GB1022870A - Organic compounds - Google Patents
Organic compoundsInfo
- Publication number
- GB1022870A GB1022870A GB46930/63A GB4693063A GB1022870A GB 1022870 A GB1022870 A GB 1022870A GB 46930/63 A GB46930/63 A GB 46930/63A GB 4693063 A GB4693063 A GB 4693063A GB 1022870 A GB1022870 A GB 1022870A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- derivatives
- bis
- dimethyl
- derivative
- 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
- 150000002894 organic compounds Chemical class 0.000 title 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 abstract 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 abstract 2
- MMEDJBFVJUFIDD-UHFFFAOYSA-N 2-[2-(carboxymethyl)phenyl]acetic acid Chemical compound OC(=O)CC1=CC=CC=C1CC(O)=O MMEDJBFVJUFIDD-UHFFFAOYSA-N 0.000 abstract 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 abstract 1
- LABJFIBQJFPXHZ-UHFFFAOYSA-N 4-(carboxymethoxy)benzoic acid Chemical compound OC(=O)COC1=CC=C(C(O)=O)C=C1 LABJFIBQJFPXHZ-UHFFFAOYSA-N 0.000 abstract 1
- VTDMBRAUHKUOON-UHFFFAOYSA-N 4-[(4-carboxyphenyl)methyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1CC1=CC=C(C(O)=O)C=C1 VTDMBRAUHKUOON-UHFFFAOYSA-N 0.000 abstract 1
- VAXBLYWAVAIJJJ-UHFFFAOYSA-N 4-[2-(4-carboxyphenoxy)ethoxy]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1OCCOC1=CC=C(C(O)=O)C=C1 VAXBLYWAVAIJJJ-UHFFFAOYSA-N 0.000 abstract 1
- ZUHSOFSNAPZWOG-UHFFFAOYSA-N 4-[[4-[(4-carboxyphenoxy)methyl]cyclohexyl]methoxy]benzoic acid Chemical compound C(=O)(O)C1=CC=C(OCC2CCC(CC2)COC2=CC=C(C=C2)C(=O)O)C=C1 ZUHSOFSNAPZWOG-UHFFFAOYSA-N 0.000 abstract 1
- 229930185605 Bisphenol Natural products 0.000 abstract 1
- 229910010084 LiAlH4 Inorganic materials 0.000 abstract 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 abstract 1
- GZRLHHWPHFXQPF-UHFFFAOYSA-N [8a-(hydroxymethyl)-1,2,3,4,5,6,7,8-octahydronaphthalen-4a-yl]methanol Chemical compound C1CCCC2(CO)CCCCC21CO GZRLHHWPHFXQPF-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- -1 decahydronaphthalene dicarboxylic acid esters Chemical class 0.000 abstract 1
- RBLSQHNMLLTHMH-UHFFFAOYSA-N dibenzofuran-2,8-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=C2C3=CC(C(=O)O)=CC=C3OC2=C1 RBLSQHNMLLTHMH-UHFFFAOYSA-N 0.000 abstract 1
- 125000003963 dichloro group Chemical group Cl* 0.000 abstract 1
- JGJWEXOAAXEJMW-UHFFFAOYSA-N dimethyl naphthalene-1,2-dicarboxylate Chemical class C1=CC=CC2=C(C(=O)OC)C(C(=O)OC)=CC=C21 JGJWEXOAAXEJMW-UHFFFAOYSA-N 0.000 abstract 1
- 150000002009 diols Chemical class 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 1
- 125000001153 fluoro group Chemical group F* 0.000 abstract 1
- 150000002334 glycols Chemical class 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 239000012280 lithium aluminium hydride Substances 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 1
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical class C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 abstract 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 abstract 1
- 229920000728 polyester Polymers 0.000 abstract 1
- 239000001294 propane Substances 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- TXXHDPDFNKHHGW-ZPUQHVIOSA-N trans,trans-muconic acid Chemical compound OC(=O)\C=C\C=C\C(O)=O TXXHDPDFNKHHGW-ZPUQHVIOSA-N 0.000 abstract 1
- NNBZCPXTIHJBJL-UHFFFAOYSA-N trans-decahydronaphthalene Natural products C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 abstract 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/16—Dicarboxylic acids and dihydroxy compounds
