CN105111448A - Novel silicon-containing softening agent and preparation method thereof - Google Patents
Novel silicon-containing softening agent and preparation method thereof Download PDFInfo
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- CN105111448A CN105111448A CN201510640380.XA CN201510640380A CN105111448A CN 105111448 A CN105111448 A CN 105111448A CN 201510640380 A CN201510640380 A CN 201510640380A CN 105111448 A CN105111448 A CN 105111448A
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Abstract
The invention discloses a novel silicon-containing softening agent and a preparation method thereof, belonging to the technical field of printing and dyeing auxiliaries. The preparation method comprises the following steps: reacting dimer acid with N-methyldiethanolamine and an allyl compound to obtain an intermediate (I) with a tertiary amine group and allyl; then, carrying out hydrosilylation on hydrogen-containing silicon oil and the intermediate (I) under the action of a catalyst; carrying out quaternized modification by using a quaternization reagent to obtain an intermediate (II); and finally, dispersing polysiloxane modified by the dimer acid in water to prepare a novel silicon-containing softening agent under the action of a non-ionic emulsifier. The novel silicon-containing softening agent disclosed by the invention is wide in source of raw materials, as well as green and environment-friendly; a fabric processed by the softening agent is plump and smooth in handfeel and good in softness and durability, and the bulkiness of the fabric is greatly improved. In addition, the preparation process of the softening agent is simple and feasible, low in cost and convenient to generalize.
Description
Technical field
The invention belongs to dyeing and printing auxiliary technical field.Be specifically related to a kind of Novel siliceous softening agent and preparation method thereof.
Background technology
Along with growth in the living standard, the performance of people to textiles there has also been requirement higher.Softening agent is the class material the most often used in textile processing, and its Main Function reduces interfibrous frictional coefficient, to obtain the effect that fiber surface is soft and lubricate.Polysiloxane has main chain and easily rotates and bend, the features such as the little and physiological inertia of Intermolecular Forces, its molecular structure meets the mechanism of fiber softening especially, significantly can reduce interfibrous quiet, kinetic friction coefficient, thus silicone based softening agent has become the class flexible material that finishing effect in textile industry is given prominence to the most, is most widely used.Modification, the applied research of current silicone based softening agent are very active.Active group is introduced in the molecular structure of polysiloxane through equilibration as adopted small molecules organo-silicon coupling agent and silicone oil.Also the report utilizing polyurethane-modified silicone softening agent is had.Vegetables oil is the very important lubrication softening agent of a class, have wide material sources, feel moisture feeling is strong, the features such as use safety, but the work utilizing vegetables oil to carry out modification to silicone softening agent is at present very rare.
Dimer (fatty acid) yl (hereinafter referred to as dimeracid) be by unsaturated acid (soybean oleic acid, oleic acid and linolenic acid) or its methyl esters standby by hot dimerization legal system, it is the diprotic acid of the best result protonatomic mass of current industrial use, containing two carboxyls and a larger nonpolar alkyl in its molecule, the branched structure of its height and the Long carbon chain of 36 carbon atom formations make it have amorphism, high flexibility and hydrophobicity, and this distinctive structure is highly suitable for producing various derivative.The research of dimer (fatty acid) yl modified organic silicon softening agent is utilized to have no report at present.
Summary of the invention
Technical problem to be solved by this invention is to provide a kind of Novel siliceous softening agent and preparation method thereof.Main Research Thinking is: first utilize dimeracid and N methyldiethanol amine and allyl polyethenoxy ether to be obtained by reacting with tertiary amine groups and allylic intermediate (I), then under the effect of catalyzer, containing hydrogen silicone oil and intermediate (I) are carried out addition reaction of silicon with hydrogen, utilize quaternizing agent to carry out quaternised modified, obtain a kind of dimer acid modified polysiloxane.Then, under the effect of nonionic emulsifying agent, dimer acid modified polysiloxane is scattered in obtained a kind of Novel siliceous softening agent in water.These softening agent raw material sources are extensive, environmental protection, and the fabric feeling after wherethrough reason is plentiful, smooth, and pliability and good endurance, the loft of fabric improves a lot.In addition, preparation is simple for this softening agent, and cost is low, is convenient to promote.
The technical scheme that technical solution problem of the present invention is taked is:
A preparation method for Novel siliceous softening agent, is characterized in that, comprises the following steps:
Step one: first according to mol ratio (1.5 ~ 2): dimeracid and N methyldiethanol amine add in reactor by 1, pass into nitrogen, be warming up to 100 ~ 140 DEG C, reaction 2-4 hour, then allyl polyethenoxy ether is added, continue reaction 3-5 hour at 100 ~ 140 DEG C, in 100 DEG C of vacuum removal low-boiling-point substance 90min, be cooled to room temperature and obtain intermediate (I);
Step 2: add containing hydrogen silicone oil in intermediate (I), pass into nitrogen, stir 10 ~ 15min, be heated to 90 ~ 120 DEG C, add catalyzer, insulation reaction 4 ~ 5h, then add quaternizing agent and continue reaction 4 ~ 5h, in 90 DEG C of vacuum removal low-boiling-point substance 60min, obtained intermediate (II);
Step 3: under 40 ~ 60 DEG C of conditions, adds nonionic emulsifying agent in intermediate (II), stirs 30min, adds deionized water and regulates solid content to be 25 ~ 30%, and be 5.0 ~ 6.0 with the pH of sour regulation system, obtain Novel siliceous softening agent;
The structure of described allyl polyethenoxy ether is:
CH
2=CHCH
2r
2h is R wherein
2for-O (CH
2cH
2o)
xx=3,5,7,9,10.
Further, in step one, the mol ratio of dimeracid and N methyldiethanol amine is (1.5 ~ 2): 1;
The mol ratio of allyl polyethenoxy ether and dimeracid is 1:(1 ~ 1.5).
Further, in step one, the structure of dimeracid is: HOOC-R
1– COOH; Wherein R
1for:
Further, in step 2, the hydrogen content of containing hydrogen silicone oil is 0.3 ~ 1.5% (w/w), and the consumption of containing hydrogen silicone oil is: the Si-H in containing hydrogen silicone oil molecule and the mol ratio of allyl polyethenoxy ether are: 0.5 ~ 1.0:1.0;
The structural formula of containing hydrogen silicone oil is:
Wherein, m, n=1,2,3,4,5
Further, catalyzer described in step 2 is the aqueous isopropanol of Platinic chloride, and the consumption of catalyzer is 2.0 × 10 of containing hydrogen silicone oil quality
-3~ 3.0 × 10
-3%;
Further, quaternizing agent described in step 2 is the one in Benzyl Chloride, methyl-sulfate, ethyl chloroacetate,
The mol ratio of quaternizing agent and N methyldiethanol amine is 1:1.
Further, in step 3, nonionic emulsifying agent is the one in isomery ten polyoxyethylenated alcohol XP-80, isomerous tridecanol polyoxyethylene ether 1307,1310 and fatty alcohol-polyoxyethylene ether AEO-9;
The consumption of nonionic emulsifying agent is 5 ~ 20% of intermediate (II) quality;
The acid used by pH is regulated to be in step 3: formic acid or acetic acid.
The chemical reaction mechanism of above-mentioned preparation method is as follows:
Wherein R
3for :-CH
3,-CH
2c
6h
5,-CH
2cOOC
2h
5.
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 of above-mentioned preparation method is as follows:
Wherein,
m、n＝1,2,3,4,5
R
1for:
R
2for-O (CH
2cH
2o)
xx=3,5,7,9,10;
R
3for :-CH
3,-CH
2c
6h
5,-CH
2cOOC
2h
5.
The invention has the beneficial effects as follows:
(1) a kind of Novel siliceous softening agent outward appearance that prepared by the present invention is: white emulsion, pH is 5.0-6.0, working substance content is: 25 ~ 30%, 1:9 water miscible liquid 24h is not stratified, product has good shelf-stability, deposit in room temperature and never degenerate for 6 months, there is good dilution-resistant stability.
(2) what prepared by present method both contained plant oil based long-chain hydrocarbon containing in silicone softener molecule, and also containing polysiloxane segment and quaternary ammonium salt group, product has good dilution-resistant stability and shelf-stability.
