CN101367942A - Preparation method for branched chain type amino-long chain alkyl co-modified silicone oil and its microemulsion, and uses thereof - Google Patents
Preparation method for branched chain type amino-long chain alkyl co-modified silicone oil and its microemulsion, and uses thereof Download PDFInfo
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Abstract
The invention discloses a method for preparing branched-chain amino long-chain alkyl co-modified silicone oil, and microemulsion liquid thereof as well as an application thereof. The constitutional formula of the silicone oil is shown on the right. Hindered amino-silane, secondary amidocyanogen silane and alkyl silane (which are not easy to change color and denaturize under high temperature) as well as linear body are chosen in the method for reaction through polymerization balance, and the desired amino-modified silicone oil is synthesized. When the microemulsion softening agent emulsified by the product is used to neaten textile fabrics, high softness and smooth texture can be achieved. In addition, the product has sound stability to shearing force, centrifugal force as well as electrolyte, hard water, and the like, and the product does not has any adverse effect on the color light of textile fabrics, and yellow stain can be avoided. The product is applicable to white and light-colored textile fabrics neatening, particularly applicable to easy-care neatening of mercerized wool textile fabrics and white and light-colored textile fabrics, the processed textile fabrics have the advantages of soft, smooth and plumpy texture, and the original color tone and style can be maintained.
Description
Technical field
The present invention relates to a kind of organosilicon macromolecule polymkeric substance, particularly a kind of branched chain type amino-long chain alkyl co-modified silicone oil and application thereof.
Background technology
Amino-modified silicone oil is owing to its excellence, outstanding softness, smooth feel are widely used in aspects such as textile printing and dyeing, leather, papermaking, daily necessities nursing.But white and light fabric yellowing after causing putting in order owing to contained amino, particularly primary amino are easily oxidized influence the finishing effect of fabric and the aesthetic property of dress ornament.There are many methods to carry out modification to reach inhibition or to reduce xanthochromic purpose to amino.As being total to modification (spy opens flat 6-184946.1994, the spy opens flat 4-119174.1992) with epoxy group(ing) modification, epoxy group(ing) and propylene vinegar; With the modification of polyoxy alkylidene glycidyl ether (spy opens flat 9-21071.1997); With polyethers isocyanic ester and epoxide modified (spy opens flat 4-11081.1992); Polyether carboxylic acid's modification with amide-containing; With acylating agent (as acetic anhydride) modification; Use C
10-C
20Higher fatty acid modification or the like.Though these method of modifying can both suppress xanthochromia or xanthochromia not to a certain extent, Jiao Huan cost is to have reduced the original softness of amido silicon oil, level and smooth style inevitably therewith.Simultaneously, owing to be subjected to the active hydrogen reaction degree of depth in modifying agent and the aminosilane and the influence of modifying agent level of activity, modification usually is very uneven and unmanageable.To such an extent as to the product stability after the modification is poor, feel is average.And, can use toluene, organic alcohols material in most method of modifying, caused the negative impact of certain degree to production operation personnel's healthy and atmospheric environment.
In sum: because the various shortcoming that aforesaid method exists, therefore, be necessary that, environmental protection low with a kind of cost, maneuverable method substitute traditional production method.
Summary of the invention
First technical problem to be solved by this invention provides a kind of novel not xanthochromia branched chain type amino-long chain alkyl co-modified silicone oil.
Second technical problem to be solved by this invention provides the preparation method of above-mentioned silicone oil.
The 3rd technical problem to be solved of the present invention provides a kind of microemulsion preparation method who contains above-mentioned silicone oil.
The 4th technical problem to be solved by this invention is to contain the application of the microemulsion of above-mentioned silicone oil at aspects such as mercerized wool, textile printing and dyeing, papermaking.
The technical scheme of technical solution problem of the present invention is: a kind of branched chain type amino-long chain alkyl co-modified silicone oil, and its structural formula is as follows:
R
1General structure be: R-Si (Me)-(R ')
2
Wherein:
R′＝OCH
3、OC
2H
5
R
2Structural formula be: CH
3Si (OCH
3)
3, CH
3Si (OC
2H
5)
3, C
nH
2n+1Si (OCH
3)
3, CnH
2n+1Si (OC
2H
5)
3, C
nH
2n+1(Me) Si (OCH
3)
2, C
nH
2n+1Si (Me) (OC
2H
5)
2
Preferred X=500～2500; Y=1～50; M=1～20; N=5～60.
Preferred R
1Structural formula be: (C
3H
6NC
4H
8NH) Si (Me) (OCH
3)
2, (C
3H
6NHC
6H
11) Si (Me) (OCH
3)
2
Preferred R
2Structural formula be C
8H
17Si (OCH
3)
3, C
8H
17Si (OC
2H
5)
3
The viscosity of described not xanthochromia branched chain type amino-long chain alkyl co-modified silicone oil (25 ℃) is 100～5000mPS, non-volatile content 〉=98.6% (105 ℃/3h).
The preparation method of described modified silicon oil is:
Linear body, hexamethyldisiloxane and amino silicane coupling agent are mixed, be warmed up to 80 ℃-120 ℃, behind the stirring reaction 30-90min, add catalyzer and reaction promotor, insulation reaction 1h～10h vacuumized 0.5-5.0 hour; Add the long chain alkyl silane coupling agent then, insulation reaction 1h～10h cools to 50 ℃-60 ℃ then, adds deionized water, and insulation reaction 0.5h～3h vacuumized 0.5-1.5 hour then; Being warmed up to 150 ℃-210 ℃ once more, control pressure is≤-0.04MPa, insulation 1h～5h, cooling gets final product.Linear body, hexamethyldisiloxane, amino silicane coupling agent, catalyzer, reaction promotor, long chain alkyl silane coupling agent, deionized water, its weight ratio is: 75-95:0.1-1.0:5-25:0.01-0.02:0.002-0.008:2.5-10:0.5-2.0.
Said linear body is hydroxy-end capped linear silicone oils, its purity requirement: 〉=99.5%.
Described amino silicane coupling agent is: 3-piperazinyl propyl group methyl dimethoxysilane, N one cyclohexyl
One Y, one aminopropyl methyl dimethoxysilane.
Described catalyzer is sodium hydroxide, potassium hydroxide, hydrated barta, one or more mixtures of Tetramethylammonium hydroxide.
Described reaction promotor is: cyclohexyl-18-crown-6 (cyclic polyether).
R in the described long silane coupling agent
1Structure silane accounts for the 35%-75% of coupling agent gross weight; R
2Structure silane accounts for the 25%-65% of coupling agent gross weight.
The preparation of microemulsion method that contains above-mentioned modified silicon oil:
With emulsifying agent with account for gross weight 20-30% deionized water and mix, stirred 15～45 minutes, add above-mentioned modified silicon oil again, stirred 20～60 minutes, add acid, the pH value of regulating emulsion is 5-8, be stirred to emulsion to water white transparency, adding accounts for gross weight 70-80% deionized water, stirs, get final product, the weight ratio of modified silicon oil, emulsifying agent, deionized water is 1:0.1-0.6:1.5-8.0.
Described emulsifying agent is: straight or branched fatty alcohol polyethenoxy ether class, polyoxyethylene nonylphenol ether class; The HLB value of emulsifying agent is between 10.0-15.0.The emulsifying agent consumption is silicon oil dosage 10%-60%.Can be emulsified into the microemulsion of 1.0%-80%.
Said acid is: hydrochloric acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, thionamic acid is a kind of or several mixture; Described sour consumption is the 0.1%-5.0% of emulsion total amount.
The main quality index of prepared microemulsion: outward appearance: colourless transparent liquid; Solid content: (1.0-80.0) %; Ionic: nonionic/weak cation type; PH value: 5.0-8.0; Stability: 30min is not stratified in the 3000r/min centrifugation, not floating oil.
The prepared microemulsion of the present invention is in the application of wool mercerising flexible smooth finishing composition, textile printing and dyeing flexible smooth finishing composition, the soft surface slip agent of paper.
Have excellent softness, smooth feel, good plentiful effect with the material after the above-mentioned microemulsion processing.
The present invention has selected low molar mass, and the very narrow end hydroxyl silicone oil (linear body) of molecular weight distribution is the main chain of macromolecular chain.It has shortened the molecular balance process, and provide product component very high unicity, be that subsequent product keeps stable prerequisite in use, the resistance type silane that is subjected to stable, not oxidation stain at high temperature and sex change is main coupling agent, it is to guarantee that branched chain type amino-long chain digs the not xanthochromic core of alkyl co-modified silicone oil, and provides amido silicon oil main softness; By having selected special trifunctional, the auxiliary coupling agent of two functional silanes, make amido silicon oil have special smooth hand and elasticity; Utilize technology controlling and process guaranteed amino on whole macromolecular chain uniform distribution and the polymerization degree of branched structure.
The present invention compared with prior art, selected at high temperature not that be subjected to resistance type aminosilane, secondary amine silane and linear body and the long chain alkyl silane of easy oxidation discoloration and sex change react through polymerization equilibrium, synthesized a kind of brand-new branched chain type amino-long chain alkyl co-modified silicone oil.When being used for textile finishing, have extraordinary softness, smooth feel by its emulsive microemulsion type softening agent.And product is fairly good to shearing force, centrifugal force and ionogen, hard water equistability, at high temperature fabric coloured light is had no adverse effects and does not have the xanthochromia phenomenon.Be suitable for the arrangement of white and light fabric, be particularly suitable for the noniron finish of the arrangement of mercerized wool flexible smooth and white and light fabric.Soft, sliding, the plentiful characteristics of mixing that fabric after the arrangement has.And can keep the original tone style of fabric.
Embodiment
Below in conjunction with embodiment the present invention is done detailed explanation.
Linear body of the present invention is produced by German Wa Ke company.
Cyclohexyl-18-crown-6 is produced by Zhejiang Province's fairy house county medication chemistry demonstration plant company.
Embodiment 1:
With the 515g linear body, 3.0g hexamethyldisiloxane and 62.6g 3-piperazinyl propyl group methyl dimethoxysilane add in the 1000ml there-necked flask, stirring is warming up to 100 ℃-110 ℃, stirring reaction 30min, add 120mg Tetramethylammonium hydroxide and 6mg cyclohexyl-18-crown-6 (cyclic polyether), insulation reaction 2h, under the condition of vacuum tightness, react 3h then for-0.1MPa, to take off lower-molecular substance, add n-octyl Trimethoxy silane 31.0g again, stirring reaction 2h cools to 55 ℃ then, the deionized water that adds 6.0g, stirring reaction 30min, in vacuum tightness be then-condition of 0.1MPa under, reaction 1.5h, to take off lower-molecular substance, be warmed up to 165 ℃-185 ℃ again, in vacuum tightness be-0.MPa reacts 1h, to destroy catalyzer, cooling back blowing, obtain the water white transparency thick liquid, viscosity (25 ℃) is 350mPaS, non-volatile content 98.7% (105 ℃/3h).Yield 99.2%.
Its average structure formula is:
In the formula: R
1=C
3H
6NC
4H
8NHSi (Me) (OCH
3)
2
R
2＝C
8H
17Si(OCH
3)
3
X＝500，Y＝25，M＝8，N＝36
Embodiment 2:
552.5g linear body, 3.0g hexamethyldisiloxane and 41.7g 3-piperazinyl propyl group methyl dimethoxysilane are added in the 1000ml there-necked flask, stirring is warming up to 100 ℃-110 ℃, stirring reaction 30min, add 60mg potassium hydroxide and 6mg cyclohexyl-18-crown-6 (cyclic polyether), insulation reaction 2h reacts 3h then under vacuum tightness is the condition of 0MPa.Add dodecyl Trimethoxy silane 15.0g again, stirring reaction 2h cools to 55 ℃ then, add the deionized water of 2.0g, stirring reaction 30min is under the condition of 0MPa in vacuum tightness then, reaction 1.5h adds 1.0g Glacial acetic acid catalyst neutralisation, neutralization reaction 30min again.Being warmed up to 165 ℃ ~ 185 ℃ once more, is to react 1h under the condition of 0MPa in vacuum tightness, and cooling back blowing obtains little yellow transparent thick liquid, and viscosity (25 ℃) is 500mPaS, non-volatile content 98.6% (105 ℃/3h).Yield 98.8%.
Its average structure formula is:
In the formula: R
1=C
3H
6NC
4H
8NHSi (Me) (OCH
3)
2
R
2＝C
12H
25Si(OCH
3)
3
X＝860，Y＝15，M＝5，N＝20
Embodiment 3:
509.8g linear body, 3.0g hexamethyldisiloxane and 88.2g N one cyclohexyl one Y one aminopropyl methyl dimethoxysilane are added in the 1000ml there-necked flask, stirring is warming up to 100 ℃-110 ℃, stirring reaction 30min, add 180mg potassium hydroxide and 30mg cyclohexyl-18-crown-6 (cyclic polyether), insulation reaction 2h reacts 3h then under the condition of vacuum tightness for-0.08MPa.Add n-octyl triethoxyl silane 30.0g again, stirring reaction 2h cools to 55 ℃ then, the deionized water that adds 6.0g, stirring reaction 30min, in vacuum tightness be then-condition of 0.08MPa under, reaction 1.5h adds 3.5g Glacial acetic acid catalyst neutralisation, neutralization reaction 30min again.Be warmed up to 165 ℃ ~ 185 ℃ once more, react 1h under the condition of vacuum tightness for-0.08MPa, cooling back blowing obtains little yellow transparent thick liquid, and viscosity (25 ℃) is 300mPaS, non-volatile content 98.9% (105 ℃/3h).Yield 99.4%.
Its average structure formula is:
In the formula: R
1=C
3H
6NHC
6H
11Si (Me) (OCH
3)
2
R
2＝C
8H
17Si(OC
2H
5)
3
X＝480，Y＝22，M＝8，N＝28
Embodiment 4:
525.0g linear body, 1.5g hexamethyldisiloxane and 88.2g N one cyclohexyl one Y one aminopropyl methyl dimethoxysilane are added in the 1000ml there-necked flask, stirring is warming up to 100 ℃-110 ℃, stirring reaction 30min, add 60mg potassium hydroxide and 30mg cyclohexyl-18-crown-6 (cyclic polyether), insulation reaction 2h reacts 3h then under the condition of vacuum tightness for-0.1MPa.Add methyltrimethoxy silane 15.0g again, stirring reaction 2h cools to 55 ℃ then, the deionized water that adds 2.0g, stirring reaction 30min, in vacuum tightness be then-condition of 0.1MPa under, reaction 1.5h adds 1.0g Glacial acetic acid catalyst neutralisation, neutralization reaction 30min again.Be warmed up to 165 ℃ ~ 185 ℃ once more, react 1h under the condition of vacuum tightness for-0.1MPa, cooling back blowing obtains little yellow transparent thick liquid, and viscosity (25 ℃) is 1200mPaS, non-volatile content 99.4% (105 ℃/3h).Yield 98.7%.
Its average structure formula is:
In the formula: R
1=C
3H
6NHC
6H
11Si (Me) (OCH
3)
2
R
2＝CH
3Si(OCH
3)
3
X＝1860，Y＝10，M＝5，N＝18
Embodiment 5
30% preparation of microemulsion:
With 7.8g fatty alcohol-polyoxyethylene ether, 3.9g polyoxyethylene nonylphenol ether, add the 0.6g ethylene glycol monobutyl ether again and mix and be mixed with emulsifying agent, add 250ml and fill in 14g (40-50) ℃ the reaction flask of deionized water, stir 30min; Add the prepared modified silicon oil of 20g the foregoing description 1 again, stir emulsification 45min down; Then, add 60% the acetic acid solution of 2.0g, be stirred to water white transparency (needing 35min) after, add 59.6g water, stir and can filter blowing, obtain microemulsion A.
