GB856884A - Improvements in the grafting of monomers to hydrogen-containing high-polymeric materials - Google Patents
Improvements in the grafting of monomers to hydrogen-containing high-polymeric materialsInfo
- Publication number
- GB856884A GB856884A GB28387/57A GB2838757A GB856884A GB 856884 A GB856884 A GB 856884A GB 28387/57 A GB28387/57 A GB 28387/57A GB 2838757 A GB2838757 A GB 2838757A GB 856884 A GB856884 A GB 856884A
- Authority
- GB
- United Kingdom
- Prior art keywords
- vinyl
- ultra
- violet light
- polymeric
- acrylamide
- 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
- 239000000463 material Substances 0.000 title abstract 7
- 239000000178 monomer Substances 0.000 title abstract 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 title abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 title abstract 2
- 239000001257 hydrogen Substances 0.000 title abstract 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 4
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 abstract 3
- 239000012190 activator Substances 0.000 abstract 3
- 239000004744 fabric Substances 0.000 abstract 3
- 230000001678 irradiating effect Effects 0.000 abstract 3
- -1 polyethylene Polymers 0.000 abstract 3
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 abstract 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 abstract 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 abstract 2
- 244000043261 Hevea brasiliensis Species 0.000 abstract 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 abstract 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 abstract 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 abstract 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 abstract 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 abstract 2
- 239000012965 benzophenone Substances 0.000 abstract 2
- GVPWHKZIJBODOX-UHFFFAOYSA-N dibenzyl disulfide Chemical compound C=1C=CC=CC=1CSSCC1=CC=CC=C1 GVPWHKZIJBODOX-UHFFFAOYSA-N 0.000 abstract 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 abstract 2
- AWGZKFQMWZYCHF-UHFFFAOYSA-N n-octylprop-2-enamide Chemical compound CCCCCCCCNC(=O)C=C AWGZKFQMWZYCHF-UHFFFAOYSA-N 0.000 abstract 2
- 229920003052 natural elastomer Polymers 0.000 abstract 2
- 229920001194 natural rubber Polymers 0.000 abstract 2
- 229920001778 nylon Polymers 0.000 abstract 2
- 239000011368 organic material Substances 0.000 abstract 2
- 229920001184 polypeptide Polymers 0.000 abstract 2
- 102000004196 processed proteins & peptides Human genes 0.000 abstract 2
- 108090000765 processed proteins & peptides Proteins 0.000 abstract 2
- 239000002023 wood Substances 0.000 abstract 2
- NLNUDODFFAWTHQ-UHFFFAOYSA-N 1-ethenyl-2,3-dihydropyrrole Chemical compound C=CN1CCC=C1 NLNUDODFFAWTHQ-UHFFFAOYSA-N 0.000 abstract 1
- UDJZTGMLYITLIQ-UHFFFAOYSA-N 1-ethenylpyrrolidine Chemical compound C=CN1CCCC1 UDJZTGMLYITLIQ-UHFFFAOYSA-N 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 1
- LEVWYRKDKASIDU-QWWZWVQMSA-N D-cystine Chemical compound OC(=O)[C@H](N)CSSC[C@@H](N)C(O)=O LEVWYRKDKASIDU-QWWZWVQMSA-N 0.000 abstract 1
- 229920000877 Melamine resin Polymers 0.000 abstract 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 abstract 1
- 239000000020 Nitrocellulose Substances 0.000 abstract 1
- 239000004677 Nylon Substances 0.000 abstract 1
- 229920002845 Poly(methacrylic acid) Polymers 0.000 abstract 1
- 239000004698 Polyethylene Substances 0.000 abstract 1
- 229920002367 Polyisobutene Polymers 0.000 abstract 1
- 239000004743 Polypropylene Substances 0.000 abstract 1
- 239000004793 Polystyrene Substances 0.000 abstract 1
- 229920002125 Sokalan® Polymers 0.000 abstract 1
- 229920001807 Urea-formaldehyde Polymers 0.000 abstract 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 abstract 1
- FJWGYAHXMCUOOM-QHOUIDNNSA-N [(2s,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6s)-4,5-dinitrooxy-2-(nitrooxymethyl)-6-[(2r,3r,4s,5r,6s)-4,5,6-trinitrooxy-2-(nitrooxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-3,5-dinitrooxy-6-(nitrooxymethyl)oxan-4-yl] nitrate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O)O[C@H]1[C@@H]([C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@@H](CO[N+]([O-])=O)O1)O[N+]([O-])=O)CO[N+](=O)[O-])[C@@H]1[C@@H](CO[N+]([O-])=O)O[C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O FJWGYAHXMCUOOM-QHOUIDNNSA-N 0.000 abstract 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 abstract 1
- 125000005233 alkylalcohol group Chemical group 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 229920002678 cellulose Polymers 0.000 abstract 1
- 239000001913 cellulose Substances 0.000 abstract 1
