CH503094A - Verfahren zur Herstellung eines verbesserten Harzbindemittels für Einbrennlacke - Google Patents
Verfahren zur Herstellung eines verbesserten Harzbindemittels für EinbrennlackeInfo
- Publication number
- CH503094A CH503094A CH442768A CH442768A CH503094A CH 503094 A CH503094 A CH 503094A CH 442768 A CH442768 A CH 442768A CH 442768 A CH442768 A CH 442768A CH 503094 A CH503094 A CH 503094A
- Authority
- CH
- Switzerland
- Prior art keywords
- dicarboxylic acid
- acid
- anhydride
- weight
- mono
- Prior art date
Links
- 229920005989 resin Polymers 0.000 title claims abstract description 12
- 239000011347 resin Substances 0.000 title claims abstract description 12
- 210000003298 dental enamel Anatomy 0.000 title claims abstract description 8
- 239000011230 binding agent Substances 0.000 title claims abstract description 5
- 229920001577 copolymer Polymers 0.000 title claims description 21
- -1 glycidyl ester Chemical class 0.000 claims abstract description 10
- 150000008064 anhydrides Chemical class 0.000 claims abstract description 9
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims abstract description 7
- 150000005690 diesters Chemical class 0.000 claims abstract description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 28
- 239000002253 acid Substances 0.000 claims description 14
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 14
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 11
- 229920000570 polyether Polymers 0.000 claims description 11
- 150000001991 dicarboxylic acids Chemical class 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 230000032050 esterification Effects 0.000 claims description 2
- 238000005886 esterification reaction Methods 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 150000001735 carboxylic acids Chemical class 0.000 abstract 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 20
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 18
- 239000000178 monomer Substances 0.000 description 13
- 239000007787 solid Substances 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 229920000877 Melamine resin Polymers 0.000 description 10
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 10
- 238000007334 copolymerization reaction Methods 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- 239000004640 Melamine resin Substances 0.000 description 9
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 9
- 239000008096 xylene Substances 0.000 description 9
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 8
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 8
- 229940072282 cardura Drugs 0.000 description 7
- RUZYUOTYCVRMRZ-UHFFFAOYSA-N doxazosin Chemical compound C1OC2=CC=CC=C2OC1C(=O)N(CC1)CCN1C1=NC(N)=C(C=C(C(OC)=C2)OC)C2=N1 RUZYUOTYCVRMRZ-UHFFFAOYSA-N 0.000 description 7
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 7
- 239000002243 precursor Substances 0.000 description 7
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 6
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 238000009835 boiling Methods 0.000 description 4
- 239000003973 paint Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 3
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 3
- 239000001530 fumaric acid Substances 0.000 description 3
- 229920001187 thermosetting polymer Polymers 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 235000010215 titanium dioxide Nutrition 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- VHSHLMUCYSAUQU-UHFFFAOYSA-N 2-hydroxypropyl methacrylate Chemical compound CC(O)COC(=O)C(C)=C VHSHLMUCYSAUQU-UHFFFAOYSA-N 0.000 description 1
- OAOABCKPVCUNKO-UHFFFAOYSA-N 8-methyl Nonanoic acid Chemical compound CC(C)CCCCCCC(O)=O OAOABCKPVCUNKO-UHFFFAOYSA-N 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000012986 chain transfer agent Substances 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
- 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 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 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
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000004383 yellowing 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
- C08G18/6216—Polymers of alpha-beta ethylenically unsaturated carboxylic acids or of derivatives thereof
- C08G18/622—Polymers of esters of alpha-beta ethylenically unsaturated carboxylic acids
- C08G18/6241—Polymers of esters containing hydroxy groups of alpha-beta ethylenically unsaturated carboxylic acids with epoxy compounds other than alkylene oxides and hydroxyglycidyl compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—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 carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/12—Esters of phenols or saturated alcohols
- C08F222/20—Esters containing oxygen in addition to the carboxy oxygen
-
- 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/331—Polymers modified by chemical after-treatment with organic compounds containing oxygen
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Polyesters Or Polycarbonates (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL6704630A NL6704630A (forum.php) | 1967-03-31 | 1967-03-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH503094A true CH503094A (de) | 1971-02-15 |
Family
ID=19799717
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH442768A CH503094A (de) | 1967-03-31 | 1968-03-26 | Verfahren zur Herstellung eines verbesserten Harzbindemittels für Einbrennlacke |
Country Status (8)
| Country | Link |
|---|---|
| AT (1) | AT284452B (forum.php) |
| BE (1) | BE712904A (forum.php) |
| CH (1) | CH503094A (forum.php) |
| DE (1) | DE1770073A1 (forum.php) |
| ES (1) | ES352181A1 (forum.php) |
| GB (1) | GB1158536A (forum.php) |
| NL (1) | NL6704630A (forum.php) |
| SE (1) | SE347280B (forum.php) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1155595A (en) * | 1979-08-27 | 1983-10-18 | Hugh C. Gardner | Composition containing a half ester of an organic polyol, an unsaturated monomer, and epoxide and a basic compound |
| CA1147086A (en) * | 1979-08-27 | 1983-05-24 | Union Carbide Corporation | Composition containing a half ester of an organic polyol, an unsaturated monomer, an epoxide, and reinforcing fiber |
| DE3020524C2 (de) * | 1980-05-30 | 1983-10-27 | Hoechst Ag, 6230 Frankfurt | Verfahren zur Herstellung von härtbaren Copolymeren |
| DE3031655A1 (de) * | 1980-08-22 | 1982-04-08 | Hoechst Ag, 6000 Frankfurt | Verfahren zur herstellung von haertbaren copolymeren |
| AU7930598A (en) * | 1998-06-12 | 1999-12-30 | Compagnia Commerciale Italiana S.R.L. | Anionic agent for paper surface sizing |
-
1967
- 1967-03-31 NL NL6704630A patent/NL6704630A/xx unknown
-
1968
- 1968-03-25 SE SE03957/68A patent/SE347280B/xx unknown
- 1968-03-26 CH CH442768A patent/CH503094A/de not_active IP Right Cessation
- 1968-03-28 BE BE712904D patent/BE712904A/xx unknown
- 1968-03-28 DE DE19681770073 patent/DE1770073A1/de active Pending
- 1968-03-29 ES ES352181A patent/ES352181A1/es not_active Expired
- 1968-03-29 AT AT307568A patent/AT284452B/de not_active IP Right Cessation
- 1968-04-01 GB GB15659/68A patent/GB1158536A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ES352181A1 (es) | 1970-02-01 |
| SE347280B (forum.php) | 1972-07-31 |
| GB1158536A (en) | 1969-07-16 |
| BE712904A (forum.php) | 1968-07-31 |
| NL6704630A (forum.php) | 1968-10-01 |
| AT284452B (de) | 1970-09-10 |
| DE1770073A1 (de) | 1971-09-23 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1720505A1 (de) | Modifiziertes Polyalkoxysilan enthaltende harzartige Masse und Verfahren zu ihrer Herstellung | |
| DE2129994A1 (de) | Condensationspolymere | |
| DE2112718B2 (de) | Durch katalysatorzusatz haertbare ueberzugsmassen | |
| DE2907997C2 (de) | Verfahren zur Herstellung von härtbaren Copolymeren | |
| DE1595243C3 (de) | Verfahren zum Herstellen von Lösungen neuer Mischpolymerisate | |
| CH503094A (de) | Verfahren zur Herstellung eines verbesserten Harzbindemittels für Einbrennlacke | |
| DE2633267C3 (de) | Mit Polyester modifiziertes Vinylpolymeres, Verfahren zu seiner Herstellung und Verwendung | |
| DE2552634C3 (de) | Verfahren zur Herstellung von Malein- oder Fumarsäureestern | |
| DE1922942C3 (de) | Verwendung eines linearen, wärmehärtbaren Copolymerisats zur Oberflächenvergütung von Holzwerkstoffplatten | |
| DE3219471C2 (forum.php) | ||
| DE2302842C3 (de) | Formmassen auf Basis ungesättigter Polyester, anpolymerisierbarer Vinylmonomerer und Celluloseester | |
| DE1520834A1 (de) | Verfahren zur Herstellung von Harzstoffen | |
| DE1645548A1 (de) | UEberzugsgemische und Verfahren zu deren Herstellung | |
| DE1233605C2 (de) | Verfahren zum herstellen von copolymerisaten | |
| DE2116511A1 (en) | Resinous condensates - suitable for use as sealing, coating and moulding cpds, laminating and casting resins and adhesives | |
| DE2851614C2 (de) | Verfahren zur Herstellung von in organischen Lösungsmitteln löslichen hydroxylgruppentragenden Copolymerisaten | |
| DE1420309A1 (de) | Mischpolyester | |
| DE1645200C3 (de) | Verfahren zur Herstellung von löslichen Copolymerisaten | |
| DE910124C (de) | Verfahren zur Herstellung von Mischpolymerisaten | |
| EP0003315B1 (de) | Verwendung reaktiver Oligomerer zur Härtung ungesättigter Polyesterharze | |
| CH457859A (de) | Verfahren zur Herstellung von Copolymerisaten und deren Verwendung | |
| DE1105160B (de) | Verfahren zur Herstellung von Polymerisationsprodukten durch Auspolymerisieren ungesaettigter Polyesterharze | |
| DE2848262C2 (de) | Verfahren zur Herstellung von nach Neutralisation wasserlöslichen Copolymerisaten | |
| DE1645440C3 (de) | Neue härtbare ungesättigte PoIyesteramidharzmassen | |
| AT300153B (de) | Verfahren zur herstellung wasserverduennbarer, insbesondere fuer die elektrophoretische ueberzugsbildung geeigneter einbrennlacke |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |