CN110055760B - Polyester fabric deepening agent containing modified silicone oil and preparation method thereof - Google Patents
Polyester fabric deepening agent containing modified silicone oil and preparation method thereof Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
- C08G77/26—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen nitrogen-containing groups
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/38—Polysiloxanes modified by chemical after-treatment
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- D06M11/74—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with carbon or compounds thereof with carbon or graphite; with carbides; with graphitic acids or their salts
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- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
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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
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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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
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- 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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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M2101/00—Chemical constitution of the fibres, threads, yarns, fabrics or fibrous goods made from such materials, to be treated
- D06M2101/16—Synthetic fibres, other than mineral fibres
- D06M2101/30—Synthetic polymers consisting of macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M2101/32—Polyesters
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Abstract
The invention belongs to the technical field of organic silicone oil, and particularly relates to a preparation method and application of modified silicone oil. Piperazine and chloromethyl dimethylethoxysilane are used as raw materials to prepare piperazine terminated siloxane, the piperazine terminated siloxane and octamethylcyclotetrasiloxane are used to prepare piperazine terminated polydimethylsiloxane, and finally, amino in piperazine and double bonds in hydroxyethyl methacrylate are used for addition reaction to prepare modified silicone oil; the modified silicone oil prepared by the invention can be used as a polyester fabric deepening agent, especially an emulsion compounded with graphene quantum dots, the deepening effect of the polyester fabric is greatly enhanced, and the apparent color depth value can be improved by 49.6%.
Description
Technical Field
Original application No. 2018111120128, entitled preparation method and application of modified silicone oil, filed 2018.09.25. The invention belongs to the technical field of organic silicone oil, and particularly relates to a deepening agent containing modified silicone oil for polyester fabrics and a preparation method thereof.
Background
With the rapid development of chemical fibers, the varieties of beneficial textiles are gradually increased, the clothing materials of people are greatly enriched, and the method plays a great role in promoting the development of national economy. The terylene in the synthetic fiber is popular because of the advantages of high strength, good elasticity, good dimensional stability, easy washing, quick drying, firmness and durability, etc. However, since terylene does not contain hydrophilic groups, has low hygroscopicity and low swelling degree in water, and lacks polar groups in the chemical structure, the terylene is difficult to combine with dyes, and thus dyeing of terylene fibers is relatively difficult.
The adoption of a low-refractive-index deepening agent is an effective method for deepening polyester fabrics, and CN200810060886.3 discloses a fiber deepening agent emulsion and a preparation method thereof, wherein N-hydroxymethyl acrylamide is adopted as an initiator in the preparation process of the deepening agent; in 2017, 10 and 27, the carcinogen list published by the international cancer research institution of the world health organization is preliminarily collated and referred, and the N-methylolacrylamide is in the 3-class carcinogen list, so the cancer-causing risk exists in the deepening agent. CN 201010288531.7 discloses a darkening and brightening finishing agent for dyed cotton fabrics and a preparation method thereof, but the treatment object of the patent is mainly to carry out darkening and brightening treatment on the dyed cotton fabrics, and as the emulsifier in the synthesis process is all cationic emulsifier containing quaternary ammonium salt, the darkening and brightening treatment effect on the dyed cotton fabrics is good, but the synergy effect on polyester fabrics is not ideal.
Disclosure of Invention
The invention aims to provide a novel environment-friendly deepening agent emulsion with excellent deepening effect on polyester fabrics; piperazine and chloromethyl dimethylethoxysilane are used as raw materials to prepare piperazine terminated siloxane, the piperazine terminated siloxane and octamethylcyclotetrasiloxane (D4 for short) are used to prepare piperazine terminated polydimethylsiloxane, and finally, amino in piperazine and double bonds in hydroxyethyl methacrylate are used for addition reaction to prepare modified silicone oil; the modified silicone oil prepared by the invention can be used as a polyester fabric deepening agent, and particularly can be used as an emulsion compounded with graphene quantum dots, so that the deepening effect of the polyester fabric is greatly enhanced.
