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WO1997006125A1 - Reduction de l'estrogenicite de composes alcoxyles et de leurs produits - Google Patents

Reduction de l'estrogenicite de composes alcoxyles et de leurs produits Download PDF

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Publication number
WO1997006125A1
WO1997006125A1 PCT/US1996/012673 US9612673W WO9706125A1 WO 1997006125 A1 WO1997006125 A1 WO 1997006125A1 US 9612673 W US9612673 W US 9612673W WO 9706125 A1 WO9706125 A1 WO 9706125A1
Authority
WO
WIPO (PCT)
Prior art keywords
carbon atoms
alk
formula
group containing
phenyl
Prior art date
Application number
PCT/US1996/012673
Other languages
English (en)
Inventor
M. Wayne Meadows
Christie Berger
Paul Berger
Rodney Cravey
Charles Davis
Kim Friloux
Charles Green
Ying Dau-Lu
Giao Nguyen
Original Assignee
Witco Corporation
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
Application filed by Witco Corporation filed Critical Witco Corporation
Priority to AU69509/96A priority Critical patent/AU6950996A/en
Priority to EP96930493A priority patent/EP0848694A4/fr
Priority to JP9508570A priority patent/JPH11510189A/ja
Priority to MX9800979A priority patent/MX9800979A/es
Priority to BR9610073A priority patent/BR9610073A/pt
Publication of WO1997006125A1 publication Critical patent/WO1997006125A1/fr
Priority to NO980462A priority patent/NO980462L/no

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32—Polymers modified by chemical after-treatment
    • C08G65/329—Polymers modified by chemical after-treatment with organic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/18—Ethers having an ether-oxygen atom bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C07C43/184—Ethers having an ether-oxygen atom bound to a carbon atom of a ring other than a six-membered aromatic ring to a carbon atom of a non-condensed ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
    • C07C43/04—Saturated ethers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
    • C07C43/04—Saturated ethers
    • C07C43/06—Diethyl ether
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/08—Esters of oxyacids of phosphorus
    • C07F9/09—Esters of phosphoric acids
    • C07F9/091—Esters of phosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
    • C08G65/2603—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen
    • C08G65/2606—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups
    • C08G65/2612—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups containing aromatic or arylaliphatic hydroxyl groups

