CN105801799A - Application of function polyol to preparation of multifunctional polyurethane - Google Patents
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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
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6666—Compounds of group C08G18/48 or C08G18/52
- C08G18/6696—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/36 or hydroxylated esters of higher fatty acids of C08G18/38
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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
- C08G18/30—Low-molecular-weight compounds
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3819—Low-molecular-weight compounds 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
- C08G18/48—Polyethers
- C08G18/4825—Polyethers containing two hydroxy groups
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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
- C08G2101/00—Manufacture of cellular products
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
The invention provides application of function polyol to preparation of multifunctional polyurethane. Advantages of the research achievement of the research group, namely the industrial scale of 5-chlorine methyl salicylic aldehyde are utilized, the 5-chlorine methyl salicylic aldehyde serves as the raw material and is subjected to a chemical reaction with quaternary ammonium salt of hydroxyl tertiary amine and then subjected to a condensation reaction with bis-primary amine, and the polyol with the molecular structure containing quaternary ammonium positive ions and Salen or Salophen functional groups is obtained and applied to preparation of the multifunctional polyurethane. The function polyol enables the multifunctional polyurethane to have high hydrophilia and water absorption performance, an antibacteria and sterilization function, a rapid cation and anion exchange function, a rapid heavy metal ion absorption function with the saturated absorption time within the level of several minutes and a remarkable color change property generated when the multifunctional polyurethane meets certain heavy metal ions. The multifunctional polyurethane can be used as polymer electrolyte, an ionic conductivity polyurethane membrane, cation and anion exchange resin, an online solid phase extraction material of heavy metal ions, a solid-loaded precious metal catalytic material, a multifunctional polyurethane based gas purification material and a disposable hygiene product.
Description
Technical field
The present invention relates to the application in preparing multifunctional polyurethane of a kind of function polyhydric alcohol, particularly in molecular structure
The application in preparing multifunctional polyurethane of the function polyhydric alcohol containing quaternary ammonium cation and Salen or Salophen part, institute
State multifunctional polyurethane and can be used as disposable sanitary articles, polymer dielectric, ion guide membrane material, cation and anion exchange tree
Fat, zwitterion double extraction polyurethane, immobilized metal catalytic material etc., belong to functional high polymer material field.
Technical background
Polyurethane (Polyurethanes, PUs) is on main chain containing carbamate (-NHCOO-) repetitive
The general name of class macromolecule polyalcohol, it is common that generated with polyisocyanates generation sudden reaction by polyhydric alcohol, belong to the most embedding
Section copolymer；Compared with other macromolecular material, polyurethane material have molecular structure easily design, performance controllable, processability
The characteristics such as energy is good, processing mode is various, mechanical performance is excellent.By polyurethane material being carried out functional modification, thus protecting
While holding polyurethane premium properties, and give the biology of its uniqueness, photoelectromagnetic heat and other physicochemical properties,
Become the main method expanding polyurethane material application.Currently a popular urethane functionalized method has: surface modification
Coating and grafting, blending and modifying, interpenetrating networks, and chemical copolymerization.Wherein by bonding action by functional group and polyurethane
Material carries out the compound of molecular level, not only can give full play to the performance of each component, and have cooperative effect.
