US2386631A - Permanent waterproofing product and process of making it - Google Patents
Permanent waterproofing product and process of making it Download PDFInfo
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- US2386631A US2386631A US503665A US50366543A US2386631A US 2386631 A US2386631 A US 2386631A US 503665 A US503665 A US 503665A US 50366543 A US50366543 A US 50366543A US 2386631 A US2386631 A US 2386631A
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
Definitions
- the present invention relates to new compositlOns which are suitable for the treatment of textiles or other fibrous materials and to the process of making such compositions.
- An object of the invention is to provide waterdispersible materials which, when applied to textile fabrics and thereafter decomposed on the fabrics, will render them distinctly water-repellent.
- the particular merit ofthe treatment is that the water-repellent property imparted to these fabrics is still effective after repeated drycleaning or laundering.
- compositions will be effective when applied to yarns, threads, or fabrics composed of wool, viscose rayon, cotton, nylon or acetate rayon.
- a process is known whereby a long chain I aliphatic nitrile is reacted with a long chain fatty acid chloride in the presence of an aldehyde and the reaction product so formed is then reacted with a tertiary amine to form a water soluble compound (U. S. Patent No. 2,285,948). It is also known that compounds prepared by this process have not proved to be of practical value because the degree of water repellency which is imparted by them is not up to the accepted standards of the trade. It has been demonstrated conclusively that when these compounds are applied to a cotton fabric under the most ideal conditions, a water repellent effect of not over 80, as measured by a standard spray test,
- Theminimum rating acceptable on this type of fabric is 90.
- wax is here used to designate materials which are commercially known as waxes but do not necessarily come within the technical definition of the term.
- a 3% dispersion of this product in water is usually sufilcient to impart excellent water repellent effects to fabrics.
- Waxes which are suitable for this purpose are those containing appreciable quantities of fatty acids and of aliphatic hydrocarbons possessing a chain length of not less than 20 carbon atoms.
- Some waxes which fall in this classification are montan wax, candelilla wax, carnauba wax and beeswax.
- any other agent may be substituted which is capable of reacting with carboxylic acids to form acid halides.
- Phosphorus pentachloride, sulfuryl chloride and thionyl chloride are well known reactants of this type.
- Suitable aliphatic nitriles are those containing a chain length of not less than 10 carbon atoms.
- the aldehydes which have been found most suitable are formaldehyde andacetaldehyde. These are most conveniently employed in their polymeric form as paraformaldehyde and paraldehyde respectively.
- tertiary amines which may be employed are pyridine, picoline,
- tripropylamineand so forth As, inert solvents there may be used ethyl acetate, dioxane, toluene,
- Eaiample I.300 parts of bleached montan wax was heated with 60 parts of phosphorus trichloride at 70 to 80 C. for 5 hours without agitation in a fiask equipped with a reflux condenser. 293 parts of the reaction product was then poured into another flask. 265 parts of octadecane nitrile, 60 parts of paraformaldehyde and 7.1 parts of anhydrous zinc chloride were added. The flask was made air tight and the mixture was heated to 77 C. and maintained within 3 degrees of this temperature for '1 hours with continuous agitation. At the end of this period the mass was cooled to 70 C. and 88 parts of pyridine was added at such a rate that the temperature did not rise above 80 C. Finally, the mixture was agitated for 30 minutes at 70 to 80 C.
- the resulting composition at room temperature was a hard, brown, tacky solid of about the consistency of beeswax, whic dispersed readily in water at a temperature of 7 Q.
- Example 112-2085 parts of re ed candelilla wax was heated with 41'! parts of phosphorus trichloride for 3 hours at 70 to 80 C. in a glass lined autoclave equipped with a reflux condenser. At the end or this period, the mixture was cooled to 60 C. and 2260 parts of hexadecane nitrile,
- the resulting composition after cooling to room temperature, was a tan-colored solid which was readily dispersible in-warm water.
- Example 1II -250 parts of carnauba wax, 250 parts of octadecane nitrile and 300 parts of ethyl acetate were heated to 65 C. and'allowed to mix until solution was complete. The temperature was then lowered to 50 C. and 5.0 parts of phosphorus trichloride was added. An exothermic process I have described. It
- the final composition was of a firm pasty consistency and was light tan in color. It dispersed with ease in water at 60 C.
