CA1163043A - Transparent copolyamides and their use for the production of mouldings - Google Patents
Transparent copolyamides and their use for the production of mouldingsInfo
- Publication number
- CA1163043A CA1163043A CA000380222A CA380222A CA1163043A CA 1163043 A CA1163043 A CA 1163043A CA 000380222 A CA000380222 A CA 000380222A CA 380222 A CA380222 A CA 380222A CA 1163043 A CA1163043 A CA 1163043A
- Authority
- CA
- Canada
- Prior art keywords
- mixture
- diamine
- amide
- terephthalic acid
- atoms
- 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
- 238000000465 moulding Methods 0.000 title abstract description 6
- 238000004519 manufacturing process Methods 0.000 title abstract description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims abstract description 72
- 239000000203 mixture Substances 0.000 claims abstract description 62
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims abstract description 44
- 150000004985 diamines Chemical class 0.000 claims abstract description 32
- 150000003839 salts Chemical class 0.000 claims abstract description 15
- 238000006243 chemical reaction Methods 0.000 claims abstract description 9
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910003953 H3PO2 Inorganic materials 0.000 claims abstract 3
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 claims abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 32
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
- 239000000376 reactant Substances 0.000 claims description 16
- -1 aliphatic diamine Chemical class 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 3
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 3
- FVUKYCZRWSQGAS-UHFFFAOYSA-N 3-carbamoylbenzoic acid Chemical class NC(=O)C1=CC=CC(C(O)=O)=C1 FVUKYCZRWSQGAS-UHFFFAOYSA-N 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000000524 functional group Chemical group 0.000 claims description 2
- 150000002531 isophthalic acids Chemical class 0.000 claims description 2
- KYARBIJYVGJZLB-UHFFFAOYSA-N 7-amino-4-hydroxy-2-naphthalenesulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KYARBIJYVGJZLB-UHFFFAOYSA-N 0.000 claims 3
- 150000001408 amides Chemical class 0.000 claims 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 10
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 abstract description 5
- 238000010521 absorption reaction Methods 0.000 abstract description 5
- 230000007062 hydrolysis Effects 0.000 abstract description 2
- 238000006460 hydrolysis reaction Methods 0.000 abstract description 2
- 229920001169 thermoplastic Polymers 0.000 abstract 1
- 239000004416 thermosoftening plastic Substances 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 238000000034 method Methods 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000006068 polycondensation reaction Methods 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000000654 additive Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 150000001991 dicarboxylic acids Chemical class 0.000 description 3
- 125000006267 biphenyl group Chemical group 0.000 description 2
- 229920006018 co-polyamide Polymers 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 229920001577 copolymer Chemical class 0.000 description 2
- 230000000875 corresponding effect Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- ZFOODCBUKSMZBZ-UHFFFAOYSA-N 6,6-dimethylundecane Chemical compound CCCCCC(C)(C)CCCCC ZFOODCBUKSMZBZ-UHFFFAOYSA-N 0.000 description 1
- 235000003625 Acrocomia mexicana Nutrition 0.000 description 1
- 244000202285 Acrocomia mexicana Species 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical class CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- JDRJCBXXDRYVJC-UHFFFAOYSA-N OP(O)O.N.N.N Chemical compound OP(O)O.N.N.N JDRJCBXXDRYVJC-UHFFFAOYSA-N 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 description 1
- DIOQZVSQGTUSAI-NJFSPNSNSA-N decane Chemical class CCCCCCCCC[14CH3] DIOQZVSQGTUSAI-NJFSPNSNSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical class CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 235000015250 liver sausages Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical class C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 235000014786 phosphorus Nutrition 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- 150000003504 terephthalic acids Chemical class 0.000 description 1
