CA1061675A - Antimicrobial cleaning compositions - Google Patents
Antimicrobial cleaning compositionsInfo
- Publication number
- CA1061675A CA1061675A CA267,952A CA267952A CA1061675A CA 1061675 A CA1061675 A CA 1061675A CA 267952 A CA267952 A CA 267952A CA 1061675 A CA1061675 A CA 1061675A
- Authority
- CA
- Canada
- Prior art keywords
- accordance
- water
- weight
- solution
- glycol
- 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
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/48—Medical, disinfecting agents, disinfecting, antibacterial, germicidal or antimicrobial compositions
Abstract
ABSTRACT OF THE DISCLOSURE
Aqueous solutions containing 5-chloro-2-(2,4-dichloro-phenoxy)phenol, tetrasodium ethylenediamine tetraacetate, or tri-sodium nitrilotriacetate, selected anionic surfactants and glycol solvent. The solutions are antimicrobial cleaning compositions especially useful for the bathroom.
Aqueous solutions containing 5-chloro-2-(2,4-dichloro-phenoxy)phenol, tetrasodium ethylenediamine tetraacetate, or tri-sodium nitrilotriacetate, selected anionic surfactants and glycol solvent. The solutions are antimicrobial cleaning compositions especially useful for the bathroom.
Description
. _ _ _ . . . _ _ .
- This invention relates to antimicrobial solutions, and more particularly to antimicrobial aqueous solutions useful as bathroom cleaner compositions.
one of the more difficult areas of the home to clean is the ba-throom where a useful cleaner should not only be effective in removing unsightly soap scum, but should also be germicidal for use in and around the shower, toilet bowl and wash basin. ~
i The present invention provides an aqueous solution hav- ~ -ing superior properties for removing soap scum and also for killing -fungi, such as athlete's foot fungus, mildew and black mold as well ;
as numerous germs. Thus, the present compositions are useful in cleaning, deodorizing and disinfecting bathroom showers, toilet bowls and wash basins. ~;
The aqueous solutions of this invention contain three necessary ingredients in specific amounts. Such solutions com- -prise, by weight, about 0.05 to 0.5% of 5-chloro-2-(2,4-dichloro~
phenoxy)phenol, about 3 to 15% of trisodium nitrilotriacetate or tetrasodium ethylenediamine tetraacetate, about 0.5 to 4% of an anionic surfactant and optionally up to about 2~/o ~such as about 1 to 12%) of a water-miscible glycol solvent, wherein the anionic surfactant is either disodium dodecyldiphenylether disulfonate or sodium 2-ethyl-hexyl sulfate.
The 5-chloro 2-(2,4-dichlorophenoxy)phenol is commercial-ly available under the ~rademark Irgasan DP300. Disodium dodecyl-diphenylether disulfonate and sodium 2-ethylhexyl sulfate are also commercially available under the trademarks Dowfax 2Al and Tergi-tol 03, respectively. The water-miscible glycol solvent is pre-ferably hexylene glycol (2-methylpentane-2,4-diol) or a polyethyl- -~
ene glycol of the formula HO(CH2CH2O)n H, having a molecular weight of up to about 600. These polyethylene glycols are commercially ~ , available under the trademarks, Carbowax 200, Carbowax 400 and Car-bowax 600, in which 200, 400 and 600 indicate the average molecu-B` -1- ~ -.
. , , .. . .. . . , .. . .. . . .. .. . . ~.;
;
., . .. ,. . . , ~ ... .. . ., :- . ..
"r~ a~6~
lar weight of the compound.
The aqueous solutions may also contain minor amounts of other beneficial components such as a lower alkanol, ethyl and isopropyl alcohol, which may be included as a co-solvent and to ; enhance an-timicrobial activity. Other surfactants may also be present in addition to the required anionic surfactant. Further, it is preferred that the pH of the solution be in the range of about 10.0 to 10.5, and a small amount of acid such as acetic acid may be added for pH control. Also, small amounts of perfume and 10 dye may be included, if desired.
A preferred composition, according to this invention, contains about 0.06 to 0.2% of the 5-chloro-2-(2,4-dichlorophenoxy) phenol, about 5 to 10% of the tetrasodium ethylenediamine tetra-acetate or trisodium nitrilotriacetate, about 1 to 2% of the an- ;~
ionic surfactant, about 7 to 15% of the glycol solvent which is preferably hexylene glycol, and about 5% isopropyl alcohol. Such preferred solutions have a pH of about 10.3, adjusted by addition of acetic acid.
The compositions of this invention can be used to clean 20 and disinfect hard surfaces in the bathroom, such as fiberglass and porcelain showers and tubs, stainless steel, grouting, chrome, enamel woodwork and vanity tops. In using the compositions, -they are merely sprayed on-to the surface to be cleaned, allowing suf-ficient time to wet the surface thoroughly. The surface is then wiped with a damp cloth or sponge or rinsed off with water. If the surface is heavily soiled, it is preferred to allow about 2 to 5 minutes for the spray to penetrate and then use a non-scratch ing pad or brush before rinsing. Unsightly hard water dir-t and soap scum are readily removed and the cleaned surface is disin-fected. The compositions will kill germs and fungi such as ` ;
Staphylococcus aureus, Salmonella choleraesius, Pseudomonas aerug-inosa, Mycobacterium tuberculosis, Escherichia coli, Streptococcus
- This invention relates to antimicrobial solutions, and more particularly to antimicrobial aqueous solutions useful as bathroom cleaner compositions.
one of the more difficult areas of the home to clean is the ba-throom where a useful cleaner should not only be effective in removing unsightly soap scum, but should also be germicidal for use in and around the shower, toilet bowl and wash basin. ~
i The present invention provides an aqueous solution hav- ~ -ing superior properties for removing soap scum and also for killing -fungi, such as athlete's foot fungus, mildew and black mold as well ;
as numerous germs. Thus, the present compositions are useful in cleaning, deodorizing and disinfecting bathroom showers, toilet bowls and wash basins. ~;
The aqueous solutions of this invention contain three necessary ingredients in specific amounts. Such solutions com- -prise, by weight, about 0.05 to 0.5% of 5-chloro-2-(2,4-dichloro~
phenoxy)phenol, about 3 to 15% of trisodium nitrilotriacetate or tetrasodium ethylenediamine tetraacetate, about 0.5 to 4% of an anionic surfactant and optionally up to about 2~/o ~such as about 1 to 12%) of a water-miscible glycol solvent, wherein the anionic surfactant is either disodium dodecyldiphenylether disulfonate or sodium 2-ethyl-hexyl sulfate.
The 5-chloro 2-(2,4-dichlorophenoxy)phenol is commercial-ly available under the ~rademark Irgasan DP300. Disodium dodecyl-diphenylether disulfonate and sodium 2-ethylhexyl sulfate are also commercially available under the trademarks Dowfax 2Al and Tergi-tol 03, respectively. The water-miscible glycol solvent is pre-ferably hexylene glycol (2-methylpentane-2,4-diol) or a polyethyl- -~
ene glycol of the formula HO(CH2CH2O)n H, having a molecular weight of up to about 600. These polyethylene glycols are commercially ~ , available under the trademarks, Carbowax 200, Carbowax 400 and Car-bowax 600, in which 200, 400 and 600 indicate the average molecu-B` -1- ~ -.
. , , .. . .. . . , .. . .. . . .. .. . . ~.;
;
., . .. ,. . . , ~ ... .. . ., :- . ..
"r~ a~6~
lar weight of the compound.
The aqueous solutions may also contain minor amounts of other beneficial components such as a lower alkanol, ethyl and isopropyl alcohol, which may be included as a co-solvent and to ; enhance an-timicrobial activity. Other surfactants may also be present in addition to the required anionic surfactant. Further, it is preferred that the pH of the solution be in the range of about 10.0 to 10.5, and a small amount of acid such as acetic acid may be added for pH control. Also, small amounts of perfume and 10 dye may be included, if desired.
A preferred composition, according to this invention, contains about 0.06 to 0.2% of the 5-chloro-2-(2,4-dichlorophenoxy) phenol, about 5 to 10% of the tetrasodium ethylenediamine tetra-acetate or trisodium nitrilotriacetate, about 1 to 2% of the an- ;~
ionic surfactant, about 7 to 15% of the glycol solvent which is preferably hexylene glycol, and about 5% isopropyl alcohol. Such preferred solutions have a pH of about 10.3, adjusted by addition of acetic acid.
The compositions of this invention can be used to clean 20 and disinfect hard surfaces in the bathroom, such as fiberglass and porcelain showers and tubs, stainless steel, grouting, chrome, enamel woodwork and vanity tops. In using the compositions, -they are merely sprayed on-to the surface to be cleaned, allowing suf-ficient time to wet the surface thoroughly. The surface is then wiped with a damp cloth or sponge or rinsed off with water. If the surface is heavily soiled, it is preferred to allow about 2 to 5 minutes for the spray to penetrate and then use a non-scratch ing pad or brush before rinsing. Unsightly hard water dir-t and soap scum are readily removed and the cleaned surface is disin-fected. The compositions will kill germs and fungi such as ` ;
Staphylococcus aureus, Salmonella choleraesius, Pseudomonas aerug-inosa, Mycobacterium tuberculosis, Escherichia coli, Streptococcus
-2-~l~)6~
. ~ :
~oqenes Enterbacter aeroqenes, pro-teus mirabitis, athlete's foot fungus (Trycophyton men-tagrophytes), Candida albicans, and black mold such as Aspergillus niqer and prevent the re-growth of such organisms for at least 28 days.
The following are represen-tative examples of the anti-microbial compositions of this invention.
. .
% by weiqht hexylene glycol 10.0 10- 5-chloro-2-(2,4-dichlorophenoxy)phenol 0.1 sodium 2-ethylhexyl sulfate (40% active) ~.5 lauryl alcohol ether sulfate (Na salt) (30% active) 0.33 -tetrasodium EDTA (36% active) 12.5 isopropyl alcohol 5.0 acetic acid 0.7 ; perfume 0.08 water Balance `~
EX~MPLE 2 % by_weiqht hexylene glycol 10.0 5-chloro-2-(2,4-dichlorophenoxy)phenol 0.07 sodium 2-ethylhexyl sulfate (40%) 4.5 tetrasodium EDTA (36%) 18.75 isopropyl alcohol 5.0 , perfume 0.08 acetic acid 0.7 ;
water Balance ;.:
/O_by weiqht Carbowax 400 10.0 5-chloro-2-(2,4-dichlorophenoxy)phenol 0.07 sodium 2-ethylhexyl sulfate (40%) 4.5
. ~ :
~oqenes Enterbacter aeroqenes, pro-teus mirabitis, athlete's foot fungus (Trycophyton men-tagrophytes), Candida albicans, and black mold such as Aspergillus niqer and prevent the re-growth of such organisms for at least 28 days.
The following are represen-tative examples of the anti-microbial compositions of this invention.
. .
% by weiqht hexylene glycol 10.0 10- 5-chloro-2-(2,4-dichlorophenoxy)phenol 0.1 sodium 2-ethylhexyl sulfate (40% active) ~.5 lauryl alcohol ether sulfate (Na salt) (30% active) 0.33 -tetrasodium EDTA (36% active) 12.5 isopropyl alcohol 5.0 acetic acid 0.7 ; perfume 0.08 water Balance `~
EX~MPLE 2 % by_weiqht hexylene glycol 10.0 5-chloro-2-(2,4-dichlorophenoxy)phenol 0.07 sodium 2-ethylhexyl sulfate (40%) 4.5 tetrasodium EDTA (36%) 18.75 isopropyl alcohol 5.0 , perfume 0.08 acetic acid 0.7 ;
water Balance ;.:
/O_by weiqht Carbowax 400 10.0 5-chloro-2-(2,4-dichlorophenoxy)phenol 0.07 sodium 2-ethylhexyl sulfate (40%) 4.5
-3-... . . . . ......... . . . . .
- ~06~l6~S
' EXAMPLE 3 (cont'd) . % by_ wei~ .
tetrasodium EDTA ( 36%) 12 . 5 isopropyl alcohol 5,0 acetic acld 0.7 perfume 0.08 .
water Balance .~ .
% by weiqht ~.
hexylene glycol 15.0 ;
5-chloro-2-(2,4-dichlorophenoxy)phenol 0.07 disodium dodecyldiphenylether disulfonate (45% active) 4,0 tetrasodium EDTA ( 36%) 25.0 ;
isopropyl alcohol 5.0 acetic acid - 0, perfume o,o~ ~
water Balance t~ ,:
~ EXAMPLE 5 ~::. ;.-% by weiqht hexylene glycol 1 0 ;, ; 5-chloro-2-(2,4-dichlorophenoxy)phenol ~ 0 1 ` :
sodium 2-ethylhexyl sulfate (40%) -4.5 tetrasodium EDTA ( 36%) 12.5 ;' lauryl alcohol ether sulfate (Na salt) (30% active) 0-33 '~
isopropyl alcohol 5,0 acetic acid 0,35 ;:
perfume 0.08 `~
water (distilled) Balance ;
., _~ '": ' ~".. . "'''.' ' ;','''"" ;"''"""','',' '""' .: ''" '""''' '`
EXAMPLE 6 ~06~6 7S
: .. ..
% by weiqht hexylene glycol 1.0 5-chloro-2-(2,4-dichlorophenoxy)phenol0.1 `~
sodium 2-ethylhexyl sulfate (40%) 4.5 ~
trisodium NTA ~I20 12.0 ~ -lauryl alcohol ether sulfate (Na salt) (30% active) 0.33 isopropyl alcohol 5.0 perfume 0.08 '~
acetic acid Q.S.*to pH 10.3 water (distilled) Balance *Quantity sufficient EX~MPLE 7 % by weiqht `~;
5-chloro-2-(2,4-dichlorophenoxy)phenol0.07 ,-sodium 2-ethylhexyl sulfate (40%) 4.5 tetrasodium EDTA (36%) 25.0 ethoxylated lauryl alcohol 0.33 ;~ 20 isopropyl alcohol 5.0 acetic acid Q.S. to pH 10.3 .- ~, . .
perfume 0.08 water (distilled) BaLance -~
The compositions described in the above examples, were tested by standard procedures in order to determine their efficacy in killing various germs and fungi following the procedure des-cribed in the Official Methods for Analysis of_the AOAC, 11th Edi-tion, 1970, Chapter 4, paragraph 4.033 - 4.035, "Spray Disinfect-ant Test". Also, the Environmental Pro-tection Agency's "Hard Sur-face Mildew Fungistatic Test Method" (Revised 12-1-70) was used `
to test the effectiveness of the compositions against Asperqillus niqer. The following results were obtained.
~.~. ' ' ' :
~ - . . -. . . .
6~l67S
TEST RESULTS
Orqanism Ex. 1 Ex. 2 Ex. 3 Ex. 4 `~
Staphylococcus a. (30C) - - - 0/0 ;~
(60C) 0/0 0/0 0/0 Salmonella e. (30C) 0/0 0/0 0/0 0/0 Trichophyton m. (30C) 0/0 0/0 6/13 ..
Pseudomonas a. (30C) 0/0 0/0 0/0 , Asper~illus n. (4 weeks) 0 0 0 -TEST RESULTS
----orqanism Ex. 5 Exr 6 Ex. 7 Salmonella c. (30C) 0/0 0/0 0/0 -Staphylococcus a. (30C) 0/0 0/0 0/0 The first figure in the test results indicates the num-ber of culture tubes found with live growing organisms in the ini- ;
tial test, while the seeond figure indicates the number of live eultures found in the seeondary, or sub-eulture testsr -Various ehanges and modifieations of the invention ean be made, and, to the extent that sueh variations ineorporates the spirit of this invention, they are intended to be ineluded within `~
the seope of the appended claimsr -, : .
,,;' :
'~,,::,' , ,". . ' ..
: . :.
',~,: ~' ' ~', ,~', ' i :"' ~''' ~' :" "
-6- ! ;~
j ;'-
- ~06~l6~S
' EXAMPLE 3 (cont'd) . % by_ wei~ .
tetrasodium EDTA ( 36%) 12 . 5 isopropyl alcohol 5,0 acetic acld 0.7 perfume 0.08 .
water Balance .~ .
% by weiqht ~.
hexylene glycol 15.0 ;
5-chloro-2-(2,4-dichlorophenoxy)phenol 0.07 disodium dodecyldiphenylether disulfonate (45% active) 4,0 tetrasodium EDTA ( 36%) 25.0 ;
isopropyl alcohol 5.0 acetic acid - 0, perfume o,o~ ~
water Balance t~ ,:
~ EXAMPLE 5 ~::. ;.-% by weiqht hexylene glycol 1 0 ;, ; 5-chloro-2-(2,4-dichlorophenoxy)phenol ~ 0 1 ` :
sodium 2-ethylhexyl sulfate (40%) -4.5 tetrasodium EDTA ( 36%) 12.5 ;' lauryl alcohol ether sulfate (Na salt) (30% active) 0-33 '~
isopropyl alcohol 5,0 acetic acid 0,35 ;:
perfume 0.08 `~
water (distilled) Balance ;
., _~ '": ' ~".. . "'''.' ' ;','''"" ;"''"""','',' '""' .: ''" '""''' '`
EXAMPLE 6 ~06~6 7S
: .. ..
% by weiqht hexylene glycol 1.0 5-chloro-2-(2,4-dichlorophenoxy)phenol0.1 `~
sodium 2-ethylhexyl sulfate (40%) 4.5 ~
trisodium NTA ~I20 12.0 ~ -lauryl alcohol ether sulfate (Na salt) (30% active) 0.33 isopropyl alcohol 5.0 perfume 0.08 '~
acetic acid Q.S.*to pH 10.3 water (distilled) Balance *Quantity sufficient EX~MPLE 7 % by weiqht `~;
5-chloro-2-(2,4-dichlorophenoxy)phenol0.07 ,-sodium 2-ethylhexyl sulfate (40%) 4.5 tetrasodium EDTA (36%) 25.0 ethoxylated lauryl alcohol 0.33 ;~ 20 isopropyl alcohol 5.0 acetic acid Q.S. to pH 10.3 .- ~, . .
perfume 0.08 water (distilled) BaLance -~
The compositions described in the above examples, were tested by standard procedures in order to determine their efficacy in killing various germs and fungi following the procedure des-cribed in the Official Methods for Analysis of_the AOAC, 11th Edi-tion, 1970, Chapter 4, paragraph 4.033 - 4.035, "Spray Disinfect-ant Test". Also, the Environmental Pro-tection Agency's "Hard Sur-face Mildew Fungistatic Test Method" (Revised 12-1-70) was used `
to test the effectiveness of the compositions against Asperqillus niqer. The following results were obtained.
~.~. ' ' ' :
~ - . . -. . . .
6~l67S
TEST RESULTS
Orqanism Ex. 1 Ex. 2 Ex. 3 Ex. 4 `~
Staphylococcus a. (30C) - - - 0/0 ;~
(60C) 0/0 0/0 0/0 Salmonella e. (30C) 0/0 0/0 0/0 0/0 Trichophyton m. (30C) 0/0 0/0 6/13 ..
Pseudomonas a. (30C) 0/0 0/0 0/0 , Asper~illus n. (4 weeks) 0 0 0 -TEST RESULTS
----orqanism Ex. 5 Exr 6 Ex. 7 Salmonella c. (30C) 0/0 0/0 0/0 -Staphylococcus a. (30C) 0/0 0/0 0/0 The first figure in the test results indicates the num-ber of culture tubes found with live growing organisms in the ini- ;
tial test, while the seeond figure indicates the number of live eultures found in the seeondary, or sub-eulture testsr -Various ehanges and modifieations of the invention ean be made, and, to the extent that sueh variations ineorporates the spirit of this invention, they are intended to be ineluded within `~
the seope of the appended claimsr -, : .
,,;' :
'~,,::,' , ,". . ' ..
: . :.
',~,: ~' ' ~', ,~', ' i :"' ~''' ~' :" "
-6- ! ;~
j ;'-
Claims (10)
1. An antimicrobial aqueous solution, comprising water and, by weight, about 0.05 to 0.5% of 5-chloro-2-(2,4-dichloro-phenoxy)phenol, about 3 to 15% tetrasodium ethylenediamine tetraacetate or trisodium nitrilotriacetate, about 0.5 to 4%
anionic surfactant and 0% to about 20% of water-miscible glycol solvent, wherein said anionic surfactant is selected from the group consisting of disodium dodecyldiphenylether disulfonate and sodium 2-ethylhexyl sulfate.
anionic surfactant and 0% to about 20% of water-miscible glycol solvent, wherein said anionic surfactant is selected from the group consisting of disodium dodecyldiphenylether disulfonate and sodium 2-ethylhexyl sulfate.
2. A solution in accordance with claim 1, containing up to 20% by weight of said water-miscible glycol solvent, said solvent being selected from the group consisting of hexylene glycol and polyethylene glycols having a molecular weight of up to about 600.
3. A solution in accordance with claim 1, in which about 5% of lower alkanol is included.
4. A solution in accordance with claim 1, in which about 1 to 12% I by weight, hexylene glycol is included as said glycol solvent.
5. A solution in accordance with claim 1, containing up to 20% by weight of hexylene glycol as said water-miscible glycol solvent.
6. A solution in accordance with claim 1, 2 or 4, in which said anionic surfactant is sodium 2-ethylhexyl sulfate.
7. An aqueous solution in accordance with claim 1 or 3, containing up to 20% by weight, of a polyethylene glycol having an average molecular weight of about 400 as said water-miscible glycol solvent.
8. An aqueous solution in accordance with claim 1, comprising, by weight, about 0.06 to 0.2% of said 5-chloro-2-(2,4-dichlorophenoxy) phenol, about 5 to 10% of said tetra-sodium ethylenediamine tetraacetate, about 1 to 2% of said anionic surfactant; about 7 to 15% of said water-miscible glycol solvent and about 5% of isopropyl alcohol.
9. An aqueous solution in accordance with claim 8, in which said anionic surfactant is sodium 2-ethylhexyl sulfate and said water-miscible glycol solvent is hexylene glycol.
10. An aqueous solution in accordance with claim 8 or 9, including acetic acid in an amount sufficient to provide a pH of about 10.3.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US64870276A | 1976-01-13 | 1976-01-13 | |
US74552076A | 1976-11-26 | 1976-11-26 |
Publications (1)
Publication Number | Publication Date |
---|---|
CA1061675A true CA1061675A (en) | 1979-09-04 |
Family
ID=27095450
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA267,952A Expired CA1061675A (en) | 1976-01-13 | 1976-12-15 | Antimicrobial cleaning compositions |
Country Status (10)
Country | Link |
---|---|
AU (1) | AU507081B2 (en) |
CA (1) | CA1061675A (en) |
DE (1) | DE2659780A1 (en) |
DK (1) | DK152378C (en) |
ES (1) | ES454948A1 (en) |
FR (1) | FR2338052A1 (en) |
GB (1) | GB1511991A (en) |
IT (1) | IT1076206B (en) |
NL (1) | NL7700247A (en) |
SE (1) | SE425976B (en) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4124520A (en) * | 1977-06-20 | 1978-11-07 | United States Borax & Chemical Corp. | Anti-microbial bathroom cleaning compositions containing o-benzyl-4-chlorophenol |
GB2126894B (en) * | 1982-09-17 | 1986-09-03 | Auchincloss Thomas R | Disinfectant composition |
GB9709065D0 (en) * | 1997-05-02 | 1997-06-25 | Unilever Plc | Improvements relating to hard surface cleaning |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3506720A (en) * | 1963-02-22 | 1970-04-14 | Geigy Chem Corp | Halogenated hydroxy-diphenyl ethers |
GB1067539A (en) * | 1965-03-31 | 1967-05-03 | Unilever Ltd | Antimicrobial composition |
US3472900A (en) * | 1966-07-18 | 1969-10-14 | Baird Chem Ind | Preparation of trialkylamines |
US3629477A (en) * | 1966-08-08 | 1971-12-21 | Geigy Chem Corp | Halogenated diphenyether-containing compositions and control of pests therewith |
DE1767683A1 (en) * | 1968-06-04 | 1971-09-30 | Henkel & Cie Gmbh | Detergents, washing auxiliaries and cleaning agents containing antimicrobial agents |
NL7018669A (en) * | 1969-12-23 | 1971-06-25 | ||
DE2015188A1 (en) * | 1970-03-28 | 1971-10-21 | ||
BE768041R (en) * | 1971-06-03 | 1971-12-03 | Ciba Geigy Ag | COMPOSITION TO FIGHT THE |
GB1420946A (en) * | 1972-10-13 | 1976-01-14 | Beecham Group Ltd | Anti-bacterial compositions |
US3897357A (en) * | 1972-12-06 | 1975-07-29 | American Home Prod | Bacteriostatic toilet bowl cleaner compositions |
-
1976
- 1976-12-15 CA CA267,952A patent/CA1061675A/en not_active Expired
- 1976-12-31 DE DE19762659780 patent/DE2659780A1/en active Granted
-
1977
- 1977-01-04 DK DK1977A patent/DK152378C/en active
- 1977-01-05 SE SE7700108A patent/SE425976B/en not_active IP Right Cessation
- 1977-01-05 GB GB15877A patent/GB1511991A/en not_active Expired
- 1977-01-11 ES ES454948A patent/ES454948A1/en not_active Expired
- 1977-01-12 NL NL7700247A patent/NL7700247A/en not_active Application Discontinuation
- 1977-01-12 IT IT1922277A patent/IT1076206B/en active
- 1977-01-12 FR FR7700715A patent/FR2338052A1/en active Granted
- 1977-02-03 AU AU21932/77A patent/AU507081B2/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
SE7700108L (en) | 1977-07-14 |
NL7700247A (en) | 1977-07-15 |
FR2338052B1 (en) | 1980-11-28 |
DK1977A (en) | 1977-07-14 |
AU2193277A (en) | 1978-08-10 |
SE425976B (en) | 1982-11-29 |
DK152378C (en) | 1988-07-25 |
FR2338052A1 (en) | 1977-08-12 |
DK152378B (en) | 1988-02-22 |
DE2659780C2 (en) | 1987-04-23 |
DE2659780A1 (en) | 1977-07-14 |
ES454948A1 (en) | 1979-07-16 |
AU507081B2 (en) | 1980-01-31 |
IT1076206B (en) | 1985-04-27 |
GB1511991A (en) | 1978-05-24 |
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