WO1996038043B1 - Potentiation of biocide activity using an n-alkyl heterocyclic compound - Google Patents
Potentiation of biocide activity using an n-alkyl heterocyclic compoundInfo
- Publication number
- WO1996038043B1 WO1996038043B1 PCT/US1996/007677 US9607677W WO9638043B1 WO 1996038043 B1 WO1996038043 B1 WO 1996038043B1 US 9607677 W US9607677 W US 9607677W WO 9638043 B1 WO9638043 B1 WO 9638043B1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- dodecyl
- heterocyclic compound
- alkyl heterocyclic
- methyl
- microbicide
- Prior art date
Links
- 230000003115 biocidal Effects 0.000 title 1
- 239000003139 biocide Substances 0.000 title 1
- 230000000694 effects Effects 0.000 title 1
- 230000003641 microbiacidal Effects 0.000 claims abstract 35
- 239000002855 microbicide agent Substances 0.000 claims abstract 22
- 244000005700 microbiome Species 0.000 claims abstract 21
- 239000000203 mixture Substances 0.000 claims abstract 16
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 8
- 239000000758 substrate Substances 0.000 claims abstract 8
- 239000004753 textile Substances 0.000 claims abstract 2
- JMTFLSQHQSFNTE-UHFFFAOYSA-N 1-dodecylimidazole Chemical compound CCCCCCCCCCCCN1C=CN=C1 JMTFLSQHQSFNTE-UHFFFAOYSA-N 0.000 claims 10
- 241000894006 Bacteria Species 0.000 claims 8
- 241000195493 Cryptophyta Species 0.000 claims 8
- 241000233866 Fungi Species 0.000 claims 8
- ZRIILUSQBDFVNY-UHFFFAOYSA-N 4-dodecylmorpholine Chemical compound CCCCCCCCCCCCN1CCOCC1 ZRIILUSQBDFVNY-UHFFFAOYSA-N 0.000 claims 7
- -1 2-pyrrolidinonyl Chemical group 0.000 claims 6
- SSYUVFKVRKTANJ-UHFFFAOYSA-N 1-dodecyl-2-methylpiperidine Chemical compound CCCCCCCCCCCCN1CCCCC1C SSYUVFKVRKTANJ-UHFFFAOYSA-N 0.000 claims 5
- GUSTUIJJPMXTTI-UHFFFAOYSA-N 1-dodecylazepane Chemical compound CCCCCCCCCCCCN1CCCCCC1 GUSTUIJJPMXTTI-UHFFFAOYSA-N 0.000 claims 5
- BHDDSIBLLZQKRF-UHFFFAOYSA-N 1-dodecylpiperidine Chemical compound CCCCCCCCCCCCN1CCCCC1 BHDDSIBLLZQKRF-UHFFFAOYSA-N 0.000 claims 5
- UUIVKBHZENILKB-UHFFFAOYSA-N 2,2-Dibromo-2-cyanoacetamide Chemical compound NC(=O)C(Br)(Br)C#N UUIVKBHZENILKB-UHFFFAOYSA-N 0.000 claims 5
- 229940100484 5-chloro-2-methyl-4-isothiazolin-3-one Drugs 0.000 claims 5
- LVDKZNITIUWNER-UHFFFAOYSA-N Bronopol Chemical compound OCC(Br)(CO)[N+]([O-])=O LVDKZNITIUWNER-UHFFFAOYSA-N 0.000 claims 5
- DHNRXBZYEKSXIM-UHFFFAOYSA-N Methylchloroisothiazolinone Chemical group CN1SC(Cl)=CC1=O DHNRXBZYEKSXIM-UHFFFAOYSA-N 0.000 claims 5
- 230000003389 potentiating Effects 0.000 claims 5
- SBUKOHLFHYSZNG-UHFFFAOYSA-N (2S,6S)-4-dodecyl-2,6-dimethylmorpholine Chemical compound CCCCCCCCCCCCN1CC(C)OC(C)C1 SBUKOHLFHYSZNG-UHFFFAOYSA-N 0.000 claims 4
- 229940116368 1,2-benzisothiazoline-3-one Drugs 0.000 claims 4
- UZWJYXOTRCVFQE-UHFFFAOYSA-N 1-dodecyl-3-methylpiperidine Chemical compound CCCCCCCCCCCCN1CCCC(C)C1 UZWJYXOTRCVFQE-UHFFFAOYSA-N 0.000 claims 4
- DITCUBDNORXKGS-UHFFFAOYSA-N 1-dodecyl-4-methylpiperidine Chemical compound CCCCCCCCCCCCN1CCC(C)CC1 DITCUBDNORXKGS-UHFFFAOYSA-N 0.000 claims 4
- NJPQAIBZIHNJDO-UHFFFAOYSA-N 1-dodecylpyrrolidin-2-one Chemical compound CCCCCCCCCCCCN1CCCC1=O NJPQAIBZIHNJDO-UHFFFAOYSA-N 0.000 claims 4
