CN110144189A - A kind of water soluble flocking glue and preparation method thereof - Google Patents
A kind of water soluble flocking glue and preparation method thereof Download PDFInfo
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- CN110144189A CN110144189A CN201910393723.5A CN201910393723A CN110144189A CN 110144189 A CN110144189 A CN 110144189A CN 201910393723 A CN201910393723 A CN 201910393723A CN 110144189 A CN110144189 A CN 110144189A
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- parts
- water
- water soluble
- flocking glue
- chlorine
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims abstract description 98
- 239000003292 glue Substances 0.000 title claims abstract description 65
- 238000002360 preparation method Methods 0.000 title claims abstract description 32
- 239000002253 acid Substances 0.000 claims abstract description 42
- 229920002873 Polyethylenimine Polymers 0.000 claims abstract description 26
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 26
- 239000011737 fluorine Substances 0.000 claims abstract description 26
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims abstract description 25
- 239000003995 emulsifying agent Substances 0.000 claims abstract description 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 20
- 229920002635 polyurethane Polymers 0.000 claims abstract description 17
- 239000004814 polyurethane Substances 0.000 claims abstract description 17
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims abstract description 16
- 150000002148 esters Chemical class 0.000 claims abstract description 16
- 230000004048 modification Effects 0.000 claims abstract description 16
- 238000012986 modification Methods 0.000 claims abstract description 16
- 229920000728 polyester Polymers 0.000 claims abstract description 16
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 14
- 239000012948 isocyanate Substances 0.000 claims abstract description 14
- 150000002513 isocyanates Chemical class 0.000 claims abstract description 14
- 150000001875 compounds Chemical class 0.000 claims abstract description 13
- 239000003999 initiator Substances 0.000 claims abstract description 13
- 239000002994 raw material Substances 0.000 claims abstract description 13
- 239000004971 Cross linker Substances 0.000 claims abstract description 10
- 238000000034 method Methods 0.000 claims abstract description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 21
- -1 silicol class compound Chemical class 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 18
- 238000002156 mixing Methods 0.000 claims description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
- 238000003756 stirring Methods 0.000 claims description 11
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 10
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 claims description 10
- 229940051841 polyoxyethylene ether Drugs 0.000 claims description 9
- 229920000056 polyoxyethylene ether Polymers 0.000 claims description 9
- 230000001804 emulsifying effect Effects 0.000 claims description 7
- JOHWNGGYGAVMGU-UHFFFAOYSA-N trifluorochlorine Chemical compound FCl(F)F JOHWNGGYGAVMGU-UHFFFAOYSA-N 0.000 claims description 7
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 6
- 239000004359 castor oil Substances 0.000 claims description 5
- 235000019438 castor oil Nutrition 0.000 claims description 5
- 230000008859 change Effects 0.000 claims description 5
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 claims description 5
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical group [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 claims description 5
- 235000019394 potassium persulphate Nutrition 0.000 claims description 5
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 5
- WQQPDTLGLVLNOH-UHFFFAOYSA-M sodium;4-hydroxy-4-oxo-3-sulfobutanoate Chemical compound [Na+].OC(=O)CC(C([O-])=O)S(O)(=O)=O WQQPDTLGLVLNOH-UHFFFAOYSA-M 0.000 claims description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims description 4
- RCEAADKTGXTDOA-UHFFFAOYSA-N OS(O)(=O)=O.CCCCCCCCCCCC[Na] Chemical group OS(O)(=O)=O.CCCCCCCCCCCC[Na] RCEAADKTGXTDOA-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- LRMHFDNWKCSEQU-UHFFFAOYSA-N ethoxyethane;phenol Chemical compound CCOCC.OC1=CC=CC=C1 LRMHFDNWKCSEQU-UHFFFAOYSA-N 0.000 claims description 4
- 239000000706 filtrate Substances 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- 239000012074 organic phase Substances 0.000 claims description 4
- 239000000047 product Substances 0.000 claims description 4
- 238000000926 separation method Methods 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
- MHABMANUFPZXEB-UHFFFAOYSA-N O-demethyl-aloesaponarin I Natural products O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=C(O)C(C(O)=O)=C2C MHABMANUFPZXEB-UHFFFAOYSA-N 0.000 claims description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 3
- 229940113088 dimethylacetamide Drugs 0.000 claims description 3
- 239000003431 cross linking reagent Substances 0.000 claims description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
- JTXUAHIMULPXKY-UHFFFAOYSA-N 3-trihydroxysilylpropan-1-amine Chemical compound NCCC[Si](O)(O)O JTXUAHIMULPXKY-UHFFFAOYSA-N 0.000 claims 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 claims 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 claims 1
- 235000011130 ammonium sulphate Nutrition 0.000 claims 1
- 150000002191 fatty alcohols Chemical class 0.000 claims 1
- 150000003333 secondary alcohols Chemical class 0.000 claims 1
- 230000007613 environmental effect Effects 0.000 abstract description 7
- 230000008901 benefit Effects 0.000 abstract description 6
- 230000035699 permeability Effects 0.000 abstract description 4