- Example IV 250 parts of candelilla wax, 250 parts of hexadecane nitrile and 300 parts of dioxane were heated to 65 C. and allowed to mix until solution was complete. The temperature was then lowered to C. and 130 parts of thionyl chloride was added. The temperature was allowed to rise to 65 C. and was maintained at this point for 1 hour. The mixture was then cooled to C. and 88 parts of paraldehyde was added. The temperature was again allowed to rise to 65 C. and was maintained at this point for 4 hours. The mixture was cooled again to 55 0., 125 parts of 2,6 lutidine was added and allowed to react at to C. for 30 minutes. The mass was then cooled to room temperature.
- the final composition was a tacky solid of a reddish brown color and was readily dispersible in water at C.
- Example V.-For treating a textile the following procedure may be employed:
- the. spray test rating is 90, and after 3 standard laboratory dry-cleanings the spray test rating is 80.
- the process or'making a waterproofing composition which comprises heating a wax selected from the group consisting of montan wax, can- .delilla, carnauba and beeswax, with a chloride selected from the group consisting of phosphorus trichloride, phosphorus, pentachloride, sulfuryl chloride and thionyl chloride, heating the reaction product with an aliphatic nitrile having a chain length of at least 10 carbon atoms, and an aldehyde until. reaction has ceased, and thereafter heating the reaction product with a tertiary amine until a water-dispersible product has been secured.
- a wax selected from the group consisting of montan wax, can- .delilla, carnauba and beeswax
- a chloride selected from the group consisting of phosphorus trichloride, phosphorus, pentachloride, sulfuryl chloride and thionyl chloride
- the process which comprises heating a wax of the type which contains appreciable quantities of free fatty acids and hydrocarbons having a chain length of at least carbon atoms, with an agent which reacts with carboxylic' acids to .form acid halides, at a temperature of from about" C. to about 80 C. and thenheating this reaction mass with an aliphatic nitrile having a chain length of not less than 10 carbon atoms, and an aldehyde at a temperature of from about C. to about 80 C. until reaction has ceased, and thereafter heating the reactionprodnot with a tertiary amine at a temperature of I from about 50 C. to about 80 C. until awhile!- dispersible product has been secured.
- the process which comprises heating candeliila wax and phosphorus trichloride at a temperature of from about 50 C. to 80 0., then heating the reaction mass with formaldehyde 20 and octadecane nitrile at a temperature of from about 60 C. to about 80 C. until reaction has ceased, and thereafter heating the reaction prod-' not with pyridine at a temperature of ⁇ man about 50 C. to about 80 C. until a water-dispersible 25 product has been secured.
- a composition of matter for waterproofing of textiles which consists of the reaction product oi a wax containing appreciable quantities of free fatty acids and hydrocarbons both having so at least 10 carbon atomsin the chain, with an agent which reacts with carboxylic acids to form acid halides, the reaction mass having been heated with an aliphatic nitrile having a chain length of at least 10 carbon atoms, and an alde- 55 hyde until reaction has ceased. and that product having been heated with a tertiary amine until a water-dispersible product has been secured.
- composition of matter comprising the reaction product oi (a) a wax selected from the 4 group consisting of montan wax, candelilla,
- a chloride selected from the group consisting of phosphorus trichloride, phosphorus pentachloride, sulfuryi chloride, and thionyl chloride, (0) a long chain aliphatic nitrile, and (d) an aldehyde, and which product is heated and reacted with a tertiary amine.
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
rmsaa a. 9,1945
PERMANENT WATERPROOFING PRODUCT AND PROCESS OF MAKING I'l Raymond A. Pingree, Cranston, B. Lfanignor to Warwick Chemical CompannWarwick, It. 1., -a corporation of Rhode Island No Drawing.
Application September 24, 1943, Serial No. 503,685
12 Claims. (Cl. 260-295) This application is a. continuation-impart of my prior application Serial No. 429,400, filed February 3, 1942.
The present invention relates to new compositlOns which are suitable for the treatment of textiles or other fibrous materials and to the process of making such compositions.
An object of the invention is to provide waterdispersible materials which, when applied to textile fabrics and thereafter decomposed on the fabrics, will render them distinctly water-repellent. The particular merit ofthe treatment is that the water-repellent property imparted to these fabrics is still effective after repeated drycleaning or laundering.
It has been found that these compositions will be effective when applied to yarns, threads, or fabrics composed of wool, viscose rayon, cotton, nylon or acetate rayon.
A process is known whereby a long chain I aliphatic nitrile is reacted with a long chain fatty acid chloride in the presence of an aldehyde and the reaction product so formed is then reacted with a tertiary amine to form a water soluble compound (U. S. Patent No. 2,285,948). It is also known that compounds prepared by this process have not proved to be of practical value because the degree of water repellency which is imparted by them is not up to the accepted standards of the trade. It has been demonstrated conclusively that when these compounds are applied to a cotton fabric under the most ideal conditions, a water repellent effect of not over 80, as measured by a standard spray test,
is obtained. Theminimum rating acceptable on this type of fabric is 90.
I have found that if in this process the long chain fatty acid chloride is substituted by the product of reaction between phosphorus trichloride, or its equivalent, and certain waxes, a final product is obtained, which, when applied to the fabric above mentioned, will impart a water repellent effect of 100. The term "wax is here used to designate materials which are commercially known as waxes but do not necessarily come within the technical definition of the term.
My process may be described briefly as follows:
weight hydrocarbons is treated with phosphorus trichloride at a temperaturetor 0 to 80 C. for 30 minutes to 5 hours ililie' product resulting from this reaction is the rtmixed with an aliphatic nitrlle and an aldehyde and allowed to react at A wax of the type which contains, appreciable quantities of both fatty acids and high molecular chloride, aluminum chloride and the like. A tertiary amine is then added and allowed to react at 50 to C. for 15 minutes to 1 hour. The product so prepared becomes a firm, waxy solid when cold, and is readily dispersible in warm water. It has been found that the, nitriiamay be incorporated at the very beginning without adversely affecting the process. Any or all of thesereactions may be carried out in the presence of an inert solvent to facilitate control during the manufacturing process.
A 3% dispersion of this product in water is usually sufilcient to impart excellent water repellent effects to fabrics. In order to retain this eifect through laundering and dry-cleaning Waxes which are suitable for this purpose are those containing appreciable quantities of fatty acids and of aliphatic hydrocarbons possessing a chain length of not less than 20 carbon atoms.
Some waxes which fall in this classification are montan wax, candelilla wax, carnauba wax and beeswax.
In place of phosphorus trichloride any other agent may be substituted which is capable of reacting with carboxylic acids to form acid halides. Phosphorus pentachloride, sulfuryl chloride and thionyl chloride are well known reactants of this type.
Suitable aliphatic nitriles are those containing a chain length of not less than 10 carbon atoms. The aldehydes which have been found most suitable are formaldehyde andacetaldehyde. These are most conveniently employed in their polymeric form as paraformaldehyde and paraldehyde respectively. Among the tertiary amines which may be employed are pyridine, picoline,
lutidine, quinoline, quinaldine, tributylamine,
tripropylamineand so forth. As, inert solvents there may be used ethyl acetate, dioxane, toluene,
carbon tetrachloride or other anhydrous solvents thus produced are treated with a tertiary amine it seems probable that quaternary ammonium compounds are formed. The hydrocarbons present in the wax are apparently carried along mechanically and remain dissolved in the quaternary ammonium compounds or are present in a finely dispersed or colloidal state.
Whatever the chemical or physical nature of these final compositions may be, I have been unable to reproduce them by mechanically mixing together pure hydrocarbon waxes and compounds produced by the aforementioned process described in U. S. Patent 2,285,948. To demonstrate this point I have conducted numerous experiments in which high molecular weight hydrocarbon waxes were incorporated at various stages in this process but none of the compositions so prepared were found to be as eilective as those produced by the therefore seems that although the hydrocarbons contained in the wax are essential constituents of the final composition, they do not exist as components of a simple mechanical mixture but are present in such a state as to impart certain desirable properties to the composition which cannot be obtained by other means. 4
The following examples are given to illustrate the process and products of the present invention:
Eaiample I.300 parts of bleached montan wax was heated with 60 parts of phosphorus trichloride at 70 to 80 C. for 5 hours without agitation in a fiask equipped with a reflux condenser. 293 parts of the reaction product was then poured into another flask. 265 parts of octadecane nitrile, 60 parts of paraformaldehyde and 7.1 parts of anhydrous zinc chloride were added. The flask was made air tight and the mixture was heated to 77 C. and maintained within 3 degrees of this temperature for '1 hours with continuous agitation. At the end of this period the mass was cooled to 70 C. and 88 parts of pyridine was added at such a rate that the temperature did not rise above 80 C. Finally, the mixture was agitated for 30 minutes at 70 to 80 C.
The resulting composition at room temperature was a hard, brown, tacky solid of about the consistency of beeswax, whic dispersed readily in water at a temperature of 7 Q.
Example 112-2085 parts of re ed candelilla wax was heated with 41'! parts of phosphorus trichloride for 3 hours at 70 to 80 C. in a glass lined autoclave equipped with a reflux condenser. At the end or this period, the mixture was cooled to 60 C. and 2260 parts of hexadecane nitrile,
500 parts of paraformaldehyde and 52.5 parts of anhydrous zinc chloride were added. The autoclave was made air tight, and with agitator in motion the temperature was allowed to rise to 77 to 80 C. and was held at this point for six hours. The temperature was then reduced to 70 C. and 816 parts of pyridine was added" at such a rate that the temperature did not rise above 80 C., where it was maintained for a period of 30 minutes.
The resulting composition, after cooling to room temperature, was a tan-colored solid which was readily dispersible in-warm water.
Example 1II.-250 parts of carnauba wax, 250 parts of octadecane nitrile and 300 parts of ethyl acetate were heated to 65 C. and'allowed to mix until solution was complete. The temperature was then lowered to 50 C. and 5.0 parts of phosphorus trichloride was added. An exothermic process I have described. It
a,ssc,cs1
' hydes, is obscure, but when the reaction-products reaction occurred which caused the temperature to rise to 65 C. at which point it was maintained for 2 hours. The temperature was then lowered to 55 C. and 61 parts of paraformaldehyde was added. An exothermic reaction occurred which caused the temperature to rise to 65 C. at which point it was maintained for 3 hours. The temperature was lowered again to 55 C, and 110 parts of beta-picoline was added. After 15 minutes the product was cooled to room temperature.
The final composition was of a firm pasty consistency and was light tan in color. It dispersed with ease in water at 60 C.
Example IV.250 parts of candelilla wax, 250 parts of hexadecane nitrile and 300 parts of dioxane were heated to 65 C. and allowed to mix until solution was complete. The temperature was then lowered to C. and 130 parts of thionyl chloride was added. The temperature was allowed to rise to 65 C. and was maintained at this point for 1 hour. The mixture was then cooled to C. and 88 parts of paraldehyde was added. The temperature was again allowed to rise to 65 C. and was maintained at this point for 4 hours. The mixture was cooled again to 55 0., 125 parts of 2,6 lutidine was added and allowed to react at to C. for 30 minutes. The mass was then cooled to room temperature.
The final composition was a tacky solid of a reddish brown color and was readily dispersible in water at C.
Example V.-For treating a textile, the following procedure may be employed:
8 parts of the composition prepared according to any of the previous samples is dispersed in 192 parts of water at 60 C. 1.6 parts of sodium acetate trihydrate is then added and stirred until dissolved. A piece of cotton poplin is treated with this mixture by the conventional padding method. The fabric is air-dried at to C. for 1 minute. It is then subjected to a temperature of C. for 3 minutes after which the fabric is immersed for 1 minute at 50 C. in a solution containing 0.2% sodium carbonate and 0.5% sodium oleate. It is then rinsed thoroughly in hot and cold water and is finally dried at 80 to 90 C. again. After being allowed to regain its natural moisture content the treated fabric is found to possess a water repellency of 100, as
measured by the standard spray test method.
After being subjected to 3 standard laboratory launderings, the. spray test rating is 90, and after 3 standard laboratory dry-cleanings the spray test rating is 80.
Having thus described my invention, 'what I claim as new and desire to secure by Letters Paten is:
1. The process or'making a waterproofing composition which comprises heating a wax selected from the group consisting of montan wax, can- .delilla, carnauba and beeswax, with a chloride selected from the group consisting of phosphorus trichloride, phosphorus, pentachloride, sulfuryl chloride and thionyl chloride, heating the reaction product with an aliphatic nitrile having a chain length of at least 10 carbon atoms, and an aldehyde until. reaction has ceased, and thereafter heating the reaction product with a tertiary amine until a water-dispersible product has been secured.
2. The process which comprises heating wax oithe type whichcontains appreciable quantities of free fatty acids and aliphatic hydrocarbons having a chain length of at least 10 carbon atoms, with an agent which reacts with caragent which reacts with carboxylic acids to form x acid halides. heating this reaction mass with an aliphatic nitrile having a chain length of at least carbon atoms, and an aldehyde, until reaction has ceased, and thereafter heating the reaction product with a tertiary amine until a water-dispersibie product has been secured.
4. The process as set forth in claim 1. wherein all 01' the reactions are carried out in the pres ence of an inert solvent.
