US3579457A - Epoxide taurine condensation products and detergent compositions containing them - Google Patents
Epoxide taurine condensation products and detergent compositions containing them Download PDFInfo
- Publication number
- US3579457A US3579457A US812919A US3579457DA US3579457A US 3579457 A US3579457 A US 3579457A US 812919 A US812919 A US 812919A US 3579457D A US3579457D A US 3579457DA US 3579457 A US3579457 A US 3579457A
- Authority
- US
- United States
- Prior art keywords
- sodium
- taurine
- epoxide
- salt
- beta
- 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
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/34—Organic compounds containing sulfur
- C11D3/349—Organic compounds containing sulfur additionally containing nitrogen atoms, e.g. nitro, nitroso, amino, imino, nitrilo, nitrile groups containing compounds or their derivatives or thio urea
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/02—Anionic compounds
- C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
- C11D1/18—Sulfonic acids or sulfuric acid esters; Salts thereof derived from amino alcohols
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/02—Anionic compounds
- C11D1/37—Mixtures of compounds all of which are anionic
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/02—Inorganic compounds ; Elemental compounds
- C11D3/04—Water-soluble compounds
- C11D3/08—Silicates
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/02—Inorganic compounds ; Elemental compounds
- C11D3/04—Water-soluble compounds
- C11D3/10—Carbonates ; Bicarbonates
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/20—Organic compounds containing oxygen
- C11D3/2075—Carboxylic acids-salts thereof
- C11D3/2079—Monocarboxylic acids-salts thereof
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/20—Organic compounds containing oxygen
- C11D3/22—Carbohydrates or derivatives thereof
- C11D3/222—Natural or synthetic polysaccharides, e.g. cellulose, starch, gum, alginic acid or cyclodextrin
- C11D3/225—Natural or synthetic polysaccharides, e.g. cellulose, starch, gum, alginic acid or cyclodextrin etherified, e.g. CMC
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/02—Anionic compounds
- C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
- C11D1/22—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aromatic compounds
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/02—Anionic compounds
- C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
- C11D1/28—Sulfonation products derived from fatty acids or their derivatives, e.g. esters, amides
Definitions
- This invention relates to acyclic sulfonic acids and salts thereof and more particularly to the products from the condensation of a C -C aliphatic epoxide and a C C aliphatic epoxide with taurine to produce the corresponding N-substituted beta-hydroxyalkyl taurides and to synthetic detergent compositions containing N-substituted beta-hydroxyalkyl taurides as a partial or complete replacement for the sodium tripolyphosphate in synthetic detergent compositions.
- polyphosphates such as sodium tripolyphosphate as builders in commercial synthetic detergent formulations has become almost universal because of their synergistic action in such formulations.
- polyphosphates are perhaps most widely used in alkylbenzenesulfonate type detergents they are also used in combination with alkyl sulfates and in formulations containing both anionic and non-ionic surfactants.
- polyphosphates in their effect on detergency are many-fold. They reduce redeposition of soil particles by protective colloid action or deflocculation action, they saponify glyceride-type soils and act as bufiering agents to prevent the released fatty acids from lowering the pH of the detergent solution. They also function as neutralization agents for acidic soils and behave as sequestering agents or water-softening agents in hard water solutions. The polyphosphates, therefore, are extremely important in detergent formulations.
- the phosphates provide an environment which promotes excessive algae formation in surface waters such as ponds, streams, rivers, lakes and the like. While the phosphates may come from a number of sources, for example, the run-off from phosphate fertilized fields, the polyphosphates which have been utilized in synthetic detergent formulations also undoubtedly contribute to the overall phosphate contamination. Consequently, there has been a considerable amount of work carried on to find compounds which can be utilized to replace all or at least a part of the polyphosphates in detergents.
- epoxy taurine condensation roducts One group of compounds which have been tested for this purpose in accordance with this invention are the epoxy taurine condensation roducts.
