CN106750320A - A kind of preparation method of perfluoroalkyl modified amido silicon oil - Google Patents
A kind of preparation method of perfluoroalkyl modified amido silicon oil Download PDFInfo
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- CN106750320A CN106750320A CN201611114123.3A CN201611114123A CN106750320A CN 106750320 A CN106750320 A CN 106750320A CN 201611114123 A CN201611114123 A CN 201611114123A CN 106750320 A CN106750320 A CN 106750320A
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- perfluoroalkyl
- silicon oil
- amido silicon
- ethanol
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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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/38—Polysiloxanes modified by chemical after-treatment
- C08G77/382—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon
- C08G77/385—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon containing halogens
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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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
- C08G77/26—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen nitrogen-containing groups
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- Chemical Kinetics & Catalysis (AREA)
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- General Chemical & Material Sciences (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Abstract
The invention provides a kind of preparation method of perfluoroalkyl modified amido silicon oil, belong to organic silicone oil textile finishing technical field.The preparation method of this perfluoroalkyl modified amido silicon oil, it is characterized in that, synthesis presoma containing fluoroalkyl, the presoma containing fluoroalkyl that will be filtered out goes out the fluorine-containing alkyl modified amido silicone oil with abutment structure with amido silicon oil addition, long chain fluorine-containing alkyl is introduced in amido silicon oil molecular structure, is comprised the following steps：(1) perfluoroalkyl ethanol and organic acid are carried out into esterification by dimethylbenzene, perfluoroalkyl ethanol organic acid esters is obtained；(2) with the primary amino radical on amido silicon oil side chain there is addition reaction in perfluoroalkyl ethanol organic acid esters, and perfluoroalkyl modified amido silicon oil is obtained.Preparation method of the present invention is simple and convenient, and the perfluoroalkyl modified amido silicon oil for preparing has the advantages that to overcome white or the light coloured fabrics yellowing after arranging.
Description
Technical field
The invention belongs to organic silicone oil textile finishing technical field, it is related to a kind of perfluoroalkyl modified amido silicon oil, especially
It is a kind of preparation method of perfluoroalkyl modified amido silicon oil.
Background technology
Amido silicon oil is an important kind in organic silicone oil, using the amino in amido silicon oil and epoxide group, different
The condensation reaction carried out between the addition reaction carried out between the unsaturated groups such as cyanic acid group and carboxylic acid and its derivative, greatly
Amount is used as resin, the important modification agent of coating；On the other hand, using the suction that amido silicon oil is excellent to synthetic fibers and natural fiber
Attached property, compatibility and easy emulsibility, as fabric softener, polishing agent and personal care products.Up to the present, amino
Silicone oil is widely used to the industry-by-industries such as chemical industry, environmental protection, leather, daily use chemicals particularly textile printing and dyeing.
The most important analog assistant of textile finishing of textile printing and dyeing industry is amido silicon oil.Amido silicon oil adsorbance is big, into
Film is good and fiber binding strength strong, and after amido silicon oil finish fabric, enhancing fabric tearing toughness and resilience, reduction knit
The coefficient of friction on thing surface, fabric is set to there is smooth feeling, assign fabric sofetening smooth excellent handle；It is excellent soft except showing
It is soft outer, can also impart to fabric hydrophobicity；Amido silicon oil compatibility is splendid, with most organic softening agents and other weavings
Auxiliary agent is compatible；It is nontoxic, to human body and environment-friendly.
Amido silicon oil as textile finishing auxiliary agent, the amino contained by it is oxidized easily, can make the white after arrangement or
Light coloured fabrics yellowing.For this problem, solved today mainly by two methods：1) the modified method of secondary amino group：In amido silicon oil
The secondary amine group of high steric-hindrance amino, the energy needed for increase amido oxidation Decomposition, so as to reach the property of yellowing-resistant are introduced in structure
Energy；2) the modified method of tertiary amino：Access relative to primary amine, the more stable tertiary amine group of secondary amine does not allow it oxidizable.
But, both approaches can cause textile finishing effect to decline while fabric color inhibition is improved, and feel,
The aspect performance such as soil release performance is substantially reduced.So, for those skilled in the art, needing to be developed one kind to overcome
Perfluoroalkyl modified amido silicon oil of traditional amido silicon oil xanthochromia and preparation method thereof.