- C08G63/18—Dicarboxylic acids and dihydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
- C08G63/199—Acids or hydroxy compounds containing cycloaliphatic rings
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/60—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from the reaction of a mixture of hydroxy carboxylic acids, polycarboxylic acids and polyhydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
- C08L67/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyesters Or Polycarbonates (AREA)
Abstract
Linear polyesters comprise recurring units of formula <FORM:1022870/C3/1> wherein -CH2-C10H16-CH2- is a decahydrobis(methylene)-naphthalene radical and A is a C6-24 divalent radical inert in esterification reaction. Suitable reactants providing the residue A are 4,41-bibenzoic acid, its dodecahydro derivative, its 2,21 and 3,31 dimethyl derivatives and its 2,21-dibromo derivative; bis(4-carboxyphenyl)-methane, -ethane, -propane, -ketone, -ether, -sulphide, -sulphonide and -sulphone; 1,2 - bis(4 - carboxyphenoxy)-ethane; 2,8 - dibenzofurandicarboxylic acid; terephthalic acid and its hexahydro methyl, dimethyl, fluoro, chloro or dichloro derivatives; isophthalic acid and its 5-sulpho, -chloro and -t-butyl derivatives; naphthalenedicarboxylic acids and their decahydro derivatives; phenylenediacetic acid; 4-carboxyphenoxyacetic acid; m- and p-terphenyl-4,411-dicarboxylic acids and the m-perhydro derivative; bicyclo(2,2,2)octane 1,4-dicarboxylic acid; 4,41-stilbenedicarboxylic acid; 1,4 - bis(4 - carboxyphenoxymethyl)-cyclohexane. With the dimethyloldecahydronaphthalene component there may be copolymerized other hydroxy components such as glycols or bisphenols of which a number of examples are given.ALSO:The invention comprises the title compounds, excepting the 1,2-isomer, these being prepared by ring hydrogenating dimethyl naphthalenedicarboxylates with Ru/C and reducing the decahydronaphthalene dicarboxylic acid esters thus obtained to the corresponding diols with LiAlH4.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB46930/63A GB1022870A (en) | 1963-11-27 | 1963-11-27 | Organic compounds |
| FR956197A FR1385610A (en) | 1963-11-27 | 1963-12-05 | New glycols derived from naphthalene and polyesters made from these glycols |
| DEP33148A DE1282845B (en) | 1963-11-27 | 1963-12-06 | Use of Carbonyloxy Polyesters for making threads or foils |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB46930/63A GB1022870A (en) | 1963-11-27 | 1963-11-27 | Organic compounds |
| FR956197A FR1385610A (en) | 1963-11-27 | 1963-12-05 | New glycols derived from naphthalene and polyesters made from these glycols |
| DEP33148A DE1282845B (en) | 1963-11-27 | 1963-12-06 | Use of Carbonyloxy Polyesters for making threads or foils |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1022870A true GB1022870A (en) | 1966-03-16 |
Family
ID=26204728
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB46930/63A Expired GB1022870A (en) | 1963-11-27 | 1963-11-27 | Organic compounds |
Country Status (3)
| Country | Link |
|---|---|
| DE (1) | DE1282845B (en) |
| FR (1) | FR1385610A (en) |
| GB (1) | GB1022870A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010148080A3 (en) * | 2009-06-16 | 2011-09-29 | Draths Corporation | Cyclohexane 1,4 carboxylates |
| US8367858B2 (en) | 2009-06-16 | 2013-02-05 | Amyris, Inc. | Terephthalic and trimellitic based acids and carboxylate derivatives thereof |
