CN1583763A - Cation, reactnig silicone coloring fixing agent and preparing method thereof - Google Patents
Cation, reactnig silicone coloring fixing agent and preparing method thereof Download PDFInfo
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Abstract
A cationic organic silicon compound of reaction type color-fixing agent, is obtained by: react hydroxy silicone oil, dimethyl dichlorosilicane, amine, siloxane, together with quaternary ammonium agent. The durable color-fixing agent is of environmental protection. It improves color-fixing effect of active dyes in difficulty for color fixing and low fastness for washing. Besides those advantages, it is helpful for softening and has bactericidal effect. It can be used in direct dye and acidic dye to increase the wet fastness in fabrics, improve wear and sunshine tolerance, less influence in colors and tones of fabrics and have brighten and strengthen fuscous.
Description
Technical Field
The invention relates to a color fixing agent and a preparation method thereof, in particular to a cationic reactive color fixing agent and a preparation method thereof.
Background
With the development of economy, the demand of people for clothes and eating houses is changing day by day. At present, people pursue clothes materials with more attention paid to comfort besides beauty. The cotton fiber gradually becomes the main material for people to wear clothes with the characteristics of comfort and beauty, so the high-quality printed and dyed cotton fiber material is increasingly favored by people.
Anionic water-soluble dyes such as direct dyes, acid dyes and the like have complete chromatograms and bright color light, but are combined with fibers only by Van der Waals force and hydrogen bonds, and most dyes have soluble groups, so that wet rubbing fastness is poor, namely, fading and staining phenomena are serious. The covalent bonds formed by the reactive dyes with the fibres are, only theoretically, fairly strong, as if there were no dye-fastness problems. However, it is virtually impossible to wash out the unreacted dye and the hydrolyzate, and this part of the dye is discolored, which is particularly serious in the case of medium and deep colors. Furthermore, covalent bonds on dyed fabrics can also break due to hydrolysis, resulting in discoloration. Therefore, the fixation treatment by using a fixing agent in dyeing is an important means for solving the wet fastness of the dyed fabric at present.
Direct dyes, acid dyes and reactive dyes containing hydrophilic groups (sulfonic acid or carboxylic acid salts) dissociate to sodium cations and dye anions upon dissolution in water. The currently adopted cationic color fixing agent has greater reactivity to dye anions, so that dye molecules on a dyed object are enlarged, and hydrophilic groups are sealed on a fabric to form insoluble dye salt precipitates:
insoluble salt of water-soluble dye ammonium salt fixing agent
Thus, the dye can be prevented from falling off from the fabric and hydrolyzing due to ionization, thereby improving the color fastness. However, the effect of such dye fixatives on improving the "wet rubbing" of dyed materials is not obvious, i.e., when the dyed materials are washed with water, soaped, and subjected to acid-base or sweat stain, the bond between the dye molecules and the fibers is easily broken, and the dye molecules fall off from the fibers and enter into aqueous solution, so that the dyed materials are faded and stained, which can also be interpreted as poor wet fastness.
Since world war II, various color fixing agents have been invented and applied, and four types of color fixing agents mainly comprise cationic surfactant type color fixing agents, quaternary ammonium salt type color fixing agents without surface activity, resin type color fixing agents, reaction type color fixing agents and the like. Meanwhile, a series of researches are carried out on the application conditions and the effects of various color fixing agents; the cationic surfactant type color fixing agent has a good color fixing effect under most conditions, but is not soaping resistant and can reduce the original light fastness of the dye; the quaternary ammonium salt type color fixing agent without surface activity can improve the color fastness, especially the washing fastness, has little influence on the color and luster of dyed objects and the light fastness, but has certain influence on the strength of fabrics and has little influence on the soaping fastness; the resin type color fixing agent is widely applied to direct dyes, but has certain defects, for example, the color fixing agent Y has influence on the color light of the fabric after being used and contains formaldehyde, copper salt is required to be added to prevent the reduction of the light fastness when the color fixing agent M is used, but has great influence on the color light of the fabric, and particularly, when iron ions are encountered, some resin type color fixing agents have the defects of poor hot water fastness and the like; the reactive color fixing agent is a novel color fixing agent (Wen level, printing and dyeing auxiliary agent, 2000, Vol17, No6, 32-33; Zhu nationality, guan Yong Hua, the academy of south Tong industry, 16(2), 2000, 06, 28-32) which is developed recently, has better color fixing effect, has the biggest advantage of improving the wet processing fastness of dye, has less influence on the color, and has the defects of easy color change of the color fixing agent such as NF1, and the development of the color fixing agent is still in further exploration at present.
