WO2007149045B1 - Copolymer, modified polymer carbohydrate material, modified buld polymer, composite material, and methods of preparation - Google Patents

Copolymer, modified polymer carbohydrate material, modified buld polymer, composite material, and methods of preparation

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Publication number
WO2007149045B1
WO2007149045B1 PCT/SE2007/050450 SE2007050450W WO2007149045B1 WO 2007149045 B1 WO2007149045 B1 WO 2007149045B1 SE 2007050450 W SE2007050450 W SE 2007050450W WO 2007149045 B1 WO2007149045 B1 WO 2007149045B1
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WO
WIPO (PCT)
Prior art keywords
copolymer
xyloglucan
macromolecule
polymer
hydrophobic
Prior art date
Application number
PCT/SE2007/050450
Other languages
French (fr)
Other versions
WO2007149045A1 (en
Inventor
Qi Zhou
Harry Brumer
Tuula Tellervo Teeri
Johan Patrik Stolt
Lars Goeran Oedberg
Original Assignee
Swetree Technologies Ab
Qi Zhou
Harry Brumer
Tuula Tellervo Teeri
Johan Patrik Stolt
Lars Goeran Oedberg
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Swetree Technologies Ab, Qi Zhou, Harry Brumer, Tuula Tellervo Teeri, Johan Patrik Stolt, Lars Goeran Oedberg filed Critical Swetree Technologies Ab
Publication of WO2007149045A1 publication Critical patent/WO2007149045A1/en
Publication of WO2007149045B1 publication Critical patent/WO2007149045B1/en

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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
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/66—Polyesters containing oxygen in the form of ether groups
    • C08G63/664—Polyesters containing oxygen in the form of ether groups derived from hydroxy carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
    • C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
    • C08B37/0057—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid beta-D-Xylans, i.e. xylosaccharide, e.g. arabinoxylan, arabinofuronan, pentosans; (beta-1,3)(beta-1,4)-D-Xylans, e.g. rhodymenans; Hemicellulose; Derivatives thereof
    • 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
    • C08F293/00—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule
    • C08F293/005—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule using free radical "living" or "controlled" polymerisation, e.g. using a complexing agent
    • 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
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
    • 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
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
    • C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
    • C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
    • C08G61/124—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds with a five-membered ring containing one nitrogen atom in the ring
    • 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
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
    • C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
    • C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
    • C08G61/126—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds with a five-membered ring containing one sulfur atom in the ring
    • 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
    • C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
    • C08G64/18—Block or graft polymers
    • 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
    • C08G81/00—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers
    • C08G81/02—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers at least one of the polymers being obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • C08G81/021—Block or graft polymers containing only sequences of polymers of C08C or C08F
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L65/00—Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Compositions of derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P19/00—Preparation of compounds containing saccharide radicals
    • C12P19/04—Polysaccharides, i.e. compounds containing more than five saccharide radicals attached to each other by glycosidic bonds
    • 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
    • C08F2438/00—Living radical polymerisation
    • C08F2438/01—Atom Transfer Radical Polymerization [ATRP] or reverse ATRP
    • 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
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/10—Definition of the polymer structure
    • C08G2261/12—Copolymers
    • C08G2261/126—Copolymers block
    • 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
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/31—Monomer units or repeat units incorporating structural elements in the main chain incorporating aromatic structural elements in the main chain
    • C08G2261/314—Condensed aromatic systems, e.g. perylene, anthracene or pyrene
    • C08G2261/3142—Condensed aromatic systems, e.g. perylene, anthracene or pyrene fluorene-based, e.g. fluorene, indenofluorene, or spirobifluorene
    • 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
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/32—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain
    • C08G2261/322—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed
    • C08G2261/3221—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed containing one or more nitrogen atoms as the only heteroatom, e.g. pyrrole, pyridine or triazole
    • 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
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/32—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain
    • C08G2261/322—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed
    • C08G2261/3223—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed containing one or more sulfur atoms as the only heteroatom, e.g. thiophene
    • 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
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/34—Monomer units or repeat units incorporating structural elements in the main chain incorporating partially-aromatic structural elements in the main chain
    • C08G2261/342—Monomer units or repeat units incorporating structural elements in the main chain incorporating partially-aromatic structural elements in the main chain containing only carbon atoms
    • C08G2261/3422—Monomer units or repeat units incorporating structural elements in the main chain incorporating partially-aromatic structural elements in the main chain containing only carbon atoms conjugated, e.g. PPV-type
    • 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
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/50—Physical properties
    • C08G2261/51—Charge transport
    • C08G2261/514—Electron transport

Abstract

The present invention relates to a novel group of copolymers comprising a soluble carbohydrate polymer (SCP), which typically is a non-starch carbohydrate, and a macromolecule covalently attached to the SCP. The macromolecule may e.g. be a hydrophobic copolymer, a polyelectrolyte polymer or a biodegradable polymer. The present invention furthermore relates to a method of preparing the copolymer, products comprising the copolymer, and to methods of preparing the products comprising the copolymer. The products comprising a copolymer are for example a polymeric carbohydrate material (PCM) modified by attachment of a copolymer, and a composite material comprising the modified PCM.

