GB971710A - Process for the preparation of esters and polyesters - Google Patents
Process for the preparation of esters and polyestersInfo
- Publication number
- GB971710A GB971710A GB4257561A GB4257561A GB971710A GB 971710 A GB971710 A GB 971710A GB 4257561 A GB4257561 A GB 4257561A GB 4257561 A GB4257561 A GB 4257561A GB 971710 A GB971710 A GB 971710A
- Authority
- GB
- United Kingdom
- Prior art keywords
- anhydrides
- anhydride
- phthalic
- cyclohexene
- unsaturated
- 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
- 150000002148 esters Chemical class 0.000 title abstract 7
- 229920000728 polyester Polymers 0.000 title abstract 3
- 150000008064 anhydrides Chemical class 0.000 abstract 17
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract 12
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 abstract 10
- 150000001241 acetals Chemical class 0.000 abstract 8
- 239000000203 mixture Substances 0.000 abstract 8
- LGRFSURHDFAFJT-UHFFFAOYSA-N phthalic anhydride Chemical class C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 abstract 8
- 150000001875 compounds Chemical class 0.000 abstract 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 6
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 abstract 6
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 abstract 6
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical class O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 abstract 6
- DUCKXCGALKOSJF-UHFFFAOYSA-N pentanoyl pentanoate Chemical compound CCCCC(=O)OC(=O)CCCC DUCKXCGALKOSJF-UHFFFAOYSA-N 0.000 abstract 6
- 125000004432 carbon atom Chemical group C* 0.000 abstract 5
- JPSKCQCQZUGWNM-UHFFFAOYSA-N 2,7-Oxepanedione Chemical compound O=C1CCCCC(=O)O1 JPSKCQCQZUGWNM-UHFFFAOYSA-N 0.000 abstract 4
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 abstract 4
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 abstract 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 4
- 239000003054 catalyst Substances 0.000 abstract 4
- 238000006243 chemical reaction Methods 0.000 abstract 4
- 230000032050 esterification Effects 0.000 abstract 4
- 238000005886 esterification reaction Methods 0.000 abstract 4
- 239000004014 plasticizer Substances 0.000 abstract 4
- UFLUQMITNBPFGS-UHFFFAOYSA-N 4-cyclohex-2-en-1-ylbut-3-ene-1,2,3-triol Chemical compound C(C1CCCC=C1)=C(O)C(O)CO UFLUQMITNBPFGS-UHFFFAOYSA-N 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- 150000007513 acids Chemical class 0.000 abstract 3
- 150000001735 carboxylic acids Chemical class 0.000 abstract 3
- 229920006395 saturated elastomer Polymers 0.000 abstract 3
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 abstract 2
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 abstract 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 2
- 230000001476 alcoholic effect Effects 0.000 abstract 2
- 150000001298 alcohols Chemical class 0.000 abstract 2
- 150000001299 aldehydes Chemical class 0.000 abstract 2
- 125000001931 aliphatic group Chemical group 0.000 abstract 2
- 229920000180 alkyd Polymers 0.000 abstract 2
- 150000001408 amides Chemical class 0.000 abstract 2
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 abstract 2
- 125000004185 ester group Chemical group 0.000 abstract 2
- 150000002170 ethers Chemical class 0.000 abstract 2
- 238000010438 heat treatment Methods 0.000 abstract 2
- 229930195733 hydrocarbon Natural products 0.000 abstract 2
- 150000002430 hydrocarbons Chemical class 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 abstract 2
- 150000003949 imides Chemical class 0.000 abstract 2
- 150000002576 ketones Chemical class 0.000 abstract 2
- 150000002763 monocarboxylic acids Chemical class 0.000 abstract 2
- 150000002825 nitriles Chemical class 0.000 abstract 2
- 239000003960 organic solvent Substances 0.000 abstract 2
- 150000002989 phenols Chemical class 0.000 abstract 2
- 150000003014 phosphoric acid esters Chemical class 0.000 abstract 2
- 229920000915 polyvinyl chloride Polymers 0.000 abstract 2
- 239000004800 polyvinyl chloride Substances 0.000 abstract 2
- 239000011541 reaction mixture Substances 0.000 abstract 2
- 239000007858 starting material Substances 0.000 abstract 2
- 239000001117 sulphuric acid Substances 0.000 abstract 2
- 235000011149 sulphuric acid Nutrition 0.000 abstract 2
- 229920006305 unsaturated polyester Polymers 0.000 abstract 2
- 239000008096 xylene Substances 0.000 abstract 2
- TZZZLCLJMCLVTJ-UHFFFAOYSA-N 4-cyclohex-2-en-1-ylbutane-1,2,3-triol Chemical compound C(C1CCCC=C1)C(O)C(O)CO TZZZLCLJMCLVTJ-UHFFFAOYSA-N 0.000 abstract 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 abstract 1
- YXEBFFWTZWGHEY-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohex-3-en-1-yl]methanol Chemical compound OCC1(CO)CCC=CC1 YXEBFFWTZWGHEY-UHFFFAOYSA-N 0.000 abstract 1
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 abstract 1
- 125000000466 oxiranyl group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/08—1,3-Dioxanes; Hydrogenated 1,3-dioxanes condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
-
- 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
- C08G63/40—Polyesters derived from ester-forming derivatives of polycarboxylic acids or of polyhydroxy compounds, other than from esters thereof
- C08G63/42—Cyclic ethers; Cyclic carbonates; Cyclic sulfites; Cyclic orthoesters
-
- 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
- C08G63/52—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
-
- 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
- C08G63/52—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
- C08G63/54—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation the acids or hydroxy compounds containing carbocyclic 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
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/52—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
- C08G63/56—Polyesters derived from ester-forming derivatives of polycarboxylic acids or of polyhydroxy compounds other than from esters thereof
- C08G63/58—Cyclic ethers; Cyclic carbonates; Cyclic sulfites ; Cyclic orthoesters
-
- 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
- C08G63/66—Polyesters containing oxygen in the form of ether groups
- C08G63/668—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/676—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L27/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers
- C08L27/02—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L27/04—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment containing chlorine atoms
- C08L27/06—Homopolymers or copolymers of vinyl chloride
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyesters Or Polycarbonates (AREA)
Abstract
Esters and polyesters are prepared by reacting an olefinically or cyclo-olefinically unsaturated compound containing at least three carbon atoms with hydrogen peroxide and an anhydride or mixture of anhydrides derived from one or more mono- or polycarboxylic acids containing at least 4 carbon atoms, if desired in the presence of an esterification catalyst until no substantial amount of oxinane groups can be detected in the reaction mixture. The products have a high content of ester groups derived from secondary alcoholic hydroxyl groups. Unsaturated compounds used as starting materials are listed under the headings hydrocarbons, chlorinated hydrocarbons, alcohols and phenols, ethers, esters, aldehydes and ketones, acetals, amides, imides, nitriles and unsaturated phosphoric acid esters and many anhydrides are also listed. Anhydrides of mono-carboxylic acids yield esters which may be used as plasticizers, anhydrides of unsaturated di- or poly-carboxylic acids or mixtures thereof form copolymerizable unsaturated polyesters, and mixtures of monocarboxylic acid anhydrides and anhydrides of di- or poly-carboxylic acids form alkyd resins. The reaction may be performed in an inert organic solvent or in solution in an excess of the olefinically unsaturated compound with or without an esterification catalyst and the hydrogen peroxide is in a solution of 30 to 85 per cent strength. Examples describe the reaction of an acetal of D 3-tetrahydrobenzaldehyde and 1:1-bis-(hydroxymethyl)-cyclohex-3-ene <FORM:0971710/C1/1> with a mixture of phthalic and maleic anhydrides; phenylbutane-2:3 with hexahydrophthalic and maleic anhydrides, polymeric adipic and maleic anhydrides, polymeric adipic anhydride alone, and valeric anhydride alone; styrene with maleic and phthalic anhydrides; the acetal 3-vinyl-2:4-dioxospiro(5:5)-undecene-9 of formula <FORM:0971710/C1/2> with phthalic anhydride, or hexahydrophthalic anhydride; tetrahydrobenzyl glycerol with phthalic anhydride; cyclohexene with polymeric adipic anhydride; an addition product of xylene and butadiene with C9-C11 saturated mixed