Disclosure of Invention
One of the purposes of the invention is to disclose a formaldehyde-free cationic reactive organosilicon color fixing agent which has good color fixing effect and does not influence the color and luster of fabrics and the light fastness, and overcome the defects of the existing cationic color fixing agent;
the second purpose of the invention is that: provides a preparation method of the cationic color fixing agent.
The invention outlines:
the cationic, reactive organosilicon fixing agents disclosed in the present invention contain organosilicon groups (i.e., siloxanes) that can react with the hydroxyl groups on the fiber:
fiber aftercolor fixation of organic silicon color fixing agent fiber
And a covalent bond is generated, so that the dye is firmly connected to the fiber and cannot be influenced by acid and alkali, the wet treatment fastness, the light fastness and the rubbing fastness are greatly improved, the color is not stained and faded, and the effect of permanent color fixation is achieved.
In addition, the color fixing agent is a long-chain quaternary ammonium salt compound, has a good softening effect, can resist static electricity, and can improve the tearing strength of fabrics; meanwhile, the bactericide is an organosilicon quaternary ammonium salt bactericide, attracts bacterial cell walls with negative charges, and the long chain contacts the other side of the bacterial cell walls, so that the negative charges attracted by cations are reduced, and then the cell walls are cracked, and dissolved substances are exuded to die.
The technical scheme is as follows:
the cation and reaction type organosilicon color fixing agent is a compound with a structure shown in a formula (1):
in the formula: n is 0-20, and m is 1-12; r is: - (CH)2)aSi(R1)3；-CH2CH＝CH2；-CH2R2Ar；CkH2k+1Cl or-CH2R3N+(CH3)3·Cl-；
Wherein: a is 1-15; k is 1-30, preferably k is 8-18; r1Is alkyl or alkoxy, preferably R1Is C1～C8Alkyl or alkoxy of (2), more preferably C1～C4Alkyl or alkoxy of (2), preferably CH3；OCH3；C2H5Or OC2H5；R2Is (CH)2)bB is 0 to 10, preferably b is 0; r3Is (CH)2)dThe alkyl chain of (1) preferably has d of 0 to 30, more preferably d of 7 to 17.
The method for preparing the cationic color fixing agent comprises the following steps:
the preparation reaction equation is as follows:
the meanings of n, m and R in the equation are the same as described above.
(1) Adding hydroxyl silicone oil [ compound (2)]and dimethyldichlorosilane [ compound (3)]into a reactor according to the proportion (molar ratio) of 1: 2, heating to 40-150 ℃, and reacting for 10-90 minutes to obtain a compound (4), wherein the optimal reaction temperature is 60-100 ℃, and the optimal reaction time is 20-60 minutes;
(2) reacting the compound (4) with an organic amine [ NH]2((CH2)2NH)mH]Adding the mixture into a reactor according to the ratio (molar ratio) of 1: 4, reacting at 20-80 ℃ and preferably 30-60 ℃ until white smoke disappears, heating to dissociate and extract generated HCl, wherein the heating temperature is based on HCl dissociation, and the reaction time is based on HCl complete dissociation to prepare a compound (5);
(3) adding the compound (5) and a quaternizing agent (alkyl halide, preferably alkyl chloride) into a reactor at a molar ratio of 1: 0.5-1.5, preferably at a molar ratio of 1: 1-1.2, and reacting at 80-150 ℃ to obtain the target compound (1), wherein the recommended reaction temperature is 80-120 ℃.
The invention has the innovation that the organosilicon quaternary ammonium salt cation is used for fixing the color of the anionic dye, has the characteristic of permanent color fixation compared with other color fixing agent products, and simultaneously integrates softness and sterilization; and the raw materials are easy to obtain and cheap, the synthesis process is simple, the reaction condition is mild, the method is simple and easy to implement, the yield is high, and the industrial production is easy to realize. The product is a formaldehyde-free green environment-friendly color fixing agent, has good color fixing effect on anionic dyes (direct dyes, acid dyes and reactive dyes), improves the wet treatment fastness, the rubbing fastness, the light fastness, the perspiration fastness, the acid and alkali resistance and does not influence the color of fabrics.