Definitions

  • the present invention relates to alkoxylates, including but not limited to alkoxylates of phenolic compounds, such as, branched and linear alkylphenols, napthtol and napthtol derivatives, bisphenols, branched and linear dialkyl phenols, benzene diols, benzene triols, phenolic resins, stilbene and its derivatives, and phenylphenol.
  • phenolic compounds such as, branched and linear alkylphenols, napthtol and napthtol derivatives, bisphenols, branched and linear dialkyl phenols, benzene diols, benzene triols, phenolic resins, stilbene and its derivatives, and phenylphenol.
  • the present invention further relates to alkoxylates of alcohols, polyols, fatty acids, amines, carboxylic acids, and any other potentially alkoxylated material and relates more particularly to certain derivatives of such alkoxylates useful as, for instance, surfactants in many varied industrial applications, and as intermediates from which can be prepared other related compounds having a variety of uses in the industrial and commercial arena.
  • Alkylphenol alkoxylates and particularly alkylphenol ethoxylates, have found widespread use in a number of applications. These applications rely generally on the surfactant properties of such compounds.
  • the surfactant properties can, in turn, be tailored by appropriate selection of the alkyl substituent on the phenol group, and of the number of repeating ethoxy units
  • nonyl phenol ethoxylates are well known surfactants having a wide variety of uses; such compounds are known generically as "nonoxynol” compounds, and contain anywhere from 1 to 100 (or optionally more) repeating ethoxy units.
  • the alkylphenol ethoxylates find widespread use in cosmetics, toiletries, and in such diverse industrial applications as oil slick dispersants, deinking surfactants, metal treating, textile treatment, emulsion formation, emulsion polymerization, detergents and related cleaners, and the like.
  • alkyl phenol ethoxylates In view of the widespread use and wide variety of uses of alkyl phenol ethoxylates, coupled with the possibility that such ethoxylates may degrade, particularly biodegrade, into the corresponding alkyl phenol compounds or derivatives thereof which may prove to be estrogenic, the search for acceptable alternatives which would prove not to be precursors of possibly estrogenic materials has understandably led far afield of alkyl phenol alkoxylates.
  • compounds having a hydrophobic moiety and a hydrophilic moiety in which the hydrophilic moiety is a polyethoxy chain such as alkyl phenol alkoxylates, but characterized in that 1) a short block of propoxy and/or butoxy unit(s) extends from the hydrophobic moiety and precedes the ethoxy chain, or 2) a short block of propoxy and/or butoxy unit(s) have been inserted into the ethoxy chain or 3) propoxy and/or butoxy unit(s) have been randomly inserted into the ethoxy chain, or 4) propoxy and/or butoxy unit(s) have been added to the end of the ethoxy chain, or 5) propoxy and/or butoxy unit(s) are substituted for the ethoxy chain, exhibit the highly desirable properties of reduced or no estrogenicity in themselves and their products of degradation.
  • the present invention comprises in one aspect compounds of the formula
  • A denotes a straight-chained or branched alkyl or alkenyl group containing 1 to 18 carbon atoms, a phenyl group, a phenyl-alkenyl group wherein the alkenyl moiety contains 1 to 4 carbon atoms, a polycyclic group containing 8 to 14 carbon atoms, a polyol, an alkoxy group, or hydrogen;
  • D denotes phenoxy, oxy, phenyl, a linear or branched alkyl or alkenyl group, an amino group., or a carboxy group; x is 0 - 10; y is 1 - 10; z is 0 - 100;
  • each (O-Alk) denotes straight-chained or branched propoxy, butoxy or substituted oxirane; and R is hydrogen, sulfate, sulfonate, mono and/or diphosphate, carboxylate, mono and/or disulfosuccinate, or a salt thereof.
  • Yet another aspect of the present invention is in compounds of the formula A-D-(0-Alk) y -OH, wherein A,D, (O- Alk) and y are as defined herein, and in their use as starting materials for synthesis of compounds of formula
  • A-D-(OC 2 H 4 ) ⁇ -(0-Alk) y -(OC 2 H.) 2 -OR are useful in many commercial applications including surfactants.
  • the present invention extends to such compounds per se as well as to any of the large number of end-use formulations which can contain one or more compounds of the formula.
  • such formulations include oil field emuisifiers and
  • A- ⁇ -D- represents more generally the hydrophobic portion of the compound in which D is substituted with 1 to 4 groups denoted as A.
  • a 1 . 4 -D- can represent a wide variety of possible structures.
  • A can be:
  • alkenyl portion contains 1 to 4 carbon atoms, an example of which is benzyl;
  • -a polycyclic group containing 8 to 14 carbon atoms which can be wholly saturated, fully unsaturated, or partially saturated and partially unsaturated, such as indanyl, naphthalene, dihydronaphthalene, tetrahydronaphthalene, and analogs thereof containing cyclohexyl, cyclohexenyl, cyclopentyl or cyclopentenyl in place of the phenyl ring;
  • - hydroxyl or polyol preferably containing 2 to 6 carbon atoms and 2 to 6 hydroxyl groups; or alkoxy, preferably straight-chained or branched and containing 1 to 20 carbon atoms.
