CN102115538B - Modified amino silicone oil and application thereof - Google Patents
Modified amino silicone oil and application thereof Download PDFInfo
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- CN102115538B CN102115538B CN201010597301A CN201010597301A CN102115538B CN 102115538 B CN102115538 B CN 102115538B CN 201010597301 A CN201010597301 A CN 201010597301A CN 201010597301 A CN201010597301 A CN 201010597301A CN 102115538 B CN102115538 B CN 102115538B
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Abstract
The invention relates to modified amino silicone oil which is jointly modified by a fatty-group long chain and cations. The modified amino silicone oil is prepared by reacting amino silicone oil with a quaternary ammonium type modifier (a compound in a formula I) at the temperature of between 0 and 150DEG C for 1 to 15 hours under the alkaline condition. The modified amino silicone oil can be used for preparing a textile finishing agent. Textiles finished by the textile finishing agent comprising the modified amino silicone oil have good handfeel; meanwhile, the smoothness of the textiles is improved, the hydrophilcity of the textiles is greatly improved, and the yellowing degree of the treated textiles is reduced; moreover, the textile finishing agent hardly falls off in the washing process.
Description
Technical field
The present invention relates to a kind of modified amino silicon oil and uses thereof.Specifically, relate to fatty clan elder's carbochain of a kind of warp and positively charged ion and be total to amido silicon oil of modification and uses thereof.
Background technology
Organosilicon has another name called ZGK 5, is to be main chain with the siloxanes, has hydroxyl on the Siliciumatom, a base polymer of alkyl and other organic groups.Because organosilicon has good low surface tension, wettability, defoaming and foam stability; Toxicity property all is characteristics such as physiology inertia basically; And be applied to fabric post-treatment; Can give fabric sofetening, excellent properties such as smooth, antistatic, hydrophobic, heat-resisting, so organosilicon is one type of important auxiliary agent in the textile garment processing industry.
Amido silicon oil is most widely used a kind of fabric of organosilicon finishing composition, can give fabric good flexible nature.But there are problems such as the fabric after easy xanthochromia under the high temperature and the arrangement is hydrophobic in amido silicon oil, and therefore there is certain defective in the arrangement to particular web.At present the modification of amido silicon oil is mainly contained cation-modified, polyether-modified, the amidation modification, though the product after the modification has obtained certain inhibition to the easy yellowing problem of amido silicon oil, all there is certain defective in alkylation modifications etc.Some makes the flexibility of amido silicon oil that reduction significantly arranged, like polyether-modified, cation-modified, amidation modification; Also some reduces the wetting ability of silicone oil greatly, like alkylation modification.
Therefore, provide a kind of new modified amido silicon oil of high comprehensive performance just to become the technical issues that need to address of the present invention.
Summary of the invention
One of the object of the invention is, a kind of novel modified amino silicon oil is provided;
Two of the object of the invention is, a kind of purposes of above-mentioned modified amino silicon oil is provided.
Modified amino silicon oil provided by the present invention, it is made by the following preparation method of key step:
Under the condition that has mineral alkali to exist, reacted 1 hour～15 hours in 0 ℃～150 ℃ by amido silicon oil and properties-correcting agent (formula I compound), obtain target compound (modified amino silicon oil provided by the present invention);
Wherein, R
1, R
2And R
3Independently be selected from respectively: C
1～C
20A kind of in chain (straight or branched) alkyl, and R
1, R
2And R
3In have one at least for C
8～C
20Chain (straight or branched) alkyl; X is halogen (F, Cl, Br or I);
The mol ratio of amido silicon oil and formula I compound is 1.0: 0.1～1.0: 10.0.
In optimized technical scheme of the present invention, weight-average molecular weight 500～100,000 is used in suggestion, and (or viscosity (25 ℃) is 200cP～100,000cP), the amine value is: the amido silicon oil of 0.05mmol/g～3.00mmol/g.
In another optimized technical scheme of the present invention, R
1, R
2And R
3In one (arbitrarily) arranged for C
10～C
20Chain (straight or branched) alkyl is selected from and remain two: C
1～C
6A kind of in chain (straight or branched) alkyl;
Preferred technical scheme is: R
1, R
2And R
3In one (arbitrarily) arranged for G
12～C
18Chain (straight or branched) alkyl is selected from and remain two: C
1～C
3A kind of in chain (straight or branched) alkyl;
Best technical scheme is: R
1, R
2And R
3In one (arbitrarily) arranged for C
12～C
18Chain (straight or branched) alkyl is methyl and remain two.
In another optimized technical scheme of the present invention, the temperature of reaction of amido silicon oil and properties-correcting agent (formula I compound) is 50 ℃～100 ℃, and the reaction times is 3 hours～10 hours.
In another optimized technical scheme of the present invention, the mineral alkali of recommending to use is: volatile caustic, Pottasium Hydroxide, sodium hydroxide or calcium hydroxide, the mol ratio of amido silicon oil and mineral alkali is advisable to be controlled at 1.0: 0.1～1.0: 10.0.
Modified amino silicon oil provided by the present invention can be used for the preparation of fabric finishing agent.
Embodiment
A kind of method for preparing modified amino silicon oil of the present invention comprises the steps:
(i) preparation of properties-correcting agent:
(X is halogen (F, Cl, Br or I) with HX acid; Example hydrochloric acid etc.) and solvent place reactor drum; Under-20 ℃～0 ℃ condition; In this reactor drum, add aliphatic tertiary amine (compound shown in the formula II), keep 1 hour～10 hours (preferred 3 hours～5 hours) at-20 ℃～0 ℃ state, regulating its pH value is 4～10 (preferred pH value is 5～9); Under-20 ℃～0 ℃ condition; In described reactor drum, add halogenated epoxy propane (compound shown in the formula III) again; In 1 hour～10 hours (preferred 1 hour～2 hours) of-20 ℃～0 ℃ state insulation; Be warming up to 1 hour～10 hours (preferred 3 hours～7 hours) of 10 ℃～100 ℃ (preferred 50 ℃～70 ℃) reaction, cooling is except that getting properties-correcting agent (formula I compound) after desolvating;
Wherein: said solvent is deionized water, anhydrous methanol, absolute ethyl alcohol, Virahol, toluene, THF or N, dinethylformamide; R
1, R
2, R
3Said identical with the definition of X with preamble.
The (ii) preparation of modified amino silicon oil:
Place another to have the reactor drum of temperature regulating device amido silicon oil (commercially available article), properties-correcting agent (formula I compound), mineral alkali and organic solvent; Keep 1 hour～15 hours (preferred 3 hours～8 hours) at 0 ℃～150 ℃ (50 ℃～90 ℃) states; Filter gained reaction product (filtering precipitate thing); Steam and remove organic solvent in the gained filtrating, obtain title product (modified amino silicon oil of the present invention);
Wherein, The mol ratio of amido silicon oil, formula I compound and mineral alkali is 1.0: (0.1～1.0): (0.1～1.0); Said organic solvent is: anhydrous methanol, absolute ethyl alcohol, Virahol, toluene, THF or N; Dinethylformamide, its consumption are the 20wt%～80wt% of reactant (amido silicon oil, formula I compound, mineral alkali and organic solvent) gross weight.
The (iii) preparation of modified amino silicon oil emulsion:
Modified amino silicon oil that will (ii) be prepared by step and emulsifying agent and water mix, and can obtain the modified amino silicon oil emulsion;
Wherein: said emulsifying agent is selected from: alkyl sulfuric ester salt, sulfonated alkylbenzene, AEO, TX10, fatty acid loss water sorbit ester Soxylat A 25-7, stearic acid polyoxyethylene ether, empgen BB, C
12-C
14A kind of or (contain two kinds) more than two kinds in alkyl dimethyl tertiary amine oxide, carboxylic acid type amphoteric imidazoline or the amino acid type surfactant;
The quality ratio of emulsifying agent and modified amino silicon oil is 0.015～0.8 (preferred 0.1～0.3).
Modified amino silicon oil provided by the invention can be used for the preparation of fabric finishing agent.Through the fabric of the fabric finishing agent arrangement that comprises modified amino silicon oil provided by the invention, existing good feel has increased the smooth property of fabric simultaneously, has greatly improved the wetting ability of fabric, has reduced the xanthochromia degree of handling the back fabric, and difficult drop-off during washing.
Through embodiment the present invention is done further elaboration below, the example of being lifted does not limit protection scope of the present invention.
Embodiment 1
(1) in there-necked flask, adds 10ml concentrated hydrochloric acid and 50ml ethanol, under-10 ℃～0 ℃ condition, in this there-necked flask, drip 21.3g dodecyl dimethyl amine; Insulation (10 ℃～0 ℃) 4 hours, regulating the pH value is 6～7, under-20 ℃～0 ℃ condition; In this there-necked flask, drip epoxy chloropropane again, insulation (20 ℃～0 ℃) 1 hour is warming up to 30 ℃; Reacted 5 hours, cooling, removing desolvates promptly obtains properties-correcting agent 3-chloro-2-hydroxypropyl dodecyl dimethyl ammonium chloride.
IR：3300(s，υO-H)，2918(s，υC-H)，2851(s，υC-H)，1469(m，δC-H)，950(w，υC-N)，721(w，δC-H)；
1H-NMR(CDCl
3)(ppm)δ0.96(-CCH3)δ1.29-1.33(-CCH2)δ2.0(-OH)δ2.0(OH)δ1.73(-NCCH2C)δ3.24-3.30(-NCH3)δ3.274-3.52(-NCH2(CO-)CCl)δ3.65-3.402.5l(-NCC(O-)CH2Cl)δ4.63(-NCCH(O-)CCl)。
(2) in another there-necked flask, add the 30g amido silicon oil (amine value: 0.60mmol/g, viscosity (25 ℃): 4,000cP); 3.69g 3-chloro-2-hydroxypropyl dodecyl dimethyl ammonium chloride; 0.43g sodium hydroxide and 50ml ethanol, reaction is 5 hours under 50 ℃ of conditions, cooling; Remove by filter throw out, underpressure distillation removes to desolvate and obtains title product (modified amino silicon oil).
(3) with the 6g emulsifying agent (by AEO (AEO-4): AEO (AEO-9)=1: 1 (mass ratio) composite making), 20g is mixed by modified amino silicon oil and the 74g deionized water that step (2) makes, emulsion, the brief note latex A.
Wherein: AEO-4, AEO-9 provide by Shenzhen Tianding Fine Chemical Engineering Manufacturing Co., Ltd.
Embodiment 2
(1) in there-necked flask, adds 10ml concentrated hydrochloric acid and 50ml methyl alcohol, under-10 ℃～0 ℃ condition, in this there-necked flask, drip 28.9g tetradecyl dimethyl amine; Insulation (10 ℃～0 ℃) 5 hours, regulating the pH value is 5～6, under-20 ℃～0 ℃ condition; In this there-necked flask, drip epoxy chloropropane again; Insulation (20 ℃～0 ℃) 1 hour is warming up to 50 ℃, reacts 7 hours; Cooling, removing desolvates promptly obtains fatty clan elder's carbochain properties-correcting agent 3-chloro-2-hydroxypropyl tetradecyl alkyl dimethyl ammonium chloride.
IR：3300(s，υO-H)，2918(s，υC-H)，2851(s，υC-H)，1469(m，δC-H)，950(w，υC-N)，721(w，δC-H)
1H-NMR(CDCl
3)(ppm)δ0.96(-CCH3)δ1.29-1.33(-CCH2)δ2.0(-OH)δ2.0(OH)δ1.73(-NCCH2C)δ3.24-3.30(-NCH3)δ3.274-3.52(-NCH2(CO-)CCl)δ3.65-3.402.51(-NCC(O-)CH2Cl)δ4.63(-NCCH(O-)CCl)。
(2) in another there-necked flask, add 30g amido silicon oil (amine value: 0.40mmol/g; Viscosity (25 ℃): 8000cP), 2.00g 3-chloro-2-hydroxypropyl tetradecyl alkyl dimethyl ammonium chloride, 0.24g volatile caustic and 30ml Virahol; Reaction is 4 hours under 70 ℃ of conditions; Cooling removes by filter deposition, and underpressure distillation removes to desolvate and obtains title product (modified amino silicon oil).
(3) with the 6g emulsifying agent (by AEO (AEO-3): AEO (AEO-7)=1: 1 (mass ratio) composite making), 20g is mixed by modified amino silicon oil and the 74g deionized water that step (2) makes, emulsion, brief note emulsion B.
Wherein: AEO-3, AEO-7 provide by Shenzhen Tianding Fine Chemical Engineering Manufacturing Co., Ltd.
Embodiment 3
(1) in there-necked flask, adds 10ml concentrated hydrochloric acid and 50ml deionized water, under-10 ℃～0 ℃ condition, in this there-necked flask, drip 29.6g hexadecyldimethyl benzyl ammonium amine; Insulation (10 ℃～0 ℃) 3 hours is regulated pH value 7～8, under-20 ℃～0 ℃ condition; In this there-necked flask, drip epoxy chloropropane again, insulation (20 ℃～0 ℃ bar) 2 hours is warming up to 60 ℃; Reacted 5 hours, cooling, removing desolvates promptly obtains properties-correcting agent 3-chloro-2-hydroxypropyl hexadecyldimethyl benzyl ammonium ammonium chloride.
IR：3300(s，υO-H)，2918(s，υC-H)，2851(s，υC-H)，1469(m，δC-H)，950(w，υC-N)，721(w，δC-H)
1H-NMR(CDCl
3)(ppm)δ0.96(-CCH3)δ1.29-1.33(-CCH2)δ2.0(-OH)δ2.0(OH)δ1.73(-NCCH2C)δ3.24-3.30(-NCH3)δ3.274-3.52(-NCH2(CO-)CCl)δ3.65-3.402.51(-NCC(O-)CH2Cl)δ4.63(-NCCH(O-)CCl)。
(2) in another there-necked flask, add 30g amido silicon oil (amine value: 0.80mmol/g; Viscosity (25 ℃): 1500cP), 7.64g 3-chloro-2-hydroxypropyl hexadecyldimethyl benzyl ammonium ammonium chloride, 0.96g Pottasium Hydroxide and 30ml toluene; Reaction is 3 hours under 90 ℃ of conditions; Cooling removes by filter deposition, and underpressure distillation removes to desolvate and obtains title product (modified amino silicon oil).
(3) with the 6g emulsifying agent (by isomerous tridecanol polyoxyethylene ether (1350): isomerous tridecanol polyoxyethylene ether (1370)=1: 1 (mass ratio) composite making); 20g is mixed by modified amino silicon oil and the 74g deionized water that step (2) makes; Get emulsion, brief note emulsion C.
Wherein: 1350,1370 provide by Shenzhen Tianding Fine Chemical Engineering Manufacturing Co., Ltd.
Embodiment 4
(1) in there-necked flask, adds 10ml concentrated hydrochloric acid and 50ml Virahol, under 0 ℃～20 ℃ conditions, in this there-necked flask, drip 26.7g octadecyl dimethyl amine; Insulation (0 ℃～20 ℃) 3 hours is regulated pH value 8～9, under-20 ℃～0 ℃ condition; In this there-necked flask, drip epoxy chloropropane again, insulation (20 ℃～0 ℃) 2 hours is warming up to 50 ℃; Reacted 5 hours, cooling, removing desolvates promptly obtains properties-correcting agent 3-chloro-2-hydroxypropyl octadecyl alkyl dimethyl ammonium chloride.
IR：3300(s，υO-H)，2918(s，υC-H)，2851(s，υC-H)，1469(m，δC-H)，950(w，υC-N)，721(w，δC-H)
1H-NMR(CDCl
3)(ppm)δ0.96(-CCH3)δ1.29-1.33(-CCH2)δ2.0(-OH)δ2.0(OH)δ1.73(-NCCH2C)δ3.24-3.30(-NCH3)δ3.274-3.52(-NCH2(CO-)CCl)δ3.65-3.402.51(-NCC(O-)CH2Cl)δ4.63(-NCCH(O-)CCl)。
(2) in another there-necked flask, add 30g amido silicon oil (amine value: 1.00mmol/g; Viscosity (25 ℃): 1000cP), 6.39g 3-chloro-2-hydroxypropyl octadecyl alkyl dimethyl ammonium chloride, 0.30g calcium hydroxide and 30ml toluene; Reaction is 3 hours under 70 ℃ of conditions; Cooling removes by filter deposition, and underpressure distillation removes to desolvate and obtains title product (modified amino silicon oil).
(3) with the 6g emulsifying agent (by AEO (AEO-3): isomerous tridecanol polyoxyethylene ether (1370)=1: 1 (mass ratio) composite making), 20g is mixed by modified amino silicon oil and the 74g deionized water that step (2) makes, emulsion, brief note emulsion D.
Wherein: AEO-3,1370 provides by Shenzhen Tianding Fine Chemical Engineering Manufacturing Co., Ltd.
Embodiment 5
(1) in there-necked flask, adds 10ml concentrated hydrochloric acid and 80ml Virahol, under 0 ℃～20 ℃ conditions, in this there-necked flask, drip 26.0g octadecyl dimethyl amine; Insulation (0 ℃～20 ℃) 5 hours is regulated pH value 8～9, under 0 ℃～30 ℃ conditions; In this there-necked flask, drip epoxy chloropropane again, insulation (0 ℃～30 ℃) 2 hours is warming up to 70 ℃; Reacted 5 hours, cooling, removing desolvates promptly obtains properties-correcting agent 3-chloro-2-hydroxypropyl octadecyl alkyl dimethyl ammonium chloride.
IR：3300(s，υO-H)，2918(s，υC-H)，2851(s，υC-H)，1469(m，δC-H)，950(w，υC-N)，721(w，δC-H)
1H-NMR(CDCl
3)(ppm)δ0.96(-CCH3)δ1.29-1.33(-CCH2)δ2.0(-OH)δ2.0(OH)δ1.73(-NCCH2C)δ3.24-3.30(-NCH3)δ3.274-3.52(-NCH2(CO-)CCl)δ3.65-3.402.51(-NCC(O-)CH2Cl)δ4.63(-NCCH(O-)CCl)。
(2) in another there-necked flask, add 30g amido silicon oil (amine value: 1.60mmol/g; Viscosity (25 ℃): 5000cP), 7.16g 3-chloro-2-hydroxypropyl octadecyl alkyl dimethyl ammonium chloride, 0.74g hydrogen-oxygen potassium and 60ml toluene; Reaction is 8 hours under 90 ℃ of conditions; Cooling removes by filter deposition, and underpressure distillation removes to desolvate and obtains title product (modified amino silicon oil).
(3) with the 6g emulsifying agent (by AEO (AEO-9): isomerous tridecanol polyoxyethylene ether (1350)=1: 1 (mass ratio) composite making), 20g is mixed by modified amino silicon oil and the 74g deionized water that step (2) makes, emulsion, brief note emulsion E.
Wherein: AEO-9 and 1350 provides by Shenzhen Tianding Fine Chemical Engineering Manufacturing Co., Ltd.