According to a first aspect of the present invention, there is provided a method for preparing a modified silicone oil, comprising the steps of:
1) adding piperazine (172.0g, 2.0mol) into 400ml dioxane, stirring uniformly at 50-60 ℃, then dropwise adding chloromethyl dimethylethoxysilane (61.1g, 0.4mol), controlling the dropwise adding time to be 1-2h, and carrying out reflux reaction for 3-4h after dropwise adding; after the reaction is finished, cooling to 0-5 ℃, filtering, collecting filtrate, concentrating the filtrate at 60-70 ℃ until no fraction is evaporated, then rectifying the filtrate at 110 ℃ and 8mbar to obtain alpha-piperazine methyl dimethyl ethoxy silane, putting the alpha-piperazine methyl dimethyl ethoxy silane into 2mmol/L acetic acid aqueous solution, carrying out hydrolytic polycondensation reaction at 50-60 ℃, and distilling the mixture for 6-8 hours to obtain 64.3g of transparent piperazine end-capped siloxane liquid;
the reaction formula is shown as Scheme 1:
2) 10.0g of piperazine-terminated siloxane, 50.0g of octamethylcyclotetrasiloxane and 2mg of tetramethylammonium hydroxide react for 8-12h at 90-100 ℃, then the temperature is raised to 130-140 ℃ for reaction for 20-30min, the tetramethylammonium hydroxide is removed by thermal decomposition, and the piperazine-terminated polydimethylsiloxane is obtained by reduced pressure distillation; the reaction formula is shown as Scheme 2:
3) Dissolving piperazine-terminated polydimethylsiloxane into toluene, adding hydroxyethyl methacrylate, refluxing for 6-8h, and distilling to remove toluene after the reaction is finished to obtain modified silicone oil; calculated according to the weight ratio, the piperazine-terminated polydimethylsiloxane in the step 3): hydroxyethyl methacrylate 3-8: 1; the invention utilizes the addition reaction of the secondary amino group in the piperazine-terminated polydimethylsiloxane and the double bond in the hydroxyethyl methacrylate to achieve the modification effect, and the reaction formula is shown as Scheme 3:
preferably, the piperazine-terminated polydimethylsiloxane in step 3) is: hydroxyethyl methacrylate 5-7: 1; the invention can adjust the weight ratio of piperazine-terminated polydimethylsiloxane to hydroxyethyl methacrylate to prepare different hydroxyethyl methacrylate modified silicone oil;
according to another aspect of the invention, the invention provides application of modified silicone oil in preparing a deepening agent emulsion for polyester fabrics.
Preferably, the deepening agent emulsion for the polyester fabric comprises the following substances in parts by weight: 10-15 parts of modified silicone oil, 1-3 parts of fatty alcohol-polyoxyethylene ether surfactant, 200 parts of purified water and 12-15 parts of polyethylene glycol;
preferably, the deepening agent emulsion for the polyester fabric further comprises 0.3-0.5 part by weight of graphene quantum dots; the graphene quantum dots are hydroxylated graphene quantum dots, carboxylated graphene quantum dots, oxidized graphene quantum dots or aminated graphene quantum dots, and preferably hydroxylated graphene quantum dots; the graphene quantum dot particles can be attached to the surface of the polyester fabric, so that the scattering and projection of light are increased, and the deepening effect is achieved; the deepening agent emulsion for the polyester fabric, which is obtained by compounding the graphene quantum dots and the modified silicone oil, has a synergistic effect in the aspect of deepening performance, and particularly the deepening effect is remarkably improved when the hydroxylated graphene quantum dots are adopted.
The fatty alcohol polyoxyethylene ether surfactant is a linear fatty alcohol polyoxyethylene ether surfactant or an isomeric tridecanol polyoxyethylene ether surfactant; the straight-chain fatty alcohol polyoxyethylene ether surfactant is AEO-1, AEO-2, AEO-3, AEO-5, AEO-7, AEO-9, AEO-15, AEO-20 or AEO-40; the isomeric tridecanol polyoxyethylene ether surfactant is fatty alcohol polyoxyethylene ether surfactant such as MULTIISO 13/30, MULTIISO 13/40, MULTIISO 13/50, MULTIISO 13/60, MULTIISO 13/70, MULTIISO 13/80, MULTIISO 13/90 or MULTIISO 13/100;
the invention has the following beneficial effects:
1) the modified silicone oil is obtained by adding amino and double bonds of piperazine-terminated polydimethylsiloxane and hydroxyethyl methacrylate for the first time, and can be used as a deepening agent for polyester fabrics;
2) the raw materials are green and do not contain carcinogenic components in the process of preparing the modified silicone oil;
3) the principle that graphene quantum dots can be attached to the surface of the polyester fabric to increase light scattering and projection so as to play a role in deepening is utilized; the graphene quantum dots and the modified silicone oil are compounded, the types of the graphene quantum dots are optimized, and the compounding of the hydroxylated graphene quantum dots and the modified silicone oil can enable the improvement rate of the K/S value of the polyester fiber to reach 49.6%;
4) the deepening agent emulsion prepared by compounding the modified silicone oil and the hydroxylated graphene quantum dots has excellent deepening performance, and the content of the hydroxylated graphene quantum dots in the deepening agent emulsion is only about 0.3%.
