GB826979A - Improvements in or relating to polymeric materials - Google Patents
Improvements in or relating to polymeric materialsInfo
- Publication number
- GB826979A GB826979A GB25144/56A GB2514456A GB826979A GB 826979 A GB826979 A GB 826979A GB 25144/56 A GB25144/56 A GB 25144/56A GB 2514456 A GB2514456 A GB 2514456A GB 826979 A GB826979 A GB 826979A
- Authority
- GB
- United Kingdom
- Prior art keywords
- cyclobutene
- methyl
- chloride
- dicarboxylic acid
- compound
- 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 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 9
- -1 bromo compound Chemical class 0.000 abstract 8
- 150000001875 compounds Chemical class 0.000 abstract 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 5
- 125000001047 cyclobutenyl group Chemical group C1(=CCC1)* 0.000 abstract 4
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 abstract 4
- 229920000642 polymer Polymers 0.000 abstract 4
- ZNDOZJSUYJAPPN-UHFFFAOYSA-N 1-aminocyclobut-2-ene-1-carboxylic acid Chemical compound NC1(C=CC1)C(=O)O ZNDOZJSUYJAPPN-UHFFFAOYSA-N 0.000 abstract 3
- AVPHQXWAMGTQPF-UHFFFAOYSA-N 1-methylcyclobutene Chemical compound CC1=CCC1 AVPHQXWAMGTQPF-UHFFFAOYSA-N 0.000 abstract 3
- 239000005057 Hexamethylene diisocyanate Substances 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- PUESTFGYLADOET-UHFFFAOYSA-N [2-(hydroxymethyl)-3-methylcyclobut-2-en-1-yl]methanol Chemical compound CC1=C(C(C1)CO)CO PUESTFGYLADOET-UHFFFAOYSA-N 0.000 abstract 3
- 150000001361 allenes Chemical class 0.000 abstract 3
- 229910021529 ammonia Inorganic materials 0.000 abstract 3
- 150000008064 anhydrides Chemical class 0.000 abstract 3
- 238000010438 heat treatment Methods 0.000 abstract 3
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 abstract 3
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 abstract 3
- OPIUEFASZGWACK-UHFFFAOYSA-N 3-(hydroxymethyl)cyclobutene-1-carboxylic acid Chemical compound OCC1CC(=C1)C(O)=O OPIUEFASZGWACK-UHFFFAOYSA-N 0.000 abstract 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 abstract 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 abstract 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 abstract 2
- 239000004952 Polyamide Substances 0.000 abstract 2
- 229920002396 Polyurea Polymers 0.000 abstract 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 abstract 2
- 239000003513 alkali Substances 0.000 abstract 2
- 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 2
- 238000009833 condensation Methods 0.000 abstract 2
- 230000005494 condensation Effects 0.000 abstract 2
- 238000004132 cross linking Methods 0.000 abstract 2
- WMPOZLHMGVKUEJ-UHFFFAOYSA-N decanedioyl dichloride Chemical compound ClC(=O)CCCCCCCCC(Cl)=O WMPOZLHMGVKUEJ-UHFFFAOYSA-N 0.000 abstract 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 abstract 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 abstract 2
- 230000003301 hydrolyzing effect Effects 0.000 abstract 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 abstract 2
- ZEFXEFHJKJHKQI-UHFFFAOYSA-N methyl 3-(aminomethyl)cyclobutene-1-carboxylate Chemical compound NCC1C=C(C1)C(=O)OC ZEFXEFHJKJHKQI-UHFFFAOYSA-N 0.000 abstract 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 abstract 2
- 238000006386 neutralization reaction Methods 0.000 abstract 2
- 229920002647 polyamide Polymers 0.000 abstract 2
- 229920000728 polyester Polymers 0.000 abstract 2
- 239000004814 polyurethane Substances 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 abstract 1
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 abstract 1
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 abstract 1
- MKAKJMTVPMLPQZ-UHFFFAOYSA-N 2-(methoxymethyl)-5-methylhexane-1,6-diamine Chemical compound COCC(CN)CCC(CN)C MKAKJMTVPMLPQZ-UHFFFAOYSA-N 0.000 abstract 1
- OJPDDQSCZGTACX-UHFFFAOYSA-N 2-[n-(2-hydroxyethyl)anilino]ethanol Chemical compound OCCN(CCO)C1=CC=CC=C1 OJPDDQSCZGTACX-UHFFFAOYSA-N 0.000 abstract 1
- RLSKTSGRGMPJLL-UHFFFAOYSA-N 3-(aminomethyl)cyclobutene-1-carboxylic acid Chemical compound NCC1C=C(C1)C(=O)O RLSKTSGRGMPJLL-UHFFFAOYSA-N 0.000 abstract 1
- PZADMZULTQOXJY-UHFFFAOYSA-N 3-aminocyclobutane-1-carbonitrile Chemical compound NC1CC(C#N)C1 PZADMZULTQOXJY-UHFFFAOYSA-N 0.000 abstract 1
- AQSOFHKMDGNCDW-UHFFFAOYSA-N 3-methylidenecyclobutene Chemical compound C=C1CC=C1 AQSOFHKMDGNCDW-UHFFFAOYSA-N 0.000 abstract 1
- WKVIEPDAIZBPPR-UHFFFAOYSA-N 3-methylidenecyclobutene-1-carbonitrile Chemical compound C=C1CC(C#N)=C1 WKVIEPDAIZBPPR-UHFFFAOYSA-N 0.000 abstract 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- QWQYHLWBZFGOKF-UHFFFAOYSA-N CC(C)=C.Br.Br Chemical compound CC(C)=C.Br.Br QWQYHLWBZFGOKF-UHFFFAOYSA-N 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 abstract 1
- MFESCIUQSIBMSM-UHFFFAOYSA-N I-BCP Chemical compound ClCCCBr MFESCIUQSIBMSM-UHFFFAOYSA-N 0.000 abstract 1
- 102000006835 Lamins Human genes 0.000 abstract 1
- 108010047294 Lamins Proteins 0.000 abstract 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 abstract 1
- XQQCCCJXAOBOJU-UHFFFAOYSA-N [Cl-].NC1(CC(C1)[N+](C)(C)C)C(=O)O Chemical compound [Cl-].NC1(CC(C1)[N+](C)(C)C)C(=O)O XQQCCCJXAOBOJU-UHFFFAOYSA-N 0.000 abstract 1
- BQRKJPCAGHFZJM-UHFFFAOYSA-M [I-].C=C1CC(C1)[N+](C)(C)C Chemical compound [I-].C=C1CC(C1)[N+](C)(C)C BQRKJPCAGHFZJM-UHFFFAOYSA-M 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 239000000853 adhesive Substances 0.000 abstract 1
- 230000001070 adhesive effect Effects 0.000 abstract 1
- 239000001361 adipic acid Substances 0.000 abstract 1
- 235000011037 adipic acid Nutrition 0.000 abstract 1
- PWAXUOGZOSVGBO-UHFFFAOYSA-N adipoyl chloride Chemical compound ClC(=O)CCCCC(Cl)=O PWAXUOGZOSVGBO-UHFFFAOYSA-N 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 235000019270 ammonium chloride Nutrition 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000011248 coating agent Substances 0.000 abstract 1
- 238000000576 coating method Methods 0.000 abstract 1
- UQFFSTQNDQYSAT-UHFFFAOYSA-N cyclobut-2-ene-1,1-dicarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CC=C1 UQFFSTQNDQYSAT-UHFFFAOYSA-N 0.000 abstract 1
- XKONTJWLWIJHHW-UHFFFAOYSA-N cyclobutene-1-carbonitrile Chemical compound N#CC1=CCC1 XKONTJWLWIJHHW-UHFFFAOYSA-N 0.000 abstract 1
- YQLZOAVZWJBZSY-UHFFFAOYSA-N decane-1,10-diamine Chemical compound NCCCCCCCCCCN YQLZOAVZWJBZSY-UHFFFAOYSA-N 0.000 abstract 1
- FOTKYAAJKYLFFN-UHFFFAOYSA-N decane-1,10-diol Chemical compound OCCCCCCCCCCO FOTKYAAJKYLFFN-UHFFFAOYSA-N 0.000 abstract 1
- 125000005442 diisocyanate group Chemical group 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 239000000835 fiber Substances 0.000 abstract 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 abstract 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 210000005053 lamin Anatomy 0.000 abstract 1
- 239000012280 lithium aluminium hydride Substances 0.000 abstract 1
- 229940018564 m-phenylenediamine Drugs 0.000 abstract 1
- CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 abstract 1
- 230000003472 neutralizing effect Effects 0.000 abstract 1
- 125000002560 nitrile group Chemical group 0.000 abstract 1
- 150000002978 peroxides Chemical class 0.000 abstract 1
- 229920002635 polyurethane Polymers 0.000 abstract 1
- 229920003226 polyurethane urea Polymers 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 159000000000 sodium salts Chemical class 0.000 abstract 1
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 abstract 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 abstract 1
- CURCMGVZNYCRNY-UHFFFAOYSA-N trimethylazanium;iodide Chemical compound I.CN(C)C CURCMGVZNYCRNY-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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/52—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
- C08G63/54—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation the acids or hydroxy compounds containing carbocyclic rings
-
- 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
- C08G18/67—Unsaturated compounds having active hydrogen
- C08G18/675—Low-molecular-weight compounds
- C08G18/676—Low-molecular-weight compounds containing the unsaturation at least partially in a non-aromatic carbocyclic ring
-
- 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
- C08G63/66—Polyesters containing oxygen in the form of ether groups
- C08G63/668—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/676—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
-
- 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
- C08G69/08—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from amino-carboxylic acids
-
- 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
-
- 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
- C08G85/00—General processes for preparing compounds provided for in this subclass
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyamides (AREA)
Abstract
The Specification describes the preparation of the following compounds containing a cyclobutene ring for use as intermediates in the manufacture of condensation polymers (see Group IV (a)): (a) 1-methyl-1-cyclobutene-2 : 3-dicarbonyl chloride is prepared from 1-methylenecyclobutene - 2 : 3 - dicarboxylic anhydride (the adduct of allene and maleic anhydride) by hydrolysing and isomerizing it with aqueous alkali and then acidifying with HCl to form the free cyclobutene dicarboxylic acid which is then treated with thionyl chloride; (b) 1-cyano-1-cyclobutene-3 : 4-dicarboxylic acid anhydride is prepared from 3-methylenecyclobutane-1 : 2-dicarboxylic acid anhydride (the adduct of allene and maleic anhydride) by treating it with ozone to convert the methylene group into the O= group, treating this compound with hydrogen cyanide and ammonia to give 3-amino-3-cyanocyclobutane-1 : 2-dicarboxylic anhydride, forming the trimethylammonium iodide salt of this compound and heating it with aqueous alkali; (c) 3-hydroxymethyl-1-carboxy-1-cyclobutene is made from 3-methylenecyclobutene-1-carbonitrile (the adduct of allene and acrylonitrile) by adding bromine to the double bond, hydrolysing with aqueous NaOH and neutralizing with HCl; (d) 1-methyl-3 : 3-dicarboethoxy-1-cyclobutene is made by adding isobutylene dibromide to diethyl malonate to form 1 - methylene - 3 : 3 - dicarboethoxycyclobutane, treating this compound with HI to give 1 - iodo - 1 - methyl - 3 : 3 - dicarboethoxycyclobutane and dehydrohalogenating the latter with triethylamine; (e) 1 : 1-di-(aminomethyl)-2-cyclobutene is made by reacting 1-bromo-3-chloropropane with dicyanomethane to form 1 : 1-dicyanocyclobutane, treating this compound with chlorine to give 2- and 3-chloro-1 : 1-dicyanocyclobutane, treating the mixture of isomers with triethylamine to give 1 : 1-dicyano-2-cyclobutene and reducing the latter with lithium aluminium hydride; (f) 3-(aminomethyl) - 1 - carbomethoxy - 1 - cyclobutene is made by the peroxide catalysed addition of hydrogen bromide to 3-methylene-1-cyclobutane-1-carbonitrile which is then reacted with ammonia to form 3-aminocyclobutane-1-carbonitrile, the free amino group of which is acetylated and the compound brominated in the position alphato the nitrile group. The resulting bromo compound is then hydrolysed with aqueous NaOH to the sodium salt of 3-(aminomethyl) - 1 - carboxy - 1 - cyclobutene which is converted to the ester by neutralization with HCl followed by esterification with methanol; (g) the N-carboanhydride of 1-amino-1-carboxy-2-cyclobutene is made by treating 1-methylene - 3 - cyclobutyltrimethylammonium iodide with ozone to convert the methylene group to the =O group and reacting the resulting compound with hydrogen cyanide and p ammonium chloride to form the 1-amino-1-cyano derivative. This compound is hydrolysed with HCl to form the hydrochloride of 1 - amino - 1 - carboxy - 3 - cyclobutyltrimethylammonium chloride, the quaternary ammonium radical of which is removed by heating with aqueous NaOH. After neutralization, the resulting 1-amino-1-carboxy-2-cyclobutene is converted to the N-carboanhydride by treatment with phosgene; (h) 1 : 2-di-(aminomethyl)-1-cyclobutene is made by treating the corresponding chloromethyl compound with ammonia. Specification 805,664 is referred to.ALSO:A cross-linkable condensation polyester, polyamide, polyurethane or polyurea has a chain structure containing recurring cyclobutene rings intralineal with the chain. Cross-linking, due to opening of the cyclobutene ring, is effected by heating the polymer at 100-325 DEG C. The cross-linking may be applied to the polymer when in the form of a shaped article, a fibre, a coating on a surface, an adhesive between lamin or as printed matter. The following polymers are exemplified:- Polyesters obtained from (a) dimethyl-1-cyclobutene-1:2-dicarboxylate and diphenylol propane, N,N-diethanol-aniline or ethylene-, triethylene-, trimethylene-, tetramethylene-, hexamethylene- or decamethylene-glycol; (b) the dimethyl ester of 3-methyl-1-cyclobutene-1:2-dicarboxylic acid, the dimethyl ester of 3:3-diethyl-1-cyclobutene-1:2-dicarboxylic acid or the dimethyl ester of 3:4-dimethyl-1-cyclobutene-1:2-dicarboxylic acid and hexamethylene glycol; (c) 1-methyl-1-cyclobutene-2:3-dicarbonyl chloride, sebacyl chloride and diphenylol propane; (d) 1-methyl-1-cyclobutene-2:3-dicarbonyl chloride and ethylene glycol; (e) 1 - methyl - 1 - cyclobutene - 2:3 - dicarbonyl chloride, terephthaloyl chloride and ethylene glycol; (f) 1-methyl-1-cyclobutene-2:3-dicarboxylic acid and ethylene glycol; (g) 1 - cyano - 1 - cyclobutene - 3:4 - dicarboxylic anhydride and ethylene glycol; (h) 1:2-di-(hydroxymethyl) - 1 - cyclobutene and malonic, succinic, maleic, adipic, suberic, terephthalic, p-phenylene diacetic or thioldibutyric acid or ester-forming derivatives thereof; (i) a hydroxyethylated 1:2-dihydroxymethyl-1-cyclobutene and adipic acid; (j) 3-hydroxymethyl-1-carboxy-1-cyclobutene. Polyamides obtained from (a) dimethyl-1-cyclobutene-1:2-dicarboxylate and ethylene-, hexamethylene-, 3 - methylhexamethylene-, decamethylene- or m-phenylene-diamine; (h) 1 - methyl - 1 - cyclobutene - 2:3 - dicarbonyl chloride, sebacyl chloride and 2-methoxymethyl-5 - methylhexamethylenediamine; (c) 1-methyl-1 - cyclobutene - 2:3 - dicarboxylic acid, 3:3-diethyl - 1 - cyclobutene - 1:2 - dicarboxylic acid or 3:4 - dimethyl - 1 - cyclobutene - 1:2 - dicarboxylic acid (or amide-forming derivatives thereof) and hexamethylene diamine; (d) 1-methyl - 3:3 - dicarboethoxy - 1 - cyclobutene and ethylene diamine; (e) 1:1-di(aminomethyl)-2-cyclobutene and adipyl chloride; (f) 3 - (aminomethyl) - 1 - carbomethoxy - 1 - cyclobutene; (g) the N-carboanhydride of 1-amino - 1 - carboxy - 2 - cyclobutene. Polyurethanes obtained from (a) 1:2-di-(hydroxymethyl) - 1 - cyclobutene and hexamethylene diisocyanate; (b) 3-methyl-2-cyclobutene-1,2-bis-methanol and hexamethylene diisocyanate; (c) 3-methyl-2-cyclobutene-1.2-bis-methanol, ethylene glycol and 3-methyl-2-cyclobutene-1,2-bismethanol; (d) a diisocyanate having a cyclobutene ring and a glycol (both unspecified). Polyureas obtained from 1:2-di-(aminomethyl) - 1 - cyclobutene and hexamethylene diisocyanate. Specification 805,664 is referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US826979XA | 1955-08-16 | 1955-08-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB826979A true GB826979A (en) | 1960-01-27 |
Family
ID=22172831
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB25144/56A Expired GB826979A (en) | 1955-08-16 | 1956-08-16 | Improvements in or relating to polymeric materials |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB826979A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2267438A (en) * | 1992-05-28 | 1993-12-08 | British Tech Group | Alicyclic diamine plant fungicides |
-
1956
- 1956-08-16 GB GB25144/56A patent/GB826979A/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2267438A (en) * | 1992-05-28 | 1993-12-08 | British Tech Group | Alicyclic diamine plant fungicides |
| GB2267438B (en) * | 1992-05-28 | 1995-04-19 | British Tech Group | Alicyclic diamine fungicides |
| US5464873A (en) * | 1992-05-28 | 1995-11-07 | British Technology Group Limited | Alicyclic diamine fungicides |
| US5583261A (en) * | 1992-05-28 | 1996-12-10 | British Technology Group Ltd. | Alicyclic diamine fungicides |
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