The technical indicator of latex A is as follows:
Outward appearance: colourless transparent liquid
Solid content: 29.94%
Ionic: nonionic/weak cation
PH value: 6.0
Stability: 30min is not stratified in the 3000r/min centrifugation, not floating oil
Embodiment 6
50% preparation of microemulsion:
8.0g isomery lauryl alcohol Soxylat A 25-7,4.0g polyoxyethylene nonylphenol ether are mixed and be mixed with emulsifying agent, add 250ml and fill in 7.5g (40-50) ℃ the reaction flask of deionized water, stir 30min; Add the prepared modified silicon oil of 24g the foregoing description 3 again, stir emulsification 45min down; Then, add 60% the acetic acid solution of 2.0g, be stirred to water white transparency (needing 60min) after, add 28.5g gram water, stir and can filter blowing microemulsion B.
The technical indicator of emulsion B is as follows:
Outward appearance: colourless transparent liquid
Solid content: 50.02%
Ionic: nonionic/weak cation
PH value: 6.5
Stability: 30min is not stratified in the 3000r/min centrifugation, not floating oil
Performance Detection: embodiment 5,6 prepared microemulsions are used for the textile bleached cotton fabric of woven twill, use Q simultaneously
2-8797 (Dow Corning Corporation's productions), 21645 (Rhodia's productions), do not use the blank of modified silicon oil to compare.
Concrete technology is:
Microemulsion consumption: 30g/L
Pad: one soaks one rolls:
Bathe temperature: 45 ℃;
Pick-up: 75%-80%;
Drying time/temperature: 5min/85 ℃;
High temperature bakes time/temperature: 10min/180 ℃;
Naturally moisture regain is 24 hours.
The detection method of described flexibility, smooth property, yellowing resistance is the feel digital palpation for examination of trauma, is engaged in the experienced master worker of hand feel finishing for a long time by 8 and touches evaluation,
The grade of flexibility: very poorly be 1, difference is 2, be preferably 3, be 4 well, fine be 5.
The grade of smooth property: very poorly be 1, difference is 2, be preferably 3, be 4 well, fine be 5.
The grade of yellowing resistance: very poorly be 1, difference is 2, be preferably 3, be 4 well, fine be 5.
Specific targets are as shown in table 1:
Table 1. performance comparison sheet
| Flexibility | Smooth property | Yellowing resistance | Over-all properties | |
| Embodiment 5 | 4.8 | 4.5 | 5.0 | 4.5 |
| Embodiment 6 | 4.5 | 5.0 | 5.0 | 4.5 |
| Q 2—8797 | 4.0 | 5.0 | 4.0 | 4.0 |
| Sieve ground inferior 21645 | 4.5 | 3.8 | 5.0 | 4.4 |
| Blank assay | 2.0 | 2.0 | 5.0 | 3.0 |
As can be seen from Table 1: the not xanthochromia softening agent of the present invention's preparation all has excellent properties on every index; Inferior 21645 flexibilities in sieve ground and smooth property all have preferable performance, and both all have excellent anti-xanthochromia effect.Q
2-8797 (DOW CORNINGs) have superior performance on smooth property, but all undesirable on its softness and the anti-xanthochromia.From comparative result: branched chain type amino-long chain alkyl co-modified silicone oil that the present invention is prepared and microemulsion prepared therefrom all have excellent performance at aspects such as soft, smooth property and yellowing resistances.Can substitute external product fully, effectively reduce cost.Be specially adapted to mercerized wool kind fabric and white and the arrangement of light fabric feeling, style is good, added value is high.
Claims (10)
1. branched chain type amino-long chain alkyl co-modified silicone oil, it is characterized in that: its structural formula is as follows:
Wherein: x, y, m, n are positive integer, and x〉n 〉=m; X=0～5000; Y=0～100; M=0～50; N=0～150;
R
1General structure be: R-Si (Me)-(R ')
2
Wherein:
R′＝OCH
3、OC
2H
6
R
2Structural formula be: CH
3Si (OCH
3)
3, CH
3Si (OC
2H
5)
3, C
nH
2n+1Si (OCH
3)
3, C
nH
2n+1Si (OC
2H
5)
3, C
nH
2n+1(Me) Si (OCH
3)
2, C
nH
2n+1Si (Me) (OC
2H
5)
2
2. a kind of branched chain type amino-long chain alkyl co-modified silicone oil according to claim 1 is characterized in that: described X=500～2500; Y=1～50; M=1～20; N=5～60.
