CH617944A5 - - Google Patents

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Info

Publication number: CH617944A5
Authority: CH; Switzerland
Prior art keywords: reaction; epoxy; phenol; epoxy resin; radical
Prior art date: 1974-06-21

Application number

CH809575A

Other languages

German (de)

English (en)

Inventor

George Anthony Doorakian

Lawrence Gilbert Duquette

Original Assignee

Dow Chemical Co

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.)

1974-06-21

Filing date

1975-06-20

Publication date

1980-06-30

1975-06-20 Application filed by Dow Chemical Co filed Critical Dow Chemical Co

1980-06-30 Publication of CH617944A5 publication Critical patent/CH617944A5/de

Links

-1 hydrocarbon radicals Chemical class 0.000 claims description 34
239000003054 catalyst Substances 0.000 claims description 30
238000006243 chemical reaction Methods 0.000 claims description 30
229920000647 polyepoxide Polymers 0.000 claims description 26
239000003822 epoxy resin Substances 0.000 claims description 25
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 15
150000001875 compounds Chemical class 0.000 claims description 14
238000000034 method Methods 0.000 claims description 14
239000007858 starting material Substances 0.000 claims description 14
239000004593 Epoxy Substances 0.000 claims description 13
239000000203 mixture Substances 0.000 claims description 12
229930195733 hydrocarbon Natural products 0.000 claims description 11
239000004215 Carbon black (E152) Substances 0.000 claims description 10
150000001450 anions Chemical class 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 8
125000003700 epoxy group Chemical group 0.000 claims description 8
150000004714 phosphonium salts Chemical class 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 7
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 7
238000004519 manufacturing process Methods 0.000 claims description 5
SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 4
150000002430 hydrocarbons Chemical class 0.000 claims description 3
230000003472 neutralizing effect Effects 0.000 claims description 3
125000001424 substituent group Chemical group 0.000 claims description 3
229920013730 reactive polymer Polymers 0.000 claims 1
LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 15
150000002989 phenols Chemical class 0.000 description 15
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 description 11
150000002118 epoxides Chemical class 0.000 description 10
239000000047 product Substances 0.000 description 10
125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
239000007795 chemical reaction product Substances 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
125000000217 alkyl group Chemical group 0.000 description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
125000002947 alkylene group Chemical group 0.000 description 4
238000000576 coating method Methods 0.000 description 4
238000002474 experimental method Methods 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
125000001931 aliphatic group Chemical group 0.000 description 3
150000008064 anhydrides Chemical class 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 3
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
229920005989 resin Polymers 0.000 description 3
239000011347 resin Substances 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 2
239000012790 adhesive layer Substances 0.000 description 2
WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 2
KJCVRFUGPWSIIH-UHFFFAOYSA-N alpha-naphthol Natural products C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
150000001735 carboxylic acids Chemical class 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
FOCAUTSVDIKZOP-UHFFFAOYSA-M chloroacetate Chemical compound [O-]C(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-M 0.000 description 2
229940089960 chloroacetate Drugs 0.000 description 2
229920006037 cross link polymer Polymers 0.000 description 2
MIHINWMALJZIBX-UHFFFAOYSA-N cyclohexa-2,4-dien-1-ol Chemical class OC1CC=CC=C1 MIHINWMALJZIBX-UHFFFAOYSA-N 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
239000012530 fluid Substances 0.000 description 2
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
238000002156 mixing Methods 0.000 description 2
230000000269 nucleophilic effect Effects 0.000 description 2
150000002894 organic compounds Chemical class 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 2
229920000642 polymer Polymers 0.000 description 2
GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000011593 sulfur Chemical group 0.000 description 2
229910052717 sulfur Inorganic materials 0.000 description 2
RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 1
229940005561 1,4-benzoquinone Drugs 0.000 description 1
ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 1
125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 1
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
HORNXRXVQWOLPJ-UHFFFAOYSA-N 3-chlorophenol Chemical compound OC1=CC=CC(Cl)=C1 HORNXRXVQWOLPJ-UHFFFAOYSA-N 0.000 description 1
QWGLNWHWBCINBS-UHFFFAOYSA-N 3-nonylphenol Chemical class CCCCCCCCCC1=CC=CC(O)=C1 QWGLNWHWBCINBS-UHFFFAOYSA-N 0.000 description 1
OSDLLIBGSJNGJE-UHFFFAOYSA-N 4-chloro-3,5-dimethylphenol Chemical class CC1=CC(O)=CC(C)=C1Cl OSDLLIBGSJNGJE-UHFFFAOYSA-N 0.000 description 1
WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
IGFHQQFPSIBGKE-UHFFFAOYSA-N 4-nonylphenol Chemical class CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical class CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 1
HOSGXJWQVBHGLT-UHFFFAOYSA-N 6-hydroxy-3,4-dihydro-1h-quinolin-2-one Chemical group N1C(=O)CCC2=CC(O)=CC=C21 HOSGXJWQVBHGLT-UHFFFAOYSA-N 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
239000007848 Bronsted acid Substances 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Chemical group CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
PQGAHNJECSVDEI-UHFFFAOYSA-N [CH2]CCCCC Chemical compound [CH2]CCCCC PQGAHNJECSVDEI-UHFFFAOYSA-N 0.000 description 1
229940048053 acrylate Drugs 0.000 description 1
239000000654 additive Substances 0.000 description 1
125000001118 alkylidene group Chemical group 0.000 description 1
238000005349 anion exchange Methods 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
229940073608 benzyl chloride Drugs 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
229950011260 betanaphthol Drugs 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000006757 chemical reactions by type Methods 0.000 description 1
XTHPWXDJESJLNJ-UHFFFAOYSA-M chlorosulfate Chemical compound [O-]S(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-M 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
239000008199 coating composition Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
239000013256 coordination polymer Substances 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
LRMHFDNWKCSEQU-UHFFFAOYSA-N ethoxyethane;phenol Chemical group CCOCC.OC1=CC=CC=C1 LRMHFDNWKCSEQU-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000000835 fiber Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical group 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004356 hydroxy functional group Chemical group O* 0.000 description 1
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000000178 monomer Substances 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000002736 nonionic surfactant Substances 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000008379 phenol ethers Chemical class 0.000 description 1
229960005323 phenoxyethanol Drugs 0.000 description 1
229910000073 phosphorus hydride Inorganic materials 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
239000012048 reactive intermediate Substances 0.000 description 1
238000007142 ring opening reaction Methods 0.000 description 1
125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000003860 storage Methods 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
229940066528 trichloroacetate Drugs 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
239000002023 wood Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/54—Quaternary phosphonium compounds
- C07F9/5442—Aromatic phosphonium compounds (P-C aromatic linkage)
- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/14—Polycondensates modified by chemical after-treatment
- C08G59/1433—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds
- C08G59/1438—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds containing oxygen
- C08G59/1455—Monocarboxylic acids, anhydrides, halides, or low-molecular-weight esters thereof
- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
- C08G59/688—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used containing phosphorus

