US2806001A - Polyethyleneglycols as laundering aids - Google Patents
Polyethyleneglycols as laundering aids Download PDFInfo
- Publication number
- US2806001A US2806001A US324422A US32442252A US2806001A US 2806001 A US2806001 A US 2806001A US 324422 A US324422 A US 324422A US 32442252 A US32442252 A US 32442252A US 2806001 A US2806001 A US 2806001A
- Authority
- US
- United States
- Prior art keywords
- sodium
- soil
- sulphonate
- washing
- sulphate
- 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
Links
- 229920001223 polyethylene glycol Polymers 0.000 title claims description 14
- 229940068917 polyethylene glycols Drugs 0.000 title description 2
- 238000004900 laundering Methods 0.000 title 1
- 239000002689 soil Substances 0.000 claims description 22
- 239000011734 sodium Substances 0.000 claims description 13
- 229910052708 sodium Inorganic materials 0.000 claims description 13
- 239000002202 Polyethylene glycol Substances 0.000 claims description 12
- 239000000463 material Substances 0.000 claims description 12
- 239000000375 suspending agent Substances 0.000 claims description 12
- -1 SODIUM ALKYL BENZENE Chemical class 0.000 claims description 11
- 239000004753 textile Substances 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- XLYOFNOQVPJJNP-PWCQTSIFSA-N Tritiated water Chemical compound [3H]O[3H] XLYOFNOQVPJJNP-PWCQTSIFSA-N 0.000 claims 1
- 238000005406 washing Methods 0.000 description 18
- 239000003599 detergent Substances 0.000 description 17
- 239000004744 fabric Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 125000000217 alkyl group Chemical group 0.000 description 8
- 239000002609 medium Substances 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 239000006229 carbon black Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 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 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000012736 aqueous medium Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 239000000344 soap Substances 0.000 description 4
- 125000000129 anionic group Chemical group 0.000 description 3
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 2
- 239000004115 Sodium Silicate Substances 0.000 description 2
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 2
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 2
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 2
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 2
- 229910052911 sodium silicate Inorganic materials 0.000 description 2
- 235000019832 sodium triphosphate Nutrition 0.000 description 2
- 239000000271 synthetic detergent Substances 0.000 description 2
- ICPUMOMIMAIRLA-UHFFFAOYSA-N 2-methylpropyl naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)OCC(C)C)=CC=CC2=C1 ICPUMOMIMAIRLA-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- UQEAQAKWTXGXOS-UHFFFAOYSA-N C(C(C)C)C=1C(=C(C=CC1)CC(C)C)CC(C)C.[Na] Chemical compound C(C(C)C)C=1C(=C(C=CC1)CC(C)C)CC(C)C.[Na] UQEAQAKWTXGXOS-UHFFFAOYSA-N 0.000 description 1
- UUUXCBNPERIZJL-UHFFFAOYSA-N C(CCCCCCCCCCCCCCCC)OS(=O)(=O)C1=CC=CC=C1.[Na] Chemical compound C(CCCCCCCCCCCCCCCC)OS(=O)(=O)C1=CC=CC=C1.[Na] UUUXCBNPERIZJL-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- JLVVSXFLKOJNIY-UHFFFAOYSA-N Magnesium ion Chemical compound [Mg+2] JLVVSXFLKOJNIY-UHFFFAOYSA-N 0.000 description 1
- LMIJIHJZVURGQK-UHFFFAOYSA-N N-stearoyltaurine Chemical compound CCCCCCCCCCCCCCCCCC(=O)NCCS(O)(=O)=O LMIJIHJZVURGQK-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000004141 Sodium laurylsulphate Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical compound OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 1
- 230000001464 adherent effect Effects 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- 229910021538 borax Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910001424 calcium ion Inorganic materials 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- VQZHOOBGYXKMLU-UHFFFAOYSA-N decyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 VQZHOOBGYXKMLU-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000008233 hard water Substances 0.000 description 1
- QKIAYRRGJHLRAQ-UHFFFAOYSA-N hexadecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 QKIAYRRGJHLRAQ-UHFFFAOYSA-N 0.000 description 1
- 150000002646 long chain fatty acid esters Chemical class 0.000 description 1