Detailed Description
Hydroxylated graphene quantum dots (cat # 100753) and carboxylated graphene quantum dots (cat # 102260), oxidized graphene quantum dots (cat # 102063), aminated graphene quantum dots (cat # 100755), graphene quantum dots (cat # 102088), nano titanium dioxide (cat # 100359), nano silicon dioxide (cat # 100361) and KH550 surface-treated nano silicon dioxide (cat # 100365) used in the examples are all from the Nanjing Xiancheng nanomaterial science and technology Co., Ltd;
apparent color depth (K/S) value: and testing the change of the K/S value before and after finishing the dyed fabric by using a spectrocolorimeter. And (3) folding the fabric to be measured into four layers, measuring on a spectrocolorimeter, and measuring for 4 times to obtain an average value.
Example 1 optimization of raw material ratio of modified Silicone oil
Firstly, preparing modified silicone oil:
1) adding 172.0g of piperazine into 400ml of dioxane, stirring uniformly at 50-60 ℃, then dropwise adding 61.1g of chloromethyl dimethylethoxysilane, controlling the dropwise adding time to be 1-2h, and carrying out reflux reaction for 3-4h after the dropwise adding is finished; after the reaction is finished, cooling to 0-5 ℃, filtering, collecting filtrate, concentrating the filtrate at 60-70 ℃ until no fraction is evaporated, then rectifying the filtrate at 110 ℃ and 8mbar to obtain alpha-piperazine methyl dimethyl ethoxy silane, putting the alpha-piperazine methyl dimethyl ethoxy silane into 2mmol/L acetic acid aqueous solution, carrying out hydrolytic polycondensation reaction at 50-60 ℃, and distilling the mixture after 6-8 hours to obtain transparent piperazine end-capped siloxane liquid;
2) 10.0g of piperazine-terminated siloxane, 50.0g of octamethylcyclotetrasiloxane and 2mg of tetramethylammonium hydroxide react for 8-12h at 90-100 ℃, then the temperature is raised to 130-140 ℃ for reaction for 20-30min, the tetramethylammonium hydroxide is removed by thermal decomposition, and the piperazine-terminated polydimethylsiloxane is obtained by reduced pressure distillation;
3) dissolving piperazine-terminated polydimethylsiloxane into toluene, adding hydroxyethyl methacrylate, refluxing for 6-8h, and distilling to remove toluene after the reaction is finished to obtain modified silicone oil; calculated according to the weight ratio, the piperazine-terminated polydimethylsiloxane: hydroxyethyl methacrylate 3-8: 1.
Secondly, modified silicone oil prepared from piperazine-terminated polydimethylsiloxane and hydroxyethyl methacrylate in different weight ratios is prepared into emulsion, and the method comprises the following steps:
stirring and dispersing 10 parts by weight of modified silicone oil and 160 parts by weight of purified water by using a high-speed shearing dispersion emulsifying machine, then adding 2 parts by weight of fatty alcohol polyoxyethylene ether surfactant AEO-20, stirring for 1-2 hours at the rotating speed of 6000rpm, heating to 40-60 ℃, adding 12 parts by weight of glycol, stirring for 6-8 hours at the rotating speed of 2000rpm, and cooling to room temperature to obtain the deepening agent emulsion for the polyester fabric, wherein the weight ratio of the polydimethylsiloxane end-capped by different piperazines to the hydroxyethyl methacrylate is different.
