CN102660029B - Cation modified supersoft hydrophilic block silicone oil compound and preparation method and application - Google Patents
Cation modified supersoft hydrophilic block silicone oil compound and preparation method and application Download PDFInfo
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Abstract
The invention relates to the field of textile finishing agents, in particular to a cation modified supersoft hydrophilic block silicone oil compound and a preparation method and application. The cation modified supersoft hydrophilic block silicone oil compound has a cation having the following structural formula, wherein n1 is 5 to 10, R is shown in the accompanying drawing, a is 0 to 3, b is 0 to 3, and n is 10 to 40. The cation modified supersoft hydrophilic block silicone oil compound synthesized by the invention is suitable for hand feeling finishing of textiles consisting of one or more fibers such as cotton, polyester, nylon and acrylic fiber, has softer, slipperier and fluffier effects than an amino silicone oil, has more excellent stability such as acid and alkali resistance, electrolyte resistance, high temperature resistance and shear resistance, and thoroughly solves the problems of easy demulsification, floating oil, roller sticking and difficulty in rehandling of the traditional amino silicone oil.
Description
Technical field
The present invention relates to textile finish field, relate in particular to a kind of cation-modified super soft hydrophilic block silicon oil compound and preparation method and application.
Background technology
In the hand feel finishing agent of textiles, more than 80% need to use amido silicon oil in the market.Amido silicon oil is that grow up the eighties in last century a kind of is mainly used in softness, the modified silicon oil that fluffy, smooth hand arranges, its molecular backbone chain is that the Si-O key with excellent flexibility forms, on side chain, according to different amino silicane coupling agents, introduced the amino of different structure, amino has the chemical propertys such as stronger polarity, reactivity, adsorptivity, thereby has given amido silicon oil geneogenous advantage on fabric feeling finishing effect.But amido silicon oil can not directly be used, must add after emulsifying agent is emulsified into emulsion and could use.Through technical development for many years, the selection of amino silicone oil emulsifying agent, the aspects such as optimization of emulsifying process have obtained changing thoroughly, but still can not be from solve in essence amido silicon oil use procedure easily breakdown of emulsion, floating oil, roll banding, sticky cylinder, easily produce the problems such as silicone oil spot, meanwhile, the introducing of the highly active amino of side chain has caused fabric after the easy look change of fabric, xanthochromia, the processing a series of problem such as can not return something for repairs.In recent years, the block silicone oil of substituted-amino silicone oil product progressively comes into vogue on market, but the raw material dependence on import due to synthetic operation more complicated, key, particularly can not 100% in the addition process of silicon hydrogen and glycidyl allyl ether transform, cause that block silicone oil quality is in the market unstable, cost is higher; Selectable Amino Terminated polyether(ATPE) kind is limited simultaneously, causes the scope of application of block silicone oil narrower, in the hand feel finishing of various fabrics, cannot embody the effect that amido silicon oil has; In synthetic process, adopted a large amount of volatile solvents simultaneously, although harmless, rear arrangement processing environment has been brought to many detrimentally affects.
Publication number is the preparation method that the patent of invention of CN101497697A discloses a kind of block water-soluble silicon oil, method has comprised the preparation of the amidation of amino coupling agent, the preparation of holding hydrogeneous methylsiloxane intermediate, polysiloxane-polyether linear block copolymers and four preparation processes such as ammonia solution of segmented copolymer, whole building-up process relates to a plurality of heterogeneous chemical reactions, stability influence to product quality is larger, in the multiple conversion of amino, affected amino activity, its treatment effect is significantly declined.
Publication number is the preparation method that the patent of invention of CN101497697A discloses a kind of polysiloxanes-amidopolyether block copolymer, method has comprised α, the preparation of ω-hydrogen siloxane intermediate, α, the preparation of ω-bicyclic oxygen polysiloxane intermediate, three steps of preparation of polysiloxanes-amidopolyether block copolymer, synthetic product can solve the application deficiency that amido silicon oil exists preferably, but at α, in the building-up process of ω-bicyclic oxygen polysiloxane intermediate, epoxy group(ing) is at high temperature, under acid condition, easily open loop has a strong impact on follow-up synthesizing, and then affect the quality stability of product.In polysiloxanes-amidopolyether block copolymer building-up process, adopted Amino Terminated polyether(ATPE), Amino Terminated polyether(ATPE) is mainly controlled by U.S. Huntsman Corporation at present, product price is higher, of less types, cause that the product cost produced is higher, the scope of application is narrower, be mainly used in trevira hand feel finishing and on other fiber treatment effect poor, so substituted-amino silicone oil all sidedly.
Summary of the invention
In order to solve above-mentioned technical problem, an object of the present invention is to provide a kind of cation-modified super soft hydrophilic block silicon oil compound, second object of the present invention is to provide the preparation method of above-mentioned cation-modified super soft hydrophilic block silicon oil compound, and the 3rd object of the present invention is to provide the application of above-mentioned cation-modified super soft hydrophilic block silicon oil compound.The cation-modified super soft hydrophilic block silicon oil compound that the present invention synthesizes is applicable to the hand feel finishing of one or more fibrous fabrics of cotton, terylene, polyamide fibre, acrylic fibers, there is soft, sliding, the fluffy effect that surmounts amido silicon oil, have more excellent acid and alkali-resistance, electrolyte-resistant, high temperature resistant, resistance to shearing equistability, the problem such as thoroughly solved easy breakdown of emulsion, floating oil, roll banding that traditional amido silicon oil exists, be difficult for returning something for repairs.
In order to realize first above-mentioned object, the present invention has adopted following technical scheme:
Cation-modified super soft hydrophilic block silicon oil compound, this compound has the positively charged ion of following structural formula:
；
Described n1 is 5 ~ 10, and described R is
, a=0 ~ 3 wherein, b=0 ~ 3, n=10 ~ 40.
In order to realize second above-mentioned object, the present invention has adopted following technical scheme:
The preparation method of cation-modified super soft hydrophilic block silicon oil compound, the method comprises the following steps:
1) α, the preparation method of omega-amino-polysiloxane intermediate
By the octamethylcyclotetrasiloxane and 1 after dehydration, 1,3,3-tetramethyl-two aminopropyl sily oxide add in there-necked flask according to certain ratio, open to stir and be warmed up between 90-95 ℃, then add temporary basic catalyst, consumption is the 0.1-0.2% of octamethylcyclotetrasiloxane quality, insulation reaction 5-6 hour between 90-95 ℃; After insulation finishes, be warmed up to 130-140 ℃ of left and right, be incubated 1 hour, basic catalyst is fully decomposed; Vacuumize the low-boiling-point substance of pulling out in reactant, between temperature is controlled 140-150 ℃, relative vacuum degree is controlled-99.8--99.9KPa left and right, obtains the α of low boiling mixture content≤1%, omega-amino-polysiloxane intermediate;
2) end epoxidized polyether and α, the preparation method of omega-amino-polysiloxane intermediate block polymerization
To hold epoxidized polyether, α, omega-amino-polysiloxane intermediate is according to epoxy group(ing) mole number: the ratio that amino mole number is 1:1.1-1:1.2 joins in there-necked flask, add organic solvent, consumption is the 40%-50% of reactant total mass, after adding, opens and stirs, fully stir 20 ~ 30 minutes, be warmed up to 80-85 ℃, insulation reaction 15-20 hour, gets final product to obtain the organopolysiloxane polyether block copolymer of polysiloxane, amino, polyethers ternary block;
3) the cation-modified preparation method of organopolysiloxane polyether block copolymer
In step 2) on the basis of the organopolysiloxane polyether block copolymer of prepared polysiloxane, amino, polyethers ternary block, add a certain amount of alkylating reagent monochloroethane, stirring is warmed up to 95-100 ℃ of left and right, and insulation reaction 3-4 hour gets final product to obtain super soft hydrophilic block silicone oil.
As further improvement, the temporary basic catalyst described in described step 1) is (CH
3)
4nOH alkali glue or (n-C
4h
9)
4pOH alkali glue.