- OBSZRRSYVTXPNB-UHFFFAOYSA-N tetraphosphorus Chemical compound P12P3P1P32 OBSZRRSYVTXPNB-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- KQAYXXFFBQKDEP-UHFFFAOYSA-N undecane-6,6-diamine Chemical class CCCCCC(N)(N)CCCCC KQAYXXFFBQKDEP-UHFFFAOYSA-N 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
- C08G69/26—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids
- C08G69/265—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids from at least two different diamines or at least two different dicarboxylic 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
- C08G69/28—Preparatory processes
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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH480680 | 1980-06-23 | ||
| CH4806/80-3 | 1980-06-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1163043A true CA1163043A (en) | 1984-02-28 |
Family
ID=4282869
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000380222A Expired CA1163043A (en) | 1980-06-23 | 1981-06-19 | Transparent copolyamides and their use for the production of mouldings |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4377683A (en, 2012) |
| EP (1) | EP0042820B1 (en, 2012) |
| JP (1) | JPS5730725A (en, 2012) |
| CA (1) | CA1163043A (en, 2012) |
| DE (1) | DE3170824D1 (en, 2012) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0085652B1 (de) * | 1982-01-29 | 1985-03-13 | Ciba-Geigy Ag | 1,10-substituierte 10-Amino-deca-3,7-dien-nitrile und Verfahren zu deren Herstellung |
| EP0087385B1 (de) * | 1982-01-29 | 1986-09-17 | Ciba-Geigy Ag | Vernetzbare transparente Polyamide |
| JPS60148202U (ja) * | 1984-03-14 | 1985-10-02 | 株式会社森山機械工作所 | マツチ箱詰機に於ける押え紙插入装置 |
| JP2596761B2 (ja) * | 1987-10-01 | 1997-04-02 | 有限会社秋山機工 | シート折畳み装置 |
| DE29514658U1 (de) * | 1995-09-12 | 1996-01-11 | Ems-Inventa AG, Zürich | Streuscheibe für Beleuchtungssysteme |
| KR102447869B1 (ko) * | 2017-02-21 | 2022-09-27 | 미쯔비시 가스 케미칼 컴파니, 인코포레이티드 | 비정성 폴리아미드 수지 및 성형품 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3173898A (en) * | 1961-03-20 | 1965-03-16 | Du Pont | Polymerization of polyamide-forming reactants with hypophosphite catalysts |
| DE1173248B (de) * | 1961-12-06 | 1964-07-02 | Hibernia Chemi Ges Mit Beschra | Verfahren zur Herstellung von Polyamiden |
| DE1495877A1 (de) | 1962-09-06 | 1969-07-03 | Scholven Chemie Ag | Kochbestaendige,lineare Mischpolyamide,sowie Verfahren zur Herstellung derselben |
| US3294759A (en) * | 1963-08-26 | 1966-12-27 | Grace W R & Co | Linear copolyamides resistant to boiling water |
| DE1520924A1 (de) * | 1963-11-14 | 1970-01-02 | Scholven Chemie Ag | Verfahren zur Herstellung von Polyamiden |
| FR1423272A (fr) * | 1964-01-29 | 1966-03-18 | Scholven Chemie Ag | Procédé de fabrication de polycondensats et produits conformes à ceux obtenus parle présent procédé ou procédé similaire |
| GB1125770A (en) | 1964-12-30 | 1968-08-28 | British Celanese | Improved polyamide compositions |
| GB1228762A (en, 2012) | 1967-05-18 | 1971-04-21 | ||
| GB1268374A (en) | 1968-05-29 | 1972-03-29 | Bp Chem Int Ltd | Polyamide |
| GB1255483A (en) | 1968-11-18 | 1971-12-01 | Bp Chem Int Ltd | Polyamides |
| DE1905539A1 (de) | 1969-02-05 | 1970-09-17 | Wolff Walsrode Ag | Einstufig erzeugte Polyamid-Folie,ihre Herstellung und Verwendung als Verpackungsmaterial |
| US3627736A (en) * | 1970-05-28 | 1971-12-14 | Alaric Louis Jeffrey Raum | Polyamides from isophorone diamine, hexamethylene diamine, isophthalic acid and terephthalic acid |
| GB1410006A (en) | 1971-09-15 | 1975-10-15 | Bp Chem Int Ltd | Polyamide |
| GB1410007A (en) | 1971-09-15 | 1975-10-15 | Bp Chem Int Ltd | Polyamide |
| US4258176A (en) * | 1978-10-18 | 1981-03-24 | Ciba-Geigy Corporation | Transparent copolyamide from 1,10-disubstituted C11 diamine |
-
1981
- 1981-06-12 US US06/272,866 patent/US4377683A/en not_active Expired - Fee Related
- 1981-06-17 DE DE8181810250T patent/DE3170824D1/de not_active Expired
- 1981-06-17 EP EP81810250A patent/EP0042820B1/de not_active Expired
- 1981-06-18 JP JP9311781A patent/JPS5730725A/ja active Granted
- 1981-06-19 CA CA000380222A patent/CA1163043A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| EP0042820B1 (de) | 1985-06-05 |
| US4377683A (en) | 1983-03-22 |
| DE3170824D1 (en) | 1985-07-11 |
| EP0042820A3 (en) | 1982-08-25 |
| EP0042820A2 (de) | 1981-12-30 |
| JPH0132850B2 (en, 2012) | 1989-07-10 |
| JPS5730725A (en) | 1982-02-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |