US3644204A - Agent for the post-treatment of washed laundry - Google Patents
Agent for the post-treatment of washed laundry Download PDFInfo
- Publication number
- US3644204A US3644204A US743610A US3644204DA US3644204A US 3644204 A US3644204 A US 3644204A US 743610 A US743610 A US 743610A US 3644204D A US3644204D A US 3644204DA US 3644204 A US3644204 A US 3644204A
- Authority
- US
- United States
- Prior art keywords
- carbon atoms
- water
- agents
- alkyl
- acid
- 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
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 55
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 28
- 239000000203 mixture Substances 0.000 claims abstract description 27
- 150000001875 compounds Chemical class 0.000 claims abstract description 26
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 20
- 239000004599 antimicrobial Substances 0.000 claims abstract description 20
- 239000007787 solid Substances 0.000 claims abstract description 19
- -1 ether alcohols Chemical class 0.000 claims description 48
- 239000000126 substance Substances 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 15
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 14
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
- 239000003960 organic solvent Substances 0.000 claims description 10
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 229920001223 polyethylene glycol Polymers 0.000 claims description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 6
- 239000004744 fabric Substances 0.000 claims description 6
- 239000004202 carbamide Substances 0.000 claims description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 4
- 150000001298 alcohols Chemical class 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 238000004900 laundering Methods 0.000 claims description 3
- 235000011007 phosphoric acid Nutrition 0.000 claims description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims description 2
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 235000011187 glycerol Nutrition 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 150000003016 phosphoric acids Chemical class 0.000 claims description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 abstract description 31
- 239000004902 Softening Agent Substances 0.000 abstract description 28
- 239000007788 liquid Substances 0.000 abstract description 13
- 230000003287 optical effect Effects 0.000 abstract description 9
- 239000003086 colorant Substances 0.000 abstract description 4
- 239000002304 perfume Substances 0.000 abstract description 4
- 239000004753 textile Substances 0.000 description 31
- 150000003254 radicals Chemical class 0.000 description 23
- 239000002253 acid Substances 0.000 description 16
- 238000002360 preparation method Methods 0.000 description 16
- 235000014113 dietary fatty acids Nutrition 0.000 description 10
- 239000006185 dispersion Substances 0.000 description 10
- 229930195729 fatty acid Natural products 0.000 description 10
- 239000000194 fatty acid Substances 0.000 description 10
- VACJHIUSZPBOOF-UHFFFAOYSA-N 3-aminopropane-1,1-diol Chemical compound NCCC(O)O VACJHIUSZPBOOF-UHFFFAOYSA-N 0.000 description 9
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical class OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 8
- 125000002091 cationic group Chemical group 0.000 description 8
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 7
- RKWGIWYCVPQPMF-UHFFFAOYSA-N Chloropropamide Chemical compound CCCNC(=O)NS(=O)(=O)C1=CC=C(Cl)C=C1 RKWGIWYCVPQPMF-UHFFFAOYSA-N 0.000 description 7
- 150000004665 fatty acids Chemical class 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 6
- 239000002270 dispersing agent Substances 0.000 description 6
- 239000003995 emulsifying agent Substances 0.000 description 6
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- 239000002888 zwitterionic surfactant Substances 0.000 description 6
- 125000000129 anionic group Chemical group 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 239000000835 fiber Substances 0.000 description 5
- 239000003381 stabilizer Substances 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 4
- 230000000845 anti-microbial effect Effects 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- 239000003760 tallow Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical class CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 3
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical class OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Chemical class [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 3
- 150000001447 alkali salts Chemical class 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000004205 dimethyl polysiloxane Substances 0.000 description 3
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000003925 fat Substances 0.000 description 3
- 235000019197 fats Nutrition 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- 150000002972 pentoses Chemical class 0.000 description 3
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical class NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 3
- 239000011975 tartaric acid Chemical class 0.000 description 3
- 235000002906 tartaric acid Nutrition 0.000 description 3
- KQIGMPWTAHJUMN-UHFFFAOYSA-N 3-aminopropane-1,2-diol Chemical compound NCC(O)CO KQIGMPWTAHJUMN-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- 235000013162 Cocos nucifera Nutrition 0.000 description 2
- 244000060011 Cocos nucifera Species 0.000 description 2
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 229940124277 aminobutyric acid Drugs 0.000 description 2
- 238000005282 brightening Methods 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 150000002402 hexoses Chemical class 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 239000002563 ionic surfactant Substances 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical class CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- CSIIBLNVEAMNIE-QFIPXVFZSA-N (2S)-2-[2-(dodecylamino)ethylamino]-3-phenylpropanoic acid Chemical compound C(CCCCCCCCCCC)NCCN[C@@H](CC1=CC=CC=C1)C(=O)O CSIIBLNVEAMNIE-QFIPXVFZSA-N 0.000 description 1
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- WDMOQCVHPQTHCX-UHFFFAOYSA-N 2-(3-dodecoxypropylamino)propanoic acid Chemical compound CCCCCCCCCCCCOCCCNC(C)C(O)=O WDMOQCVHPQTHCX-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- VPSXHKGJZJCWLV-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-3-(1-ethylpiperidin-4-yl)oxypyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C(=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2)OC1CCN(CC1)CC VPSXHKGJZJCWLV-UHFFFAOYSA-N 0.000 description 1
- JVKRKMWZYMKVTQ-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]pyrazol-1-yl]-N-(2-oxo-3H-1,3-benzoxazol-6-yl)acetamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C=NN(C=1)CC(=O)NC1=CC2=C(NC(O2)=O)C=C1 JVKRKMWZYMKVTQ-UHFFFAOYSA-N 0.000 description 1
- PTFSLTXIXFNFSI-UHFFFAOYSA-N 2-[bis(2-aminoethyl)amino]tetradecanoic acid Chemical compound CCCCCCCCCCCCC(C(O)=O)N(CCN)CCN PTFSLTXIXFNFSI-UHFFFAOYSA-N 0.000 description 1
- CDMGNVWZXRKJNS-UHFFFAOYSA-N 2-benzylphenol Chemical class OC1=CC=CC=C1CC1=CC=CC=C1 CDMGNVWZXRKJNS-UHFFFAOYSA-N 0.000 description 1
- MOPDEMAOEMHGAS-UHFFFAOYSA-N 2-cyclohexyl-3-methylphenol Chemical class CC1=CC=CC(O)=C1C1CCCCC1 MOPDEMAOEMHGAS-UHFFFAOYSA-N 0.000 description 1
