US3255078A - Process for the treatment of fiber articles of synthetic polyamides and composition produced - Google Patents
Process for the treatment of fiber articles of synthetic polyamides and composition produced Download PDFInfo
- Publication number
- US3255078A US3255078A US123623A US12362361A US3255078A US 3255078 A US3255078 A US 3255078A US 123623 A US123623 A US 123623A US 12362361 A US12362361 A US 12362361A US 3255078 A US3255078 A US 3255078A
- Authority
- US
- United States
- Prior art keywords
- fiber articles
- synthetic polyamides
- treatment
- composition produced
- articles
- 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
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Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M16/00—Biochemical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. enzymatic
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/21—Nylon
Definitions
- the present invention relates to the treatment of fiber articles of synthetic polyamides; more particularly it concerns a process for the treament of fiber articles of synthetic polyamides which consists in treating the fiber articles with antimicrobic arylene imidazolium compounds.
- Suitable antimicrobic arylene imidazolium compounds have been described, for example, in French patent specification No. 1,248,412; they correspond to the general formula
- X represents an acid radical, for example the radical of hydrochloric acid, sulfuric acid or methylsulfuric acid or a radical of a phosphoric acid or a low molecular weight aliphatic carboxylic acid
- Y stands for an aryl radical, for instance for a phenyl or naphthyl radical which may be substituted, for example by halogen and/or hydroxyl groups, or for a heterocyclic radical, for example the furyl, pyrryl, thienyl, pyridyl, indolyl 0r quinolyl radical; one of the .substituents R and R is an alkyl radical or an esterified or amidated acid group which contains 1-4 carbon atoms and
- the textile material thus treated has an antimicrobic finish.
- the outstanding fastness to washing of this finish can be seen in the following table in which the width of'the inhibition zones which result around samples of the finished textile material placed on agar-agar plates inoculated with the various microbes given in the table before washing and after Washing several times with a commercial detergent, is indicated in millimeters.
- Example 3 Socks produced from filaments of polymeric e-caprolactam are agitated for 60 minutes in an aqueous bath having a goods-to-liquor ratio of 1:40 and containing, per liter, 50 g. of l-methyl-2-phenyl-3-dodecyl-benzimidazo1- ium bromide, the initial temperature of-40 C. being slowly raised to 98 C. The socks are finally dried. Their antimicrobic finish was also found to be very fast to washing.
- antimicrobic arylene imidazolium compounds to be used according to the invention is surprising since other known, highly active antimocrobic agents, such as quaternary ammonium compounds of the dimethyl-dodecyl-benzyl-ammonium chloride type, or halogenated dihydroxy-diphenyl compounds of the dichloro-dihydroxy-diphenyl methane type, do not yield satisfactory results in the treatment of fiber articles of synthetic polyamides.
- highly active antimocrobic agents such as quaternary ammonium compounds of the dimethyl-dodecyl-benzyl-ammonium chloride type, or halogenated dihydroxy-diphenyl compounds of the dichloro-dihydroxy-diphenyl methane type
- synthetic polyamides herein used denotes long-chain synthetic polyamides which have recurring amide groups as an integral part of the main polymer chain and which are capable of being formed into filaments; such' synthetic polyamides may be derived from hexamethylene diamine and adipic acid, from s-aminocaproic acid or from e-caprolactam (cf. Kirk-Othmer: Encyclopedia of Chemical Technology, vol. 10, New York, 1953, pages 916-917).
- Process for imparting antimicrobic properties to fiber articles of long-chain synthetic polyamides having recurring amide groups as an integralpart of the main polymer chain comprising contacting-the articles in an aqueous medium with an active amount of 1-methyl-2- phenyl-3-dodecyl-benzimidazolium bromide.
- a method for imparting antimicrobial properties to fiber articles of long-chain synthetic polyamides having recurring amide groups as an integral part of the main polymer chain comprising contacting the fiber articles with an active amount of a compound having the formula arylene :0 Y X wherein X is an acid anion; Y is phenyl; R is an alkyl of 1-4 carbon atoms; and R is an alkyl which contains about 10-12 carbon atoms, and arylene is phenyl.
- a fibrous article consisting essentially of a longchain synthetic polyamide having recurring amide groups as an integral part of the main polymer chain, said polyamide having incorporated thereon an active amount of a compound having the formula wherein X is an acid anion; Y is phenyl; R is an alkyl of 1-4 carbon atoms; and R is an alkyl which contains about 10-12 carbon atoms, and arylene is phenyl.
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- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Biochemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Microbiology (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Artificial Filaments (AREA)
- Polyamides (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Description
United States Patent Office 3,255,978 Patented June 7, 1966 3 Claims. in. 16738.6)
The present invention relates to the treatment of fiber articles of synthetic polyamides; more particularly it concerns a process for the treament of fiber articles of synthetic polyamides which consists in treating the fiber articles with antimicrobic arylene imidazolium compounds.
In this way it is possible to finish fiber articles of synthetic polyamidese such as fibers, filaments, yarns, fabrics as well as wearing apparel made therefrom, in an outstanding antimicrobic manner. Surprisingly, this finish is very fast to washing such as is required for fiber articles of synthetic polyamides. Furthermore, it is noteworthy that the textile materials treated according to the invention have a strongly deodorizing and anti-perspiration effect.
The treatment of the fiber articles is advantageously carried out in an aqueous medium and at. an elevated temperature, Suitable antimicrobic arylene imidazolium compounds have been described, for example, in French patent specification No. 1,248,412; they correspond to the general formula In this formula X represents an acid radical, for example the radical of hydrochloric acid, sulfuric acid or methylsulfuric acid or a radical of a phosphoric acid or a low molecular weight aliphatic carboxylic acid, Y stands for an aryl radical, for instance for a phenyl or naphthyl radical which may be substituted, for example by halogen and/or hydroxyl groups, or for a heterocyclic radical, for example the furyl, pyrryl, thienyl, pyridyl, indolyl 0r quinolyl radical; one of the .substituents R and R is an alkyl radical or an esterified or amidated acid group which contains 1-4 carbon atoms and the other substituent is an alkyd radical or an esterified or amidated acid Example 1 A knitted fabric of spun-dyed filaments produced from commercial synthetic polyamides is agitated at 95 C. for 60 minutes in an aqueous solution using a goods-toliquor ratio of 1:40 and containing, per liter, 2 g. of
1-methyl-2-phenyl-3dodecyl benzimidazolium bromide. The fabric is subsequently rinsed and then dried.
The textile material thus treated has an antimicrobic finish. The outstanding fastness to washing of this finish can be seen in the following table in which the width of'the inhibition zones which result around samples of the finished textile material placed on agar-agar plates inoculated with the various microbes given in the table before washing and after Washing several times with a commercial detergent, is indicated in millimeters.
Table Slc. Bet. Trichop. aureus fluoresc. mentagroph.
Before washing 3 3 5 After washing once- 3 3 4 After washing 5 times 3 3 3 Example 2 Stc. aureus 3 Bar. fluoresc. 2
Trichoph. ment. 4
Candida alb. 4
Example 3 Socks produced from filaments of polymeric e-caprolactam are agitated for 60 minutes in an aqueous bath having a goods-to-liquor ratio of 1:40 and containing, per liter, 50 g. of l-methyl-2-phenyl-3-dodecyl-benzimidazo1- ium bromide, the initial temperature of-40 C. being slowly raised to 98 C. The socks are finally dried. Their antimicrobic finish was also found to be very fast to washing.
The outstanding suitability of the antimicrobic arylene imidazolium compounds to be used according to the invention is surprising since other known, highly active antimocrobic agents, such as quaternary ammonium compounds of the dimethyl-dodecyl-benzyl-ammonium chloride type, or halogenated dihydroxy-diphenyl compounds of the dichloro-dihydroxy-diphenyl methane type, do not yield satisfactory results in the treatment of fiber articles of synthetic polyamides.
The term synthetic polyamides herein used denotes long-chain synthetic polyamides which have recurring amide groups as an integral part of the main polymer chain and which are capable of being formed into filaments; such' synthetic polyamides may be derived from hexamethylene diamine and adipic acid, from s-aminocaproic acid or from e-caprolactam (cf. Kirk-Othmer: Encyclopedia of Chemical Technology, vol. 10, New York, 1953, pages 916-917).
We claim:
1. Process for imparting antimicrobic properties to fiber articles of long-chain synthetic polyamides having recurring amide groups as an integralpart of the main polymer chain, comprising contacting-the articles in an aqueous medium with an active amount of 1-methyl-2- phenyl-3-dodecyl-benzimidazolium bromide.
2. A method for imparting antimicrobial properties to fiber articles of long-chain synthetic polyamides having recurring amide groups as an integral part of the main polymer chain, comprising contacting the fiber articles with an active amount of a compound having the formula arylene :0 Y X wherein X is an acid anion; Y is phenyl; R is an alkyl of 1-4 carbon atoms; and R is an alkyl which contains about 10-12 carbon atoms, and arylene is phenyl.
3. A fibrous article consisting essentially of a longchain synthetic polyamide having recurring amide groups as an integral part of the main polymer chain, said polyamide having incorporated thereon an active amount of a compound having the formula wherein X is an acid anion; Y is phenyl; R is an alkyl of 1-4 carbon atoms; and R is an alkyl which contains about 10-12 carbon atoms, and arylene is phenyl.
References Cited by the Examiner FOREIGN PATENTS 1,248,412 11/1960 France.
OTHER REFERENCES Goldsmith: Chem. Abst., vol. 50, 1956, page 9023g.
JULIAlN S. LEVITT, Primary Examiner.
MORRIS O. WOLK, IRVING MARCUS, Examiners.
Claims (1)
- 2. A METHOD FOR IMPARTING ANTIMICROBIAL PROPERTIES TO FIBER ARTICLES OF LONG-CHAIN SYNTHETIC POLYAMIDES HAVING RECURRING AMIDE GROUPS AS AN INTEGRAL PART OF THE MAIN POLYMER CHAIN, COMPRISING CONTACTING THE FIBER ARTICLES WITH AN ACTIVE AMOUNT OF A COMPOUND HAVING THE FORMULA
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0031754 | 1960-07-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3255078A true US3255078A (en) | 1966-06-07 |
Family
ID=7094342
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US123623A Expired - Lifetime US3255078A (en) | 1960-07-23 | 1961-07-13 | Process for the treatment of fiber articles of synthetic polyamides and composition produced |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3255078A (en) |
| BE (1) | BE606383A (en) |
| GB (1) | GB911238A (en) |
| NL (1) | NL267363A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4101654A (en) * | 1973-07-19 | 1978-07-18 | Petrolite Corporation | Microbiocidal process employing full quaternary nitrogen-heterocyclic phosphonates |
| US5869027A (en) * | 1996-04-22 | 1999-02-09 | Wood; Louis L. | Method for odor reduction |
| WO2017117678A1 (en) * | 2016-01-08 | 2017-07-13 | Simon Fraser University | Poly(phenylene) and m-terphenyl as protecting groups for benzimidazolium hydroxides |
| US11230626B2 (en) | 2016-08-04 | 2022-01-25 | Simon Fraser University | Crosslinking of hydroxide stable, polybenzimidazoliums and polyimidazoliums membranes and ionomers |
| US11299464B2 (en) | 2016-07-29 | 2022-04-12 | Simon Fraser University | Stable poly(imidazolium) hydroxides |
| US11802187B2 (en) | 2017-04-10 | 2023-10-31 | Simon Fraser University | Polyphenylenes, methods, and uses thereof |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1248412A (en) * | 1956-12-01 | 1960-11-07 | Bayer Ag | Arylidene-imidazolium compounds |
-
0
- NL NL267363D patent/NL267363A/xx unknown
-
1961
- 1961-07-12 GB GB25308/61A patent/GB911238A/en not_active Expired
- 1961-07-13 US US123623A patent/US3255078A/en not_active Expired - Lifetime
- 1961-07-20 BE BE606383A patent/BE606383A/en unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1248412A (en) * | 1956-12-01 | 1960-11-07 | Bayer Ag | Arylidene-imidazolium compounds |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4101654A (en) * | 1973-07-19 | 1978-07-18 | Petrolite Corporation | Microbiocidal process employing full quaternary nitrogen-heterocyclic phosphonates |
| US5869027A (en) * | 1996-04-22 | 1999-02-09 | Wood; Louis L. | Method for odor reduction |
| WO2017117678A1 (en) * | 2016-01-08 | 2017-07-13 | Simon Fraser University | Poly(phenylene) and m-terphenyl as protecting groups for benzimidazolium hydroxides |
| CN108473441A (en) * | 2016-01-08 | 2018-08-31 | 西蒙弗雷泽大学 | Poly- (phenylene) and meta-terphenyl of blocking group as benzimidazole hydroxide |
| US10800874B2 (en) | 2016-01-08 | 2020-10-13 | Simon Fraser University | Poly(phenylene) and m-Terphenyl as protecting groups for benzimidazolium hydroxides |
| CN108473441B (en) * | 2016-01-08 | 2021-12-21 | 西蒙弗雷泽大学 | Poly (phenylene) and m-terphenyl as protecting group for benzimidazolium hydroxide |
| US11299464B2 (en) | 2016-07-29 | 2022-04-12 | Simon Fraser University | Stable poly(imidazolium) hydroxides |
| US11230626B2 (en) | 2016-08-04 | 2022-01-25 | Simon Fraser University | Crosslinking of hydroxide stable, polybenzimidazoliums and polyimidazoliums membranes and ionomers |
| US11802187B2 (en) | 2017-04-10 | 2023-10-31 | Simon Fraser University | Polyphenylenes, methods, and uses thereof |
| US11970590B2 (en) | 2017-04-10 | 2024-04-30 | Simon Fraser University | Polyphenylenes, methods, and uses thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| NL267363A (en) | |
| GB911238A (en) | 1962-11-21 |
| BE606383A (en) | 1961-11-16 |
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