DE2421252C3 - Verfahren zur Herstellung von Zellulosecopolymerisaten - Google Patents
Verfahren zur Herstellung von ZellulosecopolymerisatenInfo
- Publication number
- DE2421252C3 DE2421252C3 DE2421252A DE2421252A DE2421252C3 DE 2421252 C3 DE2421252 C3 DE 2421252C3 DE 2421252 A DE2421252 A DE 2421252A DE 2421252 A DE2421252 A DE 2421252A DE 2421252 C3 DE2421252 C3 DE 2421252C3
- Authority
- DE
- Germany
- Prior art keywords
- cellulose
- weight
- fibers
- solution
- graft
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- 229920002678 cellulose Polymers 0.000 title claims description 61
- 239000001913 cellulose Substances 0.000 title claims description 61
- 238000000034 method Methods 0.000 title claims description 32
- 238000004519 manufacturing process Methods 0.000 title claims description 15
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 25
- 238000007334 copolymerization reaction Methods 0.000 claims description 20
- 239000000178 monomer Substances 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 18
- BGPJLYIFDLICMR-UHFFFAOYSA-N 1,4,2,3-dioxadithiolan-5-one Chemical compound O=C1OSSO1 BGPJLYIFDLICMR-UHFFFAOYSA-N 0.000 claims description 13
- 239000007800 oxidant agent Substances 0.000 claims description 13
- 230000000977 initiatory effect Effects 0.000 claims description 9
- 230000033116 oxidation-reduction process Effects 0.000 claims description 9
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 8
- 229920002554 vinyl polymer Polymers 0.000 claims description 8
- 230000003647 oxidation Effects 0.000 claims description 7
- 238000007254 oxidation reaction Methods 0.000 claims description 7
- 125000003172 aldehyde group Chemical group 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 229910052742 iron Inorganic materials 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 239000012736 aqueous medium Substances 0.000 claims 1
- 159000000014 iron salts Chemical class 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 description 42
- 239000000835 fiber Substances 0.000 description 36
- 239000000243 solution Substances 0.000 description 32
- 229920001519 homopolymer Polymers 0.000 description 26
- 229920000578 graft copolymer Polymers 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 238000003786 synthesis reaction Methods 0.000 description 15
- 229920000297 Rayon Polymers 0.000 description 13
- 239000000463 material Substances 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 7
- 239000007795 chemical reaction product Substances 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- -1 peroxide compounds Chemical class 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 238000000605 extraction Methods 0.000 description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- 229920002239 polyacrylonitrile Polymers 0.000 description 4
- 125000003396 thiol group Chemical group [H]S* 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 150000002191 fatty alcohols Chemical class 0.000 description 3
- 238000010559 graft polymerization reaction Methods 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 150000002978 peroxides Chemical class 0.000 description 3
- 230000001603 reducing effect Effects 0.000 description 3
- 238000007086 side reaction Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical class C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000003421 catalytic decomposition reaction Methods 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- ZOOODBUHSVUZEM-UHFFFAOYSA-N ethoxymethanedithioic acid Chemical compound CCOC(S)=S ZOOODBUHSVUZEM-UHFFFAOYSA-N 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 229920002521 macromolecule Polymers 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
- LGJCFVYMIJLQJO-UHFFFAOYSA-N 1-dodecylperoxydodecane Chemical compound CCCCCCCCCCCCOOCCCCCCCCCCCC LGJCFVYMIJLQJO-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- SFIFMPZUHOERJV-UHFFFAOYSA-N 5-ethenyl-3-ethyl-2-methylpyridine Chemical compound CCC1=CC(C=C)=CN=C1C SFIFMPZUHOERJV-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- 239000004160 Ammonium persulphate Substances 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 102100039845 Guanine nucleotide-binding protein G(I)/G(S)/G(O) subunit gamma-8 Human genes 0.000 description 1
- 101710112841 Guanine nucleotide-binding protein G(I)/G(S)/G(O) subunit gamma-8 Proteins 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 241000872931 Myoporum sandwicense Species 0.000 description 1
- 229920002845 Poly(methacrylic acid) Polymers 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 1
- 235000019395 ammonium persulphate Nutrition 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- HDFRDWFLWVCOGP-UHFFFAOYSA-M sulfanylformate Chemical group [O-]C(S)=O HDFRDWFLWVCOGP-UHFFFAOYSA-M 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 239000012991 xanthate Substances 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M14/00—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials
- D06M14/02—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials on to materials of natural origin
- D06M14/04—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials on to materials of natural origin of vegetal origin, e.g. cellulose or 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
- C08F251/00—Macromolecular compounds obtained by polymerising monomers on to polysaccharides or derivatives thereof
- C08F251/02—Macromolecular compounds obtained by polymerising monomers on to polysaccharides or derivatives thereof on to cellulose or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L87/00—Compositions of unspecified macromolecular compounds, obtained otherwise than by polymerisation reactions only involving unsaturated carbon-to-carbon bonds
- C08L87/005—Block or graft polymers not provided for in groups C08L1/00 - C08L85/04
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/18—Grafting textile fibers
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Artificial Filaments (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Graft Or Block Polymers (AREA)
- Catalysts (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT352474A AT336272B (de) | 1974-04-29 | 1974-04-29 | Verfahren zur herstellung von cellulosecopolymerisaten |
| DE2421252A DE2421252C3 (de) | 1974-04-29 | 1974-05-02 | Verfahren zur Herstellung von Zellulosecopolymerisaten |
| FR7416475A FR2271234B1 (enExample) | 1974-04-29 | 1974-05-13 | |
| GB2118974A GB1459310A (en) | 1974-04-29 | 1974-05-14 | Method for preparing cellu |
| US472202A US3878144A (en) | 1974-04-29 | 1974-05-21 | Method for preparing cellulose graft copolymers utilizing tervalent iron initiator |
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT352474A AT336272B (de) | 1974-04-29 | 1974-04-29 | Verfahren zur herstellung von cellulosecopolymerisaten |
| DE2421252A DE2421252C3 (de) | 1974-04-29 | 1974-05-02 | Verfahren zur Herstellung von Zellulosecopolymerisaten |
| FR7416475A FR2271234B1 (enExample) | 1974-04-29 | 1974-05-13 | |
| GB2118974A GB1459310A (en) | 1974-04-29 | 1974-05-14 | Method for preparing cellu |
| US472202A US3878144A (en) | 1974-04-29 | 1974-05-21 | Method for preparing cellulose graft copolymers utilizing tervalent iron initiator |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2421252A1 DE2421252A1 (de) | 1975-11-13 |
| DE2421252B2 DE2421252B2 (de) | 1979-05-17 |
| DE2421252C3 true DE2421252C3 (de) | 1980-01-17 |
Family
ID=27506378
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2421252A Expired DE2421252C3 (de) | 1974-04-29 | 1974-05-02 | Verfahren zur Herstellung von Zellulosecopolymerisaten |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3878144A (enExample) |
| AT (1) | AT336272B (enExample) |
| DE (1) | DE2421252C3 (enExample) |
| FR (1) | FR2271234B1 (enExample) |
| GB (1) | GB1459310A (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20070255355A1 (en) * | 2006-04-06 | 2007-11-01 | Palomar Medical Technologies, Inc. | Apparatus and method for skin treatment with compression and decompression |
| DE102014220289B4 (de) * | 2014-10-07 | 2016-12-29 | Bundesdruckerei Gmbh | Verfahren zur Herstellung von modifizierter Regeneratcellulose und deren Verwendung |
| CN112537989B (zh) * | 2020-11-10 | 2022-07-15 | 衡水市中禾谷盐碱地生态研究所 | 一种木质素生物质树脂基盐碱地改良剂的制备方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3008920A (en) * | 1959-04-27 | 1961-11-14 | Dow Chemical Co | Method of inhibiting homopolymerization in graft copolymers with copper salts |
| NL132533C (enExample) * | 1962-09-24 | |||
| US3330787A (en) * | 1963-04-08 | 1967-07-11 | Scott Paper Co | Graft polymerization using ferrated thioated cellulose substrate, products thereof and intermediates |
| US3821137A (en) * | 1970-06-22 | 1974-06-28 | M Ferberg | Graft copolymers of cellulose and polyacrylthioamide, method of theirproduction and application |
-
1974
- 1974-04-29 AT AT352474A patent/AT336272B/de not_active IP Right Cessation
- 1974-05-02 DE DE2421252A patent/DE2421252C3/de not_active Expired
- 1974-05-13 FR FR7416475A patent/FR2271234B1/fr not_active Expired
- 1974-05-14 GB GB2118974A patent/GB1459310A/en not_active Expired
- 1974-05-21 US US472202A patent/US3878144A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| FR2271234B1 (enExample) | 1977-03-11 |
| US3878144A (en) | 1975-04-15 |
| DE2421252A1 (de) | 1975-11-13 |
| DE2421252B2 (de) | 1979-05-17 |
| AT336272B (de) | 1977-04-25 |
| ATA352474A (de) | 1976-08-15 |
| GB1459310A (en) | 1976-12-22 |
| FR2271234A1 (enExample) | 1975-12-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8328 | Change in the person/name/address of the agent |
Free format text: VON FUENER, A., DIPL.-CHEM. DR.RER.NAT. EBBINGHAUS, D., DIPL.-ING., PAT.-ANW., 8000 MUENCHEN |
|
| 8339 | Ceased/non-payment of the annual fee |