NO136192B - - Google Patents
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- Publication number
- NO136192B NO136192B NO374971A NO374971A NO136192B NO 136192 B NO136192 B NO 136192B NO 374971 A NO374971 A NO 374971A NO 374971 A NO374971 A NO 374971A NO 136192 B NO136192 B NO 136192B
- Authority
- NO
- Norway
- Prior art keywords
- reaction
- product
- methyl alcohol
- mixture
- carried out
- Prior art date
Links
- 239000000203 mixture Substances 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 26
- -1 diester diamides Chemical class 0.000 claims description 20
- 150000004985 diamines Chemical class 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 14
- 238000010438 heat treatment Methods 0.000 claims description 13
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 239000012298 atmosphere Substances 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 239000011261 inert gas Substances 0.000 claims description 5
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- 239000007791 liquid phase Substances 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 87
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 60
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 39
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 32
- 239000000047 product Substances 0.000 description 32
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 31
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
- 239000007787 solid Substances 0.000 description 22
- 238000009835 boiling Methods 0.000 description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- 238000000921 elemental analysis Methods 0.000 description 14
- 238000002844 melting Methods 0.000 description 14
- 230000008018 melting Effects 0.000 description 14
- 238000001816 cooling Methods 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 11
- 239000000178 monomer Substances 0.000 description 11
- 150000005690 diesters Chemical class 0.000 description 10
- QFTYSVGGYOXFRQ-UHFFFAOYSA-N dodecane-1,12-diamine Chemical compound NCCCCCCCCCCCCN QFTYSVGGYOXFRQ-UHFFFAOYSA-N 0.000 description 10
- 238000001035 drying Methods 0.000 description 10
- 238000001914 filtration Methods 0.000 description 10
- 125000003277 amino group Chemical group 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 8
- LQLQDKBJAIILIQ-UHFFFAOYSA-N Dibutyl terephthalate Chemical compound CCCCOC(=O)C1=CC=C(C(=O)OCCCC)C=C1 LQLQDKBJAIILIQ-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000000605 extraction Methods 0.000 description 6
- 229920006149 polyester-amide block copolymer Polymers 0.000 description 6
- 238000004455 differential thermal analysis Methods 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 125000004185 ester group Chemical group 0.000 description 5
- 235000019441 ethanol Nutrition 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 230000007306 turnover Effects 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- VIZORQUEIQEFRT-UHFFFAOYSA-N Diethyl adipate Chemical compound CCOC(=O)CCCCC(=O)OCC VIZORQUEIQEFRT-UHFFFAOYSA-N 0.000 description 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- GHLKSLMMWAKNBM-UHFFFAOYSA-N dodecane-1,12-diol Chemical compound OCCCCCCCCCCCCO GHLKSLMMWAKNBM-UHFFFAOYSA-N 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- QLUQHFODHZKSDT-UHFFFAOYSA-N 4-butoxycarbonylbenzoic acid Chemical compound CCCCOC(=O)C1=CC=C(C(O)=O)C=C1 QLUQHFODHZKSDT-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- QCCLAFRLFORCAL-UHFFFAOYSA-N butyl 4-(12-aminododecylcarbamoyl)benzoate Chemical compound CCCCOC(=O)C1=CC=C(C(=O)NCCCCCCCCCCCCN)C=C1 QCCLAFRLFORCAL-UHFFFAOYSA-N 0.000 description 2