Since last century the seventies, 1. those skilled in the art introduce cation in the chain structure of polyurethane,
Such as ammonium, sulfonium base andBase cation, preferably ammonium cation；Or introducing anion, such as sulfonic group or carboxyl so that it is tool
There are hydrophilic, ion exchanging function and antibacterial functions；2. introduce part, such as sulfydryl, aminoacid, adjacent diphenol, 8-hydroxyquinoline,
The construction units such as Schiff's base, benzothiazole and crown ether so that it is there is absorption, enrichment, separation of heavy metal ions function and effect；
3. introducing ionic liquid or Salen part, the research and probe as catalyst etc. never stops.At disclosed literary composition
Offering in data, the raw material that polyurethane carries out functionalization is mainly the N methyldiethanol amine of little molecule, dihydroxypropionic acid, second two
Amine ethyl sulfonic acid, mercaptoethanol, ethoxy imino group ethanedioic acid, double 2,4-4-dihydroxy benzaldehyde contracting ethylenediamine or 8-hydroxyquinoline
Deng；And mainly by the end-blocking of polyurethane prepolymer or chain extension method, introduce in polyurethane material zwitterion or
Some dentates.Thus result in existing urethane functionalized modification and there is limitation and restricted.The function base being firstly introduced into
Limited amount, the functional polyurethane after functionalization is insufficient with effect；Secondly the function of above-mentioned polyurethane does not select with effect
Property；Furthermore the above little molecular changes backbone of original polyurethane macromolecular, have impact on the physical mechanical of polyurethane
Performance.So the most during the last ten years, people are by the research and development field of transfer of attention to polymer polyatomic alcohol functionalization.Specialty
The designed freedom that personnel know polymer polyatomic alcohol molecule is big, so having occurred in that some cationic polymers are polynary
The kinds such as alcohol, anionic polymer polyhydric alcohol, fire resistant polymer polylol or unsaturated polymer polyhydric alcohol.Such as:
CN02815856.3；CN03122339.7；CN201210125277.8；Absorption by Polyurethane Foams:
New Method of Separation, J.Chem.SOC. (A), (1970) 1803-1805；Polymeric and
Immobilized crown compound materials for ion separation, Tetrahedron, 53 (1997)
1343-1360；Click-ligation of coumarin to polyether polyols for polyurethane
Foams, Polym.Int., 62 (2013) 783-790；Detection of uranium with a wireless sensing
method by using salophen as receptor and magnetic nanoparticles as signal-
Amplifying tags, J.Radioanal.Nucl.Chem., 298 (2013) 1393-1399；Polyurethane-based
Cation exchange composite membranes:Preparation, characterization and its
application in development of ion-selective electrode for detection of copper
(II), J.Ind.Eng.Chem., 29 (2015) 392-399 etc..
Salen or Salophen type Schiff's base is two identical aldehyde molecules and the chelating of two amine molecule condensation generations
Schiff's base, has N2O2Four part division centers, easy and metal ion forms planar metal coordination compound.Described Salen or
Salophen metal complex is at catalysis oxidation, catalyzing hydrolysis, Heck coupling, catalytic polymerization, ion blotting and photoelectricity
The fields such as material show its superiority.But Salen or the Salophen metal complex of producing high-molecular is in actual applications
There is again the features such as the recovery easily separated, easy of uniqueness, easy purification, by Salen or Salophen metal complex producing high-molecular
Method has following several ways: (1) organic polymer covalent bond is immobilized, and (2) inorganic polymer covalent bond is immobilized, and (3) are organic high
Molecular coordination bonds is immobilized, the self-polymerization of (4) Salen or Salophen metal complex, (5) other material investment fashion.Example
Such as Recent Advances in Asymmetric C-C and C-heteroatom Bond Forming Reactions
Using Polymer-Bound Catalysts, Adv.Synth.Catal., 345 (2003) 869-929；Schiff Base
Complexes in Macromolecules, J.Inorg.Organometal.Poly.and Mater., 17 (2007) 55-
89；Thermally Latent Reaction of Hemiacetal Ester with Epoxide Catalyzed by
Recyclable Polymeric Catalyst Consisting of Salen-Zinc Complex and
Polyurethane Main Chain, J.Poly.Sci.A:Poly.Chem., 46 (2008) 3673-3681；Polymer-
Supported Schiff base complexes in oxidation reactions, Coord.Chem.Rev., 253
(2009)1926-1946；Metal-salophen-based receptors for anions, Chem.Soc.Rev., 39
(2010)3863-3874；Etc., discuss the progress of Salen or Salophen metal complex producing high-molecular.But by quaternary ammonium
Cation and Salen or Salophen function base are simultaneously introduced in polyurethane material structure so that it is become multi-functional polyurethane
The report of material yet there are no.Based on this, the present inventor utilizes this seminar achievement in research 5-chloromethyl salicylaldehyde commercial scale
Advantage, with 5-chloromethyl salicylaldehyde as raw material, react with the quaternization of hydroxyl tertiary amine, the rear and condensation reaction of di-primary amine,
It is made for molecular structure and contains quaternary ammonium cation and the polyhydric alcohol of Salen or Salophen function base, be applied to multi-functional poly-ammonia
The preparation of ester.
Summary of the invention
The invention provides the application in preparing multifunctional polyurethane of a kind of function polyhydric alcohol, described function polyhydric alcohol energy
When enough giving multifunctional polyurethane strong hydrophilicity water absorption, antibiotic and sterilizing function, quick cation and anion exchange function, saturated absorption
Between at the rapid heavy metal ion adsorption function of several minutes rank and the notable color shifting properties of some heavy metal ion of meeting.
