C1-6Aliphatic saturated hydrocarbon and C2-6One kind in unsaturated alkyl；
R2For H, C1-6Aliphatic saturated hydrocarbon and C2-6One kind in unsaturated alkyl.
A kind of preparation method of above-mentioned fabric flame-retardant agent, it is characterised in that including step in detail below：
(1) in organic solvent,With R2NHNHR1Reaction generates
(2) in organic solvent, makeWith
It reacts and generates in the presence of reducing agent
R wherein in step (1) and (2)1For H, C1-6Aliphatic saturated hydrocarbon and C2-6One kind in unsaturated alkyl, R2For H,
C1-6Aliphatic saturated hydrocarbon and C2-6One kind in unsaturated alkyl；N=10~100.
In the step of preparation method of the present invention (1), it is methanol that organic solvent, which is organic solvent, ethyl alcohol, dichloromethane, 1,
2- dichloroethanes, one or more of tetrahydrofuran, ether, toluene and acetone are described
And R2NHNHR1Molar ratio be 1：1~1：10, organic base and R2NHNHR1Molar ratio be 1：1~1：10, reaction temperature 20
DEG C~160 DEG C of reaction time are 0.5~20 hour.
In the step of preparation method of the present invention (2), it is methanol that organic solvent, which is organic solvent, ethyl alcohol, dichloromethane, 1,
2- dichloroethanes, one or more of tetrahydrofuran, ether, toluene and acetone,
WithMolar ratio be 1：1~1：10, reaction temperature is 0~80 DEG C, the reaction time 0.5
~20 hours.
The present invention can increase the step of vacuum distillation removes organic solvent after step (1) and step (2) reaction.
A kind of application of above-mentioned fire retardant on the fabric, is especially being sterilized in fabric, low-yellowing is answered with fire-retardant aspect
With.
The application of above-mentioned fire retardant on the fabric, specific amount of flame-retardant agent be 170-230 grams per liter dressing liquids, preferably 200
The pH value of grams per liter dressing liquid, the dressing liquid is 7-8.
In conclusion beneficial effects of the present invention：
Fire retardant of the present invention can have both sterilization and anti-yellowing function while fire-retardant, realize multifunction, the present invention
It prepares biological material used to be easy to get, natural reproducible is not petrochemical material, has apparent advantage in cost, it may have
Highly important environmental protection and circular economy meaning.
【Specific implementation mode】
Fire retardant of the present invention is that it is as follows to prepare synthetic route containing N, P Type of Collective object fabric flame-retardant agents：
First step reaction of the present invention is an exothermic reaction：It willIt is added to containing organic molten
Agent and R2NHNHR1Mixed solution in, then continue at 20 DEG C~120 DEG C, preferably 40-80 DEG C heat preservation 0.5-20 hours, it is excellent
It is selected as 5-10 hours, then vacuum distillation removes organic solvent and obtainsWherein
Organic solvent is methanol, ethyl alcohol, dichloromethane, 1,2- dichloroethanes, one kind in tetrahydrofuran, ether, toluene and acetone or
It is several, preferred alcohol.
In the step (2),WithIt is mixed in organic solvent at 0 DEG C~80 DEG C, preferably 20-50 DEG C of reaction temperature, You Jirong
Agent is methanol, ethyl alcohol, dichloromethane, 1,2- dichloroethanes, one or more of tetrahydrofuran, ether, toluene and acetone,
One or both of preferred alcohol, dichloromethane stir 0.5-20 hours, preferably 4-15 hours.Then it is evaporated under reduced pressure organic
Solvent obtains
With reference to specific embodiment, the invention will be further described：
Embodiment 1：
(1) equipped with blender, in 2 liters of four round flask of thermometer and dropping funel,
It is added at room temperature containing organic solvent and NH2NH2.H2In O solution, then at 20~160 DEG C, under preferably 78 DEG C of reaction temperatures
Continue heat preservation 8 hours, then vacuum distillation removes organic solvent and obtainsIt is organic
Solvent is methanol, ethyl alcohol, dichloromethane, 1,2- dichloroethanes, one kind or several in tetrahydrofuran, ether, toluene and acetone
Kind, preferred alcohol.
In the step (2),With
It is mixed in organic solvent at 20 DEG C, 0 DEG C~80 DEG C, is stirred 10 hours preferably at 60 DEG C.Then it is evaporated under reduced pressure organic molten
Agent obtainsOrganic solvent is methanol, ethyl alcohol, two
Chloromethanes, 1,2- dichloroethanes, one or more of tetrahydrofuran, ether, toluene and acetone, preferred alcohol.