- 229910001425 magnesium ion Inorganic materials 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- KIHUPOKUSVEICJ-UHFFFAOYSA-N nonyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 KIHUPOKUSVEICJ-UHFFFAOYSA-N 0.000 description 1
- MXXDSLLVYZMTFA-UHFFFAOYSA-N octadecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 MXXDSLLVYZMTFA-UHFFFAOYSA-N 0.000 description 1
- YSVFUNHOUJFANW-UHFFFAOYSA-N octyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCOS(=O)(=O)C1=CC=CC=C1 YSVFUNHOUJFANW-UHFFFAOYSA-N 0.000 description 1
- 235000014593 oils and fats Nutrition 0.000 description 1
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- CAOVKIWLIMUXEU-UHFFFAOYSA-N pentadecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 CAOVKIWLIMUXEU-UHFFFAOYSA-N 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- FQENQNTWSFEDLI-UHFFFAOYSA-J sodium diphosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])([O-])=O FQENQNTWSFEDLI-UHFFFAOYSA-J 0.000 description 1
- GCLGEJMYGQKIIW-UHFFFAOYSA-H sodium hexametaphosphate Chemical compound [Na]OP1(=O)OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])O1 GCLGEJMYGQKIIW-UHFFFAOYSA-H 0.000 description 1
- 235000019982 sodium hexametaphosphate Nutrition 0.000 description 1
- 235000019795 sodium metasilicate Nutrition 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 235000019794 sodium silicate Nutrition 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- FVEFRICMTUKAML-UHFFFAOYSA-M sodium tetradecyl sulfate Chemical compound [Na+].CCCCC(CC)CCC(CC(C)C)OS([O-])(=O)=O FVEFRICMTUKAML-UHFFFAOYSA-M 0.000 description 1
- ZKBBQUFQDGOTBZ-UHFFFAOYSA-N sodium;1,2,3-tri(propan-2-yl)naphthalene Chemical compound [Na].C1=CC=C2C(C(C)C)=C(C(C)C)C(C(C)C)=CC2=C1 ZKBBQUFQDGOTBZ-UHFFFAOYSA-N 0.000 description 1
- HFQQZARZPUDIFP-UHFFFAOYSA-M sodium;2-dodecylbenzenesulfonate Chemical compound [Na+].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O HFQQZARZPUDIFP-UHFFFAOYSA-M 0.000 description 1
- GWCMKOHVMSHWKI-UHFFFAOYSA-M sodium;4-tetradecylbenzenesulfonate Chemical compound [Na+].CCCCCCCCCCCCCCC1=CC=C(S([O-])(=O)=O)C=C1 GWCMKOHVMSHWKI-UHFFFAOYSA-M 0.000 description 1
- DUXXGJTXFHUORE-UHFFFAOYSA-M sodium;4-tridecylbenzenesulfonate Chemical compound [Na+].CCCCCCCCCCCCCC1=CC=C(S([O-])(=O)=O)C=C1 DUXXGJTXFHUORE-UHFFFAOYSA-M 0.000 description 1
- MWZFQMUXPSUDJQ-KVVVOXFISA-M sodium;[(z)-octadec-9-enyl] sulfate Chemical compound [Na+].CCCCCCCC\C=C/CCCCCCCCOS([O-])(=O)=O MWZFQMUXPSUDJQ-KVVVOXFISA-M 0.000 description 1
- AIMUHNZKNFEZSN-UHFFFAOYSA-M sodium;decane-1-sulfonate Chemical compound [Na+].CCCCCCCCCCS([O-])(=O)=O AIMUHNZKNFEZSN-UHFFFAOYSA-M 0.000 description 1
- XZTJQQLJJCXOLP-UHFFFAOYSA-M sodium;decyl sulfate Chemical compound [Na+].CCCCCCCCCCOS([O-])(=O)=O XZTJQQLJJCXOLP-UHFFFAOYSA-M 0.000 description 1
- DAJSVUQLFFJUSX-UHFFFAOYSA-M sodium;dodecane-1-sulfonate Chemical compound [Na+].CCCCCCCCCCCCS([O-])(=O)=O DAJSVUQLFFJUSX-UHFFFAOYSA-M 0.000 description 1
- HHURSJAUVYNJBT-UHFFFAOYSA-M sodium;heptadecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCCCCOS([O-])(=O)=O HHURSJAUVYNJBT-UHFFFAOYSA-M 0.000 description 1
- PNGBYKXZVCIZRN-UHFFFAOYSA-M sodium;hexadecane-1-sulfonate Chemical compound [Na+].CCCCCCCCCCCCCCCCS([O-])(=O)=O PNGBYKXZVCIZRN-UHFFFAOYSA-M 0.000 description 1
- GGHPAKFFUZUEKL-UHFFFAOYSA-M sodium;hexadecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCCCOS([O-])(=O)=O GGHPAKFFUZUEKL-UHFFFAOYSA-M 0.000 description 1
- RUYRDULZOKULPK-UHFFFAOYSA-M sodium;nonane-1-sulfonate Chemical compound [Na+].CCCCCCCCCS([O-])(=O)=O RUYRDULZOKULPK-UHFFFAOYSA-M 0.000 description 1
- FTWCSAMTIKSPAT-UHFFFAOYSA-M sodium;nonyl sulfate Chemical compound [Na+].CCCCCCCCCOS([O-])(=O)=O FTWCSAMTIKSPAT-UHFFFAOYSA-M 0.000 description 1
- KBAFDSIZQYCDPK-UHFFFAOYSA-M sodium;octadecane-1-sulfonate Chemical compound [Na+].CCCCCCCCCCCCCCCCCCS([O-])(=O)=O KBAFDSIZQYCDPK-UHFFFAOYSA-M 0.000 description 1
- NWZBFJYXRGSRGD-UHFFFAOYSA-M sodium;octadecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCCCCCOS([O-])(=O)=O NWZBFJYXRGSRGD-UHFFFAOYSA-M 0.000 description 1
- HRQDCDQDOPSGBR-UHFFFAOYSA-M sodium;octane-1-sulfonate Chemical compound [Na+].CCCCCCCCS([O-])(=O)=O HRQDCDQDOPSGBR-UHFFFAOYSA-M 0.000 description 1
- WFRKJMRGXGWHBM-UHFFFAOYSA-M sodium;octyl sulfate Chemical compound [Na+].CCCCCCCCOS([O-])(=O)=O WFRKJMRGXGWHBM-UHFFFAOYSA-M 0.000 description 1
