USRE20383E - Film forming compositions and proc - Google Patents
Film forming compositions and proc Download PDFInfo
- Publication number
- USRE20383E USRE20383E US20383DE USRE20383E US RE20383 E USRE20383 E US RE20383E US 20383D E US20383D E US 20383DE US RE20383 E USRE20383 E US RE20383E
- Authority
- US
- United States
- Prior art keywords
- reaction
- colloid
- urea
- formaldehyde
- mixture
- 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
- 239000000203 mixture Substances 0.000 title description 14
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 20
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 20
- 239000000084 colloidal system Substances 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 17
- 239000000243 solution Substances 0.000 description 17
- 238000010438 heat treatment Methods 0.000 description 11
- 239000004202 carbamide Substances 0.000 description 10
- 239000004922 lacquer Substances 0.000 description 10
- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 238000009835 boiling Methods 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 238000000034 method Methods 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000007859 condensation product Substances 0.000 description 6
- 239000000839 emulsion Substances 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- ODGAOXROABLFNM-UHFFFAOYSA-N Polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 description 4
- 229920001807 Urea-formaldehyde Polymers 0.000 description 4
- 239000003125 aqueous solvent Substances 0.000 description 4
- -1 hydrogen ions Chemical class 0.000 description 4
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000005496 tempering Methods 0.000 description 4
- 238000005336 cracking Methods 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 239000004902 Softening Agent Substances 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000000977 initiatory Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- SSZWWUDQMAHNAQ-UHFFFAOYSA-N 3-MCPD Chemical compound OCC(O)CCl SSZWWUDQMAHNAQ-UHFFFAOYSA-N 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N Boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N carbodiimide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000011356 non-aqueous organic solvent Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000002035 prolonged Effects 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
- C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
- C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
- C08G12/04—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds
- C08G12/10—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds with acyclic compounds having the moiety X=C(—N<)2 in which X is O, S or —N
- C08G12/12—Ureas; Thioureas
Definitions
- the present application is a division of my colng urea are mixed with 100 parts by weight of pending application Serial No. 700,736, filed a 30% aqueous solution of formaldehyde which March 20, 1924, Patent No. 1,687,312, dated not. is free from acid or is neutralized or is slightly 9. 1928, for a process for manufacturing such alkaline, the mixture being heated to boiling in novel water clear urea-formaldehyde condensabDllcr With a reflux condenser. After short 10 tion products.
- the present invention relates to the f in a little water, are added thereto; the whole ture of non-aqueous lacquers from h novel mixture is thereafter further boiled in the boiler condensation products, namely, the products obwith the reflux condenserf 6 hours After t m by conducmngthe first, stage of the being allowed to stand 1n the cold for several ti between urea and formaldehyde wherein hours, the mass is found to be divided in two the viscous initial products are formed in two layel'slof which the pp One is pcu cdcfi,whcrcessential phases, the first in the absence of free after the tough forming the lower ayer is hydrogen ions and the second in the presence of repeatedly washed with W
- the gel thus P fr e hydrogen ions, This is accomplished by prised can be dissolved in non-aqueous solvents, adjusting the o in the fi t phase, which is such as for instance epic
- this lacquer solution yields a time to a value f about -1 or below, and by non-cracking coating of lacquer, which is comadjusting the Ch in the second phase to a value P186813 insensitive to any action of waterupwards of 10- but not reaching 10-, and con- I la1m tinuing the reaction is continued by further heat-
- the symbol c represents usually grammes lutions which consists in reacting on a urea with of hydrogen ions per liter, a solution of formaldehyde by boiling the mixture
- the hydrogen ion concentration may also be adiusted to a Ch not exceeding 10 for a short time, thereafter adjusting the hydrogen ion conexpressed by the Symbol pH (chosen by Soren centration of the reaction mixture to a value sen) representing-log H.
- Ch of 10- to cause complete conversion of the first formed hydrophile emulsion colloid in a hydrophobe colloid on further heating, continuing the readzion by further heating the reaction mixture, cooling the reaction product whereat the hydrophobe colloid is precipitated therefrom, separating the precipitated colloid from the water, dissolving it in nonaqueous solvents and adding tempering agents, having the property of preventing the films formed by evaporation of the solutions from cracking.
- a composition comprising a solution of a urea-formaldehyde condensation product in a non-aqueous solvent, said solution containing a tempering agent.
- a non-aqueous lacquer solution containing a urea-formaldehyde condensation product 7.
- a non-aqueous lacquer solution containing a ureasformaldehyde condensation product and a softening agent containing a ureasformaldehyde condensation product and a softening agent.
- Acomposition comprising a urea-formaldehyde condensation product and chlorhydrin.
- a lacquer composition comprising a. hydrophobe reaction product of urea and formaldehyde, soluble and dissolved in a non-aqueous solvent. soluble and dissolved in a non-aqueous organic solvent.