- 230000001846 repelling effect Effects 0.000 abstract description 4
- 239000000853 adhesive Substances 0.000 description 14
- 230000001070 adhesive effect Effects 0.000 description 14
- 230000000052 comparative effect Effects 0.000 description 12
- 244000144992 flock Species 0.000 description 10
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 8
- 238000007711 solidification Methods 0.000 description 6
- 230000008023 solidification Effects 0.000 description 6
- 238000004132 cross linking Methods 0.000 description 5
- 238000007789 sealing Methods 0.000 description 5
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 4
- 238000004026 adhesive bonding Methods 0.000 description 3
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 230000018109 developmental process Effects 0.000 description 3
- 238000011031 large-scale manufacturing process Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000004753 textile Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- YEMJVHOPMVQUGS-CZPYZCIJSA-N [(2r,3r,4r,5r)-2,3,4,5-tetrahydroxy-6-(2-isocyano-3-methylbut-2-enoyl)oxyhexyl] 2-isocyano-3-methylbut-2-enoate Chemical compound CC(C)=C([N+]#[C-])C(=O)OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)COC(=O)C([N+]#[C-])=C(C)C YEMJVHOPMVQUGS-CZPYZCIJSA-N 0.000 description 2
- VDRSDNINOSAWIV-UHFFFAOYSA-N [F].[Si] Chemical group [F].[Si] VDRSDNINOSAWIV-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000007812 deficiency Effects 0.000 description 2
- 238000009837 dry grinding Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000001165 hydrophobic group Chemical group 0.000 description 2
- 229920000058 polyacrylate Polymers 0.000 description 2
- 230000000379 polymerizing effect Effects 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 150000003242 quaternary ammonium salts Chemical group 0.000 description 2
- 239000003566 sealing material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- CZLKBLLCUJHJHD-UHFFFAOYSA-N 4,5-di(propan-2-yl)-4,5-dihydro-1H-imidazole hydrochloride Chemical compound Cl.C(C)(C)C1C(N=CN1)C(C)C CZLKBLLCUJHJHD-UHFFFAOYSA-N 0.000 description 1
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
- RZYKUPXRYIOEME-UHFFFAOYSA-N CCCCCCCCCCCC[S] Chemical group CCCCCCCCCCCC[S] RZYKUPXRYIOEME-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 description 1
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 1
- 241001074085 Scophthalmus aquosus Species 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 125000005396 acrylic acid ester group Chemical group 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 238000005842 biochemical reaction Methods 0.000 description 1
- 239000004568 cement Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical class ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- FJQXCDYVZAHXNS-UHFFFAOYSA-N methadone hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(CC(C)N(C)C)(C(=O)CC)C1=CC=CC=C1 FJQXCDYVZAHXNS-UHFFFAOYSA-N 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- LHJROESDWMXAKD-UHFFFAOYSA-N trihydroxysilicon Chemical compound O[Si](O)O LHJROESDWMXAKD-UHFFFAOYSA-N 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
-
- 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
- C08G18/30—Low-molecular-weight compounds
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3893—Low-molecular-weight compounds having heteroatoms other than oxygen containing silicon
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Laminated Bodies (AREA)
Abstract
The present invention relates to a kind of water soluble flocking glues, it is characterized in that, it is made of each raw material of following parts by weight: 20-30 parts of water-soluble acrylate-based client hyper-branched polyester, 5-10 parts of 3- chlorine-2-hydroxyl propyl acrylate Ionization Modification hyperbranched polyethyleneimine, 30-40 parts of terminal hydroxy group aqueous polyurethane, 1-5 parts of closed isocyanate crosslinker, PEARLITOL 25C 1,1-3 parts of 6- bis- (2- isocyano group -3- methyl-2-butene acid esters), 0.5-1 parts of fluorine-containing ortho-siliformic acid class compound, 2-5 parts of emulsifier, 0.1-0.5 parts of initiator, 50-60 parts of water.The invention also discloses the preparation method of the water soluble flocking glue and application methods.Water soluble flocking glue disclosed by the invention has water resistance, wearability, weatherability good, and adhesion strength is high, and stability, water repelling property, feel and breathable moisture permeability are excellent, the advantages of using safety and environmental friendliness.
Description
Technical field
The invention belongs to adhesive technology fields, and in particular to a kind of water soluble flocking glue and preparation method thereof.
Background technique
With the development and improvement of living standard of society, automobile industry development is rapid, and people are to the sealing in car industry
Material requirements is higher and higher, and the sealing material for developing excellent performance becomes the hot spot currently studied in the industry.Automobile flocking sealing strip is
A kind of more typical sealing material of automotive field, mainly includes vehicle window side seal item (water is cut) and windowpane run channel, function
It can be the sealing of external wind and rain, dust entrance, noise-decreasing, glass is prevented to be easier sliding etc., and in automobile flocking sealing strip
Manufacturing process in a kind of essential reagent be Flock Adhesive, the quality of performance directly affects the close of automobile flocking sealing strip
Seal effect.Therefore, it is imperative to develop the Flock Adhesive haveing excellent performance.