- JVCRHTKQAPRUKG-UHFFFAOYSA-N 1-dodecylpyrrolidine Chemical compound CCCCCCCCCCCCN1CCCC1 JVCRHTKQAPRUKG-UHFFFAOYSA-N 0.000 claims 4
- YFLDZPUXCOSOGU-UHFFFAOYSA-N 1-iodoprop-2-ynyl N-butylcarbamate Chemical compound CCCCNC(=O)OC(I)C#C YFLDZPUXCOSOGU-UHFFFAOYSA-N 0.000 claims 4
- RCVKZMQGFZRHKO-UHFFFAOYSA-N 1-iodoprop-2-ynyl carbamate Chemical compound NC(=O)OC(I)C#C RCVKZMQGFZRHKO-UHFFFAOYSA-N 0.000 claims 4
- BSWWXRFVMJHFBN-UHFFFAOYSA-N 2,4,6-Tribromophenol Chemical compound OC1=C(Br)C=C(Br)C=C1Br BSWWXRFVMJHFBN-UHFFFAOYSA-N 0.000 claims 4
- SOAKROFTPUDVLZ-UHFFFAOYSA-N 5-(chloromethyl)-3-dodecyl-1,3-oxazolidin-2-one Chemical compound CCCCCCCCCCCCN1CC(CCl)OC1=O SOAKROFTPUDVLZ-UHFFFAOYSA-N 0.000 claims 4
- DMSMPAJRVJJAGA-UHFFFAOYSA-N Benzisothiazolinone Chemical compound C1=CC=C2C(=O)NSC2=C1 DMSMPAJRVJJAGA-UHFFFAOYSA-N 0.000 claims 4
- 229940100555 2-methyl-4-isothiazolin-3-one Drugs 0.000 claims 3
- BEGLCMHJXHIJLR-UHFFFAOYSA-N Methylisothiazolinone Chemical compound CN1SC=CC1=O BEGLCMHJXHIJLR-UHFFFAOYSA-N 0.000 claims 3
- KXDHJXZQYSOELW-UHFFFAOYSA-M carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 2
- 238000009472 formulation Methods 0.000 claims 2
- 125000002632 imidazolidinyl group Chemical group 0.000 claims 2
- 125000002636 imidazolinyl group Chemical group 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 125000002757 morpholinyl group Chemical group 0.000 claims 2
- 125000004193 piperazinyl group Chemical group 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- 125000003072 pyrazolidinyl group Chemical group 0.000 claims 2
- 125000002755 pyrazolinyl group Chemical group 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
- 125000001422 pyrrolinyl group Chemical group 0.000 claims 2
- 229920000126 Latex Polymers 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 239000000498 cooling water Substances 0.000 claims 1
- 239000003599 detergent Substances 0.000 claims 1
- 239000000839 emulsion Substances 0.000 claims 1
- 239000012530 fluid Substances 0.000 claims 1
- 238000005755 formation reaction Methods 0.000 claims 1
- 150000002391 heterocyclic compounds Chemical class 0.000 claims 1
- 239000004816 latex Substances 0.000 claims 1
- 238000005555 metalworking Methods 0.000 claims 1
- 239000011347 resin Substances 0.000 claims 1
- 229920005989 resin Polymers 0.000 claims 1
- 239000002002 slurry Substances 0.000 claims 1
- 239000011248 coating agent Substances 0.000 abstract 1
- 238000000576 coating method Methods 0.000 abstract 1
- 239000010985 leather Substances 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 239000003643 water by type Substances 0.000 abstract 1
Abstract
A method for increasing the effectiveness of a microbicide is described. In the method, a microbicide and an N-alkyl heterocyclic compound are applied to a substrate or aqueous system subject to the growth of microorganisms. The N-alkyl heterocyclic compound is applied in an amount effective to increase the microbicidal activity of the microbicide. The N-alkyl heterocyclic compound has formula (I). The variable 'n' ranges from 5 to 17, and the heterocyclic ring defined by (a) is a substituted or unsubstituted ring having four to eight members. Microbicidal compositions are described where the microbicide and the N-alkyl heterocyclic compound are present in a combined amount effective to control the growth of at least one microorganism. Methods for controlling the growth of microorganisms on various substrates and in various aqueous systems are also described. The combination of the microbicide and the N-alkyl heterocyclic compound is particularly useful as a microbicide in the leather industry, the lumber industry, the papermaking industry, the textile industry, the agricultural industry, and the coating industry, as well as in industrial process waters.
Claims
AMENDED CLAIMS
[received by the International Bureau on 17 December 1996 (17.12.96); original claims 1, 5, 11, 17 and 22 amended; remaining claims unchanged (6 pages)]
1. A method to increase the effectiveness of a microbicide comprising the step of applying at least one microbicide and an N-alkyl heterocyclic compound to a substrate or aqueous system subject to the growth of microorganisms, wherein the N-alkyl heterocyclic compound has the formula:
in which n varies from 5 to 17 and the heterocyclic ring defined by is a substituted or
unsubstituted ring having four to eight members and the N-alkyl heterocyclic compound is applied in an amount effective to potentiate the microbicidal activity of the microbicide.
2. A method according to claim 1, wherein the microbicide is selected from 5-chloro-2-methyl-4-isothiazolin-3-one, 2-methyl-4-isothiazolin-3-one, 2-bromo-2-nitropropane-1 ,3-diol, iodopropargyl butyl carbamate, iodopropargyl carbamate, 2,2-dibromo-3- nitrilopropionamide, tribromophenol, and 1,2-benzisothiazoline-3-one, and mixtures thereof, and the N-alkyl heterocyclic compound is selected from N-dodecyl morpnoline, N-dodecyl imidazole, N-dodecyl-2.6-dimethyl-morpholine, N-dodecyl- 5-chloromethyl-2-oxazolidinone, N-dodecyl-2-pyrrolidinone, N-dodecyl hexamethyleneimine, N-dodecyl pyrrolidine, N-dodecyl-3-methyl-piperidine, N-dodecyl piperidine, N-dodecyl-4-methyl-piperidine and N-dodecyl-2-methyl-piperidine.
3. A method according to claim 2, wherein the N-alkyl heterocyclic compound is N-dodecyl morpnoline.
4. A method according to claim 2, wherein the N-alkyl heterocyclic compound is N-dodecyl imidazole.
5. A microbicidal composition comprising:
(a) at least one microbicide and
(b) an N-alkyl heterocyclic compound of the formula:
herein n varies from 5 to 17, the heterocyclic ring defined by is a substituted or
unsubstituted ring having four to eight members, and wherein (a) and (b) are present in a combined amount effective to control the growth, of at least one microorganism and the N-alkyl heterocyclic compound (b) is present in an amount effective to potentiate the microbicidal activity of the microbicide (a).
6. A microbicidal composition according to claim 5, wherein n varies from 9 to 15, and die heterocyclic ring is selected from the group consisting of pyrrolidinyl, 2-pyrrolidinonyl, pyrrolinyl, pyrazolidinyl, pyrazolinyl, pyrazolyl, imidazolidinyl, imidazolinyl, imidazolyl, oxazolidinonyl, piperidinyl, piperazinyl, morpholinyl, hexamethyleneiminyl, and
heptamethyleneiminyl.
