US2145214A - Parasiticide - Google Patents
Parasiticide Download PDFInfo
- Publication number
- US2145214A US2145214A US2145214DA US2145214A US 2145214 A US2145214 A US 2145214A US 2145214D A US2145214D A US 2145214DA US 2145214 A US2145214 A US 2145214A
- Authority
- US
- United States
- Prior art keywords
- guanidine
- salt
- mothproofing
- composition containing
- dixylyl
- 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
- 230000000590 parasiticidal Effects 0.000 title 2
- 239000002297 parasiticide Substances 0.000 title 2
- 239000000203 mixture Substances 0.000 description 30
- 229960004198 Guanidine Drugs 0.000 description 26
- ZRALSGWEFCBTJO-UHFFFAOYSA-N guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 26
- 239000002657 fibrous material Substances 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- -1 fatty acid salts Chemical class 0.000 description 12
- 239000011780 sodium chloride Substances 0.000 description 12
- 150000002357 guanidines Chemical class 0.000 description 10
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 10
- 239000000463 material Substances 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- 239000003208 petroleum Substances 0.000 description 6
- 210000002268 Wool Anatomy 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 4
- 125000005027 hydroxyaryl group Chemical group 0.000 description 4
- NRZWYNLTFLDQQX-UHFFFAOYSA-N p-tert-Amylphenol Chemical compound CCC(C)(C)C1=CC=C(O)C=C1 NRZWYNLTFLDQQX-UHFFFAOYSA-N 0.000 description 4
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 2
- XZMCDFZZKTWFGF-UHFFFAOYSA-N carbodiimide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000012262 resinous product Substances 0.000 description 2
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
- A61K31/155—Amidines (), e.g. guanidine (H2N—C(=NH)—NH2), isourea (N=C(OH)—NH2), isothiourea (—N=C(SH)—NH2)
Definitions
- This invention relates to a composition for treating fibrous materials such as wool against attack by moths and constitutes an improvement upon the subject matter of U. S. Patent 1,915,922. y
- a suitable solvent such as a petroleum fraction and specifically naphtha.
- the wool or other fibrous material to be protected is then treated with this solution, and the solvent permitted to evaporate.
- the fibrous material has a greasy appearance or is greasy to the touch. This is due to the fact that the guanidine is used as a fatty acid salt.
- the principal object of the present invention is to take advantage of the mothproofing qualities of the di-substituted guanidines using, however, salts thereof which are not subject to the above objection but which, at the same time, are as good or better for the purpose specified.
- the phenolic salts of the di-substituted guanidines are particularly effective as mothproofing agents. Any di-substituted guanidine may be used as the base for the composition and particularly the diaryl compounds. Dixylyl guanidine is preferred.
- Any of the hydroxy aryl salts of the di-substituted guanidines may be used for this purpose or the hydroxy alkyl aryl salts thereof.
- a para tertiary alkyl phenolic salt such as the para tertiary amyl phenolic salt of 40 dimlyl guanidine because ofqtheir greater efllciency.
- Whichever salt is used it is preferred to dissolve this material in a petroleum fraction such as naphtha or other solvent which may be readily evaporated.
- a mothproofing composition containing a phenolic salt of a diaryl guanidine containing a phenolic salt of a diaryl guanidine.
- a mothproofing composition containing hydroxy aryl salt of a diaryl guanidine 4.
- a mothproofing composition containing a para tertiary alkyl phenolic salt of a diaryl guan- 3o idine containing a para tertiary alkyl phenolic salt of a diaryl guan- 3o idine.
- a mothproofing composition .containing a para tertiary amyl phenolic salt of a diaryl guanidine.
- I 40 10 A mothproofing composition containing a phenolic salt of a disubstituted guanidine in a volatile solvent.
- a mothproofing composition containing a para tertiary amyl phenolic salt of dixylyl guani- 45 dine in a volatile solvent containing a para tertiary amyl phenolic salt of dixylyl guani- 45 dine in a volatile solvent.
- a mothproofing composition containing a para tertiary alkyl phenolic salt of dixylyl guani dine in a volatile solvent containing a para tertiary alkyl phenolic salt of dixylyl guani dine in a volatile solvent.
