DE1966942C3 - Verfahren zur Herstellung von Glasfasergegenstanden - Google Patents
Verfahren zur Herstellung von GlasfasergegenstandenInfo
- Publication number
- DE1966942C3 DE1966942C3 DE1966942A DE1966942A DE1966942C3 DE 1966942 C3 DE1966942 C3 DE 1966942C3 DE 1966942 A DE1966942 A DE 1966942A DE 1966942 A DE1966942 A DE 1966942A DE 1966942 C3 DE1966942 C3 DE 1966942C3
- Authority
- DE
- Germany
- Prior art keywords
- resin
- laminate
- acid
- catalyst
- glass
- 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
- 238000000034 method Methods 0.000 title claims description 49
- 230000008569 process Effects 0.000 title claims description 16
- 239000011152 fibreglass Substances 0.000 title description 10
- 229920005989 resin Polymers 0.000 claims description 121
- 239000011347 resin Substances 0.000 claims description 121
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 claims description 72
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Substances O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 47
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 44
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 claims description 42
- 239000003054 catalyst Substances 0.000 claims description 33
- 239000011230 binding agent Substances 0.000 claims description 30
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 22
- 239000003365 glass fiber Substances 0.000 claims description 19
- 238000004519 manufacturing process Methods 0.000 claims description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 11
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical compound [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 claims description 11
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 10
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 claims description 8
- 239000003377 acid catalyst Substances 0.000 claims description 5
- 239000000853 adhesive Substances 0.000 claims description 4
- 230000001070 adhesive effect Effects 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 230000003472 neutralizing effect Effects 0.000 claims description 3
- 239000000835 fiber Substances 0.000 claims 1
- 239000011521 glass Substances 0.000 description 39
- 238000001723 curing Methods 0.000 description 23
- 238000002474 experimental method Methods 0.000 description 21
- 239000004744 fabric Substances 0.000 description 18
- 238000012360 testing method Methods 0.000 description 16
- 239000000203 mixture Substances 0.000 description 15
- 238000009835 boiling Methods 0.000 description 12
- 239000000463 material Substances 0.000 description 12
- 229920002799 BoPET Polymers 0.000 description 11
- 239000005041 Mylar™ Substances 0.000 description 11
- 239000000499 gel Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 9
- 229910000077 silane Inorganic materials 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000000523 sample Substances 0.000 description 8
- 238000001816 cooling Methods 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- 229920000728 polyester Polymers 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000007921 spray Substances 0.000 description 6
- 238000011282 treatment Methods 0.000 description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 238000013459 approach Methods 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 150000004756 silanes Chemical class 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 238000005187 foaming Methods 0.000 description 3
- 238000007654 immersion Methods 0.000 description 3
- 238000010030 laminating Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 238000011417 postcuring Methods 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000005096 rolling process Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 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 description 2
- 239000002131 composite material Substances 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000003822 epoxy resin Substances 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
- 238000005259 measurement Methods 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000000644 propagated effect Effects 0.000 description 2
- 239000002990 reinforced plastic Substances 0.000 description 2
- 239000011342 resin composition Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000013007 heat curing Methods 0.000 description 1
- 230000020169 heat generation Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000009533 lab test Methods 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000009864 tensile test Methods 0.000 description 1
- 239000013026 undiluted sample Substances 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000004804 winding Methods 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
- C08G16/00—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00
- C08G16/02—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00 of aldehydes
- C08G16/025—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00 of aldehydes with heterocyclic organic compounds
- C08G16/0256—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00 of aldehydes with heterocyclic organic compounds containing oxygen in the ring
- C08G16/0262—Furfuryl alcohol
-
- C—CHEMISTRY; METALLURGY
- C03—GLASS; MINERAL OR SLAG WOOL
- C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
- C03C25/00—Surface treatment of fibres or filaments made from glass, minerals or slags
- C03C25/10—Coating
- C03C25/24—Coatings containing organic materials
- C03C25/26—Macromolecular compounds or prepolymers
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Geochemistry & Mineralogy (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- General Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Reinforced Plastic Materials (AREA)
- Laminated Bodies (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US73328268A | 1968-05-31 | 1968-05-31 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1966942A1 DE1966942A1 (de) | 1975-12-18 |
| DE1966942B2 DE1966942B2 (de) | 1978-02-16 |
| DE1966942C3 true DE1966942C3 (de) | 1978-09-21 |
Family
ID=24946962
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1966942A Expired DE1966942C3 (de) | 1968-05-31 | 1969-05-30 | Verfahren zur Herstellung von Glasfasergegenstanden |
| DE19691927776 Pending DE1927776A1 (de) | 1968-05-31 | 1969-05-30 | Saeurehaertbare Bindemittelmasse |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19691927776 Pending DE1927776A1 (de) | 1968-05-31 | 1969-05-30 | Saeurehaertbare Bindemittelmasse |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US3594345A (enExample) |
| DE (2) | DE1966942C3 (enExample) |
| GB (1) | GB1226065A (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1632595B1 (de) * | 1967-12-14 | 1971-07-01 | Augusta Zuender Feuerzeugfabri | Piezoelektrisches feuerzeug, insbesondere taschenfeuerzeug |
| US3850727A (en) * | 1973-04-16 | 1974-11-26 | Quaker Oats Co | Method of fabrication of furan resin bonded, fiber reinforced articles |
| US3927139A (en) * | 1973-11-26 | 1975-12-16 | Quaker Oats Co | Method of fabrication of furan resin bonded fiber reinforced articles by spray-up technique |
| GB1568519A (en) * | 1976-12-21 | 1980-05-29 | Foseco Technik Ag | Resin-forming furfuryl alcohol compositions and their use in the production of foundry moulds and cores |
| US4178429A (en) * | 1978-11-17 | 1979-12-11 | Scheffer Karl D | Catalyst for curing resins |
| EP0365531A1 (de) * | 1988-04-18 | 1990-05-02 | MüANYAGIPARI KUTATO INTEZET | Kunststoff-formkörper zum sieben heisser flüssigkeiten, insbesondere geschmolzener metalle, und verfahren zu ihrer herstellung |
| US6077883A (en) * | 1992-05-19 | 2000-06-20 | Johns Manville International, Inc. | Emulsified furan resin based glass fiber binding compositions, process of binding glass fibers, and glass fiber compositions |
| US5534612A (en) * | 1992-05-19 | 1996-07-09 | Schuller International, Inc. | Glass fiber binding compositions, process of making glass fiber binding compositions, process of binding glass fibers, and glass fiber compositions |
| EP0642476B1 (en) * | 1992-05-19 | 1996-08-14 | Schuller International, Inc. | Glass fiber binding compositions, process of binding glass fibers, and glass fiber compositions |
| GB2271739B (en) * | 1992-10-22 | 1996-10-23 | Nat Science Council | Process for pultruding fiber reinforced furan composites |
| US5459183A (en) * | 1993-05-19 | 1995-10-17 | Schuller International, Inc. | Low VOC furan resins and method of reducing VOCS in furan resins |
| ES2816451T3 (es) | 2010-12-16 | 2021-04-05 | Huettenes Albertus Chemische Werke Gmbh | Aglutinante de curado en frío de baja emisión para la industria de fundición |
-
1968
- 1968-05-31 US US733282A patent/US3594345A/en not_active Expired - Lifetime
-
1969
- 1969-05-19 GB GB1226065D patent/GB1226065A/en not_active Expired
- 1969-05-30 DE DE1966942A patent/DE1966942C3/de not_active Expired
- 1969-05-30 DE DE19691927776 patent/DE1927776A1/de active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| GB1226065A (enExample) | 1971-03-24 |
| US3594345A (en) | 1971-07-20 |
| DE1966942B2 (de) | 1978-02-16 |
| DE1966942A1 (de) | 1975-12-18 |
| DE1927776A1 (de) | 1969-12-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| EHJ | Ceased/non-payment of the annual fee |