7. A microbicidal composition according to claim 5, wherein microbicide selected from 5-chloro-2-methyl-4-isothiazolin-3-one, 2-methyl-4-isothiazolin-3-one, 2-bromo-2-nitropropane-1 ,3-diol iodopropargyl butyl carbamate, iodopropargyl carbamate, 2,2-dibromo-3-nitrilopropionamide, tribromophenol, 1,2-benzisothiazoline-3-one, and mixtures thereof, and the N-alkyl heterocyclic compound is selected from the group consisting of N-dodecyl morpholine, N-dodecyl imidazole, N-dodecyl-2,6-dimethyl-morpholine, N-dodecyl-5-chloromethyl-2-oxazolidinone, N-dodecyl-2-pyrrolidinone, N-dodecyl hexamethyleneimine, N-dodecyl pyrrolidine, N-dodecyl-3-methyl-piperigine, N-dodecyl piperidine, N-dodecyl-4-methylpiperidine and N-dodecyl-2-methyl-piperidine.
8. A microbicidal composition according to claim 5, wherein the N-alkyl heterocyclic compound is N-dodecyl morphoiine and the microorganism is selected from algae, fungi, and bacteria.
9. A microbicidal composition, according to claim 5, wherein the N-alkyl heterocyclic compound is N-dodecyl imidazole and the microorganism is selected from algae, fungi, and bacteria. 10. A microbicidal composition according to claim 5, wherein the composition is an aqueous formulation.
11. A method for controiling the growth of microorganisms on a substrate comprising the step of contacting a substrate susceptible to the growth of microorganisms with
(a) at least one microbicide, and
(b) an N-alkyl heterocyclic compound of the formula:
wherein n may be from 5 to 17, the heterocyclic ring defined by
is a substituted or unsubstituted ring having four to eight members, and wherein (a) and (b) are present in a combined amount effective to control the growth of at least one microorganism on the substrate and the N-alkyl heterocyclic compound (b) is present in sn amount effective to potentiate the microbicidal activity of the microbicide (a).
12. A method according to claim 11, wherein n varies from 9 to 15, and the heterocyclic ring is selected from the group consisting of pyrrolidinyl, 2-pyrrolidinonyl, pyrrolinyl, pyrazolidinyl, pyrazolinyl, pyrazolyl, imidazolidinyl, imidazolinyl, imidazolyl, oxazolidinonyl, piperidinyl, piperazinyl, morpholinyl, hexamethyleneiminyl, and
heptamethyleneiminyl.
13. A method according to claim 11. wherein the microbicide is selected from 5-chloro-2-methyl-4-isothiazolin-3-one, 2-metbyl-4-isothiazolin-3-one, 2-bromo-2-nitropropane-1,3-diol, iodopropargyl butyl carbamate, lodopropargyl carbamate, 2,2-dibromo-3-nitrilopropionamide, tribromophenol, and 1 ,2-benzisothiazoline-3-one, and mixtures thereof, and
the N-alkyl heterocyclic compound is selected from N-dodecyl morpholine, N-dodecyl imidazole, N-dodecyl-2,6-dimethyl-morpholine- N-dodecyl-5-chlororaethyl-2-oxazolidinone, N-dodecyl-2-pyrrolidinone, N-dodecyl hexamethyleneimine, N-dodecyl pyrrolichne, N-dodecyl-3-methyl-piperidine, N-dodecyl piperidine. N-dodecyl-4-methyl-piperidine and N-dodecyl-2-methyl-piperidine.
14. A method according to claim 11. wherein the N-alkyl heterocyclic compound 35 N-dodecyl morpholine and the microorganism is selected from algae, fungi, and bacteria. 15. A method according to claim 11 , wherein the N-alkyl heterocyclic compound is
N-dodecyl imidazole. and the microorganism is selected from algae. fungi, and bacteria.