The solvent difference that Flock Adhesive is used according to it is broadly divided into organic solvent type glue and water-base cement, due to country and ground
The formulation of side increasingly strict environmental protection policy and laws and regulations, water soluble flocking glue become Flock Adhesive industry with environmentally protective advantage
The main trend currently or even from now on developed for a period of time, will obtain more universal use.More aqueous plant is used at present
Suede glue is polyacrylate emulsion adhesive, it is inexpensive, make and use conveniently, it is ageing-resistant and have very well to multiple fiber
Bonding force be its strong point, still, there is also deficiency in terms of wear-resisting, water-fast and flexibility, especially acrylic acid ester emulsion is planted
The cross-linking monomer of suede glue is mostly hydroxymethyl acrylamide and crosslinking agent is mostly methyl-etherified melamine methylol, the methylol contained
Group will be slow ground release formaldehyde, is more toxic, is not able to satisfy the environmental requirement increasingly stringent to textile.
Occur in the prior art with aqueous polyurethane water soluble flocking glue as main component, this water soluble flocking glue is just
The shortcomings that avoiding polyacrylate Flock Adhesive, but it still has the bad problem of water resistance, wearability, often in reality
It makes troubles in industrial production.The also generally existing adhesion strength of water soluble flocking glue on the market is not high, stability, water resistant
The poor defect of performance, feel and breathable moisture permeability, there are also part adhesives to exist using dangerous, baking temperature is too high
Disadvantage.
Therefore, a kind of excellent combination property is developed, is accorded with the demands of the market using the Flock Adhesive of safety and environmental protection, is had extensive
Market value and application prospect have very important significance to the development for promoting Aqueous Adhesives industry.
Summary of the invention
A kind of water soluble flocking glue and preparation method thereof is provided the invention aims to overcome the deficiencies in the prior art, it should
Preparation method is simple and easy to operate, prepares that raw material is environmentally friendly, and preparation cost is cheap, is suitble to large-scale production；The water being prepared
Property Flock Adhesive have water resistance, wearability, weatherability good, adhesion strength is high, stability, water repelling property, feel and air-moisture-permeable
Property is excellent, the advantages of using safety and environmental friendliness.
In order to achieve the above objectives, the technical scheme adopted by the invention is as follows: a kind of water soluble flocking glue, by following parts by weight
Each raw material is made: 20-30 parts of water-soluble acrylate-based client hyper-branched polyester, the ionization of 3- chlorine-2-hydroxyl propyl acrylate change
Property 5-10 parts of hyperbranched polyethyleneimine, 30-40 parts of terminal hydroxy group aqueous polyurethane, 1-5 parts of closed isocyanate crosslinker, D-
Mannitol 1,6- bis- (2- isocyano group -3- methyl-2-butene acid esters) 1-3 parts of (No. CAS: 61241-59-6), fluorine-containing trihydroxy silicon
0.5-1 parts of alkyl compound, 2-5 parts of emulsifier, 0.1-0.5 parts of initiator, 50-60 parts of water.
Further, the emulsifier is lauryl sodium sulfate, secondary alcohol fatty alcohol polyoxyethylene ether, castor oil polyoxy second
At least one of alkene ether and alkyl phenol ether sulfosuccinic acid sodium salt.
Further, the initiator is potassium peroxydisulfate, sodium peroxydisulfate, ammonium persulfate, azo dicyclohexyl formonitrile HCN salt
At least one of hydrochlorate.
Further, the preparation side of the 3- chlorine-2-hydroxyl propyl acrylate Ionization Modification hyperbranched polyethyleneimine
Method includes the following steps: 3- chlorine-2-hydroxyl propyl acrylate, hyperbranched polyethyleneimine being dissolved in n,N-dimethylacetamide
In, it being stirred to react at 60-80 DEG C 4-6 hours, n,N-dimethylacetamide is evaporated off in back spin, with ether washed product 3-5 times,
It is placed at 80-90 DEG C of vacuum oven and is dried to constant weight again.
Preferably, the 3- chlorine-2-hydroxyl propyl acrylate, hyperbranched polyethyleneimine, n,N-dimethylacetamide
Mass ratio is 1:1:(8-12).
Further, the preparation method of the fluorine-containing ortho-siliformic acid class compound includes the following steps: trifluoro chlorine Portugal
Acid, 3- aminopropyl ortho-siliformic acid mixing, be stirred to react at 60-80 DEG C 3-5 hour, after 3:1 in mass ratio addition water and two
Chloromethanes carries out liquid separation, takes organic phase, removed water with anhydrous magnesium sulfate, filters, and takes filtrate, and revolving removes methylene chloride, contained
Fluorine silicol class compound.
