US3185539A - Process of treating cellulose textiles with certain alkylenebis(n-carboxamides) and products produced therefrom - Google Patents
Process of treating cellulose textiles with certain alkylenebis(n-carboxamides) and products produced therefrom Download PDFInfo
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- US3185539A US3185539A US86865A US8686561A US3185539A US 3185539 A US3185539 A US 3185539A US 86865 A US86865 A US 86865A US 8686561 A US8686561 A US 8686561A US 3185539 A US3185539 A US 3185539A
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- carboxamides
- alkyl
- alkylenebis
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/30—Oxygen or sulfur atoms
- C07D233/42—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/30—Oxygen or sulfur atoms
- C07D233/40—Two or more oxygen atoms
-
- 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
- D06M13/405—Acylated polyalkylene polyamines
-
- 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
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/39—Aldehyde resins; Ketone resins; Polyacetals
- D06M15/423—Amino-aldehyde resins
Definitions
- glutaraldehyde glutaraldehyde, adipaldehyde, levulinaldehyde, acetoacetaldehyde, 2-propyl-adipaldehyde, suberaldehyde sebacaldehyde (total of 10 carbons), and the like.
- a time of from about one minute to about 10 minutes may be employed at temperatures from 450 to 250 F., respectively.
- curing times of the order of 5 minutes to about /4 minute at a temperature of from between 250 and 450 F., respectively, have been successfully employed.
Description
United States Patent PROCESS OF TREATING CELLULOSE TEXTILES WITH CERTAIN ALKYLENEBIS(N-CARBOXAM- IDES) AND PRODUCTS PRODUCED THERE- FROM Richard K. Madison, Murray Hill, and William J. Van
Loo, Jr., Middlesex, N.J., assignors to American Cyanamid Company, New York, N.Y., a corporation of Maine No Drawing. Filed Feb. 3, 1961, Ser. No. 86,865
" 7 Claims. (Cl. 8 116.3)
This invention relates to novel compounds and more particularly to novel compounds which are suitable for use as textile finishing agents. More particularly, this invention relates to dihydroxyalkylenebis(N-carboxamides) and dialkoxyalkylenebis(N-carboxamides) of the formula:
where R and R are selected from the group consisting of alkyl and alkenyl, R and R are selected from the group consisting of hydrogen, alkyl and phenyl, R and R are selected from the group consisting of hydrogen and lower alkyl and n is 0 to 8 inclusive.
In addition to these novel compounds, which are suitable for use as textile finishing agents, this inventionrelates to a process for finishing or treating cellulose containing textile materials with such agents and to the cellulose textile materials so finished.
According to the present invention, compounds are provided of the formula:
wherein R and R are selected from the group consisting of alkyl or alkenyl, R and R are selected from the group consisting of hydrogen, alkyl and phenyl, R and R are selected from the group consisting of hydrogen and lower alkyl and n is 0 to 8 inclusive.
R and R in the formula above may be alkyl or alkenyl having from 1 to about 20 carbon atoms. In addition, these groups may be straight chained, branch chained,
and with regard to the alkenyl groups these may contain hydrogens, are prepared by reactinga mono-carboxamide with an aliphatic dicarbonyl compound of the formula Rl0 o,.nl. cm
where R and R are selected from the group consisting 3,185,539 Patented May 25, 1965 achieve various effects, including wrinkle resistance and dimensional stability.
Among the monocarboxamides which may be used in the present invention are the alkyl carboxamides (saturated fatty acid amides) of the formula RCONH where R is an alkyl group, and the alkenyl carboxamides (unsaturated fatty acid amides) of the formula for example, where R is hydrogen, alkyl or alkenyl. The double bond may be in other positions and, of course, there may be more than one double bond, as for example, 2 or 3 double bonds.