Thirdly, finishing the dyed black polyester fabric (the K/S value of which is 18.68) by adopting different piperazine-terminated Polydimethylsiloxane (PTSO) and hydroxyethyl methacrylate (HEMA) weight ratios of the polyester fabric-used deepening agent emulsion, wherein the method comprises the following steps: the method comprises the following steps of completely immersing dyed black polyester fabrics in a deepening agent emulsion for soaking for 30min, then carrying out double immersion and double rolling (the rolling residual rate is 90%), pre-drying at 80 ℃ for 120 seconds, baking at 160 ℃ for 120 seconds, and measuring the apparent color depth (K/S) value of the finished black polyester fabrics, wherein the deepening effect of the deepening agent emulsion for polyester fabrics in different weight ratios of piperazine-terminated polydimethylsiloxane and hydroxyethyl methacrylate is shown in Table 1:
TABLE 1 Effect of modified Silicone oil Material formulation on the darkening Effect of the darkening agent emulsion
Note: PTSO/HEMA refers to the weight ratio of piperazine-terminated Polydimethylsiloxane (PTSO) to hydroxyethyl methacrylate (HEMA) in the step 3) of the preparation process of the modified silicone oil.
The test result shows that the weight ratio of the piperazine-terminated Polydimethylsiloxane (PTSO) to the hydroxyethyl methacrylate (HEMA) has larger influence on the performance of the prepared deepening agent emulsion, when the hydroxyethyl methacrylate is not added, the deepening effect of the deepening agent emulsion is not obvious, and the apparent color depth (K/S) value is only improved by 2.0 percent; when PTSO/HEMA is 5-7, the darkening effect is significantly improved, increasing the apparent color depth (K/S) value by about 26%.
Example 2 formula weight part ratio optimization of deepening agent emulsion
After the weight ratio of the piperazine-terminated Polydimethylsiloxane (PTSO) to the hydroxyethyl methacrylate (HEMA) in the preparation process of the modified silicone oil is determined to be 6:1, the weight ratio of each component in the formula of the deepening agent emulsion is further optimized, and the dyed black polyester fabric (the K/S value of which is 18.68) is finished, so that the deepening effect can be improved, and the formula list and the deepening effect are shown in Table 2:
TABLE 2 Effect of weight ratio of formulation of deepening agent emulsion on deepening effect
| Modified silicone oil | Surfactant/(parts by weight) | Purified water | Polyethylene glycol | Rate of change of K/S value% |
| 10 | AEO-2(1) | 100 | 12 | 24.67％ |
| 11 | AEO-9(1) | 100 | 12 | 24.99％ |
| 12 | AEO-15(2) | 100 | 12 | 26.76％ |
| 13 | AEO-20(2) | 100 | 12 | 27.48％ |
| 14 | MULTISO13/50(3) | 100 | 13 | 26.87％ |
| 15 | MULTISO13/70(2) | 100 | 14 | 26.89％ |
| 16 | MULTISO13/90(2) | 100 | 15 | 25.64％ |
The concentration of the modified silicone oil in the deepening agent emulsion is adjusted by changing the adding amount of the modified silicone oil, and the deepening effect can be improved by changing the type of the surfactant, but the deepening effect is not obviously improved. The invention tries to adhere inert nano particles on the surface of the black polyester fabric and improves the color depth by reducing the reflection or refraction of light.
Example 3 inert nanoparticle species selection
Preparing 100ml of 1mg/ml aqueous dispersion of different nanoparticles, and then adding 15mg of AEO-20 surfactant to prepare the dispersion of different nanoparticles after ultrasonic dispersion for 2 hours; the dyed black polyester fabric (the K/S value of which is 18.68) is completely immersed in the nano particle dispersion liquid for soaking for 30min, then the dyed black polyester fabric is subjected to secondary immersion and secondary rolling (the rolling residual rate is 90%), after the dyed black polyester fabric is pre-dried for 120 seconds at 90 ℃, the apparent color depth (K/S) value of the finished black polyester fabric is measured after the dyed black polyester fabric is baked for 120 seconds at 160 ℃, and the darkening effects of different nano particles are shown in Table 3:
TABLE 3 deepening effect of different nano-particles on polyester fabric
Different kinds of inert nano particles can play a role in deepening polyester fibers to different degrees, particularly graphene quantum dots; except for the graphene oxide quantum dots, the lifting rate of the graphene quantum dots and the graphene quantum dots modified by hydroxyl, carboxyl and amino of the graphene quantum dots to K/S reaches about 20%; the hydroxylated graphene quantum dot has the most excellent deepening effect, and the K/S value lifting rate reaches 26.98%.
