CN100391341C - Antiseptic composition containing iodo propinyl compound - Google Patents
Antiseptic composition containing iodo propinyl compound Download PDFInfo
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- CN100391341C CN100391341C CNB2004100908304A CN200410090830A CN100391341C CN 100391341 C CN100391341 C CN 100391341C CN B2004100908304 A CNB2004100908304 A CN B2004100908304A CN 200410090830 A CN200410090830 A CN 200410090830A CN 100391341 C CN100391341 C CN 100391341C
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- CN
- China
- Prior art keywords
- composition
- ipbc
- stabilizing agent
- compound
- castor oil
- 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 - Fee Related
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- 239000000203 mixture Substances 0.000 title claims abstract description 46
- 150000001875 compounds Chemical class 0.000 title claims abstract description 21
- 125000002346 iodo group Chemical group I* 0.000 title claims description 18
- 230000002421 anti-septic effect Effects 0.000 title claims description 13
- 239000003381 stabilizer Substances 0.000 claims abstract description 14
- 239000002904 solvent Substances 0.000 claims abstract description 11
- 239000002202 Polyethylene glycol Substances 0.000 claims abstract description 6
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229920001223 polyethylene glycol Polymers 0.000 claims abstract description 6
- 229940099451 3-iodo-2-propynylbutylcarbamate Drugs 0.000 claims description 35
- WYVVKGNFXHOCQV-UHFFFAOYSA-N 3-iodoprop-2-yn-1-yl butylcarbamate Chemical compound CCCCNC(=O)OCC#CI WYVVKGNFXHOCQV-UHFFFAOYSA-N 0.000 claims description 35
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical group CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 claims description 7
- 238000006116 polymerization reaction Methods 0.000 claims description 6
- 239000003995 emulsifying agent Substances 0.000 claims 3
- -1 iodinated propynyl compound Chemical class 0.000 abstract description 18
- 239000003755 preservative agent Substances 0.000 abstract description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 14
- 229920003171 Poly (ethylene oxide) Polymers 0.000 abstract description 8
- 239000004359 castor oil Substances 0.000 abstract description 7
- 235000019438 castor oil Nutrition 0.000 abstract description 7
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 abstract description 7
- 239000011248 coating agent Substances 0.000 abstract description 5
- 238000000576 coating method Methods 0.000 abstract description 5
- 230000000694 effects Effects 0.000 abstract description 5
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical group CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 abstract description 4
- 239000010985 leather Substances 0.000 abstract description 4
- 239000003973 paint Substances 0.000 abstract description 4
- 239000004753 textile Substances 0.000 abstract description 4
- 241000233866 Fungi Species 0.000 abstract description 3
- ALDCPEBFUITPFV-UHFFFAOYSA-N butyl n-(3-iodoprop-2-ynyl)carbamate Chemical compound CCCCOC(=O)NCC#CI ALDCPEBFUITPFV-UHFFFAOYSA-N 0.000 abstract 2
- 230000007928 solubilization Effects 0.000 abstract 2
- 238000005063 solubilization Methods 0.000 abstract 2
- 239000002023 wood Substances 0.000 abstract 1
- 230000002335 preservative effect Effects 0.000 description 10
- 239000000243 solution Substances 0.000 description 6
- 239000002131 composite material Substances 0.000 description 5
- 239000002537 cosmetic Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 229920001131 Pulp (paper) Polymers 0.000 description 3
- 241000235342 Saccharomycetes Species 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 241000894006 Bacteria Species 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 230000000843 anti-fungal effect Effects 0.000 description 2
- 235000013877 carbamide Nutrition 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 150000001469 hydantoins Chemical class 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- UXFQFBNBSPQBJW-UHFFFAOYSA-N 2-amino-2-methylpropane-1,3-diol Chemical compound OCC(N)(C)CO UXFQFBNBSPQBJW-UHFFFAOYSA-N 0.000 description 1
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 1
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
- 235000011613 Pinus brutia Nutrition 0.000 description 1
- 241000018646 Pinus brutia Species 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000002079 cooperative effect Effects 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- BEGLCMHJXHIJLR-UHFFFAOYSA-N methylisothiazolinone Chemical compound CN1SC=CC1=O BEGLCMHJXHIJLR-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229960005323 phenoxyethanol Drugs 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
Abstract
The present invention discloses a preservative agent composition containing an iodinated propynyl compound, which comprises the iodinated propynyl compound accounting for 0.2% to 30% of the total amount of the composition, 2% to 60% of solubilization stabilizing agent, and 10% to 97% of hydroxylic solvent, wherein the preferable iodinated propynyl compound is 3-iodo-2-propinyl butyl carbamate (IPBC) preferably, the solubilization stabilizing agent is polyoxyethylene castor oil or ethoxylated hydrogenated castor oil or a mixture of the polyoxyethylene castor oil and the ethoxylated hydrogenated castor oil, and the hydroxylic solvent is propylene glycol or butanediol or polyethyleneglycol or the mixture of any two of the compounds. The composition with good water solubility can be conveniently compounded with other preservative agents at will. The composition as a preservative agent is widely used in the fields of personal care products, household articles, coating, paint, leather, pulp, wood, textiles, etc., and has special effects on fungi.