Compared with the prior color fixing agent, the application method of the color fixing agent of the invention comprises the following steps: except that the dosage of the color fixing agent is different (the dosage of the color fixing agent of the invention is 30-50 wt% less than that of the existing color fixing agent, thus achieving the color fixing effect of the existing color fixing agent), the rest are the same.
The specific implementation mode is as follows:
the invention is further illustrated by the following examples, which are intended to provide a better understanding of the contents of the invention. The examples given therefore do not limit the scope of protection of the invention:
example 1
The structure of the synthesized color fixing agent is as follows:
wherein R is-CH2CH2CH2Si(OCH3)3
1. Synthesizing chlorine-containing silicone oil:
0.10mol of hydroxy silicone oil (n is 4) is added into a three-neck flask, 0.20mol of dimethyldichlorosilane is added into a dropping funnel, stirring is carried out at 40 ℃, dimethyldichlorosilane is slowly added, at the moment, the liquid in the three-neck flask can be observed to bubble, a large amount of HCl white gas is generated in the reaction, and the gas is pumped out to prepare colorless or light yellow liquid.
2. Reaction of the chlorosilicone oil with the amine:
adding 0.04mol of triethylene tetramine (m is 2) into a three-neck flask, stirring at room temperature, dropwise adding 0.01mol of chlorine-containing silicone oil (n is 4) by using a dropping funnel, generating white fog in the flask, generating a large amount of white salt, gradually disappearing the white fog after a period of time due to the action of excessive amine and HCl, then heating, melting the white salt, dissociating the HCl, decompressing and exhausting until no white fog exists in the flask, standing, layering the system, taking the upper layer of transparent light yellow liquid as an organic silicon amine compound, and hermetically storing.
3. And (3) synthesis of a color fixing agent:
adding 100ml of methanol and 0.01mol of organic silicon amine compound into a three-neck flask, stirring at room temperature, slowly dropwise adding 0.18mol of siloxane (a is 3) by using a dropping funnel, heating to react at 80 ℃ after completion, and completely reacting after 5 hours to obtain the product which is the color fixing agent.
IR(KBr)：ν-Si-O-＝1064.5cm-1(S)，ν-Si-C-＝829.8cm-1(S)。
Example 2
The structure of the synthesized color fixing agent is as follows:
in the formula: R-CH2CH2CH2CH2CH2Si(CH3)3
1. Synthesizing chlorine-containing silicone oil:
0.10mol of hydroxy silicone oil (n is 6) is added into a three-neck flask, 0.20mol of dimethyldichlorosilane is added into a dropping funnel, stirring is carried out at 150 ℃, dimethyldichlorosilane is slowly added, at the moment, the liquid in the three-neck flask can be observed to bubble, a large amount of HCl white gas is generated in the reaction, and the gas is pumped out to prepare colorless or light yellow liquid.
2. Reaction of chlorosilicone oils with amines
0.04mol of triethylene tetramine (m is 3) is added into a three-neck flask, stirring is carried out at room temperature, 0.01mol of chlorine-containing silicone oil is dripped into a dropping funnel, white fog is generated in the flask and is accompanied by generation of a large amount of white salt, the white fog disappears gradually after a period of time due to action of excessive amine and HCl, then heating is carried out, the white salt is melted firstly, then HCl is dissociated, reduced pressure is pumped until no white smoke exists in the flask, the mixture is layered after standing, the transparent light yellow liquid on the upper layer is an organic silicon amine compound, and the mixture is hermetically stored.
3. Synthesis of fixing agent
Adding 100ml of ethanol and 0.01mol of organic silicon amine compound into a three-neck flask, stirring at room temperature, slowly dropwise adding 0.14mol of silane (a is 5) by using a dropping funnel, heating to react at 150 ℃ after the completion of the reaction, and completelyreacting after 5 hours to obtain the product which is the color fixing agent.
IR(KBr)：ν-Si-O-＝1058.5cm-1(S)，ν-Si-C-＝825.8cm-1(S)，ν-Si(CH3)3-＝840.5cm-1、756.0cm-1(S)。
Example 3
The structure of the synthesized color fixing agent is as follows:
in the formula: r is-CH2CH2CH2Si(OC2H5)3
1. Synthesizing chlorine-containing silicone oil:
30ml of ethanol and 0.10mol of hydroxy silicone oil (n is 8) are added into a three-neck flask, 0.20mol of dimethyldichlorosilane is added into a dropping funnel, the mixture is stirred at 80 ℃, dimethyldichlorosilane is slowly added in a gradual manner, a large amount of HCl white gas is generated in the reaction, and the gas is pumped out to prepare colorless or pale yellow viscous liquid.
2. Reaction of chlorosilicone oils with amines
Adding 50ml ethanol into a three-neck flask, stirring at room temperature, introducing ammonia gas (m is 0), simultaneously dropwise adding 0.01mol of chlorine-containing silicone oil by using a dropping funnel, wherein white fog is generated in the flask and accompanied by generation of a small amount of white salt, the white fog gradually disappears after a period of time due to action of excessive amine and HCl, then heating, melting the white salt, dissociating the HCl, decompressing and exhausting until no white smoke exists in the flask, standing, layering the system, and hermetically storing the upper layer of transparent yellow liquid which is an organic silicon amine compound.
3.And (3) synthesis of a color fixing agent:
adding 100ml of isopropanol and 0.01mol of organic silicon amine compound into a three-neck flask, stirring at room temperature, slowly dropwise adding 0.06mol of siloxane (a is 3) by using a dropping funnel, heating to react at 100 ℃ after the completion of the reaction, and completely reacting after 5 hours to obtain the product which is the color fixing agent.
IR(KBr)：ν-Si-O-＝1070.0cm-1(S)，ν-Si-C-＝836.5cm-1(S)。
Example 4
Wherein R: -CH2CH＝CH2
1. Synthesizing chlorine-containing silicone oil:
0.10mol of hydroxy silicone oil (n is 4) is added into a three-neck flask, 0.20mol of dimethyldichlorosilane is added into a dropping funnel, stirring is carried out at 40 ℃, dimethyldichlorosilane is slowly added, at the moment, the liquid in the three-neck flask can be observed to bubble, a large amount of HCl white gas is generated in the reaction, and the gas is pumped out to prepare colorless or light yellow liquid.
2. Reaction of the chlorosilicone oil with the amine:
adding 0.04mol of triethylene tetramine (m is 2) into a three-neck flask, stirring at room temperature, dropwise adding 0.01mol of chlorine-containing silicone oil (n is 4) by using a dropping funnel, generating white fog in the flask, generating a large amount of white salt, gradually disappearing the white fog after a period of time due to the action of excessive amine and HCl, then heating, melting the white salt, dissociating the HCl, decompressing and exhausting until no white fog exists in the flask, standing, layering the system, taking the upper layer of transparent light yellow liquid as an organic silicon amine compound, and hermetically storing.
3. And (3) synthesis of a color fixing agent:
adding 100ml of methanol and 0.01mol of organic silicon amine compound into a three-neck flask, stirring at room temperature, slowly dropwise adding 0.18mol of allyl chloride by using a dropping funnel, heating to react at 80 ℃ after completion, and completely reacting after 5 hours to obtain the product which is the color fixing agent.
IR(KBr)：ν-Si-O-＝1060.5cm-1(S)，ν-Si-C-＝832.8cm-1(S)。
Example 5
The structure of the synthesized color fixing agent is as follows:
in the formula: r is-CH2Ar
1. Synthesizing chlorine-containing silicone oil:
0.10mol of hydroxy silicone oil (n is 6) is added into a three-neck flask, 0.20mol of dimethyldichlorosilane is added into a dropping funnel, stirring is carried out at 150 ℃, dimethyldichlorosilane is slowly added, at the moment, the liquid in the three-neck flask can be observed to bubble, a large amount of HCl white gas is generated in the reaction, and the gas is pumped out to prepare colorless or light yellow liquid.
3. Reaction of chlorosilicone oils with amines
0.04mol of triethylene tetramine (m is 3) is added into a three-neck flask, stirring is carried out at room temperature, 0.01mol of chlorine-containing silicone oil is dripped into a dropping funnel, white fog is generated in the flask and is accompanied by generation of a large amount of white salt, the white fog disappears gradually after a period of time due to action ofexcessive amine and HCl, then heating is carried out, the white salt is melted firstly, then HCl is dissociated, reduced pressure is pumped until no white smoke exists in the flask, the mixture is layered after standing, the transparent light yellow liquid on the upper layer is an organic silicon amine compound, and the mixture is hermetically stored.
3. Synthesis of fixing agent
Adding 100ml of ethanol and 0.01mol of organic silicon amine compound into a three-neck flask, stirring at room temperature, slowly dropwise adding 0.14mol of benzyl chloride by using a dropping funnel, heating to react at 120 ℃ after the completion of the reaction, and completely reacting after 5 hours to obtain the product which is the color fixing agent.