The technical solution used in the present invention is: the application in preparing multifunctional polyurethane of a kind of function polyhydric alcohol, described
Function polyhydric alcohol refers to described in molecular structure containing quaternary ammonium cation and the polyhydric alcohol of Salen or Salophen function base；
A kind of function polyhydric alcohol of the present invention application in preparing multifunctional polyurethane, its application formula is by following
Quality proportioning raw material composition: described function polyhydric alcohol 30～100 parts, commercial polymer polyhydric alcohol 0～100 parts, cross-linking agent 0～
30 parts, polyisocyanates 40～120 parts, organotin 0.2～5.0 parts, organic amine 0.20～5.0 parts, organic foam stabilizer 0
～5 parts, porogen 0～100 parts, foaming agent 0～50 parts, deionized water 0～15 parts；
A kind of function polyhydric alcohol of the present invention application operating program in preparing multifunctional polyurethane is: weigh successively
Described function polyhydric alcohol, commercial polymer polyhydric alcohol, cross-linking agent, porogen and deionized water mix homogeneously, add organotin,
Organic amine and foaming agent, and after being sufficiently stirred for, it is eventually adding organic foam stabilizer and polyisocyanates mix homogeneously, through adding
Poly-course of reaction and maturing process prepare multifunctional polyurethane.
The wherein said polyhydric alcohol containing quaternary ammonium cation and Salen or Salophen function base has formula (A) or logical
Structure shown in formula (B):
R in described formula (A) or formula (B)1And R2Do not choose any or be respectively selected from C1～C18One in alkyl；Selected from C1～C18Alkylene orIn one；X is selected from C2～C10Alkylene,Or the one in aromatic rings, wherein said aromatic rings refers to phenyl ring, pyridine ring, thiphene ring or naphthalene nucleus
In one, described n selected from 1～20 positive integer；M one in 1,2 or 3；
Described commercial polymer polyhydric alcohol refers to commercially available polyether polyol, polybutadiene polyol or PEPA
In one.
Described cross-linking agent refers to glycerol, tetramethylolmethane or 1, the one in 1,1-trimethylolethane.
Described polyisocyanates refer to toluene di-isocyanate(TDI) (TDI), methyl diphenylene diisocyanate (MDI), oneself
Diisocyanate (HDI), isophorone diisocyanate (IPDI), dicyclohexyl methyl hydride diisocyanate (H12MDI), trimethyl
Hexane diisocyanate (TMDI), durol XDI (TMXDI).
Described organotin refers to dibutyltin dilaurate, stannous octoate, stannous oxalate, dialkyl group two maleic acid
One in stannum, two (dodecyl sulfur) dibutyl tins or dibutyltin diacetate.
Described organic amine refer to dimethylethanolamine, DMF, triethylene diamine, dialkylpiperazines,
Alkyl imidazole, 1,8-diazabicyclo [5.4.0] 11 carbon-7-alkene, triethylene diamine carboxylate, dialkylpiperazines carboxylate or
One in alkyl imidazole carboxylate.
Described organic foam stabilizer refers in dimethoxysilane or polyethers-dimethoxysilane copolymer
Kind.
Described porogen refer to oxolane, Isosorbide-5-Nitrae-dioxane, chlorobenzene, boiling range 60～120 DEG C of petroleum ether, hexane,
Hexamethylene, decahydronaphthalene, dimethyl sulfoxide, DMA, dimethyl phthalate, diethyl phthalate, adjacent benzene
One or more in dibutyl carboxylic acid, DMF or N,N-dimethylacetamide
Described foaming agent refer to nitrogen, helium, air, carbon dioxide, dichloromethane, chloroform, fluorochlorohydrocarbon alkane, acetone,
One or more in butane, pentane, hexane, hexamethylene, sodium bicarbonate, lithium bicarbonate or potassium bicarbonate.
Detailed description of the invention
In order to the present invention is further understood, by way of example, it is explained, its object is to
It is more fully understood that present disclosure.Therefore, unlisted in embodiment described one contain quaternary ammonium cation and Salen or
The application in preparing multifunctional polyurethane of the function polyhydric alcohol of Salophen part, is not construed as scope
Limit.
Embodiment 1
Weigh formula (a1The polyhydric alcohol 38 grams containing quaternary ammonium cation and Salophen function base of structure shown in), hydroxyl value
Polyether-tribasic alcohol 62 grams and Isosorbide-5-Nitrae-dioxane 12 grams for 56mgKOH/g, mean molecule quantity are 3000～4000 together mix
Uniformly, rear dibutyltin dilaurate 0.5 gram, triethylene diamine 0.5 gram, pentane 25 grams and the deionized water 4.2 grams of adding, and
It is sufficiently stirred for；Being eventually adding model is AK6618 organic foam stabilizer 1.3 grams and methyl diphenylene diisocyanate 63 grams,
Quickly be uniformly mixed, room temperature foaming in foam box, and ripening 2 hours, prepare Fructus Citri tangerinae color contain quaternary ammonium cation and
The multifunctional polyurethane foamed materials of Salophen function base.