Description
Technical field
The present invention relates to a kind of antiseptic composition, especially relate to the stable antiseptic composition of forming by iodo propinyl compound, solubilising stabilizing agent and hydroxylic solvent.
Background technology
Iodo propinyl compound, as derived from the ester of iodo propinyl, ether, acetal, carbamate, carbonic ester etc., 3-iodo-2-propynyl butyl carbamate (hereinafter to be referred as IPBC) particularly has very excellent antifungal (mould, the saccharomycete) activity that presses down.The fields such as personal-care supplies, household articles, coating, paint, leather, paper pulp, timber, textile that can be applicable to are as preservative.The IPBC antifungal activity is outstanding, and the antifungi performance is better than the parabens used always greatly, can with composite uses such as other preservative such as cloth sieve bohr, triumphant pine, imidazolidinyl ureas, hydantoins, have good collaborative antiseptic effect.United States Patent (USP) 5631273 discloses a kind of water miscible liquid preservative composition, is made up of single or many methylol compound, IPBC and propane diols (or butanediol), and wherein the content of IPBC may be up to 0.55%.United States Patent (USP) 5965594 discloses a kind of preferable water dispersible that has, the main liquid preservative solution of forming by dihydroxymethyl dimethyl hydantoin (DMDMH), IPBC and Phenoxyethanol, and wherein the content of IPBC may be up to 1.25%.United States Patent (USP) 6143204 discloses a kind of liquid preservative preparation of mainly being made up of DMDMH, IPBC, stabilizing agent (hydantoins, urea or derivatives thereof) and propane diols (or butanediol), and wherein IPBC may be up to 20%, is preferably 1～5%.
IPBC forms compound with other preservative to use in these prior aries, make this compound have better water solubility, and then IPBC must be controlled at below the lower amount.This dissolubility in organic solvents such as ethanol, methyl alcohol, isopropyl alcohol, propane diols, butanediol, polyethylene glycol of IPBC is better, but the dissolubility in water and water prescription is relatively poor.The effective addition of pure IPBC in cosmetics is generally 0.01～0.1%, and the addition in other industries such as coating can be to 0.5%, and only is 0.016% (literature value, the embodiment of this specification shows lower) under its solvability normal temperature in water.Pure product IPBC generally only is suitable for using in the prescription pure, that oiliness thing content is higher because of the restriction of solvability.In water prescription, if will directly use IPBC, generally be that the alcoholic solvent that earlier IPBC is dissolved in propane diols and so on adds in the entry again, institute joins solution I PBC content and is difficult to surpass 0.02%, can not obviously improve its solubility property; Even like this, IPBC still is easy to separate out, or separates out in the put procedure of product.The characteristics of poorly water-soluble have influenced the use of IPBC greatly.
Summary of the invention
The purpose of this invention is to provide a kind of antiseptic composition that contains iodo propinyl compound, good water solubility, the user can be composite by oneself requirement and other preservative, uses as preservative in the prescription of the various water content of convenient adding.
For reaching goal of the invention, the solution that the present invention adopts is iodo propinyl compound and specific solubilising stabilizing agent and the convenient stabilizing solution that uses of hydroxylic solvent composition finite concentration, thereby the water-soluble of iodo propinyl compound increased greatly, can measure any use on demand.
According to the present invention, the foregoing preservatives composition is by the iodo propinyl compound that accounts for total composition 0.2～30%, 2～60% solubilising stabilizing agent, and 10～97% hydroxylic solvent is formed.Iodo propinyl compound among the present invention can be ester derived from iodo propinyl, ether, acetal, carbamate, carbonic ester etc., serves as preferred with 3-iodo-2-propynyl butyl carbamate (IPBC) wherein.Solubilising stabilizing agent among the present invention is polyoxyethylene (n
1) castor oil, polyoxyethylene (n
2) rilanit special, and the mixture of the two; During for the two mixture, polyoxyethylene (n
1) castor oil and polyoxyethylene (n
2) ratio (weight ratio) of rilanit special can change between 1: 0.3～1: 4; Polyoxyethylene (n
1) polyoxyethylated polymerization degree n in the castor oil
1Be 35～60; Polyoxyethylene (n
2) polyoxyethylated polymerization degree n in the rilanit special
2Be 35～60; If n
1Or n
2Less than 35, then composition is water-soluble with variation; Greater than 60, then composition is solid-state at normal temperatures, is difficult for preparation and use.Hydroxylic solvent among the present invention is a propane diols, butanediol, polyethylene glycol (n
3), reach the wherein mixture of the two; Polyethylene glycol (n
3) polymerization degree n
3＜12; If n
3＞12, then composition is solid-state at normal temperatures, is difficult for preparation and use.
