US2116640A - Production of molecular compounds - Google Patents
Production of molecular compounds Download PDFInfo
- Publication number
- US2116640A US2116640A US65432A US6543236A US2116640A US 2116640 A US2116640 A US 2116640A US 65432 A US65432 A US 65432A US 6543236 A US6543236 A US 6543236A US 2116640 A US2116640 A US 2116640A
- Authority
- US
- United States
- Prior art keywords
- molecular
- components
- compounds
- urea
- molecular compounds
- 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 - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 title description 33
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 48
- 235000013877 carbamide Nutrition 0.000 description 24
- 239000004202 carbamide Substances 0.000 description 24
- 239000003795 chemical substances by application Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 235000013681 dietary sucrose Nutrition 0.000 description 9
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 8
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 7
- 239000008103 glucose Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 229960004793 sucrose Drugs 0.000 description 7
- 229930006000 Sucrose Natural products 0.000 description 6
- 235000000346 sugar Nutrition 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 239000004753 textile Substances 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000001747 exhibiting effect Effects 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- -1 salt compounds Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 229920002955 Art silk Polymers 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 1
- 229920000715 Mucilage Polymers 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- GUBGYTABKSRVRQ-QUYVBRFLSA-N beta-maltose Chemical compound OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O GUBGYTABKSRVRQ-QUYVBRFLSA-N 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 229960002737 fructose Drugs 0.000 description 1
- 229930182830 galactose Natural products 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 150000002772 monosaccharides Chemical class 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/01—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with natural macromolecular compounds or derivatives thereof
- D06M15/03—Polysaccharides or derivatives thereof
- D06M15/11—Starch or derivatives thereof
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
- D06M13/144—Alcohols; Metal alcoholates
- D06M13/148—Polyalcohols, e.g. glycerol or glucose
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
- D06M13/184—Carboxylic acids; Anhydrides, halides or salts thereof
- D06M13/203—Unsaturated carboxylic acids; Anhydrides, halides or salts thereof
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/402—Amides imides, sulfamic acids
- D06M13/432—Urea, thiourea or derivatives thereof, e.g. biurets; Urea-inclusion compounds; Dicyanamides; Carbodiimides; Guanidines, e.g. dicyandiamides
Definitions
- British Patent No. 251,993 discloses the emp y-'- ment thereof for finishing.
- British Patent No. 285,992- and French Patent N0. 653,658 descr b the use of urea as a swelling'agent for artificial silk, particularly acetate silk, and
- British Patent Nos. 318,978; 318,469 and 262,830 recommend additions of ureato dye-baths.
- ureacan be used also in the presence of other compounds, and on examination it will be found that such other substances are to be added in quantities not narrowly proportionateto the urea used. They constitute therefore pure mixtures, and it was iustiflable to expect that they would disclose merely the properties of their various components.
- sugar of various kinds, such as grape sugar, cane sugar, 8130.
- sugar can be used only within relatively narrow limits, because if applied in larger amounts to the fiber the colors of the textiles will often appear lightly covered thereby and the sugar may come -off. in dust-dike particles.
- this leading with sugar frequently imparts to the fabric an unpleasant sticky feel and causes its rejection by users;
- S accharoses practically suitable for conversion with urea on account of being available in suiiicient quantities are for instance 4- and 5-hydroxyl aldehydes and ketonic alcohols like arablnose, glucose, .galactose, levulose as monosaccharides.
- di-saccharoses cane-sugar, lactose and maltose may be mentioned; and of the polysaccharoses, ramnose. Mixtures of these can of course be used also.
- Example 1 The molecular compound of urea and glucose is obtainedby fusing 60 parts.by weight of urea with 198 p. b. w. 'of finely pulverized dry glucose at water bath temperature. Thesyrup obtained in about one hour normally does not tend to for some time and subjected to occasional'rubbing with a glass rod, small needles will separate therefrom, whereupon the largest portion poi the mass soon solidifies from the center' of crystallization and forms a crystal-magna. For identification application to clay is prferable. The
- Example 2 Viscose silk on the reel is treated with aliquor containing in 100 liters of water 10 kg. of a molecular compound according to Example 1, whereupon the goods are hydro-extracted and dried as usual. Material thus finished discloses an ex- .cellent feel, and its stability as to weight is good.
