IE42183B1 - Fromation of n-alicyclic polyamides - Google Patents
Fromation of n-alicyclic polyamidesInfo
- Publication number
- IE42183B1 IE42183B1 IE255775A IE255775A IE42183B1 IE 42183 B1 IE42183 B1 IE 42183B1 IE 255775 A IE255775 A IE 255775A IE 255775 A IE255775 A IE 255775A IE 42183 B1 IE42183 B1 IE 42183B1
- Authority
- IE
- Ireland
- Prior art keywords
- process according
- low
- cyclohexylene
- polyamide
- alicyclic
- Prior art date
Links
- 239000004952 Polyamide Substances 0.000 title claims description 20
- 229920002647 polyamide Polymers 0.000 title claims description 20
- 238000000034 method Methods 0.000 claims description 22
- 238000010438 heat treatment Methods 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N methyl pentane Natural products CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 7
- 125000002723 alicyclic group Chemical group 0.000 claims description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 239000012298 atmosphere Substances 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 3
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 claims 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims 2
- 125000005828 4,4′-bicyclohexylene group Chemical group [H]C1([H])C([H])([H])C([H])(C([H])([H])C([H])([H])C1([H])[*:1])C1([H])C([H])([H])C([H])([H])C([H])([*:2])C([H])([H])C1([H])[H] 0.000 claims 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims 1
- 239000001294 propane Substances 0.000 claims 1
- 230000003287 optical effect Effects 0.000 abstract 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 26
- 229920000642 polymer Polymers 0.000 description 19
- 229910052757 nitrogen Inorganic materials 0.000 description 15
- -1 alicyclic diamines Chemical class 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 239000012265 solid product Substances 0.000 description 10
- 239000002253 acid Substances 0.000 description 8
- 239000000376 reactant Substances 0.000 description 8
- 150000004985 diamines Chemical class 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 4
- 239000000835 fiber Substances 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- 239000010935 stainless steel Substances 0.000 description 3
- WTKWFNIIIXNTDO-UHFFFAOYSA-N 3-isocyanato-5-methyl-2-(trifluoromethyl)furan Chemical compound CC1=CC(N=C=O)=C(C(F)(F)F)O1 WTKWFNIIIXNTDO-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 125000003368 amide group Chemical group 0.000 description 2
- 125000003435 aroyl group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000001589 carboacyl group Chemical group 0.000 description 2
- 125000005392 carboxamide group Chemical group NC(=O)* 0.000 description 2
- 150000003857 carboxamides Chemical class 0.000 description 2
- 125000005518 carboxamido group Chemical group 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- 239000011888 foil Substances 0.000 description 2
- 230000005484 gravity Effects 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- NTZRFIYXMXPYCB-UHFFFAOYSA-N n-(5-acetamido-1,2,3,4,4a,5,6,7,8,8a-decahydronaphthalen-1-yl)acetamide Chemical compound CC(=O)NC1CCCC2C(NC(=O)C)CCCC21 NTZRFIYXMXPYCB-UHFFFAOYSA-N 0.000 description 2
- TVIDDXQYHWJXFK-UHFFFAOYSA-N n-Dodecanedioic acid Natural products OC(=O)CCCCCCCCCCC(O)=O TVIDDXQYHWJXFK-UHFFFAOYSA-N 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- HQHCYKULIHKCEB-UHFFFAOYSA-N tetradecanedioic acid Natural products OC(=O)CCCCCCCCCCCCC(O)=O HQHCYKULIHKCEB-UHFFFAOYSA-N 0.000 description 2
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- 229910001006 Constantan Inorganic materials 0.000 description 1
- 101100117236 Drosophila melanogaster speck gene Proteins 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- GJBRTCPWCKRSTQ-UHFFFAOYSA-N decanedioic acid Chemical compound OC(=O)CCCCCCCCC(O)=O.OC(=O)CCCCCCCCC(O)=O GJBRTCPWCKRSTQ-UHFFFAOYSA-N 0.000 description 1
