CN104650364B - A kind of preparation method of hyperbranched polyether amino block organosilicon - Google Patents
A kind of preparation method of hyperbranched polyether amino block organosilicon Download PDFInfo
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Abstract
The invention discloses a kind of preparation method of hyperbranched polyether amino block organosilicon, comprise the following steps：The preparation of polyether/epoxy resin block silicone oil；The preparation of hyperbranched polyether amino block organosilicon.The present invention, which combines dissaving polymer and linear polyether amino block organosilicon, is developed into novel organosilicon softening agent, possess new modified organic silicon chemical constitution, the over-expense compound of synthesis has network structure, cohesive force that can not only be between reinforcing fiber, the cohesive force between yarn can also be strengthened, molecular mass is high, and viscosity is low, hydrophilic radical is more, can give fabric sofetening plentiful and washable feel；Solve traditional amino-modified silicone oil to be easily demulsified problem, product has automatic emulsifying performance, good emulsion stability in water；Reduce yellowing, enhance hydrophily；Its good hydrophilic property of the fabric sorted out, it is yellowing small, combined with fabric with chemical bond form, add washability, while having the soft effect of amido silicon oil again.
Description
Technical field
The invention belongs to field of organic silicon, and in particular to a kind of preparation method of hyperbranched polyether amino block organosilicon.
Background technology
At present, amido silicon oil turns into dyeing using quite varied post-finishing agent with its excellent soft, flatness,
Fabric after its arrangement has soft, smooth, washable and comfortable and easy to wear performance.But amido silicon oil is in the arrangement mode of fiber
Hydrophilic Fiber is set to be deteriorated, fabric moisture and snugness of fit decline；White or light coloured fabrics after being arranged with it, in high temperature
After baking, it may appear that different degrees of xanthochromia and aberration；And its stability of emulsion is poor, easily occur in storage and transportation
" floating oil demulsification " phenomenon.
At present, the latest development of weaving organic silicone finishing agent is that linear polyether block amino ternary polymerization organic silicon is soft
Agent is a class using widely applicable, has automatic emulsifying performance, the fabric organic silicone finishing agent of good emulsion stability, warp in water
Fabric after its arrangement has the performance of good flexibility, hydrophily, antistatic behaviour and non-discoloration.Also there are some performances at present
Relatively good silicone softening agent, such as publication date are on October 5th, 2011, Publication No. CN102206921A Chinese patent
In, patent discloses a kind of preparation method of polyether block amino silicone soft finishing agent, and the preparation method comprises the following steps：
A, diisocyanate, polyether Glycols and hydroxy silicon oil are used for raw material, prepare the polyether block organosilicon with-OH end groups and gather
Urethane；B, using the polyether block organic silicon polyurethane with-OH end groups as primary raw material, with silane coupler carry out chain extending reaction
Afterwards, add acid neutralization, moisture dissipate obtain polyether block amino silicone soft finishing agent.And for example publication date is August 1 in 2012
Day, in Publication No. CN102617863A Chinese patent, patent discloses a kind of system of hydrophilic block polyether aminosilicone
Preparation Method, the preparation method is mainly included the following steps that：A, preparation end containing hydrogen silicone oil intermediate, use cyclosiloxane to be main former
Material, block reaction is carried out with hydrogeneous double seal head, generates end containing hydrogen silicone oil intermediate；B, preparation end epoxy silicon oil intermediate, by end
Containing hydrogen silicone oil carries out addition reaction with pi-allyl epoxidized polyether, generates end epoxy silicon oil；C, finished product preparation, using end ring oxygen silicon
Oil carries out ammonolysis ring-opening reaction with polyetheramine, and hydrophilic block polyether aminosilicone is made.The product of both the above preparation method
Linear polyether block amido silicon oil is belonged to, by introducing the polyether segment of macromolecule on silicone backbone, is improved whole
The hydrophily of fabric after reason, and improve state of the product in water, improve and introduced on product emulsion stability, macromolecular chain
Be generally primary amine groups, relatively stablize, it is not easy to aoxidize, the fabric after arrangement is nearly free from Yellowing.But it is used as line
Type ternary polymerization organosilicon, introduces the polyether segment of macromolecule on macromolecular main chain, and the methyl in silicon-oxygen backbone is smooth
Layer cut-out, and molecular weight is big not as good as amido silicon oil, so its soft slipping is not so good as amido silicon oil；In addition, amino block is existed
In main chain, influenceed by steric hindrance and polarity, fiber surface absorption not as good as amido silicon oil, so its washability is relatively
Difference.
In summary, there is presently no a kind of hydrophily for having tri-block silicone oil concurrently, stability of emulsion and amido silicon oil
The preparation method of the silicone softening agent of soft slipping.
The content of the invention
Goal of the invention：The present invention provides a kind of preparation method of hyperbranched polyether amino block organosilicon, the over-expense of synthesis
Compound has network structure, cohesive force that can not only be between reinforcing fiber, moreover it is possible to strengthen the cohesive force between yarn.
Technical scheme：A kind of preparation method of hyperbranched polyether amino block organosilicon, comprises the following steps：
(1) preparation of polyether/epoxy resin block silicone oil：
Obtained end ring oxygen closure agent and octamethylcy-clotetrasiloxane are added according to a certain percentage, dress is filled with nitrogen
Put, in three mouthfuls of reactors of reflux condensing tube, add solvent isopropanol, consumption is the 30% of reaction-ure mixture.Stirring is warming up to
50 DEG C of decompression dehydration 30min, add a certain amount of base catalyst, are continuously heating to 100 DEG C~110 DEG C, 4~5h of insulation reaction；Again
Low-boiling-point substance is removed under reduced pressure, polyether/epoxy resin block silicone oil is made；
Specific reaction equation is as follows：
(2) preparation of hyperbranched polyether amino block organosilicon：
Homemade polyether/epoxy resin block silicone oil, diethylenetriamine are added with nitrogen charging device according to a certain percentage,
In three mouthfuls of reactors of reflux condensing tube, solvent isopropanol is added, consumption is the 30% of reaction-ure mixture, is heated up after stirring
To 80 DEG C, after insulation reaction 5h, vacuum distillation removes solvent, obtains the poly- silicon of light yellow transparent liquid hyperbranched polyether amino block
Oxygen alkane；
Specific reaction equation is as follows：
A is
It is used as optimization：The step 1) in epoxy radicals end-blocking polyether block siloxanes, octamethylcy-clotetrasiloxane rubs
You are than being 1:15~20.
It is used as optimization：The step 1) in base catalyst be TMAH, catalyst amount be 0.035%~
0.055%.It is used as optimization：The step 2) in polyether/epoxy resin block silicone oil and diethylenetriamine mol ratio be 1.5~2:
1。
It is used as optimization：The step 1) in end ring oxygen closure agent prepared by following substances：
By the hydrogen-based disiloxane of tetramethyl two and allyl polyethenoxy glycidol ether according to 1:2.2 ratio mixing,
Stir, add 1% isopropyl alcohol solution of chloroplatinic acid, consumption is 20mg/kg, be warming up to 80 DEG C~90 DEG C 3~4h of reaction, subtract
Pressure is distilled off low-boiling-point substance and obtains end ring oxygen closure agent.