5. The process which comprises heating a wax of the type which contains appreciable quantities of free fatty acids and hydrocarbons having a chain length of at least carbon atoms, with an agent which reacts with carboxylic' acids to .form acid halides, at a temperature of from about" C. to about 80 C. and thenheating this reaction mass with an aliphatic nitrile having a chain length of not less than 10 carbon atoms, and an aldehyde at a temperature of from about C. to about 80 C. until reaction has ceased, and thereafter heating the reactionprodnot with a tertiary amine at a temperature of I from about 50 C. to about 80 C. until awhile!- dispersible product has been secured.
6. The process as defined in claim 5, in which all of the reactions are carried out in the presence of an inert solvent.
7. The process which comprises heating montan wax with phosphorus trichloride at to 0. without agitation and with reflux condensation, heating the reaction product with octadecane nitrile, paraformaldehyde, and anhydrous zinc chloride to 77 C. with continuous agitation. adding pyridine at such a rate that the temperature does not rise above 80' C. and a'gitating themixtureat 70to 80C.
8. The process which comprises heating candelilla wax with phosphorus trichlori de.
with m condensation and at to" to so c...
cooling, adding hexadecane nitrile, paraformaldehyde, and anhydrous zinc chloride, holding the reaction mixture at 77 to 80. C. with agitation, cooling to about 70 0., and adding pyridine at such a rate that the temperature does not rise above 80' O.
9. The process which comprises forming a solution of candelilla wax and hexadecane nitrile in dioxane; adding thionyl chloride, maintaining the temperature at about 65 C. for about 1 hour, cooling the mixture to about 55 (1., adding paraldehyde, maintaining the temperature at about C. for about 4 hours, cooling to about 15 55 0., and adding lutidine.
10. The process which comprises heating candeliila wax and phosphorus trichloride at a temperature of from about 50 C. to 80 0., then heating the reaction mass with formaldehyde 20 and octadecane nitrile at a temperature of from about 60 C. to about 80 C. until reaction has ceased, and thereafter heating the reaction prod-' not with pyridine at a temperature of {man about 50 C. to about 80 C. until a water-dispersible 25 product has been secured.
11. A composition of matter for waterproofing of textiles, which consists of the reaction product oi a wax containing appreciable quantities of free fatty acids and hydrocarbons both having so at least 10 carbon atomsin the chain, with an agent which reacts with carboxylic acids to form acid halides, the reaction mass having been heated with an aliphatic nitrile having a chain length of at least 10 carbon atoms, and an alde- 55 hyde until reaction has ceased. and that product having been heated with a tertiary amine until a water-dispersible product has been secured.
,12. A composition of matter comprising the reaction product oi (a) a wax selected from the 4 group consisting of montan wax, candelilla,
carnauba, and beeswax, (b) a chloride selected from the group consisting of phosphorus trichloride, phosphorus pentachloride, sulfuryi chloride, and thionyl chloride, (0) a long chain aliphatic nitrile, and (d) an aldehyde, and which product is heated and reacted with a tertiary amine.
RAYMOND A. PINGREE.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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US503665A US2386631A (en) | 1943-09-24 | 1943-09-24 | Permanent waterproofing product and process of making it |
Applications Claiming Priority (1)
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US503665A US2386631A (en) | 1943-09-24 | 1943-09-24 | Permanent waterproofing product and process of making it |
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US2386631A true US2386631A (en) | 1945-10-09 |
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US503665A Expired - Lifetime US2386631A (en) | 1943-09-24 | 1943-09-24 | Permanent waterproofing product and process of making it |
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2493360A (en) * | 1946-12-11 | 1950-01-03 | Sun Chemical Corp | Materials for imparting water repellency to textile materials and processes for producing and using the same |
US2497324A (en) * | 1947-06-23 | 1950-02-14 | Schenkman Irving | Brassiere |
US2993748A (en) * | 1959-12-10 | 1961-07-25 | Nathan H Koenig | Treatment of wool with acid chlorides in the presence of dimethylformamide |
-
1943
- 1943-09-24 US US503665A patent/US2386631A/en not_active Expired - Lifetime
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2493360A (en) * | 1946-12-11 | 1950-01-03 | Sun Chemical Corp | Materials for imparting water repellency to textile materials and processes for producing and using the same |
US2497324A (en) * | 1947-06-23 | 1950-02-14 | Schenkman Irving | Brassiere |
US2993748A (en) * | 1959-12-10 | 1961-07-25 | Nathan H Koenig | Treatment of wool with acid chlorides in the presence of dimethylformamide |
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