Its physical constant of resulting polymers is：1H NMR(400MHz,CDCl3)δ5.3-5.1(m,2H),5.07(s,8H),
432-4.18 (m, 2H), 2.67 (dr, 4H) infrared spectrums (KBr tablettings)：3350,2946,1658,1430,918,824cm-1。
Elemental analysis calculated value:C,29.47；H,4.95；N,12.50；Measured value:C,29.36；H,4.83；N,12.37.
Embodiment 2：
It (1), will in 2 liters of four round flask of thermometer and dropping funel equipped with blender
Be added at room temperature containing in organic solvent and MeNHNHMe solution, then at 20~160 DEG C, under preferably 78 DEG C of reaction temperatures after
Continuation of insurance temperature 8 hours, then vacuum distillation remove organic solvent and obtain
Wherein organic solvent is methanol, ethyl alcohol, dichloromethane, 1,2- dichloroethanes, one in tetrahydrofuran, ether, toluene and acetone
Kind or several, preferred alcohol.
It, will in the step (2)With
It is mixed in organic solvent at 20 DEG C in 20 DEG C, 0 DEG C~80 DEG C, stirs 10 hours preferably at 60 DEG C, be then evaporated under reduced pressure
Organic solvent obtainsOrganic solvent is first
Alcohol, ethyl alcohol, dichloromethane, 1,2- dichloroethanes, one or more of tetrahydrofuran, ether, toluene and acetone, preferably second
Alcohol.
Resulting polymers physical constant is：1H NMR(400MHz,CDCl3)δ5.3-5.1(m,2H),5.07(s,8H),
432-4.18(m,2H),3.01(s,6H),2.85(s,6H),2.67(dr,4H),.Infrared spectrum (KBr tablettings)：3527,
2919,1665,1428,928,806cm-1.Elemental analysis calculated value:C,35.79；H,5.81；N,11.13；Measured value:C,
35.64；H,5.76；N,11.28.
Embodiment 3：
It (1), will in 2 liters of four round flask of thermometer and dropping funel equipped with blender
Be added at room temperature containing in organic solvent and PhNHNHPh solution, then at 20~160 DEG C, under preferably 78 DEG C of reaction temperatures after
Continuation of insurance temperature 8 hours, then vacuum distillation remove organic solvent and obtainWherein
Organic solvent is methanol, ethyl alcohol, dichloromethane, 1,2- dichloroethanes, one kind in tetrahydrofuran, ether, toluene and acetone or
It is several, preferred alcohol.
It, will in the step (2)WithIn
It is mixed in organic solvent at 20 DEG C, 0 DEG C~80 DEG C, is stirred 10 hours preferably at 60 DEG C, be then evaporated under reduced pressure organic solvent
It obtainsOrganic solvent is methanol, ethyl alcohol,
Dichloromethane, 1,2- dichloroethanes, one or more of tetrahydrofuran, ether, toluene and acetone, preferred alcohol.
Its physical constant of resulting polymers is：1H NMR(400MHz,CDCl3)δ7.35-16(8,21H),：1H NMR
(400MHz,CDCl3)δ5.3-5.1(m,2H),5.07(s,8H),432-4.18(m,2H),2.67(dr,4H).Infrared spectrum
(KBr tablettings)：3541,2926,1670,1430,915,823cm-1.Elemental analysis calculated value:C,55.93；H,4.96；N,
7.45；Measured value:C,56.12；H,4.69；N,7.62.
Fire retardant obtained by Example 1-3 is made into dressing liquid by the dosage of 200 grams per liters, uses industry under agitation
Liquid caustic soda (30%) adjusts the pH value of dressing liquid to 7-8.Then it will pass through the nylon knitting object (100cm) of refining bleaching above-mentioned whole
Two leachings two are rolled in reason liquid, liquid carrying rate 90%, and 110 DEG C of preliminary dryings 2 minutes, 170 DEG C bake 2 minutes, obtain the cotton with flame retardant property
Cloth I-III.It is soft.The properties of flame-retardant textile are as shown in table 1-3：
Table 1：The variation of flame retardant property before and after the flame-proof treatment of fabric
Table 2：The variation of bacteriostasis property before and after the flame-proof treatment of fabric
Table 3：The variation of yellowing resistance energy before and after the flame-proof treatment of fabric
Fire retardant of the present invention is successful it can be seen from table 1-3 and significantly improves the flame retardant property of cotton fabric, biocidal property
Can and yellowing resistance energy, so that three kinds of effects is combined in an arranging process, simplify process, be greatly saved the production cycle and at
This.
Claims (5)
1. a kind of fabric flame-retardant agent, it is characterised in that the fire retardant has following chemical structural formula：
In structural formula：N=10-100；
R1For H, C1-6Aliphatic saturated hydrocarbon and C2-6One kind in unsaturated alkyl；
R2For H, C1-6Aliphatic saturated hydrocarbon and C2-6One kind in unsaturated alkyl.
2. a kind of preparation method of fabric flame-retardant agent described in claim 1, it is characterised in that including step in detail below：
(1) in organic solvent, in the presence of organic base, makeWith R2NHNHR1Reaction generates
(2) in organic solvent, makeWith
It reacts and generates in the presence of reducing agent
R wherein in step (1) and (2)1For H, C1-6Aliphatic saturated hydrocarbon and C2-6One kind in unsaturated alkyl, R2For H, C1-6It is full
With aliphatic hydrocarbon and C2-6One kind in unsaturated alkyl；N=10-100；
In step (1), the organic solvent be methanol, ethyl alcohol, dichloromethane, 1,2- dichloroethanes, tetrahydrofuran, ether,
One or more of toluene and acetone, the organic base are triethylamine, pyridine, diisopropyl ethyl amine, 4- dimethylaminos
Pyridine, one or more of N- methylmorpholines are describedAnd R2NHNHR1Molar ratio be
1：1~1：10, organic base and R2NHNHR1Molar ratio be 1：1~1：10, reaction temperature is 20 DEG C~160 DEG C, and the reaction time is
0.5~20 hour；
In step (2), the organic solvent be methanol, ethyl alcohol, dichloromethane, 1,2- dichloroethanes, tetrahydrofuran, ether,
One or more of toluene and acetone,With
Molar ratio be 1：1~1：10, reaction temperature is 0 DEG C~80 DEG C, and the reaction time is 0.5~20 hour.
3. a kind of preparation method of fabric flame-retardant agent according to claim 2, it is characterised in that step (1) and step (2)
Vacuum distillation removes organic solvent after reaction.
4. a kind of application of fire retardant described in claim 1 on the fabric.
5. a kind of application of fire retardant according to claim 4 on the fabric, it is characterised in that amount of flame-retardant agent 170-
The pH value of 230 grams per liter dressing liquids, the dressing liquid is 7-8.
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| CN201611029451.3A CN106521969B (en) | 2016-11-14 | 2016-11-14 | A kind of fabric flame-retardant agent and its preparation method and application |
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| CN106521969B true CN106521969B (en) | 2018-10-02 |
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Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
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| DE10241126A1 (en) * | 2002-09-03 | 2004-03-25 | Clariant Gmbh | Flame retardant-stabilizer combination for thermoplastic polymers |
| US8110695B2 (en) * | 2006-10-31 | 2012-02-07 | Welker Mark E | Compounds and compositions containing silicon and/or other heteroatoms and/or metals and methods of making and using them |
| CN101891896B (en) * | 2010-07-07 | 2012-08-22 | 安徽建筑工业学院 | Expansible fire retardant containing fluorine-phosphorus-nitrogen oligomer and preparation method thereof |
| CN102093566B (en) * | 2010-12-20 | 2013-03-20 | 安徽中鼎密封件股份有限公司 | Macromolecular intumescent flame retardant with phosphorus and nitrogen and synthesis method thereof |
| CN102225998A (en) * | 2011-04-19 | 2011-10-26 | 浙江科峰化工有限公司 | Preparation method for pentaerythritol phosphoryl triethanolamide |
| CN102260292B (en) * | 2011-05-13 | 2014-01-29 | 台州学院 | Flame retardant and preparation method thereof, and flame-retardant acrylate emulsion employing flame retardant |
| CN102731790A (en) * | 2012-07-10 | 2012-10-17 | 合肥工业大学 | Phosphorus-nitrogen-carbon intumescent flame retardant and preparation method thereof |
| CN103387673B (en) * | 2013-07-09 | 2015-12-23 | 上海交通大学 | Fire retardant and preparation method thereof and purposes |
| CN103981704B (en) * | 2014-05-23 | 2015-12-30 | 约克夏染料（中山）有限公司 | A kind of multifunctional fabric fire retardant and its preparation method and application |
| CN106478986B (en) * | 2016-08-26 | 2020-02-18 | 华南理工大学 | Environment-friendly flame retardant and preparation method and application thereof |
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