Preferably, the trifluoro chlorine Portugal acid, 3- aminopropyl ortho-siliformic acid mass ratio be 1.77:1.
Further, the preparation method of the water soluble flocking glue, includes the following steps:
S1, water and emulsifier are added in emulsifying kettle, the additional amount of water is the 40-50% of total amount, the addition of emulsifier
Amount is the 80-90% of total amount, and water-soluble acrylate-based client hyper-branched polyester, 3- chlorine-2-hydroxyl acrylic acid are added while stirring
Propyl ester Ionization Modification hyperbranched polyethyleneimine, terminal hydroxy group aqueous polyurethane obtain mixture A after mixing evenly；
S2, the emulsifier of the water of surplus and surplus is added in another emulsifying kettle, enclosed type is added while stirring
Isocyanate crosslinking, PEARLITOL 25C 1,6- bis- (2- isocyano group -3- methyl-2-butene acid esters), fluorine-containing ortho-siliformic acid class
It closes object and initiator obtains mixture B after mixing evenly；
S3, it mixes, stirs by the mixture A being prepared by step S1 and by the mixture B that step S2 is prepared
After mixing uniformly, the water soluble flocking glue is obtained.
Further, the application method of the water soluble flocking glue includes the following steps: water soluble flocking glue gluing in 60-
80 DEG C by plant, solidification.
Due to the above technical solutions, the present invention has the following advantages over the prior art: water provided by the invention
Property Flock Adhesive preparation method it is simple and easy to operate, prepare that raw material is environmentally friendly, and preparation cost is cheap, be suitble to large-scale production；Preparation
Obtained water soluble flocking glue has water resistance, wearability, weatherability good, and adhesion strength is high, stability, water repelling property, feel and
Breathable moisture permeability is excellent, the advantages of using safety and environmental friendliness.By introduce water-soluble end-allyl group acidic group hyper-branched polyester,
3- chlorine-2-hydroxyl propyl acrylate Ionization Modification the hyperbranched polyethyleneimine, (2- isocyano group -3- first of PEARLITOL 25C 1,6- bis-
Base -2- butenoate), fluorine-containing ortho-siliformic acid class compound these have unsaturated bond monomers, can polymerize in cure stage
Three-dimensional net structure is formed, the comprehensive performance of glue is improved, by polymerizing curable, fluorine silicon structure is introduced, can be further improved material
Comprehensive performance；Hydrophobic group is formed after the fluorine-containing ortho-siliformic acid class compound cures introduced, improves the water-fast of cured glue
Property；Leading-in end hydroxyl aqueous polyurethane and quaternary ammonium salt structure can significantly improve adhesion strength；Closed isocyanate crosslinker is normal
Temperature is lower to be stablized, and is not chemically reacted with other compositions in glue, when solidification, due to heating so that its deblocking, then is had with other
The substance of hydroxyl and amino crosslinks reaction, further increases the comprehensive performance of glue.
Specific embodiment
A kind of water soluble flocking glue of the present invention, is made of each raw material of following parts by weight: water-soluble acrylate-based client over-expense
Change polyester 20-30 parts, 5-10 parts of 3- chlorine-2-hydroxyl propyl acrylate Ionization Modification hyperbranched polyethyleneimine, terminal hydroxy group water
Property 30-40 parts of polyurethane, 1-5 parts of the closed isocyanate crosslinker, (2- isocyano group -3- methyl -2- fourth of PEARLITOL 25C 1,6- bis-
Olefin(e) acid ester) 1-3 parts of (No. CAS: 61241-59-6), 0.5-1 parts of fluorine-containing ortho-siliformic acid class compound, 2-5 parts of emulsifier, initiation
0.1-0.5 parts of agent, 50-60 parts of water.
The emulsifier is lauryl sodium sulfate, secondary alcohol fatty alcohol polyoxyethylene ether, castor oil polyoxyethylene ether and alkane
At least one of base phenolic ether sulfosuccinic acid sodium salt.The initiator is potassium peroxydisulfate, sodium peroxydisulfate, ammonium persulfate, azo
At least one of diisopropyl imidazoline hydrochloride.The 3- chlorine-2-hydroxyl propyl acrylate Ionization Modification hyperbranched poly
The preparation method of aziridine includes the following steps: for 3- chlorine-2-hydroxyl propyl acrylate, hyperbranched polyethyleneimine to be dissolved in
In n,N-dimethylacetamide, it is stirred to react at 60-80 DEG C 4-6 hours, n,N-dimethylacetamide is evaporated off in back spin, uses second
Ether washed product 3-5 times, then be placed at 80-90 DEG C of vacuum oven and dry to constant weight.The 3- chlorine-2-hydroxyl acrylic acid third
Ester, hyperbranched polyethyleneimine, DMAC N,N' dimethyl acetamide mass ratio be 1:1:(8-12).The fluorine-containing ortho-siliformic acid class
The preparation method of compound includes the following steps: to mix trifluoro chlorine Portugal acid, 3- aminopropyl ortho-siliformic acid, at 60-80 DEG C
Be stirred to react 3-5 hours, after 3:1 in mass ratio water and methylene chloride is added, carry out liquid separation, take organic phase, use anhydrous magnesium sulfate
Water removal, filtering take filtrate, and revolving removes methylene chloride, obtains fluorine-containing silicol class compound.Trifluoro chlorine Portugal acid, 3-
The mass ratio of aminopropyl ortho-siliformic acid is 1.77:1.
