CN106381715A - Quaternary ammonium modified block polyether/amino silicone oil and preparation method thereof - Google Patents
Quaternary ammonium modified block polyether/amino silicone oil and preparation method thereof Download PDFInfo
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- CN106381715A CN106381715A CN201610783241.7A CN201610783241A CN106381715A CN 106381715 A CN106381715 A CN 106381715A CN 201610783241 A CN201610783241 A CN 201610783241A CN 106381715 A CN106381715 A CN 106381715A
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- silicone oil
- block polyether
- amino silicone
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- polyether amino
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Classifications
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/643—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
- D06M15/647—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain containing polyether sequences
-
- 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
- C08G77/42—Block-or graft-polymers containing polysiloxane sequences
- C08G77/46—Block-or graft-polymers containing polysiloxane sequences containing polyether sequences
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
- D06M2200/50—Modified hand or grip properties; Softening compositions
Abstract
The invention relates to quaternary ammonium modified block polyether/amino silicone oil and a preparation method thereof. The preparation method comprises the following steps: bis(glycidoxy-terminal), DMC and an organic solvent, adding an alkaline catalyst, heating to 80-110 DEG C, and balancing for 6-8 h; heating to about 140 DEG C to decompose the catalyst for 1-2 h, and carrying out underpressure distillation to obtain colorless or flavescent epoxy-terminated silicone oil; uniformly mixing the epoxy-terminated silicone oil, polyetheramine and a solvent, reacting at 60-80 DEG C for 15-20 h to prepare a block polyether/amino silicone oil prepolymer; and respectively adding a tertiary amine compound and equimolar quantity of organic acid into the product obtained in the step b, continuously reacting at 70-80 DEG C for 4-8h so as to obtain the final product. The amino silicon oil prepared by the method has excellent hand feeling, has little influence on whiteness and hydrophilicity of fabrics, can completely replace common amino silicon oil, and has an excellent application prospect.
Description
Technical field
The invention belongs to spinning post-finishing auxiliary agent field, particularly to a kind of quaternised modified block polyether amino silicone oil and
Its preparation method.
Background technology
Stability of emulsion is poor due to existing for common amido silicon oil, the easy yellowing of the fabric after process, moisture absorbing and sweat releasing property difference
Shortcoming, is progressively substituted by various types of block polyether modified amino silicon oils.Due to the introducing of hydrophilic polyether segment, emulsion
Good stability.And, polyether segment is embedded in the structure of the main chain film property on polysiloxanes on fabric fibre to be affected relatively
Little it is easy to play its soft, smooth, fluffy performance.This is that block polyether amino silicone oil is had with respect to common amido silicon oil
Some advantages.
However, the amido functional group in block polyether amino silicone oil is only distributed in the two ends of polysiloxanes segment, by structure
Impact, ammonia value can not arbitrarily change.Polysiloxanes segment is longer, and ammonia value is just little.And ammonia value will be improved, poly- silica can only be reduced
The molecular weight of alkane segment.This contradiction limits the raising further of block polyether amino silicone oil feel.
Content of the invention
The invention provides a kind of feel is excellent, emulsion-stabilizing, color inhibition and have necessarily hydrophilic quaternised modified
Block polyether amino silicone oil.
Present invention also offers the preparation method of described quaternised modified block polyether amino silicone oil.
The technical solution adopted for the present invention to solve the technical problems is：
A kind of quaternised modified block polyether amino silicone oil, the structural formula of this compound is following (structural formula I)：
Wherein, EO is-CH2CH2O-, PO are-CH (CH3)CH2O-, n be 50～500, a be 5～60, b be 0～8, m be 2
～20.
Preferably, described R is methyl, ethyl, propyl group, butyl, hexyl, octyl group, decyl, dodecyl, the tetradecane
One or more of base, cetyl, octadecyl.
Preferably, n is 100～300, a is 2～6 for 10～50, b.
A kind of preparation method of quaternised modified block polyether amino silicone oil, the method comprises the following steps：
A, the synthesis of end epoxy silicon oil
By epoxy double-seal head, organosiloxane ring body (DMC) and organic solvent mix homogeneously, add base catalyst, rise
Temperature, to 80 DEG C～110 DEG C, reacts 6～8h；Then heat to 140～150 DEG C of reaction 1h～2h with decomposition catalyst, vacuum distillation
Remove solvent and low-boiling-point substance, obtaining outward appearance is colourless or flaxen end epoxy silicon oil；
B, the synthesis of block polyether amino silicone oil
The end epoxy silicon oil that step a is obtained, is mixed homogeneously with polyetheramine (structure formula II) and solvent, at 60 DEG C～80 DEG C
Reaction 15～20h, that is, be obtained block polyether amino silicone oil；
C, block polyether amino silicone oil quaternized
The organic acid of tertiary amine compound, equimolar amountss is added separately in the product that step b obtains, continue 70 DEG C～
80 DEG C of reaction 4～8h, that is, obtain final products.
Preferably, described base catalyst is (CH3)4NOH alkali glue or (n-C4H9)4POH alkali glue, base catalyst is used
Amount (effective content of catalyst) is the 0.01%～0.05% of reactant gross mass；Described organic solvent is N- methylpyrrole
Alkanone, DMF, one or more of N,N-dimethylacetamide, consumption is reaction system gross mass
5%～20%.
Preferably, in step a, the mass ratio of epoxy double-seal head and organosiloxane ring body (DMC) is 1:10～100.
Preferably mass ratio is 1:20～60.
Preferably, polyetheramine and the amount ratio of the material of end epoxy silicon oil are for 0.8～1 in step b:1.Polyetheramine and end ring
The amount ratio preferably 0.9～1 of the material of oxygen silicone oil:1.
Preferably, the solvent described in step b is isopropanol, ethylene glycol monobutyl ether, ethylene glycol ether, ethylene glycol list
The combination of one or more of ether, glycol monoethyl ether and diethylene glycol monomethyl ether.
Preferably, the organic acid described in step c is acetic acid or lauric acid.
Preferably, the tertiary amine compound described in step c is trimethylamine, N, N- dimethyl amine, N, N- dimethyl n
Propylamine, N, N- dimethyl n butylamine, N, N- dimethylhexylamine, N, N- dimethyl octylame, N, N- dimethyldodecyl amide, dodecyl two
One of methyl tertiary amine, dodecyldimethylamine base tertiary amine, hexadecyldimethyl benzyl ammonium tertiary amine, octadecyldimethyl tertiary amine or several
Kind.
The present invention compared with prior art has advantages below：
1) to prepare end epoxy silicon oil by the way of epoxy double-seal head and the direct chain extension of organosilicon ring body, and first to synthesize end
Containing hydrogen silicone oil, then carry out Si-H addition reaction and introduce the method for epoxy radicals comparing, the epoxide group retention rate of product is high, in big point of preparation
During the end epoxy silicon oil of son amount, this advantage is particularly evident.
2) present invention on the premise of preparing block polyether amino silicone oil, part amino has been carried out quaternized sun from
Son is modified, improves polarity, reactivity and the adsorptivity of product.Compare in undressed common block polyether silicone oil, feel
More preferably, range of application is wider, is widely used in natural, artificial and blend fibre hand feel finishing.Quaternary ammonium salt and the affine work of water
With strong, improve hydrophilic and the antistatic behaviour of fabric；Additionally, the active hydrogen on amino in silicone oil reduces, also improve product
Yellowing resistance.
Specific embodiment
Below by specific embodiment, technical scheme is described in further detail.It should be appreciated that this
Bright enforcement is not limited to the following examples, and any pro forma flexible and/or change that the present invention is made all will fall
Enter the scope of the present invention.
In the present invention, if not refering in particular to, all of part, percentage ratio are unit of weight, the equipment being adopted and raw material etc.
All it is commercially available or commonly used in the art.Method in following embodiments, if no special instructions, is the normal of this area
Rule method.
Embodiment 1：
By 20g epoxy double-seal head, 490g organosiloxane ring body (DMC) and 35gN, N- dimethyl acetylamide mix homogeneously,
Add 0.1g (CH3)4NOH (is added) in the form of alkali glue, is warming up to 100 DEG C, balances 8h；Then heat to 140 DEG C about decomposition
Catalyst 2h, vacuum distillation removes solvent and low-boiling-point substance, and obtaining outward appearance is colourless or flaxen end epoxy silicon oil；By upper step system
The end epoxy silicon oil obtaining, 44.5g polyetheramine (molecular weight is 900) and 370g isopropanol mix homogeneously, react 15h at 75 DEG C, that is,
Prepared block polyether amino silicone oil；By 3.5g octadecyldimethyl tertiary amine, 0.68g acetic acid adds in reaction system, at 80 DEG C
Reaction 6h, that is, be obtained final product.
Embodiment 2：
By 30g epoxy double-seal head, 915g organosiloxane ring body (DMC) and 60gN, N- dimethyl acetylamide mix homogeneously,
Add 0.2g (CH3)4NOH (is added) in the form of alkali glue, is warming up to 100 DEG C, balances 8h；Then heat to 140 DEG C about decomposition
Catalyst 2h, vacuum distillation removes solvent and low-boiling-point substance, and obtaining outward appearance is colourless or flaxen end epoxy silicon oil；By upper step system
The end epoxy silicon oil obtaining, 67g polyetheramine (molecular weight is 900) and 675g isopropanol mix homogeneously, react 15h at 75 DEG C, that is, make
Obtain block polyether amino silicone oil；By 3.75g Dodecyl Dimethyl Amine, 1g acetic acid adds in reaction system, reacts at 80 DEG C
6h, that is, be obtained final product.
Embodiment 3：
By 20g epoxy double-seal head, 735g organosiloxane ring body (DMC) and 50gN, N- dimethyl acetylamide mix homogeneously,
Add 0.15g (CH3)4NOH (is added) in the form of alkali glue, is warming up to 100 DEG C, balances 8h；Then heat to 140 DEG C about points
Solution catalyst 2h, vacuum distillation removes solvent and low-boiling-point substance, and obtaining outward appearance is colourless or flaxen end epoxy silicon oil；By upper step
Prepared end epoxy silicon oil, 99.5g polyetheramine (molecular weight is 2000), 700g isopropanol and the mixing of 350g ethylene glycol monobutyl ether are all
Even, react 15h at 75 DEG C, that is, block polyether amino silicone oil is obtained；By 3.5g octadecyldimethyl tertiary amine, 0.68g acetic acid adds
Enter in reaction system, react 6h at 80 DEG C, that is, final product is obtained.
Embodiment 4：
By 40g epoxy double-seal head, 1715g organosiloxane ring body (DMC) and 120gN, the mixing of N- dimethyl acetylamide is all
Even, add 0.3g (CH3)4NOH (is added) in the form of alkali glue, is warming up to 100 DEG C, balances 8h；Then heat to 140 DEG C about
Decomposition catalyst 2h, vacuum distillation removes solvent and low-boiling-point substance, and obtaining outward appearance is colourless or flaxen end epoxy silicon oil；Will be upper
The end epoxy silicon oil that step is obtained, 199g polyetheramine (molecular weight is 2000), 1600g isopropanol and the mixing of 600g ethylene glycol monobutyl ether
Uniformly, react 15h at 75 DEG C, that is, block polyether amino silicone oil is obtained；By 4.7g octadecyldimethyl tertiary amine, 1.25g acetic acid
Add in reaction system, react 6h at 80 DEG C, that is, final product is obtained.
The preparation of finishing agent：
The said goods are stirred with a small amount of nonionic emulsifier, is then slowly added into while stirring containing glacial acetic acid
Water, opens the emulsion of dilute one-tenth 10wt.%, finally adjusts pH to 6 about with glacial acetic acid.
The technique for applying of finishing agent：
Process fabric：Ployester/Cotton Twill Fabric,
Handling process：Consumption 30g/L,
One immersing and rolling (pick-up：70%) → drying and shaping (150 DEG C × 60S) → cooling moisture regain → performance evaluation；
Performance test with compare：
Feel：Touch rating method using many staff, be divided into 1～5 grade, numerical value is more big more soft；Whiteness：Surveyed by whiteness instrument
Fixed, less with the difference of former cloth, illustrate that yellowing resistance is better；Hydrophilic：With standard dropper from certain height drip water in
Fabric face, observes the time required in the infiltration of fabric face complete wetting for the water droplet, and the time is shorter, illustrates that hydrophilic is better；
Test result is shown in Table 1.Stability test：Main test resistance to acids and bases, endurance of cutting, salt tolerance.Test result is shown in Table 1
Table 1 use limits table
| Sample sequence number | Feel rank | Whiteness | Hydrophilic |
| Former cloth | 1 | 90.6 | 40s |
| Embodiment 1 | 4 | 85.4 | 37s |
| Embodiment 2 | 4.5 | 87.2 | 49s |
| Embodiment 3 | 4.5 | 88.3 | 43s |
| Embodiment 4 | 4 | 89.1 | 45s |
| Common amido silicon oil | 4 | 80.3 | Water repellent |
Table 2 stability evaluation table
Can be seen that have according to the quaternised modified block polyether amino silicone oil of present invention preparation from above test data
Excellent feel, less on the whiteness of fabric, hydrophilic impact, there is excellent resistance to acids and bases, endurance of cutting and salt tolerant simultaneously
Property, common amido silicon oil can be replaced completely, there is splendid application prospect.
Embodiment described above is one kind preferably scheme of the present invention, not the present invention is made any pro forma
Limit, also have other variants and remodeling on the premise of without departing from the technical scheme described in claim.
Claims (10)
1. a kind of quaternised modified block polyether amino silicone oil it is characterised in that：Following (the structural formula of the structural formula of this compound
Ⅰ)：
Wherein, EO is-CH2CH2O-, PO are-CH (CH3)CH2O-, n be 50～500, a be 5～60, b be 0～8, m be 2～20.
2. quaternised modified block polyether amino silicone oil according to claim 1 it is characterised in that：Described R be methyl,
One of ethyl, propyl group, butyl, hexyl, octyl group, decyl, dodecyl, myristyl, cetyl, octadecyl or several
Kind.
3. quaternised modified block polyether amino silicone oil according to claim 1 it is characterised in that：N is 100～300, a
It is 2～6 for 10～50, b.
4. a kind of preparation method of the quaternised modified block polyether amino silicone oil described in claim 1 is it is characterised in that the party
Method comprises the following steps：
A, the synthesis of end epoxy silicon oil
By epoxy double-seal head, organosiloxane ring body (DMC) and organic solvent mix homogeneously, add base catalyst, be warming up to
80 DEG C～110 DEG C, react 6～8h；Then heat to 140～150 DEG C of reaction 1h～2h with decomposition catalyst, vacuum distillation removes
Solvent and low-boiling-point substance, obtaining outward appearance is colourless or flaxen end epoxy silicon oil；
B, the synthesis of block polyether amino silicone oil
The end epoxy silicon oil that step a is obtained, is mixed homogeneously with polyetheramine (structure formula II) and solvent, reacts at 60 DEG C～80 DEG C
15～20h, prepared block polyether amino silicone oil；
C, block polyether amino silicone oil quaternized
The organic acid of tertiary amine compound, equimolar amountss is added separately in the product that step b obtains, continues at 70 DEG C～80 DEG C
Reaction 4～8h, that is, obtain final products.
5. preparation method according to claim 4 it is characterised in that：In step a, described base catalyst is (CH3)4NOH alkali glue or (n-C4H9)4POH alkali glue, base catalyst consumption (effective content of catalyst) is reactant gross mass
0.01%～0.05%；Described organic solvent is N-Methyl pyrrolidone, DMF, N, N- dimethylacetamide
One or more of amine, consumption is the 5%～20% of reaction system gross mass.
6. preparation method according to claim 4 it is characterised in that：Epoxy double-seal head and organosiloxane ring body (DMC)
Mass ratio be 1:10～100.
7. preparation method according to claim 4 it is characterised in that：Polyetheramine and the material holding epoxy silicon oil in step b
Amount than for 0.8～1:1.Polyetheramine with end epoxy silicon oil material amount ratio preferably 0.9～1:1.
8. preparation method according to claim 4 it is characterised in that：Solvent described in step b is isopropanol, ethylene glycol
One or more of monobutyl ether, ethylene glycol ether, ethylene glycol monoethyl ether, glycol monoethyl ether and diethylene glycol monomethyl ether
Combination；Organic acid described in step c is acetic acid or lauric acid.
9. preparation method according to claim 4 it is characterised in that：Tertiary amine compound described in step c be trimethylamine,
N, N- dimethyl amine, N, N- dimethyl n propylamine, N, N- dimethyl n butylamine, N, N- dimethylhexylamine, N, N- dimethyl-octa
Amine, N, N- dimethyldodecyl amide, Dodecyl Dimethyl Amine, dodecyldimethylamine base tertiary amine, hexadecyldimethyl benzyl ammonium tertiary amine, ten
One or more of eight alkyl dimethyl tertiary amide.
10. the quaternised modified block polyether amino silicone oil described in a kind of claim 1 is in terms of preparing textile finishing agent
Application.
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| CN107383374A (en) * | 2017-08-30 | 2017-11-24 | 嘉兴固高日化有限公司 | A kind of preparation method of bafta hydrophilic softening agent |
| CN107814941A (en) * | 2017-11-13 | 2018-03-20 | 清远市宏图助剂有限公司 | A kind of microwave preparation of the quaternized block organosilicon polymer of smooth type |
| CN108219147A (en) * | 2018-01-04 | 2018-06-29 | 佛山市三水古闰纺织印染研究院有限公司 | A kind of preparation method of hydrophilic silicone oil |
| CN108530635A (en) * | 2017-03-01 | 2018-09-14 | 射阳天源化工有限公司 | A kind of manufacturing method of the hydrophilic block silicone oil of quaternary ammonium salt sealing end |
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| CN110820353A (en) * | 2019-10-24 | 2020-02-21 | 苏州联胜化学有限公司 | Hydrophilic silicone oil and preparation method thereof |
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| CN113512199A (en) * | 2021-08-16 | 2021-10-19 | 广东传化富联精细化工有限公司 | High-purity epoxy-terminated silicone oil and preparation method thereof |
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| CN115181274A (en) * | 2022-06-29 | 2022-10-14 | 浙江科峰有机硅股份有限公司 | Super-soft and smooth block polyether amino silicone oil and preparation method thereof |
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| CN115975205A (en) * | 2023-01-29 | 2023-04-18 | 厦门弘嘉顺逸科技有限公司 | Preparation method of self-emulsifying amino silicone oil and amino silicone oil emulsion |
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Application publication date: 20170208 |