CN110527052A - A kind of polyurethane-modified Organosiliconcopolymere containing quaternary ammonium salt - Google Patents
A kind of polyurethane-modified Organosiliconcopolymere containing quaternary ammonium salt Download PDFInfo
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- CN110527052A CN110527052A CN201910855402.2A CN201910855402A CN110527052A CN 110527052 A CN110527052 A CN 110527052A CN 201910855402 A CN201910855402 A CN 201910855402A CN 110527052 A CN110527052 A CN 110527052A
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- quaternary ammonium
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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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4833—Polyethers containing oxyethylene units
- C08G18/4837—Polyethers containing oxyethylene units and other oxyalkylene units
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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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/50—Polyethers having heteroatoms other than oxygen
- C08G18/5021—Polyethers having heteroatoms other than oxygen having nitrogen
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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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/61—Polysiloxanes
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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
- 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
- D06M15/564—Polyureas, polyurethanes or other polymers having ureide or urethane links; Precondensation products forming them
- D06M15/568—Reaction products of isocyanates with polyethers
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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
- D06M16/00—Biochemical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. enzymatic
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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
- D06M2101/02—Natural fibres, other than mineral fibres
- D06M2101/04—Vegetal fibres
- D06M2101/06—Vegetal fibres cellulosic
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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
- D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
- D06M2200/50—Modified hand or grip properties; Softening compositions
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- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
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- Engineering & Computer Science (AREA)
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- Life Sciences & Earth Sciences (AREA)
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- Silicon Polymers (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
The present invention provides a kind of polyurethane-modified Organosiliconcopolymeres containing quaternary ammonium salt, epoxy terminated polysiloxanes is reacted with the compound containing tertiary amine group, obtain the silicone oil containing quaternized structure, then diisocyanate is added and containing step-reaction polymerization is carried out with the polyethers of isocyanate-reactive groups, obtains the polyurethane-modified Organosiliconcopolymere containing quaternary ammonium salt.The polyurethane-modified Organosiliconcopolymere containing quaternary ammonium salt of the invention, compared to Siloxane-Oxyalkylene Copolymers in original technology, due to containing quaternized structure in main chain, not only greatly improve the hydrophily of copolymer, and it can assign that soft fabric, moisture absorption be antistatic and the functions such as antibacterial, existing amino silicone class can be effectively improved to arrange, the most importantly quaternizing agent without the severe toxicity such as additional such as dimethyl suflfate, it can be obtained the polyurethane-modified Organosiliconcopolymere containing quaternized structure, technique is relatively simple, and operating condition is easily controllable.
Description
Technical field
The invention belongs to the fields of textile finish, and in particular to one kind is containing the polyurethane-modified organosilicon copolymerization of quaternary ammonium salt
Object.
Background technique
Dimethyl silicone polymer is a kind of very superior fabric softener of performance, due to its good molecular flexibility and
Methyl content abundant can to form methyl coating in fiber surface, to reduce the sound friction system between fiber
Number, reaches good soft effect.But since it does not firmly form binding force with fiber, simply by a limited number of models
De Huali and hydrogen bond are in conjunction with fiber, simultaneously as intramolecular does not have crosslinkable group so can not be individually in fiber surface
Film forming, fastness are poor.In order to solve these problems, it has been developed that the organosilicon product of many improvement, wherein with amino silicone
Oil is representative, and due to the presence of amino, under mildly acidic conditions, amino can be cationized, and generation can be with negative electricity on fiber
Lotus group forms the relatively firm bonding that electrostatic attraction combines, and fastness is due to common silicone oil, and due to this electrostatic attraction
Effect, such that have more methyl external, therefore such product has the effect of super softness, be flexibility currently on the market
The best organosilicon product of energy.But amino silicone the shortcomings that also having it, since the nitrogen-atoms cloud density in amino is higher, institute
To be easy and absorb photoelectron that photochemical reaction occurs, to generate so-called Yellowing, and amido silicon oil is also not easy
Emulsification is easy the disadvantage that demulsification forms the hydrophilies differences such as oil mark on the fabric.Product more advanced at present is that ternary polymerization has
Machine silicon is embedded in the amino-polyether segment of good hydrophilic property by block copolymerization in organosilicon product, utilize the recessiveness sun of amino
The hydrophily of ion characteristic and polyethers solves the above problems.But its synthesis process it is more complicated, crucial raw material rely on into
Mouthful, especially in silicon hydrogen and allyl glycidyl ether addition process cannot 100% conversion, lead to block silicone oil in the market
Unstable quality, it is at high cost, while selectable amine terminated polyether type is limited, amine terminated polyether biggish for molecular weight needs
The solvent wanted is big, leads to the effect that amido silicon oil can not be embodied in application process.