Beneficial effect：The specific advantage of the present invention is as follows：
1st, the present invention dissaving polymer and linear polyether amino block organosilicon are combined be developed into it is new organic
Silicone softener, it possesses the cohesive force between new modified organic silicon chemical constitution, the over-expense compound energy reinforcing fiber of synthesis, point
Protonatomic mass is high, and viscosity is low, and hydrophilic radical is more, can give fabric sofetening plentiful and washable feel.Diethylenetriamine increase
Hydrophily and improve durability and effect.Polyethers is added in molecule segment, and by EO numbers n controls in polyethers in 25-
40, polyether group has extremely strong hydrophily, and hydrophobic organosilicon can be made to be changed into hydrophilic organic silicon, emulsion floating oil is solved
The problem of, simplify emulsifying process, and the fabric after being arranged through organic silicon modified by polyether also has good soil resistant and anti-quiet
Electrically, it is a series of scarce that " moisture absorption absorption of perspiration is low ", " being also easy to produce frictional static " etc. are overcome after simple polysiloxanes finish fabric
Point；Diethylenetriamine is recycled to carry out hyperbranched so that structure easily forms hydrogen bond very with water, can be emulsified without emulsifying agent,
Overcome the problem of conventional easy floating oil of organic silicone oil softening agent is demulsified.Simultaneously as the product is hyperbranched network structure, no
It is only capable of the active force such as fiber utilization hydrogen bond in single yarn being coated togather, while can also will many using the network structure of super large
One thread is coated togather, and considerably increases yarn and interfibrous cohesive force.
2nd, when silicone oil is made into housekeeping liquid, suitably its pH value is adjusted between 5~6 with glacial acetic acid, acetic acid
Add, the raising of formation and stability to dressing liquid has material impact.This is primarily due to acetic acid can be with amino therein
Reaction generation quaternary ammonium salt, enhances the polarity of silicone oil, is readily dispersed in water, form O/W type emulsions.Hyperbranched polyether ammonia
Base block silicone oil solves traditional amino-modified silicone oil during storage and use and is easily demulsified problem, product have in water from
Emulsifiability, good emulsion stability；Reduce yellowing, enhance hydrophily, be particularly suitable for white or the softness of light coloured fabrics
Arrange.
3rd, the fabric that this product is sorted out overcomes the shortcoming of common ternary polymerization silicone oil, and its good hydrophilic property is yellowing small,
Combined with fabric with chemical bond form, add washability, while having the soft effect of amido silicon oil again.
Brief description of the drawings
Fig. 1 is the absorption schematic diagram of the silicone softening agent of the present invention.
Embodiment
With reference to specific embodiment, the present invention will be described in detail.
Specific embodiment：
Embodiment 1
A kind of preparation method of hyperbranched polyether amino block organosilicon, comprises the following steps：
(1) preparation of polyether/epoxy resin block silicone oil：
Obtained end ring oxygen closure agent and octamethylcy-clotetrasiloxane are added according to a certain percentage, dress is filled with nitrogen
Put, in three mouthfuls of reactors of reflux condensing tube, add solvent isopropanol, consumption is the 30% of reaction-ure mixture.Stirring is warming up to
50 DEG C of decompression dehydration 30min, add a certain amount of base catalyst, are continuously heating to 100 DEG C, insulation reaction 4h；It is removed under reduced pressure again low
Thing is boiled, polyether/epoxy resin block silicone oil is made.
The epoxy radicals end-blocking polyether block siloxanes, the mol ratio of octamethylcy-clotetrasiloxane are 1:15.
The base catalyst is TMAH, and catalyst amount is 0.035%.
The end ring oxygen closure agent is prepared by following substances：By the hydrogen-based disiloxane of tetramethyl two and pi-allyl polyoxy
Ethene glycidol ether is according to 1:2.2 ratio mixing, stirs, adds 1% isopropyl alcohol solution of chloroplatinic acid, consumption is
20mg/kg, is warming up to 80 DEG C of reaction 3h, and vacuum distillation removes low-boiling-point substance and obtains end ring oxygen closure agent.
(2) preparation of hyperbranched polyether amino block organosilicon：
Homemade polyether/epoxy resin block silicone oil, diethylenetriamine are added with nitrogen charging device according to a certain percentage,
In three mouthfuls of reactors of reflux condensing tube, solvent isopropanol is added, consumption is the 30% of reaction-ure mixture, is heated up after stirring
To 80 DEG C, after insulation reaction 5h, vacuum distillation removes solvent, obtains the poly- silicon of light yellow transparent liquid hyperbranched polyether amino block
Oxygen alkane.
The polyether/epoxy resin block silicone oil and the mol ratio of diethylenetriamine are 1.5:1.
Embodiment 2
A kind of preparation method of hyperbranched polyether amino block organosilicon, comprises the following steps：
(1) preparation of polyether/epoxy resin block silicone oil：
Obtained end ring oxygen closure agent and octamethylcy-clotetrasiloxane are added according to a certain percentage, dress is filled with nitrogen
Put, in three mouthfuls of reactors of reflux condensing tube, add solvent isopropanol, consumption is the 30% of reaction-ure mixture.Stirring is warming up to
50 DEG C of decompression dehydration 30min, add a certain amount of base catalyst, are continuously heating to 110 DEG C, insulation reaction 5h；It is removed under reduced pressure again low
Thing is boiled, polyether/epoxy resin block silicone oil is made.
The epoxy radicals end-blocking polyether block siloxanes, the mol ratio of octamethylcy-clotetrasiloxane are 1:20.
The base catalyst is TMAH, and catalyst amount is 0.055%.
The end ring oxygen closure agent is prepared by following substances：By the hydrogen-based disiloxane of tetramethyl two and pi-allyl polyoxy
Ethene glycidol ether is according to 1:2.2 ratio mixing, stirs, adds 1% isopropyl alcohol solution of chloroplatinic acid, consumption is
20mg/kg, is warming up to 90 DEG C of reaction 4h, and vacuum distillation removes low-boiling-point substance and obtains end ring oxygen closure agent.
(2) preparation of hyperbranched polyether amino block organosilicon：
Homemade polyether/epoxy resin block silicone oil, diethylenetriamine are added with nitrogen charging device according to a certain percentage,
In three mouthfuls of reactors of reflux condensing tube, solvent isopropanol is added, consumption is the 30% of reaction-ure mixture, is heated up after stirring
To 80 DEG C, after insulation reaction 5h, vacuum distillation removes solvent, obtains the poly- silicon of light yellow transparent liquid hyperbranched polyether amino block
Oxygen alkane.
The polyether/epoxy resin block silicone oil and the mol ratio of diethylenetriamine are 2:1.
Embodiment 3
A kind of preparation method of hyperbranched polyether amino block organosilicon, comprises the following steps：
(1) preparation of polyether/epoxy resin block silicone oil：
Obtained end ring oxygen closure agent and octamethylcy-clotetrasiloxane are added according to a certain percentage, dress is filled with nitrogen
Put, in three mouthfuls of reactors of reflux condensing tube, add solvent isopropanol, consumption is the 30% of reaction-ure mixture.Stirring is warming up to
50 DEG C of decompression dehydration 30min, add a certain amount of base catalyst, are continuously heating to 105 DEG C, insulation reaction 4.5h；It is removed under reduced pressure again
Low-boiling-point substance, is made polyether/epoxy resin block silicone oil.
The epoxy radicals end-blocking polyether block siloxanes, the mol ratio of octamethylcy-clotetrasiloxane are 1:17.
The base catalyst is TMAH, and catalyst amount is 0.045%.
The end ring oxygen closure agent is prepared by following substances：By the hydrogen-based disiloxane of tetramethyl two and pi-allyl polyoxy
Ethene glycidol ether is according to 1:2.2 ratio mixing, stirs, adds 1% isopropyl alcohol solution of chloroplatinic acid, consumption is
20mg/kg, is warming up to 85 DEG C of reaction 3.5h, and vacuum distillation removes low-boiling-point substance and obtains end ring oxygen closure agent.
(2) preparation of hyperbranched polyether amino block organosilicon：
Homemade polyether/epoxy resin block silicone oil, diethylenetriamine are added with nitrogen charging device according to a certain percentage,
In three mouthfuls of reactors of reflux condensing tube, solvent isopropanol is added, consumption is the 30% of reaction-ure mixture, is heated up after stirring
To 80 DEG C, after insulation reaction 5h, vacuum distillation removes solvent, obtains the poly- silicon of light yellow transparent liquid hyperbranched polyether amino block
Oxygen alkane.