- PLQISZLZPSPBDP-UHFFFAOYSA-M sodium;pentadecane-1-sulfonate Chemical compound [Na+].CCCCCCCCCCCCCCCS([O-])(=O)=O PLQISZLZPSPBDP-UHFFFAOYSA-M 0.000 description 1
- SMECTXYFLVLAJE-UHFFFAOYSA-M sodium;pentadecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCCOS([O-])(=O)=O SMECTXYFLVLAJE-UHFFFAOYSA-M 0.000 description 1
- AYFACLKQYVTXNS-UHFFFAOYSA-M sodium;tetradecane-1-sulfonate Chemical compound [Na+].CCCCCCCCCCCCCCS([O-])(=O)=O AYFACLKQYVTXNS-UHFFFAOYSA-M 0.000 description 1
- CACJZDMMUHMEBN-UHFFFAOYSA-M sodium;tridecane-1-sulfonate Chemical compound [Na+].CCCCCCCCCCCCCS([O-])(=O)=O CACJZDMMUHMEBN-UHFFFAOYSA-M 0.000 description 1
- HQCFDOOSGDZRII-UHFFFAOYSA-M sodium;tridecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCOS([O-])(=O)=O HQCFDOOSGDZRII-UHFFFAOYSA-M 0.000 description 1
- DBMQUCVJHLWQHT-UHFFFAOYSA-M sodium;undecane-1-sulfonate Chemical compound [Na+].CCCCCCCCCCCS([O-])(=O)=O DBMQUCVJHLWQHT-UHFFFAOYSA-M 0.000 description 1
- NZRSEGYTVSNMCK-UHFFFAOYSA-N sodium;undecyl benzenesulfonate Chemical compound [Na].CCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 NZRSEGYTVSNMCK-UHFFFAOYSA-N 0.000 description 1
- UOWRKHDWHDWJHK-UHFFFAOYSA-M sodium;undecyl sulfate Chemical compound [Na+].CCCCCCCCCCCOS([O-])(=O)=O UOWRKHDWHDWJHK-UHFFFAOYSA-M 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 235000019818 tetrasodium diphosphate Nutrition 0.000 description 1
- 239000001577 tetrasodium phosphonato phosphate Substances 0.000 description 1
- 150000003568 thioethers Chemical class 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
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/0005—Other compounding ingredients characterised by their effect
- C11D3/0036—Soil deposition preventing compositions; Antiredeposition agents
Definitions
- This invention relates to washing procedures particularly to the washing of textile materials such as fabrics and fibers with aqueous media.
- the invention concerns the use of polyethyleneglycol in the aqueous washing medium whereby to minimize the re-deposition of soil during the washing procedure.
- a successful Washing operation involves two separate factors, i. e., (a) the removal of dirt from the textile material and (b) keeping the soil suspended in the medium so that it will not be re-deposited on the textile.
- aqueous Washing media containing soap fulfill both of these criteria as soap not only is a good soil remover but also keeps the removed soil in suspension so that little re-deposition takes place.
- anionic synthetic detergents such as the alkyl benzene sulphonates since these agents can be used in hard water areas as their detersive power is not decreased by the presence of calcium and magnesium ions.
- these anionic detergents have the disadvantage that their suspending power is poor.
- polyethyleneglycol has useful soil-suspending properties and when added to aqueous washing media the degree of soil re-deposition is greatly reduced.
- polyethyleneglycol is not a single, individual compound but may be obtained in almost any degree of polymerization.
- the degree of polymerization is most easily expressed in terms of average molecular weight.
- this invention comprises in its broad aspect the use of polyethyleneglycol having any degree of polymerization and which is soluble in water at least to the extent of about .001% to about 0.1%, it is to be understood that not all the polymers possess the same degree of effectiveness.
- polyethyleneglycols having an average molecular weight from about 1,000 to about 10,000 exhibit maximum soil-suspending activity. For this reason it is preferred to use a polyethyleneglycol of such molecular weight range as a soil-suspending agent in washing operations.
- the polyethyeneglycol may be dispersed into the aqueous washing medium in a concentration from about 0.001% to about 0.1%, the higher proportions giving the greater degree of protection against soil redeposition. It is obvious that the proportion of polyethyleneglycol can be higher than the above ice ' range but in' general increasing the concentration above 0.1% gives little if any added protection.
- the polyethyleneglycol can be incorporated with the detergent so as to form a composition which on dissolving in water furnishes the desired washing medium. To this end, the detergent is mixed with about 2 to 10% of the aforesaid soil-suspending agent.
- the fabric or other textile material is agitated in the usual'manner preferably at elevated temperatures as commonly used in laundries with the aqueous media containing the polyethyleneglycol and the detergent.
- the detergent one may use any of the materials commonly used for washing purposes.
- the detergent may be, for example, of the anionic'or non-ionic types.
- ordinary soaps that is, sodium or potassium salts of the higher fatty acids, or usually, mixtures of higher fatty acids as are present in naturally occurring oils and fats.
- anionic category the detergents of the sulphonate or sulphate type.
- alkyl (C8Cl8) sulphates As well known in the art, a multitude of such materials are available, including the alkyl (C8Cl8) sulphates, the alkyl (Cs-C13) sulphonates, the alkyl (Cs-C18) aromatic sulphonates, the monoor di-alkyl (Cs-C13) esters of sulphosuccinic acid, sulphonated or sulphated amides of the higher fatty acids such as N-sulphoethyl stearamide, and so fourth.
- These compounds are generally employed in the form of their salts, i. e., their sodium, potassium, ammonium or amine salts.
- Some of the particular detergents which may be used are: sodium octyl sulphate, sodium nonyl sulphate, sodium decyl sulphate, sodium undecyl sulphate, sodium dodecyl sulphate, sodium tridecyl sulphate, sodium tetradecyl sulphate, sodium pentadecyl sulphate, sodium hexadecyl sulphate, sodium heptadecyl sulphate, sodium octadecyl sulphate, sodium oleyl sulphate, sodium octyl sulphonate, sodium nonyl sulphonate, sodium decyl sulphonate, sodium undecyl sulphonate, sodium dodecyl sulphonate, sodium tridecyl sulphonate, sodium tetradecyl sulphonate, sodium pentadecyl sulphonate, sodium he
- the sodium alkyl benzene sulphonate wherein the alkyl group contains 12 to 18 carbon atoms is a Well known detergent. Others are: a mixture of sodium alkyl sulphates consisting mostly of sodium lauryl sulphate; a mixture of sodium alkyl phenol sulphonates wherein the alkyl group contains 12 to 18 carbon atoms; and a mixture of sodium alkyl sulphonates wherein the alkyl group contains 10 to 18 carbon atoms.
- non-anionic detergents one may employ polyalkylene glycol esters, ethers and thioethers of the following types:
- R represent long chain alkyl radicals of 8 to 12 carbon atoms and n is an integer from about 4 to 12.
- Other non-anionic detergents are the long-chain fatty acid esters of anhydrosorbitol, or the polyethylene glycol addition products of such esters. It is evident that the particular detergent used is not critical except that one should be chosen which is generally useful in emulsitying and detergent applications.
- the concentration of the detergent is not critical within a wide range and depending on the soil removal etficiency of the particular agent, the range of concentration may be from about 0.05% to about 0.5%. If desired, the soil removal efilciency of the detergent maybe increased by addition to the aqueous medium of any of the usual types of builders such as sodium hexametaphosphate, tetrasodium pyrophosphate, sodium tripolyphosphate, trisodium phosphate, borax, sodium carbonate, sodium silicate, sodium metasilicate, and so forth.
- Example I A series of experiments were carried out in which clean swatches of cloth were agitated in an aqueous media containing a synthetic detergent, various soil-suspending agents at various'concentration levels, and carbon black. The treated swatches were then subjected to reflectance measurements to measure the amount of soil (carbon black) which had been deposited on the fabric thus to compare the effectiveness of the soil-suspending agents. The reflectance values are an index of the cleanness of the cloth; the higher the proportion of light reflected the cleaner the. cloth. The experiments were carried out as follows:
- a standard washing medium was prepared containing: water; sodium alkyl (C12C18) benzene sulphonate, 0.12%; sodium tripolyphosphate, 0.08%; sodium carbonate, 0.04%; and carbon black, 0.1%.
- the pH of this solution was about 10.3.
- To samples of the standard medium were added various soil-suspending agents as hereinafter indicated. Each solution so prepared was tested as follows:
- test solution Two hundred cc. of the test solution was placed in a pint jar together with a swatch of a standard bleached muslin (cotton) cloth and 20%" stainless-steel balls.
- the jar was then sealed and placed in a Launderometer and agitated by rotation at 140 F. for 20 minutes.
- the test swatch was then removed, rinsed 4 times with distilled water and agitated with 200 cc. of distilled water in the Launderometer for 10 minutes at 140 F. This washing in distilled water was done to remove loosely adherent carbon black so that the results would relate solely to adsorbed soil.
- the treated swatch was then dried in air, ironed, and the reflectance measured.
- a process for removing soil from a textile material and minimizing the re-deposition of removed soil which comprises washing the material with a solution comprising water, about 0.05% to about 0.5% of a sodium alkyl benzene sulphonate wherein the alkyl group contains 12 to 18 carbon atoms, and a soil suspending agent consisting of about 0.001% to about 0.1% concentration in said solution of a polyethyleneglycol having an average molecular weight of 6,000 to 7,500.
- a washing solution which is effective to remove soil from textile materials and to minimize re-deposition of removed soil which comprises water, about 0.05 to about 0.5% of sodium alkyl benzene sulphonate wherein the alkyl group contains 12 to 18 carbon atoms, and a soil suspending agent consisting of about 0.001% to about 0.1% concentration in said solution of a polyethyleneglycol having an average molecular weight of 6,000 to 7,500.
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- Chemical & Material Sciences (AREA)
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Description
United States Patent() assiguors to the United States of America the Secretary of Agriculture Willie Fong,
ley, Califi, as represented by No rawing. Application December 5, 1952, Serial No. 324,422
2 Claims. (Cl. 252-461) (Granted under Title 35, U. S. Code (1952), see. 266) A non-exclusive, irrevocable, royalty-free license in the invention herein described, for all governmental purposes, throughout the world, with the power to grant sublicenses for such purposes, is hereby granted to the Government of the United States of America.
This invention relates to washing procedures particularly to the washing of textile materials such as fabrics and fibers with aqueous media. In particular the invention concerns the use of polyethyleneglycol in the aqueous washing medium whereby to minimize the re-deposition of soil during the washing procedure.
It is well known in the art that a successful Washing operation involves two separate factors, i. e., (a) the removal of dirt from the textile material and (b) keeping the soil suspended in the medium so that it will not be re-deposited on the textile. In general aqueous Washing media containing soap fulfill both of these criteria as soap not only is a good soil remover but also keeps the removed soil in suspension so that little re-deposition takes place. However, the present trend is toward the use of anionic synthetic detergents such as the alkyl benzene sulphonates since these agents can be used in hard water areas as their detersive power is not decreased by the presence of calcium and magnesium ions. However, these anionic detergents have the disadvantage that their suspending power is poor. Whereas they are very effective from the standpoint of removing soil they are not so efiective in preventing re-deposition and so cotton fabrics washed with such agents will be grayer than when using soap. In order to overcome this disadvantage, various soil suspending agents are commonly added to the anionic detergents. One of the most commonly used agents is sodium carboxymethyl cellulose.
It has now been found that polyethyleneglycol has useful soil-suspending properties and when added to aqueous washing media the degree of soil re-deposition is greatly reduced. As Well known in the art, polyethyleneglycol is not a single, individual compound but may be obtained in almost any degree of polymerization. The degree of polymerization is most easily expressed in terms of average molecular weight. Although this invention comprises in its broad aspect the use of polyethyleneglycol having any degree of polymerization and which is soluble in water at least to the extent of about .001% to about 0.1%, it is to be understood that not all the polymers possess the same degree of effectiveness. Thus polyethyleneglycols having an average molecular weight from about 1,000 to about 10,000 exhibit maximum soil-suspending activity. For this reason it is preferred to use a polyethyleneglycol of such molecular weight range as a soil-suspending agent in washing operations.
In applying this invention in practice the polyethyeneglycol may be dispersed into the aqueous washing medium in a concentration from about 0.001% to about 0.1%, the higher proportions giving the greater degree of protection against soil redeposition. It is obvious that the proportion of polyethyleneglycol can be higher than the above ice ' range but in' general increasing the concentration above 0.1% gives little if any added protection. If desired, the polyethyleneglycol can be incorporated with the detergent so as to form a composition which on dissolving in water furnishes the desired washing medium. To this end, the detergent is mixed with about 2 to 10% of the aforesaid soil-suspending agent.
In carrying out washing operations in accordance with this invention, the fabric or other textile material is agitated in the usual'manner preferably at elevated temperatures as commonly used in laundries with the aqueous media containing the polyethyleneglycol and the detergent. As the detergent one may use any of the materials commonly used for washing purposes.