Its Chinese style (a1) containing quaternary ammonium cation and the structural formula of the polyhydric alcohol of Salophen function base:
Performance test: described soft bubble density measurement is carried out according to GB6344-1996 method；Weigh a size of with analytical balance
300 × 300 × 500mm dry state soft bubble sample quality, is accurate to 0.001g, and then calculating soft bubble density is 0.93g/cm3；Inhale
It is that the soft bubble sample of a size of 100 × 100 × 50mm is first placed in the vacuum drying oven that temperature is 50 DEG C drying that water rate measures
6h, accurately weighs its quality, is then placed in normal saline being flooded 10min with electronic balance, takes out, with filter after suctioning water
Paper blots surface water, claims its quality, is accurate to 0.001g, by water absorbent rate=(quality-water suction after water suction before dry mass)/
Dry mass before water suction, calculates normal saline absorbency 121.
Comparative example 1
Weigh hydroxyl value be 56mgKOH/g, mean molecule quantity be 3000～4000 polyether-tribasic alcohol 100 grams and Isosorbide-5-Nitrae-two
22 grams of mix homogeneously of oxygen six ring, add dibutyltin dilaurate 0.8 gram, triethylene diamine 0.8 gram, pentane 25 grams afterwards and go
Ionized water 4.2 grams, and be sufficiently stirred for；Being eventually adding model is AK6618 organic foam stabilizer 1.3 grams and diphenyl methane
Diisocyanate 63 grams, is quickly uniformly mixed, room temperature foaming in foam box, and ripening 2 hours, prepares polyurethane flexible
Foamed materials.Its soft bubble density is 0.85g/cm after measured3；Normal saline absorbance 32.
Integrated embodiment 1 and comparative example 1, it can be seen that a kind of multifunctional polyurethane beneficial effect that the present invention provides
One of be high anti-salt water absorbing capacity.If above-mentioned material is applied in disposable diaper hygienic article, can significantly carry
The high absorption saline inhaling urine core body and all night sexuality, can be greatly lowered High hydrophilous resin in disposable diaper hygienic article
Usage amount, there is significant Social benefit and economic benefit.
Embodiment 2
According to method and the operating procedure of embodiment 1, by the formula (a in embodiment step one1Structure shown in) containing season
The polyhydric alcohol of ammonium cation and Salen function base changes as formula (a2Structure shown in) containing quaternary ammonium cation and Salen function
The polyhydric alcohol of base, prepares containing quaternary ammonium cation and Salen function base function flexible polyurethane foam material, and its density is after measured
0.90g/cm3, normal saline absorbency 126.
Its Chinese style (a2) containing quaternary ammonium cation and the structural formula of Salen function polylol:
Embodiment 3
Weigh formula (a1The polyhydric alcohol 43 grams containing quaternary ammonium cation and Salophen function base of structure shown in), hydroxyl value
For polyether-tribasic alcohol 57 grams that 56mgKOH/g, mean molecule quantity are 3000～4000, Isosorbide-5-Nitrae-dioxane 50 grams, chlorobenzene 50 grams,
Dibutyltin dilaurate 0.5 gram, triethylene diamine 0.5 gram and deionized water 0.8 gram, after being sufficiently stirred for, add toluene two
Isocyanates 56 grams, is quickly uniformly mixed, and in 100 DEG C of ripenings 2 hours, uses washing with alcohol, dried afterwards, prepares shallow
Yellow contains the multifunctional polyurethane porous resin material of quaternary ammonium cation and Salophen function base.
Performance test is with reference to GB/T8144-2008 cation exchange resin exchange capacity assay method, records containing season
The Cu of the multifunctional polyurethane porous resin material of ammonium cation and Salophen function base2+Exchange capacity is 0.2883mmol/
G, its Adsorption of Cu2+After become light green.
Its Chinese style (a1) containing quaternary ammonium cation and the structural formula of the polyhydric alcohol of Salophen function base:
Claims (1)
1. the function polyhydric alcohol application in preparing multifunctional polyurethane, it is characterised in that application formula is by following masses
The raw material composition of proportioning: described function polyhydric alcohol 30～100 parts, commercial polymer polyhydric alcohol 0～100 parts, cross-linking agent 0～30
Part, polyisocyanates 40～120 parts, organotin 0.2～5.0 parts, organic amine 0.2～5.0 parts, organic foam stabilizer 0～5
Part, porogen 0～100 parts, foaming agent 0～50 parts, deionized water 0～15 parts；
According to described raw material composition and quality proportioning, first weigh described function polyhydric alcohol, commercial polymer polyhydric alcohol, cross-linking agent,
Porogen and deionized water mix homogeneously；Add organotin, organic amine, porogen and foaming agent, and after being sufficiently stirred for, finally
Add organic foam stabilizer and polyisocyanates mix homogeneously, prepare through sudden reaction process and maturing process multi-functional poly-
Urethane；
Wherein said function polyhydric alcohol refers in molecular structure containing quaternary ammonium cation and Salen or Salophen function base
Polyhydric alcohol, has a structure shown in formula (A) or formula (B):
R in formula (A) or formula (B)1And R2Do not choose any or be respectively selected from C1～C18One in alkyl；Choosing
From C1～C18Alkylene orIn one；X is selected from C2～C10Alkylene,
Or the one in aromatic rings, wherein said aromatic rings refers to the one in phenyl ring, pyridine ring, thiphene ring or naphthalene nucleus, described n
Selected from the positive integer of 1～20；M one in 1,2 or 3；
Described commercial polymer polyhydric alcohol refers in commercially available polyether polyol, polybutadiene polyol or PEPA
A kind of；
Described cross-linking agent refers to glycerol, tetramethylolmethane or 1, the one in 1,1-trimethylolethane；
Described polyisocyanates refers to toluene di-isocyanate(TDI) (TDI), methyl diphenylene diisocyanate (MDI), oneself is two different
Cyanate (HDI), isophorone diisocyanate (IPDI), dicyclohexyl methyl hydride diisocyanate (H12MDI), trimethyl cyclohexane
Diisocyanate (TMDI), durol XDI (TMXDI)；
Described organotin refer to dibutyltin dilaurate, stannous octoate, stannous oxalate, dialkyl group two maleic acid stannum, two
One in (dodecyl sulfur) dibutyl tin or dibutyltin diacetate；
Described organic amine refers to dimethylethanolamine, DMF, triethylene diamine, dialkylpiperazines, alkyl
Imidazoles, 1,8-diazabicyclo [5.4.0] 11 carbon-7-alkene, triethylene diamine carboxylate, dialkylpiperazines carboxylate or alkyl
One in imidazolyl carboxylic acid salt；
Described organic foam stabilizer refers to the one in dimethoxysilane or polyethers-dimethoxysilane copolymer；
Described porogen refers to oxolane, Isosorbide-5-Nitrae-dioxane, chlorobenzene, boiling range 60～120 DEG C of petroleum ether, hexane, hexamethylenes
Alkane, decahydronaphthalene, dimethyl sulfoxide, DMA, dimethyl phthalate, diethyl phthalate, O-phthalic
One or more in dibutyl phthalate, DMF or N,N-dimethylacetamide；
Described foaming agent refer to nitrogen, helium, air, carbon dioxide, dichloromethane, chloroform, fluorochlorohydrocarbon alkane, acetone, butane,
One or more in pentane, hexane, hexamethylene, sodium bicarbonate, lithium bicarbonate or potassium bicarbonate.
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Cited By (7)
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| CN106397729A (en) * | 2016-08-31 | 2017-02-15 | 佛山林至高分子材料科技有限公司 | Cushioning material capable of being shaped by hot compression as well as preparation method and application of cushioning material |
| CN110573547A (en) * | 2017-05-12 | 2019-12-13 | 株式会社可乐丽 | Chain extender, polyurethane and modification method thereof, polishing layer, polishing pad and polishing method |
| CN112745470A (en) * | 2021-01-14 | 2021-05-04 | 江苏海洋大学 | Application of unsaturated pyridinium inner salt in preparation of blocked polyurethane prepolymer |
| CN112979905A (en) * | 2019-12-13 | 2021-06-18 | 江苏苏博特新材料股份有限公司 | Block polyurethane polymer, polymer modified bentonite admixture thereof, and preparation and application thereof |
| CN114055799A (en) * | 2021-12-13 | 2022-02-18 | 福建恩迈特新材料有限公司 | Material for isolation cabin and preparation method thereof |
| CN116410440A (en) * | 2023-04-03 | 2023-07-11 | 佛山市惠安家居用品有限公司 | Hydrophilic antibacterial sponge and preparation method thereof |
| CN116656002A (en) * | 2023-07-26 | 2023-08-29 | 四川大学 | Low-density high-porosity polyurethane foam material and preparation method thereof |
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