The antiseptic composition that the present invention proposes is easy to preparation, uses method known to a person of ordinary skill in the art, only needs with iodo propinyl compound, solubilising stabilizing agent and hydroxylic solvent at a certain temperature, mixes the formation homogeneous phase solution to scale and gets final product.
The composition that the present invention proposes is actually and has improved the solvability of IPBC in water greatly owing to water-soluble splendid; Also because of the synergistic effect between the component, composition makes IPBC also obviously improve the actual bacteriostasis of fungi; Can be widely used in fields such as personal-care supplies, household articles, coating, paint, leather, paper pulp, timber, textile as preservative.As a kind of additive, the cosmetics health standard both domestic and external all addition of regulation IPBC in cosmetic formulations is generally 0.01～0.05%, the highlyest is no more than 0.1%; Indivedual daily use chemicals industries can be added into 0.5%.The composition that the present invention proposes can satisfy the needs of IPBC practical application fully under less addition.Particularly in the higher occasion of water content, in the production as various wet towels, hygenic towelette etc., situations such as the visual raw material of user, equipment, environment, season are by oneself requirement and the composite use of other preservative, and are very convenient, be easy to add, and stability are good.
The following stated embodiment describes the present invention in detail.In these embodiments, all consumptions and ratio are all by weight.
Embodiment
Embodiment 1
Table 1. inventory of respectively filling a prescription
In the 250ml there-necked flask of band stirring, thermometer, the inventory of pressing each prescription of table 1 adds hydroxylic solvent and solubilising stabilizing agent, is heated to 50 ℃ under stirring, and adds IPBC again, keeps about 50 ℃, stirs to molten entirely, promptly gets stable antiseptic composition.Resulting composition is water-soluble splendid, is highly susceptible to using in various occasions.
Embodiment 2
Investigate the pure product of IPBC (〉=99%), 10%IPBC-propylene glycol solution and embodiment 1 part compound composition (25 ℃) water-soluble at normal temperatures, the results are shown in Table 2.
The water-soluble observation of table 2.
By table 2 as seen, the composition that the present invention proposes can improve the actual dissolubility of IPBC in water greatly, and IPBC is only soluble in propane diols and adds in the entry again and can not obviously improve its solubility property.As a kind of additive, the cosmetics health standard both domestic and external all addition of regulation IPBC in cosmetic formulations is generally 0.01～0.05%, the highlyest is no more than 0.1%; Indivedual daily use chemicals industries can be added into 0.5%.As seen the composition of the present invention's proposition can satisfy the needs of IPBC practical application fully under less addition.
Embodiment 3
The pure product of IPBC (〉=99%), 1
#And the minimum inhibitory concentration (MIC value) of 5# compound composition, measure by spread plate (to mould, saccharomycete) and dilution cultivation (to bacterium), the results are shown in Table 3.
Table 3. minimum inhibitory concentration (MIC value) ppm
As seen from Table 3, because the synergy between component, under same activity concentration, the composition that the present invention proposes, its actual antibacterial efficient (particularly to mould, saccharomycete) is higher than the pure product of IPBC.
Embodiment 4
With 5
#Compound composition and other waterborne-type preservation such as 2-bromo-2 nitros-1, ammediol (cloth sieve bohr), 2-methyl-4-isothiazoline-3-ketone (Sang Pu MIT) etc. are composite, are used for the anticorrosion of wet towel, hygenic towelette, and effect is good, the results are shown in Table 4.
Composite application of table 4. and effect
Advantage of the present invention is: composition is because water-soluble splendid, is actually greatly to have improved IPBC and exist Solubility in the water; Also because of the cooperative effect between the component, composition makes IPBC press down the reality of fungi The bacterium ability also obviously improves; Can be widely used in personal-care supplies, household articles, coating, paint, The fields such as leather, paper pulp, timber, textile are as anticorrisive agent.
Claims (5)
1. antiseptic composition that contains iodo propinyl compound, it is characterized in that: described iodo propinyl compound is a 3-iodo-2-propynyl butyl carbamate, it is by the 3-iodo-2-propynyl butyl carbamate that accounts for total composition 0.2～30%, 2～60% solubilising stabilizing agent, and 10～97% hydroxylic solvent composition, described solubilising stabilizing agent is Emulsifier EL-60 or Crodaret or the mixture of the two; Described solvent is propane diols or butanediol or polyethylene glycol or the mixture of the two.
