CN106632941A - Efficient durable antistatic agent and preparation method thereof - Google Patents
Efficient durable antistatic agent and preparation method thereof Download PDFInfo
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- CN106632941A CN106632941A CN201611262448.6A CN201611262448A CN106632941A CN 106632941 A CN106632941 A CN 106632941A CN 201611262448 A CN201611262448 A CN 201611262448A CN 106632941 A CN106632941 A CN 106632941A
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- aqueous polyurethane
- graphene
- diisocyanate
- modified graphene
- agent
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4833—Polyethers containing oxyethylene units
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6666—Compounds of group C08G18/48 or C08G18/52
- C08G18/6692—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/34
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6666—Compounds of group C08G18/48 or C08G18/52
- C08G18/6696—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/36 or hydroxylated esters of higher fatty acids of C08G18/38
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/04—Polyurethanes
- C08L75/08—Polyurethanes from polyethers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/04—Antistatic
Abstract
The invention belongs to the field of fabric finishing, and discloses a preparation method of an efficient durable antistatic agent. The efficient durable antistatic agent is characterized by being modified graphene chemically-grafted modified waterborne polyurethane which is prepared from 0.5 to 5 percent of graphene and 95 to 99.5 percent of waterborne polyurethane. The product has excellent antistatic property, excellent washing resistance and abrasion resistance, is safe and non-toxic, enriches the variety of antistatic agents and broadens the application field of graphene.
Description
Technical field
The present invention relates to fabric post-treatment field, and in particular to a kind of preparation method of efficient durability electrostatic agent.
Background technology
Negative electrical charge can be produced after most of chemical ＆ blended fabric frictions, thus need to be arranged using antistatic additive, to guarantee to wear
The comfortableness and security, it is that pole is necessary that antistatic finish is carried out to fabric, and antistatic additive is the important fabric of a class
After-treating auxiliary.Cationic surface active agent has excellent antistatic effect, wherein based on quaternary, being widely used in
Synthetic fibers, but the relative molecular mass of this kind of antistatic additive is relatively low, and fiber surface reactive group is less, antistatic additive is difficult to
In fiber surface attachment, then fastness to washing is poor, fastness to rubbing is relatively low and right this kind of antistatic additive in practical application is had
The shortcomings of dyed fabric easily causes discoloration.The current polymer electrolyte antistatic finishing agent overwhelming majority is solvent-borne type finishing agent,
Have the shortcomings that to arrange high processing costs, easily cause environmental pollution.Current high-performance new varieties antistatic additive production capacity in a word
It is weak, it is of less types, can not still fully meet current needs.
Aqueous polyurethane is with environmental protection, without aldehyde, high performance advantage, and structure design-adjustable, excellent combination property is aqueous
Polyurethane can give fabric good elasticity as fabric finishing agent, soft and smooth feel, and current aqueous polyurethane is spinning
The existing more application in printing and dyeing assistant field is knitted, wherein can be used as antistatic additive.
Graphene is the new carbon that Novoselov and Andre Geim have found, with excellent physical chemistry
Performance, such as, with extremely strong electric conductivity, specific surface area of superelevation etc., have been carried out wide grinding with regard to Graphene at present
Study carefully, and application is realized in some fields, but research and application of the Graphene in terms of textile auxiliary is still less.
Chinese patent CN103469555A discloses a kind of preparation of ultraviolet-proof antistatic graphene coating weaving face fabric
Method, the method will be added in soluble polyurethane solution after graphene solution concussion dispersion, due to the water solubility of Graphene
It is poor, after strength concussion dispersion, precipitated and separated is easily produced, and also Graphene and soluble polyurethane are only physical blendings, it is resistance to
Washing and durability are poor.
The content of the invention
Object of the present invention is to provide a kind of preparation method of new and effective durable antistatic agent, solves prior art
Middle antistatic additive is of less types, and antistatic principle is single, antistatic less efficient, water-fastness, poor durability problem.
For achieving the above object, the present invention is adopted the following technical scheme that：
A kind of efficient durable antistatic agent, the antistatic additive is modified graphene grafting modification aqueous polyurethane, wherein stone
Black alkene accounts for 0.5% ~ 5%, and aqueous polyurethane accounts for 95% ~ 99.5%.
The efficient durable antistatic agent, modified graphene is obtained for graphene oxide modified with reduction.
The efficient durable antistatic agent, aqueous polyurethane is anionic and nonionic type aqueous polyurethane.
The efficient durable antistatic agent, aqueous polyurethane is Waterborne Blocked Polyurethane.
