GB818810A - Bituminous compositions - Google Patents
Bituminous compositionsInfo
- Publication number
- GB818810A GB818810A GB28384/57A GB2838457A GB818810A GB 818810 A GB818810 A GB 818810A GB 28384/57 A GB28384/57 A GB 28384/57A GB 2838457 A GB2838457 A GB 2838457A GB 818810 A GB818810 A GB 818810A
- Authority
- GB
- United Kingdom
- Prior art keywords
- bis
- heating
- catalyst
- acids
- polymerized
- 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
- 239000000203 mixture Substances 0.000 title abstract 2
- 238000010438 heat treatment Methods 0.000 abstract 7
- 239000002253 acid Substances 0.000 abstract 5
- 239000003054 catalyst Substances 0.000 abstract 5
- 229920000570 polyether Polymers 0.000 abstract 5
- 239000004593 Epoxy Substances 0.000 abstract 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 abstract 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 abstract 4
- 150000007513 acids Chemical class 0.000 abstract 3
- 229920001577 copolymer Polymers 0.000 abstract 3
- 235000014113 dietary fatty acids Nutrition 0.000 abstract 3
- 229930195729 fatty acid Natural products 0.000 abstract 3
- 239000000194 fatty acid Substances 0.000 abstract 3
- 150000004665 fatty acids Chemical class 0.000 abstract 3
- 229930185605 Bisphenol Natural products 0.000 abstract 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 abstract 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 2
- 239000004721 Polyphenylene oxide Substances 0.000 abstract 2
- 239000010426 asphalt Substances 0.000 abstract 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 abstract 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 abstract 2
- 239000000178 monomer Substances 0.000 abstract 2
- 150000002989 phenols Chemical class 0.000 abstract 2
- DTRGDWOPRCXRET-UHFFFAOYSA-N (9Z,11E,13E)-4-Oxo-9,11,13-octadecatrienoic acid Natural products CCCCC=CC=CC=CCCCCC(=O)CCC(O)=O DTRGDWOPRCXRET-UHFFFAOYSA-N 0.000 abstract 1
- CUXYLFPMQMFGPL-UHFFFAOYSA-N (9Z,11E,13E)-9,11,13-Octadecatrienoic acid Natural products CCCCC=CC=CC=CCCCCCCCC(O)=O CUXYLFPMQMFGPL-UHFFFAOYSA-N 0.000 abstract 1
- DTRGDWOPRCXRET-SUTYWZMXSA-N (9e,11e,13e)-4-oxooctadeca-9,11,13-trienoic acid Chemical compound CCCC\C=C\C=C\C=C\CCCCC(=O)CCC(O)=O DTRGDWOPRCXRET-SUTYWZMXSA-N 0.000 abstract 1
- HCNHNBLSNVSJTJ-UHFFFAOYSA-N 1,1-Bis(4-hydroxyphenyl)ethane Chemical compound C=1C=C(O)C=CC=1C(C)C1=CC=C(O)C=C1 HCNHNBLSNVSJTJ-UHFFFAOYSA-N 0.000 abstract 1
- URFNSYWAGGETFK-UHFFFAOYSA-N 1,2-bis(4-hydroxyphenyl)ethane Natural products C1=CC(O)=CC=C1CCC1=CC=C(O)C=C1 URFNSYWAGGETFK-UHFFFAOYSA-N 0.000 abstract 1
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-dioxonaphthalene Natural products C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 abstract 1
- BOKGTLAJQHTOKE-UHFFFAOYSA-N 1,5-dihydroxynaphthalene Chemical compound C1=CC=C2C(O)=CC=CC2=C1O BOKGTLAJQHTOKE-UHFFFAOYSA-N 0.000 abstract 1
- WSMDPBKOWAHQGV-UHFFFAOYSA-N 1-[2-(2-hydroxynaphthalen-1-yl)pentan-2-yl]naphthalen-2-ol Chemical compound C1=CC=C2C(C(C)(C=3C4=CC=CC=C4C=CC=3O)CCC)=C(O)C=CC2=C1 WSMDPBKOWAHQGV-UHFFFAOYSA-N 0.000 abstract 1
- ZTMADXFOCUXMJE-UHFFFAOYSA-N 2-methylbenzene-1,3-diol Chemical compound CC1=C(O)C=CC=C1O ZTMADXFOCUXMJE-UHFFFAOYSA-N 0.000 abstract 1
- QSMHTOCQXUAUFB-UHFFFAOYSA-N 3-tert-butyl-4-[2-(2-tert-butyl-4-hydroxyphenyl)propan-2-yl]phenol Chemical compound CC(C)(C)C1=CC(O)=CC=C1C(C)(C)C1=CC=C(O)C=C1C(C)(C)C QSMHTOCQXUAUFB-UHFFFAOYSA-N 0.000 abstract 1
- XILNKQWGKMTFFA-UHFFFAOYSA-N 4-[2-(4-hydroxy-2-methylphenyl)propan-2-yl]-3-methylphenol Chemical compound CC1=CC(O)=CC=C1C(C)(C)C1=CC=C(O)C=C1C XILNKQWGKMTFFA-UHFFFAOYSA-N 0.000 abstract 1
- HTVITOHKHWFJKO-UHFFFAOYSA-N Bisphenol B Chemical compound C=1C=C(O)C=CC=1C(C)(CC)C1=CC=C(O)C=C1 HTVITOHKHWFJKO-UHFFFAOYSA-N 0.000 abstract 1
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- CUXYLFPMQMFGPL-SUTYWZMXSA-N all-trans-octadeca-9,11,13-trienoic acid Chemical compound CCCC\C=C\C=C\C=C\CCCCCCCC(O)=O CUXYLFPMQMFGPL-SUTYWZMXSA-N 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- OZBVOUJIBRYLRW-UHFFFAOYSA-N benzene-1,4-diol;methane Chemical compound C.OC1=CC=C(O)C=C1.OC1=CC=C(O)C=C1 OZBVOUJIBRYLRW-UHFFFAOYSA-N 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- BVURNMLGDQYNAF-UHFFFAOYSA-N dimethyl(1-phenylethyl)amine Chemical compound CN(C)C(C)C1=CC=CC=C1 BVURNMLGDQYNAF-UHFFFAOYSA-N 0.000 abstract 1
- 239000001282 iso-butane Substances 0.000 abstract 1
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 abstract 1
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- ASHGTJPOSUFTGB-UHFFFAOYSA-N methyl resorcinol Natural products COC1=CC=CC(O)=C1 ASHGTJPOSUFTGB-UHFFFAOYSA-N 0.000 abstract 1
- JBYXPOFIGCOSSB-UHFFFAOYSA-N octadeca-9,11-dienoic acid Chemical class CCCCCCC=CC=CCCCCCCCC(O)=O JBYXPOFIGCOSSB-UHFFFAOYSA-N 0.000 abstract 1
- DTOSIQBPPRVQHS-UHFFFAOYSA-N α-Linolenic acid Chemical compound CCC=CCC=CCC=CCCCCCCCC(O)=O DTOSIQBPPRVQHS-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L95/00—Compositions of bituminous materials, e.g. asphalt, tar, pitch
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Civil Engineering (AREA)
- Materials Engineering (AREA)
- Structural Engineering (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Epoxy Resins (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Copolymers of glycidy polyethers (1.2 epoxy equivalency greater than 1) of a polyhydric phenol with a polymerized conjugated fatty acid are obtained by precondensing the epoxy compound with the acid by preliminary heating in the absence of a catalyst, adding the catalyst, and further heating. For example, trimerized 9,11 octadecadienoic acids and liquid glycidyl polyether of 2,2 bis (4-hydroxyphenyl) propane are heated at 100 DEG C. and alpha methyl benzyl dimethylamine (as catalyst) then added with further heating at 100 DEG C. Specified phenols for preparing the polyethers are resorcinol; methyl resorcinol; catechol; hydroquinone; 4,41-dihydroxy benzophenone; bis (4-hydroxyphenol) methane; 1-1 bis (4-hydroxyphenyl) ethane, and isobutane; 2,2 bis (4-hydroxyphenyl) butane; 2,2 bis (4-hydroxy-2-methyl phenyl) propane; 2,2 bis (4-hydroxy 2-tertiary butylphenyl) propane; 2,2 bis (2-hydroxynaphthyl) pentane; and 1,5 dihydroxynaphthalene. The polymerized acids are prepared by heating, e.g. their lower aliphatic esters, and the monomer acids preferably have 16 to 24 carbon atoms, e.g. linoleic, linolenic, eleostearic and licanic acid.ALSO:A bituminous composition consists of an asphaltic bitumen and a copolymer of a glycidyl polyether, having a 1, 2 epoxy equivalency greater than 1, of a polyhydric phenol with a polymerized conjugated fatty acid. Between 0,5 and 75 per cent. of copolymer can be present. Preferably the epoxy and acid compounds are precondensed by heating in the absence of a catalyst the bitumen being present or not. Subsequently, heating is continued in the presence of a catalyst e.g. an amine. Amongst the phenols specified are mononuclear, e.g. resorcinol, and polynuclear ones, e.g. bis-phenol, the preferred polyethers being prepared from bis phenol. The polymerized acids are obtained from conjugated fatty acids by heating under known conditions, the monomers containing 16 to 24 C. atoms.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US818810XA | 1956-09-10 | 1956-09-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB818810A true GB818810A (en) | 1959-08-26 |
Family
ID=22166993
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB28384/57A Expired GB818810A (en) | 1956-09-10 | 1957-09-09 | Bituminous compositions |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB818810A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1272477B (en) * | 1960-08-24 | 1968-07-11 | Shell Int Research | Process for the production of coating and impregnating agents |
-
1957
- 1957-09-09 GB GB28384/57A patent/GB818810A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1272477B (en) * | 1960-08-24 | 1968-07-11 | Shell Int Research | Process for the production of coating and impregnating agents |
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