CN110219174A - A kind of no soap water-dispersion type water-refusing oil-refusing finishing agent and preparation method thereof - Google Patents
A kind of no soap water-dispersion type water-refusing oil-refusing finishing agent and preparation method thereof Download PDFInfo
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- CN110219174A CN110219174A CN201910637793.0A CN201910637793A CN110219174A CN 110219174 A CN110219174 A CN 110219174A CN 201910637793 A CN201910637793 A CN 201910637793A CN 110219174 A CN110219174 A CN 110219174A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/22—Esters containing halogen
- C08F220/24—Esters containing halogen containing perhaloalkyl radicals
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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
- D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/263—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof
- D06M15/277—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof containing fluorine
-
- 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
- D06M2200/10—Repellency against liquids
- D06M2200/11—Oleophobic properties
-
- 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
- D06M2200/10—Repellency against liquids
- D06M2200/12—Hydrophobic properties
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
The present invention discloses a kind of no soap water-dispersion type water-refusing oil-refusing finishing agent, by weight, including following raw material: vinyl monomer, initiator, organic solvent and fluorochemical monomer, water；The fluorochemical monomer accounts for the 8%~70% of the gross mass of the fluorochemical monomer and vinyl monomer；The quality of the organic solvent is the 15~35% of the gross mass of the fluorochemical monomer and vinyl monomer；The quality of the water is 2~5 times of the gross mass of the fluorochemical monomer and vinyl monomer；The quality of the initiator is the 0.2~0.5% of the gross mass of the fluorochemical monomer and vinyl monomer.Water-refusing oil-refusing finishing agent of the invention is also dispersed using high molecular polymer, avoid the use of emulsifier, the stability and homogeneity of water-refusing oil-refusing finishing agent are improved, so that the fluorine-containing water-refusing oil-refusing finishing agent of short carbon chain of preparation, the water and oil repellant performance on fabric find full expression.
Description
Technical field
The present invention relates to a kind of no soap water-dispersion type water-refusing oil-refusing finishing agents and preparation method thereof.
Background technique
Currently, carrying out finishing functions, the water and oil repellant performance of Lai Shixian fabric to fabric frequently with water-refusing oil-refusing finishing agent.
The copolymer of (methyl) Perfluoroalkyl acrylate is used to prepare water-refusing oil-refusing finishing agent by routine, still (methyl) acrylic acid
Perfluoro alkyl ethyl, which exists, decomposes or is metabolized a possibility that generating PFOA (perfluoro caprylic acid, Perfluorooctanoic Acid).
EPA (the U.S. environment protection Room) research report " Preliminary Risk Assessment of the
Developmental Toxicity Associated with Exp-osure to Perfluorooctanoic Acid
And its Salts " specifies that the PFOA of one of long-chain fluorinated alkyl compound brings load to environment, and there are bioaccumulations
And bio-toxicity.Therefore, presently relevant bill has been announced, and will implement to disable to it.
Thus selecting becomes fluorine-containing (methyl) the acrylics monomer progress substitution studies of short carbon chain that carrying capacity of environment is low
Develop hot spot.Due to the water and oil repellant characteristic of fluorochemical monomer, it is made to be difficult to disperse in water.Method using emulsion polymerization is one
A effective means, but the residual of emulsifier can have an impact to the water and oil repellant effect of product.Many patents also report various
The emulsifier of type, the aqueous liquid dispersion of water and oil repellent (CN1878846A) such as containing nonionic surface active agent, report
Synthesized using the compound emulsifying agent that a variety of different surfaces activating agents form for fluorine-containing latex, but emulsion intercalation method with refuse
Water oil repellency is unsatisfactory.Therefore, it is necessary to a kind of new water-refusing oil-refusing finishing agent, with solve presently, there are the technical issues of.
Summary of the invention
In view of the above existing problems in the prior art, the present invention provides a kind of no soap water-dispersion type water-refusing oil-refusing finishing agent and
Preparation method.
To achieve the goals above, a kind of no soap water-dispersion type water-refusing oil-refusing finishing agent that the present invention uses, by weight
Meter, including following raw material: vinyl monomer, initiator, organic solvent and fluorochemical monomer, water；
The fluorochemical monomer accounts for the 8%~70% of the gross mass of the fluorochemical monomer and vinyl monomer；
The quality of the organic solvent is the 15~35% of the gross mass of the fluorochemical monomer and vinyl monomer；
The quality of the water is 2~5 times of the gross mass of the fluorochemical monomer and vinyl monomer；
The quality of the initiator is the 0.2~0.5% of the gross mass of the fluorochemical monomer and vinyl monomer.
