CN105111448B - A kind of novel siliceous softening agent and preparation method thereof - Google Patents
A kind of novel siliceous softening agent and preparation method thereof Download PDFInfo
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Abstract
The invention discloses a kind of novel siliceous softening agent and preparation method thereof, belong to printing and dyeing assistant technical field.The intermediate (I) with tertiary amine groups and pi-allyl is obtained first with dimeric dibasic acid and the reaction of N methyl diethanolamines and allyl compound, then containing hydrogen silicone oil and intermediate (I) are subjected to hydrosilylation in the presence of catalyst, it is quaternised modified using quaternizing agent progress, obtain intermediate (II).Finally in the presence of nonionic emulsifier, dimer acid modified polysiloxanes is dispersed in water a kind of obtained novel siliceous softening agent.Extensively, environmental protection, the fabric feeling after being processed is plentiful, smooth, and pliability and good endurance, the fluffy degree of fabric improve a lot for the novel siliceous softening agent raw material sources of the present invention.In addition, preparation is simple for the softening agent, cost is low, is easy to promote.
Description
Technical field
The invention belongs to printing and dyeing assistant technical field.Specifically related to a kind of novel siliceous softening agent and preparation method thereof.
Background technology
Higher required with the improvement of living standards, people there has also been to the performance of textile.Softening agent is textile
A most-often used class material in process, its main function is the interfibrous coefficient of friction of reduction, to obtain fiber surface
Soft and lubrication effect.There is polysiloxanes main chain easily to rotate and bend, and intermolecular force is small and the spy such as physiological inertia
Point, its molecular structure especially meets the mechanism of fiber softening, can significantly reduce the interfibrous quiet, coefficient of kinetic friction, thus has
Machine silicon class softening agent has turned into textile industry the class flexible material that finishing effect is the most prominent, be most widely used.At present
Modification, the application study of organic silicon softening agent are very active.Such as using small molecule organo-silicon coupling agent with silicone oil through overbalance
Active group is introduced into the molecular structure of polysiloxanes by change.Also there is the report using polyurethane-modified silicone softening agent.Plant
Thing oil is the very important lubrication softening agent of a class, strong with wide material sources, feel moisture feeling, using it is safe the features such as, but mesh
The work that preceding utilization vegetable oil is modified to silicone softening agent is very rare.
Dimer (fatty acid) yl (hereinafter referred to as dimeric dibasic acid) be by unsaturated acids (soybean oleic acid, oleic acid and linolenic acid) or
Its methyl esters is prepared by hot dimerization method, is contained in the binary acid of highest molecular mass industrially used at present, its molecule
The Long carbon chain that two carboxyls and a larger nonpolar alkyl, the branched structure of its height and 36 carbon atoms are constituted causes it
Have amorphism, high flexibility and hydrophobicity, this distinctive structure is highly suitable for producing various derivatives.At present
Report is had no using the research of dimer (fatty acid) yl modified organic silicon softening agent.
The content of the invention
The technical problems to be solved by the invention are to provide a kind of novel siliceous softening agent and preparation method thereof.Main research
Thinking is：Obtained first with dimeric dibasic acid and N methyldiethanol amine and allyl polyethenoxy ether reaction with tertiary amine groups and
The intermediate (I) of pi-allyl, then carries out hydrosilylation in the presence of catalyst by containing hydrogen silicone oil and intermediate (I),
It is quaternised modified using quaternizing agent progress, obtain a kind of dimer acid modified polysiloxanes.Then in nonionic emulsifier
In the presence of, dimer acid modified polysiloxanes is dispersed in water a kind of obtained novel siliceous softening agent.The softening agent raw material
Wide material sources, environmental protection, the fabric feeling after being processed is plentiful, smooth, pliability and good endurance, the fluffy degree of fabric
Improve a lot.In addition, preparation is simple for the softening agent, cost is low, is easy to promote.
The technical solution adopted for solving the technical problem of the present invention is：
A kind of preparation method of novel siliceous softening agent, it is characterized in that, comprise the following steps：
Step one：It is first according to mol ratio (1.5~2)：1 adds dimeric dibasic acid and N methyldiethanol amine in reactor,
Be passed through nitrogen, be warming up to 100~140 DEG C, react 2-4 hours, then add allyl polyethenoxy ether, 100~140 DEG C after
Continuous reaction 3-5 hours, in 100 DEG C of vacuum removal low-boiling-point substance 90min, is cooled to room temperature and intermediate (I) is made；
Step 2：Containing hydrogen silicone oil is added in intermediate (I), nitrogen is passed through, 10~15min is stirred, is heated to 90
~120 DEG C, catalyst is added, then 4~5h of insulation reaction adds quaternizing agent and continue to react 4~5h, de- in 90 DEG C of vacuum
Except low-boiling-point substance 60min, intermediate (II) is made；
Step 3：Under the conditions of 40~60 DEG C, nonionic emulsifier is added in intermediate (II), 30min is stirred, added
Deionized water regulation solid content is 25~30%, and is 5.0~6.0 with the pH of sour regulation system, obtains novel siliceous softening agent；
The structure of the allyl polyethenoxy ether is：
CH2=CHCH2R2H wherein R2For-O (CH2CH2O)XX=3,5,7,9,10.
Further, in step one, the mol ratio of dimeric dibasic acid and N methyldiethanol amine is (1.5~2)：1；
The mol ratio of allyl polyethenoxy ether and dimeric dibasic acid is 1:(1~1.5).
Further, the structure of dimeric dibasic acid is in step one：HOOC-R1–COOH；Wherein R1For：
Further, the hydrogen content of containing hydrogen silicone oil is 0.3~1.5% (w/w), the consumption of containing hydrogen silicone oil in step 2
For：The mol ratio of Si-H and allyl polyethenoxy ether in containing hydrogen silicone oil molecule is：0.5~1.0:1.0；
The structural formula of containing hydrogen silicone oil is：
Wherein, m, n=1,2,3,4,5
Further, catalyst described in step 2 is the aqueous isopropanol of chloroplatinic acid, and the consumption of catalyst is Silicon Containing Hydrogen
The 2.0 × 10 of oil quality-3~3.0 × 10-3%；
Further, quaternizing agent described in step 2 is one in benzyl chloride, dimethyl suflfate, ethyl chloroacetate
Kind,
The mol ratio of quaternizing agent and N methyldiethanol amine is 1:1.
Further, nonionic emulsifier is heterogeneous ten alcohol polyoxyethylene ether XP-80, isomerous tridecanol polyoxy in step 3
One kind in vinethene 1307,1310 and AEO AEO-9；
The consumption of nonionic emulsifier is the 5~20% of intermediate (II) quality；
The acid used in pH is adjusted in step 3 is：Formic acid or acetic acid.
The chemical reaction mechanism of above-mentioned preparation method is as follows：
Wherein R3For：—CH3,-CH2C6H5,-CH2COOC2H5。
Further, the invention discloses a kind of novel siliceous softening agent prepared by above-mentioned preparation method.
Further, the main component structure of novel siliceous softening agent prepared by above-mentioned preparation method is as follows：
Wherein,
M, n=1,2,3,4,5
R1For：
R2For-O (CH2CH2O)XX=3,5,7,9,10；
R3For：—CH3,-CH2C6H5,-CH2COOC2H5。
The beneficial effects of the invention are as follows：
(1) a kind of novel siliceous softening agent outward appearance prepared by the present invention is：White emulsion, pH is 5.0-6.0, and working substance contains
Measure and be：25~30%, 1:9 aqueous emulsion 24h are not stratified, and product has preferable shelf-stability, room temperature deposit 6 months it is constant
Matter, with preferable dilution-resistant stability.
(2) plant oil base long-chain hydrocarbon is both contained in molecule containing silicone softener prepared by this method, also containing polysiloxane
Segment and quaternary ammonium salt group, product have preferable dilution-resistant stability and shelf-stability.
(3) extensively, environmental protection, the fabric feeling after being processed is rich for raw material sources containing silicone softener prepared by this method
Full, smooth, pliability and good endurance, the fluffy degree of fabric improve a lot.
Embodiment
For a better understanding of the present invention, with reference to the embodiment content that the present invention is furture elucidated, but the present invention
Content is not limited solely to the following examples, and embodiment is not construed as limiting the scope of the present invention.
Embodiment 1：
Step one：112.4g dimeric dibasic acids and 11.9g N methyldiethanol amines are added and carry agitator, thermometer, temperature control
And in the reactor of condensing unit, nitrogen is passed through, stir, be warming up to 100 DEG C, react 2 hours, then add 55.6g
Allyl polyethenoxy ether (5EO-allyl polyethenoxy ether containing 5 EO), continues to react 5 hours, in 100 at 120 DEG C
DEG C vacuum removal low-boiling-point substance 90min, is cooled to room temperature and intermediate (I) is made；
Step 2：It is 0.3% (w/w) containing hydrogen silicone oil 50g that hydrogen content is added in intermediate (I), is passed through nitrogen, is stirred
10min, is heated to 90 DEG C, adds 1.0 × 10-3The aqueous isopropanol of g chloroplatinic acids, insulation reaction 4h, then adds 12.7g
Benzyl chloride continues to react 5h.Finally the vacuum removal low-boiling-point substance 60min under the conditions of 90 DEG C, is made intermediate (II).
Step 3：Under the conditions of 50 DEG C, 25g nonionic emulsifiers 1307 are added in intermediate (II), 30min is stirred,
It is 25~30% to add deionized water regulation solid content, and is 5.0~6.0 with the pH of formic acid regulation system, obtains novel siliceous
Softening agent.
Product appearance is：White emulsion, pH is 5.0-6.0, and substance content is：25~30%, 1：9 aqueous emulsion 24h are not
Layering, product has preferable shelf-stability, is never degenerated within 6 months in room temperature storage, with preferable dilution-resistant stability.
Embodiment 2：
Step one：112.4g dimeric dibasic acids and 11.9g N methyldiethanol amines are added and carry agitator, thermometer, temperature control
And in the reactor of condensing unit, nitrogen is passed through, stir, be warming up to 140 DEG C, react 3 hours, then add 99.6g
Allyl polyethenoxy ether (10EO), continues to react 6 hours at 140 DEG C, in 100 DEG C of vacuum removal low-boiling-point substance 60min, is cooled to
Intermediate (I) is made in room temperature；
Step 2：It is 0.5% (w/w) containing hydrogen silicone oil 40g that hydrogen content is added in intermediate (I), is passed through nitrogen, is stirred
10min, is heated to 90 DEG C, adds 1.2 × 10-3The aqueous isopropanol of g chloroplatinic acids, insulation reaction 5h, then adds 12.6g
Dimethyl suflfate continues to react 4h.Finally the vacuum removal low-boiling-point substance 60min under the conditions of 90 DEG C, is made intermediate (II).
Step 3：Under the conditions of 50 DEG C, 50g nonionic emulsifiers AEO-9 stirring 30min are added in intermediate (II),
It is 25~30% to add deionized water regulation solid content, and is 5.0~6.0 with the pH of formic acid regulation system, obtains novel siliceous
Softening agent.
Product appearance is：White emulsion, pH is 5.0-6.0, and substance content is：25~30%, 1：9 aqueous emulsion 24h are not
Layering, product has preferable shelf-stability, is never degenerated within 6 months in room temperature storage, with preferable dilution-resistant stability.
Embodiment 3：
Step one：168.6g dimeric dibasic acids and 23.8g N methyldiethanol amines are added and carry agitator, thermometer, temperature control
And in the reactor of condensing unit, nitrogen is passed through, stir, be warming up to 140 DEG C, react 3 hours, then add 73.2g
Allyl polyethenoxy ether (7EO), continues to react 6 hours at 125 DEG C, in 100 DEG C of vacuum removal low-boiling-point substance 60min, is cooled to
Intermediate (I) is made in room temperature；
Step 2：It is 0.4% (w/w) containing hydrogen silicone oil 50g that hydrogen content is added in intermediate (I), is passed through nitrogen, is stirred
10min, is heated to 90 DEG C, adds 1.0 × 10-3The aqueous isopropanol of g chloroplatinic acids, insulation reaction 5h, then adds 25.2g
Dimethyl suflfate continues to react 4h.Finally the vacuum removal low-boiling-point substance 60min under the conditions of 90 DEG C, is made intermediate (II).
Step 3：Under the conditions of 50 DEG C, 34g nonionic emulsifiers 1310 are added in intermediate (II) and stir 30min, plus
It is 25~30% to enter deionized water regulation solid content, and is 5.0~6.0 with the pH of formic acid regulation system, obtains novel siliceous soft
Soft dose.