  • D can be phenoxy, oxy (that is, -0-), phenyl, a straight-chained or branched alkyl or alkenyl group containing 1 to 18 carbon atoms, an amino group, or carbonyl (that is, -C(O)-).
  • Preferred A 1-4 -D- groups include hydroxy benzylphenyl, i.e. a residue from Bisphenol A.
  • Another preferred embodiment of the molecule there depicted is a phenyl ring which is substituted with one, two or three straight-chain or branched-chain alkyl and/or alkenyl groups containing 1 to 18 carbon atoms, or can be any of the other groups described herein.
  • - A contains 4 to 12 carbon atoms.
  • compositions containing two or more different compounds of formula (1) such as compositions containing more than one structural isomer of a compound having a given number of carbon atoms, as well as compositions containing compounds corresponding to two or more different versions of formula (1).
  • the compound of formula (1) also contains a chain of 1 to 10 alkoxy units exhibiting the formula (O-Alk), wherein each (O-Alk) denotes a straight-chained or branched propyl, butyl or substituted oxirane moiety.
  • O-Alk alkoxy units
  • each (O-Alk) unit will be the same, although segments containing short blocks of poly (propoxy) and/or poly (butoxy) portions or random sequences of propoxy and/or butoxy groups are contemplated in the scope of this invention.
  • the chain composed of repeating (O-Alk) units can be terminated with a segment of 1-100 ethoxy units which is itself optionally substituted.
  • the number of repeating ethoxy units can be chosen in conjunction with the number of carbon atoms in the segment A so as to afford the desired degree of solubility in the intended medium, and to afford the desired HLB (hydrophilic-lipophilic balance (reference: Griffin, W.C, J. Soc. Cosmetic Chemists, vol. 1 (1949), p. 311), as is well known in the surfactant art. Random mixtures as well as blocks of ethoxy and propoxy and/or butoxy units are also contemplated in the scope of this invention.
  • the poly(ethoxy) capped alkyl phenol alkoxylate can be capped simply with a -H group, thereby affording a useful nonionic surfactant.
  • the compound of formula (1) can be capped with an anion such as a sulfate, sulfonate, carboxylate, phosphate group or sulfosuccinate, and salts thereof, thereby forming a useful series of anionic surfactants.
  • the anionic group can be balanced in charge by a cation M such as sodium, potassium, lithium, ammonium, or amine salt among others or left in its acid form.
  • a cation M such as sodium, potassium, lithium, ammonium, or amine salt among others or left in its acid form.
  • the particular choice of nonionic surfactant and anionic surfactant groups is well within the ability of the formulator.
  • the nonionic surfactants according to formula (1), and the anionic surfactants according to that formula all have a wide variety of uses conforming to those uses known for conventional alkyl phenol ethoxylates, as well as alkyl phenol ethoxylate carboxylates, sulfates, sulfonates, phosphates, and sulfosuccinates.
  • a significant aspect of the present invention is the applicants' discovery of methods by which alkyl phenol alkoxylates of formula (1) can be synthesized which in fact exhibit reduced or no estrogenicity in themselves and their products of degradation.
  • the synthetic method resides in incorporating propoxy and/or butoxy units into the poly(ethoxy) segment. It will be recognized of course that there are several different synthetic pathways by which a desired insertion can be accomplished. For instance, in one preferred embodiment, a precursor of the formula
  • the starting material A-D-OH is reacted with an already formed segment H(OAlk) y (OC 2 H 4 ) z OH, or in sequence with H(OAlk) y OH and then with H(OC 2 H 4 ) 2 OH, to form the final product.
  • EXAMPLE 5 (p-octylphenol + 4 EO) 1.932 kg of octyi phenol and 10.8g of a 50% aqueous solution of sodium hydroxide were charged to a reactor, which was then purged, and heated to 125°C. This mixture was dehydrated at this temperature for two hours, following which 1.652 kg of ethylene oxide was added to the reactor and allowed to react at 125°C for one hour. The resulting mixture was neutralized and removed from the reactor. Results from the aforementioned standard test procedure indicated that this material is estrogenic.
  • EXAMPLE 7 (ortho-nonylphenol + 4 EO) 1.989 kg of o-nonyl phenol and 10.8g of a 50% aqueous solution of sodium hydroxide were charged to a reactor, which was then purged, and heated to 125° C. This mixture was dehydrated at this temperature for two hours, following which 1.5959 kg of ethylene oxide was added to the reactor and allowed to react at 125°C for one hour. The resulting mixture was neutralized and removed from the reactor. Results from the aforementioned standard test procedure indicated that this material is estrogenic.
  • Examples 9-12 describe synthesis of additional compounds to exhibit reduced estrogenicity and reduced tendency to degrade to estrogenic products .
  • Examples 13 and 14 were carried out to enable a comparative assessment of estrogenicity to be made.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Detergent Compositions (AREA)