Examples of the first type of alkyl monocarboxamide are acetamide, propionamide, butyramide, alpha-methylpropionamide, beta-methylbutyramide, valeramide, caproamide, alpha-ethylpropionamide, epsilon-methylcaproamide, capramide, lauramide, palmitamide, stearamide, and the like. Examples of the second type of carboxamide are acrylamide, methacryl-amide, crotonamide, 3-butenamide, Z- entenamide, 4-pentenamide, 2-methyl-3-pentenamide, IO-Undecenamide, oleamide, 2-octadecenamide, 6 octadecenamide, and the like.
The aliphatic dicarbonyl compounds useful in this invention include, by way of example, glyoxal, methyl glyoxal, dimethyl glyoxal, ethyl glyoxal, din-propyl glyoxal, ethyl n-propyl glyoxal, phenyl glyoxal, benzil,
methyl phenyl glyoxal, malonaldehyde, succinaldehyde,
glutaraldehyde, adipaldehyde, levulinaldehyde, acetoacetaldehyde, 2-propyl-adipaldehyde, suberaldehyde sebacaldehyde (total of 10 carbons), and the like.
ployed. Normally, relative amounts of two moles of monocarboxamide per mole of aliphatic dicarbonyl compound are employed. Completion of the reaction can be confirmed analytically, as by free glyoxal determination or other suitable means.
The reaction temperature is normally room temperature, i.e., between about 20 and 30 C., but lower or higher temperatures may be employed, as for example, at temperatures within the range of from 0 to C. at atmospheric pressure.
The reaction between the carboxamides and the aliphatic dicarbonyl compounds is preferably carried out at atmospheric pressure, although subatmospheric and superatmospheric pressures may be employed under suitable circumstances.
The compounds of the instant invention wherein R and R are alkyl groups are normally prepared by reacting the corresponding hydroxy compound with a lower aliphatic monohydric alcohol in the presence of an acid catalyst, and at a pH of less than 4 and normally of less than 2.
The lower aliphatic monohydric alcohols include those of 4 carbon atoms or less, such as methanol, ethanol, the propanols and the butanols. Suitable acids useful as catalysts in this aspect of the instant invention are the mineral acids, such as sulfuric, hydrochloric, nitric, phosphoric, and the like, and the strong organic acids, as for example, oxalic acid, the toluene sulfonic acids and the toluene phosphonic acids, and the like.
The temperatures and pressures at which these reactions are carried out correspond substantially to those at which the reaction between the carboxamides and the glyoxals are carried out. Thus, the reaction is normally carried out at room temperature or at a temperature of from between about 20 and 30 C., although temperatures between C. and 50 C. may be employed. At temperatures below 0 C. the reaction proceeds slowly, while at temperatures above 50 C. there is danger of polymerization.
Preferably on a relative basis at least 2 moles of alcohol per mole of dihydroxyalkylenebis (N-carboxamide) is employed and amounts in excess are preferred, since full alkylation is thereby insured and the excess amounts function as a solvent for the reaction. Normally, the reaction takes from between about 2 minutes to about 10 minutes, the shorter times at the higher temperatures.
As noted above, a principal end use contemplated for the compounds of this invention is as textile finishing agents to impart various properties to the textile material such as wrinkle resistance and dimensional stability, as well as softness of hand, water repellency and the like, to cellulose containing textile materials.
By the term cellulose textile material, as that term and similar terms are employed herein, it is meant fibers, yarns, filaments, formed fabrics, whether woven or nonwoven, felted or otherwise formed, containing at least 50% of cellulose fiber prepared from cotton, rayon, linen, flax and other cellulosic materials. These cellulosic materials may be employed in combination with other non-cellulosic materials, as for example, they may be blended with other natural or synthetic fibers, as for example, silk, wool, nylon, acrylic fibers, polyester fibers and the like.
The compounds of this invention and a suitable curing accelerator or catalyst may be applied to textile materials by any conventional technique such as immersion, padding, spraying and the like, followed where necessary by squeezing, hydroextraction or similar processes in order to afiix the desired amount of resin solids on the fabric.
The method of application should be such that from about 1 to about 25% and in some instances higher amounts of the compound of this invention based on the weight of the fabric are deposited thereon. Within certain limits, the amount of resin applied depends upon the particular type of fabric being treated. Thus, when treating fabric consisting of fibrous cellulosic materials, the concentration of the order of about 1 to 25% and more particularly from 3 to 10% solids, based on the dry weight of the fabric, may be employed.
The catalyst or accelerator employed is an acidic type catalyst and may be a free acid, acid salt, alkanolamine salt, metal salt and the like of the type well known to those in the textile finishing art. The concentration of catalyst employed may range from about 0.1 to about 25% or higher, based on the weight of the solids, depending upon the particular catalyst type employed. Thus, for example, from between about 0.1 and about 10% of a free acid such as phophoric, tartaric, oxalic or the like may be employed, while in the case of ammonium chloride amounts of from between 0.5 and about 10% are used. In the case of amine salts including alkanolamine salts, such as diethanolamine hydrochloride, from about 1 to about 10% are most useful, while with respect to salts such as magnesium chloride amounts of from between about 5 and 25 have been successfully employed. In addition to magnesium chloride, zinc nitrate, aluminum chloride, and other known conventional metal salts are normally employed in amounts corresponding to between 5 and 25 based on the weight of solids.
Following the application of the resin and curing catalyst to the textile fabric, the material is subjected to drying and curing operations in order to effect wrinkle resistance and shrinkage control thereon. The drying and curing operation may be carried out in a single step or in separate steps. The temperatures at which the drying and curing operations are effected vary widely and are influenced to some extent by the type of catalyst employed. Normally, the range of temperature extends from about 180 F. to about 450 F. or even higher. Generally speaking, the time of the drying and/or curing operation is inversely proportional to the temperature employed and of course is influenced by whether or not separate or combined drying and curing steps are employed. Generally, when drying and curing is carried out in a combined operation a time of from about one minute to about 10 minutes may be employed at temperatures from 450 to 250 F., respectively. When the fabric has been dried preliminary to curing, curing times of the order of 5 minutes to about /4 minute at a temperature of from between 250 and 450 F., respectively, have been successfully employed.
In order that the present invention may be more fully understood, the following examples are given primarily by Way of illustration. No specific details or enumerations contained therein should be construed as limitations on the present invention except insofar as they appear in the appended claims. All parts and percentages are by weight unless otherwise specifically designated.
EXAMPLE 1 1,2-dihydr0xyethylenebis(N-acetamide) H It CH3-C-NH(JJ-(E-NHC-CH3 i (311 H O A mixture of 193 parts (1.0 mole) of 30% glyoxal, with the pH adjusted to 7.5 with sodium hydroxide, and 130 parts (2.2 moles) of acetamide was stirred at room temperature until the reaction was complete. The reaction solution was concentrated in vacuo, and the residue was dissolved in ethanol and again concentrated in vacuo. The product was purified by dissolving it in ethanol and passing the ethanolic solution through a chromatographic column packed with activated alumina. From certain fractions of the eluted liquor, crystals were obtained which, after recrystallization from methanol and water, melted at 156 to 157.5 C.
Analysis.Calculated for C H N O C, 40.9; H, 6.87; N, 15.9. Found: C, 39.9; H, 6.94; N, 15.1.
To a solution of 3.8 parts (0.05 mole) of glyoxal, in 10 parts of Water with the pH adjusted to 7.5 with sodium hydroxide, there was added 7.1 parts (0.1 mole) of acrylamide. The reaction mixture was stirred at room temperature until the reaction was complete. The solid product was separated by filtration, and was crystallized by adding ether to a solution in methanol.
Analysis-Calculated for C H N O C, 48.0; H, 6.04; N, 14.0. Found: C, 47.6; H, 5.86; N, 13.6.
