US3928607A - Antibacterial composition and method employing a certain hexamethylenetetramine adduct - Google Patents
Antibacterial composition and method employing a certain hexamethylenetetramine adduct Download PDFInfo
- Publication number
- US3928607A US3928607A US403819A US40381973A US3928607A US 3928607 A US3928607 A US 3928607A US 403819 A US403819 A US 403819A US 40381973 A US40381973 A US 40381973A US 3928607 A US3928607 A US 3928607A
- Authority
- US
- United States
- Prior art keywords
- adduct
- quaternary ammonium
- hexamethylenetetramine
- grams
- product
- 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
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 title claims abstract description 58
- 235000010299 hexamethylene tetramine Nutrition 0.000 title claims abstract description 28
- 239000004312 hexamethylene tetramine Substances 0.000 title claims abstract description 28
- 238000000034 method Methods 0.000 title claims description 13
- 239000000203 mixture Substances 0.000 title claims description 13
- 230000000844 anti-bacterial effect Effects 0.000 title claims description 11
- 125000001453 quaternary ammonium group Chemical group 0.000 claims abstract description 33
- XVEASTGLHPVZNA-UHFFFAOYSA-N 3,4-dichlorobut-1-ene Chemical compound ClCC(Cl)C=C XVEASTGLHPVZNA-UHFFFAOYSA-N 0.000 claims abstract description 3
- 241000894006 Bacteria Species 0.000 claims description 8
- 230000006866 deterioration Effects 0.000 claims description 3
- 150000003863 ammonium salts Chemical group 0.000 claims 1
- 239000004599 antimicrobial Substances 0.000 abstract description 9
- 150000004820 halides Chemical class 0.000 abstract description 4
- 231100001231 less toxic Toxicity 0.000 abstract description 3
- 239000000047 product Substances 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 15
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 241000282461 Canis lupus Species 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 8
- 239000003973 paint Substances 0.000 description 7
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 235000017168 chlorine Nutrition 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- 230000001154 acute effect Effects 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 230000000845 anti-microbial effect Effects 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000012065 filter cake Substances 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 244000005700 microbiome Species 0.000 description 3
- 230000008707 rearrangement Effects 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 2
- 101150065749 Churc1 gene Proteins 0.000 description 2
- 102100038239 Protein Churchill Human genes 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- 230000001276 controlling effect Effects 0.000 description 2
- UKHVLWKBNNSRRR-ODZAUARKSA-M dowicil 200 Chemical compound [Cl-].C1N(C2)CN3CN2C[N+]1(C\C=C/Cl)C3 UKHVLWKBNNSRRR-ODZAUARKSA-M 0.000 description 2
- 230000002500 effect on skin Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 238000011081 inoculation Methods 0.000 description 2
- 239000004816 latex Substances 0.000 description 2
- 229920000126 latex Polymers 0.000 description 2
- 230000000813 microbial effect Effects 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- UOORRWUZONOOLO-OWOJBTEDSA-N (E)-1,3-dichloropropene Chemical compound ClC\C=C\Cl UOORRWUZONOOLO-OWOJBTEDSA-N 0.000 description 1
- VRTNIWBNFSHDEB-UHFFFAOYSA-N 3,3-dichloroprop-1-ene Chemical compound ClC(Cl)C=C VRTNIWBNFSHDEB-UHFFFAOYSA-N 0.000 description 1
- KNIUHBNRWZGIQQ-UHFFFAOYSA-N 7-diethoxyphosphinothioyloxy-4-methylchromen-2-one Chemical compound CC1=CC(=O)OC2=CC(OP(=S)(OCC)OCC)=CC=C21 KNIUHBNRWZGIQQ-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 239000004322 Butylated hydroxytoluene Substances 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 1
- TZVGCTDEUWQICS-UHFFFAOYSA-N [Cl].[Cl].[Cl].[Cl] Chemical compound [Cl].[Cl].[Cl].[Cl] TZVGCTDEUWQICS-UHFFFAOYSA-N 0.000 description 1
- FJUXUXYPGPMDSO-UHFFFAOYSA-N [Cl].[Cl].[Cl].[Cl].[Cl].[Cl].[Cl].[Cl] Chemical compound [Cl].[Cl].[Cl].[Cl].[Cl].[Cl].[Cl].[Cl] FJUXUXYPGPMDSO-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 125000000746 allylic group Chemical group 0.000 description 1
- XKMRRTOUMJRJIA-UHFFFAOYSA-N ammonia nh3 Chemical compound N.N XKMRRTOUMJRJIA-UHFFFAOYSA-N 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
- 229940095259 butylated hydroxytoluene Drugs 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 125000001309 chloro group Chemical class Cl* 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 230000036512 infertility Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000011499 joint compound Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- NGDSBQHTMKGUQU-UHFFFAOYSA-N methenamine hydrochloride Chemical compound Cl.C([N@@](C1)C2)[N@]3C[N@@]2C[N@@]1C3 NGDSBQHTMKGUQU-UHFFFAOYSA-N 0.000 description 1
- -1 monosubstituted ethylene Chemical group 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- UKHVLWKBNNSRRR-TYYBGVCCSA-M quaternium-15 Chemical compound [Cl-].C1N(C2)CN3CN2C[N+]1(C/C=C/Cl)C3 UKHVLWKBNNSRRR-TYYBGVCCSA-M 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- UOORRWUZONOOLO-UHFFFAOYSA-N telone II Natural products ClCC=CCl UOORRWUZONOOLO-UHFFFAOYSA-N 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000583 toxicological profile Toxicity 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- FQDIANVAWVHZIR-OWOJBTEDSA-N trans-1,4-Dichlorobutene Chemical compound ClC\C=C\CCl FQDIANVAWVHZIR-OWOJBTEDSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
- C07D487/18—Bridged systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
Definitions
- ABSTRACT A number of water-soluble, one-to-one quaternary ammonium adducts of unsaturated organic halides and dihalides with hexamethylenetetramine are known as being useful as antimicrobial agents.
- a two-to-one quaternary ammonium adduct can be prepared from hexamethylenetetramine and 3,4-dichlorobutene-1; this two-to-one adduct is a more active, less toxic antimicrobial agent than the known one-to-one quaternary ammonium adducts.
- the analytical data available on the product clearly indicates that the twoto-one quaternary ammonium adduct is formed.
- the analysis for percent ionic chlorine and percent nitrogen in the final product indicate that the two-to-one quaternary ammonium adduct is obtained according to this invention.
- nuclear magnetic resonance and infrared data indicate the product is symmetrical about the double dichlorobutene-l to form the two-to-one quaternary ammonium adduct of this invention should advantageously be carried out in an inert organic solvent in which the reactants are substantially soluble and the product is substantially insoluble.
- Suitable solvents are hydrocarbon and chlorinated hydrocarbon solvents 1 such as chloroform and perchloroethylene.
- the reaction should be conducted between 0C. and a maximum upper limit of about 130C., the decomposition point of the two-to-one quaternary ammonium adduct. There are no necessary pressure conditions for the reaction, and the reaction can thus be carried out at sub, super or normal atmospheric pressure. However, use of super atmospheric pressure reduces substantially the reaction time.
- the only two requisite reaction parameters are that 1) the reaction be carried out in an inert organic solvent in which the product is substantially insoluble and (2) the reaction temperature be maintained at less than about 130C. to avoid decomposition of the product.
- Table I on pages 5 represents a comparison of analytical data relating to the organic-ionic chlorine content of products obtained according to this invention and products obtained by varying the conditions of example 1 of the Frank patent.
- the data in Table I confirm that the product of this invention is a two-to-one rather than one-to-one quaternary ammonium adduct.
- the two-to-one adduct formed from hexamethylenetetramine and 3,4-dichlorobutene-l according to this invention is less toxic than either the Frank or Wolf one-to-one adducts.
- data comparing the toxicological character of the two-. to-one adduct of this invention to that of both the one to-one adduct of example I of Frank and the one-toone adduct prepared from hexamethylenetetramine and l,3-dichloropropene according to Wolf (available commercially as Dowicil 100 and 200) indicate the two-to-one adduct to have a significantly superior toxicological profile.
- Table III shows these comparative data for both acute dermal and acute oral LD tests. Both the acute oral LD and acute dermal LD tests were run in accordance with standard, accepted protocols.
- the two-to-one quaternary ammonium adduct of this invention is a water-soluble, non-metallic, nonphenolic antimicrobial agent effective against a broad spectrum of gram positive and gram negative microorganisms.
- the two-to-one quaternary ammonium adduct of this invention is particularly useful as an antimicrobial agent in a wide variety of water-based systems such as latex paints, resin emulsions, joint cement, adhesives, dispersed pigments and dyes, and other similar aqueous compositions.
- the two-to-one quaternary ammonium adduct of this invention is useful in the preparation and storage of systems susceptible to deterioration by microorganisms such as the common forms of bacteria.
- concentration of the adduct during use is dependent upon a number of factors including duration of storage, temperature of storage, etc. However, concentrations in the range of 0.05 to 0.20% based upon the weight of the composition have been found to be generally effective. It should be noted, however, that the minimal inhibitory concentrations vis-a-vis the common bacteria are much less than this suggested range for use under commercial conditions.
- EXAMPLE 4 The product of this invention had demonstrated especially high antibacterial performance in the preset ya tion of latex and emulsion based paints.
- the followlhg is a description of a notable paint formulation.
- the resulting paint prepared above was examined for antibacterial properties by inoculating a portion with approximately 10 organisms per ml Pseudomonas aeruginosa. Paint samples returned to sterility within 24 hours of inoculation and maintained the same degree of preservation for periods in excess of 9 months, at which time the testing was discontinued. The addition of test compound preserved the paint system against attack from microbial contamination and thereby maintained the viscosity, stability and performance characteristics of the paint.
- EXAMPLE 5 The following is a formulation for an oil-water hair dressing emulsion:
- Part A is heated to C and Part B is heated to 0C.
- Part C The test compound (Part C) is dissolved in Part B and-- the resulting solution added to Part A with good agitation.
- the mixture was perfumed at 45C and agitated until cold.
- composition prepared above was tested for microbial stability for a period of 6 months and after 6 month at 35C. Inoculation with bacterial cultures at this point showed the material still resistant to bacterial contamination.
- An aqueous composition normally susceptible to deterioration by bacteria containing the two-to-one quaternary ammonium adduct of hexamethylenetetramine and 3,4-dichlorobutene-l in an amount effective to exert antibacterial activity, said adduct having the structural formula:
- N N-CH2CH CHCH2-N N 2.
- a method of controlling bacteria comprising contacting said bacteria with the two-to-one quaternary ammonium adduct of hexamethylenetetramine and 3,4-dichlorobutene-l in an amount effective to exert antibacterial activity, said adduct having the structural formula:
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Paints Or Removers (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US403819A US3928607A (en) | 1973-10-05 | 1973-10-05 | Antibacterial composition and method employing a certain hexamethylenetetramine adduct |
| GB4324574A GB1425551A (en) | 1973-10-05 | 1974-10-04 | Hexamethylenetetramine adduct and its use as a bactericide |
| DE2447547A DE2447547C2 (de) | 1973-10-05 | 1974-10-04 | Antibakterielles Mittel |
| CA210,760A CA1025858A (en) | 1973-10-05 | 1974-10-04 | Antimicrobial product, composition and method |
| IT7469974A IT1050478B (it) | 1973-10-05 | 1974-10-04 | Prodotto antimicrobico e procedimento per la sua preparazione |
| FR7433523A FR2246560B1 (enrdf_load_stackoverflow) | 1973-10-05 | 1974-10-04 | |
| JP11433774A JPS5530685B2 (enrdf_load_stackoverflow) | 1973-10-05 | 1974-10-05 | |
| US05/527,364 US3959276A (en) | 1973-10-05 | 1974-11-26 | Antibacterial product |
| US05/800,480 USRE29883E (en) | 1973-10-05 | 1977-05-25 | Antibacterial product |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US403819A US3928607A (en) | 1973-10-05 | 1973-10-05 | Antibacterial composition and method employing a certain hexamethylenetetramine adduct |
Related Child Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US05/527,364 Division US3959276A (en) | 1973-10-05 | 1974-11-26 | Antibacterial product |
| US05/800,480 Division USRE29883E (en) | 1973-10-05 | 1977-05-25 | Antibacterial product |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3928607A true US3928607A (en) | 1975-12-23 |
Family
ID=23597112
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US403819A Expired - Lifetime US3928607A (en) | 1973-10-05 | 1973-10-05 | Antibacterial composition and method employing a certain hexamethylenetetramine adduct |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3928607A (enrdf_load_stackoverflow) |
| JP (1) | JPS5530685B2 (enrdf_load_stackoverflow) |
| CA (1) | CA1025858A (enrdf_load_stackoverflow) |
| DE (1) | DE2447547C2 (enrdf_load_stackoverflow) |
| FR (1) | FR2246560B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1425551A (enrdf_load_stackoverflow) |
| IT (1) | IT1050478B (enrdf_load_stackoverflow) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4456722A (en) * | 1982-11-09 | 1984-06-26 | Foley Lary L | Composition for control of bacteria and viruses |
| US4505831A (en) * | 1983-06-20 | 1985-03-19 | Buckman Laboratories, Inc. | Method of preservation of aqueous systems by addition to said systems of quaternary ammonium salts of hexamethylenetetramine |
| US6329206B1 (en) * | 1999-06-22 | 2001-12-11 | Henkel Corporation | Method of determining inhibitor concentrations in inhibited acidic pickling solutions |
| CN119119059A (zh) * | 2024-08-27 | 2024-12-13 | 安徽海螺材料科技股份有限公司 | 一种季铵盐催化剂、环保型可直接用于聚羧酸系混凝土外加剂合成的丙烯酸羟烷基酯的合成方法和应用 |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3228829A (en) * | 1963-11-04 | 1966-01-11 | Dow Chemical Co | Preservation of aqueous dispersions |
| US3624253A (en) * | 1970-03-05 | 1971-11-30 | Dow Chemical Co | Hexamethylenetetramine adducts with haloacetic acid esters |
| US3758464A (en) * | 1969-10-27 | 1973-09-11 | Dow Chemical Co | Process for preparing a stabilized biocidal composition |
| US3784529A (en) * | 1965-10-19 | 1974-01-08 | Owens Illinois Inc | Polymeric quaternary ammonium compounds and methods for making same |
| US3801576A (en) * | 1970-07-11 | 1974-04-02 | Bayer Ag | Aroyl-ethyl-hexaminium salts |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE694052A (enrdf_load_stackoverflow) * | 1966-02-16 | 1967-08-14 | ||
| US3760819A (en) * | 1970-09-09 | 1973-09-25 | Oreal | Permanent waving of hair with quaternary ammonium alkylating agents and ammonium thioglycolate |
| JPS4843613A (enrdf_load_stackoverflow) * | 1971-10-04 | 1973-06-23 |
-
1973
- 1973-10-05 US US403819A patent/US3928607A/en not_active Expired - Lifetime
-
1974
- 1974-10-04 GB GB4324574A patent/GB1425551A/en not_active Expired
- 1974-10-04 FR FR7433523A patent/FR2246560B1/fr not_active Expired
- 1974-10-04 IT IT7469974A patent/IT1050478B/it active
- 1974-10-04 CA CA210,760A patent/CA1025858A/en not_active Expired
- 1974-10-04 DE DE2447547A patent/DE2447547C2/de not_active Expired
- 1974-10-05 JP JP11433774A patent/JPS5530685B2/ja not_active Expired
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3228829A (en) * | 1963-11-04 | 1966-01-11 | Dow Chemical Co | Preservation of aqueous dispersions |
| US3784529A (en) * | 1965-10-19 | 1974-01-08 | Owens Illinois Inc | Polymeric quaternary ammonium compounds and methods for making same |
| US3758464A (en) * | 1969-10-27 | 1973-09-11 | Dow Chemical Co | Process for preparing a stabilized biocidal composition |
| US3624253A (en) * | 1970-03-05 | 1971-11-30 | Dow Chemical Co | Hexamethylenetetramine adducts with haloacetic acid esters |
| US3801576A (en) * | 1970-07-11 | 1974-04-02 | Bayer Ag | Aroyl-ethyl-hexaminium salts |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4456722A (en) * | 1982-11-09 | 1984-06-26 | Foley Lary L | Composition for control of bacteria and viruses |
| US4505831A (en) * | 1983-06-20 | 1985-03-19 | Buckman Laboratories, Inc. | Method of preservation of aqueous systems by addition to said systems of quaternary ammonium salts of hexamethylenetetramine |
| US6329206B1 (en) * | 1999-06-22 | 2001-12-11 | Henkel Corporation | Method of determining inhibitor concentrations in inhibited acidic pickling solutions |
| CN119119059A (zh) * | 2024-08-27 | 2024-12-13 | 安徽海螺材料科技股份有限公司 | 一种季铵盐催化剂、环保型可直接用于聚羧酸系混凝土外加剂合成的丙烯酸羟烷基酯的合成方法和应用 |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2246560A1 (enrdf_load_stackoverflow) | 1975-05-02 |
| DE2447547C2 (de) | 1986-03-13 |
| JPS5064424A (enrdf_load_stackoverflow) | 1975-05-31 |
| CA1025858A (en) | 1978-02-07 |
| DE2447547A1 (de) | 1975-06-19 |
| GB1425551A (en) | 1976-02-18 |
| JPS5530685B2 (enrdf_load_stackoverflow) | 1980-08-13 |
| FR2246560B1 (enrdf_load_stackoverflow) | 1982-01-22 |
| IT1050478B (it) | 1981-03-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| AS | Assignment |
Owner name: HULS AMERICA INC. Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNOR:COSAN CHEMICAL CORPORATION A CORPORATION OF NEW JERSEY;REEL/FRAME:005774/0876 Effective date: 19900209 |