Polyurethane-modified organosilicon can overcome the macromolecule of single variety in conjunction with the advantages of polyurethane and organosilicon
The shortcomings that object, the excellent properties with polyurethane while retaining silicone softening agent improved flexibility.Patent
CN20160826047.2 discloses a kind of preparation method of polysiloxane-polyurethane copolymer fabric softener that feel is excellent.Though
The flexibility of amido silicon oil, resilience are so remained, and there is certain hydrophily, vividness and whiteness, but its is smooth
It still can not meet the demand in market with hydrophily.
Summary of the invention
The purpose of the present invention is to provide a kind of polyurethane-modified Organosiliconcopolymeres containing quaternary ammonium salt, to further increase
The hydrophilic and smooth performance of polyurethane-modified Organosiliconcopolymere.
The purpose of the invention is achieved by the following technical solution:
Firstly, epoxy terminated polysiloxanes is reacted with the compound containing tertiary amine group, diisocyanate is then added
Ester, polyether polyol or polyetheramine carry out step-reaction polymerization, obtain the polyurethane-modified Organosiliconcopolymere containing quaternary ammonium salt.
The preparation method of the polyurethane-modified Organosiliconcopolymere containing quaternary ammonium salt, the specific steps are as follows:
1) blender is being housed, thermometer, reflux condensing tube and nitrogen are blown into four mouthfuls of reaction units of pipe and are added 100
The epoxy terminated polysiloxanes of part adds containing tertiary amine compounds and neutralizes agent composition, is stirred to react 3-8 in 60-100 DEG C
Hour, obtain the polysiloxanes containing quaternary ammonium salt；
Wherein,
In step (1), the epoxy terminated polysiloxanes has the general structure as shown in following formula (I):
Wherein, in formula (I), n be 25~400 natural number；
In step (1), described has general structure shown in following (II) containing tertiary amine compounds:
Wherein, in formula (II), m be 1~20 natural number；R1For alkyl chain, carbon number is 1~3；R2For CH3, or-NH2,
Or-OH；R3For alkyl chain or branched alkyl chain, carbon number is 1~20, and dosage is the 50-110% of epoxy silicon oil molal quantity.
In step (1), the neutralizer is selected from one of formic acid, acetic acid, propionic acid, lauric acid, is three-level amine compounds
The 90%-110% of object molal quantity.
2) 1-50 parts of diisocyanate, 30-100 parts of solvents are added in quaternary ammonium salt polysiloxanes among the above, in 25-80
It DEG C is stirred to react 1-6 hours, analyzes residual NCO content with di-n-butylamine method, 10-50 part polyether Glycols are then added or gather
Ether amines and catalyst react 5-12 hours in 65-100 DEG C of holding, obtain the polyurethane-modified Organosiliconcopolymere containing quaternary ammonium salt；
Wherein,
In step (2), the diisocyanate is selected from isofoer diisocyanate (IPDI), hexamethylene diisocyanate
(HDI), ditolyl methane diisocyanate (MDI), sub- xylylene diisocyanate (XDI) or toluene di-isocyanate(TDI)
Or no less than two kinds of combination one of (TDI)；
In step (2), the solvent is acetone, methyl butyl ketone, butanone, glycol dimethyl ether, diethylene glycol dimethyl ether, second
One of dibutyl ether, dibutyl ethylene glycol ether, Propylene Glycol Dimethyl Ether, dimethyl ether；
In step (2), the catalyst is one in organotin catalysts, organozinc catalyst and organic bismuth catalyst
Kind, wherein preferred organotin catalysts are dibutyltin dilaurate, dosage is quaternary ammonium salt polysiloxanes, diisocyanate
With the 0.1-0.5% of polyethers gross mass；
In step (2), the polyether polyol is polyethylene glycol, polypropylene glycol or both copolymerization and poly- tetrahydro furan
It mutters one of ether glycol or no less than two kinds of combination, molecular weight 300-6000；
In step (2), the polyetheramine is the polyethers of primary amine sealing end, has general structure shown in following (III):
Wherein, in formula (III), x+y+z be 1~70 natural number.