- MVRPPTGLVPEMPI-UHFFFAOYSA-N 2-cyclohexylphenol Chemical class OC1=CC=CC=C1C1CCCCC1 MVRPPTGLVPEMPI-UHFFFAOYSA-N 0.000 description 1
- AOHAPDDBNAPPIN-UHFFFAOYSA-N 3-Methoxy-4,5-methylenedioxybenzoic acid Chemical compound COC1=CC(C(O)=O)=CC2=C1OCO2 AOHAPDDBNAPPIN-UHFFFAOYSA-N 0.000 description 1
- WMUWDPLTTLJNPE-UHFFFAOYSA-N 4-bromo-3,5-dimethylphenol Chemical compound CC1=CC(O)=CC(C)=C1Br WMUWDPLTTLJNPE-UHFFFAOYSA-N 0.000 description 1
- DEXFNLNNUZKHNO-UHFFFAOYSA-N 6-[3-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-3-oxopropyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)C(CCC1=CC2=C(NC(O2)=O)C=C1)=O DEXFNLNNUZKHNO-UHFFFAOYSA-N 0.000 description 1
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- 235000021357 Behenic acid Nutrition 0.000 description 1
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 229920003043 Cellulose fiber Polymers 0.000 description 1
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 description 1
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical class CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
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- 229930091371 Fructose Natural products 0.000 description 1
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
- 239000005715 Fructose Substances 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- LKDRXBCSQODPBY-AMVSKUEXSA-N L-(-)-Sorbose Chemical compound OCC1(O)OC[C@H](O)[C@@H](O)[C@@H]1O LKDRXBCSQODPBY-AMVSKUEXSA-N 0.000 description 1
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- 150000008064 anhydrides Chemical class 0.000 description 1
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- 125000001124 arachidoyl group Chemical group O=C([*])C([H])([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])C([H])([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])C([H])([H])[H] 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
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- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
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- 150000001767 cationic compounds Chemical class 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
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- 125000002704 decyl group Chemical group [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])C([H])([H])C([H])([H])* 0.000 description 1
- AOSQFFSSIMTDFC-UHFFFAOYSA-N diethyl(13-phenyltridecyl)azanium;chloride Chemical compound [Cl-].CC[NH+](CC)CCCCCCCCCCCCCC1=CC=CC=C1 AOSQFFSSIMTDFC-UHFFFAOYSA-N 0.000 description 1
- BGEZRQNCONTESG-UHFFFAOYSA-N diethyl(9-phenylnonyl)azanium;chloride Chemical compound [Cl-].CC[NH+](CC)CCCCCCCCCC1=CC=CC=C1 BGEZRQNCONTESG-UHFFFAOYSA-N 0.000 description 1
- 230000003467 diminishing effect Effects 0.000 description 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-N diphosphoric acid Chemical compound OP(O)(=O)OP(O)(O)=O XPPKVPWEQAFLFU-UHFFFAOYSA-N 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229960001484 edetic acid Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 230000009969 flowable effect Effects 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 230000001408 fungistatic effect Effects 0.000 description 1
- 229930182830 galactose Natural products 0.000 description 1
- 239000000174 gluconic acid Substances 0.000 description 1
- 235000012208 gluconic acid Nutrition 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 229960002449 glycine Drugs 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 230000003165 hydrotropic effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 1
- 229960004903 invert sugar Drugs 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000004310 lactic acid Chemical class 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000002772 monosaccharides Chemical class 0.000 description 1
- 125000001421 myristyl 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])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- RRHLGOOTLYHTEW-UHFFFAOYSA-N n'-[2-(dodecylamino)ethyl]ethane-1,2-diamine Chemical compound CCCCCCCCCCCCNCCNCCN RRHLGOOTLYHTEW-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- MGFYIUFZLHCRTH-UHFFFAOYSA-N nitrilotriacetic acid Chemical compound OC(=O)CN(CC(O)=O)CC(O)=O MGFYIUFZLHCRTH-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 150000002888 oleic acid derivatives Chemical class 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
- 235000005985 organic acids Nutrition 0.000 description 1
- 229940070805 p-chloro-m-cresol Drugs 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- 125000000913 palmityl 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])([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
- 239000006072 paste Substances 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000001205 polyphosphate Substances 0.000 description 1
- 235000011176 polyphosphates Nutrition 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 229940005657 pyrophosphoric acid Drugs 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical class O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 235000019832 sodium triphosphate Nutrition 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 125000004079 stearyl 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])([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])C([H])([H])[H] 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 239000010698 whale oil Substances 0.000 description 1
- 150000003739 xylenols Chemical class 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/402—Amides imides, sulfamic acids
-
- 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
- C11D1/38—Cationic compounds
- C11D1/52—Carboxylic amides, alkylolamides or imides or their condensation products with alkylene oxides
- C11D1/525—Carboxylic amides (R1-CO-NR2R3), where R1, R2 or R3 contain two or more hydroxy groups per alkyl group, e.g. R3 being a reducing sugar rest
-
- 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
- C11D3/001—Softening compositions
Definitions
- ABSTRACT Compositions for the posttreatment of washed laundry the same being adapted for addition to the rinse water either as a solid or in liquid form comprising a softening agent corresponding to the following formula:
- R is alkyl containing 10 to 22 carbon atoms and may be interrupted by ether oxygen atoms in the vicinity of the NH group
- R is alkyl containing seven to 21 carbon atoms, the total number of carbon atoms contained in R. and R amounting to from 23 to 39.
- n is either 3 or 4 and i ith the polyhydroxyl radicals present in the compounds 1 and ll may be etherified with additional polyhydroxylalkyl radicals.
- the aforesaid softening agent (I) or agents (1 and 11) can be employed per se or in combination with other conventional laundry agents such as optical brighteners, deacidifiers, disincrusting agents, colorants, perfumes, antimi il aielesw z te- 8 Claims, No Drawings AGENT FOR THE POST-TREATMENT OF WASHED LAUNDRY
- This invention relates to softening agents for use in the postor in an industrial laundry.
- cationic substances are added to the final rinse, which substances contain at least two fatty radicals of high molecular weight in their molecules.
- dialkyl dimethyl ammonium salts that are dispersable in water have become popular for this purpose, each of the two alkyl radicals in this latter compound contains 16 to 18 carbon atoms.
- These cationic softening agents are usually marketed in the form of their aqueous dispersions.