| US8415496B2 (en) | 2009-06-16 | 2013-04-09 | Amyris, Inc. | Biobased polyesters |
| US8426639B2 (en) | 2009-06-16 | 2013-04-23 | Amyris, Inc. | Preparation of trans, trans muconic acid and trans, trans muconates |
| US8809583B2 (en) | 2010-01-08 | 2014-08-19 | Amyris, Inc. | Methods for producing isomers of muconic acid and muconate salts |
-
1963
- 1963-11-27 GB GB46930/63A patent/GB1022870A/en not_active Expired
- 1963-12-05 FR FR956197A patent/FR1385610A/en not_active Expired
- 1963-12-06 DE DEP33148A patent/DE1282845B/en active Pending
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010148080A3 (en) * | 2009-06-16 | 2011-09-29 | Draths Corporation | Cyclohexane 1,4 carboxylates |
| US8367859B2 (en) | 2009-06-16 | 2013-02-05 | Amyris, Inc. | Cyclohexane 1,4 carboxylates |
| US8367858B2 (en) | 2009-06-16 | 2013-02-05 | Amyris, Inc. | Terephthalic and trimellitic based acids and carboxylate derivatives thereof |
| US8415496B2 (en) | 2009-06-16 | 2013-04-09 | Amyris, Inc. | Biobased polyesters |
| US8426639B2 (en) | 2009-06-16 | 2013-04-23 | Amyris, Inc. | Preparation of trans, trans muconic acid and trans, trans muconates |
| US8809583B2 (en) | 2010-01-08 | 2014-08-19 | Amyris, Inc. | Methods for producing isomers of muconic acid and muconate salts |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1385610A (en) | 1965-01-15 |
| DE1282845B (en) | 1969-02-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ATE27471T1 (en) | PLIABLE LAMINATE. | |
| JPS55131049A (en) | Novel thermoplastic resin composition | |
| GB870095A (en) | Linear copolyesters | |
| TW200305591A (en) | Unsaturated, amorphous polyesters based on certain dicidol isomers | |
| GB1022870A (en) | Organic compounds | |
| GB1043313A (en) | Copolyesters | |
| US3592841A (en) | Keto-carboxylic acids | |
| GB978172A (en) | Improvements in or relating to the preparation of diesters of phthalic acids | |
| GB1211817A (en) | Unsaturated polyester compositions | |
| ES368472A1 (en) | Adducts containing epoxide groups from polyepoxide compounds and acid polyesters of aliphatic cycloaliphatic dicarboxylic acids | |
| GB1049030A (en) | Improvements in or relating to stoving varnishes | |
| US3179608A (en) | Alkyd resin with fungicidal property | |
| GB1428420A (en) | Flame retardant polyesters and thermosetting compositions based thereon | |
| US3457235A (en) | Polyester compositions prepared from new 9,10-bridged anthracene compounds | |
| GB1101380A (en) | Epoxy resin compositions | |
| GB1005996A (en) | Process for the production of optically brightened polyesters of terephthalic acid | |
| GB979401A (en) | Improvements relating to glycols and their derivatives | |
| GB968930A (en) | Unsaturated polyesters and monomeric ethylenically-unsaturated compounds co-polymerisable therewith | |
| GB968223A (en) | Process for the preparation of alkyd resins | |
| AT247609B (en) | Process for the production of moldings and coatings with a tack-free surface | |
| GB1042476A (en) | Process for preparing linear polyesters | |
| FR2008217A1 (en) | Cured resin articles from non-aromatic polyepoxide | |
| GB1094723A (en) | Flame-retardant resin materials and new halogen-containing flame-retardant esters | |
| US3113933A (en) | Process for preparing unsaturated polyesters which contain an endomethylenephthalyl alcohol as a glycol component | |
| FR2102308A1 (en) | Polycondensation catalyst - for colourless polyester prepn consisting of polymeric germanium hydride |