WO2007140146A2 - Antimicrobial composition of 3-iodo-2-propynylbutyl carbamate and 1,3-butylene glycol as solvent - Google Patents

Antimicrobial composition of 3-iodo-2-propynylbutyl carbamate and 1,3-butylene glycol as solvent Download PDF

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Publication number
WO2007140146A2
WO2007140146A2 PCT/US2007/069247 US2007069247W WO2007140146A2 WO 2007140146 A2 WO2007140146 A2 WO 2007140146A2 US 2007069247 W US2007069247 W US 2007069247W WO 2007140146 A2 WO2007140146 A2 WO 2007140146A2
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WO
WIPO (PCT)
Prior art keywords
personal care
butylene glycol
antimicrobial composition
care formulation
davs
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.)
Ceased
Application number
PCT/US2007/069247
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French (fr)
Other versions
WO2007140146A3 (en
Inventor
John J. Merianos
Paul Garelick
Susan M. Lindstrom
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.)
ISP Investments LLC
Original Assignee
ISP Investments LLC
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.)
Filing date
Publication date
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Publication of WO2007140146A2 publication Critical patent/WO2007140146A2/en
Anticipated expiration legal-status Critical
Publication of WO2007140146A3 publication Critical patent/WO2007140146A3/en
Ceased legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/005—Antimicrobial preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/325—Carbamic acids; Thiocarbamic acids; Anhydrides or salts thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/42—Amides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/52—Stabilizers
    • A61K2800/524—Preservatives

Definitions

  • each personal care formulation requires a preservative system that meets its specific needs, particularly for effective and safe preservation as determined by challenge testing.
  • Peg-20 Stearate (CERASYNT ® 840) 1.00 ISP Docket No. 2958PCT
  • Phase A is uniform and Phase B is at 7O 0 C slowly add Phase B to Phase A with good mixing.
  • the challenge test is a 28-day test used to verify the effectiveness of a preservative system in a persona! care formulation.
  • Selected personal care formulations were inoculated with microorganisms at the onset of testing (0 hours), then sampled at 48 hours, 7 days, 14 days, 21 days, and 28 days. At 21 days the formulations were re-inoculated with the same microorganisms.
  • Pass/fail criteria were based on modified Cosmetic, Toiletry and Fragrance Association (CTFA) protocol.
  • Example 1 Accordingly this formulation of Example 1 passed a 28-day double challenge efficacy test.
  • LiquagardTM is recommended for use in personal care products at levels between 0.1 %-0.2% within a broad phi range of 4.0- 9.0.
  • Polyquaternium-7 (CONDITIONEZE ® 7) 2.50 ISP
  • Phase A When Phase A is uniform add Phase B in the order listed with mixing.
  • Example 2 passed the 28-day double challenge efficacy test. Docket No. 2958PCT
  • Aspergillus niger 16404 1.0 x 10 6 cfu/g of product 2.4 x 10 6 cfu/g
  • Test Organism 48 Hrs 7 Da ⁇ 14 Days 21 Days 28 Davs
  • Test Organism 48 Hrs 7 Days 14 Days 21 Days 28 Days
  • Test Organism 48 Hrs 7 Da> /s 14 Davs 21 Davs 28 Davs

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Dermatology (AREA)
  • Epidemiology (AREA)
  • Birds (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Cosmetics (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

An antimicrobial composition of 3-iodo-2-propynylbutyl carbamate (IPBC) and 1,3-butylene glycol (BG) as solvent, in a defined weight ratio, preferably 9-11% IPBC and 89-91% BG, and personal care formulations including the composition in an amount of about 0.1-0.2% therein, at a pH of 4-9, is described.