- the condensation of chlorinated higher aliphatic alcohols with taurine or N-alkyl substituted taurine to produce epoxy taurides has been known for a number of years and it has also been suggested that these compounds be utilized as lathering agents or wetting-out agents.
- condensation product of certain epoxides with a taurine salt or with an N methyl taurine salt can be combined with certain inorganic salt buffering agents and the combination can be substituted for a part or all of the polyphosphates in a synthetic detergent formulation and provide the same functions in the formulation as the polyphosphates pro vide.
- novel sulfonic acids and salts thereof are produced by the condensation of a C -C aliphatic epoxide and a C -C aliphatic epoxide with taurine to give the corresponding N-substituted betahydroxy alkyl taurides. Further, in accordance with this invention these salts are combined With the salt of a strong base and a weak acid and the combination is used to replace a part or all of the sodium tripolyphosphate in a synthetic detergent formulation, the other components of the formulation being unchanged. There are certain standard detergent formulations widely used in the industry.
- One consists of the following ingredients in weight percent: sodium tripolyphosphate35; alkylbenzenesulfonate-20; sodium metasilicate7; sodium sulfate-37 and sodium carboxy methyl cellulosel.
- Another formulation frequently used in the industry consists of the following ingredients in weight percent: sodium tripolyphosphate-40; alkylbenzenesulfonate--20; sodium metasilicate7; sodium sulfate-31 and sodium carboxy methyl cellulose-2.
- the weight ratio of the epoxide taurine condensation product to the inorganic salt bufiering agent may range from 1:3 to 1:7 or expressed difien ently, from about 12.5 weight percent to 25 weight percent of the polyphosphate content is replaced by the epoxide taurine condensation product and the remaining 87.5 weight percent to 75 weight percent of the polyphosphate content is replaced by the inorganic salt buttering agent.
- detergent formulations such as those wherein a sulfonate is produced from an alpha olefin may be modified by the elimination or a part or all of the phosphate content of the formulation and the replacement of that amount eliminated with the same amount by weight of the combination of the epoxide taurine condensation product and the inorganic salt in the same ratios which have been described.
- the epoxide taurine salt condensation products which are used in this invention have the farmula wherein R is an alkyl radical having from 1 to 16 carbon atoms, R is hydrogen or an alkyl radical having from 1 to 15 carbon atoms, the sum of the carbon atoms in R plus R ranges from 2 to 16, M is ammonium or an alkali metal ion and R is a methyl radical, an ethyl radical or a propyl radical.
- R is an alkyl radical having from 1 to 16 carbon atoms
- R is hydrogen or an alkyl radical having from 1 to 15 carbon atoms
- M is ammonium or an alkali metal ion
- R is a methyl radical, an ethyl radical or a propyl radical.
- These diepoxide taurine salt condensation products can be produced by reacting the C to C epoxide with a taurine salt such as the sodium salt in the presence of water.
- a taurine salt such as the sodium salt
- the sodium salt is the most convenient salt
- other alkali metal or ammonium salts of taurine can be employed. Since this reaction is a condensation reac tion reaction it is preferred to employ approximately equal molar quantities of the reactants although an excess of either reactant may be used without affecting the reaction.
- This first condensation step is very rapid and is exothermic and, in general, is substantially quantitative, i.e. a theoretical yield of the condensation product is very rapid and is exothermic and, in general, is substantially quantitative, i.e. a theoretical yield of the condensation product is obtained.
- N-beta-hydroxy C -C alkyl taurine salt Evaporation of the water gives the N-beta-hydroxy C -C alkyl taurine salt. Equal molar quantities of this taurine salt condensation product is then reacted with an alkyl epoxide having from 3 to 18 carbon atoms in the molecule. It is preferred to employ a small amount of base such as aqueous sodium hydroxide together with temperature of the order of 80 C. to 120 C. with a reaction time of from 4 to 6 hours in carrying out this second condensation step.
