US2626900A - Polypropylene benzene sulfonate - Google Patents
Polypropylene benzene sulfonate Download PDFInfo
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- US2626900A US2626900A US2626900DA US2626900A US 2626900 A US2626900 A US 2626900A US 2626900D A US2626900D A US 2626900DA US 2626900 A US2626900 A US 2626900A
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- Prior art keywords
- polypropylene
- benzene
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- sulfonate
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- -1 Polypropylene benzene sulfonate Polymers 0.000 title claims description 17
- 239000003599 detergent Substances 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 18
- 229920001155 polypropylene Polymers 0.000 claims description 18
- 239000004743 Polypropylene Substances 0.000 claims description 17
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 12
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 9
- 229910052938 sodium sulfate Inorganic materials 0.000 claims description 9
- 235000011152 sodium sulphate Nutrition 0.000 claims description 9
- FQENQNTWSFEDLI-UHFFFAOYSA-J sodium diphosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])([O-])=O FQENQNTWSFEDLI-UHFFFAOYSA-J 0.000 claims description 6
- 235000019818 tetrasodium diphosphate Nutrition 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- MWOBKFYERIDQSZ-UHFFFAOYSA-N benzene;sodium Chemical compound [Na].C1=CC=CC=C1 MWOBKFYERIDQSZ-UHFFFAOYSA-N 0.000 claims description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 25
- 239000000047 product Substances 0.000 description 10
- 229960003010 sodium sulfate Drugs 0.000 description 8
- 150000004996 alkyl benzenes Chemical group 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 229940077388 benzenesulfonate Drugs 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000003350 kerosene Substances 0.000 description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 230000002152 alkylating effect Effects 0.000 description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 2
- 235000011180 diphosphates Nutrition 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 229940048084 pyrophosphate Drugs 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 229940001593 sodium carbonate Drugs 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 235000017550 sodium carbonate Nutrition 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- 150000003871 sulfonates Chemical class 0.000 description 2
- 238000006277 sulfonation reaction Methods 0.000 description 2
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical group CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 1
- 208000002874 Acne Vulgaris Diseases 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 206010000496 acne Diseases 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- QPXWUAQRJLSJRT-UHFFFAOYSA-N diethoxyphosphinothioyl diethyl phosphate Chemical compound CCOP(=O)(OCC)OP(=S)(OCC)OCC QPXWUAQRJLSJRT-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 229940028444 muse Drugs 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- HWGNBUXHKFFFIH-UHFFFAOYSA-I pentasodium;[oxido(phosphonatooxy)phosphoryl] phosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O HWGNBUXHKFFFIH-UHFFFAOYSA-I 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- GMVPRGQOIOIIMI-DWKJAMRDSA-N prostaglandin E1 Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(O)=O GMVPRGQOIOIIMI-DWKJAMRDSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 235000019832 sodium triphosphate Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 235000019801 trisodium phosphate Nutrition 0.000 description 1
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 1
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
- 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
- C11D1/14—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aliphatic hydrocarbons or mono-alcohols
- C11D1/143—Sulfonic acid esters
-
- 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
-
- 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
- C11D1/14—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aliphatic hydrocarbons or mono-alcohols
- C11D1/146—Sulfuric acid esters
-
- 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
- C11D1/29—Sulfates of polyoxyalkylene ethers
-
- 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
- C11D3/046—Salts
-
- 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
- C11D3/06—Phosphates, including polyphosphates
-
- 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
- C11D3/3418—Toluene -, xylene -, cumene -, benzene - or naphthalene sulfonates or sulfates
Definitions
- alkyl benzene sulfonate detergents normally involves alkylation of benzene, sulfonation of the alkylatedbenzene, and neutralization of the sulfonic acid product. Neutralized products obtained in this manner may be used without further treatment or with only removal of water, and in this condition are effective and eiiicient detergent compositions. Such compositions normally contain between 30% and,45% of alkyl benzene sodium sulfonate, and between 55% and 70% of sodiumsulfate. In some cases the mixtures are treated for removal of the sodium sulfate to roduce alkyl benzene sodium sulfonates substantially free of inorganic salts.
- benzene has been alkylated by several methods and by several types of" alkylating compounds.
- benzene has been condensed with chlorinated kerosene fractions in the presence of an aluminum chloride condensing agent.
- Benzene has been condensed also with.
- oleflns from various sourcesfer'nploying aluminum chloride, sulfuric acid, or other suitable condensing agent.
- Olefln's employed for this alkyli tion have been obtained by dehydration of alcohols, by cracking of'petroleum products, and by polymerization processes.
- oleiins obtained by polymerizationof propylene, butylenefisobutylene and amylene have been proposed:
- the most suitable alkylating compounds are those providing alkyl groups containing between 9 and 18 carbon atoms.
- compositions of my invention comprise such "polypropylene" benzenesodium sulfonates in which the "polypropylene radicals contain an average of 13 to 15 carbon atoms, and in addition to the sulfonate. between 1 and -3 parts of sodium sulfate and between 1 and [4 parts of tetrasodium pyrophosphate for 'each part by weight of the sulfonate, these proportionsbeing determined on the dry basis.
- the products'of the invention when employed inwater atfaconcentration of 54% provide a pH between 19 and 10.4.
- Polypropylene fractions of ab0ut2 00 to -2'70" C. boiling range boiling for the most part between-210 and 260 C. have the required average molecular carbon content and contain penta- .propylenes as the major component.
- 'Such polypropylene fractions. suitable forpreparingihe products of the invention are available commercially. They are' normally produced by the superatmospheric poLvmerization of propylene 1'12 parts of 95% msoi is mixed with 42 parts of benzeneat 10 to 20 C. 65 parts of polypropylene, distilling at normal atmospheric presthe mixture is stirred for 1% hours at a temperature not above 30' C. The product is then woven cotton fabric soiled with a suspension of graphite in lubricating oil and cottonseed oil. The proportion of soil removed was determined photometrically.
- The" pH of the slurry is adjusted finally to ap'-' proximately '7 by the addition of sulfuric acid and the/slurry is then dried. Drying may be eflected by means of a drum drier or a spray drier at 110 C.
- the dry product contains about 38% of alkyl benzene-sodium sulfonate and 62% of sodium sulfate.
- the content'of alkyl benzene sodium sulfonatel and sodium sulfate may vary 5%; above'or below these values.
- a detergent composition consisting essentlally; of "polypropylene benzene sodium -.sulfonate, in .which the polypropylene radicals conv tain anaverage of between 13 and 15 carbon atoms and comprise a substantial proportion of pentapropylene" radicals, and for about. each' one part by, weight ofpolypropylenebenzene so-- dium sulfonate. (dry basis), between 1 and 3 parts. of sodium sulfate and between 5 -and,. 4-.parts.of t'etrasodiurn pyrophosphate.
- a detergent composition consisting. essential: ly of "polypropylene? benzene sodiumsulfonate, in which the polypropyleno radicals correspond substantially entirelyto. olefins boiling between 200 anda270 0., comprise as the major com ponent-pentapropylene radicals and contain an averageof between-13 and 15 carbon atoms; and for about each one part by weight of polypropylene benzene sodium sulfonate-(dry basis), .-be-, tweenf1.3, and 2'parts oi. sodium sulfate and between 1 and 8 partsf'of tetrasodium pyrophos pirate;
- composition consisting'essential ly of polypropylene" --benzene sodium sulfonat'e'; in which the polypropylene" radicals correspond substantially entirely to oleilns boiling between sdnwemdveain a standard inyolving a 200' and 270 d. and predominantly between 210 "pentapropylene radicals and contain an average of between 13 and 15 carbon atoms, and for about each one part by weight of polypropylene benzene sodium sulfonate (dry basis) about 1 /10. parts of sodium sulfate, and for each part of total sulfonate and sulfate about to 1 part of tetrasodium pyrophosphate.