Embodiment 6
The emulsion that makes in the foregoing description 1～5 is made into the solution of 40g/L respectively; Other gets the solution (control sample) that the amino silicon oil emulsion that the amine value is 0.60mmol/g, viscosity 5000cP (product content 20%, emulsion solid content 26%) is made into 40g/L.Bath raio is through one to soak a roll process at 1: 20 cotton fabric is carried out softening; 100 ℃ of down oven dry, 160 ℃ cure 3 minutes after, with the whiteness of WSB-6 blancometer mensuration fabric: please at least five people are blind touches for feel (flexibility and smooth property); Evaluation rank (wherein 6 grades best, 1 grade the poorest); Wetting ability adopts the water droplet osmosis to measure, and the result sees table 1.
Table 1
Claims (8)
1. modified amino silicon oil, it is made by the following preparation method of key step:
Under the condition that has mineral alkali to exist, reacted 3 hours～10 hours in 50 ℃～100 ℃ by amido silicon oil and formula I compound, obtain target compound;
Wherein, R
1, R
2And R
3In have one for C
10～C
20Chain-like alkyl is selected from and remain two: C
1～C
6A kind of in the chain-like alkyl; X is F, Cl, Br or I; The mol ratio of amido silicon oil and formula I compound is 1.0: 0.1～1.0: 10.0.
2. modified amino silicon oil as claimed in claim 1 is characterized in that, wherein R
1, R
2And R
3In have one for C
12～C
18Chain-like alkyl is selected from and remain two: C
1～C
3A kind of in the chain-like alkyl.
3. modified amino silicon oil as claimed in claim 2 is characterized in that, wherein R
1, R
2And R
3In have one for C
12～C
18Chain-like alkyl is methyl and remain two.
4. modified amino silicon oil as claimed in claim 3; It is characterized in that wherein used formula I compound is: 3-chloro-2-hydroxypropyl dodecyl dimethyl ammonium chloride, 3-chloro-2-hydroxypropyl tetradecyl alkyl dimethyl ammonium chloride, 3-chloro-2-hydroxypropyl hexadecyldimethyl benzyl ammonium ammonium chloride or 3-chloro-2-hydroxypropyl octadecyl alkyl dimethyl ammonium chloride.
5. modified amino silicon oil as claimed in claim 1 is characterized in that, wherein said mineral alkali is: volatile caustic, Pottasium Hydroxide, sodium hydroxide or calcium hydroxide; The mol ratio of amido silicon oil and mineral alkali is 1.0: 0.1～1.0: 10.0.
6. like any described modified amino silicon oil in the claim 1～5, it is characterized in that the weight-average molecular weight 500～100,000 of wherein used amido silicon oil; The amine value is: 0.05mmol/g～3.00mmol/g.
Like any described modified amino silicon oil in the claim 1～5 as the application of fabric finishing agent.
8. modified amino silicon oil as claimed in claim 6 is as the application of fabric finishing agent.
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| CN103724562A (en) * | 2013-11-08 | 2014-04-16 | 绍兴鼎翔纺织品贸易有限公司 | Preparation method of cationic hydrophilic modified amino silicone oil |
| CN105839415A (en) * | 2016-04-18 | 2016-08-10 | 广东湛丰精细化工有限公司 | Low-yellowing hydrophilic finishing agent and preparation method thereof |
| CN111286987B (en) * | 2020-02-24 | 2023-04-07 | 江苏大学 | Organic silicon quaternary ammonium salt fabric finishing agent based on block silicone oil and preparation method thereof |
| CN114672026A (en) * | 2022-04-25 | 2022-06-28 | 广东科峰新材料科技有限公司 | Quinary copolymerized super-soft and smooth hydrophilic silicone oil and synthetic method thereof |
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| EP2236661A1 (en) * | 2007-12-17 | 2010-10-06 | Jiangsu Redbud Textile Technology Co., Ltd. | Process for health-preserving hemp fiber and special health-preserving additive for jute fiber used therein |
| CN101265664A (en) * | 2008-04-24 | 2008-09-17 | 张家港市德宝化工有限公司 | Moisture absorption perspiration-discharging dressing agent and its manufacturing technique and application |
| CN101705524A (en) * | 2009-04-09 | 2010-05-12 | 品德实业(太原)有限公司 | Technique for changing characteristics of regenerated cellulose fibre |
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