- 229920002301 cellulose acetate Polymers 0.000 abstract 1
- 239000011248 coating agent Substances 0.000 abstract 1
- 238000000576 coating method Methods 0.000 abstract 1
- 229960003067 cystine Drugs 0.000 abstract 1
- 239000006185 dispersion Substances 0.000 abstract 1
- 229920001971 elastomer Polymers 0.000 abstract 1
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 abstract 1
- 229920000578 graft copolymer Polymers 0.000 abstract 1
- 230000005660 hydrophilic surface Effects 0.000 abstract 1
- 230000002209 hydrophobic effect Effects 0.000 abstract 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 abstract 1
- 125000005395 methacrylic acid group Chemical class 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 abstract 1
- 229920001220 nitrocellulos Polymers 0.000 abstract 1
- 239000000123 paper Substances 0.000 abstract 1
- 229920001568 phenolic resin Polymers 0.000 abstract 1
- 229920002239 polyacrylonitrile Polymers 0.000 abstract 1
- 229920000570 polyether Polymers 0.000 abstract 1
- 229920000573 polyethylene Polymers 0.000 abstract 1
- 229920000139 polyethylene terephthalate Polymers 0.000 abstract 1
- 239000005020 polyethylene terephthalate Substances 0.000 abstract 1
- 230000000379 polymerizing effect Effects 0.000 abstract 1
- ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 abstract 1
- 229920001155 polypropylene Polymers 0.000 abstract 1
- 229920002223 polystyrene Polymers 0.000 abstract 1
- 229920002689 polyvinyl acetate Polymers 0.000 abstract 1
- 239000011118 polyvinyl acetate Substances 0.000 abstract 1
- 229920000915 polyvinyl chloride Polymers 0.000 abstract 1
- 239000004800 polyvinyl chloride Substances 0.000 abstract 1
- 229920006316 polyvinylpyrrolidine Polymers 0.000 abstract 1
- 239000004627 regenerated cellulose Substances 0.000 abstract 1
- 238000009877 rendering Methods 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 229920003002 synthetic resin Polymers 0.000 abstract 1
- 239000000057 synthetic resin Substances 0.000 abstract 1
- MYVIATVLJGTBFV-UHFFFAOYSA-M thiamine(1+) chloride Chemical compound [Cl-].CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N MYVIATVLJGTBFV-UHFFFAOYSA-M 0.000 abstract 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
- D06M14/18—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials using wave energy or particle radiation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/08—Processes employing the direct application of electric or wave energy, or particle radiation; Apparatus therefor
- B01J19/12—Processes employing the direct application of electric or wave energy, or particle radiation; Apparatus therefor employing electromagnetic waves
- B01J19/122—Incoherent waves
- B01J19/123—Ultraviolet light
-
- 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
- C08F291/00—Macromolecular compounds obtained by polymerising monomers on to macromolecular compounds according to more than one of the groups C08F251/00 - C08F289/00
- C08F291/18—Macromolecular compounds obtained by polymerising monomers on to macromolecular compounds according to more than one of the groups C08F251/00 - C08F289/00 on to irradiated or oxidised macromolecules
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/38—Treatment before imagewise removal, e.g. prebaking
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Toxicology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Electromagnetism (AREA)
- Textile Engineering (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Treatments Of Macromolecular Shaped Articles (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Graft polymers are made by irradiating a hydrogen containing high-molecular weight organic material with ultra violet light having a wavelength of between 170 and 300 millimicrons in the presence of an organic activator, which is capable of absorbing ultra-violet light with a quantum efficiency between 10-2 and unity, for a period of time sufficient to form freeradicals in the polymeric material and simultaneously or subsequently contacting the polymeric material with at least one ethylenically unsaturated organic monomer capable of polymerizing in the presence of free radicals, e.g. acrylonitrile, acrylamide, N-octyl acrylamide, methyl methacrylate, acrylic and methacrylic acids, styrene, vinyl chloride, vinyl acetate, vinyl pyridine, vinyl pyrrolidone, vinyl pyrrolidine and allyl alcohol. Specified polymeric materials are polypeptides (listed), paper, wood, regenerated cellulose, cellulose nitrate and acetate, natural rubber, polyethylene, polypropylene, polyisobutylene, polystyrene, polyacrylonitrile, polyvinyl chloride, polyvinyl