EXAMPLE 3 1 ,4 -dihydroxytetramethylenebis (N -acetamide) The procedure of Example 1 is followed substituting an equivalent amount of succinaldehyde for the glyoxal.
EXAMPLE 4 In processes similar to those of Examples 1-3 the indicated aliphatic dicarbonyl compound is reacted with the indicated carboxamide. These reactants and products produced are shown in Table I below.
The products of the above examples are reacted with a lower alcohol using an excess of the alcohol as the reaction medium. Sufiicient hydrochloric acid is added to give a pH below 4.0 Normally the reaction is completed in a few minutes at rom temperature. The products are isolated by well-known methods, as by distillation. The reactants and products are shown in Table II. TABLE II Product of Alcohol Product example 1 Methanol 1,2-dinfthoxyethylenebis(N-acetam1 e t 1 Ethanol 1,2-diethoxyethylenebis(N-acetamide). 2 Methanol"-.. lfighmethoxyethylenebis(N-acrylam- 1 t 2 n-Butanol 1,2-di-n-butoxyethylenebis(N-acrylamide).
EXAMPLE 6 Application of 1,2-dihydrxyethylenebis(N-acetamide) The pad bath contained 5.9% of the product of Example 1, and 0.59% of zinc nitrate (10% on the weight of the compound).
The p-ad bath was applied to 80 x 80 cotton percale with a wet pick-up of 85%. The fabric was dried at 225 F. for 2 minutes and cured at 350 F. for 1.5 minutes.
The results of tests conducted with the treated and untreated fabrics are shown in Table III.
The wrinkle recovery was measured on a Monsanto wrinkle recovery tester following the tentative test methods 66-1956 described on page 157 of the 1958 Technical Manual and Yearbook of the American Association of Textile Chemists and Colourists, vol. 33.
The tensile strength was measured on a Scott tester according to ASTM standards. t
The amount of resin solids on the fabric was determined by analyzing the treated fabric for nitrogen, and from this calculating the percentage of resin solids present.
The results of the tests run on the treated fabric are shown in Table III.
TABLE III Untreated Treated fabric fabric eta Through the R and R groups various modifying groups may be durably applied to cellulosic textile materials. Thus, for example, where R and R are long chain fatty acid compounds, as for example, C-12 through C20, a water resistant or water repellent finish may be imparted to cellulosic textile materials treated therewith.
While it is not known for certain the mechanism by which the compounds of this invention durably bind themselves to cellulosic textile materials, it is believed that whether they be the 1,2-dihydroxy or the 1,2-dialkoxy compounds that under the conditions of cure set forth hereinabove the hydrogen or the alkyl radical is split off to form either Water or alcohol, permitting the compounds of this invention to be durably joined to the cellulose directly through an oxygen linkage.
The compounds of this invention may be employed in combination with other textile finishing resins and in particular aminoplast textile finishing resins, as for example, the melamine-formaldehyde resins, guanamine-formaldehyde resins and their alkylated or etherified deriva tives. Thus, for example, the agents of this invention may be combined with the melamine-formaldehyde resins which are described in U.S. Patent No. 2,197,357 and U.S. Patent No. 2,529,856. Additionally, they may be combined with the various ureas and cyclic ureas known in the textile finishing art. Thus, for example, they may be employed with dimethylol urea, methylated methylol urea, dimethylol ethylene urea, dimethylol 1,2- and 1,3- propylene urea and the like. In addition, they may be combined with thiobis amides of the type described in U.S. Patent No. 2,887,408 and guanamine-formaldehyde condensates of the type described in U.S. Patent No. 2,887,409. Additionally, the compounds of this invention may be combined or employed with the urons such as are described in U.S. Patent No. 2,373,135 and various polyepoxide resins having epoxy equivalents greater than 1, as for example those described in U.S. Patent No. 2,730,427, U.S. Patent No. 2,752,269 and U.S. Patent No. 2,794,754. Further, the resins of this invention may be employed with other textile finishing agents or auxiliaries, as for example, softeners, lubricants, odorants and the like.