Description

Docket No. 2958PCT 1
ANTIMICROBIAL COMPOSITION OF 3-IODO-2-PROPYNYLBUTYL CARBAMATE AND 1 ,3-BUTYLENE GLYCOL AS SOLVENT
CROSS-REFERENCE TO RELATED APPLICATION
[0001] The present application claims the benefit of U.S. Nonprovisional
Application Serial No. 11/439,702, filed on May 23, 2006, which is incorporated herein by reference thereto,
FIELD OF THE INVENTION
[0002] This invention relates to preservative compositions for inhibiting the growth of microorganisms and fungi in personal care and industrial applications, and, more particularly, to preservative compositions which are effective and safe, are formaldehyde-free and paraben-free, are temperature and pH stable, and have broad compatibility with raw materials present therein.
BACKGROUND OF THE INVENTION
[0003] Preservative compositions having antibacterial properties suitable for use in personal care and industrial applications have been described in the literature, see U.S. Patent Nos. 3,923,870; 4,844,891 ; 5,428,050; 5,496,842; 5,552,425; 5,631 ,273; 6,582,627; and U.S. Publication No. US2003/0039580.
[0004] However, each personal care formulation requires a preservative system that meets its specific needs, particularly for effective and safe preservation as determined by challenge testing.
SUMMARY OF THE INVENTION
[0005] What is described herein is an antimicrobial composition consisting essentially of 3-iodo-2~propynylbutyl carbamate (IPBC) in 1 ,3-butylene glycol (BG) as solvent, preferably, by wt, 9-11 % IPBC in 89-91% BG, and personal care formulations containing 0.1-0.2% by wt. of the preservative composition, at a pH of 4-9 of the composition. Docket No. 2958PCT
[0006] The preservative compositions herein are effective and safe, are formaldehyde-free and paraben-free, are temperature and pH stable, and are compatible with raw materials present in both personal care and industrial products.
DETAILED DESCRIPTION OF THE INVENTION
[0007] The invention will now be illustrated in more detail by the following examples.
EXAMPLE 1 - NON-IONIC MOISTURIZER
PHASE INGREDIENT %W/W SUPPLIER
A Deionized Water 78.70
Disodium EDTA (Versene NA) 0.10 Dow
Glycerin (and) Glyceryl Acrylate/
Acrylic Acid Copolymer (and) Butylene
Glycol (and) PVM/MA Copolymer
(LUBRAJEL® OIL BG) 0.50 ISP
Sodium Polyacrylate
(RAPΓΓΉIX® A-IOO) 0.75 isp
B Octyldodecyl Stearate
(CERAPHYL® ODS) 3.50 ISP lsostearyl Neopentanoate
(CERAPHYL® 375) 3.50 ISP
Diisopropyl Adipate
(CERAPHYL® 230) 2,50 ISP
Ethylhexyl Palmitate
(CERAPHYL® 368) 2.50 ISP
Ci2-i5A!kyl Lactate
(CERAPHYL® 41) 3.00 ISP
Glyceryl Stearate (and)
Laureth-23 (CERASYNT® 945) 1.25 ISP
Peg-20 Stearate (CERASYNT® 840) 1.00 ISP Docket No. 2958PCT
C Cyclopentasiloxane
(SI-TEC™ CM 040) 2.50 ISP
D 1 ,3-Butylene Glycol and lodopropynyl Butylcarbamate
(LIQUAGARD™) 0.20 ISP
100.00%
PROCEDURE
1. Combine Phase A except for Rapithix A-100. Sprinkle in Rapithix A-100 with good mixing.
2. Combine Phase B with mixing and heat to 700C.
3. When Phase A is uniform and Phase B is at 7O0C slowly add Phase B to Phase A with good mixing.
4. When batch is uniform add Phase C with good mixing.
5. Add Phase D and mix until the batch is completely uniform.
Challenge Tests
[0008] The challenge test is a 28-day test used to verify the effectiveness of a preservative system in a persona! care formulation. Selected personal care formulations were inoculated with microorganisms at the onset of testing (0 hours), then sampled at 48 hours, 7 days, 14 days, 21 days, and 28 days. At 21 days the formulations were re-inoculated with the same microorganisms. Pass/fail criteria were based on modified Cosmetic, Toiletry and Fragrance Association (CTFA) protocol.
[0009] The invention composition was tested in several systems and found to effectively preserve a variety of personal care formulations against the following microorganisms:
Microorganism Abbreviation
Candida albicans CAN
Aspergillus niger AN Docket No. 2958PCT
inoculum Concentration (CFU/g)
Orqanism 0 Hours 21 Davs
CAN ATCC 10231 1.9x106 5.0x105
AN ATCC 16404 3.0x105 1.0x106
Preservative Efficacy Test Results fCFU/q)
Orqanism 48 Hrs 7 Davs 14 Davs 21 Davs 28 Davs
CAN ATCC >1.0x' 106 <10 <10 1.0 x 102 <10
10231
AN ATCC <10 <10 <10 <10 <10
16404
[0010] Accordingly this formulation of Example 1 passed a 28-day double challenge efficacy test.
[0011] Based on this challenge test data, Liquagard™ is recommended for use in personal care products at levels between 0.1 %-0.2% within a broad phi range of 4.0- 9.0.
EXAMPLE 2 - SHOWER GEL
PHASE INGREDIENT %W/W SUPPLIER
A Deionized Water 51.45
Disodium EDTA 0.10 Dow Chemical
Polyquaternium-7 (CONDITIONEZE® 7) 2.50 ISP
Glycerin 2.50
Benzophenone-4 (ESCALOL® 577) 0.20 ISP
B Ammonium Lauryl Sulfate 30.00 Rhodia
Cocamidopropyi Betaine 10.00 Goldschmidt
Cocamide DEA 2.50 Cognis Docket No. 2958PCT
PEG-7 Glyceryl Cocoate 0.30 Cognis Fragrance (#01779396) 0.10 Dragoco B!ue #1 (.1 % Aq. Solution) 0.20 Warner Jenkinson
D 1 ,3-Buty!ene Glycol and lodopropynyl Butylcarbamate
(Liquagard™) 0.15 ISP 100.00%
PROCEDURE
1. Combine Phase A with mixing and begin heating to 65°C.
2. When Phase A is uniform add Phase B in the order listed with mixing.
3. Start cooϋng the batch.
4. Add Phases C & D at 3O0C with mixing.
5. QS for water loss and mix to RT.
pH = 7.6 Viscosity = 7,200 cps (Brookfieid Model RVT, TB @ 5 RPM)
Inoculum Concentration fCFU/g)
Orαanism 0 Hours 21 Davs
CAN ATCC 10231 4.9x106 6.6x106
AN ATCC 16404 1.0x106 2.4x106
Preservative Efficacy Test Results (CFU/α)
Orqanism 48 Hrs 7 Davs 14 Davs 21 Davs 28 Davs
CAN ATCC <10 <10 <10 <10 <10
10231
AN ATCC <10 <10 <10 <10 <10
16404
[0012] The formulation of Example 2 passed the 28-day double challenge efficacy test. Docket No. 2958PCT
EXAMPLE 3
Product: Shower Gei
Use Level: 0.02% Liquagard (200 ppm active IPBC)
TEST ORGANISM INOCULUM (O hours) REINOCULUM (21 davs)
Candida albicans 10231 4.9 x 106 cfu/g of product 6.6 x 106 cfu/g
Aspergillus niger 16404 1.0 x 106 cfu/g of product 2.4 x 106 cfu/g
Assay Interval
Test Orqanism 48 Hrs 7 Days 14 Days 21 Days 28 Davs
Candida albicans <10 <10 <10 <10 <10
Aspergillus niger <10 <10 <10 <10 <10
EXAMPLE 4 - SCREENING EMULSION
PHASE INGREDIENT W/W%
A Stearic acid 5.00
Mineral oil 2.50
Cetyl alcohol, NF 1.00
Ceteareth-5 0.50
Glyceryl Stearate and PEG-100 Stearate 1.50
B Dl water 87.90
Triethanolamine (99%) 1.00
1 ,3-Butylene Glycol (and) lodopropynyl Butylcarbamate (LIQUAGARD™ ) 0.10
D Citric acid 30% aqueous 0.60 Docket No. 2958PCT
PROCEDURE
1. Heat Phase A to 750C. Heat Phase B to 750C.
2. Add Phase A to B under moderate sheer with overhead mixer. Remove heat and continue mixing throughout preparation.
3. Add Phase C at the appropriate temperature (0C).
4. Add Phase D at 35-400C.
5. Cool to 30-350C.
6. QS with water. Remove contents to a storage container reserving enough in the beaker to measure a pH. Store in refrigerator.
EXAMPLE 5 - Antifungal Efficacy Data Formulation: Screening Emulsion
Liquagard: 10% IPBC in 1 ,3 butylene glycol
Test Method: MLM 100-9
[0013] Inoculate formulation at 0 hours. Assay at 48 hours, 7 days, 14 days, 21 days. Re-inoculate at 21 days and then final assay at 28 days. Inoculum counts are listed in Table I. Two levels of Liquagard were tested; the data is contained in Tables Il and 111 below.