The content of the invention
The purpose of the present invention is directed to existing technology and there is above mentioned problem, it is proposed that a kind of perfluoroalkyl modified amino silicone
The preparation method of oil, the preparation method is simple and convenient, and the perfluoroalkyl modified amido silicon oil for preparing has and can overcome arrangement
Rear white or the characteristics of light coloured fabrics yellowing.
The purpose of the present invention can be realized by following technical proposal：
A kind of preparation method of perfluoroalkyl modified amido silicon oil, it is characterised in that synthesis presoma containing fluoroalkyl, will sieve
The presoma containing fluoroalkyl selected goes out the fluorine-containing alkyl modified amido silicone oil with abutment structure with amido silicon oil addition, in amino
Long chain fluorine-containing alkyl is introduced in silicone molecule structure, is comprised the following steps：
(1) perfluoroalkyl ethanol and organic acid are carried out into esterification by dimethylbenzene, perfluoroalkyl ethanol is obtained
Organic acid esters；
(2) with the primary amino radical on amido silicon oil side chain there is addition reaction in perfluoroalkyl ethanol organic acid esters, and perfluor is obtained
Alkyl modified amido silicone oil.
Effective shielding using long chain fluorine-containing alkyl to amino, not only solves the problem of oxidation of amino, while making containing fluothane
Base modified amino silicon oil shows remarkable low surface tension, Water-proof and oil-proof, chemical stability, weatherability, corrosion resistance and resists
The premium properties of the fluorine elements such as oxidisability, gives full play to the synergy of fluorine element silicon function, makes fluorine-containing alkyl modified amido silicon
Oil has the advantage of silicon fabric finishing agent and fluorine fabric finishing agent concurrently, with more perfect textile finishing performance, can be used for senior silk fabric
The wider scope such as satin clothes, room ornament, various families and office appliance, more high-grade textile finishing.
In the preparation method of above-mentioned perfluoroalkyl modified amido silicon oil, described perfluoroalkyl ethanol is perfluoro hexyl second
Alcohol or perfluor heptyl ethanol or perfluoro octyl ethanol.
In the preparation method of above-mentioned perfluoroalkyl modified amido silicon oil, the material that described organic acid is chosen is clothing health
Acid.
In the preparation method of above-mentioned perfluoroalkyl modified amido silicon oil, in described step (1), perfluoroalkyl ethanol has
Preparing for machine acid esters is comprised the steps of：
A, benzene or toluene or the solution of dimethylbenzene three to addition 280-320ml in there-necked flask；
B, addition perfluoroalkyl ethanol, itaconic acid, hydroquinones or p methoxy phenol or benzoquinones；
C, it is heated with stirring to 80-110 DEG C under nitrogen protection, reaction 10-12h stops reaction；
D, cooling, filtering, obtain limpid pale red filtrate, rotary evaporation of solvent benzene, obtain crude product；
Add hydroquinones or p methoxy phenol or benzoquinones, vacuum distillation in E, crude product, obtain water white transparency perfluor heptyl
Ethanol itaconate.
In the preparation method of above-mentioned perfluoroalkyl modified amido silicon oil, in described step (2), perfluoroalkyl modified ammonia
Preparing for base silicone oil is comprised the steps of：
A, the acetone to addition 70-90ml in there-necked flask；
B, under nitrogen protection, under sequentially add amido silicon oil and perfluor heptyl ethanol itaconate, be warming up to 50-60
DEG C, solvent is removed after reaction 2-3h, obtain perfluoroalkyl modified amido silicon oil.
In the preparation method of above-mentioned perfluoroalkyl modified amido silicon oil, the fluorine of described perfluoroalkyl modified amido silicon oil
Content (mass fraction) is 6-25%.
In the preparation method of above-mentioned perfluoroalkyl modified amido silicon oil, described perfluoroalkyl modified amido silicon oil application
In Cotton Fabric.
Compared with prior art, the preparation method of this perfluoroalkyl modified amido silicon oil has advantages below：The preparation side
Method is simple and convenient, the effective shielding using long chain fluorine-containing alkyl to amino, the problem of oxidation of amino is not only solved, while making fluorine-containing
Alkyl modified amido silicone oil show brilliance low surface tension, Water-proof and oil-proof, chemical stability, weatherability, corrosion resistance and
The premium properties of the fluorine elements such as inoxidizability.
