GB899567A - Graft copolymers from olefinically unsaturated monomers and polycondensates and a process for their production - Google Patents
Graft copolymers from olefinically unsaturated monomers and polycondensates and a process for their productionInfo
- Publication number
- GB899567A GB899567A GB47961A GB47961A GB899567A GB 899567 A GB899567 A GB 899567A GB 47961 A GB47961 A GB 47961A GB 47961 A GB47961 A GB 47961A GB 899567 A GB899567 A GB 899567A
- Authority
- GB
- United Kingdom
- Prior art keywords
- vinyl
- styrene
- polycondensates
- nitrosated
- acrylonitrile
- 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
- 239000000178 monomer Substances 0.000 title abstract 4
- 229920000578 graft copolymer Polymers 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 10
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 abstract 4
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 abstract 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 abstract 4
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 abstract 3
- 238000006243 chemical reaction Methods 0.000 abstract 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 abstract 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 abstract 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 abstract 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 abstract 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 abstract 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 abstract 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 abstract 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 abstract 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 abstract 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 abstract 2
- 239000003513 alkali Substances 0.000 abstract 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 abstract 2
- LZDSILRDTDCIQT-UHFFFAOYSA-N dinitrogen trioxide Chemical compound [O-][N+](=O)N=O LZDSILRDTDCIQT-UHFFFAOYSA-N 0.000 abstract 2
- 239000006185 dispersion Substances 0.000 abstract 2
- 238000010559 graft polymerization reaction Methods 0.000 abstract 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract 2
- LGXVIGDEPROXKC-UHFFFAOYSA-N 1,1-dichloroethene Chemical class ClC(Cl)=C LGXVIGDEPROXKC-UHFFFAOYSA-N 0.000 abstract 1
- OZCMOJQQLBXBKI-UHFFFAOYSA-N 1-ethenoxy-2-methylpropane Chemical compound CC(C)COC=C OZCMOJQQLBXBKI-UHFFFAOYSA-N 0.000 abstract 1
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 abstract 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 abstract 1
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 abstract 1
- 239000004342 Benzoyl peroxide Substances 0.000 abstract 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 abstract 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 abstract 1
- 239000004157 Nitrosyl chloride Substances 0.000 abstract 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 abstract 1
- 229920002292 Nylon 6 Polymers 0.000 abstract 1
- 229920002396 Polyurea Polymers 0.000 abstract 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 abstract 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- -1 alkyl nitrites Chemical class 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 235000019400 benzoyl peroxide Nutrition 0.000 abstract 1
- ISJUTWWVTHSEQT-UHFFFAOYSA-N butane-1,4-diol;carbonyl dichloride Chemical compound ClC(Cl)=O.OCCCCO ISJUTWWVTHSEQT-UHFFFAOYSA-N 0.000 abstract 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 abstract 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 abstract 1
- CJSBUWDGPXGFGA-UHFFFAOYSA-N dimethyl-butadiene Natural products CC(C)=CC=C CJSBUWDGPXGFGA-UHFFFAOYSA-N 0.000 abstract 1
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 abstract 1
- 230000005284 excitation Effects 0.000 abstract 1
- 229910001385 heavy metal Inorganic materials 0.000 abstract 1
- 150000004679 hydroxides Chemical class 0.000 abstract 1
- 125000005395 methacrylic acid group Chemical class 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical compound C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 abstract 1
- 150000002825 nitriles Chemical class 0.000 abstract 1
- VPCDQGACGWYTMC-UHFFFAOYSA-N nitrosyl chloride Chemical compound ClN=O VPCDQGACGWYTMC-UHFFFAOYSA-N 0.000 abstract 1
- 235000019392 nitrosyl chloride Nutrition 0.000 abstract 1
- RYFZYYUIAZYQLC-UHFFFAOYSA-N perchloromethyl mercaptan Chemical compound ClSC(Cl)(Cl)Cl RYFZYYUIAZYQLC-UHFFFAOYSA-N 0.000 abstract 1
- 229920006149 polyester-amide block copolymer Polymers 0.000 abstract 1
- 238000006116 polymerization reaction Methods 0.000 abstract 1
- 229920002635 polyurethane Polymers 0.000 abstract 1
- 239000004814 polyurethane Substances 0.000 abstract 1
- 239000000843 powder Substances 0.000 abstract 1
- QROGIFZRVHSFLM-UHFFFAOYSA-N prop-1-enylbenzene Chemical class CC=CC1=CC=CC=C1 QROGIFZRVHSFLM-UHFFFAOYSA-N 0.000 abstract 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 229920001567 vinyl ester resin Polymers 0.000 abstract 1
- 229920002554 vinyl polymer Polymers 0.000 abstract 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical class OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- 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