TABLE I
TEST ORGANISM INOCULUM (0 hours) REINOCULUM (21 davs)
Aspergillus niger 16404 2.0 x 105 cfu/g 3.8 x 105 cfu/g
Taloromyces luteus 3.9 x 104 [ cfu/g 4.0 x 106 cfu/g
Candida albicans 10231 2.0 x 106 cfu/g 1.5 x 106 cfu/g
TABLE Il
0.05% Liαuaαard (50 DDm IPBC)
Test Organism 48 Hrs 7 Da^ 14 Days 21 Days 28 Davs
A. niger <10 <10 <10 <10 <10
T. luteus <10 <10 <10 <10 <10
C. albicans <10 <10 <10 <10 <10 Docket No. 2958PCT
TABLE IiI
0.1 % Liquaqard (100 ppm IPBC)
Test Organism 48 Hrs 7 Days 14 Days 21 Days 28 Days
A. niger <10 <10 <10 <10 <10
T. luteus <10 <10 <10 <10 <10
C. albicans <10 <10 <10 <10 <10
EXAMPLE 6 - LIQUAGARD vs CONTROLS Product: Screening emulsion
Use Level: 100 ppm active IPBC
TEST ORGANISM INOCULUM (0 hours) REINOCULUM (21 davs)
Candida albicans 10231 7.2 x 106 cfu/g of product 3.0 x 106 cfu/g
Aspergillus niger 16404 1.5 x 106 cfu/g of product 7.0 x 105 cfu/g
Assay Interval
Test Orqanism 48 Hrs 7 Da^ /s 14 Days 21 Da vs 28 Davs
Liquagard™
Candida albicans <10 <10 <10 <10 <10
Aspergillus niger <10 <10 <10 <10 <10
Glycacil L* (Lonza)
Candida albicans <10 <10 <10 <10 <10
Aspergillus niger <10 <10 <10 <10 <10
Unpreserved
Candida albicans >1 E6 >1E6 >1 E6
Aspergillus niger >1E6 >1 E6 >1E6
* Glycacil L - polyethylene glycol monococoate (-40%), polyethylene glycol dicocoate (-40%), 3-iodo-2-propynyl butyl carbamate (-10%) and polyethylene glycol (-10%). Docket No. 2958PCT
EXAMPLE 7 - NON-IONIC EMULSION
PHASE INGREDIENT %W/W SUPPLIER
A Deionized Water 70.10
PVM/MA Decadiene Crosspolymer (Stabileze® QM) 0.20 ISP
B Ethylhexyl Palmitate (Ceraphy!® 368) 10.00 ISP
Cetearyl Alcohol and Ceteareth-20 (Promulgen D) 2.00 Amerchol
Glyceryl Stearate and Laureth 23 (Cerasynt® 945) 2.50 ISP lsocetyl Stearate (Ceraphyl® 494) 10.00 ISP
Triethanolamine (99%) 0.20 Deionized Water qs
1 ,3-Butylene Glycol and lodopropynyl Butylcarbamate (Liquagard™) 0.20 ISP
100.00%
PROCEDURE
1. Sprinkle Stabileze® into water with stirring at RT. Heat phase A to 750C.
2. Combine Phase B, heat to 85°C.
3. Combine Phase B to A with stirring, at 750C.
4. When batch is uniform add Phase C.
5. When uniform turn off heat.
6. Continue stirring thru cool down.
7. Make up water loss and stir at RT. Store in refrigerator. Docket No. 2958PCT
10
EXAMPLE 8 - LlQUAGARD vs CONTROLS Product: Nonionic Emulsion
Use Level: 200 ppm active IPBC
TEST ORGANISM INOCULUM (0 hours) REINOCULUM (21 davs)
Candida albicans 10231 7.2 x 106 cfu/g of product 3.0 x 106 cfu/g
Aspergillus niger 16404 1.5 x 10fl cfu/g of product 7.0 x 105 cfu/g
Assay Interval
Test Organism 48 Hrs 7 Da> /s 14 Davs 21 Davs 28 Davs
Liquagard™
Candida albicans 3.1x104 <10 <10 <10 <10
Aspergillus niger 5.0x104 <10 <10 <10 <10
Control - Glycacil L
Candida albicans 8.5x105 <10 <10 <10 3.OxIO1
Asoerαillus niαer 1.9x105 <10 <10 <10 <10
Unpreserved
Candida albicans >1.E6 >1E6 >1E6
Aspergillus niger >1E6 >1E6 >1 E6
[0014] In summary, the invention Liquagard™ (ISP) composition can be effectively used in personal care compositions including:
[0015] Skin Care Compositions: Sunscreen creams and lotions; moisturizers; night creams; hand/body creams and lotions; shaving products; cleansing products; wipes; foundations; concealers; body washes; shower gels; liquid hand soaps and baby products.
[0016] Hair Care Compositions - Shampoos, conditioners; deep conditioning treatments; styling gels, mousses, shine lotions, hair colorants and baby products. Docket No. 2958PCT 11
[0017] While the invention has been described with particular reference to certain embodiments thereof, it will be understood that changes and modifications may be made which are within the skill of the art.