Claims

69AMENDED CLAIMS received by the International Bureau on 26 November 2007(26.11.2007)
1. Use of a copolymer comprising a xyloglucan and a macromolecule covalently attached to the xyloglucan for modifying a polymeric carbohydrate material, especially cellulose.
2. The use according to claim 1, wherein the macromolecule comprises a hydrophobic polymer.
3. The use according to any of claims 1-2, wherein the macromolecule comprises a biodegradable polymer.
4. The use according to any of the preceding claims wherein the macromolecule comprises an electrically conducting polymer polymer, which may be chosen from poly(acetylene)s, poly(pyrrole)s, poly(thiophene)s, poly(aniline)s, poly(fluorene)s, polynaphthalenes, poly(p- phenylene sulfide), and poly(para-phenylene vinylene)s.
5. The use according to any of the preceding claims wherein the macromolecule comprises a signal-responsive polymer.
6. The use according to any of the preceding claims, wherein the copolymer is a block copolymer.
7. The use according to any of the claims 1-6, wherein the copolymer is a dendrimer comprising: a branched macromolecule having at least 3 end groups, and at least one xyloglucan covalently attached to one of the at least 3 end groups of the branched macromolecule.
8. The use according to any of the preceding claims comprising in the range of 1-500 xyloglucans covalently attached to the macromolecule.
9. An aqueous formulation of the copolymer according to any of the preceding claims, wherein the aqueous formulation comprises copolymer in an amount in the range of 0.1-80% by weight, and water in an amount in the range of 20-99.9% by weight.
10. The aqueous formulation according to claim 9, furthermore comprising an organic, water soluble solvent, such as in an amount in the range of 5-45% by weight. 70
11. The aqueous formulation according to any of the claims 9-10, wherein the organic, water soluble solvent comprises an alcohol, acetone, propylene glycol, or glycerol, or a mixture thereof
12. The aqueous formulation according to any of the claims 9-11, furthermore comprising an emulsifier such as in an amount in the range of 0.1-10% by weight.
13. A hydrophobic formulation of the copolymer according to any of the claims 1-8, wherein the hydrophobic formulation comprises copolymer in an amount in the range of 0.1-80% by weight, and a hydrophobic solvent in an amount in the range of 20-99.9% by weight.
14. A dry formulation of the copolymer according to any of the claims 1-8, wherein the dry formulation comprises copolymer in an amount in the range of 5-99.9% by weight, and water in an amount in the range of 0.1-10% by weight, preferably in the range of 0.1-5% by weight, and even more preferably in the range of 0.1-2% by weight.
15. The dry formulation according to claim 10, furthermore comprising a wetting agent, and/or a humectant, and/or an anti-agglomeration agent
16. A method of preparing a copolymer according to any of the preceding claims, the method comprising the steps of a) providing an xyloglucan and a macromolecule, and b) attaching the macromolecule covalently to the X xyloglucan. wherein step b) may involve one or more processes selected from the group consisting of: - reacting the xyloglucan with galactose oxidase;
- reacting the xyloglucan with an oxidizing agent,
- oxidizing of a primary alcohol group to obtain an aldehyde group; and
- reacting an aldehyde group with a primary amino group.
17. The method according to claim 16, wherein step b) involves reductive amination of the xyloglucan, wherein the xyloglucan may comprise an amino group and wherein the macromolecule, such as the hydrophobic polymer, may comprise an aldehyde group, and step b) involves reacting the aldehyde group with the amino group or wherein xyloglucan comprises an aldehyde group and the macromolecule comprises an amino group, and step b) involves reacting the aldehyde group with the amino group.
18. The method according to any of the claims 16-17, wherein the macromolecule comprises an aldehyde group and step b) involves reacting a xyloglucan with a diamine compound and a reducing agent to obtain an aminated xyloglucan and to react the aminated xyloglucan with macromolecule comprising the aldehyde group to obtain the copolymer. 71
19. The method according to claim 18, wherein the reducing agent is a salt of cyanoborohydride.
20. A method of preparing a copolymer according to any of the preceding claims, the method comprising the steps of a) providing an xyloglucan, b) attaching covalently a polymerisation initiator to the xyloglucan, wherein at least 2 polymerisation initiators may be attached to the xyloglucan or wherein the polymerisation initiator may be selected from the group consisting of an acid-containing initiator, an allyl bromide, an allyl chloride, and a phenolic ester based monofunctional initiators, c) polymerising onto the xyloglucan via the polymerisation initiator.
21. A modified polymeric carbohydrate material (PCM) comprising a copolymer according to any of the claims 1-8, wherein the weight ratio between copolymer and PCM is in the range of
100: 1 - 1: 100, such as in the range of 100: 1 - 1: 1, e.g. in the range of 1: 1 - 1: 100.
22. A method of preparing a modified hydrophobic bulk polymer, the method comprising the steps of
1) providing a copolymer according to any of the preceding claims ..., said copolymer comprising an xyloglucan and a hydrophobic polymer,
2) binding the copolymer to a hydrophobic bulk polymer under suitable conditions, thus obtaining the modified hydrophobic bulk polymer.
23. A modified hydrophobic bulk polymer comprising a hydrophobic bulk polymer and a copolymer according to any of the claims 1-8, wherein the weight ratio between copolymer and hydrophobic bulk polymer may be in the range of 10: 1 - 1: 1000.
24. A method of preparing a composite material comprising a hydrophobic bulk polymer and PCM, the method comprising the steps of: i) providing a hydrophobic bulk polymer and a modified PCM according to claim 21 and ii) mixing the hydrophobic bulk polymer and the modified PCM.
25. A method of preparing a composite material comprising a hydrophobic bulk polymer and PCM, the method comprising the steps of: i) providing a PCM and a modified hydrophobic bulk polymer according to claim 23,
ii) mixing the modified hydrophobic bulk polymer and the PCM. 72
26. A method of preparing a composite material comprising a hydrophobic bulk polymer and PCM, the method comprising the steps of: i) providing a PCM, a hydrophobic bulk polymer, and a copolymer according to any of claims 1-8,
ii) mixing the modified hydrophobic bulk polymer and the PCM.
27. A composite material comprising a PCM and the modified hydrophobic bulk polymer according to claim 23 or obtainable by a method according to any of the claims 24-26.
28. Use of the copolymer according to any of the claims 1-8 as a compatibiliser, whereby the at least one macromolecule of the copolymer may be a hydrophobic polymer.
29. A copolymer comprising a xyloglucan and a macromolecule covalently attached to the xyloglucan, wherein the macromolecule comprises an electrically conducting polymer.
30. A copolymer comprising a xyloglucan and a macromolecule covalently attached to the xyloglucan, wherein the copolymer is a dendrimer comprising: a branched macromolecule having at least 3 end groups, and at least one SCP covalently attached to one of the at least 3 end groups of the branched macromolecule.
PCT/SE2007/050450 2006-06-23 2007-06-21 Copolymer, modified polymer carbohydrate material, modified buld polymer, composite material, and methods of preparation WO2007149045A1 (en)

Applications Claiming Priority (2)

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PCT/EP2006/006099 WO2007147428A1 (en) 2006-06-23 2006-06-23 Copolymer, modified polymer carbohydrate material, modified bulk polymer, composite material, and methods of preparation

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EP2435485B1 (en) * 2009-05-27 2019-01-09 Cellutech AB A polymer made of a primary amine functionalized polymer and a hemicellulose
GB0916031D0 (en) * 2009-09-14 2009-10-28 Univ Nottingham Cellulose nanoparticle aerogels,hydrogels and organogels
US20140235790A1 (en) * 2011-06-10 2014-08-21 University Of Washington Through Its Center For Commercialization Carbohydrate-based compositions and methods for targeted drug delivery
US8815054B2 (en) 2012-10-05 2014-08-26 The Procter & Gamble Company Methods for making fibrous paper structures utilizing waterborne shape memory polymers
CN103965516A (en) * 2013-02-01 2014-08-06 上海杰事杰新材料(集团)股份有限公司 Fully biodegradable masterbatch and preparation method thereof
CN106062276B (en) * 2014-03-05 2019-06-11 诺维信公司 For by material functional and the composition being attached and method
CN107096399A (en) * 2016-02-22 2017-08-29 深圳市启德环保科技有限公司 A kind of high pressure resistant porous polymer PMMA filter membrane materials
CN108622871B (en) * 2017-03-17 2021-05-07 南开大学 Preparation method of carbon aerogel by using polyaniline as cross-linking agent
CN108622991B (en) * 2017-03-17 2021-05-07 南开大学 Method for degrading organic wastewater by catalyzing persulfate through nitrogen-doped carbon aerogel
CN107189006B (en) * 2017-06-23 2020-03-31 江苏锐康新材料科技有限公司 Acrylate resin shape memory intelligent material and preparation method and application thereof
CN107700214B (en) * 2017-10-24 2019-12-24 广东德美精细化工集团股份有限公司 Efficient fluorine-free water repellent containing telechelic polymer and preparation method thereof
CN108383917B (en) * 2018-01-30 2020-06-05 浙江理工大学 Multifunctional cellulose membrane and preparation method thereof
CN108410012B (en) * 2018-03-15 2020-04-07 西南大学 Efficient flame-retardant nano synergist and preparation method and application thereof
CN108929414A (en) * 2018-09-04 2018-12-04 济南大学 A kind of preparation and application of hyperbranched type modified starch water-reducing agent

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EP1860121A3 (en) * 2001-10-16 2008-12-03 Swetree Technologies Ab Method for the modification of polymeric carbohydrate materials

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