BE632916A - - Google Patents
Info
- Publication number
- BE632916A BE632916A BE632916DA BE632916A BE 632916 A BE632916 A BE 632916A BE 632916D A BE632916D A BE 632916DA BE 632916 A BE632916 A BE 632916A
- Authority
- BE
- Belgium
- Prior art keywords
- acid
- substituted
- phenol
- group
- resinous
- Prior art date
Links
- 239000002253 acid Substances 0.000 claims description 107
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 67
- 239000000203 mixture Substances 0.000 claims description 45
- 239000000047 product Substances 0.000 claims description 29
- 150000007513 acids Chemical class 0.000 claims description 24
- 150000002148 esters Chemical class 0.000 claims description 13
- 125000004432 carbon atoms Chemical group C* 0.000 claims description 12
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N Oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 9
- 239000003921 oil Substances 0.000 claims description 9
- 235000019198 oils Nutrition 0.000 claims description 9
- 235000013824 polyphenols Nutrition 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- 239000011347 resin Substances 0.000 claims description 8
- 229920005989 resin Polymers 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 230000002378 acidificating Effects 0.000 claims description 5
- 239000004359 castor oil Substances 0.000 claims description 5
- 239000005642 Oleic acid Substances 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 235000019438 castor oil Nutrition 0.000 claims description 4
- 235000021388 linseed oil Nutrition 0.000 claims description 4
- 239000000944 linseed oil Substances 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 3
- 239000007859 condensation product Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 238000006116 polymerization reaction Methods 0.000 claims description 3
- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 3
- -1 aliphatic ketoacid Chemical class 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims description 2
- 235000012424 soybean oil Nutrition 0.000 claims description 2
- 239000003549 soybean oil Substances 0.000 claims description 2
- 239000008158 vegetable oil Substances 0.000 claims description 2
- 239000002023 wood Substances 0.000 claims description 2
- 125000005027 hydroxyaryl group Chemical group 0.000 claims 7
- 210000004940 Nucleus Anatomy 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000004435 hydrogen atoms Chemical class [H]* 0.000 claims 2
- 241000590572 Bia <butterfly> Species 0.000 claims 1
- 241000490229 Eucephalus Species 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 150000008442 polyphenolic compounds Chemical class 0.000 claims 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 claims 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 28
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 14
- 238000009835 boiling Methods 0.000 description 12
- 229960000583 Acetic Acid Drugs 0.000 description 10
- 150000002989 phenols Chemical class 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 9
- XTWYTFMLZFPYCI-KQYNXXCUSA-N 5'-adenylphosphoric acid Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O XTWYTFMLZFPYCI-KQYNXXCUSA-N 0.000 description 7
- VKOUCJUTMGHNOR-UHFFFAOYSA-N Diphenolic acid Chemical compound C=1C=C(O)C=CC=1C(CCC(O)=O)(C)C1=CC=C(O)C=C1 VKOUCJUTMGHNOR-UHFFFAOYSA-N 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- OYHQOLUKZRVURQ-IXWMQOLASA-N Linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 150000008064 anhydrides Chemical class 0.000 description 5
- 125000004104 aryloxy group Chemical group 0.000 description 5
- 238000007654 immersion Methods 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- 150000007965 phenolic acids Chemical class 0.000 description 5
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 4
- 229910052803 cobalt Inorganic materials 0.000 description 4
- 239000010941 cobalt Substances 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000011261 inert gas Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- JOOXCMJARBKPKM-UHFFFAOYSA-N Levulinic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 229940040102 levulinic acid Drugs 0.000 description 3
- 235000020778 linoleic acid Nutrition 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000004014 plasticizer Substances 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000003039 volatile agent Substances 0.000 description 3
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N Diphenhydramine Chemical compound C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 2
- 240000007842 Glycine max Species 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive Effects 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 230000005587 bubbling Effects 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 150000001805 chlorine compounds Chemical group 0.000 description 2
- 238000010411 cooking Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 235000009048 phenolic acids Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- 101700078421 ALT4 Proteins 0.000 description 1
- 241000132092 Aster Species 0.000 description 1
- 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 1
- 229910001369 Brass Inorganic materials 0.000 description 1
- 241000273930 Brevoortia tyrannus Species 0.000 description 1
- 206010011416 Croup infectious Diseases 0.000 description 1
- 241000502171 Distylium racemosum Species 0.000 description 1
- 229940013317 Fish Oils Drugs 0.000 description 1
- 240000001962 Intsia bijuga Species 0.000 description 1
- 210000004185 Liver Anatomy 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N Phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 241001125046 Sardina pilchardus Species 0.000 description 1
- 240000008529 Triticum aestivum Species 0.000 description 1
- FRPZMMHWLSIFAZ-UHFFFAOYSA-N Undecylenic acid Chemical group OC(=O)CCCCCCCCC=C FRPZMMHWLSIFAZ-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- PQLVXDKIJBQVDF-UHFFFAOYSA-L acetate;hydroxide Chemical compound [OH-].CC([O-])=O PQLVXDKIJBQVDF-UHFFFAOYSA-L 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 125000004429 atoms Chemical group 0.000 description 1
- MGLRBIFGIFABJB-UHFFFAOYSA-O azanium;hydride Chemical compound [H-].[NH4+] MGLRBIFGIFABJB-UHFFFAOYSA-O 0.000 description 1
- 239000010951 brass Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 239000002361 compost Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 201000010549 croup Diseases 0.000 description 1
- 230000000249 desinfective Effects 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxyl anion Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000004715 keto acids Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 235000019837 monoammonium phosphate Nutrition 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 230000003287 optical Effects 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000003415 peat Substances 0.000 description 1
- 239000011505 plaster Substances 0.000 description 1
- 230000001105 regulatory Effects 0.000 description 1
- 238000003303 reheating Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 235000019512 sardine Nutrition 0.000 description 1
- 235000015096 spirit Nutrition 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 235000021307 wheat Nutrition 0.000 description 1
- 239000008096 xylene 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
- 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
- C08G63/06—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from hydroxycarboxylic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Paints Or Removers (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE632916A true BE632916A (nl) |
Family
ID=200706
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE632916D BE632916A (nl) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE632916A (nl) |
-
0
- BE BE632916D patent/BE632916A/fr unknown
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