(3) what prepared by present method is extensive containing silicone softener raw material sources, environmental protection, and the fabric feeling after wherethrough reason is plentiful, smooth, and pliability and good endurance, the loft of fabric improves a lot.
Embodiment
In order to understand the present invention better, illustrate content of the present invention further below in conjunction with embodiment, but content of the present invention is not only confined to the following examples, embodiment should not regard as limiting the scope of the present invention.
Embodiment 1:
Step one: 112.4g dimeracid and 11.9gN-methyldiethanolamine are added in the reactor with agitator, thermometer, temperature control and condensing works, pass into nitrogen, 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, continue reactions 5 hours at 120 DEG C, in 100 DEG C of vacuum removal low-boiling-point substance 90min, be cooled to room temperature and obtain intermediate (I);
Step 2: adding hydrogen content in intermediate (I) is 0.3% (w/w) containing hydrogen silicone oil 50g, passes into nitrogen, stirs 10min, is heated to 90 DEG C, adds 1.0 × 10
-3the aqueous isopropanol of g Platinic chloride, insulation reaction 4h, then adds 12.7g Benzyl Chloride and continues reaction 5h.Finally vacuum removal low-boiling-point substance 60min under 90 DEG C of conditions, obtained intermediate (II).
Step 3: under 50 DEG C of conditions, in intermediate (II), add 25g nonionic emulsifying agent 1307, stir 30min, add deionized water and regulate solid content to be 25 ~ 30%, and be 5.0 ~ 6.0 with the pH of formic acid regulation system, obtain Novel siliceous softening agent.
Product appearance is: white emulsion, and pH is 5.0-6.0, and working substance content is: 25 ~ 30%, 1:9 water miscible liquid 24h is not stratified, and product has good shelf-stability, deposits never degenerate for 6 months in room temperature, has good dilution-resistant stability.
Embodiment 2:
Step one: 112.4g dimeracid and 11.9gN-methyldiethanolamine are added in the reactor with agitator, thermometer, temperature control and condensing works, pass into nitrogen, stir, be warming up to 140 DEG C, react 3 hours, then add 99.6g allyl polyethenoxy ether (10EO), continue reaction 6 hours at 140 DEG C, in 100 DEG C of vacuum removal low-boiling-point substance 60min, be cooled to room temperature and obtain intermediate (I);
Step 2: adding hydrogen content in intermediate (I) is 0.5% (w/w) containing hydrogen silicone oil 40g, passes into nitrogen, stirs 10min, is heated to 90 DEG C, adds 1.2 × 10
-3the aqueous isopropanol of g Platinic chloride, insulation reaction 5h, then adds 12.6g methyl-sulfate and continues reaction 4h.Finally vacuum removal low-boiling-point substance 60min under 90 DEG C of conditions, obtained intermediate (II).
Step 3: under 50 DEG C of conditions, in intermediate (II), add 50g nonionic emulsifying agent AEO-9 stir 30min, adding deionized water regulates solid content to be 25 ~ 30%, and is 5.0 ~ 6.0 with the pH of formic acid regulation system, obtains Novel siliceous softening agent.
Product appearance is: white emulsion, and pH is 5.0-6.0, and working substance content is: 25 ~ 30%, 1:9 water miscible liquid 24h is not stratified, and product has good shelf-stability, deposits never degenerate for 6 months in room temperature, has good dilution-resistant stability.
Embodiment 3:
Step one: 168.6g dimeracid and 23.8gN-methyldiethanolamine are added in the reactor with agitator, thermometer, temperature control and condensing works, pass into nitrogen, stir, be warming up to 140 DEG C, react 3 hours, then add 73.2g allyl polyethenoxy ether (7EO), continue reaction 6 hours at 125 DEG C, in 100 DEG C of vacuum removal low-boiling-point substance 60min, be cooled to room temperature and obtain intermediate (I);
Step 2: adding hydrogen content in intermediate (I) is 0.4% (w/w) containing hydrogen silicone oil 50g, passes into nitrogen, stirs 10min, is heated to 90 DEG C, adds 1.0 × 10
-3the aqueous isopropanol of g Platinic chloride, insulation reaction 5h, then adds 25.2g methyl-sulfate and continues reaction 4h.Finally vacuum removal low-boiling-point substance 60min under 90 DEG C of conditions, obtained intermediate (II).
