US2243544A - Composition of matter - Google Patents
Composition of matter Download PDFInfo
- 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
- Authority
- 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
Links
- 239000000203 mixture Substances 0.000 title description 11
- 239000000344 soap Substances 0.000 description 33
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 29
- 239000011701 zinc Substances 0.000 description 29
- 229910052725 zinc Inorganic materials 0.000 description 29
- 239000003921 oil Substances 0.000 description 19
- 235000013162 Cocos nucifera Nutrition 0.000 description 18
- 244000060011 Cocos nucifera Species 0.000 description 18
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 150000001412 amines Chemical class 0.000 description 9
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 9
- 229920001971 elastomer Polymers 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 8
- 239000000463 material Substances 0.000 description 7
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 5
- 239000004744 fabric Substances 0.000 description 5
- 239000004753 textile Substances 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical compound C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 description 4
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 4
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 4
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 4
- OOHAUGDGCWURIT-UHFFFAOYSA-N n,n-dipentylpentan-1-amine Chemical compound CCCCCN(CCCCC)CCCCC OOHAUGDGCWURIT-UHFFFAOYSA-N 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 239000003350 kerosene Substances 0.000 description 3
- 238000004078 waterproofing Methods 0.000 description 3
- -1 -xylol Substances 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 239000003502 gasoline Substances 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- 239000005871 repellent Substances 0.000 description 2
- 230000002940 repellent Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 150000003751 zinc Chemical class 0.000 description 2
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 239000004568 cement Substances 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000005108 dry cleaning Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000000077 insect repellent Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 238000010058 rubber compounding Methods 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 239000011667 zinc carbonate Substances 0.000 description 1
- 229910000010 zinc carbonate Inorganic materials 0.000 description 1
- 235000004416 zinc carbonate Nutrition 0.000 description 1
- 229940098697 zinc laurate Drugs 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- GPYYEEJOMCKTPR-UHFFFAOYSA-L zinc;dodecanoate Chemical compound [Zn+2].CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O GPYYEEJOMCKTPR-UHFFFAOYSA-L 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
- 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
- D06M13/224—Esters 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.
Landscapes
- 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.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US267519A US2243544A (en) | 1939-04-12 | 1939-04-12 | Composition of matter |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US267519A US2243544A (en) | 1939-04-12 | 1939-04-12 | Composition of matter |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2243544A true US2243544A (en) | 1941-05-27 |
Family
ID=23019129
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US267519A Expired - Lifetime US2243544A (en) | 1939-04-12 | 1939-04-12 | Composition of matter |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2243544A (en) |
Cited By (5)
| 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 |
-
1939
- 1939-04-12 US US267519A patent/US2243544A/en not_active Expired - Lifetime
Cited By (5)
| 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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