Example 4 compounding of modified silicone oil and hydroxylated graphene quantum dots
Stirring and dispersing 10g of modified silicone oil (PTSO/HEMA is 6:1) and 100g of purified water by a high-speed shearing dispersion emulsifying machine, then adding 2g of AEO-20 type surfactant and 0.3g of hydroxylated graphene quantum dots, stirring for 1-2h at the rotating speed of 6000rpm, heating to 40-60 ℃, adding 12 parts by weight of ethylene glycol, stirring for 6-8h at the rotating speed of 2000rpm, and cooling to room temperature to obtain the deepening agent emulsion for the polyester fabric, wherein the modified silicone oil and the hydroxylated graphene quantum dots are compounded; the dyed black polyester fabric (with a K/S value of 18.68) is used as a treatment object, and the compounded polyester fabric is finished by the deepening agent emulsion, and the deepening effect is tested, and the result is shown in Table 4:
table 4 influence of complex pairing of modified silicone oil and hydroxylated graphene quantum dots on deepening effect
| Deepening agent | K/S value | Delta K/S (color depth variation) | Rate of change of K/S value% |
| Compounding | 27.95 | 9.27 | 49.6％ |
| Modified silicone oil alone | 23.52 | 4.84 | 20.58％ |
| Hydroxylation-only graphene quantum dots | 22.94 | 4.26 | 22.80％ |
Note: compounding refers to the deepening agent emulsion for the polyester fabric prepared according to the steps in the embodiment 4; the modified silicone oil is only that 0.3g of hydroxylated graphene quantum dots are not added in the preparation process of the embodiment 4; the only hydroxylation of the graphene quantum dots means that 10g of modified silicone oil is not added in the preparation process of the example 4.
The test results show that the compounding of the hydroxylated graphene quantum dots and the modified silicone oil prepared by the method can greatly improve the deepening effect of the polyester fabric, the hydroxylated graphene quantum dots and the modified silicone oil have serious interaction and synergy, and the K/S value of the polyester fabric is increased by 49.6% without optimization.
The above embodiments are preferred embodiments of the present invention, but the present invention is not limited to the above embodiments, and any other changes, modifications, substitutions, combinations, and simplifications which do not depart from the spirit and principle of the present invention should be construed as equivalents thereof, and all such changes, modifications, substitutions, combinations, and simplifications are intended to be included in the scope of the present invention.
Claims (2)
1. A preparation method of modified silicone oil comprises the following steps:
1) adding 172.0g of piperazine into 400ml of dioxane, stirring uniformly at 50-60 ℃, then dropwise adding 61.1g of chloromethyl dimethylethoxysilane, controlling the dropwise adding time to be 1-2h, and carrying out reflux reaction for 3-4h after the dropwise adding is finished; after the reaction is finished, cooling to 0-5 ℃, filtering, collecting filtrate, concentrating the filtrate at 60-70 ℃ until no fraction is evaporated, then rectifying the filtrate at 110 ℃ and 8mbar to obtain alpha-piperazine methyl dimethyl ethoxy silane, putting the alpha-piperazine methyl dimethyl ethoxy silane into 2mmol/L acetic acid aqueous solution, carrying out hydrolytic polycondensation reaction at 50-60 ℃, and distilling the mixture after 6-8 hours to obtain transparent piperazine end-capped siloxane liquid;
2) 10.0g of piperazine-terminated siloxane, 50.0g of octamethylcyclotetrasiloxane and 2mg of tetramethylammonium hydroxide react for 8-12h at 90-100 ℃, then the temperature is raised to 130-140 ℃ for reaction for 20-30min, the tetramethylammonium hydroxide is removed by thermal decomposition, and the piperazine-terminated polydimethylsiloxane is obtained by reduced pressure distillation;
3) dissolving piperazine-terminated polydimethylsiloxane into toluene, adding hydroxyethyl methacrylate, refluxing for 6-8h, and distilling to remove toluene after the reaction is finished to obtain modified silicone oil;
the method is characterized in that: piperazine terminated polydimethylsiloxane to hydroxyethyl methacrylate 6:1 by weight.
2. Use of a modified silicone oil in a process according to claim 1, characterized in that: is used for preparing the deepening agent emulsion for the polyester fabric.
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| CN110055760A (en) | 2019-07-26 |
| CN109280172B (en) | 2019-05-21 |
| CN109280172A (en) | 2019-01-29 |
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