The fluorochemical monomer has following general formula:
(Rf- Y)mZ formula 1；
Wherein, RfFor the linear chain or branched chain perfluoroalkyl of C4~C7, Y is divalent organic base or singly-bound, and Z is polymerism insatiable hunger
And group, and m is 1 or 2；The divalent organic base is selected from one of ester group, amide groups, alkylidene, ether, aromatic series base
Or several moiety combinations.
As a further improvement, the fluorochemical monomer is using any one expression in following formula 1 a~1e:
Wherein, X is hydrogen or methyl；N is 1~10.
It further improves, the fluorochemical monomer is selected from any one monomer that following formula 1 a-I~1e-I is indicated:
The vinyl monomer is selected from (methyl) acrylic acid of alkyl (methyl) esters of acrylic acid, fat or ester ring type alkenyl
One of lipid, alkenyl halide, the vinyl ester of fatty acid, N- alkyl Maleimide class, acrylamide monomers or
The combination of several monomers.
The initiator uses azo-bis-isobutyrate hydrochloride.
The organic solvent is mixed selected from one or more of propylene glycol, propylene glycol monomethyl ether, tripropylene glycol.
In addition, the present invention also provides a kind of preparation methods of no soap water-dispersion type water-refusing oil-refusing finishing agent, including
Step: being added the 10-90% of vinyl monomer, the 30-60% and solvent of initiator into reaction system in a nitrogen atmosphere,
Carry out polymerization reaction at 55 DEG C~65 DEG C, form high polymer dispersion, be then added into reaction system fluorochemical monomer,
Residual ethylene base monomer and remaining initiator, polymerization reaction is carried out at 55 DEG C~65 DEG C, it is whole to form water-dispersion type water and oil repellant
Manage agent.
Compared with prior art, the present invention substitutes the length in routine techniques by being introduced into the whole-fluoroalkyl chain segment of short carbon chain
Carbochain whole-fluoroalkyl chain segment, to reduce its bio-toxicity and permanently building up property.Water-refusing oil-refusing finishing agent of the invention is also sharp
Dispersed with high molecular polymer, avoid the use of emulsifier, improves the stability and homogeneity of water-refusing oil-refusing finishing agent,
So that the fluorine-containing water-refusing oil-refusing finishing agent of short carbon chain of preparation, the water and oil repellant performance on fabric find full expression.
Specific embodiment
In order to make the objectives, technical solutions and advantages of the present invention clearer, the present invention is carried out below further detailed
It describes in detail bright.However, it should be understood that the specific embodiments described herein are merely illustrative of the present invention, it is not limited to this hair
Bright range.
Unless otherwise defined, all technical terms and scientific terms used herein are led with technology of the invention is belonged to
The normally understood meaning of the technical staff in domain is identical, and term as used herein in the specification of the present invention is intended merely to retouch
State the purpose of specific embodiment, it is not intended that in the limitation present invention.
A kind of no soap water-dispersion type water-refusing oil-refusing finishing agent, by weight, including following raw material: vinyl monomer draws
Send out agent, organic solvent and fluorochemical monomer, water；
The fluorochemical monomer accounts for the 8%~70% of the gross mass of the fluorochemical monomer and vinyl monomer；
The quality of the organic solvent is the 15~35% of the gross mass of the fluorochemical monomer and vinyl monomer；
The quality of the water is 2~5 times of the gross mass of the fluorochemical monomer and vinyl monomer；
The quality of the initiator is the 0.2~0.5% of the gross mass of the fluorochemical monomer and vinyl monomer.
The fluorochemical monomer has following general formula:
(Rf- Y)mZ formula 1；
Wherein, RfFor the linear chain or branched chain perfluoroalkyl of C4~C7, Y is divalent organic base or singly-bound, and Z is polymerism insatiable hunger
And group, and m is 1 or 2；The divalent organic base is selected from one of ester group, amide groups, alkylidene, ether, aromatic series base
Or several moiety combinations.
As a further improvement, the fluorochemical monomer is using any one expression in following formula 1 a~1e:
Wherein, X is hydrogen or methyl；N is 1~10.
It further improves, the fluorochemical monomer is selected from any one monomer that following formula 1 a-I~1e-I is indicated:
The vinyl monomer is selected from (methyl) acrylic acid of alkyl (methyl) esters of acrylic acid, fat or ester ring type alkenyl
One of lipid, alkenyl halide, the vinyl ester of fatty acid, N- alkyl Maleimide class, acrylamide monomers or
The combination of several monomers.
The initiator uses azo-bis-isobutyrate hydrochloride.
The organic solvent is mixed selected from one or more of propylene glycol, propylene glycol monomethyl ether, tripropylene glycol.
In addition, the present invention also provides a kind of preparation methods of no soap water-dispersion type water-refusing oil-refusing finishing agent, including
Step: being added the 10-90% of vinyl monomer, the 30-60% and solvent of initiator into reaction system in a nitrogen atmosphere,
Carry out polymerization reaction at 55 DEG C~65 DEG C, form high polymer dispersion, be then added into reaction system fluorochemical monomer,
Residual ethylene base monomer and remaining initiator, polymerization reaction is carried out at 55 DEG C~65 DEG C, it is whole to form water-dispersion type water and oil repellant
Manage agent.
Embodiment 1
A kind of no soap water-dispersion type water-refusing oil-refusing finishing agent, is prepared as follows: acrylic acid ten is put into three-necked flask
Octaester 90.00g, Dimethylaminoethyl Methacrylate 13.50g are added after propylene glycol monomethyl ether 126.00g, nitrogen displacement
1.25g initiator azo-bis-isobutyrate hydrochloride, while warming-in-water is reacted 4 hours to 60 DEG C, obtains polymeric dispersant,
Then, dispersing agent is fitted into autoclave, after nitrogen displacement, puts into the perfluorinated monomers 270.00g as shown in formula 1a-I, add
Enter 54.00g vinyl chloride, 1.25g initiator azo-bis-isobutyrate hydrochloride is then added, while warming-in-water reacts 4 to 60 DEG C
Hour, obtain water-refusing oil-refusing finishing agent 1.
Embodiment 2
A kind of no soap water-dispersion type water-refusing oil-refusing finishing agent, is prepared as follows: acrylic acid ten is put into three-necked flask
Octaester 90.00g, Dimethylaminoethyl Methacrylate 13.50g are added after propylene glycol monomethyl ether 126.00g, nitrogen displacement
1.25g initiator azo-bis-isobutyrate hydrochloride, while warming-in-water is reacted 4 hours to 60 DEG C, obtains polymeric dispersant,
Then, dispersing agent is fitted into autoclave, after nitrogen displacement, puts into the perfluorinated monomers 270.00g as shown in formula 1b-I, add
Enter 54.00g vinyl chloride, 1.25g initiator azo-bis-isobutyrate hydrochloride is then added, while warming-in-water reacts 4 to 60 DEG C
Hour, obtain water-refusing oil-refusing finishing agent 2.
Comparative example 1
A kind of fluorine-containing water-refusing oil-refusing finishing agent, is prepared as follows: the perfluor as shown in formula 1a-I is put into 2L beaker
Monomer 270.00g, octadecyl acrylate 90.00g, acetoacetoxyethyl methacrylate 13.50g, epoxidized soybean oil
22.50g, octadecyltrimethylammonium chloride 21.00g, polyoxyethylene lauryl ether 5.00g, anhydrosorbitol as shown in formula 2-a
Sorbitane monooleate 5.50g, tripropylene glycol 126.00g, lauryl mercaptan 0.90g and deionized water 889.35g, pass through
High pressure homogenizer emulsifies 15min, obtains stabilized oil-in-water lotion.Then, lotion is fitted into autoclave, nitrogen displacement
Afterwards, 54.00g vinyl chloride is added, 2.25g initiator azo-bis-isobutyrate hydrochloride is then added, while warming-in-water is to 60 DEG C,
Reaction 4 hours obtains comparison finishing agent 1.
Comparative example 2
In this comparative example, the cationic surfactant in embodiment 1 is replaced with into octadecyl trimethyl chlorine
Change ammonium.
