CA1087977A - Liaison d'un compose antimicrobien a un substrat contenant un hydroxyle a l'aide de chlorure cyanurique - Google Patents

Liaison d'un compose antimicrobien a un substrat contenant un hydroxyle a l'aide de chlorure cyanurique

Info

Publication number: CA1087977A
Authority: CA; Canada
Prior art keywords: antimicrobial; cyanuric chloride; substrate; chloride; antimicrobials
Prior art date: 1977-04-12
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

Application number

CA275,928A

Other languages

English (en)

Inventor

Mortimer W. Brenner

Louis Laufer

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

SCHWARZ SERVICES INTERNATIONAL Ltd

Original Assignee

SCHWARZ SERVICES INTERNATIONAL Ltd

Priority date (The priority date 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 date listed.)

1977-04-12

Filing date

1977-04-12

Publication date

1980-10-21

1977-04-12 Application filed by SCHWARZ SERVICES INTERNATIONAL Ltd filed Critical SCHWARZ SERVICES INTERNATIONAL Ltd

1977-04-12 Priority to CA275,928A priority Critical patent/CA1087977A/fr

1980-10-21 Application granted granted Critical

1980-10-21 Publication of CA1087977A publication Critical patent/CA1087977A/fr

Status Expired legal-status Critical Current

Links

MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 title claims abstract description 63
230000000845 anti-microbial effect Effects 0.000 title claims abstract description 49
239000000758 substrate Substances 0.000 title claims abstract description 49
125000002887 hydroxy group Chemical group [H]O* 0.000 title claims abstract description 14
150000001875 compounds Chemical class 0.000 title description 7
239000004599 antimicrobial Substances 0.000 claims abstract description 75
239000000203 mixture Substances 0.000 claims abstract description 20
238000000034 method Methods 0.000 claims abstract description 14
125000001453 quaternary ammonium group Chemical group 0.000 claims abstract description 12
229920002472 Starch Polymers 0.000 claims abstract description 11
150000001412 amines Chemical class 0.000 claims abstract description 11
239000010985 leather Substances 0.000 claims abstract description 11
235000019698 starch Nutrition 0.000 claims abstract description 11
239000007864 aqueous solution Substances 0.000 claims abstract description 8
229920002678 cellulose Polymers 0.000 claims abstract description 8
239000001913 cellulose Substances 0.000 claims abstract description 8
239000000460 chlorine Substances 0.000 claims abstract description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract 2
229910052801 chlorine Inorganic materials 0.000 claims abstract 2
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 71
239000000243 solution Substances 0.000 claims description 26
229960002152 chlorhexidine acetate Drugs 0.000 claims description 19
MCSINKKTEDDPNK-UHFFFAOYSA-N propyl propionate Chemical compound CCCOC(=O)CC MCSINKKTEDDPNK-UHFFFAOYSA-N 0.000 claims description 19
229960003260 chlorhexidine Drugs 0.000 claims description 15
GHXZTYHSJHQHIJ-UHFFFAOYSA-N Chlorhexidine Chemical compound C=1C=C(Cl)C=CC=1NC(N)=NC(N)=NCCCCCCN=C(N)N=C(N)NC1=CC=C(Cl)C=C1 GHXZTYHSJHQHIJ-UHFFFAOYSA-N 0.000 claims description 13
JIAPMJAWWPALPY-UHFFFAOYSA-N [Cl-].CC(CCCCCCCCC[NH2+]CCCCCCCC)(C)C Chemical compound [Cl-].CC(CCCCCCCCC[NH2+]CCCCCCCC)(C)C JIAPMJAWWPALPY-UHFFFAOYSA-N 0.000 claims description 11
WEEMDRWIKYCTQM-UHFFFAOYSA-N 2,6-dimethoxybenzenecarbothioamide Chemical compound COC1=CC=CC(OC)=C1C(N)=S WEEMDRWIKYCTQM-UHFFFAOYSA-N 0.000 claims description 7
229960002385 streptomycin sulfate Drugs 0.000 claims description 7
SXPWTBGAZSPLHA-UHFFFAOYSA-M cetalkonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 SXPWTBGAZSPLHA-UHFFFAOYSA-M 0.000 claims description 5
229960000228 cetalkonium chloride Drugs 0.000 claims description 5
PGBHMTALBVVCIT-VCIWKGPPSA-N framycetin Chemical compound N[C@@H]1[C@@H](O)[C@H](O)[C@H](CN)O[C@@H]1O[C@H]1[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](N)C[C@@H](N)[C@@H]2O)O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CN)O2)N)O[C@@H]1CO PGBHMTALBVVCIT-VCIWKGPPSA-N 0.000 claims description 5
229940053050 neomycin sulfate Drugs 0.000 claims description 5
-1 alkyl dimethyl benzyl ammonium chloride Chemical compound 0.000 claims description 4
239000012670 alkaline solution Substances 0.000 claims description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
229940022663 acetate Drugs 0.000 claims 1
230000002085 persistent effect Effects 0.000 claims 1
229920000742 Cotton Polymers 0.000 description 56
241000219146 Gossypium Species 0.000 description 55
UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 38
229910001868 water Inorganic materials 0.000 description 38
230000005764 inhibitory process Effects 0.000 description 28
239000003599 detergent Substances 0.000 description 22
238000005406 washing Methods 0.000 description 22
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
229960005322 streptomycin Drugs 0.000 description 20
235000014469 Bacillus subtilis Nutrition 0.000 description 17
230000002401 inhibitory effect Effects 0.000 description 17
241000588724 Escherichia coli Species 0.000 description 15
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
241000589517 Pseudomonas aeruginosa Species 0.000 description 14
239000012895 dilution Substances 0.000 description 12
238000010790 dilution Methods 0.000 description 12
244000206963 Saccharomyces cerevisiae var. diastaticus Species 0.000 description 11
230000000721 bacterilogical effect Effects 0.000 description 11
229910052757 nitrogen Inorganic materials 0.000 description 11
239000000126 substance Substances 0.000 description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 10
238000006243 chemical reaction Methods 0.000 description 10
238000012360 testing method Methods 0.000 description 9
244000005700 microbiome Species 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
230000000694 effects Effects 0.000 description 6
238000002474 experimental method Methods 0.000 description 6
VBIIFPGSPJYLRR-UHFFFAOYSA-M Stearyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)C VBIIFPGSPJYLRR-UHFFFAOYSA-M 0.000 description 5
239000008107 starch Substances 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
241000589516 Pseudomonas Species 0.000 description 4
230000000813 microbial effect Effects 0.000 description 4
230000035484 reaction time Effects 0.000 description 4
239000008399 tap water Substances 0.000 description 4
235000020679 tap water Nutrition 0.000 description 4
244000063299 Bacillus subtilis Species 0.000 description 3
125000006414 CCl Chemical group ClC* 0.000 description 3
238000007696 Kjeldahl method Methods 0.000 description 3
239000004098 Tetracycline Substances 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
239000004744 fabric Substances 0.000 description 3
230000017066 negative regulation of growth Effects 0.000 description 3
238000004806 packaging method and process Methods 0.000 description 3
239000000843 powder Substances 0.000 description 3
230000002829 reductive effect Effects 0.000 description 3
239000002904 solvent Substances 0.000 description 3
238000001179 sorption measurement Methods 0.000 description 3
239000004094 surface-active agent Substances 0.000 description 3
229960002180 tetracycline Drugs 0.000 description 3
229930101283 tetracycline Natural products 0.000 description 3
235000019364 tetracycline Nutrition 0.000 description 3
JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
241000894006 Bacteria Species 0.000 description 2
102000004190 Enzymes Human genes 0.000 description 2
108090000790 Enzymes Proteins 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
235000001006 Saccharomyces cerevisiae var diastaticus Nutrition 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
239000004115 Sodium Silicate Substances 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
XKXHCNPAFAXVRZ-UHFFFAOYSA-N benzylazanium;chloride Chemical compound [Cl-].[NH3+]CC1=CC=CC=C1 XKXHCNPAFAXVRZ-UHFFFAOYSA-N 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
VMKJWLXVLHBJNK-UHFFFAOYSA-N cyanuric fluoride Chemical compound FC1=NC(F)=NC(F)=N1 VMKJWLXVLHBJNK-UHFFFAOYSA-N 0.000 description 2
BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 2
239000002054 inoculum Substances 0.000 description 2
239000000463 material Substances 0.000 description 2
239000011259 mixed solution Substances 0.000 description 2
239000002304 perfume Substances 0.000 description 2
NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 2
229910052911 sodium silicate Inorganic materials 0.000 description 2
239000000725 suspension Substances 0.000 description 2
OFVLGDICTFRJMM-WESIUVDSSA-N tetracycline Chemical compound C1=CC=C2[C@](O)(C)[C@H]3C[C@H]4[C@H](N(C)C)C(O)=C(C(N)=O)C(=O)[C@@]4(O)C(O)=C3C(=O)C2=C1O OFVLGDICTFRJMM-WESIUVDSSA-N 0.000 description 2
SJADYJKMIJHMTJ-UHFFFAOYSA-N 10,10-dimethyl-N-octylundecan-1-amine Chemical compound CCCCCCCCNCCCCCCCCCC(C)(C)C SJADYJKMIJHMTJ-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
108010001478 Bacitracin Proteins 0.000 description 1
241000905957 Channa melasoma Species 0.000 description 1
241000518994 Conta Species 0.000 description 1
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
241000233866 Fungi Species 0.000 description 1
101000657326 Homo sapiens Protein TANC2 Proteins 0.000 description 1
229930193140 Neomycin Natural products 0.000 description 1
102100034784 Protein TANC2 Human genes 0.000 description 1
241000180394 Ramaria subtilis Species 0.000 description 1
229920000297 Rayon Polymers 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
206010052428 Wound Diseases 0.000 description 1
208000027418 Wounds and injury Diseases 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
229960000583 acetic acid Drugs 0.000 description 1
238000007605 air drying Methods 0.000 description 1
239000003513 alkali Substances 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
150000003868 ammonium compounds Chemical class 0.000 description 1
125000000129 anionic group Chemical group 0.000 description 1
230000002421 anti-septic effect Effects 0.000 description 1
229960003071 bacitracin Drugs 0.000 description 1
229930184125 bacitracin Natural products 0.000 description 1
CLKOFPXJLQSYAH-ABRJDSQDSA-N bacitracin A Chemical compound C1SC([C@@H](N)[C@@H](C)CC)=N[C@@H]1C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CCC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]1C(=O)N[C@H](CCCN)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2N=CNC=2)C(=O)N[C@H](CC(O)=O)C(=O)N[C@@H](CC(N)=O)C(=O)NCCCC1 CLKOFPXJLQSYAH-ABRJDSQDSA-N 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000003115 biocidal effect Effects 0.000 description 1
230000002599 biostatic effect Effects 0.000 description 1
239000007844 bleaching agent Substances 0.000 description 1
229910021538 borax Inorganic materials 0.000 description 1
235000010633 broth Nutrition 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
229920002301 cellulose acetate Polymers 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
WDRFFJWBUDTUCA-UHFFFAOYSA-N chlorhexidine acetate Chemical compound CC(O)=O.CC(O)=O.C=1C=C(Cl)C=CC=1NC(N)=NC(N)=NCCCCCCN=C(N)N=C(N)NC1=CC=C(Cl)C=C1 WDRFFJWBUDTUCA-UHFFFAOYSA-N 0.000 description 1
229960001884 chlorhexidine diacetate Drugs 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
238000004851 dishwashing Methods 0.000 description 1
235000019441 ethanol Nutrition 0.000 description 1
230000037406 food intake Effects 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
238000007654 immersion Methods 0.000 description 1
238000011534 incubation Methods 0.000 description 1
230000036512 infertility Effects 0.000 description 1
230000000670 limiting effect Effects 0.000 description 1
239000007788 liquid Substances 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
230000002906 microbiologic effect Effects 0.000 description 1
KIZODRWQLXVXLC-UHFFFAOYSA-N n-octyldecan-1-amine;hydrochloride Chemical compound [Cl-].CCCCCCCCCC[NH2+]CCCCCCCC KIZODRWQLXVXLC-UHFFFAOYSA-N 0.000 description 1
229960004927 neomycin Drugs 0.000 description 1
125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
239000006916 nutrient agar Substances 0.000 description 1
230000002688 persistence Effects 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
239000002964 rayon Substances 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000004328 sodium tetraborate Substances 0.000 description 1
235000010339 sodium tetraborate Nutrition 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
150000003522 tetracyclines Chemical class 0.000 description 1
239000004753 textile Substances 0.000 description 1

Landscapes

Agricultural Chemicals And Associated Chemicals (AREA)

CA275,928A 1977-04-12 1977-04-12 Liaison d'un compose antimicrobien a un substrat contenant un hydroxyle a l'aide de chlorure cyanurique Expired CA1087977A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA275,928A CA1087977A (fr)	1977-04-12	1977-04-12	Liaison d'un compose antimicrobien a un substrat contenant un hydroxyle a l'aide de chlorure cyanurique

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA275,928A CA1087977A (fr)	1977-04-12	1977-04-12	Liaison d'un compose antimicrobien a un substrat contenant un hydroxyle a l'aide de chlorure cyanurique

Publications (1)

Publication Number	Publication Date
CA1087977A true CA1087977A (fr)	1980-10-21

Family

ID=4108363

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA275,928A Expired CA1087977A (fr)	1977-04-12	1977-04-12	Liaison d'un compose antimicrobien a un substrat contenant un hydroxyle a l'aide de chlorure cyanurique

Country Status (1)

Country	Link
CA (1)	CA1087977A (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5817325A (en) *	1996-10-28	1998-10-06	Biopolymerix, Inc.	Contact-killing antimicrobial devices
US5849311A (en) *	1996-10-28	1998-12-15	Biopolymerix, Inc.	Contact-killing non-leaching antimicrobial materials
US5869073A (en) *	1993-12-20	1999-02-09	Biopolymerix, Inc	Antimicrobial liquid compositions and methods for using them
US7288264B1 (en)	1993-12-20	2007-10-30	Surfacine Development Company, L.L.C.	Contact-killing antimicrobial devices
CN116479655A (zh) *	2023-03-23	2023-07-25	吴江市百顺喷织有限公司	一种生物质抗菌改性涤纶面料的制备方法

1977
- 1977-04-12 CA CA275,928A patent/CA1087977A/fr not_active Expired

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5869073A (en) *	1993-12-20	1999-02-09	Biopolymerix, Inc	Antimicrobial liquid compositions and methods for using them
US6030632A (en) *	1993-12-20	2000-02-29	Biopolymerix And Surfacine Development Company	Non-leaching antimicrobial films
US6126931A (en) *	1993-12-20	2000-10-03	Surfacine Development Company, Llc	Contact-killing antimicrobial devices
US6264936B1 (en)	1993-12-20	2001-07-24	Biopolymerix, Inc.	Contact-killing non-leaching antimicrobial materials
US7288264B1 (en)	1993-12-20	2007-10-30	Surfacine Development Company, L.L.C.	Contact-killing antimicrobial devices
US5817325A (en) *	1996-10-28	1998-10-06	Biopolymerix, Inc.	Contact-killing antimicrobial devices
US5849311A (en) *	1996-10-28	1998-12-15	Biopolymerix, Inc.	Contact-killing non-leaching antimicrobial materials
CN116479655A (zh) *	2023-03-23	2023-07-25	吴江市百顺喷织有限公司	一种生物质抗菌改性涤纶面料的制备方法

Legal Events

Date	Code	Title	Description
1997-10-21	MKEX	Expiry

Publication	Publication Date	Title
US4035146A (en)	1977-07-12	Binding of antimicrobial compounds to a hydroxyl containing substrate with cyanuric chloride
US5104649A (en)	1992-04-14	Surface-functionalized biocidal polymers
Ibrahim et al.	2021	Antimicrobial agents for textiles: types, mechanisms and analysis standards
US4655756A (en)	1987-04-07	Treated non-woven material
US5359104A (en)	1994-10-25	Solid antimicrobial
CN102459747B (zh)	2015-09-30	包含过氧化物的抗菌纺织物
AU2007217780B2 (en)	2013-10-03	Generation of antimicrobial surfaces using dendrimer biocides
EP0204312A1 (fr)	1986-12-10	Méthode pour communiquer une activité antimicrobienne à des acryliques
EP2694721A1 (fr)	2014-02-12	Procédé pour le traitement de textiles synthétiques par des biocides cationiques
US20230096579A1 (en)	2023-03-30	Antiseptic wound dressing
EP1242669A1 (fr)	2002-09-25	Substrat textile manifestant des proprietes antimicrobiennes et n'ayant qu'une faible odeur deletere et de faibles effets irritants sur la peau
EP1830639B1 (fr)	2018-11-21	Produit antimicrobien et antiviral
US4618496A (en)	1986-10-21	Antimicrobial peat moss composition
US20030064645A1 (en)	2003-04-03	Biocidal polyester and methods
CA1087977A (fr)	1980-10-21	Liaison d'un compose antimicrobien a un substrat contenant un hydroxyle a l'aide de chlorure cyanurique
MXPA06011547A (es)	2007-04-09	Metodo para desinfectar o sanear una superficie.
Battice et al.	1985	A new technology for producing stabilized foams having antimicrobial activity
US3957863A (en)	1976-05-18	Anti-microbially active surface-active agents
Hayes et al.	1984	How antimicrobial treatment can improve nonwovens
EP0445563A2 (fr)	1991-09-11	Utilisation d'un produit antibactérien et déodorant
US3116207A (en)	1963-12-31	Process for the protection of textiles
KR0179521B1 (ko)	1999-04-01	의류용 정전지 방지제 조성물
WO2019180041A1 (fr)	2019-09-26	Stérilisant organique
JPS5911711B2 (ja)	1984-03-17	繊維製品の防カビおよび帯電防止加工方法
KR20070029955A (ko)	2007-03-15	반응성 항균제, 그의 제조방법 및 이로 처리된 항균 섬유