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US2243544A - Composition of matter - Google Patents

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Publication number
US2243544A
US2243544A US267519A US26751939A US2243544A US 2243544 A US2243544 A US 2243544A US 267519 A US267519 A US 267519A US 26751939 A US26751939 A US 26751939A US 2243544 A US2243544 A US 2243544A
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US
United States
Prior art keywords
zinc soap
soap
zinc
water
cocoanut oil
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
Application number
US267519A
Inventor
Horst William P Ter
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Uniroyal Inc
Original Assignee
United States Rubber Co
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by United States Rubber Co filed Critical United States Rubber Co
Priority to US267519A priority Critical patent/US2243544A/en
Application granted granted Critical
Publication of US2243544A publication Critical patent/US2243544A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/10Treating 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
    • D06M13/224Esters of carboxylic acids; Esters of carbonic acid

Definitions

  • This invention relates to new compositions of matter, and manners of preparing, and using the same.
  • cocoanut oil which is composed of a mixture of the glycerides or certain monocarboxylic acids, will react with zinc oxide or carbonate to form a producteomprising amixture of the zinc salts of the cocoanut'oil fatty acids, and that such unseparated mixture of salts (hereinafter called the zinc soap of cocoanut oil) has a restricted use because of its limitedsolubility in many of the common non-polar solvents such as gasoline, solvent naphtha, kerosene, acetone, benzol, xylol, carbon tetrachloride, etc. overcome this deficiency 01' the ginc soap'of cocoanut oil.
  • a further object is to provide a com- Position therefrom which is compatible with vari ous substances and which is capable of use in a wide variety of fields.
  • the zinc soap of "cocoanut oil is solubilized," i. .e. rendered capable of solution in many organic solventsincluding acetone, benzol, xylol, solvent naphtha, gasoline, kerosene, carbon tetrachloride, etc.
  • This- An object of the present invention is tv Cir one part of the zinc soap, .one'part of monobenzylamine or 2 parts of a mix composed of 25% monobenzylamine and 75% dibenzylamine by weight.
  • the zinc'soap may'be suspended in the desired solvent, and the amine added until solution of the zinc soap occurs.
  • the proportions of the zinc soap and the amine may be varied widely depending upon the results desired. Generally, at least'one molecular proportion of the zinc soap may be used for eac molecular proportion of the amine.
  • A is the complex compound obtained by' mixby combining 1- part 01' the zinc soap with 2 1 parts of a mix comprising 25% monobenzylamine and 75% dibenzylamine.
  • Example l When 1 part morpholine is added to 2 parts of the zinc soap of cocoanut oil, a vis-' cous liquid product results which is soluble in acetone, benzol, -xylol, kerosene, carbon tetrachloride, etc. I
  • Example 3.A As a plasticizer for rubber hydrochloride, with which the soluble zinc soap is compatible: To one of two solutions of rubber in the Fade-O-Meter.
  • Example 5 As a waterproofing and mothprooflng agent: This application or use is of particular merit because treatment of material with the "solubilized zinc soap of cocoanut'oil followed by treatment with water, results in the retention on the material of the insoluble zinc soap, whereas the water soluble amine component is removed with the water.
  • a permanent insoluble deposit of the insoluble zinc soap is obtainable on any textile material such as cotton, linen, rayon, natural silk, weighted silk, wool, as well as on paper.
  • a cotton fabric was impregnated with a 2% solution of A in acetone. A funnel was made of the so-treated fabric and water was poured into it. After two weeks time not one drop of water had passed through, indicating the excellent water resistance of the fabric.
  • aqueous dispersions may be used which can readily be prepared by adding the zinc soap
  • . such as .Alphasol, a commercial product, may
  • the materials treated with 2-6% dispersion of zinc soap in water show excellent waterproofing characteristics, and remain substantially waterprooi in dry cleaning. Moreover,- fabrics so treated are substantially mothproof.
  • Solubilized zinc soap of cocoanut oil may be used as an insect repellent to treat and protect fabrics that are normally attacked by moths and other insects.
  • solubilized product uses of the solubilized product are as an activator in connectionxwith vulcanization accelerators, in rubber cements or natural or artificially-prepared latices of rubber as a water repellent or mildew preventative, in paints and varnishes, in lubricating oils (to impart oillness to extreme pressure lubricants), etc., and as a mildew preventative in textile and the like.
  • Zinc soap of cocoanut oil fatty acids com.- bined with an amine selected from the class consisting of morpholine, monobenzylamine, pyridine, ethylene diamine, piperidine, monocyclohexylamine, monoethanolamine. diethanolamine, triethanolamine, triamylamine.
  • a zinc soap of cocoanut oil combined with an amine selected from the class consisting of morpholine. monobenzylamine pyridlne, ethylene diamine,
  • piperidine monocyclohexylamine, monoethanolamine, diethanolamine, triethanolamine, triamylamine.
  • a process of water-proofing and moth-proo ing textile material which comprises treating the same with a zinc soap of cocoanut oil combined with an amine selected from the class consisting of morpholine, monobenzylamine, pyridine, ethylene diamine, piperidine, monocyclohexylamine. monoethanolamine, diethanolamine, triethanolamine, triamylamine.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Description