Specific embodiment
The following is specific embodiment of the invention, technical scheme is further described, but the present invention is simultaneously
It is not limited to these embodiments.
A kind of preparation method of perfluoroalkyl modified amido silicon oil, synthesizes presoma containing fluoroalkyl, fluorine-containing by what is filtered out
Alkyl presoma goes out the fluorine-containing alkyl modified amido silicone oil with abutment structure with amido silicon oil addition, in amido silicon oil molecule knot
Long chain fluorine-containing alkyl is introduced in structure, is comprised the following steps：
(1) perfluoroalkyl ethanol and organic acid are carried out into esterification by dimethylbenzene, perfluoroalkyl ethanol is obtained
Organic acid esters, wherein, perfluoroalkyl ethanol is perfluoro hexyl ethanol or perfluor heptyl ethanol or perfluoro octyl ethanol, organic acid choosing
The material for taking is acrylic or methacrylic acid or itaconic acid；
(2) with the primary amino radical on amido silicon oil side chain there is addition reaction in perfluoroalkyl ethanol organic acid esters, and perfluor is obtained
Alkyl modified amido silicone oil, the Oil repellent (mass fraction) of perfluoroalkyl modified amido silicon oil is 6-25%, perfluoroalkyl modified
Amido silicon oil is applied to Cotton Fabric.
In step (1), preparing for perfluoroalkyl ethanol organic acid esters is comprised the steps of：
A, benzene or toluene or the solution of dimethylbenzene three to addition 280-320ml in there-necked flask；
B, addition perfluoroalkyl ethanol, organic acid, hydroquinones or p methoxy phenol or benzoquinones；
C, it is heated with stirring to 80-110 DEG C under nitrogen protection, reaction 10-12h stops reaction；
D, cooling, filtering, obtain limpid pale red filtrate, rotary evaporation of solvent benzene, obtain crude product；
Add hydroquinones or p methoxy phenol or benzoquinones, vacuum distillation in E, crude product, obtain water white transparency perfluor heptyl
Ethanol itaconate.
In step (2), preparing for perfluoroalkyl modified amido silicon oil is comprised the steps of：
A, the acetone to addition 70-90ml in there-necked flask；
B, under nitrogen protection, under sequentially add amido silicon oil and perfluor heptyl ethanol itaconate, be warming up to 50-60
DEG C, solvent is removed after reaction 2-3h, obtain perfluoroalkyl modified amido silicon oil.
Effective shielding using long chain fluorine-containing alkyl to amino, not only solves the problem of oxidation of amino, while making containing fluothane
Base modified amino silicon oil shows remarkable low surface tension, Water-proof and oil-proof, chemical stability, weatherability, corrosion resistance and resists
The premium properties of the fluorine elements such as oxidisability, gives full play to the synergy of fluorine element silicon function, makes fluorine-containing alkyl modified amido silicon
Oil has the advantage of silicon fabric finishing agent and fluorine fabric finishing agent concurrently, with more perfect textile finishing performance, can be used for senior silk fabric
The wider scope such as satin clothes, room ornament, various families and office appliance, more high-grade textile finishing.
Embodiment one
In equipped with electromagnetic agitation, water knockout drum, reflux condensing tube, the there-necked flask of thermometer, itaconic acid 22g, complete is added
Fluorine heptyl ethanol 123g, hydroquinones 2.5g, p-methyl benzenesulfonic acid 4g, 300ml benzene；Stirred under nitrogen atmosphere is heated to 85 DEG C, instead
12h is answered to there is no water generation, stopping reaction；Cool down, filter, obtaining limpid pale red filtrate, rotary evaporation of solvent benzene, obtaining slightly
Product；Add 1g hydroquinones in crude product, vacuum distillation obtains water white transparency perfluor heptyl ethanol itaconate.
In equipped with reflux condensing tube, the there-necked flask of thermometer, 80ml acetone is added, added successively under nitrogen protection
Enter 13g amido silicon oils and 5g perfluor heptyl ethanol itaconates, be warming up to 55 DEG C, solvent is removed after reaction 2h, obtain perfluoroalkyl
Modified amino silicon oil.
Embodiment two
In equipped with electromagnetic agitation, water knockout drum, reflux condensing tube, the there-necked flask of thermometer, itaconic acid 30g, complete is added
Fluorine heptyl ethanol 123g, p methoxy phenol 2g, concentrated sulfuric acid 2g, 300ml toluene；Stirred under nitrogen atmosphere is heated to 100 DEG C, instead
10h is answered to there is no water generation, stopping reaction；Cool down, filter, obtaining limpid pale red filtrate, rotary evaporation of solvent benzene, obtaining slightly
Product；Add 1g p methoxy phenols in crude product, vacuum distillation obtains water white transparency perfluor heptyl ethanol itaconate.
In equipped with reflux condensing tube, the there-necked flask of thermometer, 80ml acetone is added, added successively under nitrogen protection
Enter 13g amido silicon oils and 5g perfluor heptyl ethanol itaconates, be warming up to 55 DEG C, solvent is removed after reaction 2h, obtain perfluoroalkyl
Modified amino silicon oil.
Embodiment three
In equipped with electromagnetic agitation, water knockout drum, reflux condensing tube, the there-necked flask of thermometer, itaconic acid 20g, complete is added
Fluorine heptyl ethanol 107g, benzoquinones 2.1g, p-methyl benzenesulfonic acid 3g, 300ml dimethylbenzene；105 DEG C are heated with stirring to, 10h is not to for reaction
There is water to generate again, stop reaction；Cool down, filter, obtaining limpid pale red filtrate, rotary evaporation of solvent dimethylbenzene, obtaining crude product；
Add 1g benzoquinones in crude product, vacuum distillation obtains water white transparency perfluor heptyl ethanol itaconate.
In equipped with reflux condensing tube, the there-necked flask of thermometer, 80ml acetone is added, added successively under nitrogen protection
Enter 13g amido silicon oils and 5g perfluor heptyl ethanol itaconates, be warming up to 55 DEG C, solvent is removed after reaction 2h, obtain perfluoroalkyl
Modified amino silicon oil.
Specific embodiment described herein is only to the spiritual explanation for example of the present invention.Technology neck belonging to of the invention
The technical staff in domain can be made various modifications or supplement to described specific embodiment or be replaced using similar mode
Generation, but without departing from spirit of the invention or surmount scope defined in appended claims.
Although more having used term herein, it is not precluded from using the possibility of other terms.Use these terms
Just for the sake of more easily describing and explaining essence of the invention；Be construed as any additional limitation be all with
What spirit of the present invention was disagreed.
Claims (7)
1. a kind of preparation method of perfluoroalkyl modified amido silicon oil, it is characterised in that synthesis presoma containing fluoroalkyl, will screen
The presoma containing fluoroalkyl for going out goes out the fluorine-containing alkyl modified amido silicone oil with abutment structure with amido silicon oil addition, in amino silicone
Long chain fluorine-containing alkyl is introduced in oil minor structure, is comprised the following steps：
(1) perfluoroalkyl ethanol and organic acid are carried out into esterification by dimethylbenzene, perfluoroalkyl ethanol is obtained organic
Acid esters；
(2) with the primary amino radical on amido silicon oil side chain there is addition reaction in perfluoroalkyl ethanol organic acid esters, and perfluoroalkyl is obtained
Modified amino silicon oil.
2. the preparation method of perfluoroalkyl modified amido silicon oil according to claim 1, it is characterised in that described perfluor
Alkyl alcohol is perfluoro hexyl ethanol or perfluor heptyl ethanol or perfluoro octyl ethanol.
3. the preparation method of perfluoroalkyl modified amido silicon oil according to claim 1, it is characterised in that described is organic
The material that acid is chosen is itaconic acid.
