GB1116379A - Copolyimides - Google Patents
CopolyimidesInfo
- Publication number
- GB1116379A GB1116379A GB28914/65A GB2891465A GB1116379A GB 1116379 A GB1116379 A GB 1116379A GB 28914/65 A GB28914/65 A GB 28914/65A GB 2891465 A GB2891465 A GB 2891465A GB 1116379 A GB1116379 A GB 1116379A
- Authority
- GB
- United Kingdom
- Prior art keywords
- diamine
- links
- diol
- anhydride
- bis
- 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
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 10
- 150000004985 diamines Chemical class 0.000 abstract 9
- 150000002009 diols Chemical class 0.000 abstract 8
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 6
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 abstract 6
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 abstract 5
- 239000004721 Polyphenylene oxide Substances 0.000 abstract 5
- 150000003949 imides Chemical class 0.000 abstract 5
- 229920000570 polyether Polymers 0.000 abstract 5
- 229920000642 polymer Chemical group 0.000 abstract 5
- -1 polytetramethylene Polymers 0.000 abstract 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 4
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 abstract 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 abstract 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 3
- 239000004202 carbamide Substances 0.000 abstract 3
- 239000003054 catalyst Substances 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 150000002148 esters Chemical class 0.000 abstract 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 abstract 3
- 229920000728 polyester Polymers 0.000 abstract 3
- 239000002904 solvent Substances 0.000 abstract 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 3
- OHLKMGYGBHFODF-UHFFFAOYSA-N 1,4-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=C(CN=C=O)C=C1 OHLKMGYGBHFODF-UHFFFAOYSA-N 0.000 abstract 2
- ROHUXHMNZLHBSF-UHFFFAOYSA-N 1,4-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1CCC(CN=C=O)CC1 ROHUXHMNZLHBSF-UHFFFAOYSA-N 0.000 abstract 2
- KHFMBSMOWZLHOZ-UHFFFAOYSA-N 2-cyclononyloxonane Chemical compound C1CCCCCCCC1C1OCCCCCCC1 KHFMBSMOWZLHOZ-UHFFFAOYSA-N 0.000 abstract 2
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 abstract 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 abstract 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 125000001931 aliphatic group Chemical group 0.000 abstract 2
- 150000001408 amides Chemical class 0.000 abstract 2
- 150000008064 anhydrides Chemical class 0.000 abstract 2
- AVKNGPAMCBSNSO-UHFFFAOYSA-N cyclohexylmethanamine Chemical compound NCC1CCCCC1 AVKNGPAMCBSNSO-UHFFFAOYSA-N 0.000 abstract 2
- 125000005442 diisocyanate group Chemical group 0.000 abstract 2
- ALOUNLDAKADEEB-UHFFFAOYSA-N dimethyl sebacate Chemical compound COC(=O)CCCCCCCCC(=O)OC ALOUNLDAKADEEB-UHFFFAOYSA-N 0.000 abstract 2
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 abstract 2
- 229940113088 dimethylacetamide Drugs 0.000 abstract 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 abstract 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 abstract 2
- 239000002480 mineral oil Substances 0.000 abstract 2
- 235000010446 mineral oil Nutrition 0.000 abstract 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 abstract 2
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- VNMOIBZLSJDQEO-UHFFFAOYSA-N 1,10-diisocyanatodecane Chemical compound O=C=NCCCCCCCCCCN=C=O VNMOIBZLSJDQEO-UHFFFAOYSA-N 0.000 abstract 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 abstract 1
- 229930185605 Bisphenol Natural products 0.000 abstract 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 abstract 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 abstract 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- 229920002732 Polyanhydride Polymers 0.000 abstract 1
- 239000004642 Polyimide Substances 0.000 abstract 1
- 229920002396 Polyurea Polymers 0.000 abstract 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical group CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 abstract 1
- ORLQHILJRHBSAY-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1(CO)CCCCC1 ORLQHILJRHBSAY-UHFFFAOYSA-N 0.000 abstract 1
- GKXVJHDEWHKBFH-UHFFFAOYSA-N [2-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC=C1CN GKXVJHDEWHKBFH-UHFFFAOYSA-N 0.000 abstract 1
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 abstract 1
- OXIKYYJDTWKERT-UHFFFAOYSA-N [4-(aminomethyl)cyclohexyl]methanamine Chemical compound NCC1CCC(CN)CC1 OXIKYYJDTWKERT-UHFFFAOYSA-N 0.000 abstract 1