Step 3: under 50 DEG C of conditions, in intermediate (II), add 34g nonionic emulsifying agent 1310 stir 30min, adding deionized water regulates solid content to be 25 ~ 30%, and is 5.0 ~ 6.0 with the pH of formic acid regulation system, obtains Novel siliceous softening agent.
Product appearance is: white emulsion, and pH is 5.0-6.0, and working substance content is: 25 ~ 30%, 1:9 water miscible liquid 24h is not stratified, and product has good shelf-stability, deposits never degenerate for 6 months in room temperature, has good dilution-resistant stability.
Embodiment 4:
Step one: 112.4g dimeracid and 11.9gN-methyldiethanolamine are added in the reactor with agitator, thermometer, temperature control and condensing works, pass into nitrogen, stir, be warming up to 135 DEG C, react 3.5 hours, then add 99.6g allyl polyethenoxy ether (10EO), continue reaction 5 hours at 140 DEG C, in 100 DEG C of vacuum removal low-boiling-point substance 60min, be cooled to room temperature and obtain intermediate (I);
Step 2: adding hydrogen content in intermediate (I) is 1.0% (w/w) containing hydrogen silicone oil 10g, passes into nitrogen, stirs 10min, is heated to 90 DEG C, adds 3 × 10
-4the aqueous isopropanol of g Platinic chloride, insulation reaction 5h, then adds 12.2g ethyl chloroacetate and continues reaction 4h.Finally vacuum removal low-boiling-point substance 60min under 90 DEG C of conditions, obtained intermediate (II).
Step 3: under 50 DEG C of conditions, in intermediate (II), add 15g nonionic emulsifying agent XO-80 stir 30min, adding deionized water regulates solid content to be 25 ~ 30%, and is 5.0 ~ 6.0 with the pH of acetic acid regulation system, obtains Novel siliceous softening agent.
Product appearance is: white emulsion, and pH is 5.0-6.0, and working substance content is: 25 ~ 30%, 1:9 water miscible liquid 24h is not stratified, and product has good shelf-stability, deposits never degenerate for 6 months in room temperature, has good dilution-resistant stability.
Embodiment 5:
Step one: 168.6g dimeracid and 23.8gN-methyldiethanolamine are added in the reactor with agitator, thermometer, temperature control and condensing works, pass into nitrogen, stir, be warming up to 115 DEG C, react 5 hours, then add 90.8g allyl polyethenoxy ether (9EO), continue reaction 6 hours at 140 DEG C, in 100 DEG C of vacuum removal low-boiling-point substance 60min, be cooled to room temperature and obtain intermediate (I);
Step 2: adding hydrogen content in intermediate (I) is 1.0% (w/w) containing hydrogen silicone oil 15g, passes into nitrogen, stirs 10min, is heated to 90 DEG C, adds 3 × 10
-4the aqueous isopropanol of g Platinic chloride, insulation reaction 5h, then adds 25.2g Benzyl Chloride and continues reaction 4h.Finally vacuum removal low-boiling-point substance 60min under 90 DEG C of conditions, obtained intermediate (II).
Step 3: under 50 DEG C of conditions, in intermediate (II), add 60g nonionic emulsifying agent XP80 stir 30min, adding deionized water regulates solid content to be 25 ~ 30%, and is 5.0 ~ 6.0 with the pH of formic acid regulation system, obtains Novel siliceous softening agent.
Product appearance is: white emulsion, and pH is 5.0-6.0, and working substance content is: 25 ~ 30%, 1:9 water miscible liquid 24h is not stratified, and product has good shelf-stability, deposits never degenerate for 6 months in room temperature, has good dilution-resistant stability.
Embodiment 6:
A kind of application method of Novel siliceous softening agent is as follows:
The aqueous solution of 5 ~ 30g/L will be made into containing silicone softener, arrange according to following finishing technique: pure cotton fabric pads (liquor ratio 1:20, two leachings two are rolled) → preliminary drying (105 DEG C, 2min) → bake (150 DEG C, 2min) → wash → dry.