The detergent may be, for example, of the anionic'or non-ionic types. In the first category are included ordinary soaps, that is, sodium or potassium salts of the higher fatty acids, or usually, mixtures of higher fatty acids as are present in naturally occurring oils and fats. Also included in the anionic category are the detergents of the sulphonate or sulphate type. As well known in the art, a multitude of such materials are available, including the alkyl (C8Cl8) sulphates, the alkyl (Cs-C13) sulphonates, the alkyl (Cs-C18) aromatic sulphonates, the monoor di-alkyl (Cs-C13) esters of sulphosuccinic acid, sulphonated or sulphated amides of the higher fatty acids such as N-sulphoethyl stearamide, and so fourth. These compounds are generally employed in the form of their salts, i. e., their sodium, potassium, ammonium or amine salts. Some of the particular detergents which may be used are: sodium octyl sulphate, sodium nonyl sulphate, sodium decyl sulphate, sodium undecyl sulphate, sodium dodecyl sulphate, sodium tridecyl sulphate, sodium tetradecyl sulphate, sodium pentadecyl sulphate, sodium hexadecyl sulphate, sodium heptadecyl sulphate, sodium octadecyl sulphate, sodium oleyl sulphate, sodium octyl sulphonate, sodium nonyl sulphonate, sodium decyl sulphonate, sodium undecyl sulphonate, sodium dodecyl sulphonate, sodium tridecyl sulphonate, sodium tetradecyl sulphonate, sodium pentadecyl sulphonate, sodium hexadecyl sulphonate, sodium octadecyl sulphonate, sodium oleyl sulphonate, sodium salt of dioctyl sulpho succinate, sodium octyl benzene sulphonate, sodium nonyl benzene sulphonate, sodium decyl benzene sulphonate, sodium undecyl benzene sulphonate, sodium dodecyl benzene sulphonate, sodium tridecyl benzene sulphonate, sodium tetradecyl benzene sulphonate, sodium pentadecyl benzene sulphonate, sodium hexadecyl benzene sulphonate, sodium heptadecyl benzene sulphonate, sodium octadecyl benzene sulphonate, sodium tri (isopropyl) benzene sulphonate, sodium tri (isobutyl) benzene sulphonate, sodium tri (isopropyl) naphthalene sulphonate, sodium tn' (isobutyl) naphthalene sulphonate, and so forth. The commercially available detergents are generally not pure compounds but are mixtures of homologous compounds and are quite satisfactory. Thus for example, the sodium alkyl benzene sulphonate wherein the alkyl group contains 12 to 18 carbon atoms is a Well known detergent. Others are: a mixture of sodium alkyl sulphates consisting mostly of sodium lauryl sulphate; a mixture of sodium alkyl phenol sulphonates wherein the alkyl group contains 12 to 18 carbon atoms; and a mixture of sodium alkyl sulphonates wherein the alkyl group contains 10 to 18 carbon atoms. As non-anionic detergents one may employ polyalkylene glycol esters, ethers and thioethers of the following types:
wherein the Rs represent long chain alkyl radicals of 8 to 12 carbon atoms and n is an integer from about 4 to 12. Other non-anionic detergents are the long-chain fatty acid esters of anhydrosorbitol, or the polyethylene glycol addition products of such esters. It is evident that the particular detergent used is not critical except that one should be chosen which is generally useful in emulsitying and detergent applications.
The concentration of the detergent is not critical within a wide range and depending on the soil removal etficiency of the particular agent, the range of concentration may be from about 0.05% to about 0.5%. If desired, the soil removal efilciency of the detergent maybe increased by addition to the aqueous medium of any of the usual types of builders such as sodium hexametaphosphate, tetrasodium pyrophosphate, sodium tripolyphosphate, trisodium phosphate, borax, sodium carbonate, sodium silicate, sodium metasilicate, and so forth.
The following examples illustrate the invention in greater detail. The known soil-suspending agent, sodium carboxymethyl cellulose, was employed in some of the experiments for comparative purposes. In all the experiments, carbon black was added to the washing media to test the soil-suspending power of the various materials under test. Obviously in practice of the invention, no carbon black or other soil would be added to the washing medium.
' Example I A series of experiments were carried out in which clean swatches of cloth were agitated in an aqueous media containing a synthetic detergent, various soil-suspending agents at various'concentration levels, and carbon black. The treated swatches were then subjected to reflectance measurements to measure the amount of soil (carbon black) which had been deposited on the fabric thus to compare the effectiveness of the soil-suspending agents. The reflectance values are an index of the cleanness of the cloth; the higher the proportion of light reflected the cleaner the. cloth. The experiments were carried out as follows:
A standard washing medium was prepared containing: water; sodium alkyl (C12C18) benzene sulphonate, 0.12%; sodium tripolyphosphate, 0.08%; sodium carbonate, 0.04%; and carbon black, 0.1%. The pH of this solution was about 10.3. To samples of the standard medium were added various soil-suspending agents as hereinafter indicated. Each solution so prepared was tested as follows:
Two hundred cc. of the test solution was placed in a pint jar together with a swatch of a standard bleached muslin (cotton) cloth and 20%" stainless-steel balls.
The jar was then sealed and placed in a Launderometer and agitated by rotation at 140 F. for 20 minutes. The test swatch was then removed, rinsed 4 times with distilled water and agitated with 200 cc. of distilled water in the Launderometer for 10 minutes at 140 F. This washing in distilled water was done to remove loosely adherent carbon black so that the results would relate solely to adsorbed soil. The treated swatch was then dried in air, ironed, and the reflectance measured.
The materials and proportions used and the results obtained are tabulated below:
Reflectance (percent) of washed samples using various soil-suspending agents at various concentration levels Concentration of soil-suspending agent, Polyethylene Polyethylene- Polyethylene- Sodium percent glycol, glycol, glycol, carboxy- Average mol. average 1110]. average mol. methyl Wt. 6,000- wt. 1,300- wt. 380-420 cellulose The reflectance of the original cloth sample was Having thus described our invention We claim:
1. A process for removing soil from a textile material and minimizing the re-deposition of removed soil which comprises washing the material with a solution comprising water, about 0.05% to about 0.5% of a sodium alkyl benzene sulphonate wherein the alkyl group contains 12 to 18 carbon atoms, and a soil suspending agent consisting of about 0.001% to about 0.1% concentration in said solution of a polyethyleneglycol having an average molecular weight of 6,000 to 7,500.