- GXJPKIGCMGAHTL-UHFFFAOYSA-N dipropyl benzene-1,4-dicarboxylate Chemical compound CCCOC(=O)C1=CC=C(C(=O)OCCC)C=C1 GXJPKIGCMGAHTL-UHFFFAOYSA-N 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 230000001788 irregular Effects 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000005809 transesterification reaction Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- RGCVYEOTYJCNOS-UHFFFAOYSA-N (4-cyano-2-methylphenyl)boronic acid Chemical compound CC1=CC(C#N)=CC=C1B(O)O RGCVYEOTYJCNOS-UHFFFAOYSA-N 0.000 description 1
- RDDRLGQCIPIUIA-UHFFFAOYSA-N 1,4-dimethylcyclohexane-1,4-diamine Chemical compound CC1(N)CCC(C)(N)CC1 RDDRLGQCIPIUIA-UHFFFAOYSA-N 0.000 description 1
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 1
- FWTBRYBHCBCJEQ-UHFFFAOYSA-N 4-[(4-phenyldiazenylnaphthalen-1-yl)diazenyl]phenol Chemical compound C1=CC(O)=CC=C1N=NC(C1=CC=CC=C11)=CC=C1N=NC1=CC=CC=C1 FWTBRYBHCBCJEQ-UHFFFAOYSA-N 0.000 description 1
- FNXGXGFQRWJYTK-UHFFFAOYSA-N C(=O)(OC)C1=CC=C(C(=O)NCCCCCCN)C=C1 Chemical compound C(=O)(OC)C1=CC=C(C(=O)NCCCCCCN)C=C1 FNXGXGFQRWJYTK-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DRUKNYVQGHETPO-UHFFFAOYSA-N Nonanedioic acid dimethyl ester Natural products COC(=O)CCCCCCCC(=O)OC DRUKNYVQGHETPO-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229940067597 azelate Drugs 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
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- PWSKHLMYTZNYKO-UHFFFAOYSA-N heptane-1,7-diamine Chemical compound NCCCCCCCN PWSKHLMYTZNYKO-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 238000002074 melt spinning Methods 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- WFRBDWRZVBPBDO-UHFFFAOYSA-N tert-hexyl alcohol Natural products CCCC(C)(C)O WFRBDWRZVBPBDO-UHFFFAOYSA-N 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium 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
- C08G69/44—Polyester-amides
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyamides (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT3090170 | 1970-10-13 | ||
| IT3090070 | 1970-10-13 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO136192B true NO136192B (cs) | 1977-04-25 |
| NO136192C NO136192C (no) | 1977-08-03 |
Family
ID=26328901
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO374971A NO136192C (no) | 1970-10-13 | 1971-10-12 | Fremgangsm}te for fremstilling av diesterdiamider. |
Country Status (16)
| Country | Link |
|---|---|
| JP (2) | JPS5516132B1 (cs) |
| BE (1) | BE773738A (cs) |
| CA (1) | CA991199A (cs) |
| CH (1) | CH535203A (cs) |
| CS (1) | CS174167B2 (cs) |
| DE (1) | DE2150808B2 (cs) |
| DK (1) | DK150981C (cs) |
| FR (1) | FR2111288A5 (cs) |
| GB (1) | GB1365952A (cs) |
| HU (1) | HU167518B (cs) |
| LU (1) | LU64050A1 (cs) |
| NL (1) | NL173952C (cs) |
| NO (1) | NO136192C (cs) |
| SE (1) | SE378809B (cs) |
| SU (1) | SU1069623A3 (cs) |
| YU (1) | YU36144B (cs) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1588526A (en) * | 1976-07-21 | 1981-04-23 | Anic Spa | Elastomeric copolyesteramides |
