DE1040235B - Verfahren zum Haerten von harzartigen Polyepoxyverbindungen durch Phenol-aldehydkondensationsprodukte - Google Patents
Verfahren zum Haerten von harzartigen Polyepoxyverbindungen durch Phenol-aldehydkondensationsprodukteInfo
- Publication number
- DE1040235B DE1040235B DEN12878A DEN0012878A DE1040235B DE 1040235 B DE1040235 B DE 1040235B DE N12878 A DEN12878 A DE N12878A DE N0012878 A DEN0012878 A DE N0012878A DE 1040235 B DE1040235 B DE 1040235B
- Authority
- DE
- Germany
- Prior art keywords
- phenol
- curing
- condensation products
- aldehyde condensation
- resorcinol
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 10
- 239000007859 condensation product Substances 0.000 title claims description 7
- 150000001875 compounds Chemical class 0.000 title claims description 4
- 229920000647 polyepoxide Polymers 0.000 claims description 19
- 229920005989 resin Polymers 0.000 claims description 14
- 239000011347 resin Substances 0.000 claims description 14
- DGXAGETVRDOQFP-UHFFFAOYSA-N 2,6-dihydroxybenzaldehyde Chemical compound OC1=CC=CC(O)=C1C=O DGXAGETVRDOQFP-UHFFFAOYSA-N 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 150000002989 phenols Chemical class 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 3
- -1 phenol aldehyde Chemical class 0.000 claims description 3
- 238000012986 modification Methods 0.000 claims 1
- 230000004048 modification Effects 0.000 claims 1
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 17
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 239000003822 epoxy resin Substances 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 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 3
- 238000005266 casting Methods 0.000 description 3
- 125000003700 epoxy group Chemical group 0.000 description 3
- 229960004279 formaldehyde Drugs 0.000 description 3
- 235000019256 formaldehyde Nutrition 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 239000004848 polyfunctional curative Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- IFVTZJHWGZSXFD-UHFFFAOYSA-N biphenylene Chemical group C1=CC=C2C3=CC=CC=C3C2=C1 IFVTZJHWGZSXFD-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229920003986 novolac Polymers 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- 229920001568 phenolic resin Polymers 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 229930185605 Bisphenol Natural products 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
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000003944 halohydrins Chemical class 0.000 description 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 1
- 239000000463 material Substances 0.000 description 1
- RCHKEJKUUXXBSM-UHFFFAOYSA-N n-benzyl-2-(3-formylindol-1-yl)acetamide Chemical compound C12=CC=CC=C2C(C=O)=CN1CC(=O)NCC1=CC=CC=C1 RCHKEJKUUXXBSM-UHFFFAOYSA-N 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 239000003208 petroleum 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
- 239000004014 plasticizer Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000007096 poisonous effect Effects 0.000 description 1
- 238000011417 postcuring Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229920003987 resole Polymers 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 231100001068 severe skin irritation Toxicity 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL359883X | 1955-10-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1040235B true DE1040235B (de) | 1958-10-02 |
Family
ID=19785361
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEN12878A Pending DE1040235B (de) | 1955-10-28 | 1956-10-26 | Verfahren zum Haerten von harzartigen Polyepoxyverbindungen durch Phenol-aldehydkondensationsprodukte |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE552113A (enrdf_load_stackoverflow) |
| CH (1) | CH359883A (enrdf_load_stackoverflow) |
| DE (1) | DE1040235B (enrdf_load_stackoverflow) |
| FR (1) | FR1164264A (enrdf_load_stackoverflow) |
| GB (1) | GB798174A (enrdf_load_stackoverflow) |
| NL (2) | NL88517C (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1138542B (de) * | 1959-11-23 | 1962-10-25 | Reichhold Chemie Ag | Formmassen, die Epoxydverbindungen und Novolake enthalten |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1201051B (de) * | 1960-07-01 | 1965-09-16 | Feldmuehle Ag | Verfahren zur Herstellung von poroesen Schleif-koerpern aus Phenolformaldehydharzen |
| DE1236794B (de) * | 1963-11-13 | 1967-03-16 | Minnesota Mining & Mfg | Verfahren zur Herstellung von Formkoerpern auf der Basis von Polyaddukten |
| US4368299A (en) * | 1980-08-07 | 1983-01-11 | Sumitomo Chemical Company, Limited | Epoxy resin compositions |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2458796A (en) * | 1946-08-08 | 1949-01-11 | Ciba Ltd | Phenol oxide resin lacquers and their manufacture |
| US2521911A (en) * | 1946-03-08 | 1950-09-12 | Devoe & Raynolds Co | Phenol-aldehyde and epoxide resin compositions |
-
0
- NL NL201584D patent/NL201584A/xx unknown
- NL NL88517D patent/NL88517C/xx active
- BE BE552113D patent/BE552113A/xx unknown
-
1956
- 1956-10-17 FR FR1164264D patent/FR1164264A/fr not_active Expired
- 1956-10-25 CH CH359883D patent/CH359883A/de unknown
- 1956-10-26 GB GB32671/56A patent/GB798174A/en not_active Expired
- 1956-10-26 DE DEN12878A patent/DE1040235B/de active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2521911A (en) * | 1946-03-08 | 1950-09-12 | Devoe & Raynolds Co | Phenol-aldehyde and epoxide resin compositions |
| US2458796A (en) * | 1946-08-08 | 1949-01-11 | Ciba Ltd | Phenol oxide resin lacquers and their manufacture |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1138542B (de) * | 1959-11-23 | 1962-10-25 | Reichhold Chemie Ag | Formmassen, die Epoxydverbindungen und Novolake enthalten |
Also Published As
| Publication number | Publication date |
|---|---|
| GB798174A (en) | 1958-07-16 |
| NL88517C (enrdf_load_stackoverflow) | |
| BE552113A (enrdf_load_stackoverflow) | |
| NL201584A (enrdf_load_stackoverflow) | |
| CH359883A (de) | 1962-01-31 |
| FR1164264A (fr) | 1958-10-07 |
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