IR(KBr)：ν-Si-O-＝1068.5cm-1(S)，ν-Si-C-＝835.8cm-1(S)。
Example 6
The structure of the synthesized color fixing agent is as follows:
in the formula: r is-C12H25N+(CH3)3·Cl-
1. Synthesizing chlorine-containing silicone oil:
30ml of ethanol and 0.10mol of hydroxy silicone oil (n is 8) are added into a three-neck flask, 0.20mol of dimethyldichlorosilane is added into a dropping funnel, the mixture is stirred at 80 ℃, dimethyldichlorosilane is slowly added in a gradual manner, a large amount of HCl white gas is generated in the reaction, and the gas is pumped out to prepare colorless or pale yellow viscous liquid.
4. Reaction of chlorosilicone oils with amines
Adding 50ml ethanol into a three-neck flask, stirring at room temperature, introducing ammonia gas (m is 0), simultaneously dropwise adding 0.01mol of chlorine-containing silicone oil by using a dropping funnel, wherein white fog is generated in the flask and accompanied by generation of a small amount of white salt, the white fog gradually disappears after a period of time due to action of excessive amine and HCl, then heating, melting the white salt, dissociating the HCl, decompressing and exhausting until no white smoke exists in the flask, standing, layering the system, and hermetically storing the upper layer of transparent yellow liquid which is an organic silicon amine compound.
5. And (3) synthesis of a color fixing agent:
adding 100ml of isopropanol and 0.01mol of organic silicon amine compound into a three-neck flask, stirring at room temperature, dissolving 0.06mol of end group chlorododecyl quaternary ammonium salt by using 20ml of isopropanol, slowly dropwise adding by using a dropping funnel, heating to react at 130 ℃ after completion of the reaction, and completely reacting after 5 hours to obtain the product which is the color fixing agent.
IR(KBr)：ν-Si-O-＝1066.0cm-1(S)，ν-Si-C-＝830.5cm-1(S)。
Example 7
The application contrast experiment of the color fixing agent of the invention and the prior color fixing agent is as follows:
and (3) color fixing conditions: temperature: 30-80 ℃; bath ratio: 1: 15-50; and (3) fixation time: 15-60 minutes, and the experimental results are shown in the following table:
| color fixing agent | Appearance of the product | Does not swing Hair article Dissolving in water Property of (2) | Stabilization Property of (2) | Color fixation test | |||||
| Fastness to soaping | Fastness to rubbing | Fastness to perspiration | |||||||
| Color fading (grade) | Wet rubbing device (grade) | Staining (grade) | Color fading (grade) | Staining (grade) | Dry massage (grade) | ||||
| The product of example 1 | Light yellow liquid | Good effect | Is preferably used | 4-5 | 3-5 | 3～5 | 3-5 | 3-5 | 4-5 |
| The product of example 2 | Light yellow liquid | Good effect | Is preferably used | 4-5 | 3-4 | 3-5 | 3-4 | 3-5 | 4-5 |
| The product of example 3 | Yellow liquid | Good effect | Is preferably used | 4-5 | 3-5 | 4 | 3-5 | 2-3 | 3-4 |
| The product of example 4 | Light yellow liquid | Good effect | Is preferably used | 4-5 | 3-5 | 4 | 4 | 3-5 | 3-5 |
| The product of example 5 | Yellow liquid | Good effect | Is preferably used | 4-5 | 4-5 | 4-5 | 3-5 | 3-4 | 4 |
| The product of example 6 | Yellow liquid | Good effect | Is preferably used | 4-5 | 3-5 | 3-5 | 4 | 3 | 3-5 |
| 1631 | White sticky matter | Is preferably used | Good effect | 1-3 | 1-3 | 3 | 2 | 1-3 | 1-3 |
| Dye-fixing agent Y (dicyandiamide) Polymers with formaldehyde) | Colorless transparent liquid | Good effect | Good effect | 2-3 | 2-4 | 2 | 2-3 | 2-3 | 2-3 |
| Quaternary ammonium salts of organosilicon | White liquid | Is poor | Is preferably used | 2-3 | 2-4 | 2-3 | 2-3 | 2 | 3-4 |
| Colour fixing agent ED-Z (Tree) Fat reaction type color fixing agent | Brown liquid | Is poor | Good effect | 2-3 | 3 | 2-3 | 2-3 | 3-4 | 2-3 |
| Fixing agent GS501 (containing Polymers of quaternary ammonium salts) | Brown liquid | Is preferably used | Good effect | 2-4 | 2-4 | 3-4 | 3 | 2-3 | 2-3 |
Claims (13)
1. A cationic, reactive silicone fixing agent which is a compound having the structure shown in formula (1):
in the formula: n is 0-20, and m is 1-12; r is: - (CH)2)aSi(R1)3；-CH2CH＝CH2；-CH2R2Ar；CkH2k+1Cl or-CH2R3N+(CH3)3·Cl-；
Wherein: a is 1-15; k is 1 to 30, R1Is alkyl or alkoxy, R2Is (CH)2)bB is 0 to 10, R3Is (CH)2)dAnd d is 0 to 30.
