DE2152267A1 - Polydodecamethylenterephthalamidcopolymere und ihre Herstellung - Google Patents
Polydodecamethylenterephthalamidcopolymere und ihre HerstellungInfo
- Publication number
- DE2152267A1 DE2152267A1 DE19712152267 DE2152267A DE2152267A1 DE 2152267 A1 DE2152267 A1 DE 2152267A1 DE 19712152267 DE19712152267 DE 19712152267 DE 2152267 A DE2152267 A DE 2152267A DE 2152267 A1 DE2152267 A1 DE 2152267A1
- Authority
- DE
- Germany
- Prior art keywords
- dodecamethylene
- diammonium
- acid
- fiber
- salts
- 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.)
- Pending
Links
- -1 Polydodecamethylene terephthalamide copolymers Polymers 0.000 title claims description 13
- 238000002360 preparation method Methods 0.000 title claims description 9
- 150000003839 salts Chemical class 0.000 claims description 81
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 70
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 68
- 239000000835 fiber Substances 0.000 claims description 44
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 27
- 229920001577 copolymer Polymers 0.000 claims description 25
- 229920000642 polymer Polymers 0.000 claims description 24
- 239000002253 acid Substances 0.000 claims description 23
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 17
- QFTYSVGGYOXFRQ-UHFFFAOYSA-N dodecane-1,12-diamine Chemical compound NCCCCCCCCCCCCN QFTYSVGGYOXFRQ-UHFFFAOYSA-N 0.000 claims description 16
- 230000009477 glass transition Effects 0.000 claims description 16
- 238000006116 polymerization reaction Methods 0.000 claims description 15
- 239000012456 homogeneous solution Substances 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 11
- 229920006115 poly(dodecamethylene terephthalamide) Polymers 0.000 claims description 11
- 239000002002 slurry Substances 0.000 claims description 11
- FFPQSNUAVYJZDH-UHFFFAOYSA-N diazanium;terephthalate Chemical compound [NH4+].[NH4+].[O-]C(=O)C1=CC=C(C([O-])=O)C=C1 FFPQSNUAVYJZDH-UHFFFAOYSA-N 0.000 claims description 10
- OCBDCKOLSAYNMN-UHFFFAOYSA-N 4-(azacyclotridecane-1-carbonyl)benzamide Chemical group C1=CC(C(=O)N)=CC=C1C(=O)N1CCCCCCCCCCCC1 OCBDCKOLSAYNMN-UHFFFAOYSA-N 0.000 claims description 7
- 239000004952 Polyamide Substances 0.000 claims description 7
- 239000012736 aqueous medium Substances 0.000 claims description 7
- 229920002647 polyamide Polymers 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 7
- ZWUNKULTLYLLTH-UHFFFAOYSA-N cyclohexane-1,4-dicarboxamide Chemical group NC(=O)C1CCC(C(N)=O)CC1 ZWUNKULTLYLLTH-UHFFFAOYSA-N 0.000 claims description 6
- 239000008240 homogeneous mixture Substances 0.000 claims description 6
- QZUPTXGVPYNUIT-UHFFFAOYSA-N isophthalamide Chemical compound NC(=O)C1=CC=CC(C(N)=O)=C1 QZUPTXGVPYNUIT-UHFFFAOYSA-N 0.000 claims description 5
- 150000001408 amides Chemical class 0.000 claims description 3
- IPRCVFMLNWMMLD-UHFFFAOYSA-N azane;benzene-1,3-dicarboxylic acid Chemical compound [NH4+].[NH4+].[O-]C(=O)C1=CC=CC(C([O-])=O)=C1 IPRCVFMLNWMMLD-UHFFFAOYSA-N 0.000 claims description 3
- 238000000465 moulding Methods 0.000 claims description 3
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 claims description 3
- CGQSJWFALMCRBE-UHFFFAOYSA-N 3-(azacyclotridecane-1-carbonyl)benzamide benzene-1,4-dicarboxamide Chemical compound C(C1=CC(C(=O)N)=CC=C1)(=O)N1CCCCCCCCCCCC1.C(C1=CC=C(C(=O)N)C=C1)(=O)N CGQSJWFALMCRBE-UHFFFAOYSA-N 0.000 claims description 2
- QUPZXEHZHRRVRO-UHFFFAOYSA-N 2-butylbenzene-1,3-dicarboxamide Chemical compound CCCCC1=C(C(N)=O)C=CC=C1C(N)=O QUPZXEHZHRRVRO-UHFFFAOYSA-N 0.000 claims 1
- WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 claims 1
- LBFPJYOAXXNNDV-UHFFFAOYSA-N N=C=O.N=C=O.N.N Chemical compound N=C=O.N=C=O.N.N LBFPJYOAXXNNDV-UHFFFAOYSA-N 0.000 claims 1
- JMLPVHXESHXUSV-UHFFFAOYSA-N dodecane-1,1-diamine Chemical compound CCCCCCCCCCCC(N)N JMLPVHXESHXUSV-UHFFFAOYSA-N 0.000 claims 1
- 150000002531 isophthalic acids Chemical class 0.000 claims 1
- 239000000243 solution Substances 0.000 description 28
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 12
- 238000002844 melting Methods 0.000 description 11
- 239000004677 Nylon Substances 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- 229920001778 nylon Polymers 0.000 description 10
- 238000010438 heat treatment Methods 0.000 description 9
- 239000012266 salt solution Substances 0.000 description 8
- 239000003381 stabilizer Substances 0.000 description 7