The efficient durable antistatic agent, the molecular weight of aqueous polyurethane is 20,000 ~ 60,000.
Described modified graphene grafting modification aqueous polyurethane, it is characterised in that using surface of graphene oxide hydroxyl
Base and NCO reaction in polyurethane, specifically include following steps：
（1）Hydroxyl polyol processed, under an inert atmosphere, diisocyanate and hydroxyl polyol is reacted 1～4 hour,
Hydrophilic chain extender reaction 0.5-2 hours are subsequently adding, addition proper amount of acetone adjusts viscosity, obtains base polyurethane prepolymer for use as；
（2）Graphene oxide is added, is reacted 1～2 hour under catalyst action, add sealer, reacted to after without NCO, plus
Enter a certain amount of reducing agent, react 2～6 hours, add in nertralizer and 10～30min, under high-speed stirred deionized water is added,
Vacuum distillation removes acetone, and Graphene chemical modification aqueous polyurethane is obtained.
Step（1）Described diisocyanate is selected from IPDI (IPDI), toluene di-isocyanate(TDI)
(TDI), '-diphenylmethane diisocyanate (MDI), hexamethylene diisocyanate (HDI), dicyclohexyl methyl hydride diisocyanate
(HMDI) one or more in.
Step（1）Described hydroxyl polyol is PEG400, Macrogol 600, polyethylene glycol-800, polyethylene glycol
1000th, one or more in polyethylene glycol 1500, polyethylene glycol 2000, Macrogol 3000, Macrogol 4000.
Step（1）Described hydrophilic chain extender is the one kind in dihydromethyl propionic acid, dimethylolpropionic acid.
Step（1）Described hydroxyl polyol, diisocyanate, the mol ratio of chain extender are 1:2～4:0.5～1.
Step（2）The fineness of described graphene oxide be 0.5 ~ 5um, purity ＞ 96%.
Step（2）Described catalyst is environment-friendly type organic bismuth catalyst.
Step（2）Described sealer is the one kind in sodium hydrogensulfite, diacetylmonoxime, phenol.
Step（2）Described reducing agent is the one kind in hydrazine hydrate, sodium borohydride, ethylenediamine.
Step（2）Described reducing agent is 1 ~ 3 with the mass ratio of graphene oxide:1.
Step（2）Described described nertralizer is the one kind in triethylamine, ammoniacal liquor, NaOH.
The advantages of the present invention are：
1st, while using the superior electrical conductivity and hygroscopicity two antistatic principles of conduction of aqueous polyurethane of Graphene, being more easy to carry
High-antistatic efficiency；
2nd, Graphene and aqueous polyurethane chemistry are bonded, with reference to more firm, are not likely to produce layering and precipitating phenomenon；
3rd, blocked polyurethane is adopted, the adhesion with fiber is improved, water-fastness, durable antistatic property is improved.
Specific embodiment
With reference to specific embodiment, the invention will be further described.Following examples are only used for clearly saying
Bright technical scheme, and can not be limited the scope of the invention with this.
Embodiment 1
By 100g cetomacrogol 1000 processeds, under an inert atmosphere, by 34.8g toluene di-isocyanate(TDI)s and polyethylene glycol
1000 react 4 hours at 60 DEG C, are subsequently adding 6.7g hydrophilic chain extenders dihydromethyl propionic acid and react 2 hours at 60 DEG C, addition
Proper amount of acetone adjusts viscosity, obtains base polyurethane prepolymer for use as, adds 0.7g graphene oxides, adds organic bismuth catalyst, and 60 DEG C anti-
Answer 1 hour, add 1.4g sodium hydrogensulfites, react to after without NCO, add 2.1g reducing agent hydrazine hydrates, continue to react 2 hours,
Add in nertralizer triethylamine and 10min, add deionized water, vacuum distillation removing acetone that modified stone is obtained under high-speed stirred
Black alkylene graft modified aqueous polyurethane antistatic additive.
Embodiment 2
By 100g cetomacrogol 1000 processeds, under an inert atmosphere, by 42g hexamethylene diisocyanates and polyethylene glycol
1000 react 4 hours at 60 DEG C, are subsequently adding 8g hydrophilic chain extenders dihydromethyl propionic acid and react 2 hours at 40 DEG C, and addition is suitable
Amount acetone adjusts viscosity, obtains base polyurethane prepolymer for use as, adds 1.5g graphene oxides, adds organic bismuth catalyst, 60 DEG C of reactions 1
Hour, add 1.5g diacetylmonoximes to react to after without NCO, 3g ethylenediamine reducing agents are added, continue to react 2 hours, add nertralizer
In NaOH and 20min, add deionized water, vacuum distillation removing acetone that modified graphene chemistry is obtained under high-speed stirred
Graft modified aqueous polyurethane antistatic additive.
Embodiment 3
By 50g polyethylene glycol 2000 processeds, under an inert atmosphere, by 22.3g IPDIs and poly- second two
Alcohol 2000 reacts 1 hour at 90 DEG C, is subsequently adding 3.7g hydrophilic chain extenders dimethylolpropionic acid and reacts 4 hours at 50 DEG C, adds
Plus proper amount of acetone adjusts viscosity, obtains base polyurethane prepolymer for use as, 3.8g graphene oxides are added, add organic bismuth catalyst, 50 DEG C
Reaction 2 hours, adds 0.76g phenol reactants to after without NCO, adds 1.52g reducing agents, continues to react 6 hours, adds nertralizer
In ammoniacal liquor and 30min, add deionized water, vacuum distillation removing acetone that modified graphene chemical graft is obtained under high-speed stirred
Modified aqueous polyurethane antistatic additive.
In order to be better understood by antistatic effect, detect that fabric is resistance polyester fiber knitting fabric, be the results are shown in Table by GB/T12703.1
1。
Finishing technique：Pad → dry（100℃）→ bake（160 DEG C, 1min）→ moisture regain → test → washing → drying
→ moisture regain → test
The each embodiment antistatic effect contrast of table 1
Find out from the data of table 1, embodiment gained antistatic additive is respectively provided with excellent antistatic property, and washes 10 times afterwards still
There is preferable antistatic property.
The preferred embodiments of the present invention are the foregoing is only, those skilled in the art enters in the range of technical solution of the present invention
Capable usual variations and alternatives all should be comprising within the scope of the present invention.
Claims (9)
1. a kind of efficient durable antistatic agent, it is characterised in that antistatic additive is that modified graphene grafting modification is aqueous poly-
Mass percent shared by urethane, wherein modified graphene is：0.5%~5%；Modified graphene is graphene oxide modified with reduction
It is obtained；Aqueous polyurethane is anionic and nonionic type aqueous polyurethane.
2. efficient durable antistatic agent according to claim 1, it is characterised in that aqueous polyurethane is the aqueous poly- ammonia of enclosed type
Ester, the molecular weight of aqueous polyurethane is 20,000 ~ 60,000.
3. the preparation method of efficient durable antistatic agent according to claim 1, using surface of graphene oxide hydroxyl with it is poly-
NCO reaction in urethane, it is characterised in that comprise the steps：
（1）Hydroxyl polyol processed, under an inert atmosphere, diisocyanate and hydroxyl polyol is reacted 1～4 hour,
Hydrophilic chain extender reaction 0.5-2 hours are subsequently adding, addition proper amount of acetone adjusts viscosity, obtains base polyurethane prepolymer for use as；
（2）Graphene oxide is added, is reacted 1～2 hour under catalyst action, add sealer, reacted to after without NCO, plus
Enter a certain amount of reducing agent, react 2～6 hours, add in nertralizer and 10～30min, under high-speed stirred deionized water is added,
Vacuum distillation removes acetone, and Graphene chemical modification aqueous polyurethane is obtained.
4. preparation method according to claim 3, it is characterised in that step（1）Described diisocyanate is selected from different Fo Er
Ketone diisocyanate (IPDI), toluene di-isocyanate(TDI) (TDI), '-diphenylmethane diisocyanate (MDI), the isocyanide of hexa-methylene two
One or more in acid esters (HDI), dicyclohexyl methyl hydride diisocyanate (HMDI).
5. modified graphene grafting modification aqueous polyurethane according to claim 4, it is characterised in that：Step（1）
Described hydroxyl polyol is PEG400, Macrogol 600, polyethylene glycol-800, cetomacrogol 1000, polyethylene glycol
1500th, one or more in polyethylene glycol 2000, Macrogol 3000, Macrogol 4000；Step（1）Described hydrophilic expansion
Chain agent is the one kind in dihydromethyl propionic acid, dimethylolpropionic acid.
6. modified graphene grafting modification aqueous polyurethane according to claim 3, it is characterised in that：Hydroxy polybasic
Alcohol, diisocyanate, the mol ratio of chain extender are 1:2～4:0.5～1；The fineness of graphene oxide be 0.5 ~ 5um, purity ＞
96%。
7. modified graphene grafting modification aqueous polyurethane according to claim 3, it is characterised in that：Catalyst is
Environment-friendly type organic bismuth catalyst, sealer is the one kind in sodium hydrogensulfite, diacetylmonoxime, phenol, and reducing agent is hydrazine hydrate, boron hydrogen
Change the one kind in sodium, ethylenediamine.
8. modified graphene grafting modification aqueous polyurethane according to claim 6, it is characterised in that：Reducing agent with
The mass ratio of graphene oxide is 1 ~ 3:1.
9. modified graphene grafting modification aqueous polyurethane according to claim 6, it is characterised in that：In described
It is the one kind in triethylamine, ammoniacal liquor, NaOH with agent.
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107501520A (en) * | 2017-09-22 | 2017-12-22 | 江苏多森化工有限公司 | A kind of antistatic treatment agent and preparation method thereof |
| CN108166095A (en) * | 2017-12-18 | 2018-06-15 | 浙江恒逸高新材料有限公司 | A kind of hydrophilic antistatic graphene Modified polyester chips and preparation method thereof |
| CN108642691A (en) * | 2018-07-05 | 2018-10-12 | 刘群英 | Antistatic fabric and preparation method thereof |
| CN108659199A (en) * | 2018-04-13 | 2018-10-16 | 中国皮革和制鞋工业研究院（晋江）有限公司 | Modified aqueous polyurethane dispersoid and preparation method thereof and vamp finishing agent |
| CN109944066A (en) * | 2019-04-08 | 2019-06-28 | 福建华彩新材料有限公司 | A kind of graphene anti-static fabric and preparation method thereof |
| WO2020215800A1 (en) * | 2019-04-26 | 2020-10-29 | 深圳先进技术研究院 | Polyurethane material, and preparing method therefor and application thereof, polymer material, and 3d stent |
| CN114591650A (en) * | 2022-04-02 | 2022-06-07 | 福州大学 | Single-component waterborne polyurethane antistatic ink and preparation method thereof |
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| CN104497833A (en) * | 2014-11-21 | 2015-04-08 | 杭州立威化工涂料有限公司 | High-performance environment-friendly water-based conductive antistatic coating and preparation method thereof |
| CN104893538A (en) * | 2015-06-04 | 2015-09-09 | 栾万强 | Waterborne antistatic coating as well as preparation method and application thereof |
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Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107501520A (en) * | 2017-09-22 | 2017-12-22 | 江苏多森化工有限公司 | A kind of antistatic treatment agent and preparation method thereof |
| CN108166095A (en) * | 2017-12-18 | 2018-06-15 | 浙江恒逸高新材料有限公司 | A kind of hydrophilic antistatic graphene Modified polyester chips and preparation method thereof |
| CN108166095B (en) * | 2017-12-18 | 2020-05-05 | 浙江恒逸高新材料有限公司 | Hydrophilic antistatic graphene modified polyester chip and preparation method thereof |
| CN108659199A (en) * | 2018-04-13 | 2018-10-16 | 中国皮革和制鞋工业研究院（晋江）有限公司 | Modified aqueous polyurethane dispersoid and preparation method thereof and vamp finishing agent |
| CN108642691A (en) * | 2018-07-05 | 2018-10-12 | 刘群英 | Antistatic fabric and preparation method thereof |
| CN108642691B (en) * | 2018-07-05 | 2020-04-24 | 珠海鑫康源新材料科技有限公司 | Antistatic fabric and preparation method thereof |
| CN109944066A (en) * | 2019-04-08 | 2019-06-28 | 福建华彩新材料有限公司 | A kind of graphene anti-static fabric and preparation method thereof |
| CN109944066B (en) * | 2019-04-08 | 2021-06-18 | 福建华彩新材料有限公司 | Graphene antistatic fabric and preparation method thereof |
| WO2020215800A1 (en) * | 2019-04-26 | 2020-10-29 | 深圳先进技术研究院 | Polyurethane material, and preparing method therefor and application thereof, polymer material, and 3d stent |
| CN114591650A (en) * | 2022-04-02 | 2022-06-07 | 福州大学 | Single-component waterborne polyurethane antistatic ink and preparation method thereof |
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Address after: 528305 Shunde Ronggui District, Foshan City, Guangdong Province Applicant after: Guangdong Demei fine chemical group Limited by Share Ltd Address before: 528305 Shunde Ronggui District, Foshan City, Guangdong Province Applicant before: Guangdong Demei Fine Chemical Co., Ltd. |
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Application publication date: 20170510 |