16. A method of claim 11 wherein the substrate is a hide, a textile substrate, lumber, a seed, or a plant.
17. A method for controlling the growth of microorganisms in an aqueous system capable of supporting growth of a microorganism comprising the step of treating the aqueous system with
(a) at least one microbicide, and
(b) an N-alkyl heterocyclic compound of the formula;
wherein n varies from 5 to 17, the heterocyclic ring defined by is a substituted or
unsubstituted ring having four to eight m embers, and wherein (a) and (b) are present in a combined amount effective to control the growth of at least one microorganism and the N-alkyl heterocyclic compound (b) is present in an amount effective to potentiate the microbicidal activity of the microbicide (a).
18. A method according to claim 17, wherein the microbicide is selected from 5-chloro-2-methyl-4-isothiazolin-3-one, 2-methyl-4-isotbiazolin-3-one, 2-bromo-2-nitropropane-1,3-diol, iodopropargyl butyl carbamate, iodopropargyl carbamate, 2,2-dibromo-3-nitrilopropionamide, tribromophenol, and 1,2-benzisothiazoIine-3-one, and mixtures thereof, and the N-alkyl heterocyclic compound is selected from N-dodecyl morpholine, N-dodecyl imidazole, N-dodecyl-2,6-dimethyl-morpholine, N-dodecyl-5-chloromethyl-2-oxazolidinone, N-dodecyI-2-pyrrolidinone, N-dodecyl hexamethyleneimine, N-dodecyl pyrrolidine, N-dodecyl-3-methyl-piperidine, N-dodecyl piperidine, N-dodecyl-4-methyl-piperidine and N-dodecyl-2-methyl-piperidine. 19. A method according to claim 17, wherein the N-alkyl heterocyclic compound is N-dodecyl morpholine and the microorganism is selected from algae, fungi, and bacteria.
28. A method according to claim 17, wherein the N-alkyl heterocyclic compound is N-dodecyl imidazole, and. the microorganism is selected from algae, fungi, and bacteria.
21. A method according to claim 17, wherein said aqueous system is selected from the group consisting of a latex, a metal working fluid, an aqueous emulsion, an aqueous detergent, cooling water, and an aqueous resin formulation.
22. A method for controlling the growth of microorganisms on pulp or paper in a papermaking process, comprising the step of contacting the pulp or paper with
(a) at least one tnicrobicide, and
(b) an N-alkyl heterocyclic compound of the formula:
wherein n varies from 5 to 17, the heterocyclic ring defined by is a substituted or
unsubstituted ring having four to eight members, and (a) and (b) are present in a combined amount effective to control the growth of at least one microorganism and the N-alkyl
heterocyclic compound (b) is present in an amount effective to potentiate the microbicidal activity of the microbicide (a).
23. A method according to claim 22, wherein the pulp is contacted by mixing the microbicide and an N-alkyl heterocyclic compound into a pulp slurry prior to reaching a formation wire in a papermaking process.
24. A method according to claim 22. wherein the microbicide is selected from 5-chloro-2-methyl-4-isothiazolin-3-one, 2-methyl-4-isothiazolin- 3-one, 2-bromo-2-nitropropane-1,3-diol, iodopropargyl buryl carbamate, iodopropargyl carbamate, 2,2-dibromo-3-nitrilopropionamide, tribaromophenol, and 1,2-benzisothiazoline-3-one, and mixtures thereof, and the N-alkyl heterocyclic compound is selected from N-dodecyl morpholine, N-dodecyl imidazole, N-dodecyl-2,6-dimethyl-morpholine, N-dodecyl-5-chloromethyl-2-oxazolidinone, N-dodecyl-2-pyrrolidinone. N-dodecyl hexamethyleneimine, N-dodecyl pyrrolidine, N-dodecyl-3-methyl-piperidine, N-dodecyl piperidine, N-dodecyI-4-methyl-pipendine and N-dodecyl-2-methyl-piperidine.
25 A method according to claim 22, wherein the N-alkyl heterocyclic compound is N-dodecyl morpholine and the microorganism is selected from algae, fungi, and bacteria.
26. A method according to claim 22, wherein the N-alkyl heterocyclic compound is N-dodecyl imidazole, and the microorganism is selected from algae, fungi, and bacteria.
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NZ309305A NZ309305A (en) | 1995-05-30 | 1996-05-28 | Potentiation of biocide activity using an n-alkyl heterocyclic compound |
| DE69629713T DE69629713T2 (en) | 1995-05-30 | 1996-05-28 | BIOCIDAL ENHANCEMENT OF EFFECT THROUGH N-ALKYL-HETEROCYCLIC COMPOUND |
| BR9608368A BR9608368A (en) | 1995-05-30 | 1996-05-28 | Method to increase the effectiveness of a microbicidal agent microbicidal composition and method to control the growth of microorganisms |
| CA002222864A CA2222864C (en) | 1995-05-30 | 1996-05-28 | Potentiation of biocide activity using an n-alkyl heterocyclic compound |
| AT96916627T ATE247902T1 (en) | 1995-05-30 | 1996-05-28 | BIOCIDAL EFFECT INCREASED THROUGH N-ALKYL HETEROCYCLIC COMPOUND |
| MX9709354A MX9709354A (en) | 1995-05-30 | 1996-05-28 | Potentiation of biocide activity using an n-alkyl heterocyclic compound. |
| JP8536575A JPH11506103A (en) | 1995-05-30 | 1996-05-28 | Activation of bactericidal effect using N-alkylheterocyclic compound |
| AU59315/96A AU5931596A (en) | 1995-05-30 | 1996-05-28 | Potentiation of biocide activity using an n-alkyl heterocycl ic compound |
| EP96916627A EP0857021B1 (en) | 1995-05-30 | 1996-05-28 | Potentiation of biocide activity using an n-alkyl heterocyclic compound |
| SK1608-97A SK160897A3 (en) | 1995-05-30 | 1996-05-28 | Potentiation of biocide activity using an n-alkyl heterocyclic compound |
| NO975501A NO975501L (en) | 1995-05-30 | 1997-11-28 | Potentiation of biocidal activity using an N-alkyl heterocyclic compound |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/453,001 | 1995-05-30 | ||
| US08/453,001 US6034081A (en) | 1995-05-30 | 1995-05-30 | Potentiation of biocide activity using an N-alkyl heterocyclic compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO1996038043A1 WO1996038043A1 (en) | 1996-12-05 |
| WO1996038043B1 true WO1996038043B1 (en) | 1997-01-30 |
Family
ID=23798832
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US1996/007677 WO1996038043A1 (en) | 1995-05-30 | 1996-05-28 | Potentiation of biocide activity using an n-alkyl heterocyclic compound |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US6034081A (en) |
| EP (1) | EP0857021B1 (en) |
| JP (1) | JPH11506103A (en) |
| CN (1) | CN1190869A (en) |
| AR (1) | AR002134A1 (en) |
| AT (1) | ATE247902T1 (en) |
| AU (1) | AU5931596A (en) |
| BR (1) | BR9608368A (en) |
| CA (1) | CA2222864C (en) |
| CZ (1) | CZ378097A3 (en) |
| DE (1) | DE69629713T2 (en) |
| ES (1) | ES2205033T3 (en) |
| MX (1) | MX9709354A (en) |
| NO (1) | NO975501L (en) |
| NZ (1) | NZ309305A (en) |
| PT (1) | PT857021E (en) |
| SK (1) | SK160897A3 (en) |
| WO (1) | WO1996038043A1 (en) |
| ZA (1) | ZA964131B (en) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19722858B4 (en) | 1997-05-23 | 2004-01-29 | Schülke & Mayr GmbH | Compositions based on iodopropynyl and formaldehyde depot compounds and their use as preservatives |
| DE19737315C2 (en) * | 1997-08-27 | 2001-05-10 | Herbert Widulle | Use of mixtures of substances to kill mycobacteria |