2. The fixing agent as claimed in claim 1, wherein R is1Is C1～C8Alkyl or alkoxy groups of (a).
3. The fixing agent as claimed in claim 2, wherein R is1Is C1～C4Alkyl or alkoxy groups of (a).
4. The fixing agent as claimed in claim 3, wherein R is1Is CH3；OCH3；C2H5Or OC2H5。
5. The fixing agent of claim 1, wherein R is CkH2k+1Cl，k＝8～18。
6. The dye-fixing agent of claim 1, wherein R is-CH2Ar。
7. The dye-fixing agent of claim 1, wherein R is-CH2R3N+(CH3)3·Cl-In the formula, R3Is (CH)2)d，d＝7～17。
8. A process for the preparation of a fixing agent according to any of claims 1 to 7, characterized in that it comprises the following steps:
(1) adding the compound (2) and the compound (3) in a molar ratio of 1: 2 into a reactor at 40 ℃
Reacting for 10-90 minutes at 150 ℃ to obtain a compound (4);
(2) reacting the compound (4) with an organic amine [ NH]2((CH2)2NH)mH]Is added into the reaction in a molar ratio of 1: 4
Reacting in an reactor at 20-80 ℃ until white smoke disappears, and then heating to dissociate generated HCl and pumping
Heating temperature is based on HCl dissociation, reaction time is based on HCl complete dissociation, and the compound is prepared
(5)；
(3) Adding the compound (5) and a quaternizing agent into a reactor according to the molar ratio of 1: 0.5-1.5
Reacting at 80-150 ℃ to obtain a target compound (1);
the preparation reaction equation is as follows:
9. the process according to claim 8, wherein the reaction temperature in the step (!) is 60 ℃ to 100 ℃ and the reaction time is 20 to 60 minutes.
10. The process according to claim 8, wherein the compound (4) is reacted with an organic amine [ NH]2((CH2)2NH)mH]The reaction temperature is 30-60 ℃.
11. The process according to claim 8, wherein the molar ratio of the compound (5) to the quaternizing agent is 1: 1 to 1.2, and the reaction temperature is 80 ℃ to 120 ℃.
12. The process according to claim 9, wherein the compound (4) is reacted with an organic amine [ NH]2((CH2)2NH)mH]The reaction temperature is 30-60 ℃.
13. The process according to claim 12, wherein the molar ratio of the compound (5) to the quaternizing agent is 1: 1 to 1.2, and the reaction temperature is 80 ℃ to 120 ℃.
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| CN104927064A (en) * | 2015-05-28 | 2015-09-23 | 齐鲁工业大学 | Preparation method for polymeric dye based on hyperbranched polyamine-ester |
| CN104927064B (en) * | 2015-05-28 | 2017-06-23 | 齐鲁工业大学 | A kind of preparation method of the high molecular dye based on hyperbranched polyurethane |
| CN105622944A (en) * | 2016-03-30 | 2016-06-01 | 科凯精细化工（上海）有限公司 | Quaternized organic silicone oil and preparation method thereof |
| CN105622945A (en) * | 2016-03-30 | 2016-06-01 | 科凯精细化工（上海）有限公司 | Darkening finishing agent and preparation method thereof |
| CN105622944B (en) * | 2016-03-30 | 2018-08-07 | 科凯精细化工（上海）有限公司 | A kind of quaternized organic silicone oil and preparation method thereof |
| CN105622945B (en) * | 2016-03-30 | 2018-09-14 | 科凯精细化工（上海）有限公司 | Deep finishing agent of a kind of increasing and preparation method thereof |
| CN108660813A (en) * | 2018-07-07 | 2018-10-16 | 曾文华 | A kind of formaldehyde-free color fixing agent and preparation method thereof |
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