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
General Health & Medical Sciences (AREA)
Biochemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Molecular Biology (AREA)
Emergency Medicine (AREA)
General Chemical & Material Sciences (AREA)
Epoxy Resins (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Catalysts (AREA)
Paints Or Removers (AREA)

CH809575A 1974-06-21 1975-06-20 CH617944A5 (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US48159974A	1974-06-21	1974-06-21

Publications (1)

Publication Number	Publication Date
CH617944A5 true CH617944A5 (fr)	1980-06-30

Family

ID=23912608

Family Applications (4)

Application Number	Title	Priority Date
CH809675A CH618198A5 (fr)	1974-06-21	1975-06-20
CH810075A CH618449A5 (fr)	1974-06-21	1975-06-20
CH809575A CH617944A5 (fr)	1974-06-21	1975-06-20
CH1002179A CH621564A5 (fr)	1974-06-21	1979-11-08

Family Applications Before (2)

Application Number	Title	Priority Date	Filing Date
CH809675A CH618198A5 (fr)	1974-06-21	1975-06-20
CH810075A CH618449A5 (fr)	1974-06-21	1975-06-20

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
CH1002179A CH621564A5 (fr)	1974-06-21	1979-11-08

Country Status (9)

Country	Link
US (1)	US4132706A (fr)
JP (3)	JPS5113894A (fr)
BR (3)	BR7503896A (fr)
CA (3)	CA1051031A (fr)
CH (4)	CH618198A5 (fr)
DE (5)	DE2527002C2 (fr)
ES (2)	ES438785A1 (fr)
GB (3)	GB1492868A (fr)
ZA (3)	ZA753393B (fr)

Families Citing this family (61)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5333599Y2 (fr) *	1974-01-21	1978-08-18
US4302574A (en) *	1979-05-23	1981-11-24	The Dow Chemical Company	Phosphonium phenoxide catalysts for promoting reacting of epoxides with phenols and/or carboxylic acids
US4410596A (en) *	1980-12-04	1983-10-18	The Dow Chemical Co.	Process for preparing epoxy resins having improved physical properties when cured
USRE32951E (en) *	1980-12-04	1989-06-13	The Dow Chemical Company	Process for preparing epoxy resins having improved physical properties when cured using quaternary phosphonium catalysts
US4370465A (en) *	1980-12-04	1983-01-25	The Dow Chemical Co.	Epoxy resins having improved physical properties when cured
US4352918A (en) *	1980-12-04	1982-10-05	The Dow Chemical Company	Process for preparing epoxy resins having improved physical properties when cured using quaternary phosphonium catalysts
DE3151540A1 (de) *	1980-12-29	1982-08-19	Ciba-Geigy GmbH, 7867 Wehr	"verwendung von transparenten anhydridhaertbaren epoxidgiessharzen"
US4389520A (en) *	1982-04-05	1983-06-21	Ciba-Geigy Corporation	Advancement catalysts for epoxy resins
WO1984000171A1 (fr) *	1982-06-23	1984-01-19	Dow Chemical Co	Procede de preparation de resines epoxydes avancees utilisant un catalyseur au trifluoroacetate de phosphonium
US4496709A (en) *	1982-06-23	1985-01-29	The Dow Chemical Company	Process for preparing epoxy resins employing a phosphonium trifluoroacetate catalyst
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1975
- 1975-05-22 CA CA227,512A patent/CA1051031A/fr not_active Expired
- 1975-05-22 CA CA227,513A patent/CA1059692A/fr not_active Expired
- 1975-05-22 CA CA227,514A patent/CA1041696A/fr not_active Expired
- 1975-05-26 ZA ZA00753393A patent/ZA753393B/xx unknown
- 1975-05-26 ZA ZA00753392A patent/ZA753392B/xx unknown
- 1975-05-26 ZA ZA00753391A patent/ZA753391B/xx unknown
- 1975-06-18 DE DE2527002A patent/DE2527002C2/de not_active Expired
- 1975-06-18 DE DE2559587A patent/DE2559587C3/de not_active Expired
- 1975-06-18 GB GB26032/75A patent/GB1492868A/en not_active Expired
- 1975-06-18 DE DE2559611A patent/DE2559611C3/de not_active Expired
- 1975-06-18 DE DE2527116A patent/DE2527116C3/de not_active Expired
- 1975-06-18 DE DE2527117A patent/DE2527117C3/de not_active Expired
- 1975-06-19 GB GB26193/75A patent/GB1492869A/en not_active Expired
- 1975-06-20 BR BR5007/75D patent/BR7503896A/pt unknown
- 1975-06-20 JP JP50074587A patent/JPS5113894A/ja active Pending
- 1975-06-20 BR BR5008/75D patent/BR7503897A/pt unknown
- 1975-06-20 JP JP50074588A patent/JPS5113895A/ja active Pending
- 1975-06-20 CH CH809675A patent/CH618198A5/de not_active IP Right Cessation
- 1975-06-20 CH CH810075A patent/CH618449A5/de not_active IP Right Cessation
- 1975-06-20 GB GB2634875A patent/GB1464240A/en not_active Expired
- 1975-06-20 CH CH809575A patent/CH617944A5/de not_active IP Right Cessation
- 1975-06-20 BR BR5009/75D patent/BR7503898A/pt unknown
- 1975-06-20 JP JP50074586A patent/JPS5119748A/ja active Pending
- 1975-06-21 ES ES438785A patent/ES438785A1/es not_active Expired
- 1975-06-21 ES ES438786A patent/ES438786A1/es not_active Expired
1976
- 1976-04-05 US US05/674,019 patent/US4132706A/en not_active Expired - Lifetime
1979
- 1979-11-08 CH CH1002179A patent/CH621564A5/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
JPS5119748A (en)	1976-02-17
DE2527117A1 (de)	1976-01-02
AU8161775A (en)	1976-12-02
GB1492868A (en)	1977-11-23
DE2559611C3 (de)	1982-04-08
BR7503896A (pt)	1976-07-06
DE2527117C3 (de)	1978-09-28
BR7503897A (pt)	1976-07-06
CA1051031A (fr)	1979-03-20
GB1492869A (en)	1977-11-23
DE2559611B2 (de)	1981-06-25
BR7503898A (pt)	1976-07-06
CH618449A5 (fr)	1980-07-31
ZA753391B (en)	1976-04-28
DE2527116B2 (de)	1979-04-05
AU8167475A (en)	1976-12-02
CA1059692A (fr)	1979-07-31
DE2527117B2 (de)	1977-12-01
DE2527116C3 (de)	1979-11-29
DE2559587B2 (de)	1980-04-24
GB1464240A (en)	1977-02-09
DE2527116A1 (de)	1976-01-02
ES438785A1 (es)	1977-06-01
ZA753393B (en)	1976-06-30
CH621564A5 (fr)	1981-02-13
US4132706A (en)	1979-01-02
DE2559587C3 (de)	1981-01-29
DE2527002C2 (de)	1984-08-16
AU8167275A (en)	1976-12-02
CA1041696A (fr)	1978-10-31
DE2527002A1 (de)	1976-01-08
ES438786A1 (es)	1977-03-16
DE2559587A1 (de)	1977-05-05
JPS5113894A (fr)	1976-02-03
CH618198A5 (fr)	1980-07-15
JPS5113895A (fr)	1976-02-03
ZA753392B (en)	1976-04-28
DE2559611A1 (de)	1977-04-28