- ZLHRQERTTJVJSJ-UHFFFAOYSA-N acetic acid;benzene-1,4-diol Chemical compound CC(O)=O.CC(O)=O.OC1=CC=C(O)C=C1 ZLHRQERTTJVJSJ-UHFFFAOYSA-N 0.000 abstract 1
- 125000002723 alicyclic group Chemical group 0.000 abstract 1
- 125000003368 amide group Chemical group 0.000 abstract 1
- 150000001413 amino acids Chemical class 0.000 abstract 1
- 150000001414 amino alcohols Chemical class 0.000 abstract 1
- 230000001588 bifunctional effect Effects 0.000 abstract 1
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 abstract 1
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 abstract 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 abstract 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 abstract 1
- 150000001733 carboxylic acid esters Chemical class 0.000 abstract 1
- YQLZOAVZWJBZSY-UHFFFAOYSA-N decane-1,10-diamine Chemical compound NCCCCCCCCCCN YQLZOAVZWJBZSY-UHFFFAOYSA-N 0.000 abstract 1
- 150000001991 dicarboxylic acids Chemical class 0.000 abstract 1
- VNGOYPQMJFJDLV-UHFFFAOYSA-N dimethyl benzene-1,3-dicarboxylate Chemical compound COC(=O)C1=CC=CC(C(=O)OC)=C1 VNGOYPQMJFJDLV-UHFFFAOYSA-N 0.000 abstract 1
- 229940014772 dimethyl sebacate Drugs 0.000 abstract 1
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 abstract 1
- 239000000835 fiber Substances 0.000 abstract 1
- ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 abstract 1
- 150000002334 glycols Chemical class 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 abstract 1
- 150000001261 hydroxy acids Chemical class 0.000 abstract 1
- 125000005462 imide group Chemical group 0.000 abstract 1
- 125000005647 linker group Chemical group 0.000 abstract 1
- 229910052744 lithium Inorganic materials 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000000178 monomer Substances 0.000 abstract 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 abstract 1
- 229920000515 polycarbonate Polymers 0.000 abstract 1
- 239000004417 polycarbonate Substances 0.000 abstract 1
- 229920006149 polyester-amide block copolymer Polymers 0.000 abstract 1
- 229920000139 polyethylene terephthalate Polymers 0.000 abstract 1
- 239000005020 polyethylene terephthalate Substances 0.000 abstract 1
- 229920001721 polyimide Polymers 0.000 abstract 1
- 229920006324 polyoxymethylene Polymers 0.000 abstract 1
- 229920002635 polyurethane Polymers 0.000 abstract 1
- 239000004814 polyurethane Substances 0.000 abstract 1
- HKJYVRJHDIPMQB-UHFFFAOYSA-N propan-1-olate;titanium(4+) Chemical compound CCCO[Ti](OCCC)(OCCC)OCCC HKJYVRJHDIPMQB-UHFFFAOYSA-N 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 abstract 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/16—Polyester-imides
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3819—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen
- C08G18/3842—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen containing heterocyclic rings having at least one nitrogen atom in the ring
- C08G18/3844—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen containing heterocyclic rings having at least one nitrogen atom in the ring containing one nitrogen atom in the ring
- C08G18/3846—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen containing heterocyclic rings having at least one nitrogen atom in the ring containing one nitrogen atom in the ring containing imide groups
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
- C08G63/685—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen
- C08G63/6854—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/6856—Dicarboxylic acids and dihydroxy compounds
-
- 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
- C08G67/00—Macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing oxygen or oxygen and carbon, not provided for in groups C08G2/00 - C08G65/00
-
- 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
- C08G71/00—Macromolecular compounds obtained by reactions forming a ureide or urethane link, otherwise, than from isocyanate radicals in the main chain of the macromolecule
-
- 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1067—Wholly aromatic polyimides, i.e. having both tetracarboxylic and diamino moieties aromatically bound
-
- 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1075—Partially aromatic polyimides
- C08G73/1082—Partially aromatic polyimides wholly aromatic in the tetracarboxylic moiety
-
- 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/14—Polyamide-imides
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
Polyimides have a main chain composed of organic residues interconnected by imide links and by carboxylic ester, urethane, carboxylic anhydride, carbonate, urea or amide links, the ester links when present being derived from a dihydroxy compound or an aliphatic monohydroxy compound, the urethane links being derived from a dihydroxy compound free from hydrolysable links and the amide groups being accompanied by at least one of the other linking groups. The organic residues may be C1- 40 aliphatic, C3- 20 alicyclic or polyalicyclic or C6- 20 aromatic radicals or polymer residues. Elastomeric polymers may contain 40-91% of organic residues derived from a polymer, e.g. a polyester, polyether or polyformaldehyde, of m.p. less than 45 DEG C. and M.W. 500-5000 and a fibre-forming polymer of m.p. above 200 DEG C. joined by urethane links. The polymers may be prepared from a bifunctional monomer containing 1-4 imide links. These may be reacted with dicarboxylic acids, amino acids, hydroxyacids, aminoalcohols, aminophenols, glycols, diamines, phosgene or diisocyanates. Ester links may be formed by ester-interchange at 0-300 DEG C. in the presence of a catalyst or by use of an acid chloride. Urea links may be formed from a diamine and a diisocyanate at 0-200 DEG C., the imide group being present in either reactant, a diamine and phosgene, CO2 or urea or a diamine and a urethane. Anhydride links may be formed at 0-300 DEG C. from an imide-containing dicarboxylic acid, a non-imide containing dicarboxylic acid and acetic anhydride in pyridine. Carbonate links may be formed at 300 DEG C. from an imide containing diol, e.g. a bis-phenol, and a phosgene or a bischloroformate of a diol. Urethane links may be formed at 30-150 DEG C. from an imido-diisocyanate and a diol or from a bis-chloroformate of a diol and a diamine. The diol may be a polyester or polyether. Products containing ester and amide links may be formed. The products may be linear and fibre forming. In Examples (6-14, 16-23 and 41) polyesters are formed from: <FORM:1116379/C3/1> butane diol, cyclohexanedimethanol, ethylene glycol, polytetramethylene glycol <FORM:1116379/C3/2> <FORM:1116379/C3/3> sebacic acid, dimethyl terephthalate, <FORM:1116379/C3/4> dimethyl sebacate, dimethyl isophthalate and <FORM:1116379/C3/5> using titanium tetrapropoxide and titanium tetrabutoxide as catalyst. In Examples (15, 32, 42 and 43) polycarbonates are prepared from diphenyl carbonate, diol IV, phenol, a polyether of tetrahydrofuran and oxa-bicyclononane bisphenol-A and phosgene using pyridine and methylene chloride as solvents and lithium in mineral oil as a catalyst. In Examples (24-27 and 36-40) polyurethanes are prepared from diol IV, tolylene diisocyanate, p-xylylene diisocyanate, <FORM:1116379/C3/6> the bischloroformate of neopentylene glycol, <FORM:1116379/C3/7> polytetramethylene glycol, <FORM:1116379/C3/8> a polyether of tetrahydrofuran and oxabicyclononane, poly-(ethylene terephthalate) containing some propylene glycol residues, 1,4-bis-(isocyanatomethyl) cyclohexane, bis-(4 - isocyanatophenyl) methane, <FORM:1116379/C3/9> and <FORM:1116379/C3/100> using dimethylacetamide and dimethylformamide, as solvents and aq. NaOH as an acid acceptor. In Examples (28-30) polyesteramides are formed from dicarboxylic acid I, 1-hydroxymethyl, 4 - aminomethyl - cyclohexane, ethylene glycol, hexamethylene diamine, diol IV, xylylene diamine and sebacic acid in the presence of water. In Example (31) a polyanhydride was formed from dicarboxylic acid I, hydroquinone diacetic acid and acetic anhydride. In Examples (33-36 and 38-40) polyureas are formed from decamethylene diisocyanate, <FORM:1116379/C3/111> bis - (4 - isocyanatophenyl) methane, diamine X, hexamethylene diisocyanate, decamethylene diamine and diamine VIII, poly-(tetramethylene) glycol, p-xylylene diisocyanate, a polyether of tetrahydrofuran and oxabicyclononane, diamine IX and 1,4-bis-(isocyanatomethyl) cyclohexane using dimethylformamide and dimethyl acetamide as solvents.ALSO:In Example 1 <FORM:1116379/C2/1> was prepared from 1,4-bis (aminomethyl) cyclohexane and trimellitic anhydride by heating in DMF and later in mineral oil under N2. In Example 2 the procedure was repeated replacing the diamine by m-xylylene diamine and hexamethylene diamine. In Example 3 <FORM:1116379/C2/2> was prepared from 1-hydroxymethyl, 4-aminomethylcyclohexane and pyromellitic anhydride in DMF, the resulting solution being poured into water to precipitate the product. In Example 4 trimellitic acid/anhydride was heated in diphenyl ether to convert the acid to anhydride and the resulting solution condensed with hexamethylene diamine. In Example 5 trimellitic anhydride was condensed with epsilon-caprolactam.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US38154564A | 1964-07-09 | 1964-07-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1116379A true GB1116379A (en) | 1968-06-06 |
Family
ID=23505440
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB28914/65A Expired GB1116379A (en) | 1964-07-09 | 1965-07-08 | Copolyimides |
Country Status (2)
| Country | Link |
|---|---|
| FR (1) | FR1450704A (en) |
| GB (1) | GB1116379A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5124512B1 (en) * | 1971-05-10 | 1976-07-24 | ||
| EP0267773A3 (en) * | 1986-11-10 | 1989-07-26 | E.I. Du Pont De Nemours And Company | Elastomers |
| WO2015193682A1 (en) * | 2014-06-20 | 2015-12-23 | Dupont Teijin Films U.S. Limited Partnership | Copolyesterimides comprising bis(2-hydroxyalkyl)-2,2'-(1,4-phenylene)bis(1,3-dioxoisoindoline-5-carboxylate) and articles made therefrom |
| US9840590B2 (en) | 2013-06-18 | 2017-12-12 | Dupont Teijin Films U.S. Limited Partnership | Copolyesterimides derived from N,N′-bis-(hydroxyalkyl)-benzophenone-3,3′,4,4′-tetracarboxylic diimide and films made therefrom |
| CN107531626A (en) * | 2015-04-07 | 2018-01-02 | 尤尼吉可株式会社 | The manufacture method of double imide dicarboxylic acids |
| US10584212B2 (en) | 2015-04-07 | 2020-03-10 | Unitika Ltd. | Polyamide-imide, raw material salt of polyamide-imide, and production method thereof |
| CN115557874A (en) * | 2022-11-09 | 2023-01-03 | 海洋化工研究院有限公司 | Weather-resistant compound containing polyimide structure, anticorrosive paint, and preparation and application thereof |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5136868B2 (en) * | 1974-05-01 | 1976-10-12 | ||
| JPS5234756B2 (en) * | 1974-05-01 | 1977-09-05 | ||
| CN110437445B (en) * | 2019-08-21 | 2021-11-16 | 中仑塑业（福建）有限公司 | Polyamide resin and preparation method and application thereof |
-
1965
- 1965-07-08 GB GB28914/65A patent/GB1116379A/en not_active Expired
- 1965-07-09 FR FR24057A patent/FR1450704A/en not_active Expired
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5124512B1 (en) * | 1971-05-10 | 1976-07-24 | ||
| EP0267773A3 (en) * | 1986-11-10 | 1989-07-26 | E.I. Du Pont De Nemours And Company | Elastomers |
| US10377862B2 (en) | 2013-06-18 | 2019-08-13 | Dupont Teijin Films U.S. Limited Partnership | Copolyesterimides derived from N,N′-bis-(hydroxyalkyl)-benzophenone-3,3′,4,4′-tetracarboxylic diimide and films made therefrom |
| US9840590B2 (en) | 2013-06-18 | 2017-12-12 | Dupont Teijin Films U.S. Limited Partnership | Copolyesterimides derived from N,N′-bis-(hydroxyalkyl)-benzophenone-3,3′,4,4′-tetracarboxylic diimide and films made therefrom |
| WO2015193682A1 (en) * | 2014-06-20 | 2015-12-23 | Dupont Teijin Films U.S. Limited Partnership | Copolyesterimides comprising bis(2-hydroxyalkyl)-2,2'-(1,4-phenylene)bis(1,3-dioxoisoindoline-5-carboxylate) and articles made therefrom |
| CN106488944A (en) * | 2014-06-20 | 2017-03-08 | 杜邦帝人薄膜美国有限公司 | Copolyester imide containing double (2 hydroxy alkyls) 2,2 ' (1,4 phenylene) double (1,3 dioxoisoindolin 5 carboxylate) and product prepared therefrom |
| US10450411B2 (en) | 2014-06-20 | 2019-10-22 | Dupont Teijin Films U.S. Limited Partnership | Copolyesterimides comprising bis(2-hydroxyalkyl)-2,2′-(1,4-phenylene)bis(1,3-dioxoisoindoline-5-carboxylate) and articles made therefrom |
| US20180086704A1 (en) * | 2015-04-07 | 2018-03-29 | Unitika Ltd. | Method for producing bisimide dicarboxylic acid |
| CN107531626A (en) * | 2015-04-07 | 2018-01-02 | 尤尼吉可株式会社 | The manufacture method of double imide dicarboxylic acids |
| US10501415B2 (en) * | 2015-04-07 | 2019-12-10 | Unitika Ltd. | Method for producing bisimide dicarboxylic acid |
| US10584212B2 (en) | 2015-04-07 | 2020-03-10 | Unitika Ltd. | Polyamide-imide, raw material salt of polyamide-imide, and production method thereof |
| CN107531626B (en) * | 2015-04-07 | 2020-08-11 | 尤尼吉可株式会社 | The production method of bisimide dicarboxylic acid |
| CN115557874A (en) * | 2022-11-09 | 2023-01-03 | 海洋化工研究院有限公司 | Weather-resistant compound containing polyimide structure, anticorrosive paint, and preparation and application thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1450704A (en) | 1966-06-24 |
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