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/04—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polycarbonamides, polyesteramides or polyimides
-
- 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
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Graft Or Block Polymers (AREA)
- Paints Or Removers (AREA)
Abstract
Graft polymers are formed by a process in which a polycondensate containing -CONHgroups is nitrosated at some or all of the amide nitrogen atoms and the resulting N-nitrosopolycondensate is copolymerized with one or more olefinically unsaturated monomers, e.g. acrylic and methacrylic acids and their C1-C12 esters, nitriles and amides, styrene, methylstyrenes, divinylbenzene, isobutylene, vinyl esters with C2-C18 acids, vinyl and vinylidene chlorides, butadiene, chloroprene, isoprene, dimethylbutadiene, vinyl ethers of C1-C12 alcohols, vinyl sulphonic acids, and vinyl pyridine, imidazole, pyrrolidone and carbazole. Polycondensates speeified are polycaprolactam, condensates of hexamethylene diamine with adipic or sebacic acid, a condensate of sebacic acid with p,p1diamino-diphenylmethane, a polyurethane prepared from a mixture of hexamethylene diamine and 1,4-butanediol dichlorocarbonate, and also polyesteramides, polyureas and polythioureas. The polycondensates are nitrosated by treatment with nitrosating agents such as dinitrogen trioxide, nitrosyl chloride, nitrous acid or alkyl nitrites, the reaction being carried out with the polycondensate in powder form or in solution, dispersion or in swollen form. In one mode of operation the polycondensate is nitrosated whilst dissolved, swollen or dispersed in the olefincally unsaturated monomer, in which case graft polymerization occurs simultaneously if the temperature of the reaction is in excess of room temperature. The graft polymerization of the unsaturated monomer may be accelerated by means of catalysts such as alkali and alkaline earth hydroxides, alkali carbonates, amines, heavy metal salts, benzoyl peroxide and, when employing photochemical excitation of the reaction, azobisisobutyronitrile, anthracene or perchloromethyl mercaptan. The polymerization may be carried out in bulk, solution or dispersion. The examples describe the production of graft polymers from nitrosated polycondensates with: (1) and (2) vinyl acetate+ acrylic acid, (3) acrylonitrile, (4) acrylonitrile+ styrene, (5) acrylonitrile, (6) and (7) methyl methacrylate, (8) methyl methacrylate+vinyl acetate, (9) butyl acrylate+vinyl pyrrolidone, (10) styrene, (11) styrene+isoprene or isobutylene, (12) vinyl chloride+vinyl carbazole, (13) vinyl propionate+vinyl isobutyl ether and (15) styrene.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB56153A DE1138934B (en) | 1960-01-07 | 1960-01-07 | Process for the production of graft copolymers from olefinically unsaturated monomers and polycondensates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB899567A true GB899567A (en) | 1962-06-27 |
Family
ID=6971236
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB47961A Expired GB899567A (en) | 1960-01-07 | 1961-01-05 | Graft copolymers from olefinically unsaturated monomers and polycondensates and a process for their production |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE598869A (en) |
| DE (1) | DE1138934B (en) |
| FR (1) | FR1277263A (en) |
| GB (1) | GB899567A (en) |
| NL (1) | NL259698A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3334153A (en) * | 1964-06-11 | 1967-08-01 | Kurashiki Rayon Co | Mixture of polyamide, polystyrene, and polyamide-styrene graft copolymer |
| US4378448A (en) | 1979-10-20 | 1983-03-29 | Raychem Corporation | Polyamide graft as hot-melt adhesive, and elastomer blend |
| WO2002053620A3 (en) * | 2000-12-31 | 2003-01-16 | Basf Corp | Method of making a graft polymer |
| WO2006106138A1 (en) * | 2005-04-07 | 2006-10-12 | Basf Aktiengesellschaft | Method for producing an aqueous polymer dispersion |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE558898A (en) * | ||||
| BE558899A (en) * |
-
0
- NL NL259698D patent/NL259698A/xx unknown
- BE BE598869D patent/BE598869A/xx unknown
-
1960
- 1960-01-07 DE DEB56153A patent/DE1138934B/en active Pending
-
1961
- 1961-01-05 GB GB47961A patent/GB899567A/en not_active Expired
- 1961-01-06 FR FR849002A patent/FR1277263A/en not_active Expired
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3334153A (en) * | 1964-06-11 | 1967-08-01 | Kurashiki Rayon Co | Mixture of polyamide, polystyrene, and polyamide-styrene graft copolymer |
| US4378448A (en) | 1979-10-20 | 1983-03-29 | Raychem Corporation | Polyamide graft as hot-melt adhesive, and elastomer blend |
| WO2002053620A3 (en) * | 2000-12-31 | 2003-01-16 | Basf Corp | Method of making a graft polymer |
| US6639016B2 (en) | 2000-12-31 | 2003-10-28 | Basf Corporation | Method of making a graft polymer |
| WO2006106138A1 (en) * | 2005-04-07 | 2006-10-12 | Basf Aktiengesellschaft | Method for producing an aqueous polymer dispersion |
Also Published As
| Publication number | Publication date |
|---|---|
| BE598869A (en) | |
| NL259698A (en) | |
| FR1277263A (en) | 1961-11-24 |
| DE1138934B (en) | 1962-10-31 |
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