GB835588A - Improvements in the production of condensation products - Google Patents
Improvements in the production of condensation productsInfo
- Publication number
- GB835588A GB835588A GB668657A GB668657A GB835588A GB 835588 A GB835588 A GB 835588A GB 668657 A GB668657 A GB 668657A GB 668657 A GB668657 A GB 668657A GB 835588 A GB835588 A GB 835588A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alcohol
- vinyl
- acids
- esters
- solvents
- 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
- 239000007859 condensation product Substances 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 6
- 239000002904 solvent Substances 0.000 abstract 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 abstract 3
- -1 crotonamide Chemical compound 0.000 abstract 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 abstract 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 abstract 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 abstract 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 abstract 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 abstract 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 abstract 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 150000001408 amides Chemical class 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 238000009833 condensation Methods 0.000 abstract 2
- 230000005494 condensation Effects 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 238000006266 etherification reaction Methods 0.000 abstract 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 abstract 2
- 229930195733 hydrocarbon Natural products 0.000 abstract 2
- 150000002430 hydrocarbons Chemical class 0.000 abstract 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 abstract 2
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 abstract 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract 2
- BSSNZUFKXJJCBG-OWOJBTEDSA-N (e)-but-2-enediamide Chemical compound NC(=O)\C=C\C(N)=O BSSNZUFKXJJCBG-OWOJBTEDSA-N 0.000 abstract 1
- BSSNZUFKXJJCBG-UPHRSURJSA-N (z)-but-2-enediamide Chemical compound NC(=O)\C=C/C(N)=O BSSNZUFKXJJCBG-UPHRSURJSA-N 0.000 abstract 1
- 150000000211 1-dodecanols Chemical class 0.000 abstract 1
- OZFIGURLAJSLIR-UHFFFAOYSA-N 1-ethenyl-2h-pyridine Chemical compound C=CN1CC=CC=C1 OZFIGURLAJSLIR-UHFFFAOYSA-N 0.000 abstract 1
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 abstract 1
- LPNSCOVIJFIXTJ-UHFFFAOYSA-N 2-methylidenebutanamide Chemical compound CCC(=C)C(N)=O LPNSCOVIJFIXTJ-UHFFFAOYSA-N 0.000 abstract 1
- MQWCXKGKQLNYQG-UHFFFAOYSA-N 4-methylcyclohexan-1-ol Chemical compound CC1CCC(O)CC1 MQWCXKGKQLNYQG-UHFFFAOYSA-N 0.000 abstract 1
- QDTDKYHPHANITQ-UHFFFAOYSA-N 7-methyloctan-1-ol Chemical compound CC(C)CCCCCCO QDTDKYHPHANITQ-UHFFFAOYSA-N 0.000 abstract 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 abstract 1
- 239000004439 Isononyl alcohol Substances 0.000 abstract 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 abstract 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical class O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 abstract 1
- 239000004952 Polyamide Substances 0.000 abstract 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 abstract 1
- 239000000853 adhesive Substances 0.000 abstract 1
- 230000001070 adhesive effect Effects 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 abstract 1
- 239000002585 base Substances 0.000 abstract 1
- 235000019445 benzyl alcohol Nutrition 0.000 abstract 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 abstract 1
- 239000004327 boric acid Substances 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- 239000001913 cellulose Substances 0.000 abstract 1
- 229920002678 cellulose Polymers 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 239000008199 coating composition Substances 0.000 abstract 1
- 229920001577 copolymer Polymers 0.000 abstract 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 abstract 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 239000010408 film Substances 0.000 abstract 1
- 235000019253 formic acid Nutrition 0.000 abstract 1
- 150000004674 formic acids Chemical class 0.000 abstract 1
- 235000011087 fumaric acid Nutrition 0.000 abstract 1
- 150000002238 fumaric acids Chemical class 0.000 abstract 1
- 235000011187 glycerol Nutrition 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 239000004922 lacquer Substances 0.000 abstract 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 abstract 1
- 239000011976 maleic acid Substances 0.000 abstract 1
- 150000002689 maleic acids Chemical class 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 abstract 1
- 125000005395 methacrylic acid group Chemical group 0.000 abstract 1
- KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical compound C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 abstract 1
- 150000003016 phosphoric acids Chemical class 0.000 abstract 1
- 150000003022 phthalic acids Chemical class 0.000 abstract 1
- 239000000049 pigment Substances 0.000 abstract 1
- 229920002647 polyamide Polymers 0.000 abstract 1
- 238000006116 polymerization reaction Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 abstract 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 abstract 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 abstract 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 1
- 229920001567 vinyl ester resin Polymers 0.000 abstract 1
- 229920002554 vinyl polymer Polymers 0.000 abstract 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
- C08F8/00—Chemical modification by after-treatment
Landscapes
- Chemical & Material Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Phenolic Resins Or Amino Resins (AREA)
Abstract
A copolymer of a primary ethylenicallyunsaturated carboxylic acid amide and another ethylenically-unsaturated compound is condensed with formaldehyde and etherified with a monohydric alcohol free from aliphatic unsaturation in the presence of an etherification catalyst, the alcohol also acting as solvent. Specified amides are acrylamide, methacrylamide, alpha - ethylacrylamide, crotonamide, fumaric acid diamide and maleic acid diamide. They may be copolymerized with, for example, butadiene, isoprene, isobutylene, styrene and its alkyl derivatives, acrylic, methacrylic, alpha-ethacrylic, crotonic, maleic and fumaric acids and their esters, vinyl esters, N-substituted acrylamides and methacrylamides, vinyl and vinylidene halides, and N-vinylcarbazole, N-vinyl pyridine and N-vinyl pyrrolidone. Mixtures of more than one amide and more than one copolymerizable compound may be used. Examples of etherifying alcohols are ethanol, n-propanol, n- and iso-butanol, amyll alcohol, hexanol, octanol, 2-ethylhexanol, iso-nonyl-alcohol, decyl and lauryl alcohols, cyclohexanol, methylcyclohexanol and benzyl alcohol. They are preferably used in admixture with inert solvents such as aliphatic and aromatic hydrocarbons. The alcohol may also have been used as solvent in the initial polymerization and in the condensation with formaldehyde. Other solvents may however be used for the latter condensation, e.g. hydrocarbons, esters and ketones. Suitable etherification catalysts are those which can produce a pH of about 2.5 to 4.5, 3.g. hydrochloric, phosphoric, phthalic and formic acids, a mixture of glycerine and boric acid and salts of strong acids with weak bases. They may be neutralized after the reaction by the addition of alkali. The products may be mixed with other solvents (such as hydrocarbons), pigments, alkyl-, urea-, melamine-, phenol- and urethane resins, polyamides and cellulose derivatives, to form lacquers, films, adhesives, impregnants and coating compositions for a variety of materials. Hardening agents may be added, e.g. maleic acid, p-toluene sulphonic acid and its chloride, hydrochloric and nitric acids and ammonium nitrate. Specification 467,492 is referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB39338A DE1054710B (en) | 1956-03-01 | 1956-03-01 | Process for the production of etherified condensation products |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB835588A true GB835588A (en) | 1960-05-25 |
Family
ID=6965777
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB668657A Expired GB835588A (en) | 1956-03-01 | 1957-02-28 | Improvements in the production of condensation products |
Country Status (3)
| Country | Link |
|---|---|
| DE (1) | DE1054710B (en) |
| FR (1) | FR1173990A (en) |
| GB (1) | GB835588A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3255139A (en) * | 1962-03-21 | 1966-06-07 | Bayer Ag | Preparation of n-(alkenyloxymethylene) acrylamide copolymers and products thereof |
| US7381472B2 (en) | 2002-08-15 | 2008-06-03 | Valspar Sourcing, Inc. | Durable polyester coating |
| US8758888B2 (en) | 2007-04-27 | 2014-06-24 | Valspar Sourcing, Inc. | Crosslinkable imide polyester coating |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE733317C (en) * | 1935-10-29 | 1943-03-24 | Roehm & Haas G M B H | Process for the production of synthetic resins from methacrylic acid amide |
| GB467402A (en) * | 1935-11-11 | 1937-06-11 | Roehm & Haas Ag | Improvements in or relating to the manufacture and use of interpolymers of methacrylic acid amide |
-
1956
- 1956-03-01 DE DEB39338A patent/DE1054710B/en active Pending
-
1957
- 1957-02-28 GB GB668657A patent/GB835588A/en not_active Expired
- 1957-02-28 FR FR1173990D patent/FR1173990A/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3255139A (en) * | 1962-03-21 | 1966-06-07 | Bayer Ag | Preparation of n-(alkenyloxymethylene) acrylamide copolymers and products thereof |
| US7381472B2 (en) | 2002-08-15 | 2008-06-03 | Valspar Sourcing, Inc. | Durable polyester coating |
| US8124242B2 (en) | 2002-08-15 | 2012-02-28 | Valspar Sourcing, Inc. | Durable polyester coating |
| US8758888B2 (en) | 2007-04-27 | 2014-06-24 | Valspar Sourcing, Inc. | Crosslinkable imide polyester coating |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1054710B (en) | 1959-04-09 |
| FR1173990A (en) | 1959-03-04 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2758379B2 (en) | Solution polymerization of vinyl monomers | |
| US4243797A (en) | Process for the manufacture of soft and hard resins of urea, formaldehyde and a CH-acidic aldehyde, and their use | |
| GB949404A (en) | Coloured crosslinkable and crosslinked copolymers | |
| US3567678A (en) | Polymers and hair coloring and compositions comprising the same | |
| GB1271743A (en) | Thermosetting resin of polyamide and copolymer of unsaturated dicarboxylic acid or derivative and an olefin or unsaturated ether or ester | |
| GB1530022A (en) | Aqueous coating agents | |
| GB727414A (en) | Improvements in or relating to the production of moistureproof sheet wrapping materials | |
| GB835588A (en) | Improvements in the production of condensation products | |
| US2138031A (en) | Amino alcohol acrylates | |
| US3959224A (en) | Water-soluble hydroxyalkylated and alkoxyalkylated compositions and the like derived from N-3-oxohydrocarbon-substituted acrylamides, and polymers thereof | |
| US3280189A (en) | Preparation of alcohol blocked n-hydroxymethyl unsaturated acid amides | |
| US3728377A (en) | 4,4-bis(alkoxycarbonyl)benzoin ethers | |
| GB1153207A (en) | Process for producing Cationic Carbamoyl Polymers | |
| US2255229A (en) | Solvent for organic film-forming materials | |
| US3795648A (en) | Surfactant-free ampholytic polymeric latices | |
| US2541975A (en) | Coating compositions flatted with silica aerogel | |
| US3776976A (en) | Process for the production of polymers containing n-substituted acrylic acid amides and/or methacrylic acid amides | |
| US3340221A (en) | Polymers containing ethylenically unsaturated derivatives of orthohydroxy aromatics as reactive dye sites | |
| US2397548A (en) | Resinous condensation products | |
| Corbett et al. | The Cross‐linking of Cellulose and its Derivatives: I—The Use of Unsaturated Esters in Cross‐linking Reactions | |
| US2345427A (en) | Solvent for organic film-forming materials | |
| GB918050A (en) | Improvements in and relating to anchoring surface coatings to cellulosic surfaces | |
| US2767154A (en) | Method of producing pigmented lacquers and the like | |
| US3597381A (en) | Color stabilized aqueous dispersions of iminated vinyl addition polymers and process for preparing same | |
| US2378015A (en) | Polyvinyl ethers of beta guanylethanols |