As further improvement, described step 2) described organic solvent is one or several combination of Virahol, ethylene glycol monobutyl ether, ethylene glycol ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, Diethylene Glycol, dipropylene glycol.
As further improvement, described step 2) described in the general structure of end epoxidized polyether be:
A=0-3 wherein, b=0-3, one or more end epoxidized polyethers in n=10-40.
In order to realize the 3rd above-mentioned object, the present invention has adopted following technical scheme:
The agent of soft hydrophilic block sillicon oil treatment, this finishing composition comprises above-mentioned super soft hydrophilic block silicon oil compound, the weight ratio of described super soft hydrophilic block silicon oil compound is respectively 1% ~ 60%.
The present invention is owing to having adopted above-mentioned technical scheme, and with respect to prior art, the present invention has the following advantages
1) the super soft hydrophilic block silicone oil that prepared by the present invention adopts and domesticly easily produces, easily buying, end epoxidized polyether various in style are basic material, on the backbone structure of polysiloxane, successfully embed the polyether segment with excellent wetting ability, kindliness, product has excellent automatic emulsifying performance, hydrophilicity and materialization stability, has thoroughly solved the easy breakdown of emulsion of traditional amido silicon oil, floating oil, roll banding, sticky cylinder, easily produces oil mark, the problem such as be difficult for returning something for repairs;
2) the super soft hydrophilic block silicone oil that prepared by the present invention has carried out alkylated cation modification on the basis of the organopolysiloxane polyether block copolymer of polysiloxane, amino, polyethers ternary block, polarity, adsorptivity and the reactivity of product under the condition of less amino content, have further been improved, can reduce significantly the consumption of finishing composition, and expanded the scope of application of product, various fibers are all had to excellent finishing effect, solved current block silicone oil in wool, cotton, the poor problem of acrylic fabric feel; The raising of cationization degree, gives super soft hydrophilic block silicone oil certain antibiotic, anti-static function, and the while can be given the fluffy feel as the distinguished eider down of fabric; Reactive hydrogen on amino is thoroughly replaced by alkylated reaction, efficiently solves the problem of easy xanthochromia under amino hot conditions, still less look change of fabric, xanthochromia after processing.
Embodiment
Below in conjunction with embodiment, the invention will be further described, but the scope of protection of present invention is not limited to the scope of embodiment statement.
embodiment 1-1 α, the preparation of omega-amino-polysiloxane intermediate
In the 2000ml there-necked flask of constant speed electric mixer, thermometer is housed, add 1,1,3 of the octamethylcyclotetrasiloxane (D4) of 1230g and 50 grams, 3-tetramethyl-two aminopropyl sily oxide, stir and are warmed up to 90-95 ℃ of left and right, then add 1.28g(CH
3)
4nOH content is 10% (CH
3)
4nOH alkali glue, insulation reaction 6 hours, after insulation finishes, is warmed up to 135 ℃, is incubated 1 hour, by catalyzer (CH
3)
4nOH fully decomposes, and slowly vacuumizes, and has a large amount of low-boiling-point substances to flow out, and in temperature, is 150 ℃, and relative vacuum degree be-condition of 99.9KPa, pull out low-boiling-point substance 1 hour, until there is no material outflow.Synthetic product is colorless transparent viscous liquid, and ammonia value is: 0.345mmol/g, viscosity is: 50-55cs, fugitive constituent is :≤1%.
embodiment 1-2 α, ω--the preparation of amino silicones intermediate
In the 2000ml there-necked flask of constant speed electric mixer, thermometer is housed, add 1,1,3 of the octamethylcyclotetrasiloxane (D4) of 1640g and 50 grams, 3-tetramethyl-two aminopropyl sily oxide, stir and are warmed up to 90-95 ℃ of left and right, then add 1.7g(CH
3)
4nOH content is 10% (CH
3)
4nOH alkali glue, insulation reaction 6 hours, after insulation finishes, is warmed up to 135 ℃, is incubated 1 hour, by catalyzer (CH
3)
4nOH fully decomposes, and slowly vacuumizes, and has a large amount of low-boiling-point substances to flow out, and in temperature, is 150 ℃, and relative vacuum degree be-condition of 99.9KPa, pull out low-boiling-point substance 1 hour, until there is no material outflow.Synthetic product is colorless transparent viscous liquid, and ammonia value is: 0.26mmol/g, viscosity is: 100-110cs, fugitive constituent is :≤1%.
embodiment 2-1 end epoxidized polyether and α, the preparation of omega-amino-polysiloxane intermediate block polymerization
Constant speed electric mixer is being housed, in the 2000ml there-necked flask of thermometer, the α that adds 800g embodiment 1-1 to prepare, omega-amino-polysiloxane intermediate, (the pfpe molecule amount of end epoxidized polyether is 920 to the end epoxidized polyether of 106g, a+b=3, n=14), the ethylene glycol monobutyl ether of 604g, open and stir, fully stir after 30 minutes, slowly be warmed up to 80-85 ℃ of left and right, insulation reaction 20 hours, can obtain transparent flaxen polysiloxane, amino, the organopolysiloxane polyether block copolymer of polyethers ternary block, viscosity is 500-550cs, solid content is 60 ± 1%.
embodiment 2-2 end epoxidized polyether and α, the preparation of omega-amino-polysiloxane intermediate block polymerization
Constant speed electric mixer is being housed, in the 2000ml there-necked flask of thermometer, the α that adds 800g embodiment 1-1 to prepare, omega-amino-polysiloxane intermediate, (the pfpe molecule amount of end epoxidized polyether is 1850 to the end epoxidized polyether of 214g, a+b=3, n=34-36), the ethylene glycol monobutyl ether of 676g, open and stir, fully stir after 30 minutes, slowly be warmed up to 80-85 ℃ of left and right, insulation reaction 20 hours, can obtain transparent flaxen polysiloxane, amino, the organopolysiloxane polyether block copolymer of polyethers ternary block, viscosity is 600-650cs, solid content is 60 ± 1%.
embodiment 2-3 end epoxidized polyether and α, the preparation of omega-amino-polysiloxane intermediate block polymerization
Constant speed electric mixer is being housed, in the 2000ml there-necked flask of thermometer, the α that adds 800g embodiment 1-2 to prepare, omega-amino-polysiloxane intermediate, (the pfpe molecule amount of end epoxidized polyether is 920 to the end epoxidized polyether of 96g, a+b=3, n=14), the ethylene glycol monobutyl ether of 597g, open and stir, fully stir after 30 minutes, slowly be warmed up to 80-85 ℃ of left and right, insulation reaction 20 hours, can obtain transparent flaxen polysiloxane, amino, the organopolysiloxane polyether block copolymer of polyethers ternary block, viscosity is 800-850cs, solid content is 60 ± 1%.
embodiment 2-4 end epoxidized polyether and α, the preparation of omega-amino-polysiloxane intermediate block polymerization
Constant speed electric mixer is being housed, in the 2000ml there-necked flask of thermometer, the α that adds 800g embodiment 1-2 to prepare, omega-amino-polysiloxane intermediate, (the pfpe molecule amount of end epoxidized polyether is 1850 to the end epoxidized polyether of 193g, a+b=3, n=34-36), the ethylene glycol monobutyl ether of 662g, open and stir, fully stir after 30 minutes, slowly be warmed up to 80-85 ℃ of left and right, insulation reaction 20 hours, can obtain transparent flaxen polysiloxane, amino, the organopolysiloxane polyether block copolymer of polyethers ternary block, viscosity is 875-900cs, solid content is 60 ± 1%.
the cation-modified preparation of embodiment 3-1 organopolysiloxane polyether block copolymer
On the basis that completes embodiment 2-1, directly add the monochloroethane of 18g, after fully stirring, stir and be warmed up to 95-100 ℃ of left and right, insulation reaction 4 hours, get final product to obtain the super soft hydrophilic block silicone oil of faint yellow transparent viscous fluid, viscosity is 600cs, and solid content is 60 ± 1%.
the cation-modified preparation of embodiment 3-2 organopolysiloxane polyether block copolymer
On the basis that completes embodiment 2-2, directly add the monochloroethane of 18g, after fully stirring, stir and be warmed up to 95-100 ℃ of left and right, insulation reaction 4 hours, get final product to obtain the super soft hydrophilic block silicone oil of faint yellow transparent viscous fluid, viscosity is 715cs, and solid content is 60 ± 1%.
the cation-modified preparation of embodiment 3-3 organopolysiloxane polyether block copolymer
On the basis that completes embodiment 2-3, directly add the monochloroethane of 13.5g, after fully stirring, stir and be warmed up to 95-100 ℃ of left and right, insulation reaction 4 hours, get final product to obtain the super soft hydrophilic block silicone oil of faint yellow transparent viscous fluid, viscosity is 905cs, and solid content is 60 ± 1%.
the cation-modified preparation of embodiment 3-4 organopolysiloxane polyether block copolymer
On the basis that completes embodiment 2-4, directly add the monochloroethane of 13.5g, after fully stirring, stir and be warmed up to 95-100 ℃ of left and right, insulation reaction 4 hours, get final product to obtain the super soft hydrophilic block silicone oil of faint yellow transparent viscous fluid, viscosity is 1000cs, and solid content is 60 ± 1%.
To above-described embodiment 3-X(X=1-4) product of producing carries out the detection of the contrast of effect and physics, chemical stability:
1, the preparation of finishing composition
Get above-described embodiment 3-X(X=1-4) the prepared content product 100g that is 60%, while stirring, slowly add water, the amount of water is 500g, opens the emulsion of the zona pellucida blue light that rare one-tenth content is 10% left and right, finally add 2g Glacial acetic acid, pH value is adjusted between 5-6.
2, the application art of finishing composition
Process fabric: cotton bleaching Woven Fabrics, T/C bleach looped fabric, entirely wash and bleach looped fabric, terylene lint
Treatment process: consumption 10g/L
3, the contrast of result of use
In the contrast of result of use, mainly carry out the mensuration of the contrast of feel, hydrophilic contrast, xanthochromia.
The contrast of 3.1 feels
The effect of the processing fabric of softening agent feels that by the mode touching with hand the composite factors such as loft after fabric treating, pliability, rebound resilience and smooth degree evaluate, feel is divided into 5 each grades, rank is more high better, 5 grades best, 1 grade minimum, and in table 1, feel level data has evaluating and draw with hand touch of experience technician by five.
3.2 hydrophilic contrasts
With standard dropper, from the fabric face of sprawling to level from fabric 10cm At The Height, drip 1 and drip, measure 1 and drip complete wetting, diffusion, infiltration time used on fabric face from quiescent conditions, the time used is shorter, illustrates that its hydrophilic effect is better.
The mensuration of 3.3 xanthochromias
Bleached woven fabric (former cloth) before not processing through finishing composition is measured the whiteness of fabric face by whiteness instrument, fabric is measured the whiteness of fabric face after finishing composition is processed sizing by whiteness instrument, by the contrast of two whiteness values, carry out the xanthochromia of evaluation agent, value difference is less, and the yellowing resistance of finishing composition can be better.
Table 1 result of use comparative evaluation
4, the detection of physics, chemical stability
The evaluation of table 2 stability
Ratings data by table 1, table 2 can be found out, adopt the synthetic super soft hydrophilic block silicone oil of end epoxidized polyether to process and on fabric, there is excellent soft right, fluffy, smooth feel, give fabric certain hydrophilicity simultaneously, on bleached woven fabric, substantially do not affect especially the whiteness of fabric; Aspect stability, there is excellent heat-resisting, resistance to shearing, acidproof, alkaline-resisting, salt tolerant, resistance to hard water stability, have a wide range of applications field and wide application prospect, can be thoroughly substituted-amino silicone oil comprehensively.
Claims (6)
1. cation-modified super soft hydrophilic block silicon oil compound, is characterized in that this compound has the positively charged ion of following structural formula:
Described n1 is 5 ~ 10, and described R is
, a=0 ~ 3 wherein, b=0 ~ 3, n=10 ~ 40.