Claims

Docket No. 2958PCT 12CLAIMSWhat is claimed:
1. An antimicrobial composition consisting essentially of 3-iodo-2- propynylbutyl carbamate (IPBC) in 1 ,3-butylene glycol as solvent.
2. An antimicrobial composition according to claim 1 consisting essentially of, by wt,, 9-11% IPBC and 89-91% 1 ,3-butylene glycol.
3. A personal care formulation including the antimicrobial composition of Claim 1.
4. A personal care formulation containing 0.1-0.2% by wt. of the composition of Claim 2.
5. A personal care formulation according to Claim 4 at a pH of 4-9.
6. A personal care formulation according to Claim 3 which is a skin care product.
7. A personal care formulation according to Claim 3 which is a hair care product.
8. A personal care formulation according to claim 6 which is a non-ionic moisturizer.
9. A personal care formulation according to Claim 3 which is a shower gel.
10. A personal care formulation according to Claim 3 which is a screening emulsion.
11. A personal care formulation according to Claim 3 which is a non-ionic emulsion.
12. An industrial product which includes the antimicrobial composition of Claim 1.
PCT/US2007/069247 2006-05-23 2007-05-18 Antimicrobial composition of 3-iodo-2-propynylbutyl carbamate and 1,3-butylene glycol as solvent Ceased WO2007140146A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US11/439,702 US7740876B2 (en) 2006-05-23 2006-05-23 Antimicrobial composition of 3-iodo-2-propynylbutyl carbamate and 1,3-butylene glycol as solvent
US11/439,702 2006-05-23

Publications (2)

Publication Number Publication Date
WO2007140146A2 true WO2007140146A2 (en) 2007-12-06
WO2007140146A3 WO2007140146A3 (en) 2009-04-02

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WO (1) WO2007140146A2 (en)

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Publication number Priority date Publication date Assignee Title
GB0911951D0 (en) * 2009-07-09 2009-08-19 Reckitt & Colman Overseas Viscous topical antimicrobial compositions
CN102461496B (en) * 2010-11-17 2014-10-29 民政部一零一研究所 Low-toxicity, environment-friendly short-term remains preservative and usage thereof
CN102524240B (en) * 2010-12-10 2014-10-29 民政部一零一研究所 Efficient and environment-friendly remains preservative and application thereof
BR102018005599A2 (en) * 2018-03-21 2019-10-08 Pedro Barboza Da Rocha HAZARDOUS, HYDRATING, MOISTURIZING AND EMOLIENT COMPOSITION FOR TOPIC ADMINISTRATION IN INTERTRIGO SKIN INJURIES, SKIN INJURY AND FECAL INJURY AND OTHER RELATED INJURY.

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5552425A (en) * 1994-04-28 1996-09-03 Isp Chemicals Inc. Synergistic water soluble preservative compositions of biocidal mixtures
WO2002067685A1 (en) * 2001-02-26 2002-09-06 Lonza Inc. Stable preservative formulations comprising halopropynyl compounds and butoxydiglycol solvent

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WO2007140146A3 (en) 2009-04-02
US20070274944A1 (en) 2007-11-29

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