| US5929073A (en) * | 1997-09-16 | 1999-07-27 | Buckman Laboratories International, Inc. | Synergistic antimicrobial compositions containing dodecylmorpholine a salt thereof and dodecylamine or a salt thereof |
| US6866906B2 (en) * | 2000-01-26 | 2005-03-15 | International Paper Company | Cut resistant paper and paper articles and method for making same |
| US20030166483A1 (en) * | 2000-04-04 | 2003-09-04 | Michael Heinzel | Use of 3-iodine-2-propinyl-carbamates as antimicrobial active agent |
| IL138771A0 (en) * | 2000-09-28 | 2001-10-31 | Bromine Compounds Ltd | A compacted 2,2-dibromo-3-nitrilopropionamide |
| MXPA03009304A (en) * | 2001-04-11 | 2004-11-12 | Int Paper Co | Paper articles exhibiting long term storageability. |
| US7279071B2 (en) * | 2001-04-11 | 2007-10-09 | International Paper Company | Paper articles exhibiting water resistance and method for making same |
| US20060254736A1 (en) * | 2001-04-11 | 2006-11-16 | Jackson John F | Paper articles exhibiting water resistance and method for making same |
| RU2330911C2 (en) | 2002-09-13 | 2008-08-10 | Интернэшнл Пейпер Компани | Paper of improved rigidity and bulk and method to produce thereof |
| JP4546132B2 (en) * | 2004-04-13 | 2010-09-15 | 日本エンバイロケミカルズ株式会社 | Industrial sterilization composition and method for preparing the same |
| MX2007000099A (en) * | 2004-07-06 | 2007-04-10 | Int Paper Co | Paper substrates containing an antimicrobial compound as well as methods of making and using the same. |
| CA2750039A1 (en) | 2005-03-11 | 2006-09-21 | International Paper Company | Substrate comprising expandable microspheres |
| JP5291292B2 (en) * | 2007-02-01 | 2013-09-18 | 協同油脂株式会社 | Metal working fluid and metal working method |
| WO2010019718A2 (en) | 2008-08-13 | 2010-02-18 | California Institute Of Technology | Carrier nanoparticles and related compositions, methods and systems |
| WO2010025383A1 (en) | 2008-08-28 | 2010-03-04 | International Paper Company | Expandable microspheres and methods of making and using the same |
| WO2010148156A1 (en) | 2009-06-16 | 2010-12-23 | International Paper Company | Anti-microbial paper substrates useful in wallboard tape applications |
| GB201010374D0 (en) * | 2010-06-21 | 2010-08-04 | Mtp Innovations Ltd | Disinfectant composition |
| EP2594133B1 (en) * | 2011-11-16 | 2014-03-19 | Rohm and Haas Company | Hindered primary chlorinated amine in a latex formulation |
| EP3513812B1 (en) | 2013-03-01 | 2020-07-15 | California Institute of Technology | Nanoparticles stabilized with nitrophenylboronic acid compositions |
| US9132097B2 (en) | 2013-03-01 | 2015-09-15 | California Institute Of Technology | Nanoparticles stabilized with nitrophenylboronic acid compositions |
| US9468681B2 (en) | 2013-03-01 | 2016-10-18 | California Institute Of Technology | Targeted nanoparticles |
| WO2015077209A1 (en) * | 2013-11-19 | 2015-05-28 | Arch Chemicals, Inc. | Enhanced preservative |
| EP3317323B1 (en) | 2015-07-01 | 2021-05-26 | California Institute of Technology | Cationic mucic acid polymer-based delivery systems |
| JP6352507B1 (en) * | 2017-07-27 | 2018-07-04 | 第一工業製薬株式会社 | Hydrogen gas barrier film composition and hydrogen gas barrier film using the same |
| US20190249360A1 (en) | 2018-02-15 | 2019-08-15 | Buckman Laboratories International, Inc. | Method And System For Tagging Leather Or Hides Treated With Biocide And Identifying Same |
| WO2023111296A1 (en) | 2021-12-17 | 2023-06-22 | Basf Se | Composition comprising an antimicrobial agent and a carboxamide |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3923870A (en) * | 1973-07-11 | 1975-12-02 | Troy Chemical Corp | Urethanes of 1-halogen substituted alkynes |
| US4173643A (en) * | 1973-12-20 | 1979-11-06 | Rohm And Haas Company | Synergistic microbiocidal compositions |
| US5182277A (en) * | 1985-03-04 | 1993-01-26 | Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara R.T. | Fungicides and plant-growth controlling agents |
| DD243632B1 (en) * | 1985-12-02 | 1990-09-05 | Fahlberg List Veb | AGENTS FOR THE CONTROL OF PHYTOPATHOGENIC BACTERIA AND MUSHROOMS |
| US4661503A (en) * | 1986-06-16 | 1987-04-28 | Nalco Chemical Company | Synergistic biocide of dodecyl guanidine hydrochloride and a mixture of 5-chloro-2-methyl-4-isothiazolin-3-one |
| US4945109A (en) * | 1988-08-24 | 1990-07-31 | Buckman Laboratories International, Inc. | Ester of carbamic acid useful as a microbicide and a preservative |
| US5219875A (en) * | 1990-11-27 | 1993-06-15 | Rohm And Haas Company | Antimicrobial compositions comprising iodopropargyl butylcarbamate and 1,2-benzisothiazolin-3-one and methods of controlling microbes |
| US5250194A (en) * | 1991-02-13 | 1993-10-05 | Buckman Laboratories International, Inc. | N-dodecyl heterocyclic compounds useful as industrial microbicides and preservatives |
| ZA926535B (en) * | 1991-11-07 | 1994-09-30 | Buckman Laboraties Internation | Synergistic combinations of iodopropargyl compounds with 1,2-benzisothiazolin-3-one in controlling fungal and bacterial growth in aqueous fluids |
| DE4217881A1 (en) * | 1992-05-29 | 1993-12-02 | Henkel Kgaa | Antimicrobial active ingredient mixtures |
| AU6240294A (en) * | 1993-02-26 | 1994-09-14 | Wesley-Jessen Corporation | Method and composition for disinfecting contact lenses |
| DE4316845A1 (en) * | 1993-05-19 | 1994-11-24 | Bayer Ag | Microbicidal agents |
-
1995
- 1995-05-30 US US08/453,001 patent/US6034081A/en not_active Expired - Lifetime
-
1996
- 1996-05-23 ZA ZA964131A patent/ZA964131B/en unknown
- 1996-05-28 PT PT96916627T patent/PT857021E/en unknown
- 1996-05-28 AT AT96916627T patent/ATE247902T1/en active
- 1996-05-28 EP EP96916627A patent/EP0857021B1/en not_active Expired - Lifetime
- 1996-05-28 DE DE69629713T patent/DE69629713T2/en not_active Expired - Lifetime
- 1996-05-28 BR BR9608368A patent/BR9608368A/en not_active IP Right Cessation
- 1996-05-28 ES ES96916627T patent/ES2205033T3/en not_active Expired - Lifetime
- 1996-05-28 MX MX9709354A patent/MX9709354A/en not_active IP Right Cessation
- 1996-05-28 WO PCT/US1996/007677 patent/WO1996038043A1/en active IP Right Grant
- 1996-05-28 SK SK1608-97A patent/SK160897A3/en unknown
- 1996-05-28 CA CA002222864A patent/CA2222864C/en not_active Expired - Fee Related
- 1996-05-28 CZ CZ973780A patent/CZ378097A3/en unknown
- 1996-05-28 AU AU59315/96A patent/AU5931596A/en not_active Abandoned
- 1996-05-28 CN CN96195490A patent/CN1190869A/en active Pending
- 1996-05-28 NZ NZ309305A patent/NZ309305A/en unknown
- 1996-05-28 JP JP8536575A patent/JPH11506103A/en not_active Ceased
- 1996-05-29 AR ARP960102779A patent/AR002134A1/en unknown
-
1997
- 1997-11-28 NO NO975501A patent/NO975501L/en not_active Application Discontinuation
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