We claim: 7
1. A process comprising treating cellulose textile material which comprises applying thereto from 1 to 25%,
based on the dry weight of said material, of a compound of the formula:
where R and R are selected from the group consisting of alkyl and alkenyl having from 1 to about 20 carbon atoms, R and R are selected from the group consisting of hydrogen, alkyl having from 1 to 20 carbon atoms inclusive and phenyl, R and R are selected from the group consisting of hydrogen and lower alkyl, and n is an integer of from 0 to 8 inclusive, and thereafter curing said compound to a water-insoluble state by the action of heat and an acidic catalyst.
2. A process according to claim 1 in which from 3 to 10%, based on the weight of said textile material, is applied.
3. Cellulose textile material resulting from the process of claim 1.
4. A process comprising treating cellulose textile material which comprises applying thereto from 1 to 25%, based on the dry weight of said material, of a compound of the formula:
where R and R are selected from the group consisting of alkyl and alkenyl having from 1 to about 20 carbon atoms, R and R are selected from the group consisting of hydrogen, alkyl having from 1 to 20 carbon atoms inclusive, and phenyl, R and R are hydrogen, and n is an integer of from 0 to 8 inclusive, and thereafter curing said compound to a water-insoluble state by the action of heat and an acidic catalyst.
5. A process comprising treating cellulose textile material which comprises applying thereto from 1 to 25%, based on the dry Weight of said material, of a compound of the formula:
where R and R are selected from the group consisting of alkyl and alkenyl having from 1 to about 20 carbon atoms, R and R are selected from the group consisting of hydrogen, alkyl having from 1 to 20 carbon atoms inclusive, and phenyl, R and R are lower alkyl, and n is an integer of from 0 to 8 inclusive, and thereafter curing said compound to a water-insoluble state by the action of heat and an acidic catalyst.
6. Cellulose textile material resulting from the process of claim 4.
7. Cellulose textile material resulting from the process of claim 5.
References Cited by the Examiner UNITED STATES PATENTS 2,267,685 12/41 Kyrides 260561 2,317,756 4/43 Graenacher et al 8116.3 2,355,265 8/44 Bock et al. 8116.3 2,562,161 7/51 Epelberg et al.
2,923,738 2/60 Williams et al. 260561 NORMAN G. TORCHIN, Primary Examiner.
RICHARD D. NEVIUS, Examiner.
Claims (1)
1. A PROCESS COMPRISING TREATING CELLULOSE TEXTILE MATERIAL WHICH COMPRISES APPLYING THERETO FROM 1 TO 25%, BASED ON THE DRY WEIGHT OF SAID MATERIAL, OF A COMPOUND OF THE FORMULA:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US86865A US3185539A (en) | 1961-02-03 | 1961-02-03 | Process of treating cellulose textiles with certain alkylenebis(n-carboxamides) and products produced therefrom |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8686061 US3079279A (en) | 1961-02-03 | 1961-02-03 | Blends of imidazolidinones and aminoplasts and method for finishing cellulose containing textile material |
| US86865A US3185539A (en) | 1961-02-03 | 1961-02-03 | Process of treating cellulose textiles with certain alkylenebis(n-carboxamides) and products produced therefrom |
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| Publication Number | Publication Date |
|---|---|
| US3185539A true US3185539A (en) | 1965-05-25 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US86865A Expired - Lifetime US3185539A (en) | 1961-02-03 | 1961-02-03 | Process of treating cellulose textiles with certain alkylenebis(n-carboxamides) and products produced therefrom |
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| Country | Link |
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| US (1) | US3185539A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3230030A (en) * | 1962-09-27 | 1966-01-18 | Clifford M Moran | Process of producing wrinkle resistant cellulose fabrics of relatively high moistureregain |
| US3422139A (en) * | 1964-06-09 | 1969-01-14 | Nobel Bozel | Acrylamido-n-glycolic acid and methylol derivative |
| US3428709A (en) * | 1966-08-22 | 1969-02-18 | Geigy Chem Corp | Polymers of n-perfluoboalkanoylamino-and n-perfluoroalkanoylaminoalkyl acrylamides and methacrylamides |
| US6103898A (en) * | 1997-10-02 | 2000-08-15 | Basf Aktiengesellschaft | Preparation of cyclic urea derivatives |
| US20140341800A1 (en) * | 2011-09-30 | 2014-11-20 | Mitsubishi Gas Chemical Company, Inc. | Method for producing aqueous hydrogen peroxide solution |
| CN109749012A (en) * | 2019-01-24 | 2019-05-14 | 湖北中之天科技股份有限公司 | A kind of production method of the environment-friendly type without chlorine polyacrylamide wet strength agent and the application in papermaking |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2267685A (en) * | 1938-07-05 | 1941-12-23 | Monsanto Chemicals | Nu,nu'-lower aliphatic diacyl-nu, nu'-dicyclohexyl alkylene diamines |
| US2317756A (en) * | 1938-05-05 | 1943-04-27 | Soc Of Chemical Ind | Process for improving materials containing cellulose |
| US2355265A (en) * | 1941-04-09 | 1944-08-08 | Rohm & Haas | Textile materials |
| US2562161A (en) * | 1948-02-06 | 1951-07-31 | Cluett Peabody & Co Inc | Stabilization of regenerated cellulose fabric with glyoxal-amide reaction product |
| US2923738A (en) * | 1958-05-08 | 1960-02-02 | Gen Aniline & Film Corp | Addition products of n-alkyl-gamma-hydroxycarboxylic acid amides and alkanolamines |
-
1961
- 1961-02-03 US US86865A patent/US3185539A/en not_active Expired - Lifetime
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2317756A (en) * | 1938-05-05 | 1943-04-27 | Soc Of Chemical Ind | Process for improving materials containing cellulose |
| US2267685A (en) * | 1938-07-05 | 1941-12-23 | Monsanto Chemicals | Nu,nu'-lower aliphatic diacyl-nu, nu'-dicyclohexyl alkylene diamines |
| US2355265A (en) * | 1941-04-09 | 1944-08-08 | Rohm & Haas | Textile materials |
| US2562161A (en) * | 1948-02-06 | 1951-07-31 | Cluett Peabody & Co Inc | Stabilization of regenerated cellulose fabric with glyoxal-amide reaction product |
| US2923738A (en) * | 1958-05-08 | 1960-02-02 | Gen Aniline & Film Corp | Addition products of n-alkyl-gamma-hydroxycarboxylic acid amides and alkanolamines |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3230030A (en) * | 1962-09-27 | 1966-01-18 | Clifford M Moran | Process of producing wrinkle resistant cellulose fabrics of relatively high moistureregain |
| US3422139A (en) * | 1964-06-09 | 1969-01-14 | Nobel Bozel | Acrylamido-n-glycolic acid and methylol derivative |
| US3428709A (en) * | 1966-08-22 | 1969-02-18 | Geigy Chem Corp | Polymers of n-perfluoboalkanoylamino-and n-perfluoroalkanoylaminoalkyl acrylamides and methacrylamides |
| US6103898A (en) * | 1997-10-02 | 2000-08-15 | Basf Aktiengesellschaft | Preparation of cyclic urea derivatives |
| US20140341800A1 (en) * | 2011-09-30 | 2014-11-20 | Mitsubishi Gas Chemical Company, Inc. | Method for producing aqueous hydrogen peroxide solution |
| CN109749012A (en) * | 2019-01-24 | 2019-05-14 | 湖北中之天科技股份有限公司 | A kind of production method of the environment-friendly type without chlorine polyacrylamide wet strength agent and the application in papermaking |
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