2. A washing solution which is effective to remove soil from textile materials and to minimize re-deposition of removed soil which comprises water, about 0.05 to about 0.5% of sodium alkyl benzene sulphonate wherein the alkyl group contains 12 to 18 carbon atoms, and a soil suspending agent consisting of about 0.001% to about 0.1% concentration in said solution of a polyethyleneglycol having an average molecular weight of 6,000 to 7,500.
References Cited in the file of this patent UNITED STATES PATENTS bide and Carbon Chem. Corp., N. Y. (1946), page 9.
Synthetic Organic Chemicals, Carbide and Carbon Chem. Corp., N. Y., 12th ed. (1945), pages l923.
Claims (1)
1. A PROCESS FOR REMOVING SOIL FROM A TEXTILE MATERIAL AND MINIMIZING THE RE-DEPOSITION OF REMOVED SOIL WHICH COMPRISES WASHING THE MATERIAL WITH A SOLUTION COMPRISING WATER, ABOUT 0.05% TO ABOUT 0.5% OF A SODIUM ALKYL BENZENE SULPHONATE WHEREIN THE ALKYL GROUP CONTAINS 12 TO 18 CARBON ATOMS, AND A SOIL SUSPENDING AGENT CONSISTING OF ABOUT 0.001% TO ABOUT 0.1% CONCENTRATION IN SAID SOLUTION OF A POLYETHYLENEGLYCOL HAVING AN AVERAGE MOLECULAR WEIGHT OF 6,000 TO 7,500.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US324422A US2806001A (en) | 1952-12-05 | 1952-12-05 | Polyethyleneglycols as laundering aids |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US324422A US2806001A (en) | 1952-12-05 | 1952-12-05 | Polyethyleneglycols as laundering aids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2806001A true US2806001A (en) | 1957-09-10 |
Family
ID=23263511
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US324422A Expired - Lifetime US2806001A (en) | 1952-12-05 | 1952-12-05 | Polyethyleneglycols as laundering aids |
Country Status (1)
| Country | Link |
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| US (1) | US2806001A (en) |
Cited By (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3034989A (en) * | 1957-11-22 | 1962-05-15 | Stamford Chemical Ind Inc | Detergent composition |
| US3067144A (en) * | 1959-11-16 | 1962-12-04 | Stamford Chemical Ind Inc | Detergent composition |
| US3069360A (en) * | 1958-09-11 | 1962-12-18 | Mankowich Abraham | Detergent compositions for removing silicone grease |
| US3525688A (en) * | 1967-05-08 | 1970-08-25 | Phillips Petroleum Co | Drilling fluids |
| US3619119A (en) * | 1967-12-28 | 1971-11-09 | Henkel & Cie Gmbh | Pasty spot-treating compositions for use on textiles |
| US3698479A (en) * | 1969-08-08 | 1972-10-17 | Amoco Prod Co | Solubilized oil-water solutions suitable for miscible flooding |
| US3896040A (en) * | 1971-01-04 | 1975-07-22 | Andre Danesh | Detergent composition |
| US3933672A (en) * | 1972-08-01 | 1976-01-20 | The Procter & Gamble Company | Controlled sudsing detergent compositions |
| US3960780A (en) * | 1974-10-31 | 1976-06-01 | Kao Soap Co., Ltd. | Non-caking alkyl ether sulfate-containing detergent composition |
| US4000080A (en) * | 1974-10-11 | 1976-12-28 | The Procter & Gamble Company | Low phosphate content detergent composition |
| US4096081A (en) * | 1976-02-06 | 1978-06-20 | The Procter & Gamble Company | Detergent compositions containing aluminosilicate agglomerates |
| US4118344A (en) * | 1976-05-21 | 1978-10-03 | The Dow Chemical Company | Drycleaning detergent solution |
| US4276205A (en) * | 1980-02-04 | 1981-06-30 | The Procter & Gamble Company | Detergent compositions containing amine oxide and nonionic surfactants and polyethylene glycol |
| US4316811A (en) * | 1980-07-10 | 1982-02-23 | Internorth, Inc | Dust suppressant |
| EP0050894A1 (en) * | 1980-10-29 | 1982-05-05 | THE PROCTER & GAMBLE COMPANY | Water-softening compositions on basis of aluminosilicates and detergent compositions containing them |
| US4490271A (en) * | 1983-06-30 | 1984-12-25 | The Procter & Gamble Company | Detergent compositions containing polyethylene glycol and polyacrylate |
| FR2564852A1 (en) * | 1984-05-23 | 1985-11-29 | Rhone Poulenc Chim Base | Detergent compositions comprising ethylene oxide/alkylene oxide polymers as antiredepositing agents |
| EP0165136A1 (en) * | 1984-05-23 | 1985-12-18 | Rhone-Poulenc Chimie | Detergent compositions containing copolymers based on polyoxyethylene and polyoxyalkylene used as antisoil redeposition agents, and process for their preparation |
| US4612137A (en) * | 1984-09-03 | 1986-09-16 | Kao Corporation | Anti-yellowing detergent composition containing citrate and isocitrate |