The preparation method of the water soluble flocking glue includes the following steps: S1, water and emulsifier is added in emulsifying kettle,
The additional amount of water is the 40-50% of total amount, and the additional amount of emulsifier is the 80-90% of total amount, and water-soluble end is added while stirring
Acrylate-based hyper-branched polyester, 3- chlorine-2-hydroxyl propyl acrylate Ionization Modification hyperbranched polyethyleneimine, terminal hydroxy group water
Property polyurethane obtains mixture A after mixing evenly；S2, the emulsifier of the water of surplus and surplus is added to another emulsification
In kettle, closed isocyanate crosslinker, the PEARLITOL 25C 1, (2- isocyano group -3- methyl-2-butenoic acid of 6- bis- are added while stirring
Ester), fluorine-containing ortho-siliformic acid class compound and initiator obtain mixture B after mixing evenly；S3, it will be prepared by step S1
Obtained mixture A and the mixture B mixing being prepared by step S2, after mixing evenly, obtain the water soluble flocking glue.
The application method of the water soluble flocking glue includes the following steps: to be planted water soluble flocking glue gluing in 60-80 DEG C
On object, solidification.The raw material is commercially available.The easy easily behaviour of water soluble flocking glue preparation method provided by the invention
Make, prepare that raw material is environmentally friendly, and preparation cost is cheap, is suitble to large-scale production；The water soluble flocking glue being prepared has water-fast
Property, wearability, weatherability it is good, adhesion strength is high, and stability, water repelling property, feel and breathable moisture permeability are excellent, use is safe,
Green, the advantage of environmental protection.By introduce water-soluble end-allyl group acidic group hyper-branched polyester, 3- chlorine-2-hydroxyl propyl acrylate from
Sonization modified ultra-branching polyethyleneimine, PEARLITOL 25C 1,6- bis- (2- isocyano group -3- methyl-2-butene acid esters), fluorine-containing three hydroxyl
These have the monomer of unsaturated bond to base silane class compound, can polymerize to form three-dimensional net structure in cure stage, improve glue
Comprehensive performance introduce fluorine silicon structure, can be further improved the comprehensive performance of material by polymerizing curable；Fluorine-containing three introduced
Hydrophobic group is formed after silicol class compound cures, improves the water resistance of cured glue；Leading-in end hydroxyl aqueous polyurethane and
Quaternary ammonium salt structure can significantly improve adhesion strength；Closed isocyanate crosslinker is stable at normal temperature, not in glue other at
Distribute biochemical reaction, when solidification, due to heating so that it is unsealed, then crosslinks with other substances with hydroxyl and amino
Reaction, further increases the comprehensive performance of glue.
It is described in detail below in conjunction with to the preferred embodiment of the invention.
Embodiment 1
Embodiment 1 provides a kind of water soluble flocking glue, is made of each raw material of following parts by weight: water-soluble acrylate-based client
20 parts of hyper-branched polyester, 5 parts of 3- chlorine-2-hydroxyl propyl acrylate Ionization Modification hyperbranched polyethyleneimine, terminal hydroxy group are aqueous
30 parts of polyurethane, 1 part of closed isocyanate crosslinker, PEARLITOL 25C 1,6- bis- (2- isocyano group -3- methyl-2-butene acid esters)
1 part, fluorine-containing 0.5 part of ortho-siliformic acid class compound, 2 parts of lauryl sodium sulfate, 0.1 part of potassium peroxydisulfate, 50 parts of water.
The preparation method of the 3- chlorine-2-hydroxyl propyl acrylate Ionization Modification hyperbranched polyethyleneimine, including such as
Lower step: 3- chlorine-2-hydroxyl propyl acrylate 1kg, hyperbranched polyethyleneimine 1kg are dissolved in DMAC N,N' dimethyl acetamide 8kg
In, it is stirred to react at 60 DEG C 4 hours, n,N-dimethylacetamide is evaporated off in back spin, with ether washed product 3 times, then is placed in
It dries at 80 DEG C of vacuum oven to constant weight.