Abstract

Des composés de la formule A-D-(OC2H4)x-(O-Alk)y-(OC2H4)z-OR (1) dans laquelle A désigne un groupe alkyle ou alkényle à chaîne droite ou ramifié contenant de 1 à 18 atomes de carbone, un groupe phényle, un groupe phényle-alkényle dans lequel la fraction alkényle contient de 1 à 4 atomes de carbone, un groupe polycyclique contenant de 9 à 14 atomes de carbone, un polyol, un groupe alkoxy, ou de l'hydrogène; B désigne phénoxy, oxy, phényle, un groupe alkyle ou alkényle linéaire ou ramifié, un groupe amino, ou un groupe carbonyle; x est 0 - 10; y est 1 - 10; z est 0 - 100; chaque (O-Alk) désigne propoxy, butoxy à chaîne droite ou ramifié, ou oxyrane substitué; et R est hydrogène, sulfate, sulfonate, monophosphate, diphosphate, carboxylate, monosulfosuccinate, disulfosuccinate, ou un sel de ceux-ci, sont utiles comme tensioactifs en soi et dans toute application dans laquelle les tensioactifs correspondants éthoxylés de manière pure sont utiles, et se sont avérés présenter une estrogénicité réduite ou nulle en eux-mêmes et dans leurs produits de dégradation.
PCT/US1996/012673 1995-08-04 1996-08-02 Reduction de l'estrogenicite de composes alcoxyles et de leurs produits WO1997006125A1 (fr)

Priority Applications (6)

Application Number Priority Date Filing Date Title
AU69509/96A AU6950996A (en) 1995-08-04 1996-08-02 Reducing estrogenicity of alkoxylated compounds and products thereof
EP96930493A EP0848694A4 (fr) 1995-08-04 1996-08-02 Reduction de l'estrogenicite de composes alcoxyles et de leurs produits
JP9508570A JPH11510189A (ja) 1995-08-04 1996-08-02 アルコキシル化化合物の低下したエストロゲン作用及びそれらの生成物
MX9800979A MX9800979A (es) 1995-08-04 1996-08-02 Reductores de la estrogenicidad de compuestos alcoxilados y productos de los mismos.
BR9610073A BR9610073A (pt) 1995-08-04 1996-08-02 Redução da capacidade de gerar estrogênio dos compostos alcoxilados e seus derivados
NO980462A NO980462L (no) 1995-08-04 1998-02-03 Alkoksylerte forbindelser og produkter av disse med redusert östrogen virkning

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US51113095A 1995-08-04 1995-08-04
US08/511,130 1995-08-04

Publications (1)

Publication Number Publication Date
WO1997006125A1 true WO1997006125A1 (fr) 1997-02-20

Family

ID=24033577

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1996/012673 WO1997006125A1 (fr) 1995-08-04 1996-08-02 Reduction de l'estrogenicite de composes alcoxyles et de leurs produits

Country Status (14)

Country Link
EP (1) EP0848694A4 (fr)
JP (1) JPH11510189A (fr)
KR (1) KR19990036176A (fr)
CN (1) CN1197449A (fr)
AR (1) AR003190A1 (fr)
AU (1) AU6950996A (fr)
BR (1) BR9610073A (fr)
CA (1) CA2228133A1 (fr)
CZ (1) CZ28898A3 (fr)
MX (1) MX9800979A (fr)
NO (1) NO980462L (fr)
TW (1) TW340110B (fr)
WO (1) WO1997006125A1 (fr)
ZA (1) ZA966604B (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6939577B2 (en) * 2002-10-12 2005-09-06 Eastman Kodak Company Method of making a material
US7205268B2 (en) 2005-02-04 2007-04-17 Unilever Home & Personal Care Usa Division Of Conopco, Inc. Low-foaming liquid laundry detergent
US7291582B2 (en) 2005-09-20 2007-11-06 Conopco, Inc., D/B/A Unilever Liquid laundry detergent with an alkoxylated ester surfactant
US7977284B2 (en) * 2009-07-29 2011-07-12 Oil Chem Technologies, Inc Non-estrogenic alkylphenol derivatives

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2013528720A (ja) * 2010-03-10 2013-07-11 ビーエーエスエフ ソシエタス・ヨーロピア ブチレンオキシド−含有アルキルアルコキシレートに基づく界面活性剤を使用して鉱物油を抜き出すための方法
CN109021227A (zh) * 2018-06-25 2018-12-18 陕西科技大学 一种丙烯酸壬基酚聚氧乙烯聚氧丙烯酯及其制备方法

Citations (2)

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Publication number Priority date Publication date Assignee Title
US4267123A (en) * 1979-11-23 1981-05-12 Mobil Oil Corporation Method of preparing propane sulfonates
EP0064384A1 (fr) * 1981-04-30 1982-11-10 Mobil Oil Corporation Propanes sulfonates alcoxypolyéthoxyliques, leur procédé de préparation et leur mode d'emploi dans la récupération améliorée de pétrole

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US2903486A (en) * 1959-09-08 Karl h
US3223643A (en) * 1964-11-12 1965-12-14 Rohm & Haas Liquid acid-detergent-sanitizer composition
CA1163163A (fr) * 1980-06-23 1984-03-06 Susan C. Lappi Methode de suppression ou de reduction des mousses
US4436642A (en) * 1982-02-17 1984-03-13 Union Carbide Corporation Nonionic surfactants for automatic dishwasher detergents
BR8707843A (pt) * 1986-10-24 1989-10-03 Exxon Research Engineering Co Alquilefonois e derivados dos mesmos via alquilacao de fenol por destilados de petroleo craqueados

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4267123A (en) * 1979-11-23 1981-05-12 Mobil Oil Corporation Method of preparing propane sulfonates
EP0064384A1 (fr) * 1981-04-30 1982-11-10 Mobil Oil Corporation Propanes sulfonates alcoxypolyéthoxyliques, leur procédé de préparation et leur mode d'emploi dans la récupération améliorée de pétrole

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
AQUATIC TOXICOLOGY, 1993, Vol. 27, JOBLING et al., "Detergent Components in Sewage Effluent are Weakly Oestrogenic to Fish: An In Vitro Study Using Rainbow Trout (Oncorhynchus Mykiss) Hepatocytes", pages 361-372. *
See also references of EP0848694A4 *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6939577B2 (en) * 2002-10-12 2005-09-06 Eastman Kodak Company Method of making a material
US7205268B2 (en) 2005-02-04 2007-04-17 Unilever Home & Personal Care Usa Division Of Conopco, Inc. Low-foaming liquid laundry detergent
US7291582B2 (en) 2005-09-20 2007-11-06 Conopco, Inc., D/B/A Unilever Liquid laundry detergent with an alkoxylated ester surfactant
US7977284B2 (en) * 2009-07-29 2011-07-12 Oil Chem Technologies, Inc Non-estrogenic alkylphenol derivatives

Also Published As

Publication number Publication date
CN1197449A (zh) 1998-10-28
AR003190A1 (es) 1998-07-08
CZ28898A3 (cs) 1998-07-15
KR19990036176A (ko) 1999-05-25
EP0848694A4 (fr) 1999-08-25
CA2228133A1 (fr) 1997-02-20
AU6950996A (en) 1997-03-05
ZA966604B (en) 1997-02-18
TW340110B (en) 1998-09-11
MX9800979A (es) 1998-04-30
EP0848694A1 (fr) 1998-06-24
NO980462D0 (no) 1998-02-03
BR9610073A (pt) 1999-03-02
NO980462L (no) 1998-03-24
JPH11510189A (ja) 1999-09-07

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