- 229920006240 drawn fiber Polymers 0.000 description 1
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000007380 fibre production Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000005337 ground glass Substances 0.000 description 1
- 229910000833 kovar Inorganic materials 0.000 description 1
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- LJCGNFZYBRNAFS-UHFFFAOYSA-N n-[4-[(4-acetamido-2-methylcyclohexyl)methyl]-3-methylcyclohexyl]acetamide Chemical compound CC1CC(NC(C)=O)CCC1CC1C(C)CC(NC(C)=O)CC1 LJCGNFZYBRNAFS-UHFFFAOYSA-N 0.000 description 1
- GARRJFMMGMBXKL-UHFFFAOYSA-N n-[4-[(4-acetamidocyclohexyl)methyl]cyclohexyl]acetamide Chemical compound C1CC(NC(=O)C)CCC1CC1CCC(NC(C)=O)CC1 GARRJFMMGMBXKL-UHFFFAOYSA-N 0.000 description 1
- PXUNIWWMNJCCQQ-UHFFFAOYSA-N n-[4-[(4-formamidocyclohexyl)methyl]cyclohexyl]formamide Chemical compound C1CC(NC=O)CCC1CC1CCC(NC=O)CC1 PXUNIWWMNJCCQQ-UHFFFAOYSA-N 0.000 description 1
- IEFVENYBLLCEDZ-UHFFFAOYSA-N n-[4-[2-(4-acetamidocyclohexyl)ethyl]cyclohexyl]acetamide Chemical compound C1CC(NC(=O)C)CCC1CCC1CCC(NC(C)=O)CC1 IEFVENYBLLCEDZ-UHFFFAOYSA-N 0.000 description 1
- BNVTWOSMFQHSGD-UHFFFAOYSA-N n-[4-[2-(4-acetamidocyclohexyl)propan-2-yl]cyclohexyl]acetamide Chemical compound C1CC(NC(=O)C)CCC1C(C)(C)C1CCC(NC(C)=O)CC1 BNVTWOSMFQHSGD-UHFFFAOYSA-N 0.000 description 1
- YNDYHIIBBJHHFX-UHFFFAOYSA-N n-[4-[6-(4-acetamidocyclohexyl)hexyl]cyclohexyl]acetamide Chemical compound C1CC(NC(=O)C)CCC1CCCCCCC1CCC(NC(C)=O)CC1 YNDYHIIBBJHHFX-UHFFFAOYSA-N 0.000 description 1
- VCCNSSSKUGMERD-UHFFFAOYSA-N n-[4-[[4-(butanoylamino)cyclohexyl]methyl]cyclohexyl]butanamide Chemical compound C1CC(NC(=O)CCC)CCC1CC1CCC(NC(=O)CCC)CC1 VCCNSSSKUGMERD-UHFFFAOYSA-N 0.000 description 1
- JEUOYYIJGSLKOQ-UHFFFAOYSA-N n-[4-[[4-(propanoylamino)cyclohexyl]methyl]cyclohexyl]propanamide Chemical compound C1CC(NC(=O)CC)CCC1CC1CCC(NC(=O)CC)CC1 JEUOYYIJGSLKOQ-UHFFFAOYSA-N 0.000 description 1
- YKEKYBOBVREARV-UHFFFAOYSA-N pentanedioic acid Chemical compound OC(=O)CCCC(O)=O.OC(=O)CCCC(O)=O YKEKYBOBVREARV-UHFFFAOYSA-N 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
- 229940080818 propionamide Drugs 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000010959 steel 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyamides (AREA)
- Transforming Light Signals Into Electric Signals (AREA)
- Artificial Filaments (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US54215675A | 1975-01-20 | 1975-01-20 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE42183L IE42183L (en) | 1976-07-20 |
| IE42183B1 true IE42183B1 (en) | 1980-06-18 |
Family
ID=24162577
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE255775A IE42183B1 (en) | 1975-01-20 | 1975-11-24 | Fromation of n-alicyclic polyamides |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS5196894A (enrdf_load_stackoverflow) |
| DE (1) | DE2558166A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2297873A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1503081A (enrdf_load_stackoverflow) |
| IE (1) | IE42183B1 (enrdf_load_stackoverflow) |
| IT (1) | IT1051460B (enrdf_load_stackoverflow) |
-
1975
- 1975-11-24 IE IE255775A patent/IE42183B1/en unknown
- 1975-12-09 IT IT7002075A patent/IT1051460B/it active
- 1975-12-23 DE DE19752558166 patent/DE2558166A1/de not_active Withdrawn
-
1976
- 1976-01-19 JP JP51004850A patent/JPS5196894A/ja active Pending
- 1976-01-19 FR FR7601278A patent/FR2297873A1/fr active Granted
- 1976-01-20 GB GB215176A patent/GB1503081A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IT1051460B (it) | 1981-04-21 |
| FR2297873B1 (enrdf_load_stackoverflow) | 1979-03-23 |
| FR2297873A1 (fr) | 1976-08-13 |
| GB1503081A (en) | 1978-03-08 |
| DE2558166A1 (de) | 1976-07-22 |
| JPS5196894A (en) | 1976-08-25 |
| IE42183L (en) | 1976-07-20 |
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