Description
Reissued May 25, 1937 Re,
UNITED STATES PATENT OFFICE FILM FORMING COMPOSITIONS AND PROC- ESS FOR MANUFACTURING SAME Kurt Ripper, Berlin, Germany, assignor, by mesne assignments, to American Cyanamid Company, a corporation of Maine No Drawing. Original application March 20, 1924, Serial No. 700,736. Patent No. 1,734,693, dated November 5, 1929. Divided and application June 22, 1925, Serial No. 38,920. Application for reissue November 4, 1931, Serial No. 573,033. In Austria March 31, 1923 10 Claims. (01. 134-26) This invention relates to the manufacture of such additions have the disadvantage of easily lacquers, films and the like from certain novel cracking in the warmth.
condensation products of urea or its derivatives Example with formaldehyde, and to lacquer compositions thus prepared. 30 parts by weight of pure and neutrally react- 5 The present application is a division of my colng urea are mixed with 100 parts by weight of pending application Serial No. 700,736, filed a 30% aqueous solution of formaldehyde which March 20, 1924, Patent No. 1,687,312, dated not. is free from acid or is neutralized or is slightly 9. 1928, for a process for manufacturing such alkaline, the mixture being heated to boiling in novel water clear urea-formaldehyde condensabDllcr With a reflux condenser. After short 10 tion products. boiling 5 parts by weight of boric acid, dissolved The present invention relates to the f in a little water, are added thereto; the whole ture of non-aqueous lacquers from h novel mixture is thereafter further boiled in the boiler condensation products, namely, the products obwith the reflux condenserf 6 hours After t m by conducmngthe first, stage of the being allowed to stand 1n the cold for several ti between urea and formaldehyde wherein hours, the mass is found to be divided in two the viscous initial products are formed in two layel'slof which the pp One is pcu cdcfi,whcrcessential phases, the first in the absence of free after the tough forming the lower ayer is hydrogen ions and the second in the presence of repeatedly washed with W The gel thus P fr e hydrogen ions, This is accomplished by duced can be dissolved in non-aqueous solvents, adjusting the o in the fi t phase, which is such as for instance epichlorhydrin. Mixed with plated after applying heat'for a short period f softening agents this lacquer solution yields a time to a value f about -1 or below, and by non-cracking coating of lacquer, which is comadjusting the Ch in the second phase to a value P186813 insensitive to any action of waterupwards of 10- but not reaching 10-, and con- I la1m tinuing the reaction is continued by further heat- The process of producmg film'formjng in; The symbol c represents usually grammes lutions which consists in reacting on a urea with of hydrogen ions per liter, a solution of formaldehyde by boiling the mixture The hydrogen ion concentration may also be adiusted to a Ch not exceeding 10 for a short time, thereafter adjusting the hydrogen ion conexpressed by the Symbol pH (chosen by Soren centration of the reaction mixture to a value sen) representing-log H. Therefore the value upwards of a Ch of 104 to cause complete com Ch=m 7 f ff g the valge pHzq' the version of the first formed hydrophile emulsion value Ch: to t 8 pH: colloid in a hydrophobe colloid on further heating. This mode condltctmg the polymerization continuing the reaction by heating the reaction Process in an and medmm results in the forma' mixture cooling the reaction product whereby tion of a hydrophobe emulsion colloid which had the hymphobe colloid is precipitated there been unknown heretofore. If the condensation from separating the precipitated m from Product formed by Short heating of the mixture the water and dissolving it in a non-aqueous solof urea and formaldehyde is heated for prolonged vent time or if the concentration of the hydrogen ions 2. Th process of producing film-forming soluis increased above accrta im t, ydrop tions which consists in reacting on a urea with m l ion coll id is precip y cooline'the a solution of formaldehyde free of acid, initiatreaction mass after accomplishme t o the p ing the reaction by boiling the mixture for a mcrlzatlcn D short time, thereafter adjusting the hydrogen 4 I have fOlmC that the Y D gel thus P ion concentration of the reaction mixture to a duced is far more suitable than any other reacvalue upwards of Ch of 10-1 by addition f acidt o Product Of this d for manufacturing reacting agents to cause complete conversion of q s or fil an h the said hy r ph the first formed hydrophile emulsion colloid in 5 product may be used with non-aqueous solvents hydrophgbe ll id n further heating, nand n-aq us p in a ts t make tinuing the reaction by heating the, reaction mixquers, even when such solvents are not miscible t cooling th ot product whereby the with water. This result is of importance, because hydrophobe colloid is precipitated, separating there are no tempering agents for lacquers 501- the precipitated colloid from the water and disuble in water, and because lacquers made without solving it in a nonaqueous solvent. 5
3. The process of producing film-forming solutions which consists in reacting on a urea with a solution of formaldehyde, the free formic acid content of which solution had been eliminated beiore starting the reaction. initiating the reaction by boiling the mixture for a short time, adlusting the hydrogen ion concentration in the reaction mixture by addition of acid-reacting agents to a value upwards ci-a. Ch of to cause complete conversion of the first formed hydrophile emulsion colloid in a hydrophobe colloid on further heating. continuing the reaction by heating the reaction mixture, cooling the reaction product whereby the hydrophcbe colloid is precipitated therefrom, separating the precipitated colloid from the water, and dissolving it in a nonaqueous solvent.
4. The process of producing film-forming solutions which consists in reacting on a urea with a solution of formaldehyde. the free formic acid content of which solution has been neutralized before starting the reaction-initiating the reaction by boiling the mixture for a short time, adjusting the hydrogen ion concentration of the reaction mixture to a value upwards of a Ch of 10- to cause complete conversion of the iirst formed hydrophile emulsion colloid in a hydrophobe coiloid on'further heating. continuing the reaction by heating the reaction mixture, cooling the reaction product whereby the hydrophobe colloid is precipitated therefrom, separating the precipitated colloid from the water, dissolving it in a nonaqueous solvent and adding a tempering agent.
5. The process of producing film-forming solutions which consists in reacting on a urea with a solution of formaldehyde, the tree formic acid content of which solution had been neutralized before starting the reaction, initiating the reaction by'boiling the mixture for a short time, adiusting the hyr'rogen ion concentration in the reaction mixture to a value upwards of a. Ch of 10- to cause complete conversion of the first formed hydrophile emulsion colloid in a hydrophobe colloid on further heating, continuing the readzion by further heating the reaction mixture, cooling the reaction product whereat the hydrophobe colloid is precipitated therefrom, separating the precipitated colloid from the water, dissolving it in nonaqueous solvents and adding tempering agents, having the property of preventing the films formed by evaporation of the solutions from cracking.
6. A composition comprising a solution of a urea-formaldehyde condensation product in a non-aqueous solvent, said solution containing a tempering agent.
7. A non-aqueous lacquer solution containing a urea-formaldehyde condensation product.
8. A non-aqueous lacquer solution containing a ureasformaldehyde condensation product and a softening agent.
' 9. Acomposition comprising a urea-formaldehyde condensation product and chlorhydrin.
10. A lacquer composition comprising a. hydrophobe reaction product of urea and formaldehyde, soluble and dissolved in a non-aqueous solvent. soluble and dissolved in a non-aqueous organic solvent.
KURT RIPPER CERTIFICATE OF CORRECTION.
Reissue No. 20,383. May 25, 1937.
KURT RIPPER.
It is hereby certified that error appears in the printed specification of the above numbered patent requiring correction as follows: Page 2, first column, line '21, claim 4, for the word "has" read had; and second column, line 31, claim 10, strike out the words and period "soluble and dissolved in a non-aqueous solvent. and that the said Letters Patent should be read with these corrections therein that the same may conform to the record of the case in the Patent Office.
Signed and sealed this 27th day of July, A. D. 1937.
Henry Van Arsdale (Seal) Acting Commissioner of Patents.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| USRE20383E true USRE20383E (en) | 1937-05-25 |
Family
ID=2085266
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US20383D Expired USRE20383E (en) | Film forming compositions and proc |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | USRE20383E (en) |
-
0
- US US20383D patent/USRE20383E/en not_active Expired
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| USRE20383E (en) | Film forming compositions and proc | |
| DE1058255B (en) | Process for the production of nitrogen-containing epoxy resins | |
| US2670341A (en) | Production of alcohol-modified urea-formaldehyde resins | |
| US1734693A (en) | Process for the manufacture of film-forming solutions | |
| JPS60215010A (en) | Manufacture of resin | |
| US2242484A (en) | Stabilization of resin sirups | |
| US2704750A (en) | Aminoplast resins | |
| US2337635A (en) | Vinyl resin composition | |
| US2221708A (en) | Preparation of urea-formaldehyde resin | |
| US2361715A (en) | Method of preparing urea-formaldehyde lacquers | |
| US2150148A (en) | Water soluble resinous condensation products | |
| US2823237A (en) | Preparation of highly soluble paraformaldehyde | |
| USRE22402E (en) | Coatino composition containing | |
| US2016594A (en) | Moldable urea-formaldehyde reaction product and process of preparing same | |
| US2273788A (en) | Alkyl urea-formaldehyde resin | |
| US1658597A (en) | Condensation product and method of making same | |
| US1844571A (en) | Artificial resin and process of making the same | |
| US2149672A (en) | Process for making a press powder | |
| US2338430A (en) | Process of producing nonyellowing phenol-formaldehyde condensates | |
| US1111287A (en) | Cresolic varnish composition. | |
| US2529784A (en) | Condensation products of urea, monoalkyl urea, formaldehyde, and monohydric aliphaticalcohol | |
| US1896276A (en) | Urea-acetaldehyde-formaldehyde resin and process of making same | |
| US1944867A (en) | Resin solution and method of preparing same | |
| US2574040A (en) | Condensation products of ureides and formaldehyde | |
| US1973918A (en) | Reaction product of sulphur dioxide and aldehyde derivatives of a schiff's base |