The polyether/epoxy resin block silicone oil and the mol ratio of diethylenetriamine are 1.8:1.
Table 1 below be different polysiloxane emulsions performance, from table 1 we can see that：Product formation self-emulsifying, no
Emulsifying agent need to be added in addition, and is then needed using the emulsifications such as 1305,1307 for the maximum amino-modified silicone oil of existing market consumption
Agent is made on emulsion ability finish fabric, but there are problems that improper use demulsification.
The performance of the different polysiloxane emulsions of table 1
The performance of the different amino modified polysiloxane emulsion finish fabrics of table 2
Table 2 is the performance of different amino modified polysiloxane emulsion finish fabrics, wherein, fabric is：300D × 300D is washed
Synthetic fibre long filament, door width 160cm, grammes per square metre 74g/m2, black fabric.We can see that product is to wet colour fastness and distillation from table
Fastness is significantly improved, and illustrates that finishing agent forms stronger adhesion with fabric, product is soft, elasticity, moisture absorption thermal diffusivity
Can preferably, the moisture absorption thermal diffusivity of fabric depends on the hydrophily of the continuity and product of product epithelium in itself after processing.Wherein, it is whole
Managing technological process is：Two leachings two roll → preliminary drying → and bake → sample.
Claims (1)
1. a kind of preparation method of hyperbranched polyether amino block organosilicon, it is characterised in that：Comprise the following steps：
(1) preparation of polyether/epoxy resin block silicone oil：
Obtained end ring oxygen closure agent and octamethylcy-clotetrasiloxane are added according to a certain percentage, with nitrogen charging device,
In three mouthfuls of reactors of reflux condensing tube, solvent isopropanol is added, consumption is the 30% of reaction-ure mixture, and stirring is warming up to 50 DEG C
Decompression dehydration 30min, adds a certain amount of base catalyst, is continuously heating to 100 DEG C~110 DEG C, 4~5h of insulation reaction；Depressurize again
Low-boiling-point substance is removed, polyether/epoxy resin block silicone oil is made；
Specific reaction equation is as follows：
(2) preparation of hyperbranched polyether amino block organosilicon：
Homemade polyether/epoxy resin block silicone oil, diethylenetriamine are added with nitrogen charging device, backflow according to a certain percentage
In three mouthfuls of reactors of condenser pipe, solvent isopropanol is added, consumption is the 30% of reaction-ure mixture, and 80 are warming up to after stirring
DEG C, after insulation reaction 5h, vacuum distillation removes solvent, obtains the poly- silica of light yellow transparent liquid hyperbranched polyether amino block
Alkane；
Specific reaction equation is as follows：
A is
The step 1) in end ring oxygen closure agent prepared by following substances：
By the hydrogen-based disiloxane of tetramethyl two and allyl polyethenoxy glycidol ether according to 1:2.2 ratio mixing, stirring
Uniformly, the isopropyl alcohol solution of chloroplatinic acid of addition 1%, consumption is 20mg/kg, is warming up to 80 DEG C~90 DEG C 3~4h of reaction, and decompression is steamed
Distillation goes low-boiling-point substance to obtain end ring oxygen closure agent,
The step 1) in epoxy radicals end-blocking polyether block siloxanes, octamethylcy-clotetrasiloxane mol ratio be 1:15~
20；
The step 1) in base catalyst be TMAH, catalyst amount be 0.035%~0.055%；
The step 2) in polyether/epoxy resin block silicone oil and diethylenetriamine mol ratio be 1.5~2:1；
When silicone oil is made into housekeeping liquid, its pH value is adjusted between 5~6 with glacial acetic acid, the addition of acetic acid, to arranging
The formation of liquid and the raising of stability have material impact, because acetic acid can be with amino therein reaction generation quaternary ammonium salt, reinforcing
The polarity of silicone oil, is readily dispersed in water, forms O/W type emulsions.
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