Legal Events

Date	Code	Title	Description
1995-02-28	PL	Patent ceased

Publication	Publication Date	Title
CH617944A5 (fr)	1980-06-30
DE2459447C2 (de)	1984-05-30	Epoxidgruppenhaltige Addukte auf Basis von Polyesterdicarbonsäuren
DE1420797B2 (de)	1973-05-03	Verfahren zur ueberfuehrung von polyglycidylpolyaethern mehrwertiger phenole in hochmolekulare vernetzte produkte
DE1214882B (de)	1966-04-21	Verfahren zur Herstellung von haertbaren, hochmolekularen, Epoxydgruppen enthaltenden Verbindungen
DE1812972A1 (de)	1969-07-10	Verfahren zur Herstellung von Phenylhydroxyaethern
DE2809768B2 (de)	1981-02-12	Verfahren zur Herstellung von Epoxyharzen
CH658457A5 (de)	1986-11-14	Difunktionelles epoxid.
DE1495446C3 (de)	1979-11-22	Verfahren zur Herstellung von selbstverlöschenden vernetzten Epoxydpolyaddukten
DE2448168A1 (de)	1975-04-30	Haertbare epoxydharz-zusammensetzung und verfahren zu ihrer herstellung
DE1060138B (de)	1959-06-25	Verfahren zur Herstellung von modifizierten gehaerteten Epoxyharzen
EP0135477B1 (fr)	1988-01-07	Ethers polyglycidyliques
DE2206218A1 (de)	1973-08-16	Verfahren zur herstellung von epoxidharzen
DE2147899A1 (de)	1972-07-06	Neue Polyglycidylverbindungen, Verfahren zu ihrer Herstellung und Anwendung
DE2262157C2 (de)	1982-02-18	Niedrigviskose, halogenhaltige selbstverlöschende Epoxidharze, Verfahren zu ihrer Herstellung und ihre Verwendung
DE1301135B (de)	1969-08-14	Verfahren zur Herstellung von Formkoerpern
DE2403407C3 (de)	1980-02-21	Verfahren zur Umsetzung von Epoxyverbindungen mit Phenolen
DE1050065B (de)	1959-02-05	Verfahren zur Herstellung von härtbaren, siliziumhalitigen Kunststoffen
DE1570750A1 (de)	1972-03-30	Verfahren zur Herstellung von metallhaltigen gehaerteten Epoxyharzen
DE2006217A1 (de)	1970-11-26	Gehärtete aromatische Harze
DE1816096B2 (de)	1974-11-14	Langkettige, aromatische Säurereste enthaltende Polyglycidylester, Verfahren zu ihrer Herstellung und Anwendung
DE1520815C (de)	1972-09-28	Epoxydverbindungen enthaltende Mischungen zur Herstellung flammwidriger hitzegehärteter Polyaddukte
DE1520815B2 (de)	1972-02-24	Epoxydverbindungen enthaltende mischungen zur herstellung flammwidriger hitzegehaerteter polyaddukte
DE1493640C (de)	1973-08-02	Verfahren zur Herstellung von Glycidyläthern mehrwertiger Phenole
DE1816933C (de)	1972-04-27	Verfahren zur Herstellung von Epoxy Polyaddukten
DE2609475A1 (de)	1977-09-15	Verfahren zum umsetzen von epoxiden und zusammensetzung auf basis von epoxyharzen