acetate, polyvinyl pyrrolidine, polyacrylic and polymethacrylic acids, polyethylene terephthalate, nylons, polyethers, phenol-formaldehyde condensates, melamine condensates and urea-formaldehyde condensates. Activators specified are diphenylamine, benzyl disulphide, acetophenone, benzophenone, acetone, thiamine chloride, alkaline cystine and ninhydrin. The process may be applied to polymeric materials in the form of fibres, films, blocks, &c. whereby desirable surface characteristics may be imparted, e.g. dyeability, moisture affinity and resistance and adhesiveness. Alternatively the polymeric material may be in divided form or in solution or dispersion.ALSO:The tendency of a nylon fabric to accumulate electrostatic charges is reduced by irradiating the fabric, to which benzophenone has been added, with ultra-violet light, and then contacting the fabric with a mixture of vinyl pyridine and vinyl pyrrolidone to provide a graft polymeric coating.ALSO:Tubes, bottles, containers and other shaped objects made from high-polymeric organic materials e.g. polypeptide materials, cellulose and its derivatives, and synthetic resins, are coated by irradiating the object with ultra-violet light in the presence of an activator (see Group IV(a)) and simultaneously or subsequently contacting the irradiated object with an ethylenically unsaturated monomer e.g. acrylamide, acrylonitrile, styrene, methyl methacrylate, vinyl pyrroline, methacrylic acid, vinyl chloride and alkyl alcohol, which graft polymerizes on to the object. In Examples: (6) a slab of natural rubber is coated with an aqueous solution of acrylamide and then irradiated with ultra-violet light thereby producing a hydrophilic surface on the rubber; and (10) a block of wood is coated with N-octylacrylamide and then irradiated with ultra-violet light thereby rendering the surface of the block hydrophobic.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US856884XA | 1956-09-21 | 1956-09-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB856884A true GB856884A (en) | 1960-12-21 |
Family
ID=22193291
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB28387/57A Expired GB856884A (en) | 1956-09-21 | 1957-09-09 | Improvements in the grafting of monomers to hydrogen-containing high-polymeric materials |
Country Status (2)
| Country | Link |
|---|---|
| BE (1) | BE560986A (en) |
| GB (1) | GB856884A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2392411A1 (en) * | 1977-05-23 | 1978-12-22 | Asahi Chemical Ind | METHOD FOR REMOVING THE SURFACE VISCOSITY OF A COMPOSITION OF FREE RADICAL POLYMERIZED RESIN AND HARDENED |
| EP0017032B1 (en) * | 1979-03-12 | 1984-02-15 | Western Electric Company, Incorporated | Method of producing a solid state device by differential plasma etching of resists |
| EP0091651A3 (en) * | 1982-04-12 | 1984-10-17 | Nippon Telegraph And Telephone Public Corporation | Method for forming micropattern |
| EP0328655A4 (en) * | 1987-07-27 | 1989-11-27 | Hitachi Ltd | METHOD OF FORMING MODELS USING A RADIATION - INDUCED GRAFT POLYMERIZATION REACTION. |
| US6225368B1 (en) | 1998-09-15 | 2001-05-01 | National Power Plc | Water based grafting |
| CN119019622A (en) * | 2024-09-11 | 2024-11-26 | 安徽大学 | Preparation of a carbon quantum dot grafted polymer material and its application in photovoltaic adhesive film |
-
0
- BE BE560986D patent/BE560986A/xx unknown
-
1957
- 1957-09-09 GB GB28387/57A patent/GB856884A/en not_active Expired
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2392411A1 (en) * | 1977-05-23 | 1978-12-22 | Asahi Chemical Ind | METHOD FOR REMOVING THE SURFACE VISCOSITY OF A COMPOSITION OF FREE RADICAL POLYMERIZED RESIN AND HARDENED |
| EP0017032B1 (en) * | 1979-03-12 | 1984-02-15 | Western Electric Company, Incorporated | Method of producing a solid state device by differential plasma etching of resists |
| EP0091651A3 (en) * | 1982-04-12 | 1984-10-17 | Nippon Telegraph And Telephone Public Corporation | Method for forming micropattern |
| EP0328655A4 (en) * | 1987-07-27 | 1989-11-27 | Hitachi Ltd | METHOD OF FORMING MODELS USING A RADIATION - INDUCED GRAFT POLYMERIZATION REACTION. |
| US6225368B1 (en) | 1998-09-15 | 2001-05-01 | National Power Plc | Water based grafting |
| US6387964B1 (en) | 1998-09-15 | 2002-05-14 | International Power Plc | Water based grafting |
| CN119019622A (en) * | 2024-09-11 | 2024-11-26 | 安徽大学 | Preparation of a carbon quantum dot grafted polymer material and its application in photovoltaic adhesive film |
Also Published As
| Publication number | Publication date |
|---|---|
| BE560986A (en) |
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