DE1545187B2 - Verfahren zur herstellung einer mischung aus epoxydverbindungen und methylendianilin als haertungsmittel - Google Patents
Verfahren zur herstellung einer mischung aus epoxydverbindungen und methylendianilin als haertungsmittelInfo
- Publication number
- DE1545187B2 DE1545187B2 DE1963W0034046 DEW0034046A DE1545187B2 DE 1545187 B2 DE1545187 B2 DE 1545187B2 DE 1963W0034046 DE1963W0034046 DE 1963W0034046 DE W0034046 A DEW0034046 A DE W0034046A DE 1545187 B2 DE1545187 B2 DE 1545187B2
- Authority
- DE
- Germany
- Prior art keywords
- mixture
- methylenedianiline
- epoxy
- epoxy compounds
- curing agent
- 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.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims description 38
- 239000004593 Epoxy Substances 0.000 title claims description 17
- 150000001875 compounds Chemical class 0.000 title claims description 9
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 title claims description 8
- 239000003795 chemical substances by application Substances 0.000 title description 9
- 238000004519 manufacturing process Methods 0.000 title description 3
- 239000007787 solid Substances 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 8
- 239000000654 additive Substances 0.000 claims description 6
- 238000004898 kneading Methods 0.000 claims description 4
- 239000004848 polyfunctional curative Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 11
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 10
- 239000000843 powder Substances 0.000 description 10
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 229920000647 polyepoxide Polymers 0.000 description 7
- 239000008187 granular material Substances 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 229920003986 novolac Polymers 0.000 description 6
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 6
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 5
- 238000001723 curing Methods 0.000 description 5
- 239000000945 filler Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 4
- 239000003822 epoxy resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 238000005204 segregation Methods 0.000 description 4
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 229930003836 cresol Natural products 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 229910000831 Steel Inorganic materials 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 2
- 239000008116 calcium stearate Substances 0.000 description 2
- 235000013539 calcium stearate Nutrition 0.000 description 2
- XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical group CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 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 2
- 230000001771 impaired effect Effects 0.000 description 2
- 239000011256 inorganic filler Substances 0.000 description 2
- 229910003475 inorganic filler Inorganic materials 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 235000013824 polyphenols Nutrition 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 238000013517 stratification Methods 0.000 description 2
- PFTAWBLQPZVEMU-DZGCQCFKSA-N (+)-catechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-DZGCQCFKSA-N 0.000 description 1
- MCMNRKCIXSYSNV-UHFFFAOYSA-N ZrO2 Inorganic materials O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229940037003 alum Drugs 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000000181 anti-adherent effect Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000010425 asbestos Substances 0.000 description 1
- 239000010428 baryte Substances 0.000 description 1
- 229910052601 baryte Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- ADRVNXBAWSRFAJ-UHFFFAOYSA-N catechin Natural products OC1Cc2cc(O)cc(O)c2OC1c3ccc(O)c(O)c3 ADRVNXBAWSRFAJ-UHFFFAOYSA-N 0.000 description 1
- 235000005487 catechin Nutrition 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229950001002 cianidanol Drugs 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 238000005056 compaction Methods 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 238000013007 heat curing Methods 0.000 description 1
- 230000017525 heat dissipation Effects 0.000 description 1
- 230000020169 heat generation Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- RTWNYYOXLSILQN-UHFFFAOYSA-N methanediamine Chemical compound NCN RTWNYYOXLSILQN-UHFFFAOYSA-N 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- -1 powdered alum Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 239000004408 titanium dioxide 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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Epoxy Resins (AREA)
- Processing And Handling Of Plastics And Other Materials For Molding In General (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US178571A US3390123A (en) | 1962-03-09 | 1962-03-09 | Molding compositions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1545187A1 DE1545187A1 (de) | 1969-11-27 |
| DE1545187B2 true DE1545187B2 (de) | 1976-11-11 |
Family
ID=22653074
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1963W0034046 Granted DE1545187B2 (de) | 1962-03-09 | 1963-03-07 | Verfahren zur herstellung einer mischung aus epoxydverbindungen und methylendianilin als haertungsmittel |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3390123A (en, 2012) |
| BE (1) | BE629380A (en, 2012) |
| CH (1) | CH445117A (en, 2012) |
| DE (1) | DE1545187B2 (en, 2012) |
| DK (1) | DK107060C (en, 2012) |
| FI (1) | FI41873C (en, 2012) |
| GB (1) | GB1033514A (en, 2012) |
| NL (2) | NL138957B (en, 2012) |
| NO (1) | NO117394B (en, 2012) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4146525A (en) * | 1977-06-20 | 1979-03-27 | Minnesota Mining And Manufacturing Company | High strength ceramic-polymer composites |
| DE3026455A1 (de) * | 1980-07-12 | 1982-02-11 | Chemische Werke Hüls AG, 4370 Marl | Verfahren zur herstellung von haertern fuer epoxidharze aus monosalzen von aromatischen polycarbonsaeuren |
| DE3424700A1 (de) * | 1984-07-05 | 1986-02-06 | Basf Ag, 6700 Ludwigshafen | Faserverbundwerkstoffe auf basis von epoxidharzen |
| GB8503882D0 (en) * | 1985-02-15 | 1985-03-20 | Raychem Ltd | Heat curable composition |
| JP2501154B2 (ja) * | 1990-11-26 | 1996-05-29 | 三井東圧化学株式会社 | テトラキスキシレノ―ルエタンの製造方法 |
| US6165558A (en) * | 1996-02-02 | 2000-12-26 | Vantico, Inc. | Storage-stable moulding powder based on epoxy resins |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2899407A (en) * | 1959-08-11 | Xcuming o of epoxy resins | ||
| BE474687A (en, 2012) * | 1945-07-13 | 1900-01-01 | ||
| US2773048A (en) * | 1952-08-25 | 1956-12-04 | Honeywell Regulator Co | Epoxy resin composition containing para, para' diamino diphenylmethane |
| US2934520A (en) * | 1954-10-04 | 1960-04-26 | Aries Lab Inc | Epoxy resin compositions |
| US2806016A (en) * | 1954-11-01 | 1957-09-10 | Shell Dev | Polyglycidyl ethers of tetraphenols |
| NL193475A (en, 2012) * | 1954-12-23 | |||
| US2866768A (en) * | 1955-03-18 | 1958-12-30 | Honeywell Regulator Co | Epoxy molding composition and method of molding with same |
| NL218575A (en, 2012) * | 1956-07-03 | |||
| BE559783A (en, 2012) * | 1956-08-03 | 1900-01-01 | ||
| US3025263A (en) * | 1957-07-31 | 1962-03-13 | Jr Henry L Lee | Epoxy carboxylic acid dianhydride compositions |
| US2965930A (en) * | 1957-08-21 | 1960-12-27 | Union Carbide Corp | Process for preparing polyepoxide solder |
| US3159595A (en) * | 1960-08-11 | 1964-12-01 | Shell Oil Co | Blending crystalline 2, 2-bis(2, 3-epoxypropoxyphenyl) propane with curing agent |
-
0
- NL NL289911D patent/NL289911A/xx unknown
- BE BE629380D patent/BE629380A/xx unknown
-
1962
- 1962-03-09 US US178571A patent/US3390123A/en not_active Expired - Lifetime
-
1963
- 1963-02-26 GB GB7651/63A patent/GB1033514A/en not_active Expired
- 1963-03-07 DE DE1963W0034046 patent/DE1545187B2/de active Granted
- 1963-03-07 NL NL63289911A patent/NL138957B/xx not_active IP Right Cessation
- 1963-03-08 CH CH298763A patent/CH445117A/de unknown
- 1963-03-08 NO NO147829A patent/NO117394B/no unknown
- 1963-03-08 FI FI630452A patent/FI41873C/fi active
- 1963-03-09 DK DK110463AA patent/DK107060C/da active
Also Published As
| Publication number | Publication date |
|---|---|
| CH445117A (de) | 1967-10-15 |
| FI41873B (en, 2012) | 1969-12-01 |
| GB1033514A (en) | 1966-06-22 |
| BE629380A (en, 2012) | |
| NL289911A (en, 2012) | |
| NO117394B (en, 2012) | 1969-08-04 |
| FI41873C (fi) | 1970-03-10 |
| US3390123A (en) | 1968-06-25 |
| NL138957B (nl) | 1973-05-15 |
| DE1545187A1 (de) | 1969-11-27 |
| DK107060C (da) | 1967-04-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| SH | Request for examination between 03.10.1968 and 22.04.1971 | ||
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 |