2. by the described a kind of antiseptic composition that contains iodo propinyl compound of claim 1, it is characterized in that: as the weight ratio of the Emulsifier EL-60 of solubilising stabilizing agent and Crodaret between 1: 0.3～1: 4.
3. by claim 1 or 2 described a kind of antiseptic compositions that contain iodo propinyl compound, it is characterized in that: described is 35～60 as the polyoxyethylated degree of polymerization in the Emulsifier EL-60 of solubilising stabilizing agent.
4. by claim 1 or 2 described a kind of antiseptic compositions that contain iodo propinyl compound, it is characterized in that: described is 35～60 as the polyoxyethylated degree of polymerization in the Crodaret of solubilising stabilizing agent.
5. by the described a kind of antiseptic composition that contains iodo propinyl compound of claim 1, it is characterized in that: the degree of polymerization of described polyethylene glycol＜12.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2004100908304A CN100391341C (en) | 2004-11-15 | 2004-11-15 | Antiseptic composition containing iodo propinyl compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2004100908304A CN100391341C (en) | 2004-11-15 | 2004-11-15 | Antiseptic composition containing iodo propinyl compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1775029A CN1775029A (en) | 2006-05-24 |
| CN100391341C true CN100391341C (en) | 2008-06-04 |
Family
ID=36764843
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB2004100908304A Expired - Fee Related CN100391341C (en) | 2004-11-15 | 2004-11-15 | Antiseptic composition containing iodo propinyl compound |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN100391341C (en) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101129299B (en) * | 2007-08-16 | 2010-06-23 | 峰胜集团有限公司 | Anti-dandruff composition and use thereof |
| CN101485618B (en) * | 2008-11-25 | 2012-03-28 | 南京华狮化工有限公司 | Composition and application thereof as scurf-eliminating and itch-stopping agent |
| CN101897338A (en) * | 2010-07-14 | 2010-12-01 | 铜陵高聚生物科技有限公司 | Water-soluble mildew preventive and preparation method thereof |
| CN102177901B (en) * | 2010-12-15 | 2013-05-29 | 北京桑普生物化学技术有限公司 | Sterilizing preservative composition containing benzethonium chloride and application thereof |
| JP5318272B1 (en) * | 2012-11-15 | 2013-10-16 | イーダ株式会社 | Antibacterial liquid composition |
| CN102934635B (en) * | 2012-11-16 | 2014-07-30 | 中国热带农业科学院橡胶研究所 | Environment-friendly mould-proof and anti-discoloration protective agent for rubber wood |
| CN103004887B (en) * | 2012-12-27 | 2014-11-26 | 温州医学院 | Bactericide and anti-mildew agent for straw mats and preparation method of agent |
| CN105583927A (en) * | 2014-10-21 | 2016-05-18 | 中国科学院理化技术研究所 | Antibacterial and antifungal agent for bamboos as well as application method thereof |
| CN105522628A (en) * | 2014-10-21 | 2016-04-27 | 中国科学院理化技术研究所 | Anti-bacterial and mildew-proof material for bamboo and wood products and preparation method thereof |
| CN105155341B (en) * | 2015-10-05 | 2017-03-29 | 福建农林大学 | High antibacterial paper used for sexual life of a kind of high intensity high flexibility and preparation method thereof |
| CN107242429A (en) * | 2017-07-20 | 2017-10-13 | 太仓市荣德生物技术研究所 | A kind of aquatic product bio-preservative |
| CN109267339B (en) * | 2018-09-30 | 2021-04-30 | 嘉兴学院 | Leather mildew preventive and preparation method thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1253490A (en) * | 1997-04-24 | 2000-05-17 | 约翰逊及约翰逊有限公司 | Preservative composition comprising iodopropynyl butyl carbamate and phenoxyethanol |
| CN1272765A (en) * | 1998-06-19 | 2000-11-08 | 伦萨公司 | Stabilized mixtures of iodopropargyl compound and formaldehyde donor |
-
2004
- 2004-11-15 CN CNB2004100908304A patent/CN100391341C/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1253490A (en) * | 1997-04-24 | 2000-05-17 | 约翰逊及约翰逊有限公司 | Preservative composition comprising iodopropynyl butyl carbamate and phenoxyethanol |
| CN1272765A (en) * | 1998-06-19 | 2000-11-08 | 伦萨公司 | Stabilized mixtures of iodopropargyl compound and formaldehyde donor |
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| Publication number | Publication date |
|---|---|
| CN1775029A (en) | 2006-05-24 |
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