- the final condensation product consisting of the N-beta-hydroxy C -C alkyl-N-beta-hydroxy C C alkyl taurine salt is recovered by partioning between a hydrocarbon solvent such as n-hexane and a polar solvent such as methyl alcohol. The final condensation product is obtained from the methyl alcohol layer by evaporation of the solvent.
- These diepoxide-taurine salt condensation products have the formula set forth above.
- the inorganic salt buffering agent is the salt of a strong base and a weak acid, for example sodium metasilicate, sodium carbonate, sodium bicarbonate, sodium acetate, ammonium carbonate and the like.
- Sodium metasilicate and sodium carbonate are preferred primarily because of their low cost.
- the combination of compounds of this invention can be used to replace the polyphosphates in detergent formulations wherein the surfactant is an anionic surfactant or a nonionic surfactant or a mixture of these.
- the anionic may be an alkylbenzenesulfonate wherein the alkyl radical is either branched chain (the hard or difficulty biodegradable surfactant), or a straight chain (the soft or readily biodegradable surfactant).
- the surfactant also may be other well-known commercial anionic compounds such as the alcohol sulfates or alkyl sulfonates or it may be a mixture of the alcohol sulfate or alkyl sulfonate and the alkylbenzenesulfonate, which mixture is the basis of a commercial formulation.
- the surfactant also may be a nonionic compound in the built formulation, for example, the polyalkoxy hydr'oxyamines as shown in US. Pat. No. 3,207,791 and the built formulations shown in this patent.
- the surfactant also may be a mixture of an anionic compound and a nonionic compound.
- the polyphosphates are not used as builders in cationic surfactant formulations. Consequently, the instant invention is applicable to all commercial synthetic detergent formulations wherein sodium tripolyphosphate is utilized as a builder.
- EXAMPLE I The sodium salt of N-beta-hydroxypropyl taurine was prepared by adding 47.4 grams (0.815 mole of propylene oxide into a solution of 120 grams (0.815 mole) of the sodium salt of taurine in grams of water. The reaction of the propylene oxide with the taurine salt proceeds very rapidly and exothermically. Evaporation of the Water yields the theoretical amount of the adduct, i.e. 167.4 grams of the colorless crystalline solid sodium salt of N-beta-hydroxypropyl taurine. This compound was identified and its structure was established by infrared and Nuclear Magnetic Resonance spectrographic analysis. This compound was utilized without need for purification to produce the second condensation product to be described.
- the product was identified as the sodium salt of N- beta-hydroxydecyl-N-beta -hydroxypropyl taurine. This compound was utilized without additional purification in the detergency tests to be described.
- the structure and identity of the compound was established in the manner employed in Example I, it was found to be the sodium salt of N-beta-hydroxydodecyl-N-beta-hydroxypropyl taurine.
- the potentiometric titration of the adduct consumed 95 percent of the calculated amount of 0.1 N hydrochloric acid based on the formula weight for C H NSO Na. It was found that the compound was freely soluble in water and gave copious foaming upon agitation.
- EXAMPLE III In a manner similar to Example I, 13.1 grams (0.062 mole) of 1,2-epoxy tetradecane was reacted with 13.7 grams (0.067 mole) of the sodium salt of N-beta hydroxypropyl taurine together with grams of water and 0.1 gram of sodium hydroxide. The mixture was stirred for four hours at 120 C. and thereafter it was added to 100 ml. of hexane and 100 ml. of methanol. There was recovered by evaporation of the methanol a tacky colorless solid amounting to a yield of 86.5 percent of the theoretical yield of the adduct.
- the adduct was found to be the sodium salt of N-beta hydroxytetradecyl-N- beta hydroxypropyl taurine. It was identified in the same manner as described in Example I. Evaporation of the hexane layer gave a small amount of a colorless oil which by gas/ liquid chromatographic analysis was found to be unreacted 1,2-epoxy tetradecane. A potentiometric titration of the condensation product required 92 percent of the calculated amount of 0.1 N hydrochloric acid, showing that the product had a high degree of purity. The product was easily soluble in water giving a clear solution which foamed copiously on shaking.
- EXAMPLE IV In order to show that the novel compounds of this invention such as those of Examples I, II and III can be used to replace a part or all of the polyphosphates in detergent formulations, a standard detergent formulation was prepared containing a sodium alkylbenzenesulfonate wherein the alkyl group was straight chain and ranged from 11 to 14 carbon atoms with an average of about 13.2 carbon atoms.
- This standard detergent formulation had the following composition in weight percent:
- the procedure and method of calculating detergency values differ in minor detail from that shown in Carbon Soil Removal, P. T. Vitale et al., Soap and Chemical Specialties, vol. 32, No. 6, pp. 41-44 (June 1956), and are described below.
- the Launder-Ometer consists of a spindle mechanism rotating in a hot water thermostated bath. Mason jars 1 pint capacity containing detergent, water, soiled cloth, and hard rubber balls for agitation are rotated on the spindle mechanism for a set time at a set rate in the hot water. The degree of cleaning is determined and the resulting numbers are the detergency values. These values are correlated with a standard anionic detergent having an arbitrarily assigned detergency value.
- the detergency tests are conducted in the following manner:
- the new cloth is cut into 4-inch wide strips across the bolt. Six strips are rolled up together and extracted with 500 cc. of acetone for 6 hours in a Soxhlet extraction apparatus. The strips are then removed and rinsed 3 times in distilled water, air dried until just barely damp, ironed until completely dry, and then placed in a 200 F. oven for 3 hours. At the end of this time, they are removed from the oven and set in a dessicator in a temperature and humidity controlled room.
- the strips of cloth are soiled with the following composition:
- the hydrogenated vegetable oil, mineral white oil and lampblack are mixed with sufiicient carbon tetrachloride to just dissolve the oil and fat.
- the concentrated soil slurry is then passed through a small, hand-operated homogenizer and the balance of the carbon tetrachloride added.
- About 200 ml. of soil is placed in a nine-inch evaporating dish and a strip of the cloth is passed through this rapidly and smoothly three times.
- the cloth is hung to dry at room temperature for 2 hoursil5 minutes and is then cut into 2-inch by 4-inch swatches and read photometrically.
- the photometer is calibrated against a magnesia block with the standard equal to 100.
- One-pint Mason jars are washed and set in the Launder- Ometer rack. They are each filled with 6 ml. of 5 percent by weight solution of the above-mentioned built compositions, l0 three-eighth inch diameter hard rubber balls, one soiled swatch, and enough 180 p.p.m. hardness water to make ml. of solution. The final concentration of the built composition is 0.3 percent.
- the jars are capped, set on the spindle, and rotated at 40-42 r.p.m. for 20 minutes at F. The jars are immediately removed, the height of the foam above the detergent solution in each jar is immediately noted (following one quick inversion of each jar), and the svslr(atches are dried on paper and photometer readings ta en.
- the detergency is calculated in the following way:
- V is practically a constant at 87
- R varies from 4080.
- the L value is then related to a factor to give the final detergency:
- a built polyphosphate-free synthetic detergent composition consisting essentially of:
- R has from 10 to 16 carbon atoms and R is hydrogen.
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- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Inorganic Chemistry (AREA)
- Molecular Biology (AREA)
- Detergent Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US62528167A | 1967-03-23 | 1967-03-23 | |
GB1048268 | 1968-03-04 | ||
US81291969A | 1969-04-02 | 1969-04-02 |
Publications (1)
Publication Number | Publication Date |
---|---|
US3579457A true US3579457A (en) | 1971-05-18 |
Family
ID=27256531
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US812919A Expired - Lifetime US3579457A (en) | 1967-03-23 | 1969-04-02 | Epoxide taurine condensation products and detergent compositions containing them |
Country Status (7)
Country | Link |
---|---|
US (1) | US3579457A (en) |
BE (1) | BE712691A (en) |
CA (1) | CA792798A (en) |
DE (1) | DE1668863A1 (en) |
FR (1) | FR1556816A (en) |
GB (1) | GB1229455A (en) |
NL (1) | NL6803977A (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0483627A1 (en) * | 1990-11-02 | 1992-05-06 | BASF Aktiengesellschaft | Process for the preparation of nickel-plated articles |
US20090087687A1 (en) * | 2007-09-28 | 2009-04-02 | Fujifilm Corporation | Sulfonic acid polyol compound, polyurethane resin, polyurethane resin for magnetic recording medium, and magnetic recording medium |
JP2010254918A (en) * | 2009-04-28 | 2010-11-11 | Fujifilm Corp | Mixture comprising sulfonate group-containing compound and method of manufacturing the same, solution composition, polyurethane resin, method of manufacturing the same, and magnetic recording medium |
-
0
- CA CA792798A patent/CA792798A/en not_active Expired
-
1968
- 1968-03-04 GB GB1048268A patent/GB1229455A/en not_active Expired
- 1968-03-13 DE DE19681668863 patent/DE1668863A1/en active Pending
- 1968-03-19 FR FR1556816D patent/FR1556816A/fr not_active Expired
- 1968-03-20 NL NL6803977A patent/NL6803977A/xx unknown
- 1968-03-22 BE BE712691D patent/BE712691A/xx unknown
-
1969
- 1969-04-02 US US812919A patent/US3579457A/en not_active Expired - Lifetime
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0483627A1 (en) * | 1990-11-02 | 1992-05-06 | BASF Aktiengesellschaft | Process for the preparation of nickel-plated articles |
US20090087687A1 (en) * | 2007-09-28 | 2009-04-02 | Fujifilm Corporation | Sulfonic acid polyol compound, polyurethane resin, polyurethane resin for magnetic recording medium, and magnetic recording medium |
JP2009096798A (en) * | 2007-09-28 | 2009-05-07 | Fujifilm Corp | Sulfonic acid polyol compound, polyurethane resin, polyurethane resin for magnetic recording medium, and magnetic recording medium |
US7737304B2 (en) * | 2007-09-28 | 2010-06-15 | Fujifilm Corporation | Sulfonic acid polyol compound, polyurethane resin, polyurethane resin for magnetic recording medium, and magnetic recording medium |
JP2014088365A (en) * | 2007-09-28 | 2014-05-15 | Fujifilm Corp | Sulfonic acid polyol compound, polyurethane resin, polyurethane resin for magnetic recording medium, and magnetic recording medium |
JP2010254918A (en) * | 2009-04-28 | 2010-11-11 | Fujifilm Corp | Mixture comprising sulfonate group-containing compound and method of manufacturing the same, solution composition, polyurethane resin, method of manufacturing the same, and magnetic recording medium |
Also Published As
Publication number | Publication date |
---|---|
NL6803977A (en) | 1968-09-24 |
CA792798A (en) | 1968-08-20 |
DE1668863A1 (en) | 1971-02-25 |
GB1229455A (en) | 1971-04-21 |
BE712691A (en) | 1968-09-23 |
FR1556816A (en) | 1969-02-07 |
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Owner name: ATLANTIC RICHFIELD COMPANY Free format text: MERGER AND CHANGE OF NAME;ASSIGNORS:ATLANTIC RICHFIELD COMPANY (MERGED INTO);ATLANTIC RICHFIELD DELAWARE CORPORATION (CHANGED TO);REEL/FRAME:004911/0380 Effective date: 19850314 Owner name: ARCO CHEMICAL COMPANY,PENNSYLVANIA Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:ATLANTIC RICHFIELD COMPANY;REEL/FRAME:004911/0448 Effective date: 19870831 Owner name: ARCO CHEMICAL COMPANY, 1500 MARKET STREET, PHILADE Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNOR:ATLANTIC RICHFIELD COMPANY;REEL/FRAME:004911/0448 Effective date: 19870831 |