The preparation method of the fluorine-containing ortho-siliformic acid class compound, include the following steps: by trifluoro chlorine Portugal acid 1.77kg,
3- aminopropyl ortho-siliformic acid 1kg mixing, is stirred to react 3 hours at 60 DEG C, after 3:1 in mass ratio water and dichloromethane is added
Alkane carries out liquid separation, takes organic phase, removed water with anhydrous magnesium sulfate, filters, and takes filtrate, and revolving removes methylene chloride, obtains fluorine-containing hydroxyl
Base silane class compound.
The preparation method of the water soluble flocking glue, includes the following steps:
S1, water and emulsifier are added in emulsifying kettle, the additional amount of water is the 40% of total amount, and the additional amount of emulsifier is
Water-soluble acrylate-based client hyper-branched polyester, 3- chlorine-2-hydroxyl propyl acrylate ion is added in the 80% of total amount while stirring
Change modified ultra-branching polyethyleneimine, terminal hydroxy group aqueous polyurethane and obtains mixture A after mixing evenly；
S2, the emulsifier of the water of surplus and surplus is added in another emulsifying kettle, enclosed type is added while stirring
Isocyanate crosslinking, PEARLITOL 25C 1,6- bis- (2- isocyano group -3- methyl-2-butene acid esters), fluorine-containing ortho-siliformic acid class
It closes object and initiator obtains mixture B after mixing evenly；
S3, it mixes, stirs by the mixture A being prepared by step S1 and by the mixture B that step S2 is prepared
After mixing uniformly, the water soluble flocking glue is obtained.
The application method of the water soluble flocking glue includes the following steps: water soluble flocking glue gluing in 60 DEG C by plant
On body, solidification.
Embodiment 2
Embodiment 2 provides a kind of water soluble flocking glue and preparation method thereof, it with it is almost the same in embodiment 1, it is different
It is only that the water soluble flocking glue is made of each raw material of following parts by weight: 23 parts of water-soluble acrylate-based client hyper-branched polyester,
7 parts of 3- chlorine-2-hydroxyl propyl acrylate Ionization Modification hyperbranched polyethyleneimine, 33 parts of terminal hydroxy group aqueous polyurethane, closing
2 parts of type isocyanate crosslinking, 1.5 parts of PEARLITOL 25C 1,6- bis- (2- isocyano group -3- methyl-2-butene acid esters), fluorine-containing three hydroxyl
0.7 part of base silane class compound, 3 parts of secondary alcohol fatty alcohol polyoxyethylene ether, 0.2 part of sodium peroxydisulfate, 53 parts of water.
Embodiment 3
Embodiment 3 provides a kind of water soluble flocking glue and preparation method thereof, it with it is almost the same in embodiment 1, it is different
It is only a kind of water soluble flocking glue, is made of each raw material of following parts by weight: water-soluble acrylate-based client hyper-branched polyester 25
Part, 7.5 parts of 3- chlorine-2-hydroxyl propyl acrylate Ionization Modification hyperbranched polyethyleneimine, 35 parts of terminal hydroxy group aqueous polyurethane,
3 parts of closed isocyanate crosslinker, 2 parts of PEARLITOL 25C 1,6- bis- (2- isocyano group -3- methyl-2-butene acid esters), fluorine-containing three
0.7 part of silicol class compound, 3.6 parts of castor oil polyoxyethylene ether, 0.3 part of initiator, 55 parts of ammonium persulfate.
Embodiment 4
Embodiment 4 provides a kind of water soluble flocking glue and preparation method thereof, it with it is almost the same in embodiment 1, it is different
It is only a kind of water soluble flocking glue, is made of each raw material of following parts by weight: water-soluble acrylate-based client hyper-branched polyester 28
Part, 9 parts of 3- chlorine-2-hydroxyl propyl acrylate Ionization Modification hyperbranched polyethyleneimine, 38 parts of terminal hydroxy group aqueous polyurethane, envelope
4 parts of closed form isocyanate crosslinking, 2.5 parts of PEARLITOL 25C 1,6- bis- (2- isocyano group -3- methyl-2-butene acid esters), fluorine-containing three
0.9 part of silicol class compound, 4.5 parts of emulsifier, 0.45 part of initiator, 59 parts of water.The emulsifier is dodecyl sulphur
Sour sodium, secondary alcohol fatty alcohol polyoxyethylene ether, castor oil polyoxyethylene ether, alkyl phenol ether sulfosuccinic acid sodium salt 1:1 in mass ratio:
3:2 is mixed.The initiator is potassium peroxydisulfate, sodium peroxydisulfate, ammonium persulfate, azo dicyclohexyl formonitrile HCN hydrochloride are pressed
Mass ratio 1:3:2:2 is mixed.