aliphatic monocarboxylic anhydrides and phthalic anhydride; tetrahydrobenzal glycerol and the C9-C11, mixed anhydrides above; dicyclopentadiene and valeric anhydride; cyclohexene and valeric anhydride; and cyclohexane and C9-C11 mixed anhydrides above, together with hydrogen peroxide. The latter ester may be used as a plasticizer for polyvinyl chloride. The acetal, 3-vinyl-2:4-dioxospiro (5:5)-undecene-9 is prepared by heating 1:1-bis-[hydroxymethyl]-cyclohexene-3, acrolein, and benzene in the presence of sulphuric acid. Specifications 758,728, 790,063 and 876,489 are referred to.ALSO:Polyesters are prepared by reacting an olefinically or cyclo-olefinically unsaturated compound containing at least three carbon atoms with hydrogen peroxide and an anhydride or mixture of anhydrides derived from one or more mono- or poly-carboxylic acids containing at least 4 carbon atoms, if desired in the presence of an esterification catalyst, until no substantial amount of oxirane groups can be detected in the reaction mixture. Copolymerizable unsaturated polyesters are prepared with anhydrides of unsaturated di- or polycarboxylic acids, or mixtures thereof, and alkyd resins by reacting the unsaturated compounds with mixtures of anhydrides of mono-carboxylic acids and saturated di- or polycarboxylic acids both containing at least 4 carbon atoms. The products have a high content of ester groups, derived from secondary, alcoholic hydroxyl groups and may be used as plasticizers. Unsaturated compounds used as starting materials are listed under headings, hydrocarbons, chlorinated hydrocarbons, alcohols, and phenols, ethers, esters, aldehydes and ketones, acetals, amides, imides, nitriles and unsaturated phosphoric acid esters and many anhydrides are also listed. The reaction may be performed in an inert organic solvent or in solution in an excess of the olefinically unsaturated compound with or without an esterification catalyst and the hydrogen peroxide is in a solution of 30 to 85% strength. Examples describe the reaction of an acetal of D 3-tetrahydrobenzaldehyde and 1,1-bis-(hydroxymethyl)-cyclohex-3-ene <FORM:0971710/C3/1> with a mixture of phthalic and maleic anhydrides; phenylbutene-2:3 with hexahydrophthalic and maleic anhydrides, polymeric adipic and maleic anhydrides, polymeric adipic anhydride alone, and valeric anhydride alone; styrene with maleic and phthalic anhydrides; the acetal 3-vinyl-2:4-dioxospiro (5:5)-undecene-9 of formula <FORM:0971710/C3/2> with phthalic anhydride or hexahydrophthalic anhydride; tetrahydrobenzal glycerol with phthalic anhydride; cyclohexene with polymeric adipic anhydride; an addition product of xylene and butadiene with C9-C11 saturated mixed aliphatic monocarboxylic anhydrides and phthalic anhydride; tetrahydrobenzal glycerol and the C9-C11 mixed anhydrides above; dicyclopentadiene and valeric anhydride; cyclohexene and valeric anhydride; and cyclohexene and C9-C11 mixed anhydrides together with hydrogen peroxide. The latter ester may be used as a plasticizer for polyvinyl chloride. The acetal 3 vinyl-2:4-dioxospiro (5:5)-undecane-9; is prepared by heating 1:1-bis-[hydroxymethyl]-cyclohexene-3, acrolein, and benzene in the presence of sulphuric acid. Specifications 758,728, 790,063 and 876,489 are referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1336060A CH418319A (en) | 1960-11-29 | 1960-11-29 | Process for the preparation of esters and polyesters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB971710A true GB971710A (en) | 1964-10-07 |
Family
ID=4391747
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4257561A Expired GB971710A (en) | 1960-11-29 | 1961-11-28 | Process for the preparation of esters and polyesters |
Country Status (5)
| Country | Link |
|---|---|
| AT (1) | AT243514B (en) |
| CH (1) | CH418319A (en) |
| DE (1) | DE1217615B (en) |
| GB (1) | GB971710A (en) |
| NL (1) | NL271902A (en) |
-
0
- NL NL271902D patent/NL271902A/xx unknown
-
1960
- 1960-11-29 CH CH1336060A patent/CH418319A/en unknown
-
1961
- 1961-11-28 AT AT902761A patent/AT243514B/en active
- 1961-11-28 DE DEC25622A patent/DE1217615B/en active Pending
- 1961-11-28 GB GB4257561A patent/GB971710A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL271902A (en) | |
| AT243514B (en) | 1965-11-10 |
| CH418319A (en) | 1966-08-15 |
| DE1217615B (en) | 1966-05-26 |
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