2. a preparation method who prepares cation-modified super soft hydrophilic block silicon oil compound claimed in claim 1, is characterized in that the method comprises the following steps:
1) α, the preparation method of omega-amino-polysiloxane intermediate
By the octamethylcyclotetrasiloxane and 1 after dehydration, 1,3,3-tetramethyl-two aminopropyl sily oxide add in there-necked flask according to certain ratio, open to stir and be warmed up between 90-95 ℃, then add temporary basic catalyst, consumption is the 0.1-0.2% of octamethylcyclotetrasiloxane quality, insulation reaction 5-6 hour between 90-95 ℃; After insulation finishes, be warmed up to 130-140 ℃, be incubated 1 hour, basic catalyst is fully decomposed; Vacuumize the low-boiling-point substance of pulling out in reactant, between temperature is controlled 140-150 ℃, relative vacuum degree is controlled-99.8--99.9KPa, obtains the α of low boiling mixture content≤1%, omega-amino-polysiloxane intermediate;
2) end epoxidized polyether and α, the preparation method of omega-amino-polysiloxane intermediate block polymerization
To hold epoxidized polyether, α, omega-amino-polysiloxane intermediate is according to epoxy group(ing) mole number: the ratio that amino mole number is 1:1.1-1:1.2 joins in there-necked flask, add organic solvent, consumption is the 40%-50% of reactant total mass, after adding, opens and stirs, fully stir 20 ~ 30 minutes, be warmed up to 80-85 ℃, insulation reaction 15-20 hour, gets final product to obtain the organopolysiloxane polyether block copolymer of polysiloxane, amino, polyethers ternary block;
3) the cation-modified preparation method of organopolysiloxane polyether block copolymer
In step 2) on the basis of the organopolysiloxane polyether block copolymer of prepared polysiloxane, amino, polyethers ternary block, add a certain amount of alkylating reagent monochloroethane, stirring is warmed up to 95-100 ℃, and insulation reaction 3-4 hour gets final product to obtain super soft hydrophilic block silicone oil.
3. the preparation method of cation-modified super soft hydrophilic block silicon oil compound according to claim 2, is characterized in that: the basic catalyst described in step 1) is (CH
3)
4nOH alkali glue or (n-C
4h
9)
4pOH alkali glue.
4. the preparation method of cation-modified super soft hydrophilic block silicon oil compound according to claim 2, is characterized in that: step 2) described organic solvent is one or several combination of Virahol, ethylene glycol monobutyl ether, ethylene glycol ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, Diethylene Glycol, dipropylene glycol.
5. the preparation method of cation-modified super soft hydrophilic block silicon oil compound according to claim 2, is characterized in that: step 2) described in the general structure of end epoxidized polyether be:
A=0-3 wherein, b=0-3, one or more end epoxidized polyethers in n=10-40.
6. a super soft hydrophilic block sillicon oil treatment agent, this finishing composition comprises cation-modified super soft hydrophilic block silicon oil compound claimed in claim 1, the weight ratio of described cation-modified super soft hydrophilic block silicon oil compound is 1% ~ 60%.
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| CN106397776A (en) * | 2016-08-30 | 2017-02-15 | 浙江科峰有机硅有限公司 | Double amino type block polyether amino silicone oil and preparation method thereof |
| CN108951154A (en) * | 2018-05-23 | 2018-12-07 | 绍兴柯桥德美精细化工有限公司 | A kind of environment-friendly type terylene soft fabric, water repellent, anti-static multifunctional method for sorting |
| CN109280173B (en) * | 2018-09-13 | 2020-07-31 | 宁波润禾高新材料科技股份有限公司 | Super-soft hydrophilic silicone oil and preparation method thereof |
| CN111171267B (en) * | 2020-01-20 | 2022-05-31 | 宁波润禾高新材料科技股份有限公司 | High-elasticity resin modified silicone oil and preparation method thereof |
| CN114230797B (en) * | 2021-12-30 | 2023-12-01 | 江苏奥斯佳材料科技股份有限公司 | Cationic organosilicon polymer, microemulsion and preparation method thereof |
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