A kind of polyurethane-modified Organosiliconcopolymere containing quaternary ammonium salt, according to obtained by above-mentioned preparation method.
Compared with prior art, the present invention having the following advantages that and effect:
(1) preparation method of the polyurethane-modified Organosiliconcopolymere of the invention containing quaternary ammonium salt, technique is relatively simple, operation
Condition is easily controllable, it is most important that without the quaternizing agent of the severe toxicity such as additional such as dimethyl suflfate, can be obtained containing season
The polyurethane-modified Organosiliconcopolymere of ammonium structure.
(2) contain quaternized structure in polyurethane-modified Organosiliconcopolymere main chain of the invention, not only greatly improve altogether
The hydrophily of polymers, and can assign that soft fabric, moisture absorption be antistatic and the functions such as antibacterial, existing amino silicone can be effectively improved
Class arranges.
Detailed description of the invention
Fig. 1 is the infrared spectrum of the polyurethane-modified Organosiliconcopolymere containing quaternized structure in embodiment 1；
Specific embodiment
Present invention will now be described in further detail with reference to the embodiments and the accompanying drawings, but embodiments of the present invention are unlimited
In this.
Embodiment 1
The end 100g epoxy silicon oil (molecular weight 12000, m ≈ 159) is added to four equipped with thermometer and reflux condensing tube
In mouth flask, under agitation, 1.2g N, N- dimethyl amine and acetic acid 1g is added, is stirred to react 5 hours, obtains in 90 DEG C
To the polysiloxanes containing quaternary ammonium salt；Then, isophorone diisocyanate 3.5g, solvent acetone 30g is added, it is anti-in 50 DEG C of stirrings
It answers 1 hour, analyzes residual NCO content with di-n-butylamine method, wait after reaching calculated value, add 30g polyether Glycols PEG-
PPG2000 (molecular weight 2000, EO/PO=), catalyst dibutyltin dilaurate 0.1g, 65 DEG C are stirred to react 5 hours, obtain
To the polyurethane-modified Organosiliconcopolymere containing quaternary ammonium salt.
As can be seen that 800cm from attached drawing 1-1And 1261cm-1The absorption peak of appearance should belong to Si-O-Si in silicone oil structure
With the characteristic absorption peak of Si-C.In 2280-2240cm-1The NCO characteristic absorption peak not occurred in range shows the copolymerization of preparation
Exist in object without free CNO.In 1530cm-1The peak of appearance should be the deformation vibration the absworption peak of N-H group in CO-NH, In
1698cm-1The peak of appearance should be the stretching vibration peak of C=O group in CO-NH, and the above two o'clock is that the feature of carbamate groups is shaken
Dynamic peak shows surveyed substance containing polyurethane structural, and in addition from the point of view of absorption peak strength, content is relatively low, feeds intake with experiment
What ratio was consistent with.1097cm-1And 1032cm-12 peaks occurred should be that the asymmetric stretch vibration of C-O-C in polyethers is inhaled
Peak is received, illustrates that there are polyether components in the copolymer.
Embodiment 2
The end 100g epoxy silicon oil (molecular weight 15000, m ≈) is added to four mouthfuls of burnings equipped with thermometer and reflux condensing tube
In bottle, under agitation, 1.0g N, N- dimethylethanolamine and malonic acid 1.2g is added, is stirred to react in 100 DEG C 3 hours,
Obtain the polysiloxanes containing quaternary ammonium salt；Then, aminomethyl phenyl diisocyanate 4.6g, solvent acetic acid propyl ester 80g, at 50 DEG C is added
It is stirred to react 2 hours, analyzes residual NCO content with di-n-butylamine method, wait after reaching calculated value, add 10g hydroxy polyethers amine
PEG400 (molecular weight 400, a=9, b=0), catalyst dibutyltin dilaurate 0.1g, 80 DEG C are stirred to react 8 hours, obtain
To the polyurethane-modified Organosiliconcopolymere containing quaternary ammonium salt.
Embodiment 3
The end 100g epoxy silicon oil (molecular weight 30000, m ≈) is added to four mouthfuls of burnings equipped with thermometer and reflux condensing tube
In bottle, under agitation, 1g N, N- dimethyl-ethylenediamine and lauric acid 2g is added, is stirred to react 8 hours, obtains in 100 DEG C
Polysiloxanes containing quaternary ammonium salt；Then, six hexyl diisocyanate 2.4g, solvent dimethyl ether 100g, 25 are added
It DEG C is stirred to react 3 hours, analyzes residual NCO content with di-n-butylamine method, wait after reaching calculated value, add 20g hydroxy polyethers
PEG-PPG100 (molecular weight 1000, a=12, b=8), catalyst dibutyltin dilaurate 0.5g, 100 DEG C are stirred to react
12 hours, obtain the polyurethane-modified Organosiliconcopolymere containing quaternary ammonium salt.
Embodiment 4
The end 100g epoxy silicon oil (molecular weight 2000, m ≈) is added to four mouthfuls of burnings equipped with thermometer and reflux condensing tube
In bottle, under agitation, 8g N, N- diethyl ethylenediamine and acetic acid 6g is added, is stirred to react 5 hours, is contained in 60 DEG C
The polysiloxanes of quaternary ammonium salt；Then, methyl diphenylene diisocyanate 50g, solvent dibutyl ethylene glycol ether 30g, 25 is added
It DEG C is stirred to react 3 hours, analyzes residual NCO content with di-n-butylamine method, wait after reaching calculated value, add 35g polyetheramine
D400 (molecular weight 400, x+z=6, y=0), 80 DEG C are stirred to react 6 hours, obtain total containing the polyurethane-modified organosilicon of quaternary ammonium salt
Polymers.
Embodiment 5
The end 100g epoxy silicon oil (molecular weight 8000, m ≈) is added to four mouthfuls of burnings equipped with thermometer and reflux condensing tube
In bottle, under agitation, 20g N, N- dimethyl lauryl amine and acetic acid 6g is added, is stirred to react 5 hours, is contained in 90 DEG C
The polysiloxanes of quaternary ammonium salt；Then, isophorone diisocyanate 10g, solvent acetone 30g is added, it is small to be stirred to react 6 at 80 DEG C
When, with di-n-butylamine method analyze residual NCO content, wait after reaching calculated value, add 50g polyetheramine ED900 (molecular weight 900,
X+z=6, y=12.5), 75 DEG C are stirred to react 8 hours, obtain the polyurethane-modified Organosiliconcopolymere containing quaternary ammonium salt.
Comparative example
The end 100g epoxy silicon oil (molecular weight 12000, m ≈) is added to four mouthfuls of burnings equipped with thermometer and reflux condensing tube
In bottle, 30g ED2003 and solvent isopropanol 100g is added, is stirred to react in 85 DEG C 24 hours, obtains the poly- silicon of polyether modified amino
Oxygen alkane.
Application Example
The above silicone oil: being configured to 20% aqueous solution by contrast standard, and comparing cloth specimen is that pure white is knitted cotton, and dosage is
10g/L, an immersing and rolling are dried 90 seconds in 170 DEG C of setting.
Evaluation method: the feel mainly integrated survey in terms of flexibility and flatness is touched by several experts are blind, and 5 grades are preferably,
1 grade worst.
The hydrophily of fabric passes through the timing definition that one drop water of measurement is absorbed by fabric completely in seconds.
Comparison result is as follows:
The above embodiment is a preferred embodiment of the present invention, but embodiments of the present invention are not by above-described embodiment
Limitation, other any changes, modifications, substitutions, combinations, simplifications made without departing from the spirit and principles of the present invention,
It should be equivalent substitute mode, be included within the scope of the present invention.
Claims (5)
1. a kind of polyurethane-modified Organosiliconcopolymere containing quaternary ammonium salt, which is characterized in that be made according to following steps:
1) blender, thermometer are being housed, reflux condensing tube and nitrogen are blown into 100 parts of ends of addition in four mouthfuls of reaction units of pipe
The polysiloxanes of epoxy group adds containing tertiary amine compounds and neutralizes agent composition, it is small to be stirred to react 3-8 in 60-100 DEG C
When, obtain the polysiloxanes containing quaternary ammonium salt；
2) 1-50 parts of diisocyanate, 30-100 parts of solvents are added in the obtained polysiloxanes containing quaternary ammonium salt of step 1),
It is stirred to react at 25-80 DEG C 1-6 hours, analyzes residual NCO content with di-n-butylamine method, 10-50 parts of polyethers binary are then added
Alcohol or polyetheramine and catalyst react 5-12 hours in 65-100 DEG C of holding, obtain polyurethane-modified organic containing quaternary ammonium salt
Siliceous copolymer；
In step 1), the epoxy terminated polysiloxanes has following structure general formula:
Wherein, the natural number that n is 25~400；
Described has following structure general formula containing tertiary amine compounds:
Wherein, the natural number that m is 1~20；R1For alkyl chain, carbon number is 1~3；R2For CH3, or-
NH2, or-OH；R3For alkyl chain or branched alkyl chain, carbon number is 1~20, and dosage is the 50-110% of epoxy silicon oil molal quantity；
In step 2), the diisocyanate is selected from isofoer diisocyanate (IPDI), hexamethylene diisocyanate
(HDI), ditolyl methane diisocyanate (MDI), sub- xylylene diisocyanate (XDI) or toluene di-isocyanate(TDI)
Or no less than two kinds of combination one of (TDI).
2. the polyurethane-modified Organosiliconcopolymere containing quaternary ammonium salt according to claim 1, it is characterised in that: in step 2),
The solvent is acetone, methyl butyl ketone, butanone, glycol dimethyl ether, diethylene glycol dimethyl ether, butyl cellosolve, diethyl two
One of alcohol butyl oxide, Propylene Glycol Dimethyl Ether, dimethyl ether, the catalyst are organotin catalysts, organic
One of zinc catalyst and organic bismuth catalyst.
3. the polyurethane-modified Organosiliconcopolymere containing quaternary ammonium salt according to claim 2, it is characterised in that: the organotin is urged
Agent is dibutyltin dilaurate, and dosage is the 0.1- of quaternary ammonium salt polysiloxanes, diisocyanate and polyethers gross mass
0.5%；The polyether polyol is in polyethylene glycol, polypropylene glycol or both copolymerization and polytetrahydrofuran ether glycol
A kind of or no less than two kinds of combination, molecular weight 300-6000.
4. the polyurethane-modified Organosiliconcopolymere containing quaternary ammonium salt according to claim 1, it is characterised in that: in step 2),
The polyetheramine is that the polyethers of primary amine sealing end has the following structure general formula:
Wherein, the natural number that the summation of x+y+z is 1~70.
5. the polyurethane-modified Organosiliconcopolymere containing quaternary ammonium salt according to claim 1, it is characterised in that: in step 1),
The neutralizer is selected from one of formic acid, acetic acid, propionic acid, lauric acid, is the 90%- of tertiary amine compounds molal quantity
110%.
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| CN112726211A (en) * | 2021-01-13 | 2021-04-30 | 日华化学（中国）有限公司 | Preparation method of polyurethane modified organic silicon softening agent |
| CN114775291A (en) * | 2022-05-16 | 2022-07-22 | 杭州美高华颐化工有限公司 | Preparation method of novel quaternized modified block silicone oil |
| CN115787301A (en) * | 2022-11-18 | 2023-03-14 | 杭州传化精细化工有限公司 | Polyurethane modified organic silicon softener and preparation method and application thereof |
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| CN107974837B (en) * | 2017-12-06 | 2020-04-24 | 佛山市顺德区德美瓦克有机硅有限公司 | Polyurethane modified organic silicon copolymer containing quaternary ammonium salt and preparation method thereof |
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| CN111280175A (en) * | 2020-03-06 | 2020-06-16 | 威海诺葳信和新材料有限公司 | Multi-point quaternary ammonium salt modified organic silicon copolymer type antibacterial agent and preparation method thereof |
| CN111471067B (en) * | 2020-05-22 | 2023-07-21 | 中国人民解放军空军军医大学 | Methacrylate modified organic silicon quaternary ammonium salt and preparation method and application thereof |
| CN112279994B (en) * | 2020-11-06 | 2022-08-16 | 江苏海洋大学 | Application of polyurethane-based interpenetrating network polymer in surface modification of medical catheter |
| CN115710826B (en) * | 2022-12-05 | 2024-04-05 | 吉林大学 | Giant tow carbon fiber precursor oiling agent and preparation method thereof |
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| CN114775291A (en) * | 2022-05-16 | 2022-07-22 | 杭州美高华颐化工有限公司 | Preparation method of novel quaternized modified block silicone oil |
| CN114775291B (en) * | 2022-05-16 | 2023-06-27 | 杭州美高华颐化工有限公司 | Preparation method of novel quaternized modified block silicone oil |
| CN115787301A (en) * | 2022-11-18 | 2023-03-14 | 杭州传化精细化工有限公司 | Polyurethane modified organic silicon softener and preparation method and application thereof |
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| CN107974837A (en) | 2018-05-01 |
| CN107974837B (en) | 2020-04-24 |
| CN110527052B (en) | 2021-04-06 |
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