CN111116920A - Branched polyamino long-chain alkyl polysiloxane, waterproof soft organic silicon finishing agent and preparation method thereof - Google Patents
Branched polyamino long-chain alkyl polysiloxane, waterproof soft organic silicon finishing agent and preparation method thereof Download PDFInfo
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- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
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- 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
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- C08G77/04—Polysiloxanes
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- C08G77/26—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen nitrogen-containing groups
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- D06M2200/12—Hydrophobic properties
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Abstract
The invention discloses a branched polyamino long-chain alkyl polysiloxane, a waterproof soft organic silicon finishing agent and a preparation method thereof, and belongs to the technical field of organic silicon finishing agents. The invention adopts a bulk polymerization mode, takes gamma-diethylenetriamine propyl methyl dimethoxy silane, long-carbon chain alkyl diethoxy silane, methyl triethoxy silane and octamethylcyclotetrasiloxane as raw materials, prepares branched polyamino long-chain alkyl polysiloxane through ring-opening polycondensation reaction under the catalysis of potassium hydroxide, mixes the branched polyamino long-chain alkyl polysiloxane and paraffin with a special melting point according to a certain proportion, heats the mixture, and emulsifies the mixture by using a mixed emulsifier to obtain the cationic organosilicon waterproof softener. When the composite is used together with an organic fluorine waterproof agent and applied to nylon textiles, the waterproof property is further improved, and the result shows that the flexibility and the waterproof agent are both good.
Description
Technical Field
The invention belongs to the technical field of organic silicon finishing agents, and particularly relates to a branched polyamino long-chain alkyl polysiloxane, a waterproof soft organic silicon finishing agent and a preparation method thereof.
Background
At present, people have higher and higher requirements on textiles for clothing, and besides wearing comfort and fashionable color, the textiles also need to have the functions of water resistance, oil resistance, wrinkle resistance, moisture permeability and the like.
At present, the textile waterproof finishing agent sold in the market is mainly based on organic silicon and organic fluorine, and the waterproof agent sold in a large amount in the market is mainly fluorine-containing waterproof agent, although the waterproof agent has good waterproof effect, the organic fluorine waterproof agent is expensive, high in production cost, complex in operation process and not beneficial to environmental protection.
Therefore, the research on the green, environment-friendly and pollution-free organosilicon waterproof softening agent becomes a hot spot in recent years. The organic silicon waterproof softening agent is economic and environment-friendly, simple in process flow and low in price, can be used together with an organic fluorine waterproof agent, and can improve the waterproof performance and hand feeling of textiles and increase the wearing comfort.
The existing organosilicon waterproof softening agent mainly has the following defects: firstly, the stability is poor, and the layering is easy; secondly, when the fabric is matched with a waterproof agent for use, the fabric has poor shearing resistance, and white spots are easily generated in continuous production.
Therefore, the research on the waterproof soft organic silicon finishing agent is very important.
Disclosure of Invention
The invention aims to solve the defects of the prior art and provides a branched polyamino long-chain alkyl polysiloxane, a waterproof soft organic silicon finishing agent and a preparation method thereof.
The invention adopts the following technical scheme:
the preparation method of branched polyamino long-chain alkyl polysiloxane comprises the following steps:
and (2) carrying out prepolymerization reaction on octamethylcyclotetrasiloxane, long-carbon-chain alkyl diethoxysilane and gamma-diethylenetriamine propyl methyl dimethoxysilane for 0.5-2 h at the temperature of 80-100 ℃ under the action of an alkaline catalyst, then carrying out vacuum pressure reduction reaction for 1-10 h, then adding methyl triethoxysilane, and carrying out vacuum pressure reduction reaction for 0.5-5 h to obtain the branched polyamino long-chain alkyl polysiloxane.
Further, the molar ratio of the added octamethylcyclotetrasiloxane, the long-carbon-chain alkyl diethoxysilane, the gamma-diethylenetriaminepropyl methyldimethoxysilane and the methyltriethoxysilane is 100: 0.1-1: 0.1-1: 0.01 to 0.3; the alkaline catalyst is potassium hydroxide or sodium hydroxide, and the vacuum degree during vacuum decompression reaction is 70 mbar.
Furthermore, the long-carbon-chain alkyl diethoxysilane is one or a mixture of more of linear chain or branched chain aliphatic hydrocarbon groups with alkyl carbon number of 18-28. The water resistance is not ideal below 18C or above 28C.
Still further, the long carbon chain alkyl diethoxysilane is a methyloctadecyldiethoxysilane or a methyloctacosyldiethoxysilane.
The invention also provides a waterproof soft organic silicon finishing agent, which comprises special melting point paraffin and the prepared branched polyamino long-chain alkyl polysiloxane;
the paraffin with the special melting point is paraffin with the melting point of 56-60 ℃, the waterproof performance is greatly reduced when the temperature is lower than 56 ℃, and the stability and the flexibility of a product higher than 60 ℃ can not meet the requirements.
Further, the mass ratio of the branched polyamino long-chain alkyl polysiloxane to the special melting-point paraffin is 1: 0.01-1: 10.
the invention also provides a preparation method of the waterproof soft organic silicon finishing agent, which comprises the following steps:
the method comprises the following steps: compounding branched polyamino long-chain alkyl polysiloxane and paraffin with a special melting point according to a mass ratio, and heating to 60 ℃ to obtain a mixture I;
step two: adding a mixed emulsifier accounting for 1-35% of the mass of the mixture I, stirring for 30min at 60 ℃, and slowly dripping water until the solid content of the emulsion is 32%.
Further, the mixed emulsifier in the second step is a mixture of a nonionic emulsifier and a cationic emulsifier.
Further, the nonionic emulsifier is at least one of AEO-7, TO-3 and IPL-1005, and the cationic emulsifier is at least one of 1831, 1631 and 1231.
The invention also provides application of the waterproof soft organic silicon finishing agent in fabric surface treatment.
Compared with the prior art, the invention has the beneficial effects that:
the invention adopts a bulk polymerization mode, takes gamma-diethylenetriamine propyl methyl dimethoxy silane, long-carbon chain alkyl diethoxy silane, methyl triethoxy silane and octamethylcyclotetrasiloxane (D4) as raw materials, and prepares branched polyamino long-chain alkyl polysiloxane through ring-opening polycondensation reaction under the catalysis of potassium hydroxide, and the branched polyamino long-chain alkyl polysiloxane and paraffin with a special melting point are mixed according to a certain proportion, heated to 60 ℃, emulsified by using a mixed emulsifier, and the cationic organosilicon waterproof softener T732 is obtained. The paraffin structure is similar to the long-chain alkane structure in branched polyamino long-chain alkyl polysiloxane, a double-layer waterproof structure is formed after the film is formed on the surface of the fabric, and meanwhile, the T732 has good flexibility because the Si-O bond is a covalent bond with the ionic bond characteristic of 50%. When the composite is used together with an organic fluorine waterproof agent and applied to nylon textiles, the waterproof property is further improved, and the result shows that the flexibility and the waterproof agent are both good.
Drawings
FIG. 1 shows H of a branched polyamino long-chain alkylpolysiloxane prepared in example 1 of the invention1NMR spectrum, as seen from the figure, strong-CH appears around. delta. ═ 1.3ppm2Methylene absorption peak, in the vicinity of 0.88ppm, -CH3Methyl peak, it can be shown that long chain alkyl methyl diethoxysilane reacts onto the backbone. 0.1ppm Si-CH present3The silicon methyl peak, is the characteristic peak of the silane backbone.
FIG. 2 is a Si-NMR spectrum of a branched polyamino long-chain alkylpolysiloxane prepared in example 1 of the present invention, showing that the chemical shift is at the-20 position, which is represented by-Si-O2Linear structure with small peak at-69 position and belonging to-Si-O3Branched structure, the introduction of a main chain branched structure can be seen.
Detailed Description
The present invention will be described in further detail with reference to examples.
It will be appreciated by those skilled in the art that the following examples are illustrative of the invention only and should not be taken as limiting the scope of the invention.
The fabric used in the invention is nylon yarn woven fabric.
The drugs used in the present invention are as follows:
waterproof finishing agent DH-3665, waterproof finishing agent DH-3645, waterproof finishing agent 608E, waterproof finishing agent AD-9, cross-linking agent DH-8913 (the above medicines are all provided by Guangdong Germany fine chemical industry Co., Ltd.);
octamethylcyclotetrasiloxane (D4) (available from Nemontage Hengcheng Silicone Co., Ltd.), gamma-diethylenetriaminopropylmethyldimethoxysilane (available from Wake chemical (China) Co., Ltd.), long-chain alkyl diethoxysilane (available from Wake chemical (China) Co., Ltd.), methyltriethoxysilane (available from Wake chemical (China) Co., Ltd.), potassium hydroxide, emulsifiers AEO-7, TO-3, Pasteur (China) Co., Ltd.; IPL-1005, Linhong New materials science and technology Co., Ltd; emulsifiers 1831, 1631 and 1231, Shandong Zhonghai chemical group Co., Ltd.), and paraffin wax (56-60 ℃ C.) (supplied by Wacker chemical (China) Co., Ltd.).
The apparatus involved in the invention is as follows:
P-AO electric padders (Mathis);
a Rapid setting machine (mansion door Rapid); oven (Shanghai Instrument Master);
water resistance tester (Wenzhou circumference Instrument Co., Ltd.).
A Nano-particle size potential analyzer (Malvern, Nano-ZS90), viscometer (brokfield, DV2T LVTJ 0).
High shear homogenizer (Eki).
Example 1
Preparation of branched polyamino long-chain alkylpolysiloxane: adding 500g of octamethylcyclotetrasiloxane, 20g of methyl octadecyl diethoxysilane and 5g of gamma-diethylenetriaminepropyl methyldimethoxysilane into a reaction vessel, carrying out prepolymerization reaction for 0.5h, carrying out vacuum pressure reduction reaction for 3h, adding 1.5g of methyl triethoxysilane, and carrying out vacuum pressure reduction reaction for 0.5h under the action of a basic catalyst potassium hydroxide (the addition amount is 0.1g) at 80 ℃;
mixing branched polyamino long-chain alkyl polysiloxane and 56 ℃ melting-point paraffin according to a mass ratio of 1: 0.1 compounding, and heating to 60 ℃ to obtain a mixture I;
adding 1% of AEO-7, 3% of TO-3, 8% of IPL-1005 and 1% of 1231% of mixed emulsifier in the mass of the mixture I, stirring for 30min at 60 ℃, and slowly dripping water until the solid content of the emulsion is 32% TO obtain the waterproof soft organic silicon finishing agent T732.
Example 2
Preparation of branched polyamino long-chain alkylpolysiloxane: adding 500g of octamethylcyclotetrasiloxane, 10g of methyl octacosyl diethoxysilane and 15g of gamma-diethylenetriaminopropyl methyldimethoxysilane into a reaction vessel, carrying out prepolymerization reaction for 1h under the action of a basic catalyst potassium hydroxide (the addition amount is 0.1g) at 80 ℃, carrying out vacuum pressure reduction reaction for 9h, adding 0.5g of methyl triethoxysilane, and carrying out vacuum pressure reduction reaction for 1h to obtain the product;
mixing branched polyamino long-chain alkyl polysiloxane and 56 ℃ melting-point paraffin according to a mass ratio of 1: 0.2 compounding, and heating to 60 ℃ to obtain a mixture I;
adding 2% of AEO-7, 6% of TO-3, 8% of IPL-1005 and 1% of 1831 mixed emulsifier in the mass of the mixture I, stirring for 30min at 60 ℃, and slowly dripping water until the solid content of the emulsion is 32% TO obtain the waterproof soft organic silicon finishing agent T732.
Example 3
Preparation of branched polyamino long-chain alkylpolysiloxane: adding 500g of octamethylcyclotetrasiloxane, 10g of methyl octacosyl diethoxysilane and 15g of gamma-diethylenetriaminopropyl methyldimethoxysilane into a reaction vessel, carrying out prepolymerization reaction for 1h under the action of a basic catalyst potassium hydroxide (the addition amount is 0.1g) at 80 ℃, carrying out vacuum reduced pressure reaction for 9h, adding 2g of methyltriethoxysilane, and carrying out vacuum reduced pressure reaction for 0.5h to obtain the final product;
mixing branched polyamino long-chain alkyl polysiloxane and 60 ℃ melting-point paraffin according to a mass ratio of 1: 1, compounding, and heating to 60 ℃ to obtain a mixture I;
adding 10% of AEO-7, 6% of TO-3, 10% of IPL-1005 and 1% of 1631% of mixed emulsifier in the mass of the mixture I, stirring for 30min at 60 ℃, and slowly dripping water until the solid content of the emulsion is 32% TO obtain the waterproof soft organic silicon finishing agent T732.
Chemical characteristics and characterization of waterproof softening silicone finish T732:
appearance: observed directly with the naked eye.
pH value of the emulsion: measured with a pH meter.
Solid content: weighing 1-2 g (accurate to +/-0.0001 g) of the prepared emulsion by using an analytical balance, placing the emulsion in a constant-temperature drying and blasting oven at 120-130 ℃ until the weight is constant, taking out the emulsion, and calculating the solid content of the emulsion.
Centrifugal stability: measuring 10mL of an emulsion sample, adding the emulsion sample into a centrifugal test tube, then placing the tube into a high-speed centrifuge, centrifuging the tube for 20-30 min at 3000r/min, taking out the tube, and observing whether the emulsion can generate phenomena such as oil floating, skinning or layering.