Embodiment 5
Embodiment 5 provides a kind of water soluble flocking glue and preparation method thereof, it with it is almost the same in embodiment 1, it is different
It is only a kind of water soluble flocking glue, is made of each raw material of following parts by weight: water-soluble acrylate-based client hyper-branched polyester 30
Part, 10 parts of 3- chlorine-2-hydroxyl propyl acrylate Ionization Modification hyperbranched polyethyleneimine, 40 parts of terminal hydroxy group aqueous polyurethane,
5 parts of closed isocyanate crosslinker, 3 parts of PEARLITOL 25C 1,6- bis- (2- isocyano group -3- methyl-2-butene acid esters), fluorine-containing three
1 part of silicol class compound, 5 parts of alkyl phenol ether sulfosuccinic acid sodium salt, 0.5 part of azo dicyclohexyl formonitrile HCN hydrochloride,
60 parts of water.
Comparative example 1
Comparative example 1 provides a kind of water soluble flocking glue and preparation method thereof, it with it is almost the same in embodiment 1, it is different
It is only, without adding water-soluble acrylate-based client hyper-branched polyester in formula.
Comparative example 2
Comparative example 2 provides a kind of water soluble flocking glue and preparation method thereof, it with it is almost the same in embodiment 1, it is different
It is only, without addition 3- chlorine-2-hydroxyl propyl acrylate Ionization Modification hyperbranched polyethyleneimine in formula.
Comparative example 3
Comparative example 3 provides a kind of water soluble flocking glue and preparation method thereof, it with it is almost the same in embodiment 1, it is different
It is only, without addition PEARLITOL 25C 1,6- bis- (2- isocyano group -3- methyl-2-butene acid esters) in formula.
Comparative example 4
Comparative example 4 provides a kind of water soluble flocking glue and preparation method thereof, it with it is almost the same in embodiment 1, it is different
It is only, without adding fluorine-containing ortho-siliformic acid class compound in formula.
Comparative example 5
Comparative example 5 provides a kind of commercially available water-based polyurethane Flock Adhesive.
The technical effect of water soluble flocking glue described in embodiment in order to further illustrate the present invention, will be aqueous in above-mentioned each example
Flock Adhesive coated on 60 DEG C by plant, after solidification, as washing fastness, dry grinding fastness, solvent resistance, flexibility and hand
Sense is tested, and the results are shown in table 1, wherein washing fastness according to GB/T8629-2001, " washed with family by Textile Test
Wash and drying program " tested, wearability detection by GB/T21196-2007 " textile Martindale's method fabric abrasion resistance
Measurement " it is tested.
Performance test table of the table 1 based on water soluble flocking glue in embodiment 1-5, comparative example 1-5
From table 1 it follows that the water soluble flocking glue in embodiment 1-5, which has, is substantially better than the prior art (comparative example 5)
Performance, washing fastness, dry grinding fastness, solvent resistance, flexibility and hand feel performance are more excellent, this is that the collaboration of each ingredient is made
Result.
The above embodiments merely illustrate the technical concept and features of the present invention, and its object is to allow person skilled in the art
Scholar cans understand the content of the present invention and implement it accordingly, and it is not intended to limit the scope of the present invention.It is all according to the present invention
Equivalent change or modification made by Spirit Essence, should be covered by the protection scope of the present invention.
Claims (8)
1. a kind of water soluble flocking glue, which is characterized in that be made of each raw material of following parts by weight: water-soluble acrylate-based client is super
20-30 parts of branched polyester, 5-10 parts of 3- chlorine-2-hydroxyl propyl acrylate Ionization Modification hyperbranched polyethyleneimine, terminal hydroxy group
30-40 parts of aqueous polyurethane, 1-5 parts of the closed isocyanate crosslinker, (2- isocyano group -3- methyl -2- of PEARLITOL 25C 1,6- bis-
Butenoate) 1-3 parts, 0.5-1 parts of fluorine-containing ortho-siliformic acid class compound, 2-5 parts of emulsifier, 0.1-0.5 parts of initiator, water
50-60 parts.
2. water soluble flocking glue according to claim 1, which is characterized in that the emulsifier is lauryl sodium sulfate, secondary alcohol
At least one of fatty alcohol polyoxyethylene ether, castor oil polyoxyethylene ether and alkyl phenol ether sulfosuccinic acid sodium salt.
3. water soluble flocking glue according to claim 1, which is characterized in that the initiator is potassium peroxydisulfate, sodium peroxydisulfate, mistake
At least one of ammonium sulfate, azo dicyclohexyl formonitrile HCN hydrochloride.
4. water soluble flocking glue according to claim 1, which is characterized in that the 3- chlorine-2-hydroxyl propyl acrylate ionization
The preparation method of modified ultra-branching polyethyleneimine includes the following steps: 3- chlorine-2-hydroxyl propyl acrylate, hyperbranched poly
Aziridine is dissolved in n,N-dimethylacetamide, is stirred to react at 60-80 DEG C 4-6 hours, and N, N- diformazan is evaporated off in back spin
Yl acetamide with ether washed product 3-5 times, then is placed at 80-90 DEG C of vacuum oven and dries to constant weight.