- Example 3 Pure wool gaberdine is passed on-the padding machine through a liquor containing 3% of ordinary commercial parafiimand of a single bath impregnating agent containing alumina, to which furthermore of a molecular compound of 1 mol. of urea plus 1 mol. of cane-sugar has been both components in ;point.
- the after-treatment of the goods is as usual.
- the finished material has a full feel, sheds water well and after treatment increases 12% in weight.
- carbamide and saccharoses as components in molecular proportion up to 2:1, and disclosing the chemical properties of the said'components, but having lower crystalline force than each of said components and less adhesive power than. sugar in the form of more highly concentratedsolutions.
- "2. As anew composition of matter the mo-.
- lecular compound of 1 molecule carbamide and one molecule glucose said compound melting at 3.
- the process consisting in dissolving molecular quantities of urea and of saccharoses into one another in molecular proportions up to 2:1 while heating up to liquefaction.
- finishing agents fortextiles comprisingmolecular compounds of carbamide and saccha- 8.
- a molecular compound of carbamide' and saceharose components containing up to 2 molecular parts of the former component to one of KURT um.
Description
Patented ay 10, use
'rso, STATES,
a; [rice 2,118,640 PRQDUCTION OF MOLECULAR COMPOUNDS, Kurt Quehl. Zwickau, Germany, assignor to Chemische Fabrik many Theod. Rotta, Zwickau, Ger- 'No Drawing. Application February 24, 1936, Se-
rial No. 65,432. In Germany February 2'1,
. ing such molecular compounds, and to textiles disclosed by the components as such and of a na-- treated therewith.
It' has been proposed already to use ureasfor purposes of thetextile industry. For example,
British Patent No. 251,993 discloses the emp y-'- ment thereof for finishing. British Patent No. 285,992- and French Patent N0. 653,658 descr b the use of urea as a swelling'agent for artificial silk, particularly acetate silk, and British Patent Nos. 318,978; 318,469 and 262,830 recommend additions of ureato dye-baths.
According to these disclosures, ureacan be used also in the presence of other compounds, and on examination it will be found that such other substances are to be added in quantities not narrowly proportionateto the urea used. They constitute therefore pure mixtures, and it was iustiflable to expect that they would disclose merely the properties of their various components.
American Patent No. 1,979,121 showed, however, that molecular compounds of urea and inorganic or organic salts possess properties not ture to render these compounds'excellently suitable for finishing purposes. The urea and 'salt compounds of the general formula rmewomrnnmx.
It is further known to employ in the textile industry sugar of various kinds, such as grape sugar, cane sugar, 8130., for imparting tofabrics greater stiffness and more feel. Sugar, however, can be used only within relatively narrow limits, because if applied in larger amounts to the fiber the colors of the textiles will often appear lightly covered thereby and the sugar may come -off. in dust-dike particles. Furthermore, this leading with sugar frequently imparts to the fabric an unpleasant sticky feel and causes its rejection by users;
. 13 Claims. (Cl. 260-10) According to'the invention, these drawbacks can be avoided by employing molecular compounds 01' urea and saccharoses.
These molecular compounds of urea and a mono-, dior poly-saccharose represent new chemical compounds having a uniform relatively sharp melting point. Like most molecular compounds they possess the chemical properties of their components, but disclose .a considerably different physical'behavior. Theirsolubility conditions in particular are different, as they usually dissolve more easily in water and crystallize much more difiicultly. A remarkable feature of compounds irom such solutions is their low adhesive power. 7
Compounds of this class can be obtained in a simp.e manner by dissolving the components in each other and'heating to liquefaction, i. e., by
.fusing urea in eq imolecular or double equimolecular quantity with. respect to the saccharose, or
by evaporating a solution of both in'a suitable solvent like water, methyl alcohol, etc. on the water bath and heating the residue up to melting. In most cases the temperature of the water bath will be sumcient, though higher temperatures may be useful, especially to insure rapid conversion of the components. According to the kind of saccharoses employed, the time required for conversion differs slightly, though those skilled in the art will have no difflculty in iinding out when; the conversion is completed.
S accharoses practically suitable for conversion with urea on account of being available in suiiicient quantities are for instance 4- and 5-hydroxyl aldehydes and ketonic alcohols like arablnose, glucose, .galactose, levulose as monosaccharides. Of the di-saccharoses, cane-sugar, lactose and maltose may be mentioned; and of the polysaccharoses, ramnose. Mixtures of these can of course be used also.
These molecular compounds crystallize so difficultlythat crystallization can be brought about only by resorting to measures like precipitating with alcohol, rubbing with a glass rod and inoculating theiused mass when cold with asmall .crystal. Identification was effected by the inventor in crystallized material only.
This low crystalline force renders such molecular compounds particularly suitable for finishing purposes, and finishing agents comprising them,
are therefore of great practical importance.
Whilst ithas frequently been observed that thev all tioned is not open to the same objection. It is even possible to load the textiles with larger quantities without causing efllorescence. Furthermore, since the application of agents comprising such molecular compounds makes: it possible to avoid the viscosity of sugar preparations, stickiness cannot appear at all or only to a very slight degree, even in case of high concentrations on the I fiber in typical weighting finishes. Compared with other agents like glycerin, the compounds described are less hydrophilic, whiclris highly desirable, as a fiber loaded for instance with to 20% glycerin, etc. from treating agents discloses such differences in weight depending on atmos-" pheric moisture that trading in such goods and finishing additions and--agents of. a diflerent or It is therefore possible to employ similar (type. them in the presence of glue, gelatin, starch, mucilages,' etc., and even sensitive softening" agents do not produce a reaction with the highly indifierent molecular compounds. Many different a combination effects can thus be obtained, which is of considerable importance in the finishing of textiles. i
' crystallize. Only-when the syrup is left standing.
The following examples are intendedto explain the nature of the invention without limiting it to the disclosures made therein..
Example 1 .The molecular compound of urea and glucose is obtainedby fusing 60 parts.by weight of urea with 198 p. b. w. 'of finely pulverized dry glucose at water bath temperature. Thesyrup obtained in about one hour normally does not tend to for some time and subjected to occasional'rubbing with a glass rod, small needles will separate therefrom, whereupon the largest portion poi the mass soon solidifies from the center' of crystallization and forms a crystal-magna. For identification application to clay is prferable. The
isolated little needlesmelt at 117 Cfafter drying on calcium chloride; glucose is known ,to melt at 85 C. and ur a at 132 C. The relatively sharp melting point s characteristic of the molecular compound. 7,
I v Example 2 y Viscose silk on the reel is treated with aliquor containing in 100 liters of water 10 kg. of a molecular compound according to Example 1, whereupon the goods are hydro-extracted and dried as usual. Material thus finished discloses an ex- .cellent feel, and its stability as to weight is good.
Example 3 Pure wool gaberdine is passed on-the padding machine through a liquor containing 3% of ordinary commercial parafiimand of a single bath impregnating agent containing alumina, to which furthermore of a molecular compound of 1 mol. of urea plus 1 mol. of cane-sugar has been both components in ;point.
added. The after-treatment of the goods is as usual. The finished material has a full feel, sheds water well and after treatment increases 12% in weight.
' Example 4 v The rear side of fancy cotton goods is treated with a finishing. liquor containing in 100' parts of water 5 parts by weight of soluble starch and p. b. w. of a molecular compound of 1 mol. of'
urea and 1 mol. of glucose by spraying. The remainder of the treatment is the usual one. The material obtained is highly weighted, but does not feel sticky, and even at considerable differences in atmospheric .moisture fluctuates in weight only withinpermis'sible limits. g
Iclaim:-' I p 1. As a new composition of matter the-molecularv compound, containing carbamide and saccharoses as components in molecular proportion up to 2:1, and disclosing the chemical properties of the said'components, but having lower crystalline force than each of said components and less adhesive power than. sugar in the form of more highly concentratedsolutions. "2. As anew composition of matter the mo-.
lecular compound of 1 molecule carbamide and one molecule glucose, said compound melting at 3. The process consisting in dissolving molecular quantities of urea and of saccharoses into one another in molecular proportions up to 2:1 while heating up to liquefaction.
4. The; process of producing novel molecular compoundaconsisting in dissolving urea and glucose in molecular quantities up to a 2: 1 ratio into one another at water bath temperature.
5. The process of producing novel molecular compounds, consisting in dissolving urea and saccharoses in molecular quantities up to a 2:1 ratio into one another in the presence of a solvent.
6. The process of producing novel tnolecular compounds, consisting indissolving urea and saccharoses in molecular quantities up to a 2:1 ratiointo one another by evaporation of a comthe water bath.
'7. As finishing agents fortextiles, comprisingmolecular compounds of carbamide and saccha- 8. A molecular compound of carbamide and saccharose components containing up to 2 molecular parts of the former component to one of the latter, exhibiting the chemical properties of said components, butsharply distinguished from respect to a fixed melting '9. A molecular compound of carbamide and s'accharose components containing up to 2 molecular parts of the former component to one of the latter, exhibiting the chemical properties oi said components, but distinguished from the latter component by a low property ofadhesion.
10. .A molecular compound of carbamide and saccharose components. containing up to -2molecular parts of the former component to one ofthe latter, exhibiting the chemical properties of said components, but distinguished from both] components in respect to sluggishness in-crystallization, i. e. crystallization takes place only, when started by introduction of a foreign agent.
11. A-molecular compound of carbamide and mon aqueous solution and heating the residue on,
the latter, exhibiting the chemical properties}! said components, but distinguished from both components in respect to ready solubility and a high capacity of being over-saturated in solution. 12. A molecular compound of carbamide' and saceharose components containing up to 2 molecular parts of the former component to one of KURT um.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE467749X | 1935-02-27 |
Publications (1)
Publication Number | Publication Date |
---|---|
US2116640A true US2116640A (en) | 1938-05-10 |
Family
ID=6540737
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US65432A Expired - Lifetime US2116640A (en) | 1935-02-27 | 1936-02-24 | Production of molecular compounds |
Country Status (2)
Country | Link |
---|---|
US (1) | US2116640A (en) |
GB (1) | GB467749A (en) |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2538903A (en) * | 1947-05-09 | 1951-01-23 | Keever Starch Company | Uniformly substituted esters of glucopyranose polymers |
US2612497A (en) * | 1948-01-24 | 1952-09-30 | Hendrik W Meijer | Process for manufacture of hexose ureides and thioureides |
US2613204A (en) * | 1952-10-07 | of urea | ||
US2666713A (en) * | 1950-02-08 | 1954-01-19 | Nat Sugar Refining Company | Plasticizer and moisture retentive composition for paper and paper containing it |
US2681333A (en) * | 1954-06-15 | Gorin | ||
US2694719A (en) * | 1949-02-12 | 1954-11-16 | Opplt Jan | Method of stabilizing ascorbic acid with alkali-thiosulfate-carbamide-complexes |
US2702249A (en) * | 1950-11-22 | 1955-02-15 | Nat Sugar Refining Company | Reaction product of a sugar and an amino compound, and process of making same |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2549372A (en) * | 1947-04-15 | 1951-04-17 | Extractive fractionation process |
-
1936
- 1936-02-13 GB GB4365/36A patent/GB467749A/en not_active Expired
- 1936-02-24 US US65432A patent/US2116640A/en not_active Expired - Lifetime
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2613204A (en) * | 1952-10-07 | of urea | ||
US2681333A (en) * | 1954-06-15 | Gorin | ||
US2538903A (en) * | 1947-05-09 | 1951-01-23 | Keever Starch Company | Uniformly substituted esters of glucopyranose polymers |
US2612497A (en) * | 1948-01-24 | 1952-09-30 | Hendrik W Meijer | Process for manufacture of hexose ureides and thioureides |
US2694719A (en) * | 1949-02-12 | 1954-11-16 | Opplt Jan | Method of stabilizing ascorbic acid with alkali-thiosulfate-carbamide-complexes |
US2666713A (en) * | 1950-02-08 | 1954-01-19 | Nat Sugar Refining Company | Plasticizer and moisture retentive composition for paper and paper containing it |
US2702249A (en) * | 1950-11-22 | 1955-02-15 | Nat Sugar Refining Company | Reaction product of a sugar and an amino compound, and process of making same |
Also Published As
Publication number | Publication date |
---|---|
GB467749A (en) | 1937-06-23 |
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