The waterproof soft organic silicon finishing agent T732 prepared in the embodiment 1 of the invention is applied as follows:
waterproof finishing process and technological parameters
Water-proofing agent: Xg/L, (different types of water repellents are used);
T732：Xg/L；
dipping → passing rollers (one dipping and one rolling, 2kg pressure) → sizing (170 ℃. times.90 s) → testing of the water-repellent effect after moisture regain and the comparative hand.
The production process parameters are as follows:
the rolling allowance is as follows: 28% +/-10%;
liquid rolling: horizontal padder, pressure 2kg/cm2The vehicle speed is 5 r/min;
setting temperature and time: keeping the temperature at 170 ℃ for 90 seconds;
second, measuring the performance of the finished cloth sample
And (3) placing the finished cloth sample under the environmental conditions of temperature (20 +/-2) DEG C and relative humidity (65 +/-2)% for balancing for 24h, and carrying out performance measurement.
The static contact angle of water drops on the surface of the cloth sample is used for representing the waterproof effect, and a waterproofness tester is used for measuring; reference AATCC 22-1997 Water repellency tests: the spray method evaluates the waterproof rating of the fabric after emulsion finishing.
Third, result and discussion
1. Physicochemical properties of T732 emulsion
The performance of T732 was tested at ambient temperature of 25 ℃ and the results are shown in table 1.
TABLE 1 physicochemical Properties of T732 emulsions
| Appearance of the product | Solid content/%) | pH value | Centrifugal stability | Stability in standing |
| Milky white liquid | 32 | 5～6 | Good effect | Good effect |
As seen from the data in Table 1, the T732 emulsion is a milky white liquid, the emulsion is uniform, the solid content is 32%, no layering or oil floating phenomenon occurs, and the centrifugal stability and the standing stability are good.
2. Waterproof effect of T732 emulsion and waterproof agent
TABLE 2 combination effect of T732 emulsion and DH-3665
As shown in the data of Table 2, the T732 emulsion is combined with a waterproof agent DH-3665, and the waterproof effect of the finished fabric is improved along with the increase of the dosage of the T732 emulsion.
TABLE 3 combination of T732 emulsion with 608E
As can be seen from the data in Table 3, the T732 emulsion is combined with the water repellent 608E, and the water repellent effect of the finished fabric is improved along with the increase of the dosage of the T732 emulsion.
TABLE 4 combination effect of T732 emulsion and DH-3645
As shown in the data in Table 4, the T732 emulsion is combined with a waterproof agent DH-3645, and the waterproof effect of the finished fabric is improved along with the increase of the dosage of the T732 emulsion.
TABLE 5 combination of T732 emulsion with AD-9
As shown in the data of Table 5, when the T732 emulsion is combined with the waterproofing agent AD-9, the waterproofing effect of the finished fabric is improved along with the increase of the dosage of the T732 emulsion.
3. Waterproof and washable effect of T732 emulsion and waterproof agent
TABLE 6 NYLON 4-STAGE WATER-PROOF FORMULATION AND WASHING RESISTANCE
As seen from the data in Table 6, T732 has no influence on the waterproof and washable performances, and can greatly improve the phenomenon that the hand feeling of the fabric is hard after finishing by the waterproof agent.
4. Application of T732 emulsion in shade-drying waterproof finishing of nylon textile
TABLE 7 Water resistance test by drying in the shade
As seen from the data in Table 7, T732 has no influence on the water resistance and washfastness of the shade drying, and can greatly improve the phenomenon that the hand feeling of the fabric is hard after the finishing by the waterproof agent and the crosslinking agent.
5. Test of shear stability Using DH-3645 waterproofing agent as example
20g/L of the waterproof agent DH-3645, respectively preparing 200mL of working solution by using tap water at about 45 ℃, 300ppm of hard water and 300ppm of hard water plus T732(20g/L), putting the working solution into a 500mL beaker, stirring the working solution for 5min (the rotating speed is 2000rpm) by using a high-shear stirrer (a stirring head is a stainless steel blade), performing suction filtration on the working solution by using a vacuum pump (240T Chunzea suction filtration), and observing the stability according to comparison of the amount of white residues on blue Chunzea.
TABLE 8 shear stability test
As seen from the data in Table 8, the combination of T732 and DH-3645 can improve the hard water resistance stability and shear resistance stability of DH-3645.
Therefore, the waterproof soft organic silicon finishing agent T732 prepared by the invention has a certain improvement effect on the waterproof effect when being used together with different types of waterproof agents, not only can improve the hard water resistance and the shear resistance stability of the waterproof agent, but also can improve the hand feeling of the fabric to ensure that the fabric becomes soft and fine; t732 has little influence on the washing resistance of the waterproof agent and can be applied to high-requirement shade-drying waterproof finishing.
It will be understood by those skilled in the art that the present invention is not limited to the embodiments described above, which are described in the specification and illustrated only to illustrate the principle of the present invention, but that various changes and modifications may be made therein without departing from the spirit and scope of the present invention, which fall within the scope of the invention as claimed. The scope of the invention is defined by the appended claims and equivalents thereof.
Claims (10)
1. A preparation method of branched polyamino long-chain alkyl polysiloxane is characterized by comprising the following steps:
and (2) carrying out prepolymerization reaction on octamethylcyclotetrasiloxane, long-carbon-chain alkyl diethoxysilane and gamma-diethylenetriamine propyl methyl dimethoxysilane for 0.5-2 h at the temperature of 80-100 ℃ under the action of an alkaline catalyst, then carrying out vacuum pressure reduction reaction for 1-10 h, then adding methyl triethoxysilane, and carrying out vacuum pressure reduction reaction for 0.5-5 h to obtain the branched polyamino long-chain alkyl polysiloxane.
2. The method for preparing branched polyamino long-chain alkyl polysiloxane according to claim 1, wherein the molar ratio of octamethylcyclotetrasiloxane, long-chain alkyl diethoxysilane, gamma-diethylenetriaminepropylmethyldimethoxysilane and methyltriethoxysilane added is 100: 0.1-1: 0.1-1: 0.01 to 0.3; the alkaline catalyst is potassium hydroxide or sodium hydroxide, and the vacuum degree during vacuum decompression reaction is 70 mbar.
3. The method for preparing branched polyamino long-chain alkyl polysiloxane according to any one of claims 1 to 2, wherein the long-chain alkyl diethoxysilane is one or more of linear or branched aliphatic hydrocarbon groups with alkyl carbon number of 18-28.
4. The method for producing a branched polyamino long-chain alkyl polysiloxane according to claim 3, wherein said long-chain alkyl diethoxysilane is a methyloctadecyldiethoxysilane or a methyloctacosyldiethoxysilane.
5. A waterproof soft organic silicon finishing agent is characterized in that:
comprising a paraffin wax having a specific melting point and a branched polyamino long-chain alkylpolysiloxane prepared according to claim 1;
the paraffin with the special melting point is paraffin with the melting point of 56-60 ℃.
6. The waterproof soft silicone finish of claim 5, characterized in that:
the mass ratio of the branched polyamino long-chain alkyl polysiloxane to the special melting point paraffin is 1: 0.01-1: 10.
7. the method for preparing the waterproof soft silicone finishing agent according to claim 5, characterized by comprising the steps of:
the method comprises the following steps: compounding branched polyamino long-chain alkyl polysiloxane and paraffin with a special melting point according to a mass ratio, and heating to 60 ℃ to obtain a mixture I;
step two: adding a mixed emulsifier accounting for 1-35% of the mass of the mixture I, stirring at 60 ℃ for 30min, and slowly dripping water until the solid content of the emulsion is 32%.
8. The method for preparing the waterproof soft silicone finishing agent according to claim 7, wherein the mixed emulsifier in the second step is a mixture of a nonionic emulsifier and a cationic emulsifier.
9. The method of claim 8, wherein the nonionic emulsifier is at least one of AEO-7, TO-3 and IPL-1005, and the cationic emulsifier is at least one of 1831, 1631 and 1231.
10. Use of the water repellent softening silicone finish of claim 5 in the treatment of fabric surfaces.
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| CN114232170A (en) * | 2021-11-09 | 2022-03-25 | 海利得新材料研究(上海)有限公司 | Anti-wicking agent combination for airtight waterproof cloth and spinning equipment |
| CN114349967A (en) * | 2021-12-29 | 2022-04-15 | 惠州瑞德新材料科技股份有限公司 | Amino-hydrocarbon-based silicone wax resin emulsion, paper-based material waterproofing agent and preparation method |
| CN114575162A (en) * | 2021-12-29 | 2022-06-03 | 广东传化富联精细化工有限公司 | Preparation method of composite waterproof breathable after-finishing agent, product and application |
| CN114957670A (en) * | 2022-06-23 | 2022-08-30 | 佛山市顺德区德美瓦克有机硅有限公司 | Highly-branched cross-linked polysiloxane and waterproof agent |
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| CN114941244B (en) | 2023-12-22 |
| CN114941244A (en) | 2022-08-26 |
| CN111116920B (en) | 2022-06-21 |
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