Description
Patented Jan. 24, 1939 rmsmcmn David Walker Jayne, Jr., Elizabeth, N. 1., assignor to American Cyanamid Company, New York, N. Y., a corporation of Maine No Drawing. Application March 3, 1936, Serial No. 66,797
12 Claims. (Cl. 16737) This invention relates to a composition for treating fibrous materials such as wool against attack by moths and constitutes an improvement upon the subject matter of U. S. Patent 1,915,922. y In that patent, there has been proposed the treatment of fibrous material for the stated purpose with fatty acid salts of xii-substituted guanidines, specifically dixylyl guanidines. The procedure there proposed is to dissolve such material in a suitable solvent, such as a petroleum fraction and specifically naphtha. The wool or other fibrous material to be protectedis then treated with this solution, and the solvent permitted to evaporate.
When treating fibrous material with. the material of the above patent as above set forth, it.
has been found that in some instances the fibrous material has a greasy appearance or is greasy to the touch. This is due to the fact that the guanidine is used as a fatty acid salt.
The principal object of the present invention, therefore, is to take advantage of the mothproofing qualities of the di-substituted guanidines using, however, salts thereof which are not subject to the above objection but which, at the same time, are as good or better for the purpose specified.
It has been found that the phenolic salts of the di-substituted guanidines are particularly effective as mothproofing agents. Any di-substituted guanidine may be used as the base for the composition and particularly the diaryl compounds. Dixylyl guanidine is preferred.
$ Any of the hydroxy aryl salts of the di-substituted guanidines may be used for this purpose or the hydroxy alkyl aryl salts thereof. I particularly prefer a para tertiary alkyl phenolic salt such as the para tertiary amyl phenolic salt of 40 dimlyl guanidine because ofqtheir greater efllciency. Whichever salt is used, it is preferred to dissolve this material in a petroleum fraction such as naphtha or other solvent which may be readily evaporated.-
As a specific example of preparation of the materlal, three parts of dixylyl guanidine and two parts of para tertiary amyl phenol are mixed together and heated to to C. The mixture is then stirred at this temperatureuntil a clear 50 homogeneous resinous product is obtained. This product is the para tertiary amyl phenol salt of dixylyl guanidine. Ten parts of this material are then dissolved in 8 parts of monobutyl ether of ethylene glycol and this solution diluted with 182 parts of petroleum naphtha to give a solution to be used for mothproofing containing 5% 5 of the guanidine salt. This solution should then be applied to the fibrous material in the proportion of approximately 1 pound of the solution to 20 to 40 pounds of the fibrous material to give desirable mothproofing protection. The solvents 10 are then allowed to evaporate.
While the invention has been shown and described with reference to certain specific embodiments, it is to be understood that the invention is not to be limited thereto but is to be construed l5 broadly and limited only by the scope of the claims.
I claim:
1. A mothproofing composition containing a phenolic salt of a disubstituted guanidine. 20
2. A mothproofing composition containing a phenolic salt of a diaryl guanidine.
3. A mothproofing composition containing a phenolic salt of a dixylyl guanidine.
4. A mothproofing composition containing hydroxy aryl salt of a diaryl guanidine.
5. A mothproofing composition containing a hydroxy alkyl aryl salt of a diaryl guanidine.
6. A mothproofing composition containing a para tertiary alkyl phenolic salt of a diaryl guan- 3o idine.
7. A mothproofing composition .containing a para tertiary amyl phenolic salt of a diaryl guanidine.
8. A mothproofing composition containing a 35 para tertiary alkyl phenolic salt of a dixylyl guanidine.
9. A mothproofing composition containing a para tertiary amyl phenolic salt of dixylyl guanidine. I 40 10. A mothproofing composition containing a phenolic salt of a disubstituted guanidine in a volatile solvent.
11. A mothproofing composition containing a para tertiary amyl phenolic salt of dixylyl guani- 45 dine in a volatile solvent.
12. A mothproofing composition containing a para tertiary alkyl phenolic salt of dixylyl guani dine in a volatile solvent.
navm warm JAYNE, JR.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2145214A true US2145214A (en) | 1939-01-24 |
Family
ID=3429944
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US2145214D Expired - Lifetime US2145214A (en) | Parasiticide |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2145214A (en) |
Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2499226A (en) * | 1944-11-23 | 1950-02-28 | American Cyanamid Co | Resinous aromatic acid salts of a guanidine as mothproofers |
| US5262568A (en) * | 1990-03-02 | 1993-11-16 | State Of Oregon | Tri- and tetra-substituted guanidines and their use as excitatory amino acid antagonists |
| US5312840A (en) * | 1986-07-10 | 1994-05-17 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education | Substituted guanidines having high binding to the sigma receptor and the use thereof |
| US5336689A (en) * | 1990-03-02 | 1994-08-09 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And The University Of Oregon | Tri- and tetra-substituted guanidines and their use as excitatory amino acid antagonists |
| US5385946A (en) * | 1986-07-10 | 1995-01-31 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And The University Of Oregon | Method for treating hypertension with disubstituted granidine compounds |
| US5403861A (en) * | 1991-02-08 | 1995-04-04 | Cambridge Neuroscience, Inc. | Substituted guanidines and derivatives thereof as modulators of neurotransmitter release and novel methodology for identifying neurotransmitter release blockers |
| US5574070A (en) * | 1990-05-25 | 1996-11-12 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University | Substituted guanidines having high binding to the sigma receptor and the use thereof |
| US5741661A (en) * | 1991-02-08 | 1998-04-21 | Cambridge Neuroscience, Inc. | Substituted guanidines and derivatives thereof as modulators of neurotransmitter release and novel methodology for identifying neurotransmitter release blockers |
| US5847006A (en) * | 1991-02-08 | 1998-12-08 | Cambridge Neuroscience, Inc. | Therapeutic guanidines |
| US5955507A (en) * | 1993-11-23 | 1999-09-21 | Cambridge Neuroscience, Inc. | Therapeutic substituted guanidines |
| US6143791A (en) * | 1994-02-03 | 2000-11-07 | Cambridge Neuroscience, Inc. | Therapeutic guanidines |
| US6147063A (en) * | 1993-05-27 | 2000-11-14 | Cambridge Neuroscience, Inc. | Therapeutic substituted guanidines |
| US6174924B1 (en) | 1994-02-03 | 2001-01-16 | Cambridge Neuroscience, Inc. | Therapeutic guanidines |
| US6251948B1 (en) | 1990-03-02 | 2001-06-26 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And The University Of Oregon | Tri-and tetra-substituted guanidines and their use as excitatory amino acid antagonists |
| US6787569B1 (en) | 1994-02-03 | 2004-09-07 | Cambridge Neuroscience, Inc. | Therapeutic guanidines |
| US7351743B1 (en) | 1994-02-03 | 2008-04-01 | Wyeth | Therapeutic guanidines |
-
0
- US US2145214D patent/US2145214A/en not_active Expired - Lifetime
Cited By (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2499226A (en) * | 1944-11-23 | 1950-02-28 | American Cyanamid Co | Resinous aromatic acid salts of a guanidine as mothproofers |
| US5478863A (en) * | 1986-07-10 | 1995-12-26 | State Of Oregon, Oregon Health Sciences University Of Oregon | Substituted guanidines having high binding to the sigma receptor and the use thereof |
| US5312840A (en) * | 1986-07-10 | 1994-05-17 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education | Substituted guanidines having high binding to the sigma receptor and the use thereof |
| US5604228A (en) * | 1986-07-10 | 1997-02-18 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University | Substituted guanidines having high binding to the sigma receptor and the use thereof |
| US5385946A (en) * | 1986-07-10 | 1995-01-31 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And The University Of Oregon | Method for treating hypertension with disubstituted granidine compounds |
| US5502255A (en) * | 1986-07-10 | 1996-03-26 | State Of Oregon Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And The University Of Oregon | Substituted guanidines having high binding to the sigma receptor and the use thereof |
| US5336689A (en) * | 1990-03-02 | 1994-08-09 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And The University Of Oregon | Tri- and tetra-substituted guanidines and their use as excitatory amino acid antagonists |
| US6251948B1 (en) | 1990-03-02 | 2001-06-26 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And The University Of Oregon | Tri-and tetra-substituted guanidines and their use as excitatory amino acid antagonists |
| US5559154A (en) * | 1990-03-02 | 1996-09-24 | Oregon State Board Of Higher Education | Tri- and tetra-substituted guanidines and their use as excitatory amino acid antagonists |
| US5637622A (en) * | 1990-03-02 | 1997-06-10 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And The University Of Oregon | Tri- and tetra-substituted guanidines and their use as excitatory amino acid antagonists |
| US5798390A (en) * | 1990-03-02 | 1998-08-25 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And The University Of Oregon | Tri- and tetra-substituted guanidines and their use as excitatory amino acid antagonists |
| US5767162A (en) * | 1990-03-02 | 1998-06-16 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And The University Of Oregon | Tri-and tetra-substituted guanidines and their use as excitatory amino acid antagonists |
| US5262568A (en) * | 1990-03-02 | 1993-11-16 | State Of Oregon | Tri- and tetra-substituted guanidines and their use as excitatory amino acid antagonists |
| US5574070A (en) * | 1990-05-25 | 1996-11-12 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University | Substituted guanidines having high binding to the sigma receptor and the use thereof |
| US5677348A (en) * | 1991-02-08 | 1997-10-14 | Cambridge Neuroscience, Inc. | Substituted aminoguanidines and methods of use thereof |
| US5741661A (en) * | 1991-02-08 | 1998-04-21 | Cambridge Neuroscience, Inc. | Substituted guanidines and derivatives thereof as modulators of neurotransmitter release and novel methodology for identifying neurotransmitter release blockers |
| US5670519A (en) * | 1991-02-08 | 1997-09-23 | Cambridge Neuroscience, Inc. | Acenaphthyl-substituted guanidines and methods of use thereof |
| US5672608A (en) * | 1991-02-08 | 1997-09-30 | Cambridge Neuroscience, Inc. | Acenaphthyl substituted guanidines and methods of use thereof |
| US5637623A (en) * | 1991-02-08 | 1997-06-10 | Cambridge Neuroscience, Inc. | Substituted adamantyl guanidines and methods of use there of |
| US5681861A (en) * | 1991-02-08 | 1997-10-28 | Cambridge Neuroscience, Inc. | Aminoguanidines and methods of use of same |
| US5686495A (en) * | 1991-02-08 | 1997-11-11 | Cambridge Neuroscience, Inc. | Substituted hydrazinedicarboximidamides and methods of use thereof |
| US6071969A (en) * | 1991-02-08 | 2000-06-06 | Cambridge Neuroscience, Inc. | Substituted aminoguanidines and methods of use thereof |
| US5622968A (en) * | 1991-02-08 | 1997-04-22 | Cambridge Neuroscience, Inc. | Acenaphthyl substituted guanidines and methods of use thereof |
| US5614630A (en) * | 1991-02-08 | 1997-03-25 | Cambridge Neuroscience, Inc. | Acenaphthyl substituted guanidines and methods of use thereof |
| US5837737A (en) * | 1991-02-08 | 1998-11-17 | Cambridge Neuroscience, Inc. | Hydrazinedicarboximidamide compounds and pharmaceutical composition comprising same |
| US5847006A (en) * | 1991-02-08 | 1998-12-08 | Cambridge Neuroscience, Inc. | Therapeutic guanidines |
| US5403861A (en) * | 1991-02-08 | 1995-04-04 | Cambridge Neuroscience, Inc. | Substituted guanidines and derivatives thereof as modulators of neurotransmitter release and novel methodology for identifying neurotransmitter release blockers |
| US5652269A (en) * | 1991-02-08 | 1997-07-29 | Cambridge Neuroscience, Inc. | Substituted hydrazinecarboximidamides and methods of use thereof |
| US6147063A (en) * | 1993-05-27 | 2000-11-14 | Cambridge Neuroscience, Inc. | Therapeutic substituted guanidines |
| US6153604A (en) * | 1993-05-27 | 2000-11-28 | Cambridge Neuroscience, Inc. | Therapeutic substituted guanidines |
| US6013675A (en) * | 1993-11-23 | 2000-01-11 | Cambridge Neuroscience, Inc. | Therapeutic substituted guanidines |
| US6156741A (en) * | 1993-11-23 | 2000-12-05 | Cambridge Neuroscience, Inc. | Therapeutic substituted guanidines |
| US5955507A (en) * | 1993-11-23 | 1999-09-21 | Cambridge Neuroscience, Inc. | Therapeutic substituted guanidines |
| US6143791A (en) * | 1994-02-03 | 2000-11-07 | Cambridge Neuroscience, Inc. | Therapeutic guanidines |
| US6174924B1 (en) | 1994-02-03 | 2001-01-16 | Cambridge Neuroscience, Inc. | Therapeutic guanidines |
| US6288123B1 (en) | 1994-02-03 | 2001-09-11 | Cambridge Neurosciences, Inc. | Therapeutic guanidines |
| US6787569B1 (en) | 1994-02-03 | 2004-09-07 | Cambridge Neuroscience, Inc. | Therapeutic guanidines |
| US20070265348A1 (en) * | 1994-02-03 | 2007-11-15 | Scion Pharmaceuticals, Inc, A Delaware Corporation | Therapeutic guanidines |
| US7351743B1 (en) | 1994-02-03 | 2008-04-01 | Wyeth | Therapeutic guanidines |
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