- 150000007513 acids Chemical class 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000000975 dye Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000003610 charcoal Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 238000002074 melt spinning Methods 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000006068 polycondensation reaction Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- RTLULCVBFCRQKI-UHFFFAOYSA-N 1-amino-4-[3-[(4,6-dichloro-1,3,5-triazin-2-yl)amino]-4-sulfoanilino]-9,10-dioxoanthracene-2-sulfonic acid Chemical compound C1=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=C(S(O)(=O)=O)C=C1NC(C=1)=CC=C(S(O)(=O)=O)C=1NC1=NC(Cl)=NC(Cl)=N1 RTLULCVBFCRQKI-UHFFFAOYSA-N 0.000 description 2
- BJLUCDZIWWSFIB-UHFFFAOYSA-N 5-tert-butylbenzene-1,3-dicarboxylic acid Chemical compound CC(C)(C)C1=CC(C(O)=O)=CC(C(O)=O)=C1 BJLUCDZIWWSFIB-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- LJYTWOBAOVEHBG-UHFFFAOYSA-N azane;cyclohexane-1,4-dicarboxylic acid Chemical compound N.N.OC(=O)C1CCC(C(O)=O)CC1 LJYTWOBAOVEHBG-UHFFFAOYSA-N 0.000 description 2
- 239000000981 basic dye Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 2
- 239000000986 disperse dye Substances 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-L isophthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC(C([O-])=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-L 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000985 reactive dye Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000009987 spinning Methods 0.000 description 2
- 150000003503 terephthalic acid derivatives Chemical class 0.000 description 2
- 230000037303 wrinkles Effects 0.000 description 2
- CQXQJQKVRKYTOO-UHFFFAOYSA-N 3-n-tert-butylbenzene-1,3-dicarboxamide Chemical compound CC(C)(C)NC(=O)C1=CC=CC(C(N)=O)=C1 CQXQJQKVRKYTOO-UHFFFAOYSA-N 0.000 description 1
- 229920004934 Dacron® Polymers 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000005253 cladding Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000000748 compression moulding Methods 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000005489 elastic deformation Effects 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 239000002932 luster Substances 0.000 description 1
- FLFJVPPJGJSHMF-UHFFFAOYSA-L manganese hypophosphite Chemical compound [Mn+2].[O-]P=O.[O-]P=O FLFJVPPJGJSHMF-UHFFFAOYSA-L 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229920002113 octoxynol Polymers 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- WPPDXAHGCGPUPK-UHFFFAOYSA-N red 2 Chemical compound C1=CC=CC=C1C(C1=CC=CC=C11)=C(C=2C=3C4=CC=C5C6=CC=C7C8=C(C=9C=CC=CC=9)C9=CC=CC=C9C(C=9C=CC=CC=9)=C8C8=CC=C(C6=C87)C(C=35)=CC=2)C4=C1C1=CC=CC=C1 WPPDXAHGCGPUPK-UHFFFAOYSA-N 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000011833 salt mixture Substances 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 210000002435 tendon Anatomy 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 1
- 235000019801 trisodium phosphate Nutrition 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 239000008096 xylene Substances 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)
- Polyamides (AREA)
- Artificial Filaments (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8252370A | 1970-10-20 | 1970-10-20 | |
| US00082522A US3833547A (en) | 1970-10-20 | 1970-10-20 | Polydodecamethylene terephthalamide copolyamide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2152267A1 true DE2152267A1 (de) | 1972-04-27 |
Family
ID=26767552
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712152267 Pending DE2152267A1 (de) | 1970-10-20 | 1971-10-20 | Polydodecamethylenterephthalamidcopolymere und ihre Herstellung |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS5439440B1 (cg-RX-API-DMAC7.html) |
| DE (1) | DE2152267A1 (cg-RX-API-DMAC7.html) |
| FR (1) | FR2116379B1 (cg-RX-API-DMAC7.html) |
| GB (1) | GB1374275A (cg-RX-API-DMAC7.html) |
| IT (1) | IT939611B (cg-RX-API-DMAC7.html) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2509759B2 (ja) * | 1989-07-31 | 1996-06-26 | アライド―シグナル・インコーポレーテッド | ドデカンテレフタルアミドの共重合体 |
-
1971
- 1971-10-18 IT IT5355871A patent/IT939611B/it active
- 1971-10-19 GB GB4858771A patent/GB1374275A/en not_active Expired
- 1971-10-20 FR FR7137702A patent/FR2116379B1/fr not_active Expired
- 1971-10-20 JP JP8253771A patent/JPS5439440B1/ja active Pending
- 1971-10-20 DE DE19712152267 patent/DE2152267A1/de active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| FR2116379B1 (cg-RX-API-DMAC7.html) | 1974-09-06 |
| JPS5439440B1 (cg-RX-API-DMAC7.html) | 1979-11-28 |
| GB1374275A (en) | 1974-11-20 |
| FR2116379A1 (cg-RX-API-DMAC7.html) | 1972-07-13 |
| IT939611B (it) | 1973-02-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| OHW | Rejection |