Therefore, in the present embodiment, a kind of fluorine-containing water-refusing oil-refusing finishing agent is provided, is prepared as follows: in 2L beaker
Put into perfluorinated monomers 270.00g, octadecyl acrylate 90.00g as shown in formula 1b-I, acetoacetoxyethyl second
Ester 13.50g, epoxidized soybean oil 22.50g, octadecyltrimethylammonium chloride 21.00g, the polyoxyethylene moon as shown in formula 2-a
Osmanthus base ether 5.00g, dehydrated sorbitol mono-fatty acid ester 5.50g, tripropylene glycol 126.00g, lauryl mercaptan 0.90g and
Deionized water 889.35g emulsifies 15min by high pressure homogenizer, obtains stabilized oil-in-water lotion.Then, lotion is packed into high
It presses in reaction kettle, after nitrogen displacement, 54.00g vinyl chloride is added, 2.25g initiator azo-bis-isobutyrate hydrochloride is then added,
Warming-in-water is reacted 4 hours to 60 DEG C simultaneously, obtains comparison finishing agent 2.
Verify embodiment
In the present embodiment, the water-refusing oil-refusing finishing agent 1~2 and comparative example 1 that applicant obtains Examples 1 to 2
The waterproof and oilproof performance of~2 comparison finishing agents 1~2 obtained is tested.
In the present embodiment, it is utilized respectively the water-refusing oil-refusing finishing agent 1~2 and 1~2 pair of finishing agent of comparison same is knitted
Object is arranged, finishing technique are as follows: (5~50g/L, pH 5.0~7.0 rolls rod pressure 2kg/cm to an immersing and rolling finishing agent2)→
Dry → bake (180 DEG C, 30s) → resurgence → evaluation.Test is 210T black spring Asia textile fabric with fabric.
Assessment item mainly includes following items:
(1) according to AATCC-22 testing water-proof performance: being drenched 250ml water in 25~30s using water drenching test device
It is sprinkled upon on measured object, observes fabric wetting state, waterproof performance is evaluated according to table 1.
The evaluation of 1 waterproof performance of table
(2) test oil preventing performance according to AATCC-118: three places on test cloth, which are added dropwise shown in few drops of tables 2, to be surveyed
Test solution is impregnated with state after observing 30s, and the highest point of the grease proofness assigned using the test fluid for not occurring being impregnated with is as grease proofing etc.
Grade.
The evaluation of 2 oil preventing performance of table
(3) test storage stability: by effective content be 30% water-refusing oil-refusing finishing agent in 45 DEG C stand 1 month after,
Observe the generation of sedimentation.Judgment criteria: zero: absolutely not sediment；△: there is a small amount of sediment；×: there are many sediments.
(4) mechanical stability: it is 0.2% that water-refusing oil-refusing finishing agent, which is diluted to effective concentration, by tap water, with high speed
Cutter, will be on the scum filtering to black filter paper of appearance after 4000rpm stirs 15min.Judgment criteria: zero: absolutely not
Dross；△: there is a small amount of dross；×: there are many drosses.
(5) field trash stability: it is 0.2%, Xiang Qi that water-refusing oil-refusing finishing agent, which is diluted to effective concentration, by tap water
The disperse dyes of middle addition 0.01%, observe the appearance of condensation product after being sufficiently mixed.Judgment criteria: zero: absolutely not agglutinator
It generates；△: a small amount of agglutinator generates；×: there are many agglutinators.
Evaluation result is see table 3.
3 embodiment of table and comparative example properties of product compare
Note: (a) finishing fluid working fluid concentration 10g/L, platen pressure 2kg/cm2, pick-up 86.49%；
(b) finishing fluid working fluid concentration 15g/L, platen pressure 2kg/cm2, pick-up 66.39%；
(c) finishing fluid working fluid concentration 25g/L, platen pressure 2kg/cm2, pick-up 98.56%；
(d) finishing fluid working fluid concentration 60g/L, platen pressure 2kg/cm2, pick-up 86.57%；
(e) finishing fluid working fluid concentration 75g/L, platen pressure 2kg/cm2, pick-up 96.39%.
In the present invention, the long carbon chain perfluor alkane in routine techniques is substituted by being introduced into the whole-fluoroalkyl chain segment of short carbon chain
Base segment, to reduce its bio-toxicity and permanently building up property.Meanwhile by introducing rigid element, fluorine-containing groups are improved
Crystallinity.Furthermore the water-refusing oil-refusing finishing agent of the invention is also dispersed using high molecular polymer, and emulsifier is avoided
Use, improve the stability and homogeneity of water-refusing oil-refusing finishing agent so that preparation the fluorine-containing water and oil repellent finish of short carbon chain
Water and oil repellant performance of the agent on fabric finds full expression.
The present invention is described by above-mentioned related embodiment, however above-described embodiment is only to implement example of the invention.
It must be noted that, it has been disclosed that embodiment be not limiting as the scope of the present invention.On the contrary, being contained in the spirit of claims
And range modification and impartial setting be included in the scope of the present invention.
Claims (8)
1. a kind of no soap water-dispersion type water-refusing oil-refusing finishing agent, which is characterized in that by weight, including following raw material: ethylene
Base monomer, initiator, organic solvent and fluorochemical monomer, water；
The fluorochemical monomer accounts for the 8%~70% of the gross mass of the fluorochemical monomer and vinyl monomer；
The quality of the organic solvent is the 15~35% of the gross mass of the fluorochemical monomer and vinyl monomer；
The quality of the water is 2~5 times of the gross mass of the fluorochemical monomer and vinyl monomer；
The quality of the initiator is the 0.2~0.5% of the gross mass of the fluorochemical monomer and vinyl monomer.
2. a kind of no soap water-dispersion type water-refusing oil-refusing finishing agent according to claim 1, which is characterized in that the fluorine-containing list
Body has following general formula:
(Rf- Y)mZ formula 1；
Wherein, RfFor the linear chain or branched chain perfluoroalkyl of C4~C7, Y is divalent organic base or singly-bound, and Z is polymerism unsaturated group
Group, and m is 1 or 2；The divalent organic base is selected from one of ester group, amide groups, alkylidene, ether, aromatic series base or several
Kind moiety combinations.
3. a kind of no soap water-dispersion type water-refusing oil-refusing finishing agent according to claim 2, which is characterized in that the fluorine-containing list
Body is using any one expression in following formula 1 a~1e:
Wherein, X is hydrogen or methyl；N is 1~10.
4. a kind of no soap water-dispersion type water-refusing oil-refusing finishing agent according to claim 3, which is characterized in that the fluorine-containing list
Body is selected from any one monomer that following formula 1 a-I~1e-I is indicated:
5. a kind of no soap water-dispersion type water-refusing oil-refusing finishing agent according to claim 1, which is characterized in that the vinyl
Monomer is selected from alkyl (methyl) esters of acrylic acid, fat or (methyl) acrylics of ester ring type alkenyl, alkenyl halide, fat
The combination of the vinyl ester, N- alkyl Maleimide class, one or more of acrylamide monomers monomer of acid.
6. a kind of no soap water-dispersion type water-refusing oil-refusing finishing agent according to claim 1, which is characterized in that the initiator
Using azo-bis-isobutyrate hydrochloride.
7. a kind of no soap water-dispersion type water-refusing oil-refusing finishing agent according to claim 1, which is characterized in that described organic molten
Agent is mixed selected from one or more of propylene glycol, propylene glycol monomethyl ether, tripropylene glycol.
8. a kind of preparation method of any one of claim 1-7 no soap water-dispersion type water-refusing oil-refusing finishing agent, feature exist
In, comprising steps of be added in a nitrogen atmosphere into reaction system the 10-90% of vinyl monomer, initiator 30-60% and
Solvent carries out polymerization reaction at 55 DEG C~65 DEG C, forms high polymer dispersion, is then added and contains into reaction system
Fluorine monomer, residual ethylene base monomer and remaining initiator, polymerization reaction is carried out at 55 DEG C~65 DEG C, forms water-dispersion type water repellent
Oil-refusing finishing agent.
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| CN104074052A (en) * | 2014-05-21 | 2014-10-01 | 巨化集团技术中心 | Aqueous dispersion liquid of fluorine/silicon-copolymerized water and oil resistant finishing agent |
| CN106555336A (en) * | 2016-11-23 | 2017-04-05 | 苏州联胜化学有限公司 | A kind of fluorine-containing water-refusing oil-refusing finishing agent and preparation method thereof |
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2019
- 2019-07-15 CN CN201910637793.0A patent/CN110219174A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102159605A (en) * | 2008-09-15 | 2011-08-17 | 大金工业株式会社 | Aqueous polymer dispersion composition and surface treatment agent |
| CN102516451A (en) * | 2011-12-14 | 2012-06-27 | 太仓中化环保化工有限公司 | Water dispersive fluorine-containing water and oil repellent and preparation method thereof |
| CN104074052A (en) * | 2014-05-21 | 2014-10-01 | 巨化集团技术中心 | Aqueous dispersion liquid of fluorine/silicon-copolymerized water and oil resistant finishing agent |
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