5. water soluble flocking glue according to claim 4, which is characterized in that the 3- chlorine-2-hydroxyl propyl acrylate, hyperbranched
Polyethyleneimine, DMAC N,N' dimethyl acetamide mass ratio be 1:1:(8-12).
6. water soluble flocking glue according to claim 1, which is characterized in that the preparation of the fluorine-containing ortho-siliformic acid class compound
Method includes the following steps: to mix trifluoro chlorine Portugal acid, 3- aminopropyl ortho-siliformic acid, is stirred to react 3-5 at 60-80 DEG C
Hour, after 3:1 in mass ratio water and methylene chloride is added, carry out liquid separation, take organic phase, removed water with anhydrous magnesium sulfate, filter, take
Filtrate, revolving remove methylene chloride, obtain fluorine-containing silicol class compound.
7. water soluble flocking glue according to claim 6, which is characterized in that trifluoro chlorine Portugal acid, 3- aminopropyl trihydroxy silicon
The mass ratio of alkane is 1.77:1.
8. any one of -7 water soluble flocking glue according to claim 1, which is characterized in that the preparation side of the water soluble flocking glue
Method includes the following steps:
S1, water and emulsifier are added in emulsifying kettle, the additional amount of water is the 40-50% of total amount, and the additional amount of emulsifier is total
Water-soluble acrylate-based client hyper-branched polyester, 3- chlorine-2-hydroxyl propyl acrylate ion is added in the 80-90% of amount while stirring
Change modified ultra-branching polyethyleneimine, terminal hydroxy group aqueous polyurethane and obtains mixture A after mixing evenly；
S2, the emulsifier of the water of surplus and surplus is added in another emulsifying kettle, enclosed type isocyanide is added while stirring
Acid esters crosslinking agent, PEARLITOL 25C 1,6- bis- (2- isocyano group -3- methyl-2-butene acid esters), fluorine-containing ortho-siliformic acid class compound
And initiator obtains mixture B after mixing evenly；
S3, it is mixed by the mixture A being prepared by step S1 and by the mixture B that step S2 is prepared, stirring is equal
After even, the water soluble flocking glue is obtained.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010197328.2A CN111234758A (en) | 2019-05-13 | 2019-05-13 | Application of water-based flocking adhesive |
| CN201910393723.5A CN110144189B (en) | 2019-05-13 | 2019-05-13 | Water-based flocking adhesive and preparation method thereof |
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| CN201910393723.5A CN110144189B (en) | 2019-05-13 | 2019-05-13 | Water-based flocking adhesive and preparation method thereof |
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| CN110144189B CN110144189B (en) | 2020-06-23 |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN112079982A (en) * | 2020-09-21 | 2020-12-15 | 浙江华峰合成树脂有限公司 | Super-soft protein-imitated hydrolysis-resistant polyurethane resin and preparation method thereof |
| CN112500732A (en) * | 2020-12-22 | 2021-03-16 | 冯国旭 | Weather-resistant exterior wall putty powder and preparation method thereof |
| CN114525098A (en) * | 2022-03-03 | 2022-05-24 | 华威粘结材料（上海）股份有限公司 | Single-component water-based flocking adhesive, flocking member and preparation method of flocking member |
| CN115895540A (en) * | 2022-12-20 | 2023-04-04 | 益丰新材料股份有限公司 | Adhesive composition and application thereof in preparation of recombined wood |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN114539966B (en) * | 2022-04-24 | 2022-07-19 | 苏州市陆氏新材料有限公司 | Heating crosslinking polyurethane adhesive, polyurethane adhesive film and preparation method thereof |
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| JP2011084625A (en) * | 2009-10-14 | 2011-04-28 | Aica Kogyo Co Ltd | Adhesive composition and laminate body |
| CN109439263A (en) * | 2018-12-03 | 2019-03-08 | 苏州市陆氏新材料有限公司 | A kind of preparation method of spary coating type water soluble flocking glue |
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| CN112079982A (en) * | 2020-09-21 | 2020-12-15 | 浙江华峰合成树脂有限公司 | Super-soft protein-imitated hydrolysis-resistant polyurethane resin and preparation method thereof |
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| CN112500732A (en) * | 2020-12-22 | 2021-03-16 | 冯国旭 | Weather-resistant exterior wall putty powder and preparation method thereof |
| CN114525098A (en) * | 2022-03-03 | 2022-05-24 | 华威粘结材料（上海）股份有限公司 | Single-component water-based flocking adhesive, flocking member and preparation method of flocking member |
| CN114525098B (en) * | 2022-03-03 | 2023-09-08 | 华威粘结材料（上海）股份有限公司 | Single-component water-based flocking adhesive, flocking piece and preparation method thereof |
| CN115895540A (en) * | 2022-12-20 | 2023-04-04 | 益丰新材料股份有限公司 | Adhesive composition and application thereof in preparation of recombined wood |
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| CN111234758A (en) | 2020-06-05 |
| CN110144189B (en) | 2020-06-23 |
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