| US5523017A (en) * | 1991-10-07 | 1996-06-04 | Nephin | Solid cleansing bar |
| US5749924A (en) * | 1995-06-27 | 1998-05-12 | The Proctor & Gamble Company | Cleaning/sanitizing methods, compositions, and/or articles for fabric |
| US5759982A (en) * | 1994-06-17 | 1998-06-02 | The Procter & Gamble Company | Laundry bars with polyethylene glycol as a processing aid |
| WO2018114451A1 (en) * | 2016-12-23 | 2018-06-28 | Henkel Ag & Co. Kgaa | Redeposition inhibition when washing laundry |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2329694A (en) * | 1940-08-03 | 1943-09-21 | Lever Brothers Ltd | Dedusting process and the product thereof |
| US2566501A (en) * | 1948-01-30 | 1951-09-04 | Wyandotte Chemicals Corp | Alkyl aryl sulfonate-carboxy-methylcellulose-alkaline salt detergent composition |
-
1952
- 1952-12-05 US US324422A patent/US2806001A/en not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2329694A (en) * | 1940-08-03 | 1943-09-21 | Lever Brothers Ltd | Dedusting process and the product thereof |
| US2566501A (en) * | 1948-01-30 | 1951-09-04 | Wyandotte Chemicals Corp | Alkyl aryl sulfonate-carboxy-methylcellulose-alkaline salt detergent composition |
Cited By (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3034989A (en) * | 1957-11-22 | 1962-05-15 | Stamford Chemical Ind Inc | Detergent composition |
| US3069360A (en) * | 1958-09-11 | 1962-12-18 | Mankowich Abraham | Detergent compositions for removing silicone grease |
| US3067144A (en) * | 1959-11-16 | 1962-12-04 | Stamford Chemical Ind Inc | Detergent composition |
| US3525688A (en) * | 1967-05-08 | 1970-08-25 | Phillips Petroleum Co | Drilling fluids |
| US3619119A (en) * | 1967-12-28 | 1971-11-09 | Henkel & Cie Gmbh | Pasty spot-treating compositions for use on textiles |
| US3698479A (en) * | 1969-08-08 | 1972-10-17 | Amoco Prod Co | Solubilized oil-water solutions suitable for miscible flooding |
| US3896040A (en) * | 1971-01-04 | 1975-07-22 | Andre Danesh | Detergent composition |
| US3933672A (en) * | 1972-08-01 | 1976-01-20 | The Procter & Gamble Company | Controlled sudsing detergent compositions |
| US4000080A (en) * | 1974-10-11 | 1976-12-28 | The Procter & Gamble Company | Low phosphate content detergent composition |
| US3960780A (en) * | 1974-10-31 | 1976-06-01 | Kao Soap Co., Ltd. | Non-caking alkyl ether sulfate-containing detergent composition |
| US4096081A (en) * | 1976-02-06 | 1978-06-20 | The Procter & Gamble Company | Detergent compositions containing aluminosilicate agglomerates |
| US4118344A (en) * | 1976-05-21 | 1978-10-03 | The Dow Chemical Company | Drycleaning detergent solution |
| US4276205A (en) * | 1980-02-04 | 1981-06-30 | The Procter & Gamble Company | Detergent compositions containing amine oxide and nonionic surfactants and polyethylene glycol |
| US4316811A (en) * | 1980-07-10 | 1982-02-23 | Internorth, Inc | Dust suppressant |
| EP0050894A1 (en) * | 1980-10-29 | 1982-05-05 | THE PROCTER & GAMBLE COMPANY | Water-softening compositions on basis of aluminosilicates and detergent compositions containing them |
| US4490271A (en) * | 1983-06-30 | 1984-12-25 | The Procter & Gamble Company | Detergent compositions containing polyethylene glycol and polyacrylate |
| FR2564852A1 (en) * | 1984-05-23 | 1985-11-29 | Rhone Poulenc Chim Base | Detergent compositions comprising ethylene oxide/alkylene oxide polymers as antiredepositing agents |
| EP0165136A1 (en) * | 1984-05-23 | 1985-12-18 | Rhone-Poulenc Chimie | Detergent compositions containing copolymers based on polyoxyethylene and polyoxyalkylene used as antisoil redeposition agents, and process for their preparation |
| US4612137A (en) * | 1984-09-03 | 1986-09-16 | Kao Corporation | Anti-yellowing detergent composition containing citrate and isocitrate |
| US5523017A (en) * | 1991-10-07 | 1996-06-04 | Nephin | Solid cleansing bar |
| US5759982A (en) * | 1994-06-17 | 1998-06-02 | The Procter & Gamble Company | Laundry bars with polyethylene glycol as a processing aid |
| US5749924A (en) * | 1995-06-27 | 1998-05-12 | The Proctor & Gamble Company | Cleaning/sanitizing methods, compositions, and/or articles for fabric |
| US5914302A (en) * | 1995-06-27 | 1999-06-22 | The Procter & Gamble Company | Cleaning/sanitizing methods, compositions, and/or articles |
| WO2018114451A1 (en) * | 2016-12-23 | 2018-06-28 | Henkel Ag & Co. Kgaa | Redeposition inhibition when washing laundry |
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