CH586246A5 - Heat stable polymers for paint, electrical and building inds. - and comprising addn. prods. of polyimides, polyphenols and amines - Google Patents

Heat stable polymers for paint, electrical and building inds. - and comprising addn. prods. of polyimides, polyphenols and amines

Info

Publication number: CH586246A5
Authority: CH; Switzerland
Prior art keywords: formula; prods; bis; polyimides; esp
Prior art date: 1973-12-21

Application number

CH1804773A

Other languages

German (de)

English (en)

Original Assignee

Ciba Geigy Ag

Priority date (The priority date 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 date listed.)

1973-12-21

Filing date

1973-12-21

Publication date

1977-03-31

1973-12-21 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1973-12-21 Priority to CH1804773A priority Critical patent/CH586246A5/de

1974-12-18 Priority to US05/534,105 priority patent/US4038251A/en

1974-12-18 Priority to DE2459925A priority patent/DE2459925C2/de

1974-12-19 Priority to CA216,444A priority patent/CA1046191A/en

1974-12-20 Priority to ES433165A priority patent/ES433165A1/es

1974-12-20 Priority to GB55154/74A priority patent/GB1492759A/en

1974-12-20 Priority to AT1022474A priority patent/AT337990B/de

1974-12-20 Priority to AU76705/74A priority patent/AU488753B2/en

1974-12-20 Priority to IT3089274A priority patent/IT1027942B/it

1974-12-20 Priority to ZA00748135A priority patent/ZA748135B/xx

1974-12-20 Priority to BE151824A priority patent/BE823720A/xx

1974-12-20 Priority to DD183282A priority patent/DD117887A5/xx

1974-12-20 Priority to DD190122A priority patent/DD122256A5/xx

1974-12-20 Priority to NL7416706A priority patent/NL7416706A/xx

1974-12-20 Priority to FR7442227A priority patent/FR2278723A1/fr

1974-12-21 Priority to JP49147511A priority patent/JPS5839169B2/ja

1975-08-22 Priority to FR7525995A priority patent/FR2275503A1/fr

1977-03-31 Publication of CH586246A5 publication Critical patent/CH586246A5/de

1983-04-11 Priority to JP58063527A priority patent/JPS60364B2/ja

Links

239000004642 Polyimide Substances 0.000 title claims abstract description 20
229920001721 polyimide Polymers 0.000 title claims abstract description 20
150000001412 amines Chemical class 0.000 title abstract description 6
239000003973 paint Substances 0.000 title abstract 2
229920000642 polymer Polymers 0.000 title description 4
150000008442 polyphenolic compounds Chemical class 0.000 title description 3
235000013824 polyphenols Nutrition 0.000 title description 3
239000003054 catalyst Substances 0.000 claims abstract description 14
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 12
150000002989 phenols Chemical class 0.000 claims abstract description 11
229920003986 novolac Polymers 0.000 claims abstract description 8
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims abstract description 6
GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims abstract description 6
238000000034 method Methods 0.000 claims description 33
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 claims description 14
150000001875 compounds Chemical class 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
125000005462 imide group Chemical group 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
238000002360 preparation method Methods 0.000 claims description 3
150000003856 quaternary ammonium compounds Chemical class 0.000 claims description 3
XQUPVDVFXZDTLT-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C(C=C1)=CC=C1CC1=CC=C(N2C(C=CC2=O)=O)C=C1 XQUPVDVFXZDTLT-UHFFFAOYSA-N 0.000 claims description 2
150000001339 alkali metal compounds Chemical class 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 2
230000001419 dependent effect Effects 0.000 claims 2
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract description 9
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 abstract description 6
238000005266 casting Methods 0.000 abstract description 5
239000000376 reactant Substances 0.000 abstract description 5
150000003949 imides Chemical class 0.000 abstract description 4
238000007493 shaping process Methods 0.000 abstract description 4
239000000853 adhesive Substances 0.000 abstract description 2
230000001070 adhesive effect Effects 0.000 abstract description 2
-1 aliphatic dithiol Chemical class 0.000 abstract description 2
231100000331 toxic Toxicity 0.000 abstract description 2
230000002588 toxic effect Effects 0.000 abstract description 2
125000003118 aryl group Chemical group 0.000 abstract 1
238000000576 coating method Methods 0.000 abstract 1
ATUOYWHBWRKTHZ-UHFFFAOYSA-N dimethylmethane Natural products CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 abstract 1
PVAONLSZTBKFKM-UHFFFAOYSA-N diphenylmethanediol Chemical compound C=1C=CC=CC=1C(O)(O)C1=CC=CC=C1 PVAONLSZTBKFKM-UHFFFAOYSA-N 0.000 abstract 1
238000010030 laminating Methods 0.000 abstract 1
239000001294 propane Substances 0.000 abstract 1
229920005989 resin Polymers 0.000 abstract 1
239000011347 resin Substances 0.000 abstract 1
231100000419 toxicity Toxicity 0.000 abstract 1
230000001988 toxicity Effects 0.000 abstract 1
IEDVJHCEMCRBQM-UHFFFAOYSA-N trimethoprim Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 IEDVJHCEMCRBQM-UHFFFAOYSA-N 0.000 abstract 1
229910052757 nitrogen Inorganic materials 0.000 description 22
239000000047 product Substances 0.000 description 11
239000000126 substance Substances 0.000 description 10
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 8
239000000203 mixture Substances 0.000 description 8
238000004519 manufacturing process Methods 0.000 description 7
239000000243 solution Substances 0.000 description 7
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
239000007858 starting material Substances 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
150000003923 2,5-pyrrolediones Chemical class 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
238000010276 construction Methods 0.000 description 3
239000003365 glass fiber Substances 0.000 description 3
238000000227 grinding Methods 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
239000000155 melt Substances 0.000 description 3
235000006408 oxalic acid Nutrition 0.000 description 3
239000000843 powder Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
229910052717 sulfur Inorganic materials 0.000 description 3
ZYPZVOKVDNSKLP-UHFFFAOYSA-N tris(4-aminophenyl) phosphate Chemical compound C1=CC(N)=CC=C1OP(=O)(OC=1C=CC(N)=CC=1)OC1=CC=C(N)C=C1 ZYPZVOKVDNSKLP-UHFFFAOYSA-N 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
JNRLEMMIVRBKJE-UHFFFAOYSA-N 4,4'-Methylenebis(N,N-dimethylaniline) Chemical compound C1=CC(N(C)C)=CC=C1CC1=CC=C(N(C)C)C=C1 JNRLEMMIVRBKJE-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
239000004305 biphenyl Substances 0.000 description 2
PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
150000004985 diamines Chemical class 0.000 description 2
150000004662 dithiols Chemical class 0.000 description 2
239000000945 filler Substances 0.000 description 2
239000006260 foam Substances 0.000 description 2
238000007731 hot pressing Methods 0.000 description 2
239000000463 material Substances 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
239000006082 mold release agent Substances 0.000 description 2
238000000465 moulding Methods 0.000 description 2
125000004430 oxygen atom Chemical group O* 0.000 description 2
229920000768 polyamine Polymers 0.000 description 2
150000003141 primary amines Chemical class 0.000 description 2
WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
239000011593 sulfur Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
239000002759 woven fabric Substances 0.000 description 2
AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 description 1
RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 description 1
VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
VWGKEVWFBOUAND-UHFFFAOYSA-N 4,4'-thiodiphenol Chemical compound C1=CC(O)=CC=C1SC1=CC=C(O)C=C1 VWGKEVWFBOUAND-UHFFFAOYSA-N 0.000 description 1
NZGQHKSLKRFZFL-UHFFFAOYSA-N 4-(4-hydroxyphenoxy)phenol Chemical compound C1=CC(O)=CC=C1OC1=CC=C(O)C=C1 NZGQHKSLKRFZFL-UHFFFAOYSA-N 0.000 description 1
RQCACQIALULDSK-UHFFFAOYSA-N 4-(4-hydroxyphenyl)sulfinylphenol Chemical compound C1=CC(O)=CC=C1S(=O)C1=CC=C(O)C=C1 RQCACQIALULDSK-UHFFFAOYSA-N 0.000 description 1
MBUAAMOJATXYKR-UHFFFAOYSA-N 4-bis(4-aminophenoxy)phosphinothioyloxyaniline Chemical compound C1=CC(N)=CC=C1OP(=S)(OC=1C=CC(N)=CC=1)OC1=CC=C(N)C=C1 MBUAAMOJATXYKR-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
JPYHHZQJCSQRJY-UHFFFAOYSA-N Phloroglucinol Natural products CCC=CCC=CCC=CCC=CCCCCC(=O)C1=C(O)C=C(O)C=C1O JPYHHZQJCSQRJY-UHFFFAOYSA-N 0.000 description 1
241000158147 Sator Species 0.000 description 1
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
238000006887 Ullmann reaction Methods 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
150000008043 acidic salts Chemical class 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000000654 additive Substances 0.000 description 1
239000003513 alkali Substances 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
GGNQRNBDZQJCCN-UHFFFAOYSA-N benzene-1,2,4-triol Chemical compound OC1=CC=C(O)C(O)=C1 GGNQRNBDZQJCCN-UHFFFAOYSA-N 0.000 description 1
SMTUJUHULKBTBS-UHFFFAOYSA-N benzyl(trimethyl)azanium;methanolate Chemical compound [O-]C.C[N+](C)(C)CC1=CC=CC=C1 SMTUJUHULKBTBS-UHFFFAOYSA-N 0.000 description 1
NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical group C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 description 1
CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
235000013539 calcium stearate Nutrition 0.000 description 1
239000008116 calcium stearate Substances 0.000 description 1
229940075614 colloidal silicon dioxide Drugs 0.000 description 1
238000002485 combustion reaction Methods 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
238000009833 condensation Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000004132 cross linking Methods 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000006735 deficit Effects 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000000975 dye Substances 0.000 description 1
238000004870 electrical engineering Methods 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000000835 fiber Substances 0.000 description 1
239000003063 flame retardant Substances 0.000 description 1
235000013312 flour Nutrition 0.000 description 1
238000005469 granulation Methods 0.000 description 1
230000003179 granulation Effects 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
235000011167 hydrochloric acid Nutrition 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
238000003475 lamination Methods 0.000 description 1
239000007788 liquid Substances 0.000 description 1
FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
239000010445 mica Substances 0.000 description 1
229910052618 mica group Inorganic materials 0.000 description 1
239000011812 mixed powder Substances 0.000 description 1
OOHAUGDGCWURIT-UHFFFAOYSA-N n,n-dipentylpentan-1-amine Chemical compound CCCCCN(CCCCC)CCCCC OOHAUGDGCWURIT-UHFFFAOYSA-N 0.000 description 1
PCILLCXFKWDRMK-UHFFFAOYSA-N naphthalene-1,4-diol Chemical compound C1=CC=C2C(O)=CC=C(O)C2=C1 PCILLCXFKWDRMK-UHFFFAOYSA-N 0.000 description 1
239000004745 nonwoven fabric Substances 0.000 description 1
239000003921 oil Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000008520 organization Effects 0.000 description 1
229920001568 phenolic resin Polymers 0.000 description 1
239000005011 phenolic resin Substances 0.000 description 1
QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 1
229960001553 phloroglucinol Drugs 0.000 description 1
239000000049 pigment Substances 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
229920003192 poly(bis maleimide) Polymers 0.000 description 1
238000006068 polycondensation reaction Methods 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
238000011417 postcuring Methods 0.000 description 1
229940079877 pyrogallol Drugs 0.000 description 1
239000010453 quartz Substances 0.000 description 1
239000002994 raw material Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000007790 solid phase Substances 0.000 description 1
239000000758 substrate Substances 0.000 description 1
KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical group O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
229950011008 tetrachloroethylene Drugs 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
238000012719 thermal polymerization Methods 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
239000001993 wax Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc 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
- 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
- C08G73/12—Unsaturated polyimide precursors
- C08G73/126—Unsaturated polyimide precursors the unsaturated precursors being wholly aromatic
- C08G73/127—Unsaturated polyimide precursors the unsaturated precursors being wholly aromatic containing oxygen in the form of ether bonds in the main chain
- 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
- C08G73/12—Unsaturated polyimide precursors
- 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
- C08G73/12—Unsaturated polyimide precursors
- C08G73/125—Unsaturated polyimide precursors the unsaturated precursors containing atoms other than carbon, hydrogen, oxygen or nitrogen in the main chain

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)

CH1804773A 1973-12-21 1973-12-21 Heat stable polymers for paint, electrical and building inds. - and comprising addn. prods. of polyimides, polyphenols and amines CH586246A5 (en)

Priority Applications (18)

Application Number	Priority Date	Filing Date	Title
CH1804773A CH586246A5 (en)	1973-12-21	1973-12-21	Heat stable polymers for paint, electrical and building inds. - and comprising addn. prods. of polyimides, polyphenols and amines
US05/534,105 US4038251A (en)	1973-12-21	1974-12-18	Process for the manufacture of polyaddition products containing imide groups by reaction of polymaleimides with polyhydric phenols using amine catalyst
DE2459925A DE2459925C2 (de)	1973-12-21	1974-12-18	Verfahren zur Herstellung von Imidgruppen aufweisenden Polyadditionsprodukten
CA216,444A CA1046191A (en)	1973-12-21	1974-12-19	Process for the manufacture of polyaddition products containing imide groups
ZA00748135A ZA748135B (en)	1973-12-21	1974-12-20	Process for the manufacture of polyaddition products containing imide groups
DD183282A DD117887A5 (ja)	1973-12-21	1974-12-20
AT1022474A AT337990B (de)	1973-12-21	1974-12-20	Verfahren zur herstellung von imidgruppen aufweisenden polyadditionsprodukten
AU76705/74A AU488753B2 (en)		1974-12-20	Process forthe manufacture of polyaddition products containing imide groups
IT3089274A IT1027942B (it)	1973-12-21	1974-12-20	Procedimento per la preparazione di prodotti di poliaddizione che presentano gruppi immidici
ES433165A ES433165A1 (es)	1973-12-21	1974-12-20	Procedimiento para la preparacion de productos de poliadi- cion provistos de grupos imidicos.
BE151824A BE823720A (fr)	1973-12-21	1974-12-20	Procede de preparation de produits de polyaddition portant des groupes imides
GB55154/74A GB1492759A (en)	1973-12-21	1974-12-20	Process for the manufacture of polyaddition products containing imide groups
DD190122A DD122256A5 (ja)	1973-12-21	1974-12-20
NL7416706A NL7416706A (nl)	1973-12-21	1974-12-20	Werkwijze voor de bereiding van imidegroepen bevattende polyadditieprodukten.
FR7442227A FR2278723A1 (fr)	1973-12-21	1974-12-20	Produits de polyaddition de polyimides et de polyphenols, et leur procede de preparation
JP49147511A JPS5839169B2 (ja)	1973-12-21	1974-12-21	イミド基を含む重付加物の製法
FR7525995A FR2275503A1 (fr)	1973-12-21	1975-08-22	Produits de polyaddition de polyimides, de polyphenols et de polyamines, et leur procede de preparation
JP58063527A JPS60364B2 (ja)	1973-12-21	1983-04-11	イミド基を含む重付加物の製法

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH1804773A CH586246A5 (en)	1973-12-21	1973-12-21	Heat stable polymers for paint, electrical and building inds. - and comprising addn. prods. of polyimides, polyphenols and amines

Publications (1)

Publication Number	Publication Date
CH586246A5 true CH586246A5 (en)	1977-03-31

Family

ID=4430028

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1804773A CH586246A5 (en)	1973-12-21	1973-12-21	Heat stable polymers for paint, electrical and building inds. - and comprising addn. prods. of polyimides, polyphenols and amines

Country Status (4)

Country	Link
JP (1)	JPS60364B2 (ja)
BE (1)	BE823720A (ja)
CH (1)	CH586246A5 (ja)
ZA (1)	ZA748135B (ja)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH01136966A (ja) *	1987-11-24	1989-05-30	Kobe Steel Ltd	物理蒸着装置
JP5549329B2 (ja) *	2010-04-02	2014-07-16	住友ベークライト株式会社	回路基板用熱硬化性組成物

1973
- 1973-12-21 CH CH1804773A patent/CH586246A5/de not_active IP Right Cessation
1974
- 1974-12-20 BE BE151824A patent/BE823720A/xx unknown
- 1974-12-20 ZA ZA00748135A patent/ZA748135B/xx unknown
1983
- 1983-04-11 JP JP58063527A patent/JPS60364B2/ja not_active Expired

Also Published As

Publication number	Publication date
JPS60364B2 (ja)	1985-01-08
JPS5941332A (ja)	1984-03-07
ZA748135B (en)	1976-01-28
BE823720A (fr)	1975-06-20

Legal Events

Date	Code	Title	Description
1977-09-15	PL	Patent ceased
2024-10-31	PLX	Patent declared invalid from date of grant onwards

Publication	Publication Date	Title
DE2459925C2 (de)	1989-02-23	Verfahren zur Herstellung von Imidgruppen aufweisenden Polyadditionsprodukten
EP0014816B1 (de)	1983-08-24	Mehrkernige Polyphenole mit Propenylgruppen und härtbare Mischungen auf Basis von Maleinimiden und propenyl substituierten Phenolen
DE2627045C2 (ja)	1990-08-09
DE2754632C2 (de)	1984-04-19	Heißhärtbare Imidharze
DE2754631A1 (de)	1979-06-13	Heisshaertbare imidharze
DE3247058A1 (de)	1983-07-28	Lagerstabile, waermehaertbare, polymerisationskatalysatoren enthaltende mischungen auf polyimidbasis
DE69417701T2 (de)	2000-01-05	Wärmehärtbare Verbindungen, ausgehärtetes Produkt und Verfahren zur Herstellung einer härtbaren Mischung
DE3026384A1 (de)	1981-01-22	Haertbare harzzusammensetzung
DE2354396A1 (de)	1974-05-16	Verarbeitbare polyimide und polyamidimide
CH620938A5 (ja)	1980-12-31
DE2263190A1 (de)	1973-07-05	Loesliche polyimide aus aromatischen dianhydriden und 2,4-diaminodiphenylaminen und 2,4-diaminodiphenylsulfiden
DE69509007T2 (de)	1999-08-26	Konzentrierte Prepolymerzusammensetzung zur Herstellung von Polyimidformkörpern
DE2002368C3 (de)	1979-11-08	Hitzehärtbare Novolakharzmischung mit verbesserter thermischer Stabilität
DE2459961A1 (de)	1975-07-03	Verfahren zur herstellung von imidgruppen aufweisenden polyadditionsprodukten
DE2234166A1 (de)	1973-01-25	Polyimide und verfahren zu deren herstellung
DE2529092A1 (de)	1976-01-22	Lagerstabile, heisshaertbare mischungen
DE2459938A1 (de)	1975-07-03	Verfahren zur herstellung von imidgruppen aufweisenden polyadditionsprodukten
CH586246A5 (en)	1977-03-31	Heat stable polymers for paint, electrical and building inds. - and comprising addn. prods. of polyimides, polyphenols and amines
EP0300329B1 (de)	1993-03-17	Bismaleinimid-Harze
DE2544900A1 (de)	1976-04-29	Haertbare mischungen auf basis von polyimiden ungesaettigter dicarbonsaeuren
DE3827120A1 (de)	1990-02-15	Hitzehaertbare bismaleinimid-copolymere sowie 2,6-disubstituierte pyridin-verbindungen als comonomere
DE2038275C3 (de)	1981-09-17	Polyimide aus 2,6-Diamino-s-triazinen und Dianhydriden
DE2461024A1 (de)	1975-07-10	Kettenverlaengerungsreaktionen fuer hochtemperaturpolymere durch alpha, beta-ungesaettigte schiff'sche basen
DE2613339A1 (de)	1976-11-04	Polymerisierbare produkte
CH587295A5 (en)	1977-04-29	Heat stable polymers for paint, electrical and building inds. - and comprising addn. prods. of polyimides, polyphenols and amines