. tial.
Patented May 27, 1941 COMPOSITION 01f MATTER William P. m- Horst, rams Lake, N. 1..- signer to United States Rubber Company, New
York, N. Y., a corporation of New Jersey No Drawing. Applicationjp'ril 12, '1939,
- Serial No. 267,519
' 8 Claims. (01. 1 7 -22) This invention relates to new compositions of matter, and manners of preparing, and using the same.
It is known that cocoanut oil, which is composed of a mixture of the glycerides or certain monocarboxylic acids, will react with zinc oxide or carbonate to form a producteomprising amixture of the zinc salts of the cocoanut'oil fatty acids, and that such unseparated mixture of salts (hereinafter called the zinc soap of cocoanut oil) has a restricted use because of its limitedsolubility in many of the common non-polar solvents such as gasoline, solvent naphtha, kerosene, acetone, benzol, xylol, carbon tetrachloride, etc. overcome this deficiency 01' the ginc soap'of cocoanut oil. A further object is to provide a com- Position therefrom which is compatible with vari ous substances and which is capable of use in a wide variety of fields.
According to the invention the zinc soap of "cocoanut oil is solubilized," i. .e. rendered capable of solution in many organic solventsincluding acetone, benzol, xylol, solvent naphtha, gasoline, kerosene, carbon tetrachloride, etc. This- An object of the present invention is tv Cir one part of the zinc soap, .one'part of monobenzylamine or 2 parts of a mix composed of 25% monobenzylamine and 75% dibenzylamine by weight.
If desired, the zinc'soap may'be suspended in the desired solvent, and the amine added until solution of the zinc soap occurs.
. The proportions of the zinc soap and the amine may be varied widely depending upon the results desired. Generally, at least'one molecular proportion of the zinc soap may be used for eac molecular proportion of the amine.
' It has also been found that-solubilized" zinc soap of cmoanut oil can be usefully employed .in various fields as the examples below illustrate. A is the complex compound obtained by' mixby combining 1- part 01' the zinc soap with 2 1 parts of a mix comprising 25% monobenzylamine and 75% dibenzylamine.
is best done by treatment or the soap with an reaction is unknown. Amines ln general do not give the "solubilizing" effect with respect to or"- ganic solvents; negative results obtain with aniline, diphenylamine, and dibenz ylamine. Pyridine, ethylene diamine, piperidine, monocyclohexylamine, mono-, dior triethanolamine or 1 triamylamine may-be used, although they are less eflective than morpholine or--monobenzylamine.
Another unusual is that the feet of the amines seems to be specific to the zinc soap or the cocoanut oil and does not take place with chemically pure zinc laurate. The presence of the salts of fatty acidsother than lauric, viz: caproic, myristic', and caprylic seems to be essen- The following examples illustrate the production of solubilized" zinc soap 0! cocoanut oil, the parts being by weight:
Example l.When 1 part morpholine is added to 2 parts of the zinc soap of cocoanut oil, a vis-' cous liquid product results which is soluble in acetone, benzol, -xylol, kerosene, carbon tetrachloride, etc. I
Similar results may be obtained by adding to .Pale ere Example 2.-Productlon oi highly transparent rubber: .The following recipes were used:
Parts Zinc salt of Captax l Sulfur 1.0 1.
Stinpmol war I n The compounded stocks were vulcanized by heating in water at 210 F. for 10 minutes. Excellent transparency was obtained as shown by the, fact that these stocks transmitted-85% of direct sunlight. Distant objects or those nearby can be seen learly through the cured rubber.
These remarkab e results are believed to be due soap com- ,1 rubber compounding ingredient.
Example 3.As a plasticizer for rubber hydrochloride, with which the soluble zinc soap is compatible: To one of two solutions of rubber in the Fade-O-Meter.
'not only plasticized the rubber hydrochloride hydrochloride in 'benzol was added 15% of A. Films were cast and exposed to ultra-violet light The soluble" zinc soap film but also prolonged its useful life. After ap-. proximately 24 hrs. in the Fade-O-Meter the untreated rubber hydrochloride film had turned compositions, with which the soluble" soap is also compatible, and serves as a plasticizer and/or water repellent: 30% by weight of A and B, respectively, were incorporated into so- I lution of nitrocellulose of second viscosity in ethyl acetate; ,Cast films made from the above solution remained clear and transparent.
Example 5.--As a waterproofing and mothprooflng agent: This application or use is of particular merit because treatment of material with the "solubilized zinc soap of cocoanut'oil followed by treatment with water, results in the retention on the material of the insoluble zinc soap, whereas the water soluble amine component is removed with the water. Thus a permanent insoluble deposit of the insoluble zinc soap is obtainable on any textile material such as cotton, linen, rayon, natural silk, weighted silk, wool, as well as on paper. For example, a cotton fabric was impregnated with a 2% solution of A in acetone. A funnel was made of the so-treated fabric and water was poured into it. After two weeks time not one drop of water had passed through, indicating the excellent water resistance of the fabric.
Instead of applying the soluble zinc soap of cocoanut oil fatty'acids dissolved in an organic solvent, aqueous dispersions may be used which can readily be prepared by adding the zinc soap,
with vigorous agitation to water containing small amounts of morpholine, benzylamine, pyridine, ethanolamine', dimethylamine' and the like. In this manner a concentrated paste, containing approximately 60-50% of the zinc soap is obtained which can, readily-be dispersed in water inst prior to use. A suitable dispersing agent,
. such as .Alphasol, a commercial product, may
be incorporated to render the dispersion more stable.
The materials treated with 2-6% dispersion of zinc soap in water show excellent waterproofing characteristics, and remain substantially waterprooi in dry cleaning. Moreover,- fabrics so treated are substantially mothproof.
Solubilized zinc soap of cocoanut oil may be used as an insect repellent to treat and protect fabrics that are normally attacked by moths and other insects. 1
Other uses of the solubilized product are as an activator in connectionxwith vulcanization accelerators, in rubber cements or natural or artificially-prepared latices of rubber as a water repellent or mildew preventative, in paints and varnishes, in lubricating oils (to impart oillness to extreme pressure lubricants), etc., and as a mildew preventative in textile and the like. I Having thus described my invention, what I claim and desire to protect by Letters Patent is: 1. Zinc soap of cocoanut oil fatty acids com.- bined with an amine selected from the class consisting of morpholine, monobenzylamine, pyridine, ethylene diamine, piperidine, monocyclohexylamine, monoethanolamine. diethanolamine, triethanolamine, triamylamine.
' 2. Zinc soap or cocoanut oil combined with inorph'oline.
3. Zinc soap of cocoanut oil combined with a mix .consisting of monobenzylamine and dibenzylamine.
. 4. As an improved moth-proofing agent, a zinc soap of cocoanut oil combined with an amine selected from the class consisting of morpholine. monobenzylamine pyridlne, ethylene diamine,
piperidine, monocyclohexylamine, monoethanolamine, diethanolamine, triethanolamine, triamylamine.
5. A process of water-proofing and moth-proo ing textile material which comprises treating the same with a zinc soap of cocoanut oil combined with an amine selected from the class consisting of morpholine, monobenzylamine, pyridine, ethylene diamine, piperidine, monocyclohexylamine. monoethanolamine, diethanolamine, triethanolamine, triamylamine.
6. Textile material which has been treated with the composition set forth in claim 1.
7. Textile material which 'haspbeen treated with a zinc soap oi cocoanut oil fatty acids in combination with diethanolamine. I 8. Zinc soap of cocoanut oil combined with dlethanolamine.
' WILLIAM P. ran HORST.
US267519A 1939-04-12 1939-04-12 Composition of matter Expired - Lifetime US2243544A (en)

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2588428A (en) * 1945-04-02 1952-03-11 Goodrich Co B F Complex amine products with dialkyl zinc dithiocarbamates as pesticides
US2802811A (en) * 1953-11-02 1957-08-13 Vanderbilt Co R T Chloroprene stabilized with a mixture of zinc dimethyl dithiocarbamate and the zinc salt of mercaptobenzothiazole
DE1058248B (en) * 1952-12-15 1959-05-27 Dehydag Gmbh Process for masticating and softening rubber
US2976206A (en) * 1957-01-29 1961-03-21 Pittsburgh Plate Glass Co Pesticidal composition
WO2010057743A3 (en) * 2008-11-20 2010-10-21 Unilever Nv Method and composition for treating a fabric

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2588428A (en) * 1945-04-02 1952-03-11 Goodrich Co B F Complex amine products with dialkyl zinc dithiocarbamates as pesticides
DE1058248B (en) * 1952-12-15 1959-05-27 Dehydag Gmbh Process for masticating and softening rubber
US2802811A (en) * 1953-11-02 1957-08-13 Vanderbilt Co R T Chloroprene stabilized with a mixture of zinc dimethyl dithiocarbamate and the zinc salt of mercaptobenzothiazole
US2976206A (en) * 1957-01-29 1961-03-21 Pittsburgh Plate Glass Co Pesticidal composition
WO2010057743A3 (en) * 2008-11-20 2010-10-21 Unilever Nv Method and composition for treating a fabric

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