4. the preparation method of perfluoroalkyl modified amido silicon oil according to claim 1, it is characterised in that described step
(1) in, preparing for perfluoroalkyl ethanol organic acid esters is comprised the steps of：
A, benzene or toluene or the solution of dimethylbenzene three to addition 280-320ml in there-necked flask；
B, addition perfluoroalkyl ethanol, itaconic acid, hydroquinones or p methoxy phenol or benzoquinones；
C, be heated with stirring to 80-110 DEG C under nitrogen protection, reaction 10-12h to there is no water generation, stop reaction；
D, cooling, filtering, obtain limpid pale red filtrate, rotary evaporation of solvent benzene, obtain crude product；
Add hydroquinones or p methoxy phenol or benzoquinones, vacuum distillation in E, crude product, obtain perfluor heptyl ethanol itaconate.
5. the preparation method of perfluoroalkyl modified amido silicon oil according to claim 1, it is characterised in that described step
(2) in, preparing for perfluoroalkyl modified amido silicon oil is comprised the steps of：
A, the acetone to addition 70-90ml in there-necked flask；
B, under nitrogen protection, under sequentially add amido silicon oil and perfluor heptyl ethanol itaconate, be warming up to 50-60 DEG C, instead
Solvent is removed after answering 2-3h, perfluoroalkyl modified amido silicon oil is obtained.
6. the preparation method of perfluoroalkyl modified amido silicon oil according to claim 1, it is characterised in that described perfluor
The Oil repellent of alkyl modified amido silicone oil is 6-25%.
7. the preparation method of perfluoroalkyl modified amido silicon oil according to claim 1, it is characterised in that described perfluor
Alkyl modified amido silicone oil is applied to Cotton Fabric.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201611114123.3A CN106750320A (en) | 2016-12-07 | 2016-12-07 | A kind of preparation method of perfluoroalkyl modified amido silicon oil |
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| CN201611114123.3A CN106750320A (en) | 2016-12-07 | 2016-12-07 | A kind of preparation method of perfluoroalkyl modified amido silicon oil |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112552515A (en) * | 2019-09-25 | 2021-03-26 | 山东东岳未来氢能材料股份有限公司 | Fluorine-containing amino silicone oil and preparation method and application thereof |
| CN115162030A (en) * | 2022-08-04 | 2022-10-11 | 山东绿之能环保科技有限公司 | Environment-friendly printing and dyeing auxiliary for spinning and preparation method thereof |
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| CN101967229A (en) * | 2010-10-20 | 2011-02-09 | 苏州大学 | Fluorine-containing silicone oil and preparation method thereof |
| CN103437190A (en) * | 2013-08-29 | 2013-12-11 | 华南理工大学 | Amino-silicone oil softener containing fluorine group and quaternary ammonium salt group as well as preparation method and application thereof |
| CN103643528A (en) * | 2013-11-22 | 2014-03-19 | 桐乡市濮院毛针织技术服务中心 | Method for darkening finishing of wool fabric |
| CN105330867A (en) * | 2015-12-07 | 2016-02-17 | 浙江汉邦化工有限公司 | Organic fluorine-silicon surface treatment agent and preparation method thereof |
-
2016
- 2016-12-07 CN CN201611114123.3A patent/CN106750320A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101967229A (en) * | 2010-10-20 | 2011-02-09 | 苏州大学 | Fluorine-containing silicone oil and preparation method thereof |
| CN103437190A (en) * | 2013-08-29 | 2013-12-11 | 华南理工大学 | Amino-silicone oil softener containing fluorine group and quaternary ammonium salt group as well as preparation method and application thereof |
| CN103643528A (en) * | 2013-11-22 | 2014-03-19 | 桐乡市濮院毛针织技术服务中心 | Method for darkening finishing of wool fabric |
| CN105330867A (en) * | 2015-12-07 | 2016-02-17 | 浙江汉邦化工有限公司 | Organic fluorine-silicon surface treatment agent and preparation method thereof |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112552515A (en) * | 2019-09-25 | 2021-03-26 | 山东东岳未来氢能材料股份有限公司 | Fluorine-containing amino silicone oil and preparation method and application thereof |
| CN112552515B (en) * | 2019-09-25 | 2022-07-26 | 山东东岳未来氢能材料股份有限公司 | Fluorine-containing amino silicone oil and preparation method and application thereof |
| CN115162030A (en) * | 2022-08-04 | 2022-10-11 | 山东绿之能环保科技有限公司 | Environment-friendly printing and dyeing auxiliary for spinning and preparation method thereof |
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