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- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Detergent Compositions (AREA)
Description
latented 27, 1953 orrlcs POLYPROPYLENE BENZENE SULFONATE DETERGENT COMPOSITIONS CON- TAINING TETRASODIUM PYROPHQS- PHATE Samuel A. Russell, III, Chicago, 111., assignor to Allied Chemical-d: Dye Corporation, New York, N. Y., a corporation of New York No Drawing. Application January 29, 1949,
. Serial No. 73559 3 Claims. (cuss-13s) This invention relates to the manufacture of detergent compositions. It is particularly'concemed with improvements in detergent compositions of the alkyl benzene 'sulfonate type.
The manufacture of alkyl benzene sulfonate detergents normally involves alkylation of benzene, sulfonation of the alkylatedbenzene, and neutralization of the sulfonic acid product. Neutralized products obtained in this manner may be used without further treatment or with only removal of water, and in this condition are effective and eiiicient detergent compositions. Such compositions normally contain between 30% and,45% of alkyl benzene sodium sulfonate, and between 55% and 70% of sodiumsulfate. In some cases the mixtures are treated for removal of the sodium sulfate to roduce alkyl benzene sodium sulfonates substantially free of inorganic salts.
For the manufacture of detergents of the above types benzene has been alkylated by several methods and by several types of" alkylating compounds. For example, benzene has been condensed with chlorinated kerosene fractions in the presence of an aluminum chloride condensing agent. Benzene has been condensed also with. oleflns from various sourcesfer'nploying aluminum chloride, sulfuric acid, or other suitable condensing agent. Olefln's employed for this alkyli tion have been obtained by dehydration of alcohols, by cracking of'petroleum products, and by polymerization processes. Thus oleiins obtained by polymerizationof propylene, butylenefisobutylene and amylene have been proposed:
Regardless of the source. the most suitable alkylating compounds are those providing alkyl groups containing between 9 and 18 carbon atoms.
'Alkyl benzene sulfonate detergents have been marketed alone andalso in admixture with other detergent materials, among which may be mentioned the phosphates, such as trisodium phosphate and sodium triphosphate. -Experimental tests have demonstrated that while'such phosphates may improve some commercial alkyl-aromatic sulfonate detergents slightly, the immovement is not great. Moreover, tetrasodium pyrophosphate does not always promote the detergent action of such alkyl benzenesulionates.
as illustrated by its effect, in a normal hard I water, upon a commercially available detergent comprising alkyl benzene sulfonates derived from chlorinated kerosene and upon such; a detergent derived from polypropylene fractions having an average molecular carbon "content-"of 12 carbon atoms, as shown in Table 11 below.
- a decidedly "beneficial effect upon polypro' pylene benzene sulfonate detergents having an average of 13 to 15 carbon atoms in the polypropylene radicals and containing a substantial proportion of pentamers among 'the "polypropylene radicals. This discovery has ,led to the production of superior detergent compositions and furthermore has permitted utilizing for the production of such compositions .substantially less expensive starting-materials.
The compositions of my invention comprise such "polypropylene" benzenesodium sulfonates in which the "polypropylene radicals contain an average of 13 to 15 carbon atoms, and in addition to the sulfonate. between 1 and -3 parts of sodium sulfate and between 1 and [4 parts of tetrasodium pyrophosphate for 'each part by weight of the sulfonate, these proportionsbeing determined on the dry basis. The products'of the invention when employed inwater atfaconcentration of 54% provide a pH between 19 and 10.4.
Polypropylene fractions of ab0ut2 00 to -2'70" C. boiling range boiling for the most part between-210 and 260 C. have the required average molecular carbon content and contain penta- .propylenes as the major component. 'Such polypropylene fractions. suitable forpreparingihe products of the invention, are available commercially. They are' normally produced by the superatmospheric poLvmerization of propylene 1'12 parts of 95% msoi is mixed with 42 parts of benzeneat 10 to 20 C. 65 parts of polypropylene, distilling at normal atmospheric presthe mixture is stirred for 1% hours at a temperature not above 30' C. The product is then woven cotton fabric soiled with a suspension of graphite in lubricating oil and cottonseed oil. The proportion of soil removed was determined photometrically.
- when the above detergents were mixed with tetrasodium pyrophosphate and tested at a total detergent concentration of 0.25%, employing an identical test, substantially diflerent results were allowed to stratify and the heavy H2504 layer is obtained. The following table shows the variawithdrawn. The alkylate which remains is hell-' tion of "these results with varying proportions of tralized with aqueous sodium carbonate solution; pyrophosphate.
,racliz -;1?etes'gentTBPP Ratio Dem- 1'' 00-10 ao-ao vo-ao 00-40 50-50 40-00 Pol pylons (Cu) Benzene Bodiunr 1 I 8 cute Detergent (62% No.80 i7 22 2Q 30 48 51 44 Pol pylene (Cu) Benuno Sodium 1 ..B ionataDet rs t(62%Nu80|).. .40 N 33 34 'Keryl Benzene Sodium flulionate 1 DOm (a% N28 4)----' as so as as as as an stripped with steam to. remove bnreacted benzene... After removal ofthe benzene the ,alkylate is again permittedto stratify muse water andsodium' sulfate and sodiumcarbonate are drawn The remaining, alkylate isthenj dried anhydrouscalciunrchloride and separated fromthis drying agent. i
' Toeflect sulionatiori ,oithe alkylate 50 parts of si lete is cooled to between l0'fi-and c.
an 190 parts off 20% oleum is added w llie the mixture is s i r vis mus v w t ca in to maintain the temperature below 20' C. when-all ofi'th'e oleum has been added. ag'ii'ntior is conunseat until the end of 4 hoursif'rorn the tin e of starting the addition of oleum, the temperature being maintained during this period below CI 1' The sulfonation mixture is then'int'roduced gradually into 285 parts of -aque'ous 25%- NaOH'liolution at a temperature of about -C.
The" pH of the slurry is adjusted finally to ap'-' proximately '7 by the addition of sulfuric acid and the/slurry is then dried. Drying may be eflected by means of a drum drier or a spray drier at 110 C. The dry product contains about 38% of alkyl benzene-sodium sulfonate and 62% of sodium sulfate. Upon application of the'pr'ocess oha' large scale. the content'of alkyl benzene sodium sulfonatel and sodium sulfate may vary 5%; above'or below these values.
, Arne. following tables show the results of,
launderometer' tests 'of this detergentIpmduct-incomparison with" a commercial product made from chlorinated 'kerosene and a: polypropylene benzene s'ulfonate having'an'average of-only 12 efirbonatoms 'in the polypropylene? radicals. Thesertests were made employingha'vlng a hardness corresponding -to 300 parts per million of calcium carbonate.
Table! Pol ro ylene Be an; 8111- t IBen. innate Detergent Goneentration, Percent a acne B ul flie values in thistable represent' the percentage removal than the'b'ir polypropylene benzene sulfon'ate deterde'ntjbut uponladd'itionjof tetra- W"! -PYIPPK SR 'FE. gave p0prer, and... poorer results, and'in nepase gave better results than -the 'ab ence of the i'etrssodi m ymphosphate. ereas It ac poly op ene ul m t upon addition of e r -s di m p rop bhete s better, and better results; until .at a 59-60 ratio this detergentl'was substantially. superior to any of the mixtures of keryl benzene sulf onate. as'well as to this product without the tetrasodium pyro phosphate. The product from 12 carbon atom (average) polypropylene .resembled the keryl product in its behavior and all its mixtures with 'I'SPPtested were inferior tothe 100% detergent product. l
I claim: 1
.1. A detergent composition consisting essentlally; of "polypropylene benzene sodium -.sulfonate, in .which the polypropylene radicals conv tain anaverage of between 13 and 15 carbon atoms and comprise a substantial proportion of pentapropylene" radicals, and for about. each' one part by, weight ofpolypropylenebenzene so-- dium sulfonate. (dry basis), between 1 and 3 parts. of sodium sulfate and between 5 -and,. 4-.parts.of t'etrasodiurn pyrophosphate. I
2. A detergent composition consisting. essential: ly of "polypropylene? benzene sodiumsulfonate, in which the polypropyleno radicals correspond substantially entirelyto. olefins boiling between 200 anda270 0., comprise as the major com ponent-pentapropylene radicals and contain an averageof between-13 and 15 carbon atoms; and for about each one part by weight of polypropylene benzene sodium sulfonate-(dry basis), .-be-, tweenf1.3, and 2'parts oi. sodium sulfate and between 1 and 8 partsf'of tetrasodium pyrophos pirate;
. 3. ll-detergent composition consisting'essential ly of polypropylene" --benzene sodium sulfonat'e'; in which the polypropylene" radicals correspond substantially entirely to oleilns boiling between sdnwemdveain a standard inyolving a 200' and 270 d. and predominantly between 210 "pentapropylene radicals and contain an average of between 13 and 15 carbon atoms, and for about each one part by weight of polypropylene benzene sodium sulfonate (dry basis) about 1 /10. parts of sodium sulfate, and for each part of total sulfonate and sulfate about to 1 part of tetrasodium pyrophosphate.
SAMUEL A. RUSSELL, III.
REFERENCES CITED The following references are of record in the file of this patent:
6 UNITED STATES PATENTS Number Name Date Riegler Oct. 5, 1943 Trefiier June 13, 1944 McGhie Feb. 5, 1946 Lind Mar. 12, 1946 Lewis July 26, 1949 Lewis July 26, 1949 Strain Nov. 1, 1949 OTHER REFERENCES Oil and Soap, vol. 23, 1946, page 105.
Claims (1)
1. A DETERGENT COMPOSITION CONSISTING ESSENTIALLY OF "POLYPROPYLENE" BENZENE SODIUM SULFONATE, IN WHICH THE "POLYPROPYLENE" RADICALS CONTAIN AN AVERAGE OF BETWEEN 13 AND 15 CARBON ATOMS AND COMPRISE A SUBSTANTIAL PROPORTION OF "PENTAPROPYLENE" RADICALS, AND FOR ABOUT EACH ONE PART BY WEIGTH OF POLYPROPYLENE BENZENE SODIUM SULFONATE (DRY BASIS), BETWEEN 1 AND 3 PARTS OF SODIUM SULFATE AND BETWEEN 1/3 AND 4 PARTS OF TETRASODIUM PYROPHOSPHATE.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2626900A true US2626900A (en) | 1953-01-27 |
Family
ID=3439448
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US2626900D Expired - Lifetime US2626900A (en) | Polypropylene benzene sulfonate |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2626900A (en) |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2330922A (en) * | 1941-12-22 | 1943-10-05 | Allied Chem & Dye Corp | Manufacture of sulphonated detergents |
| US2351559A (en) * | 1944-06-13 | Process for the preparation of | ||
| US2394320A (en) * | 1942-05-19 | 1946-02-05 | Colgate Palmolive Peet Co | Organic detergent compositions |
| US2396278A (en) * | 1933-11-15 | 1946-03-12 | Procter & Gamble | Detergent composition |
| US2477382A (en) * | 1946-05-04 | 1949-07-26 | California Research Corp | Aryl substituted alkanes and process of making the same |
| US2477383A (en) * | 1946-12-26 | 1949-07-26 | California Research Corp | Sulfonated detergent and its method of preparation |
| US2486922A (en) * | 1945-11-09 | 1949-11-01 | Procter & Gamble | Stabilized detergent composition |
-
0
- US US2626900D patent/US2626900A/en not_active Expired - Lifetime
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2351559A (en) * | 1944-06-13 | Process for the preparation of | ||
| US2396278A (en) * | 1933-11-15 | 1946-03-12 | Procter & Gamble | Detergent composition |
| US2330922A (en) * | 1941-12-22 | 1943-10-05 | Allied Chem & Dye Corp | Manufacture of sulphonated detergents |
| US2394320A (en) * | 1942-05-19 | 1946-02-05 | Colgate Palmolive Peet Co | Organic detergent compositions |
| US2486922A (en) * | 1945-11-09 | 1949-11-01 | Procter & Gamble | Stabilized detergent composition |
| US2477382A (en) * | 1946-05-04 | 1949-07-26 | California Research Corp | Aryl substituted alkanes and process of making the same |
| US2477383A (en) * | 1946-12-26 | 1949-07-26 | California Research Corp | Sulfonated detergent and its method of preparation |
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