| FR2362180A1 (fr) * | 1976-08-20 | 1978-03-17 | Ato Chimie | Copolyesteramides aliphatiques stables comme produits a mouler |
| IT1123574B (it) * | 1979-09-10 | 1986-04-30 | Anic Spa | Processo per la produzione di diesterediammidi |
| DE3003898A1 (de) * | 1980-02-02 | 1981-08-13 | Dynamit Nobel Ag, 5210 Troisdorf | Verfahren zur acylierung von aminocarbonsaeuren |
| JPS60160816U (ja) * | 1984-04-02 | 1985-10-25 | 廣前 孝明 | 爪楊枝セツト |
| JPS62180419U (cs) * | 1986-05-09 | 1987-11-16 | ||
| IT1190137B (it) * | 1986-06-20 | 1988-02-10 | Eniricerche Spa | Fibra cava di poliestere ammide e procedimento per la sua preparazione |
| US5852155A (en) * | 1995-03-01 | 1998-12-22 | General Electric Company | Compositions of polyesteramides |
| US5744068A (en) * | 1996-01-24 | 1998-04-28 | General Electric Company | Blends of polyphenylene ethers and polyesteramides |
| US5731389A (en) * | 1996-04-24 | 1998-03-24 | General Electric Company | Blends of polyesters and polyesteramides, optionally with polycarbonates |
| US8685431B2 (en) * | 2004-03-16 | 2014-04-01 | Advanced Cardiovascular Systems, Inc. | Biologically absorbable coatings for implantable devices based on copolymers having ester bonds and methods for fabricating the same |
| JP2016528350A (ja) * | 2013-08-16 | 2016-09-15 | ディーエスエム アイピー アセッツ ビー．ブイ． | ジアミドのセグメントを含む熱可塑性ポリマーを製造するための方法 |
| CN109956881A (zh) * | 2017-12-26 | 2019-07-02 | 上海凯赛生物技术研发中心有限公司 | 一种苯甲酰戊二胺及其制备和应用 |
-
1971
- 1971-10-11 CH CH1479671A patent/CH535203A/fr not_active IP Right Cessation
- 1971-10-11 BE BE773738A patent/BE773738A/xx not_active IP Right Cessation
- 1971-10-11 SU SU711703305A patent/SU1069623A3/ru active
- 1971-10-11 YU YU258071A patent/YU36144B/xx unknown
- 1971-10-12 HU HUSA002256 patent/HU167518B/hu unknown
- 1971-10-12 DE DE19712150808 patent/DE2150808B2/de active Granted
- 1971-10-12 CS CS717271A patent/CS174167B2/cs unknown
- 1971-10-12 LU LU64050D patent/LU64050A1/xx unknown
- 1971-10-12 DK DK494071A patent/DK150981C/da active
- 1971-10-12 JP JP7991771A patent/JPS5516132B1/ja active Pending
- 1971-10-12 CA CA124,969A patent/CA991199A/en not_active Expired
- 1971-10-12 NO NO374971A patent/NO136192C/no unknown
- 1971-10-12 GB GB4752171A patent/GB1365952A/en not_active Expired
- 1971-10-13 NL NL7114102A patent/NL173952C/xx not_active IP Right Cessation
- 1971-10-13 SE SE1299971A patent/SE378809B/xx unknown
- 1971-10-13 FR FR7136694A patent/FR2111288A5/fr not_active Expired
-
1978
- 1978-05-16 JP JP5725078A patent/JPS53149921A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| SE378809B (cs) | 1975-09-15 |
| AU3444971A (en) | 1973-04-19 |
| DK150981C (da) | 1988-02-22 |
| CH535203A (fr) | 1973-03-31 |
| JPS53149921A (en) | 1978-12-27 |
| CA991199A (en) | 1976-06-15 |
| YU258071A (en) | 1981-04-30 |
| GB1365952A (en) | 1974-09-04 |
| CS174167B2 (cs) | 1977-03-31 |
| NL173952C (nl) | 1984-04-02 |
| BE773738A (fr) | 1972-01-31 |
| NL7114102A (cs) | 1972-04-17 |
| DE2150808B2 (de) | 1978-08-10 |
| JPS5730097B2 (cs) | 1982-06-26 |
| NL173952B (nl) | 1983-11-01 |
| FR2111288A5 (cs) | 1972-06-02 |
| DK150981B (da) | 1987-10-05 |
| DE2150808C3 (cs) | 1979-04-12 |
| NO136192C (no) | 1977-08-03 |
| SU1069623A3 (ru) | 1984-01-23 |
| YU36144B (en) | 1982-02-25 |
| LU64050A1 (cs) | 1972-04-21 |
| JPS5516132B1 (cs) | 1980-04-30 |
| HU167518B (cs) | 1975-10-28 |
| DE2150808A1 (de) | 1972-04-20 |
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