Claims (10)
1. a preparation method for Novel siliceous softening agent, is characterized in that, comprises the following steps:
Step one: first according to mol ratio (1.5 ~ 2): dimeracid and N methyldiethanol amine add in reactor by 1, pass into nitrogen, be warming up to 100 ~ 140 DEG C, reaction 2-4 hour, then allyl polyethenoxy ether is added, continue reaction 3-5 hour at 100 ~ 140 DEG C, in 100 DEG C of vacuum removal low-boiling-point substance 90min, be cooled to room temperature and obtain intermediate (I);
Step 2: add containing hydrogen silicone oil in intermediate (I), pass into nitrogen, stir 10 ~ 15min, be heated to 90 ~ 120 DEG C, add catalyzer, insulation reaction 4 ~ 5h, then add quaternizing agent and continue reaction 4 ~ 5h, in 90 DEG C of vacuum removal low-boiling-point substance 60min, obtained intermediate (II);
Step 3: under 40 ~ 60 DEG C of conditions, adds nonionic emulsifying agent in intermediate (II), stirs 30min, adds deionized water and regulates solid content to be 25 ~ 30%, and be 5.0 ~ 6.0 with the pH of sour regulation system, obtain Novel siliceous softening agent;
The structure of described allyl polyethenoxy ether is:
CH
2=CHCH
2r
2h is R wherein
2for-O (CH
2cH
2o)
xx=3,5,7,9,10.
2. the preparation method of a kind of Novel siliceous softening agent according to claim 1, is characterized in that,
In step one, the mol ratio of dimeracid and N methyldiethanol amine is (1.5 ~ 2): 1;
The mol ratio of allyl polyethenoxy ether and dimeracid is 1:(1 ~ 1.5).
3. the preparation method of a kind of Novel siliceous softening agent according to claim 1, is characterized in that,
In step one, the structure of dimeracid is: HOOC-R
1– COOH; Wherein R
1for:
4. the preparation method of a kind of Novel siliceous softening agent according to claim 1, is characterized in that,
In step 2, the hydrogen content of containing hydrogen silicone oil is 0.3 ~ 1.5% (w/w), and the consumption of containing hydrogen silicone oil is: the Si-H in containing hydrogen silicone oil molecule and the mol ratio of allyl polyethenoxy ether are: 0.5 ~ 1.0:1.0;
The structural formula of containing hydrogen silicone oil is:
Wherein, m, n=1,2,3,4,5.
5. the preparation method of a kind of Novel siliceous softening agent according to claim 1, is characterized in that,
Catalyzer described in step 2 is the aqueous isopropanol of Platinic chloride, and the consumption of catalyzer is 2.0 × 10 of containing hydrogen silicone oil quality
-3~ 3.0 × 10
-3%.
6. the preparation method of a kind of Novel siliceous softening agent according to claim 1, is characterized in that,
Quaternizing agent described in step 2 is the one in Benzyl Chloride, methyl-sulfate, ethyl chloroacetate.
7. the preparation method of a kind of Novel siliceous softening agent according to claim 1, is characterized in that,
The mol ratio of quaternizing agent and N methyldiethanol amine is 1:1.
8. the preparation method of a kind of Novel siliceous softening agent according to claim 1, is characterized in that,
In step 3, nonionic emulsifying agent is the one in isomery ten polyoxyethylenated alcohol XP-80, isomerous tridecanol polyoxyethylene ether 1307,1310 and fatty alcohol-polyoxyethylene ether AEO-9;
The consumption of nonionic emulsifying agent is 5 ~ 20% of intermediate (II) quality;
The acid used by pH is regulated to be in step 3: formic acid or acetic acid.
9. the Novel siliceous softening agent prepared according to the arbitrary described preparation method of claim 1-8.
10. Novel siliceous softening agent according to claim 9, is characterized in that, its main component structure is as follows:
Wherein,
m、n＝1,2,3,4,5
R
1for:
R
2for-O (CH
2cH
2o)
xx=3,5,7,9,10;
R
3for :-CH
3,-CH
2c
6h
5,-CH
2cOOC
2h
5.
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| 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 |
| CN110983787A (en) * | 2019-12-17 | 2020-04-10 | 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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