Product appearance is：White emulsion, pH is 5.0-6.0, and substance content is：25~30%, 1：9 aqueous emulsion 24h are not
Layering, product has preferable shelf-stability, is never degenerated within 6 months in room temperature storage, with preferable dilution-resistant stability.
Embodiment 4：
Step one：112.4g dimeric dibasic acids and 11.9g N methyldiethanol amines are added and carry agitator, thermometer, temperature control
And in the reactor of condensing unit, nitrogen is passed through, stir, be warming up to 135 DEG C, react 3.5 hours, then add
99.6g allyl polyethenoxy ethers (10EO), continue to react 5 hours at 140 DEG C, in 100 DEG C of vacuum removal low-boiling-point substance 60min,
It is cooled to room temperature and intermediate (I) is made；
Step 2：It is 1.0% (w/w) containing hydrogen silicone oil 10g that hydrogen content is added in intermediate (I), is passed through nitrogen, is stirred
10min, is heated to 90 DEG C, adds 3 × 10-4Then the aqueous isopropanol of g chloroplatinic acids, insulation reaction 5h adds 12.2g chlorine
Ethyl acetate continues to react 4h.Finally the vacuum removal low-boiling-point substance 60min under the conditions of 90 DEG C, is made intermediate (II).
Step 3：Under the conditions of 50 DEG C, 15g nonionic emulsifiers XO-80 stirring 30min are added in intermediate (II),
It is 25~30% to add deionized water regulation solid content, and is 5.0~6.0 with the pH of acetic acid regulation system, obtains novel siliceous
Softening agent.
Product appearance is：White emulsion, pH is 5.0-6.0, and substance content is：25~30%, 1：9 aqueous emulsion 24h are not
Layering, product has preferable shelf-stability, is never degenerated within 6 months in room temperature storage, with preferable dilution-resistant stability.
Embodiment 5：
Step one：168.6g dimeric dibasic acids and 23.8g N methyldiethanol amines are added and carry agitator, thermometer, temperature control
And in the reactor of condensing unit, nitrogen is passed through, stir, be warming up to 115 DEG C, react 5 hours, then add 90.8g
Allyl polyethenoxy ether (9EO), continues to react 6 hours at 140 DEG C, in 100 DEG C of vacuum removal low-boiling-point substance 60min, is cooled to
Intermediate (I) is made in room temperature；
Step 2：It is 1.0% (w/w) containing hydrogen silicone oil 15g that hydrogen content is added in intermediate (I), is passed through nitrogen, is stirred
10min, is heated to 90 DEG C, adds 3 × 10-4Then the aqueous isopropanol of g chloroplatinic acids, insulation reaction 5h adds 25.2g chlorine
Change benzyl to continue to react 4h.Finally the vacuum removal low-boiling-point substance 60min under the conditions of 90 DEG C, is made intermediate (II).
Step 3：Under the conditions of 50 DEG C, 60g nonionic emulsifiers XP80 stirring 30min are added in intermediate (II), plus
It is 25~30% to enter deionized water regulation solid content, and is 5.0~6.0 with the pH of formic acid regulation system, obtains novel siliceous soft
Soft dose.
Product appearance is：White emulsion, pH is 5.0-6.0, and substance content is：25~30%, 1：9 aqueous emulsion 24h are not
Layering, product has preferable shelf-stability, is never degenerated within 6 months in room temperature storage, with preferable dilution-resistant stability.
Embodiment 6：
A kind of application process of novel siliceous softening agent is as follows：
5~30g/L the aqueous solution will be made into containing silicone softener, be arranged according to following finishing technique：Pure cotton fabric soaks
Roll (liquor ratio 1:20, two leachings two are rolled) → preliminary drying (105 DEG C, 2min) → bake (150 DEG C, 2min) → washing → drying.
Claims (10)
1. a kind of preparation method of novel siliceous softening agent, it is characterized in that, comprise the following steps：
Step one：It is first according to mol ratio (1.5~2)：1 adds dimeric dibasic acid and N methyldiethanol amine in reactor, is passed through
Nitrogen, is warming up to 100~140 DEG C, reacts 2-4 hours, then adds allyl polyethenoxy ether, continues anti-at 100~140 DEG C
Answer 3-5 hours, in 100 DEG C of vacuum removal low-boiling-point substance 90min, be cooled to room temperature and intermediate (I) is made；
Step 2：Containing hydrogen silicone oil is added in intermediate (I), nitrogen is passed through, 10~15min is stirred, is heated to 90~120
DEG C, catalyst is added, then 4~5h of insulation reaction adds quaternizing agent and continue to react 4~5h, low in 90 DEG C of vacuum removals
Thing 60min is boiled, intermediate (II) is made；
Step 3：Under the conditions of 40~60 DEG C, nonionic emulsifier is added in the intermediate (II), 30min is stirred, addition go from
Sub- water regulation solid content is 25~30%, and is 5.0~6.0 with the pH of sour regulation system, obtains novel siliceous softening agent；
The structure of the allyl polyethenoxy ether is：
CH2=CHCH2R2H wherein R2For-O (CH2CH2O)XX=3,5,7,9 or 10.
2. a kind of preparation method of novel siliceous softening agent according to claim 1, it is characterized in that,
In step one, the mol ratio of dimeric dibasic acid and N methyldiethanol amine is (1.5~2)：1；
The mol ratio of allyl polyethenoxy ether and dimeric dibasic acid is 1:(1~1.5).
3. a kind of preparation method of novel siliceous softening agent according to claim 1, it is characterized in that,
The structure of dimeric dibasic acid is in step one：HOOC-R1–COOH；Wherein R1For：
4. a kind of preparation method of novel siliceous softening agent according to claim 1, it is characterized in that,
The hydrogen content of containing hydrogen silicone oil is 0.3~1.5% (w/w) in step 2, and the consumption of containing hydrogen silicone oil is：Containing hydrogen silicone oil molecule
In Si-H and the mol ratio of allyl polyethenoxy ether be：0.5~1.0:1.0；
The structural formula of containing hydrogen silicone oil is：
Wherein, m, n=1-5
5. a kind of preparation method of novel siliceous softening agent according to claim 1, it is characterized in that,
Catalyst described in step 2 is the aqueous isopropanol of chloroplatinic acid, the consumption of catalyst for containing hydrogen silicone oil quality 2.0 ×
10-3~3.0 × 10-3%.
6. a kind of preparation method of novel siliceous softening agent according to claim 1, it is characterized in that,
Quaternizing agent described in step 2 is one kind in benzyl chloride, dimethyl suflfate, ethyl chloroacetate.
7. a kind of preparation method of novel siliceous softening agent according to claim 1, it is characterized in that,
The mol ratio of quaternizing agent and N methyldiethanol amine is 1:1.
8. a kind of preparation method of novel siliceous softening agent according to claim 1, it is characterized in that,
In step 3 nonionic emulsifier be heterogeneous ten alcohol polyoxyethylene ether XP-80, isomerous tridecanol polyoxyethylene ether 1307,
One kind in 1310 and AEO AEO-9；
The consumption of nonionic emulsifier is the 5~20% of intermediate (II) quality；
The acid used in pH is adjusted in step 3 is：Formic acid or acetic acid.
9. a kind of novel siliceous softening agent prepared according to any described preparation methods of claim 1-8.
10. novel siliceous softening agent according to claim 9, it is characterized in that, its main component structure is as follows：
Wherein,
M, n=1-5
R1For：
R2For-O (CH2CH2O)XX=3,5,7,9 or 10；
R3For：—CH3,-CH2C6H5,-CH2COOC2H5。
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| CN106589385A (en) * | 2017-01-05 | 2017-04-26 | 佛山市顺德区德美瓦克有机硅有限公司 | Low-yellowing quaternary ammonium type hydrophilic amino-modified silicone oil emulsion and preparation method thereof |
| CN109252418A (en) * | 2018-08-09 | 2019-01-22 | 黄勇 | A kind of preparation method of paper pulp fluff type softening agent |
| CN109468834A (en) * | 2018-09-30 | 2019-03-15 | 杭州创屹机电科技有限公司 | A kind of biomass-based linen-cotton softening agent |
| CN110983787B (en) * | 2019-12-17 | 2022-02-11 | 广东新翔星科技股份有限公司 | Hydrophilic thickening organosilicon softening agent and preparation method thereof |
| CN113549220A (en) * | 2021-08-04 | 2021-10-26 | 广东新翔星科技股份有限公司 | Modified hydrogen-containing silicone oil and preparation method and application thereof |
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