CA1080879A - High impact polyamides - Google Patents
High impact polyamidesInfo
- Publication number
- CA1080879A CA1080879A CA253,105A CA253105A CA1080879A CA 1080879 A CA1080879 A CA 1080879A CA 253105 A CA253105 A CA 253105A CA 1080879 A CA1080879 A CA 1080879A
- Authority
- CA
- Canada
- Prior art keywords
- composition
- mixture
- polyamide
- fat acid
- acid
- 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
- 239000004952 Polyamide Substances 0.000 title claims abstract description 44
- 229920002647 polyamide Polymers 0.000 title claims abstract description 44
- 239000000203 mixture Substances 0.000 claims abstract description 58
- 239000002253 acid Substances 0.000 claims abstract description 51
- 229920000642 polymer Polymers 0.000 claims abstract description 47
- 150000001993 dienes Chemical class 0.000 claims abstract description 29
- 239000000178 monomer Substances 0.000 claims abstract description 26
- 125000000524 functional group Chemical group 0.000 claims abstract description 4
- 235000019197 fats Nutrition 0.000 claims description 29
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical group O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 claims description 18
- 150000004985 diamines Chemical class 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims description 5
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 4
- 150000003951 lactams Chemical class 0.000 claims description 4
- 229920002857 polybutadiene Polymers 0.000 claims description 4
- 239000005062 Polybutadiene Substances 0.000 claims description 3
- 150000003863 ammonium salts Chemical class 0.000 claims description 3
- 235000020778 linoleic acid Nutrition 0.000 claims description 3
- OYHQOLUKZRVURQ-HZJYTTRNSA-N linoleic acid group Chemical group C(CCCCCCC\C=C/C\C=C/CCCCC)(=O)O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 claims description 3
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 3
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims 2
- 235000021313 oleic acid Nutrition 0.000 claims 2
- 235000011037 adipic acid Nutrition 0.000 claims 1
- 239000001361 adipic acid Substances 0.000 claims 1
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 9
- 238000000465 moulding Methods 0.000 abstract description 4
- 238000001125 extrusion Methods 0.000 abstract description 3
- 229920006122 polyamide resin Polymers 0.000 abstract description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000000539 dimer Substances 0.000 description 9
- 238000000034 method Methods 0.000 description 8
- 229920002292 Nylon 6 Polymers 0.000 description 7
- 238000006116 polymerization reaction Methods 0.000 description 7
- 150000007513 acids Chemical class 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 239000004615 ingredient Substances 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- -1 polyhexa-methylene Polymers 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 229920001519 homopolymer Polymers 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- 229920002302 Nylon 6,6 Polymers 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 3
- 229940100630 metacresol Drugs 0.000 description 3
- 239000003607 modifier Substances 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 238000012643 polycondensation polymerization Methods 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- GVNWZKBFMFUVNX-UHFFFAOYSA-N Adipamide Chemical compound NC(=O)CCCCC(N)=O GVNWZKBFMFUVNX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 238000012644 addition polymerization Methods 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 150000007860 aryl ester derivatives Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- 230000000379 polymerizing effect Effects 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- DVPHDWQFZRBFND-DMHDVGBCSA-N 1-o-[2-[(3ar,5r,6s,6ar)-2,2-dimethyl-6-prop-2-enoyloxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-[4-[(2s,3r)-1-butan-2-ylsulfanyl-2-(2-chlorophenyl)-4-oxoazetidin-3-yl]oxy-4-oxobutanoyl]oxyethyl] 4-o-[(2s,3r)-1-butan-2-ylsulfanyl-2-(2-chloropheny Chemical group C1([C@H]2[C@H](C(N2SC(C)CC)=O)OC(=O)CCC(=O)OC(COC(=O)CCC(=O)O[C@@H]2[C@@H](N(C2=O)SC(C)CC)C=2C(=CC=CC=2)Cl)[C@@H]2[C@@H]([C@H]3OC(C)(C)O[C@H]3O2)OC(=O)C=C)=CC=CC=C1Cl DVPHDWQFZRBFND-DMHDVGBCSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- UFFRSDWQMJYQNE-UHFFFAOYSA-N 6-azaniumylhexylazanium;hexanedioate Chemical compound [NH3+]CCCCCC[NH3+].[O-]C(=O)CCCCC([O-])=O UFFRSDWQMJYQNE-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 101100326920 Caenorhabditis elegans ctl-1 gene Proteins 0.000 description 1
- 241000518994 Conta Species 0.000 description 1
- 229920000305 Nylon 6,10 Polymers 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229920000800 acrylic rubber Polymers 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 229920006228 ethylene acrylate copolymer Polymers 0.000 description 1
- 229920001038 ethylene copolymer Polymers 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 1
- 239000011344 liquid material Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 230000000116 mitigating effect Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000002667 nucleating agent Substances 0.000 description 1
- 150000002889 oleic acids Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 230000000644 propagated effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- 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
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
-
- 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
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/26—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids
- C08G69/34—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids using polymerised unsaturated fatty acids
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyamides (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/586,332 US4018731A (en) | 1975-06-12 | 1975-06-12 | High impact polyamides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1080879A true CA1080879A (en) | 1980-07-01 |
Family
ID=24345311
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA253,105A Expired CA1080879A (en) | 1975-06-12 | 1976-05-21 | High impact polyamides |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4018731A (enExample) |
| JP (1) | JPS51151798A (enExample) |
| CA (1) | CA1080879A (enExample) |
| DE (1) | DE2626273A1 (enExample) |
| FR (1) | FR2314225A1 (enExample) |
| GB (1) | GB1528852A (enExample) |
| IT (1) | IT1063450B (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4218351A (en) * | 1978-07-17 | 1980-08-19 | Minnesota Mining And Manufacturing Company | Impact resistant, thermoplastic polyamides |
| US4299744A (en) * | 1980-06-06 | 1981-11-10 | American Hoechst Corporation | High impact polyamides |
| JPS5747329A (en) * | 1980-09-05 | 1982-03-18 | Daicel Chem Ind Ltd | Copolyamide resin |
| DE3105365A1 (de) * | 1981-02-13 | 1982-09-02 | Bayer Ag, 5090 Leverkusen | Blockcopolymere |
| EP0073838B2 (en) * | 1981-03-16 | 1992-03-11 | Daicel Chemical Industries, Ltd. | Copolymerized polyamide resin |
| US4414362A (en) * | 1982-03-04 | 1983-11-08 | The General Tire & Rubber Company | Preparation of polyamides |
| US4511696A (en) * | 1983-06-29 | 1985-04-16 | Shell Oil Company | Method for protectively coating a polymer |
| DE3527037A1 (de) * | 1985-07-27 | 1987-01-29 | Plate Bonn Gmbh | Copolyamide, verfahren zu ihrer herstellung und ihre verwendung |
| US7001979B2 (en) * | 2002-06-14 | 2006-02-21 | H.B. Fuller Licensing & Financing Inc. | Polyamide and composition and article including same |
| FR3026107B1 (fr) * | 2014-09-24 | 2018-02-16 | Arkema France | Utilisation d'un copolymere a blocs pour la protection de pieces a base de metaux |
| FR3049283B1 (fr) * | 2016-03-24 | 2018-03-23 | Compagnie Generale Des Etablissements Michelin | Produit renforce comprenant un renfort composite auto-adherent comprenant un copolymere a blocs |
| FR3049281B1 (fr) * | 2016-03-24 | 2019-11-01 | Arkema France | Copolymere a blocs pour la protection de pieces a base de metaux |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3671478A (en) * | 1968-09-19 | 1972-06-20 | Dunlop Holdings Ltd | Rubber compositions |
| US3645932A (en) * | 1969-05-22 | 1972-02-29 | Gen Mills Inc | Nucleation of high molecular weight polyamides |
-
1975
- 1975-06-12 US US05/586,332 patent/US4018731A/en not_active Expired - Lifetime
-
1976
- 1976-05-21 CA CA253,105A patent/CA1080879A/en not_active Expired
- 1976-06-08 IT IT24051/76A patent/IT1063450B/it active
- 1976-06-11 FR FR7617862A patent/FR2314225A1/fr active Granted
- 1976-06-11 GB GB24339/76A patent/GB1528852A/en not_active Expired
- 1976-06-11 DE DE19762626273 patent/DE2626273A1/de not_active Withdrawn
- 1976-06-12 JP JP51068248A patent/JPS51151798A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| FR2314225B3 (enExample) | 1979-03-02 |
| JPS51151798A (en) | 1976-12-27 |
| IT1063450B (it) | 1985-02-11 |
| US4018731A (en) | 1977-04-19 |
| GB1528852A (en) | 1978-10-18 |
| FR2314225A1 (fr) | 1977-01-07 |
| DE2626273A1 (de) | 1976-12-23 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1080879A (en) | High impact polyamides | |
| US6525166B1 (en) | Polyamides with high fluidity, method for making same, compositions said polyamide | |
| KR970000487B1 (ko) | 신규 폴리아미드류 및 이로부터 수득되는 물품 | |
| KR100355649B1 (ko) | 폴리아마이드및당해폴리아마이드의제조방법및당해폴리아마이드를함유한조성물 | |
| US3554983A (en) | Polyesteramides prepared from caprolactone hexamethylene diamine and a mixture of isophthalic and terephthalic acids | |
| US5028689A (en) | Branched (co)polyamide by polycondensation in the presence of lysine component polycarboxylic acid mixture | |
| US4473686A (en) | Block copolymers | |
| US3093618A (en) | Polyamides from beta-amino carboxylic acids | |
| US3442975A (en) | Polyimine/polycarbonamide graft polymers | |
| US5597888A (en) | Process for the production of high molecular weight polyamide 6 | |
| KR20030068156A (ko) | 폴리아미드 | |
| US4892927A (en) | α-amino-ε-caprolactam-modified polyamide of dicarboxylic acids/diamines | |
| US3036988A (en) | Homogeneous blend of a polyamide and a polyvinyl lactam and process for producing | |
| US3352942A (en) | Polyamides from 3-amino methyl-3, 5, 5-trimethyl-cyclohexylamine and an amino acid | |
| US3627736A (en) | Polyamides from isophorone diamine, hexamethylene diamine, isophthalic acid and terephthalic acid | |
| US4959452A (en) | Alpha-amino-epsilon-caprolactam-modified polyamide preparation | |
| CA1255039A (en) | Promotion of epsilon-caprolactam polymerization | |
| US5026818A (en) | Melt preparation of polyamide with additive combination | |
| US5049651A (en) | Process for the preparation of branched (co)polyamides by solid phase post-condensation, and corresponding (co)-polyamides | |
| US5200498A (en) | Lactam-lactone copolymer | |
| US3481923A (en) | Production of copolymers of lactams and dienes | |
| CA1080889A (en) | Process for preparing polyamides of pacp | |
| US2615863A (en) | Polymers | |
| US3801549A (en) | Low melt viscosity molding process for high heat distortion interpolymers | |
| US5292857A (en) | Preparation of nylon 66 polymers from 1,8-diazacyclotetradecane-2,7-dione |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |