CA1207940A - Crystalline copolyamides from terephthalic acid and hexamethylenediamine and trimethylhexamethylenediamine - Google Patents
Crystalline copolyamides from terephthalic acid and hexamethylenediamine and trimethylhexamethylenediamineInfo
- Publication number
- CA1207940A CA1207940A CA000446713A CA446713A CA1207940A CA 1207940 A CA1207940 A CA 1207940A CA 000446713 A CA000446713 A CA 000446713A CA 446713 A CA446713 A CA 446713A CA 1207940 A CA1207940 A CA 1207940A
- Authority
- CA
- Canada
- Prior art keywords
- polyamide
- copolyamide
- fibers
- glass
- trimethylhexamethylene
- 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
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 title claims abstract description 38
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 title claims abstract description 32
- ZETYUTMSJWMKNQ-UHFFFAOYSA-N n,n',n'-trimethylhexane-1,6-diamine Chemical compound CNCCCCCCN(C)C ZETYUTMSJWMKNQ-UHFFFAOYSA-N 0.000 title claims abstract description 18
- 239000000203 mixture Substances 0.000 claims abstract description 32
- 239000004952 Polyamide Substances 0.000 claims description 26
- 239000000835 fiber Substances 0.000 claims description 26
- 229920002647 polyamide Polymers 0.000 claims description 25
- 239000011521 glass Substances 0.000 claims description 20
- 239000003365 glass fiber Substances 0.000 claims description 18
- 239000011324 bead Substances 0.000 claims description 15
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
- 239000010439 graphite Substances 0.000 claims description 10
- 229910002804 graphite Inorganic materials 0.000 claims description 10
- 238000002347 injection Methods 0.000 claims description 9
- 239000007924 injection Substances 0.000 claims description 9
- -1 aliphatic hydrocarbon rad-ical Chemical class 0.000 claims description 7
- 229940090044 injection Drugs 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 150000001721 carbon Chemical group 0.000 claims description 2
- 229920006039 crystalline polyamide Polymers 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims 3
- 239000002557 mineral fiber Substances 0.000 claims 3
- 229920001577 copolymer Polymers 0.000 claims 1
- 238000000465 moulding Methods 0.000 abstract description 6
- 229920000642 polymer Polymers 0.000 description 22
- 238000000034 method Methods 0.000 description 15
- 229910052500 inorganic mineral Inorganic materials 0.000 description 8
- 239000011707 mineral Substances 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 238000001746 injection moulding Methods 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 5
- 230000010006 flight Effects 0.000 description 5
- 239000000155 melt Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 208000036366 Sensation of pressure Diseases 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- KWSLGOVYXMQPPX-UHFFFAOYSA-N 5-[3-(trifluoromethyl)phenyl]-2h-tetrazole Chemical group FC(F)(F)C1=CC=CC(C2=NNN=N2)=C1 KWSLGOVYXMQPPX-UHFFFAOYSA-N 0.000 description 2
- XWLAQGPKVJIMRW-UHFFFAOYSA-M 6-azaniumylhexyl(trimethyl)azanium;terephthalate Chemical compound C[N+](C)(C)CCCCCC[NH3+].[O-]C(=O)C1=CC=C(C([O-])=O)C=C1 XWLAQGPKVJIMRW-UHFFFAOYSA-M 0.000 description 2
- CSVBIURHUGXNCS-UHFFFAOYSA-N 6-azaniumylhexylazanium;terephthalate Chemical compound NCCCCCCN.OC(=O)C1=CC=C(C(O)=O)C=C1 CSVBIURHUGXNCS-UHFFFAOYSA-N 0.000 description 2
- 238000013329 compounding Methods 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 239000012779 reinforcing material Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229910001379 sodium hypophosphite Inorganic materials 0.000 description 2
- JCUZDQXWVYNXHD-UHFFFAOYSA-N 2,2,4-trimethylhexane-1,6-diamine Chemical compound NCCC(C)CC(C)(C)CN JCUZDQXWVYNXHD-UHFFFAOYSA-N 0.000 description 1
- DPQHRXRAZHNGRU-UHFFFAOYSA-N 2,4,4-trimethylhexane-1,6-diamine Chemical compound NCC(C)CC(C)(C)CCN DPQHRXRAZHNGRU-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical class C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- AYHOQSGNVUZKJA-UHFFFAOYSA-N [B+3].[B+3].[B+3].[B+3].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-] Chemical compound [B+3].[B+3].[B+3].[B+3].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-] AYHOQSGNVUZKJA-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229920006020 amorphous polyamide Polymers 0.000 description 1
- QXJJQWWVWRCVQT-UHFFFAOYSA-K calcium;sodium;phosphate Chemical compound [Na+].[Ca+2].[O-]P([O-])([O-])=O QXJJQWWVWRCVQT-UHFFFAOYSA-K 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 150000001991 dicarboxylic acids Chemical group 0.000 description 1
- 229920006351 engineering plastic Polymers 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 230000033001 locomotion Effects 0.000 description 1
- 238000002074 melt spinning Methods 0.000 description 1
- RTWNYYOXLSILQN-UHFFFAOYSA-N methanediamine Chemical compound NCN RTWNYYOXLSILQN-UHFFFAOYSA-N 0.000 description 1
- 239000003595 mist Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- DMCTVRQBJMBEDT-UHFFFAOYSA-N phenol;1,1,1,2-tetrachloroethane Chemical compound ClCC(Cl)(Cl)Cl.OC1=CC=CC=C1 DMCTVRQBJMBEDT-UHFFFAOYSA-N 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920006111 poly(hexamethylene terephthalamide) Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000036647 reaction Effects 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 239000005368 silicate glass Substances 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polyamides (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US46690383A | 1983-02-16 | 1983-02-16 | |
| US466,903 | 1983-02-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1207940A true CA1207940A (en) | 1986-07-15 |
Family
ID=23853528
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000446713A Expired CA1207940A (en) | 1983-02-16 | 1984-02-03 | Crystalline copolyamides from terephthalic acid and hexamethylenediamine and trimethylhexamethylenediamine |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP0121985B2 (enExample) |
| JP (1) | JPS59155427A (enExample) |
| CA (1) | CA1207940A (enExample) |
| DE (1) | DE3473606D1 (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61283653A (ja) * | 1985-06-11 | 1986-12-13 | Sumitomo Chem Co Ltd | 樹脂組成物 |
| JPS61283654A (ja) * | 1985-06-11 | 1986-12-13 | Sumitomo Chem Co Ltd | 樹脂組成物 |
| US8309640B2 (en) | 2008-05-23 | 2012-11-13 | Sabic Innovative Plastics Ip B.V. | High dielectric constant laser direct structuring materials |
| JP2013544296A (ja) | 2010-10-25 | 2013-12-12 | サビック・イノベーティブ・プラスチックス・アイピー・ベスローテン・フェンノートシャップ | レーザダイレクトストラクチャリング材料の改善された無電解メッキ性能 |
| JP2013545832A (ja) | 2010-10-26 | 2013-12-26 | サビック・イノベーティブ・プラスチックス・アイピー・ベスローテン・フェンノートシャップ | すべての色特性を有するレーザダイレクトストラクチャリング材料 |
| US9185800B2 (en) | 2012-09-17 | 2015-11-10 | Sabic Global Technologies B.V. | Laser direct structuring materials with improved plating performance and acceptable mechanical properties |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL296609A (enExample) * | 1962-08-14 | |||
| NL7108318A (enExample) * | 1970-07-04 | 1972-01-06 | ||
| DE2652465A1 (de) * | 1976-11-18 | 1978-05-24 | Bayer Ag | Transparente copolyamide |
-
1984
- 1984-02-03 CA CA000446713A patent/CA1207940A/en not_active Expired
- 1984-02-07 DE DE8484300746T patent/DE3473606D1/de not_active Expired
- 1984-02-07 EP EP19840300746 patent/EP0121985B2/en not_active Expired - Lifetime
- 1984-02-15 JP JP2690684A patent/JPS59155427A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| EP0121985A3 (en) | 1985-05-02 |
| EP0121985B2 (en) | 1995-07-26 |
| JPS59155427A (ja) | 1984-09-04 |
| EP0121985A2 (en) | 1984-10-17 |
| DE3473606D1 (en) | 1988-09-29 |
| EP0121985B1 (en) | 1988-08-24 |
| JPH0357136B2 (enExample) | 1991-08-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |