US3443010A - Composition and methods for rendering absorbent materials fungicidal comprising an aqueous solution of borax/and the bis(tri-n-propyltin) diammonium chloride of a tri-polyoxyethylated n-alkyl trimethylene diamine - Google Patents
Composition and methods for rendering absorbent materials fungicidal comprising an aqueous solution of borax/and the bis(tri-n-propyltin) diammonium chloride of a tri-polyoxyethylated n-alkyl trimethylene diamine Download PDFInfo
- Publication number
- US3443010A US3443010A US504112A US3443010DA US3443010A US 3443010 A US3443010 A US 3443010A US 504112 A US504112 A US 504112A US 3443010D A US3443010D A US 3443010DA US 3443010 A US3443010 A US 3443010A
- Authority
- US
- United States
- Prior art keywords
- tri
- fungicidal
- borax
- propyltin
- polyoxyethylated
- 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
- 230000000855 fungicidal effect Effects 0.000 title description 13
- 229910021538 borax Inorganic materials 0.000 title description 11
- 239000004328 sodium tetraborate Substances 0.000 title description 11
- 235000010339 sodium tetraborate Nutrition 0.000 title description 11
- -1 bis(tri-n-propyltin) diammonium chloride Chemical compound 0.000 title description 9
- 239000000463 material Substances 0.000 title description 9
- 230000002745 absorbent Effects 0.000 title description 8
- 239000002250 absorbent Substances 0.000 title description 8
- 239000007864 aqueous solution Substances 0.000 title description 6
- 239000000203 mixture Substances 0.000 title description 6
- 238000000034 method Methods 0.000 title description 5
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Natural products NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 title description 3
- 238000009877 rendering Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 description 11
- 239000000243 solution Substances 0.000 description 9
- 239000004215 Carbon black (E152) Substances 0.000 description 8
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 8
- 239000004327 boric acid Substances 0.000 description 8
- 229930195733 hydrocarbon Natural products 0.000 description 8
- 150000002430 hydrocarbons Chemical class 0.000 description 8
- 239000002023 wood Substances 0.000 description 8
- 239000000758 substrate Substances 0.000 description 7
- 241000233866 Fungi Species 0.000 description 6
- 150000001639 boron compounds Chemical class 0.000 description 6
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 239000007853 buffer solution Substances 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 150000003839 salts Chemical group 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 2
- 235000011613 Pinus brutia Nutrition 0.000 description 2
- 241000018646 Pinus brutia Species 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000004806 packaging method and process Methods 0.000 description 2
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 2
- 239000011122 softwood Substances 0.000 description 2
- 150000003606 tin compounds Chemical class 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241001459693 Dipterocarpus zeylanicus Species 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 239000003429 antifungal agent Substances 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 235000015241 bacon Nutrition 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000011111 cardboard Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 230000002070 germicidal effect Effects 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 238000003359 percent control normalization Methods 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
- B27K—PROCESSES, APPARATUS OR SELECTION OF SUBSTANCES FOR IMPREGNATING, STAINING, DYEING, BLEACHING OF WOOD OR SIMILAR MATERIALS, OR TREATING OF WOOD OR SIMILAR MATERIALS WITH PERMEANT LIQUIDS, NOT OTHERWISE PROVIDED FOR; CHEMICAL OR PHYSICAL TREATMENT OF CORK, CANE, REED, STRAW OR SIMILAR MATERIALS
- B27K3/00—Impregnating wood, e.g. impregnation pretreatment, for example puncturing; Wood impregnation aids not directly involved in the impregnation process
- B27K3/52—Impregnating agents containing mixtures of inorganic and organic compounds
-
- 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
- A01N59/00—Biocides, pest repellants or attractants, or plant growth regulators containing elements or inorganic compounds
- A01N59/14—Boron; Compounds thereof
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
- B27K—PROCESSES, APPARATUS OR SELECTION OF SUBSTANCES FOR IMPREGNATING, STAINING, DYEING, BLEACHING OF WOOD OR SIMILAR MATERIALS, OR TREATING OF WOOD OR SIMILAR MATERIALS WITH PERMEANT LIQUIDS, NOT OTHERWISE PROVIDED FOR; CHEMICAL OR PHYSICAL TREATMENT OF CORK, CANE, REED, STRAW OR SIMILAR MATERIALS
- B27K3/00—Impregnating wood, e.g. impregnation pretreatment, for example puncturing; Wood impregnation aids not directly involved in the impregnation process
- B27K3/16—Inorganic impregnating agents
- B27K3/163—Compounds of boron
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
- B27K—PROCESSES, APPARATUS OR SELECTION OF SUBSTANCES FOR IMPREGNATING, STAINING, DYEING, BLEACHING OF WOOD OR SIMILAR MATERIALS, OR TREATING OF WOOD OR SIMILAR MATERIALS WITH PERMEANT LIQUIDS, NOT OTHERWISE PROVIDED FOR; CHEMICAL OR PHYSICAL TREATMENT OF CORK, CANE, REED, STRAW OR SIMILAR MATERIALS
- B27K3/00—Impregnating wood, e.g. impregnation pretreatment, for example puncturing; Wood impregnation aids not directly involved in the impregnation process
- B27K3/34—Organic impregnating agents
Definitions
- the present invention relates to methods for treating absorbent substrates to inhibit the growth of mold fungi thereon, and to the treating agents used.
- the invention relates particularly to the anti-fungal treatment of wood.
- an inorgano tin halide (R) SnX, wherein R and X have been defined, are reacted with an amine wherein: (A) R is a long chain fatty hydrocarbon, R" is (CH CH O) H, and x+y is about 10; (B) R is a long chain fatty hydrocarbon, R" is (CH CH O) H and x+z is about 50; (C) R' is a long chain fatty hydrocarbon, R" is CHzCH CHnN CHQGHZmuH and xi-l-m +n is about 10; (D) wherein R is a long chain fatty hydrocarbon, R" is H2O HzCHz-N-Sl1(R) a X- H2CH20)u x+p+q is about 10, and R is lower alkyl; and (E) wherein R is -(CH CH O),H, R" is Riv -CHgCHzCH2N (CH'zCHzOhH
- the quaternary ammonium compounds are highly soluble in water, which facilitates their application to absorbent materials 3,443,010 Patented May 6, 1969 from solution. Because they are in salt form, they appear to be much more tenaciously held to treated substrates such as wood than are electrically neutral compounds, and thus are of particular usefulness for the treatment of materials used for the packaging of food, where transfer of the fungicidal material from the package to its contents is preferably minimized.
- fungicidal and germicidal activities of the compounds of the copending application are as good or better than those of any materials heretofore known in the art for the treatment of wood, it has now been discovered that the fungicidal activity of those compounds can be surprisingly increased by employing them in combination with an inorganic boron compound such as borax, boric acid, or buffer solutions comprising boric acid in combination with a soluble borate.
- an inorganic boron compound such as borax, boric acid, or buffer solutions comprising boric acid in combination with a soluble borate.
- borax has been used in the past as an anti-fungal agent, particularly in the treatment of wood, it has heretofore been believed that fungus control with the material was due to the creation of an alkaline pH unfavorable to the growth of fungi.
- boron containing compounds used in conjunction with the organotin quaternary ammonium salts already discussed show fungicidal activity not only in alkaline solutions, such as of borax, but also in acidic boric acid solutions and in acid, neutral and alkaline buffer solutions of boric acid and a borate.
- the fungicidal effects observed when treating a substrate with an organotin compound in combination with an inorganic boron compound are not merely additive, but show an unexpected enhanced activity greater than the combined activities of the individual components when used alone. That is, synergism is observed.
- the tin compound is suitably present in concentrations of from about 0.04 percent by weight to about 0.2 percent by weight, preferably about -0.1 percent by weight, the latter corresponding roughly to a concentration of one ounce per ten gallons of water.
- the solutions just described are used to impregnate an absorbent material to which fungicidal properties are to be imparted, commonly wood but also including cardboard, paper, textiles, etc.
- the solutions are effective when used with all types of woods, wet or dry, but are of particular utility for the treatment of soft woods such as pine used in the-construction of wirebound boxes for packaging produce and other foodstuffs. Because of the need for flexibility in soft wood slats used in such wirebound boxes, the slats usually contain a high water content and are highly susceptible to attack by fungi which cause an undesirable discoloration of the wood.
- Groups of fifty slats were selected at random and submerged individually for a period of fifteen seconds in treating solutions of a composition indicated below in Table I. A control group of fifty slats was left untreated. Each group of slats was then. bulk piled on a wooden pallet in the random fashion typical of production handling. The pallet of slats was stored at mill conditions for a period of five weeks, and hence was exposed to airborne spores present in the mill. The proportion of the total surface area of each slat on which mold fungi had developed was then estimated visually, as reported in the following Table.
- the organotin compound in each case is the bis(tri-n-propyltin) diammonium chloride of a tri-polyoxyethylated N- alkyltrimethylene diamine, i.e. the compound wherein R' is a long chain fatty hydrocarbon and x+p+q is about 10.
- polyoxyethylated N-alkyl trimethylene diamine of the formula (CHzCHzOhH (CH OHzOMH [RNCHzCH CHzN-Sn(C;H1)al 201- SD(C3H7)3 H2CH2O)QH wherein R is a long chain fatty hydrocarbon and x+17+q is about 10.
- a composition adaptable to the treatment of absorbent substrates to render them fungicidal said composition being an aqueous solution of borax in an amount from about 0.5 percent by weight to about 3.5 percent by weight and about 0.1 percent by weight of the bis(trin-propyltin) diammonium chloride of a tri-polyoxyethylated N-alkyl trimethylene diamine of the formula wherein R is a long chain fatty hydrocarbon and x+p+q is about 10.
- boric acid/borax mixtures 1n which the 2317:9555 8/1950 Bacon 167 38.5 weight ratio of acid to Salt is 011 have 3 P 0f Y 3 307 039 5 19 2
- Mazur 2 429 7 reducing the ratio to 10:1, 5:1, or 2:1
- buffer solutions 3,305,442 2/1967 Nishimoto 167 386 respectively having a pH of 7.20, 7.50, or 7.90 can be prepared.
- the method of treating an absorbent substrate to render it fungicidal which comprises impregnating said substrate with an aqueous solution comprising borax in an amount from about 0.5 percent by Weight to about 3.5 percent by weight and about 0.1 percent by Weight of the bis(tri-n-propyltin) diammonium chloride of a tri- OTHER REFERENCES FRANK CACCLAPAGLIA, 111., Primary Examiner.
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Chemical & Material Sciences (AREA)
- Inorganic Chemistry (AREA)
- Forests & Forestry (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Health & Medical Sciences (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Chemical And Physical Treatments For Wood And The Like (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Discharge Lamp (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US50411265A | 1965-10-23 | 1965-10-23 |
Publications (1)
Publication Number | Publication Date |
---|---|
US3443010A true US3443010A (en) | 1969-05-06 |
Family
ID=24004891
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US504112A Expired - Lifetime US3443010A (en) | 1965-10-23 | 1965-10-23 | Composition and methods for rendering absorbent materials fungicidal comprising an aqueous solution of borax/and the bis(tri-n-propyltin) diammonium chloride of a tri-polyoxyethylated n-alkyl trimethylene diamine |
Country Status (8)
Country | Link |
---|---|
US (1) | US3443010A (enrdf_load_stackoverflow) |
DE (1) | DE1567182A1 (enrdf_load_stackoverflow) |
ES (1) | ES332618A1 (enrdf_load_stackoverflow) |
GB (1) | GB1135459A (enrdf_load_stackoverflow) |
IL (1) | IL26667A (enrdf_load_stackoverflow) |
NL (1) | NL6614955A (enrdf_load_stackoverflow) |
NO (1) | NO119555B (enrdf_load_stackoverflow) |
SE (1) | SE314554B (enrdf_load_stackoverflow) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4128429A (en) * | 1977-01-06 | 1978-12-05 | Sankyo Organic Chemicals Company Limited | Antifouling quaternary halide salts containing a triorganotin ether moiety |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3706237A1 (de) * | 1987-02-26 | 1988-09-08 | Lentia Gmbh | Kaeltestabile, in wasser dispergierbare fluessige konzentratformulierung |
US5087457A (en) * | 1990-01-12 | 1992-02-11 | Buckman Laboratories International, Inc. | Synergistic microbicides containing ionene polymers and borates for the control of fungi on surfaces |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2041655A (en) * | 1933-11-24 | 1936-05-19 | Celcure Corp | Wood treating preparation |
US2268387A (en) * | 1939-04-07 | 1941-12-30 | Du Pont | Presservation of wood |
US2517958A (en) * | 1948-06-09 | 1950-08-08 | Wyandotte Chemicals Corp | Inorganic composition for inhibiting sap stain |
US3305442A (en) * | 1963-11-26 | 1967-02-21 | Yoshitomi Pharmaceutical | Organic tin sulfamates and wood preservatives using the same |
US3307039A (en) * | 1963-03-04 | 1967-02-28 | Siemens Ag Albis | Gap pattern for chopper of radiation search system |
-
1965
- 1965-10-23 US US504112A patent/US3443010A/en not_active Expired - Lifetime
-
1966
- 1966-10-10 IL IL26667A patent/IL26667A/xx unknown
- 1966-10-12 GB GB45676/66A patent/GB1135459A/en not_active Expired
- 1966-10-19 NO NO165216A patent/NO119555B/no unknown
- 1966-10-21 NL NL6614955A patent/NL6614955A/xx unknown
- 1966-10-21 SE SE14446/66A patent/SE314554B/xx unknown
- 1966-10-22 ES ES0332618A patent/ES332618A1/es not_active Expired
- 1966-10-24 DE DE19661567182 patent/DE1567182A1/de active Pending
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2041655A (en) * | 1933-11-24 | 1936-05-19 | Celcure Corp | Wood treating preparation |
US2268387A (en) * | 1939-04-07 | 1941-12-30 | Du Pont | Presservation of wood |
US2517958A (en) * | 1948-06-09 | 1950-08-08 | Wyandotte Chemicals Corp | Inorganic composition for inhibiting sap stain |
US3307039A (en) * | 1963-03-04 | 1967-02-28 | Siemens Ag Albis | Gap pattern for chopper of radiation search system |
US3305442A (en) * | 1963-11-26 | 1967-02-21 | Yoshitomi Pharmaceutical | Organic tin sulfamates and wood preservatives using the same |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4128429A (en) * | 1977-01-06 | 1978-12-05 | Sankyo Organic Chemicals Company Limited | Antifouling quaternary halide salts containing a triorganotin ether moiety |
Also Published As
Publication number | Publication date |
---|---|
NO119555B (enrdf_load_stackoverflow) | 1970-06-01 |
NL6614955A (enrdf_load_stackoverflow) | 1967-04-24 |
IL26667A (en) | 1970-09-17 |
GB1135459A (en) | 1968-12-04 |
SE314554B (enrdf_load_stackoverflow) | 1969-09-08 |
ES332618A1 (es) | 1967-12-01 |
DE1567182A1 (de) | 1970-08-06 |
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