3. a kind of branched chain type amino-long chain alkyl co-modified silicone oil according to claim 1 is characterized in that: described R
1Structural formula be: (C
3H
6NC
4H
8NH) Si (Me) (OCH
3)
2, (C
3H
6NHC
6H
11) Si (Me) (OCH
3)
2R
2Structural formula be C
8H
17Si (OCH
3)
3, C
8H
17Si (OC
2H
5)
3
4. the preparation method of the described branched chain type amino-long chain alkyl co-modified silicone oil of claim 1, it is characterized in that: linear body, hexamethyldisiloxane and amino silicane coupling agent are mixed, be warmed up to 80 ℃-120 ℃, behind the stirring reaction 30-90min, add catalyzer and reaction promotor, insulation reaction 1h～10h vacuumized 0.5-5.0 hour; Add the long chain alkyl silane coupling agent then, insulation reaction 1h～10h cools to 50 ℃-60 ℃ then, adds deionized water, and insulation reaction 0.5h～3h vacuumized 0.5-1.5 hour then; Being warmed up to 150 ℃-210 ℃ once more, control pressure is≤-0.04MPa, insulation 1h～5h, cooling gets final product; The weight ratio of linear body, hexamethyldisiloxane, amino silicane coupling agent, catalyzer, reaction promotor, long chain alkyl silane coupling agent, deionized water is: 75-95:0.1-1.0:5-25:0.01-0.02:0.002-0.008:2.5-10:0.5-2.0.
5. the preparation method of a kind of branched chain type amino-long chain alkyl co-modified silicone oil according to claim 4, it is characterized in that: described amino silicane coupling agent is: 3-piperazinyl propyl group methyl dimethoxysilane, N one cyclohexyl one Y one aminopropyl methyl dimethoxysilane.
6. the preparation method of a kind of branched chain type amino-long chain alkyl co-modified silicone oil according to claim 4, it is characterized in that: described catalyzer is sodium hydroxide, potassium hydroxide, hydrated barta, one or more mixtures of Tetramethylammonium hydroxide; Described reaction promotor is: cyclohexyl-18-crown-6 (cyclic polyether).
7. the preparation method of a kind of branched chain type amino-long chain alkyl co-modified silicone oil according to claim 4 is characterized in that: R in the described long silane coupling agent
1Structure silane accounts for the 35%-75% of coupling agent gross weight; R
2Structure silane accounts for the 25%-65% of coupling agent gross weight.
8. the described branched chain type amino-long chain alkyl co-modified silicone oil preparation of microemulsion of claim 1 method is characterized in that:
With emulsifying agent with account for gross weight 20-30% deionized water and mix, stirred 15～45 minutes, add above-mentioned modified silicon oil again, stirred 20～60 minutes, add acid, the pH value of regulating emulsion is 5-8, be stirred to emulsion to water white transparency, adding accounts for gross weight 70-80% deionized water, stirs, get final product, the weight ratio of modified silicon oil, emulsifying agent, deionized water is 1:0.1-0.6:1.5-8.0.
9. a kind of branched chain type amino-long chain alkyl co-modified silicone oil preparation of microemulsion method according to claim 8 is characterized in that:
Described emulsifying agent is: straight or branched fatty alcohol polyethenoxy ether class, polyoxyethylene nonylphenol ether class; Described acid is: hydrochloric acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, thionamic acid is a kind of or several mixture; Described sour consumption is the 0.1%-5.0% of emulsion total amount.
10. claim 8 or 9 prepared microemulsions are in the application of wool mercerising flexible smooth finishing composition, textile printing and dyeing flexible smooth finishing composition, the soft surface slip agent of paper.
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| GB9115592D0 (en) * | 1991-07-18 | 1991-09-04 | Dow Corning | Organosilicon crosslinking compounds having multiple functionality |
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| EP1258503A1 (en) * | 2001-05-15 | 2002-11-20 | Clariant International Ltd. | Modified polyorganosiloxanes, aqueous emulsions, preparation and use thereof |
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| JP5057022B2 (en) * | 2006-10-13 | 2012-10-24 | 信越化学工業株式会社 | Emulsion composition for coating |
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