DE1745540C3 - Verfahren zur Herstellung von selbstvernetzenden Copolymerisaten - Google Patents
Verfahren zur Herstellung von selbstvernetzenden CopolymerisatenInfo
- Publication number
- DE1745540C3 DE1745540C3 DE1745540A DE1745540A DE1745540C3 DE 1745540 C3 DE1745540 C3 DE 1745540C3 DE 1745540 A DE1745540 A DE 1745540A DE 1745540 A DE1745540 A DE 1745540A DE 1745540 C3 DE1745540 C3 DE 1745540C3
- Authority
- DE
- Germany
- Prior art keywords
- acid
- parts
- hydrogen atom
- reaction
- group
- 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
- 238000000034 method Methods 0.000 title claims description 10
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- 229920001577 copolymer Polymers 0.000 title claims description 6
- 238000004132 cross linking Methods 0.000 title claims description 6
- 239000003054 catalyst Substances 0.000 claims description 23
- 238000006243 chemical reaction Methods 0.000 claims description 22
- 239000007795 chemical reaction product Substances 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 19
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 18
- 238000006116 polymerization reaction Methods 0.000 claims description 16
- 229920005989 resin Polymers 0.000 claims description 15
- 239000011347 resin Substances 0.000 claims description 15
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 13
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 claims description 12
- 229910052901 montmorillonite Inorganic materials 0.000 claims description 11
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 10
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 10
- 239000011976 maleic acid Substances 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 9
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 8
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 6
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 6
- -1 fatty acid esters Chemical class 0.000 claims description 6
- 229920000877 Melamine resin Polymers 0.000 claims description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 5
- 238000007334 copolymerization reaction Methods 0.000 claims description 4
- 239000000047 product Substances 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 239000012084 conversion product Substances 0.000 claims description 3
- 239000001530 fumaric acid Substances 0.000 claims description 3
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical group NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 claims description 3
- 239000000178 monomer Substances 0.000 claims description 3
- 229920000180 alkyd Polymers 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000004922 lacquer Substances 0.000 claims description 2
- 125000005395 methacrylic acid group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 12
- 125000004432 carbon atom Chemical group C* 0.000 claims 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 235000014113 dietary fatty acids Nutrition 0.000 claims 2
- 239000000194 fatty acid Substances 0.000 claims 2
- 229930195729 fatty acid Natural products 0.000 claims 2
- JWPVCFSBPUPIQA-WAYWQWQTSA-N (z)-2-butylbut-2-enedioic acid Chemical compound CCCC\C(C(O)=O)=C\C(O)=O JWPVCFSBPUPIQA-WAYWQWQTSA-N 0.000 claims 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 238000005266 casting Methods 0.000 claims 1
- QZSKYMMIFBLVGO-UHFFFAOYSA-N ethane-1,2-diol;2-methylprop-2-enoic acid Chemical class OCCO.CC(=C)C(O)=O QZSKYMMIFBLVGO-UHFFFAOYSA-N 0.000 claims 1
- 125000004494 ethyl ester group Chemical group 0.000 claims 1
- 150000004665 fatty acids Chemical class 0.000 claims 1
- 239000003337 fertilizer Substances 0.000 claims 1
- 239000000499 gel Substances 0.000 claims 1
- 239000003456 ion exchange resin Substances 0.000 claims 1
- 229920003303 ion-exchange polymer Polymers 0.000 claims 1
- 150000007974 melamines Chemical class 0.000 claims 1
- 239000003973 paint Substances 0.000 claims 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 claims 1
- 229920000728 polyester Polymers 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 57
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 18
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 18
- 239000008096 xylene Substances 0.000 description 15
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000009833 condensation Methods 0.000 description 9
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 230000005494 condensation Effects 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- BNCADMBVWNPPIZ-UHFFFAOYSA-N 2-n,2-n,4-n,4-n,6-n,6-n-hexakis(methoxymethyl)-1,3,5-triazine-2,4,6-triamine Chemical compound COCN(COC)C1=NC(N(COC)COC)=NC(N(COC)COC)=N1 BNCADMBVWNPPIZ-UHFFFAOYSA-N 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 239000004640 Melamine resin Substances 0.000 description 3
- 150000001768 cations Chemical class 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- YAJYJWXEWKRTPO-UHFFFAOYSA-N 2,3,3,4,4,5-hexamethylhexane-2-thiol Chemical compound CC(C)C(C)(C)C(C)(C)C(C)(C)S YAJYJWXEWKRTPO-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 229910010413 TiO 2 Inorganic materials 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 238000010526 radical polymerization reaction Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 240000001624 Espostoa lanata Species 0.000 description 1
- 235000009161 Espostoa lanata Nutrition 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- 238000006424 Flood reaction Methods 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 150000007513 acids Chemical class 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
- 238000009835 boiling Methods 0.000 description 1
- UTOVMEACOLCUCK-PLNGDYQASA-N butyl maleate Chemical compound CCCCOC(=O)\C=C/C(O)=O UTOVMEACOLCUCK-PLNGDYQASA-N 0.000 description 1
- QHIWVLPBUQWDMQ-UHFFFAOYSA-N butyl prop-2-enoate;methyl 2-methylprop-2-enoate;prop-2-enoic acid Chemical compound OC(=O)C=C.COC(=O)C(C)=C.CCCCOC(=O)C=C QHIWVLPBUQWDMQ-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- GPKFMIVTEHMOBH-UHFFFAOYSA-N cumene;hydrate Chemical compound O.CC(C)C1=CC=CC=C1 GPKFMIVTEHMOBH-UHFFFAOYSA-N 0.000 description 1
- 101150038956 cup-4 gene Proteins 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000004870 electrical engineering Methods 0.000 description 1
- 238000004070 electrodeposition Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000011521 glass Substances 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
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 230000019612 pigmentation Effects 0.000 description 1
- 238000011085 pressure filtration Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 238000003746 solid phase reaction Methods 0.000 description 1
- 238000010671 solid-state reaction Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
Classifications
-
- 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
- C08F22/00—Homopolymers and 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
- C08F22/10—Esters
- C08F22/12—Esters of phenols or saturated alcohols
- C08F22/22—Esters containing nitrogen
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S525/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S525/923—Aminoplast having terminal ethylenic unsaturation
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)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT712566A AT271880B (de) | 1966-07-26 | 1966-07-26 | Verfahren zur Herstellung von selbstvernetzenden Polymerisaten |
| AT169167A AT279162B (de) | 1967-02-21 | 1967-02-21 | Verfahren zur Herstellung von selbstvernetzenden Polymerisaten |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1745540A1 DE1745540A1 (de) | 1972-02-10 |
| DE1745540B2 DE1745540B2 (de) | 1974-08-29 |
| DE1745540C3 true DE1745540C3 (de) | 1975-04-30 |
Family
ID=25596547
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1745540A Expired DE1745540C3 (de) | 1966-07-26 | 1967-06-19 | Verfahren zur Herstellung von selbstvernetzenden Copolymerisaten |
| DE19671795704 Granted DE1795704B2 (de) | 1966-07-26 | 1967-07-19 | Verfahren zur herstellung von copolymerisierbaren umsetzungsprodukten von polymethylolmelaminen mit acryl-, methacryl-, malein- und fumarsaeure-derivaten |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19671795704 Granted DE1795704B2 (de) | 1966-07-26 | 1967-07-19 | Verfahren zur herstellung von copolymerisierbaren umsetzungsprodukten von polymethylolmelaminen mit acryl-, methacryl-, malein- und fumarsaeure-derivaten |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3539661A (enExample) |
| BE (1) | BE701817A (enExample) |
| CH (2) | CH532617A (enExample) |
| DE (2) | DE1745540C3 (enExample) |
| GB (2) | GB1116858A (enExample) |
| GR (1) | GR33980B (enExample) |
| NL (1) | NL6709562A (enExample) |
| SE (1) | SE337115B (enExample) |
| SU (1) | SU366618A3 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0006206B1 (en) * | 1978-06-21 | 1982-11-24 | Teijin Limited | Melamine group-containing acrylates and/or methacrylates, polymerizable and curable composition thereof, molded article made of the polymerized and cured composition and resin molded article coated with the composition |
| US4847336A (en) * | 1988-04-28 | 1989-07-11 | Ulano Corporation | Process for the preparation of acryloyloxyethoxymethyl-melamines |
| DE4020766A1 (de) * | 1990-06-29 | 1992-01-02 | Basf Ag | Strahlenhaertbare bindemittel |
| GB2267502B (en) * | 1992-05-28 | 1997-01-22 | Aligena Ag | Polymeric reaction products for use in immobilized buffered gels and membranes |
| AU2001217737A1 (en) * | 2000-07-07 | 2002-01-21 | 3M Innovative Properties Company | Polymer compositions with energetically degradable crosslinker |
| US8455574B2 (en) * | 2004-02-19 | 2013-06-04 | E I Du Pont De Nemours And Company | Composite compositions comprising cellulose and polymeric components |
| DE102008038943A1 (de) | 2008-08-11 | 2010-02-18 | Borealis Agrolinz Melamine Gmbh | Vernetzbare Acrylatharze |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB628150A (en) * | 1947-02-10 | 1949-08-23 | Roy Hammond | New polymerisable materials and polymers thereof |
| US3020255A (en) * | 1959-09-14 | 1962-02-06 | American Cyanamid Co | Unsaturated ether of methylol melamine, and polymers and copolymers thereof |
| GB1007588A (en) * | 1963-09-18 | 1965-10-13 | Alma Guard Ltd | Aminoplast composition and production thereof |
| US3396209A (en) * | 1965-09-28 | 1968-08-06 | Desoto Inc | Air drying ethers of monohydric polyallyl ethers and copolymer containing alkoxyalkylted aminotriazine transesters |
-
1966
- 1966-11-07 GB GB49826/66A patent/GB1116858A/en not_active Expired
-
1967
- 1967-06-16 CH CH858567A patent/CH532617A/de not_active IP Right Cessation
- 1967-06-16 CH CH1375570A patent/CH532619A/de not_active IP Right Cessation
- 1967-06-19 DE DE1745540A patent/DE1745540C3/de not_active Expired
- 1967-06-30 SE SE10008/67*A patent/SE337115B/xx unknown
- 1967-07-10 GR GR670133980A patent/GR33980B/el unknown
- 1967-07-10 NL NL6709562A patent/NL6709562A/xx unknown
- 1967-07-19 DE DE19671795704 patent/DE1795704B2/de active Granted
- 1967-07-21 US US654949A patent/US3539661A/en not_active Expired - Lifetime
- 1967-07-25 BE BE701817D patent/BE701817A/xx unknown
- 1967-07-26 SU SU1175321A patent/SU366618A3/ru active
- 1967-11-07 GB GB50573/67A patent/GB1212001A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| US3539661A (en) | 1970-11-10 |
| CH532617A (de) | 1973-01-15 |
| GB1116858A (en) | 1968-06-12 |
| NL6709562A (enExample) | 1968-01-29 |
| BE701817A (enExample) | 1968-01-02 |
| GR33980B (el) | 1968-02-29 |
| DE1745540A1 (de) | 1972-02-10 |
| DE1795704A1 (de) | 1973-11-22 |
| CH532619A (de) | 1973-01-15 |
| SU366618A3 (enExample) | 1973-01-16 |
| GB1212001A (en) | 1970-11-11 |
| DE1795704C3 (enExample) | 1978-05-24 |
| SE337115B (enExample) | 1971-07-26 |
| DE1745540B2 (de) | 1974-08-29 |
| DE1795704B2 (de) | 1977-09-22 |
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