- R represents an alkyl radical having to 22, preferably 12 to 20 and most preferably 16 to 18 carbon atoms
- R represents an alkyl radical having seven to 21, preferably H to 19, and most preferably l5 to 17 carbon atoms
- n is either of the whole numbers 3 or 4, further wherein the alkyl radical R, can be interrupted by an ether oxygen atom in the vicinity of the NH group, and the sum of the carbon atoms contained in R, and R amounts to from 23 to 39, preferably from 27 to 35.
- These softening agents can be employed in the treatment of washed textiles, alone or together with other conventional laundry posttreatment agents, such as acidifiers or disincrusting agents, optical brighteners and/or heavy metal-free, nonoxidizing, watersoluble antimicrobial agents, as well as surfactants provided that the quantity of surfactants present does not exceed that of the textile-softening agent.
- laundry posttreatment agents such as acidifiers or disincrusting agents, optical brighteners and/or heavy metal-free, nonoxidizing, watersoluble antimicrobial agents, as well as surfactants provided that the quantity of surfactants present does not exceed that of the textile-softening agent.
- antimicrobial agents can include zwitter-ionic surfactants, but in this case, the quantity of zwitter-ionic surfactants is always less than that of the textile-softening agent present.
- R is alkyl containing 10 to 22 carbon atoms and may be interrupted by ether oxygen atoms in the vicinity of the NH, group
- R is alkyl containing seven to 21 carbon atoms, the total number of carbon atoms contained in R, and R amounting to from 23 to 39
- n is either 3 or 4
- Z is either wherein the polyhydroxyl radicals present in the compounds I and Il may be etherified with additional polyhydroxyalkyl radicals.
- the radical Z may be a glycerylamine or a polyglycerylamine having two to 15 and preferably two to five glyceryl radicals in their molecules.
- the compounds of Formula I will hereinafter be called glycerylamides" for the sake of simplicity.
- the aforesaid softening agent (l) or agents (l and H) can be employed per se or in combination with other conventional laundry agents such as optical brighteners, deacidifiers, disincrusting agents, colorants, perfumes, antimicrobial agents, etc.
- the textile-softening agents present in the preparations of the invention consist of from 10 to 100 percent by weight, and preferably to from 20 to 100 percent by weight, of compounds of Formula I, and of from O to 90 percent by weight, and preferably of from 0 to percent by weight of compounds of Formula ll.
- the textiles rinsed with these products have, after drying, not only a high degree of fullness and softness, but they also possess excellent absorbency. Furthermore, the softening agents of the invention are quite compatible with an ionic optical brightening agent. If any of the above-mentioned antimicrobial agents are used, not only are any microbes that might be present in the washed textiles or in the rinse water killed, but in many instances antimicrobial properties are conferred upon the posttreated textiles.
- polyhydroxylalkyl radicals present in the textile softeners of Formula ll can be derived from hexoses, particularly monosaccharides, such as glucose, mannose, galactose, fructose, sorbose, or their mixtures, as for example, invert sugar;
- the glycamides are of particular practical interest and accordingly this term shall be used hereinafter to designate all of the compounds of Formula II.
- the alkyl radicals of the amines from which the textile sof teners to be used according to the invention can be prepared can, similar to the radicals of the amidelike bound fatty acids, be saturated or unsaturated, straight chained or branched, and of synthetic or natural origin. Accordingly, the radicals R can be derived from decyl, lauryl, myristyl, cetyl, stearyl, oleyl, arachyl or behenyl amine.
- the carbon chains of these alkyl radicals can also be interrupted by an ether oxygen atom in the vicinity of the nitrogen atom, preferably between carbon atoms 2 and 3 or 3 and 4 (counting from the nitrogen atom).
- the fatty acid radicals R CO can be derived from capric acid, lauric, myristic, palmitic, stearic, oleic, arachic or behenic acid. Textile softeners can also be used in which the amine radicals and/or the fatty acid radicals are present as isomer mixtures, as they are, for example, in fats and oils of natural origin. Accordingly, the radicals R and R CO can be derived from the fats and oils of plants, land or marine animals, such as for example, coconut oil, palm oil, linseed oil, cottonseed oil, peanut oil, castor oil, etc., hog lard, tallow or fish or whale oils, or from fractions of the fatty acids contained in these fats. The aforesaid radicals are to be preferably of a substantially saturated nature.
- the preparations for use as laundry posttreatment agents according to the invention can be in the form of liquids, pastes or solids (such as powders, flakes, beads and the like), in which the textile softeners are finely divided.
- the carrier substances or solvents or diluents, as the case may be, are required to be readily soluble in water and more specifically must be capable of rapidly dissolving in the washing medium after the preparation has been added to the rinse water, and so that a dispersion of the finely divided textile softening agents in the rinse water will be obtained in a short time.
- the concentration as required for use amounts generally to about 0.05 to 2 g./l. and preferably to 0.1 to 0.5 g./l.
- the posttreatment agents can be used already in the first rinse, even if the residues of the detergent solution have not as yet been completely rinsed out from the laundry. Since it is an established practice to add the softening agent to the final rinse, the same practice can of course be followed when using the posttreatment agents according to the invention.
- the wet laundry can be dried in the conventional manner.
- the dry laundry is soft and full, and has a pleasant feel, which is readily apparent, particularly in the case of those articles which come in contact with the skin, such as underclothing, bed linens and handkerchiefs.
- Bath towels in particular show a remarkably good absorbency.
- Dish towels which have been laundered as above also show this particularly satisfactory absorbency.
- the damp laundry soft-rinsed according to the invention yields its moisture more rapidly in drying than laundered articles which have not been postrinsed with the preparations according to the invention. Still further, the laundered articles thus treated iron more easily than the same articles not so treated.
- the solid carrier substances which are included in the compositions according to the invention are water-soluble inorganic or organic substances having a weakly alkaline, neutral or weakly acid reaction.
- inorganic or organic salts as for example, the alkali salts of sulfuric acid or orthoor pyrophosphoric acid.
- Salts of organic acids are also suitable such as for instance the nonsurface active salts of carboxylic acids or oxycarboxylic acids having one to and preferably one to six carbon atoms, such as for example salts of acetic acid, propionic acid, lactic acid, citric acid, tartaric acid, etc.
- water-soluble inorganic or organic acid amides or their salts may be employed as solid diluents. These include, for example, amidosulfonic acid salts,
- amidophosphonic acid salts and water-soluble amides of carboxylic acids, such as urea, acetamide and the like.
- Solid polyethylene glycols can also be advantageously employed as carrier substances.
- the solid posttreatment agents can be prepared, for example, by spraying a solution or dispersion of the textile softener in a suitable liquid onto the finely divided carrier substances present in the solid state. It is also possible, however, to atomized aqueous solutions or suspensions of the textile softeners containing dissolved or dispersed carrier substances, thereby directly obtaining a readily soluble powder or granular product. Still further, solutions or dispersions of the textile softeners in molten urea or in molten polyethylene glycols can be atomized or otherwise converted into readily soluble powder or granular products.
- the textile softeners which are moderately soluble in water are dispersed in an aqueous liquid or in an organic solvent. It is advantageous to first dissolve the textile softeners in a suitable water-soluble organic solvent and to thereafter combine the solutions thus obtained with water, whereupon the solid textile softeners separate in finely divided form, the organic solvent serving as solubilizer.
- the resultant aqueous dispersions can, of course, contain any of the abovemamed solid carrier substances in solution, unless the stability of the dispersion be thereby adversely affected. In many cases, however, the stability is even improved.
- Urea, acetamide and the alkali salts of lower carboxylic acids or oxycarboxylic acids containing up to six carbon atoms are suitable for this purpose.
- the latter substances can be used in place of or together with water-soluble organic solvents, which then can serve as solubilizers.
- Soluble salts, of aromatic or alkylaromatic sulfonic acids having six to 10 carbon atoms can also be advantageously used in this connection.
- suitable organic solvents include for example, monovalent or polyvalent alcohols having one to four carbon atoms, or ether alcohols, for instance, the monoethers formed from the aforesaid monovalent alcohols with ethylene glycol, diethylene glycol, propylene glycol, butylene glycol, or the monoor diethers formed from the aforesaid monovalent al cohols with glycerin.
- the textile softeners are additionally soluble in water-soluble lower ketones.
- any of the conventional dispersing and emulsifying agents or emulsion stabilizers can be added for effecting the stabilization of the aqueous dispersions.
- Anionic or nonionic surfactants the action of which is based on the simultaneous presence of a hydrophobic and a hydrophilic radical in their molecule are suitable as dispersing or emulsifying agents.
- the hydrophobic radical generally consists of an alkyl group having eight to 20 and preferably 12m 18 carbon atoms.
- Anionic or nonionic groups are suitable as hydrophilic radicals.
- anionic groups there may be mentioned carboxyl, sulfonic acid or sulfuric acid semiester groups, and as nonionic groups polyhydroxyalkyl radicals or polyethylene ether chains.
- alkylbenzenesulfonates fatty alcohol sulfates, fatty alcohol glycol ether sulfates having one to five ethylene glycol ether radicals in their molecules, fatty acid monoglycerides, polyethylene glycol ethers of fatty alcohols or alkyl phenols having five to 20 ethylene glycol ether radicals in their molecules are suitable as dispersing and emulsifying agents.
- the quantity of these surfactants is required to always amount to less than the quantity of the textile softeners, and preferably it is to be substantially less, not exceeding 50 percent and preferably amounting to from 5 to 25 percent of the quantity of the textile softeners.
- Suitable emulsion stabilizers include the water-soluble colloids, such as the salts of ether carboxylic acids or ether sulfonic acids of cellulose, cellulose sulfate, polyacrylic acid or polymethacrylic acid salts, water-soluble polyacrylamides and polyethylene glycols, preferably those having a molecular weight greater than 600.
- emulsion stabilizers produce a great increase in the viscosity of the aqueous solutions, and therefore they are used in quantities of less than 2 percent and preferably of less than 1 percent so that the posttreatment agents will still be readily flowable or pourable in nature.
- Others, particularly the polyethylene glycols can be used in substantially greater quantities, without raising the viscosity to undesirable levels.
- the softening agents according to the invention and the compositions containing such softening agents can advantageously be combined with other substances which have heretofore been used as posttreatment agents.
- these include, for example, optical brighteners, deacidifying and disincrusting agents, colorants, perfumes, heavy metal-free, nonoxidizing antimicrobial agents, etc. These substances can be incorporated into the solid or liquid posttreatment agents according to the invention.
- the combined use of the above-described softening agents with optical brighteners is to be considered as an important and novel feature of the invention.
- the brighteners are intended mainly for cellulose fibers, but brighteners for cellulose and/or other fibers, especially synthetic fibers, can be used as well.
- the following types of brighteners can be used:
- Suitable additives for deacidification and/or for the removal of ash or other fiber incrustations include the nonoxidizing acids which have been found to be not harmful to the fibers to be treated and particularly those additives which form soluble alkaline earth salts, and complex compound formers.
- the acid reacting substances include for example amidosulfuric acid, urea compounds of orthophosphoric acid or solid or liquid organic acid like citric acid.
- the complex compound formers include for example tripolyphosphates or the higher but still water soluble polyphosphates of alkalies, nitrilotriacetic acid, ethylenediamine tetracetic acid, N-oxyethylethylenediaminetriacetic acid and other conventional organic complex compound forming agents, such as the salts of certain di-, trior tetraphosphonic acids.
- antimicrobial agents as used herein is understood to mean both bactericidal and bacteriostatic, and fungicidal and/or fungistatic products.
- the antimicrobial agents are required to be water soluble either per se or in the form of their salts.
- suitable antimicrobial agents for use herein are formaldehyde, halogenated phenols, nitrated monoor polyalcohols, and antimicrobial surfactants. If the antimicrobial agents are zwitter-ionic surfactants, their quantity is required to be less than the quantity of the textile-sofsalts of tening agent and preferably the quantity of zwitter-ionic surface-active antimicrobial agent amounts to no more than 50 percent of the quantity of the textile softening agent.
- halogenated phenols which may be used as antimicrobials
- chlorination and bromination products of phenol such as pentachlorophenol
- halogenated cresols xylenols, such as 4-bromo-3,5-xylenol or halogenated cyclohexylphenols, methylcyclohexylphenols or benzylphenols.
- water-solubleantimicrobial substances of the cationic or hybrid (zwitter) ionic surfactant type which serve in the final posttreatment agents also as dispersing agents.
- quaternary ammonium compounds which contain on the nitrogen atom thereof an aliphatic hydrocarbon radical containing eight to l8, and preferably 10 to 14 carbon atoms, or alternatively contain on the nitrogen atom at least one aromatic radical or a radical having double bonds, the latter radical being linked to the nitrogen atom by an aliphatic carbon atom.
- the following are instances of the cationic compounds suitable for use in the invention include: diethylbenzyldodecyl ammonium chloride, diethylbenzyloctyl ammonium chloride, and dibutylallyl, methylethylbenzyl,
- tertiary amines suitable for use which can be prepared by condensing a primary or secondary amine containing up to four basic nitrogen atoms and one aliphatic or alkylaromatic radical having eight to 18 and preferably eight to 14 aliphatic carbon atoms with a phenol or lower aliphatic aldehyde, preferably formaldehyde or acetaldehyde.
- the phenol employed in the condensation reaction may have in its molecule a plurality of sites capable of condensation, and these may be substituted with lower alkyl, alkoxy or benzyl radicals containing up to 4 carbon atoms.
- the phenol, alkyl, alkoxy and benzyl radicals may additionally be substituted with chlorine or bromine atoms and/or with nitro groups.
- condensation products include, for instance, the following compounds: oxybenzyloctylamine, oxybenzyl dodecyldiethylenetriamine, (2-oxy-5-chloro-6-methylbenzyl)- dodecyldiethylenetriamine, (2-oxy-5-methylbenzyl)-octyldiethyl-enetriamine, (2-oxy-5-chloro-4,fi-dimethylbenzyl)-octyldiethylene-triamine, (tris-oxybenzyl )-dodecyltn'ethylenetriamine, o,o-bis-(tetradecylaminomethyl)-phenol, (octyl-diethylenetriaminomethyl)-p-cresol, o,o-bis-(dodecyldiethylenetriaminomethyl)
- hybrid or zwitter ionic surfactants which have achieved particular importance as antimicrobials include compounds of the aminocarboxylic acid, polyaminocarboxylic acid and betaine type.
- aminocarboxylic and polyaminocarboxylic acid antimicrobial agents are compounds having the following structural formula:
- R represents an alkyl or alkylaryl radical of high molecular weight, preferably such a hydrocarbon radical having six to 18 and most preferably eight to 14 aliphatic carbon atoms
- R represents an ethylene or propylene radical
- x 20 represents a whole number of from one to six
- R represents an aliphatic-aromatic or aromatic bridge having one to six carbon atoms.
- the following compounds are illustrative of aminocarboxylic and polyaminocarboxylic compounds having the above-mentioned formula: dodecylaminopropy[glycine, tetradecylaminoethyl-B-alanine, dodecyl-di-(aminoethyl)-glycine, dodecylaminoisopropylaminomethylsalicyclic acid, hexadecyl-tri-(aminoethyl)-B-aminobutyric acid, dodecylbenzylaminopropyl-B-alanine, octylphenoxyethyl-di- (aminoethyl)-glycine, dodecylaminoethylphenylalanine, dodecylaminoethylaminobenzoic acid, etc.
- the radical R can also be interrupted by an ether oxygen atom, as is the case, for example, in the following compounds: dodecyloxypropylaminopropionic acid, lauryl-l,3-oxypropyl- B-aminobutyric acid, C, -alkyloxyethylaminoacetic acid, dodecyll ,2-0xypropylaminomethylsalicylic acid, octylphenoxyethylaminobenzoic acid.
- the compounds that can be used according to the invention furthermore include carboxybetaines of the formula:
- R has the same meaning as in the preceding formula, R represents an ethylene or propylene group, and R and R represent aliphatic radicals of low molecular weight, R represents an aliphatic bridge of low molecular weight, X an ether oxygen atom or the CONH group.
- carboxybetaine compounds are lauryl-l,3-amidopropyldimethylaminoacetic acid, lauryloxyethyl-di-(hydroxyethyl)- aminoacetic acid, etc.
- posttreatment agents according to the invention are in the form of solid products, they advantageously have the following composition:
- textile softeners 3095% preferably 70-90%, by weight, solid carrier substance 0-20%, preferably 1l5%, by weight, optical brighteners, most preferably a quantity amounting to from 5 to 25% of the quantity of the textile softener used.
- antimicrobial agents 0.05-20%, preferably 120%, by weight, of the above-named antimicrobial agents; wherein if these agents are antimicrobial, zwitter-ionic surfactants, their quantity is always to be smaller than the quantity of textile softener, amounting preferably to no more than 50%, and most preferably to 5 to 25%, of the quantity of the textile softener.
- post-treatment agents according to the invention are in the form of liquid preparations, they advantageously have the following composition:
- optical brighteners most preferably a quantity as to amount to 5 to 25% of the quantity of the textile softener.
- the quantity of the textile softener preferably no more than 50% and most preferably to 5 to 25% of the quantity thereof.
- the polyglycerylamide derivative has three CH CHOHCH O radicals per molecule.
- the ethoxylated dimethyl polysiloxane incorporated into a number of preparations as an emulsifier is marketed by Wackerchemie GmbH, Kunststoff, under the trade name DC 202.
- composition for softening laundered textiles consisting essentially of Rr-IIT-C -R2 and I Ri-NCO-R2 (IT) CHg-(CHOH) ,,CH OH wherein R, is
- alkyl of 10 to 22 carbon atoms or I 2. alkyl of 10 to 22 carbon atoms with an ether oxygen linkage in the vicinity of the nitrogen atom, R is alkyl of seven to 21 carbon atoms, R +R have 23 to 39 carbon atoms,
- Z is (1) H2-CHOH-CH2OH 2 CH2OIPIIJJHCH2OH, or
- composition according to claim 1 wherein (I) and (ii) constitute about 5-70 weight percent, and about 30-95 weight percent of solid carrier substance selected from the group consisting of salts of sulfuric acid, phosphoric acids, or aliphatic carboxylic acids containing up to about carbon atoms, urea, acetamide and polyethylene glycols.
- composition according to claim 1 including 0.5-20 weight percent of a heavy metal-free, nonoxidizing water-soluble antimicrobial agent.
- a method for treating a textile-fabric article comprising laundering said article, and thereafter rinsing said article with water containing dissolved therein in the range of 0.05 to 2 grams per liter of a compound of the formula wherein: R, is
- alkyl of 10 to 22 carbon atoms or 2. alkyl of 10 to 22 carbon atoms with an ether oxygen linkage between either the 2 and 3 or 3 and 4 carbon atoms from the nitrogen atom, R is alkyl of seven to 21 carbon atoms, R,+R have 23 to 39 carbons atoms, and
- R has 12 to 20 carbon atoms, wherein R has 11 to 19 carbon atoms, and wherein R,+R have a total of 27 to 35 carbon atoms.
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Abstract
Compositions for the posttreatment of washed laundry, the same being adapted for addition to the rinse water either as a solid or in liquid form comprising a softening agent corresponding to the following formula: ALONE OR IN COMBINATION WITH A SOFTENING AGENT CORRESPONDING TO THE FOLLOWING FORMULA: WHEREIN R1 is alkyl containing 10 to 22 carbon atoms and may be interrupted by ether oxygen atoms in the vicinity of the NH2 group, R2 is alkyl containing seven to 21 carbon atoms, the total number of carbon atoms contained in R1 and R2 amounting to from 23 to 39, n is either 3 or 4 and Z is either THE POLYHYDROXYL RADICALS PRESENT IN THE COMPOUNDS I and II may be etherified with additional polyhydroxylalleyl radicals. The aforesaid softening agent (I) or agents (I and II) can be employed per se or in combination with other conventional laundry agents such as optical brighteners, deacidifiers, disincrusting agents, colorants, perfumes, antimicrobial agents, etc.
Description
Primary Eicdminer l-lerbert B. Guynn United States Patent Heins et al.
[ 1 Feb. 22, 1972 [54] AGENT FOR THE POST-TREATMENT OF WASHED LAUNDRY [72] Inventors: Arnold Heins, Hilden/Rhineland; Hans- Werner Eckert; Horst Bellinger, both of S 2 qqrftellei stm nxw .1 [73] Assignee: Henkel & Cie GmbH, Dusseldorf- Holthausen, Germany [22] Filed: July 10, 1968 [21] Appl. No.: 743,610
[30] Foreign Application Priority Data Aug. 14, 1967 Germany ..H 63600 [52] U.S.Cl. ..252/8.8, 117/47 R, 117/66, 117/139 SF, 1l7/139.5 CQ, 252/8.6, 252/89 [51] Int. Cl. ..D06m 13/40 [58] Field ofSearch ..252/8.8, 152, 137; 117/139 SF, 117/47 R [56] References Cited UNITED STATES PATENTS 2,002,613 5/1935 Orthner et a1 ..252/8.8 X 2,334,852 ll/l943 Weisberg et a1. ..252/8.8 X 3,122,502 2/1964 Waldman ..252/8.8 3,349,033 10/1967 Zuccarelli ....252/8.75 3,356,526 12/1967 Waldman et al. 17/100 3,424,680 1/1969 Van Loo et a1. ..252/8.8 3,454,494 7/1969 Clark et a1. ..252/8.8
AttorneyBurgess, Dinklage & Sprung [57] ABSTRACT Compositions for the posttreatment of washed laundry, the same being adapted for addition to the rinse water either as a solid or in liquid form comprising a softening agent corresponding to the following formula:
wherein R, is alkyl containing 10 to 22 carbon atoms and may be interrupted by ether oxygen atoms in the vicinity of the NH group, R is alkyl containing seven to 21 carbon atoms, the total number of carbon atoms contained in R. and R amounting to from 23 to 39. n is either 3 or 4 and i ith the polyhydroxyl radicals present in the compounds 1 and ll may be etherified with additional polyhydroxylalkyl radicals. The aforesaid softening agent (I) or agents (1 and 11) can be employed per se or in combination with other conventional laundry agents such as optical brighteners, deacidifiers, disincrusting agents, colorants, perfumes, antimi il aielesw z te- 8 Claims, No Drawings AGENT FOR THE POST-TREATMENT OF WASHED LAUNDRY This invention relates to softening agents for use in the postor in an industrial laundry.
This undesirable loss of good feel in the laundering process can be avoided if cationic substances are added to the final rinse, which substances contain at least two fatty radicals of high molecular weight in their molecules. in practice, dialkyl dimethyl ammonium salts that are dispersable in water have become popular for this purpose, each of the two alkyl radicals in this latter compound contains 16 to 18 carbon atoms. These cationic softening agents are usually marketed in the form of their aqueous dispersions.
Although when these cationic softening agents are used in the final rinse the undesirable hardness is not found in the laundry after drying, the use of these products entails certain disadvantages. if the detergent dissolved in the final wash has not been entirely removed from the clothing, which may be the case, particularly in tub-type washing machines, precipitates are formed between the cationic softening agents and the anionic wash-active substances, thereby diminishing or obstructing the softening effect. Furthermore, these precipitates can themselves be deposited on the fibers and cause yellowing of the laundered items. Furthermore, the absorbency of the washed goods is adversely affected by the softening agents as known in the prior art. Even in the case of drum-type washing machines, in which the rinsing action is generally better than it is in tub-type machines, a reduction of the absorbency of the posttreated clothing can be observed, apparently because small amounts of the anionic wash-active substances are fixed on the fibers and then react with the cationic softening agents.
In U.S. Pat. application Ser. No. 656,136 there are described preparations for use in the posttreatment of washed laundry, which contain as textile-softening agent compounds having the following formula:
wherein R, represents an alkyl radical having to 22, preferably 12 to 20 and most preferably 16 to 18 carbon atoms, R represents an alkyl radical having seven to 21, preferably H to 19, and most preferably l5 to 17 carbon atoms, and n is either of the whole numbers 3 or 4, further wherein the alkyl radical R, can be interrupted by an ether oxygen atom in the vicinity of the NH group, and the sum of the carbon atoms contained in R, and R amounts to from 23 to 39, preferably from 27 to 35. These softening agents can be employed in the treatment of washed textiles, alone or together with other conventional laundry posttreatment agents, such as acidifiers or disincrusting agents, optical brighteners and/or heavy metal-free, nonoxidizing, watersoluble antimicrobial agents, as well as surfactants provided that the quantity of surfactants present does not exceed that of the textile-softening agent.
In. U.S. Pat. application Ser. No. 749,596, now pending preparations are disclosed corresponding to the above but additionally containing at least one heavy metal-free, nonoxidizing, water-soluble antimicrobial agent. The antimicrobial agents can include zwitter-ionic surfactants, but in this case, the quantity of zwitter-ionic surfactants is always less than that of the textile-softening agent present.
It is an object of this invention to eliminate the disadvantages of the prior art methods of posttreating laundry by the provision of a new and improved softening agent.
It is an additional object of the invention to provide laundry posttreatment agents which contain the active softening agent of the invention in a form designed for easy and practical use.
These and other objects and advantages of the invention will become apparent from a further consideration of the following disclosure.
According to the invention it has now been found that laundry treated, after washing, with an aqueous solution or dispersion of a softening agent, in solid or liquid form corresponding to the following formula:
alone or in combination with a softening agent corresponding to the following formula:
wherein R, is alkyl containing 10 to 22 carbon atoms and may be interrupted by ether oxygen atoms in the vicinity of the NH, group, R is alkyl containing seven to 21 carbon atoms, the total number of carbon atoms contained in R, and R amounting to from 23 to 39, n is either 3 or 4, and Z is either wherein the polyhydroxyl radicals present in the compounds I and Il may be etherified with additional polyhydroxyalkyl radicals. The radical Z may be a glycerylamine or a polyglycerylamine having two to 15 and preferably two to five glyceryl radicals in their molecules. The compounds of Formula I will hereinafter be called glycerylamides" for the sake of simplicity. The aforesaid softening agent (l) or agents (l and H) can be employed per se or in combination with other conventional laundry agents such as optical brighteners, deacidifiers, disincrusting agents, colorants, perfumes, antimicrobial agents, etc.
The textile-softening agents present in the preparations of the invention consist of from 10 to 100 percent by weight, and preferably to from 20 to 100 percent by weight, of compounds of Formula I, and of from O to 90 percent by weight, and preferably of from 0 to percent by weight of compounds of Formula ll.
The textiles rinsed with these products have, after drying, not only a high degree of fullness and softness, but they also possess excellent absorbency. Furthermore, the softening agents of the invention are quite compatible with an ionic optical brightening agent. If any of the above-mentioned antimicrobial agents are used, not only are any microbes that might be present in the washed textiles or in the rinse water killed, but in many instances antimicrobial properties are conferred upon the posttreated textiles.
The preparation of the polyglycerylamides is described in U.S. Pat. application Ser. No. 743,595, now abandoned, i.e., by reacting an amine R,Nl-l wherein R, is as defined before with a member selected from the group of polyglycerin-l,2- monochlorhydrin glyceringlycide ethers and polyglycerin glycide ethers and thereafter acylating the resulting secondary amine with a member selected from the group consisting of halides, anhydrides and esters of a carboxylic acid R COOH wherein RR is as defined before.
The polyhydroxylalkyl radicals present in the textile softeners of Formula ll can be derived from hexoses, particularly monosaccharides, such as glucose, mannose, galactose, fructose, sorbose, or their mixtures, as for example, invert sugar;
however, they also can be derived from their oligomers such as maltose. The polyhydroxyalkyl radicals can also be derived from pentose, mixtures of various pentoses or mixtures of pentoses and hexoses. The glycamides are of particular practical interest and accordingly this term shall be used hereinafter to designate all of the compounds of Formula II.
The alkyl radicals of the amines from which the textile sof teners to be used according to the invention can be prepared can, similar to the radicals of the amidelike bound fatty acids, be saturated or unsaturated, straight chained or branched, and of synthetic or natural origin. Accordingly, the radicals R can be derived from decyl, lauryl, myristyl, cetyl, stearyl, oleyl, arachyl or behenyl amine. The carbon chains of these alkyl radicals can also be interrupted by an ether oxygen atom in the vicinity of the nitrogen atom, preferably between carbon atoms 2 and 3 or 3 and 4 (counting from the nitrogen atom).
The fatty acid radicals R CO can be derived from capric acid, lauric, myristic, palmitic, stearic, oleic, arachic or behenic acid. Textile softeners can also be used in which the amine radicals and/or the fatty acid radicals are present as isomer mixtures, as they are, for example, in fats and oils of natural origin. Accordingly, the radicals R and R CO can be derived from the fats and oils of plants, land or marine animals, such as for example, coconut oil, palm oil, linseed oil, cottonseed oil, peanut oil, castor oil, etc., hog lard, tallow or fish or whale oils, or from fractions of the fatty acids contained in these fats. The aforesaid radicals are to be preferably of a substantially saturated nature.
The preparations for use as laundry posttreatment agents according to the invention can be in the form of liquids, pastes or solids (such as powders, flakes, beads and the like), in which the textile softeners are finely divided. The carrier substances or solvents or diluents, as the case may be, are required to be readily soluble in water and more specifically must be capable of rapidly dissolving in the washing medium after the preparation has been added to the rinse water, and so that a dispersion of the finely divided textile softening agents in the rinse water will be obtained in a short time. The concentration as required for use amounts generally to about 0.05 to 2 g./l. and preferably to 0.1 to 0.5 g./l.
The posttreatment agents can be used already in the first rinse, even if the residues of the detergent solution have not as yet been completely rinsed out from the laundry. Since it is an established practice to add the softening agent to the final rinse, the same practice can of course be followed when using the posttreatment agents according to the invention.
After the rinse, the wet laundry can be dried in the conventional manner. The dry laundry is soft and full, and has a pleasant feel, which is readily apparent, particularly in the case of those articles which come in contact with the skin, such as underclothing, bed linens and handkerchiefs. Bath towels in particular show a remarkably good absorbency. Dish towels which have been laundered as above also show this particularly satisfactory absorbency. Further, the damp laundry soft-rinsed according to the invention yields its moisture more rapidly in drying than laundered articles which have not been postrinsed with the preparations according to the invention. Still further, the laundered articles thus treated iron more easily than the same articles not so treated.
The solid carrier substances which are included in the compositions according to the invention are water-soluble inorganic or organic substances having a weakly alkaline, neutral or weakly acid reaction. In the manufacture of solid preparations, there are most advantageously employed inorganic or organic salts, as for example, the alkali salts of sulfuric acid or orthoor pyrophosphoric acid. Salts of organic acids, however, are also suitable such as for instance the nonsurface active salts of carboxylic acids or oxycarboxylic acids having one to and preferably one to six carbon atoms, such as for example salts of acetic acid, propionic acid, lactic acid, citric acid, tartaric acid, etc. In addition, water-soluble inorganic or organic acid amides or their salts may be employed as solid diluents. These include, for example, amidosulfonic acid salts,
amidophosphonic acid salts and water-soluble amides of carboxylic acids, such as urea, acetamide and the like. Solid polyethylene glycols can also be advantageously employed as carrier substances.
The solid posttreatment agents can be prepared, for example, by spraying a solution or dispersion of the textile softener in a suitable liquid onto the finely divided carrier substances present in the solid state. It is also possible, however, to atomized aqueous solutions or suspensions of the textile softeners containing dissolved or dispersed carrier substances, thereby directly obtaining a readily soluble powder or granular product. Still further, solutions or dispersions of the textile softeners in molten urea or in molten polyethylene glycols can be atomized or otherwise converted into readily soluble powder or granular products.
In the preparation of liquid, aqueous concentrates, the textile softeners which are moderately soluble in water are dispersed in an aqueous liquid or in an organic solvent. It is advantageous to first dissolve the textile softeners in a suitable water-soluble organic solvent and to thereafter combine the solutions thus obtained with water, whereupon the solid textile softeners separate in finely divided form, the organic solvent serving as solubilizer. The resultant aqueous dispersions can, of course, contain any of the abovemamed solid carrier substances in solution, unless the stability of the dispersion be thereby adversely affected. In many cases, however, the stability is even improved. Urea, acetamide and the alkali salts of lower carboxylic acids or oxycarboxylic acids containing up to six carbon atoms are suitable for this purpose. The latter substances can be used in place of or together with water-soluble organic solvents, which then can serve as solubilizers. Soluble salts, of aromatic or alkylaromatic sulfonic acids having six to 10 carbon atoms can also be advantageously used in this connection.
Examples of suitable organic solvents include for example, monovalent or polyvalent alcohols having one to four carbon atoms, or ether alcohols, for instance, the monoethers formed from the aforesaid monovalent alcohols with ethylene glycol, diethylene glycol, propylene glycol, butylene glycol, or the monoor diethers formed from the aforesaid monovalent al cohols with glycerin. The textile softeners are additionally soluble in water-soluble lower ketones.
In accordance with the invention any of the conventional dispersing and emulsifying agents or emulsion stabilizers can be added for effecting the stabilization of the aqueous dispersions.
Anionic or nonionic surfactants, the action of which is based on the simultaneous presence of a hydrophobic and a hydrophilic radical in their molecule are suitable as dispersing or emulsifying agents. The hydrophobic radical generally consists of an alkyl group having eight to 20 and preferably 12m 18 carbon atoms. Anionic or nonionic groups are suitable as hydrophilic radicals. As anionic groups there may be mentioned carboxyl, sulfonic acid or sulfuric acid semiester groups, and as nonionic groups polyhydroxyalkyl radicals or polyethylene ether chains. Accordingly, alkylbenzenesulfonates, fatty alcohol sulfates, fatty alcohol glycol ether sulfates having one to five ethylene glycol ether radicals in their molecules, fatty acid monoglycerides, polyethylene glycol ethers of fatty alcohols or alkyl phenols having five to 20 ethylene glycol ether radicals in their molecules are suitable as dispersing and emulsifying agents. The quantity of these surfactants, however, is required to always amount to less than the quantity of the textile softeners, and preferably it is to be substantially less, not exceeding 50 percent and preferably amounting to from 5 to 25 percent of the quantity of the textile softeners.
Suitable emulsion stabilizers include the water-soluble colloids, such as the salts of ether carboxylic acids or ether sulfonic acids of cellulose, cellulose sulfate, polyacrylic acid or polymethacrylic acid salts, water-soluble polyacrylamides and polyethylene glycols, preferably those having a molecular weight greater than 600.
Many of these emulsion stabilizers produce a great increase in the viscosity of the aqueous solutions, and therefore they are used in quantities of less than 2 percent and preferably of less than 1 percent so that the posttreatment agents will still be readily flowable or pourable in nature. Others, particularly the polyethylene glycols, can be used in substantially greater quantities, without raising the viscosity to undesirable levels.
The softening agents according to the invention and the compositions containing such softening agents can advantageously be combined with other substances which have heretofore been used as posttreatment agents. These include, for example, optical brighteners, deacidifying and disincrusting agents, colorants, perfumes, heavy metal-free, nonoxidizing antimicrobial agents, etc. These substances can be incorporated into the solid or liquid posttreatment agents according to the invention.
The combined use of the above-described softening agents with optical brighteners is to be considered as an important and novel feature of the invention. The brighteners are intended mainly for cellulose fibers, but brighteners for cellulose and/or other fibers, especially synthetic fibers, can be used as well. For example, the following types of brighteners can be used:
Suitable additives for deacidification and/or for the removal of ash or other fiber incrustations include the nonoxidizing acids which have been found to be not harmful to the fibers to be treated and particularly those additives which form soluble alkaline earth salts, and complex compound formers. The acid reacting substances include for example amidosulfuric acid, urea compounds of orthophosphoric acid or solid or liquid organic acid like citric acid. The complex compound formers include for example tripolyphosphates or the higher but still water soluble polyphosphates of alkalies, nitrilotriacetic acid, ethylenediamine tetracetic acid, N-oxyethylethylenediaminetriacetic acid and other conventional organic complex compound forming agents, such as the salts of certain di-, trior tetraphosphonic acids.
The term antimicrobial agents as used herein is understood to mean both bactericidal and bacteriostatic, and fungicidal and/or fungistatic products. The antimicrobial agents are required to be water soluble either per se or in the form of their salts. Examples of suitable antimicrobial agents for use herein are formaldehyde, halogenated phenols, nitrated monoor polyalcohols, and antimicrobial surfactants. If the antimicrobial agents are zwitter-ionic surfactants, their quantity is required to be less than the quantity of the textile-sofsalts of tening agent and preferably the quantity of zwitter-ionic surface-active antimicrobial agent amounts to no more than 50 percent of the quantity of the textile softening agent.
As instances of halogenated phenols which may be used as antimicrobials, there may be mentioned, for example, chlorination and bromination products of phenol, such as pentachlorophenol, and also halogenated cresols, xylenols, such as 4-bromo-3,5-xylenol or halogenated cyclohexylphenols, methylcyclohexylphenols or benzylphenols.
There may also be used the water-solubleantimicrobial substances of the cationic or hybrid (zwitter) ionic surfactant type, which serve in the final posttreatment agents also as dispersing agents. 1
lnstances of cationic substances which are suitable as antimicrobials include quaternary ammonium compounds which contain on the nitrogen atom thereof an aliphatic hydrocarbon radical containing eight to l8, and preferably 10 to 14 carbon atoms, or alternatively contain on the nitrogen atom at least one aromatic radical or a radical having double bonds, the latter radical being linked to the nitrogen atom by an aliphatic carbon atom. The following are instances of the cationic compounds suitable for use in the invention include: diethylbenzyldodecyl ammonium chloride, diethylbenzyloctyl ammonium chloride, and dibutylallyl, methylethylbenzyl,
ethylcyclohexylallyl and ethylcrotyldiethylaminoethyl dodecyl ammonium chloride.
There are also tertiary amines suitable for use which can be prepared by condensing a primary or secondary amine containing up to four basic nitrogen atoms and one aliphatic or alkylaromatic radical having eight to 18 and preferably eight to 14 aliphatic carbon atoms with a phenol or lower aliphatic aldehyde, preferably formaldehyde or acetaldehyde. The phenol employed in the condensation reaction may have in its molecule a plurality of sites capable of condensation, and these may be substituted with lower alkyl, alkoxy or benzyl radicals containing up to 4 carbon atoms. The phenol, alkyl, alkoxy and benzyl radicals may additionally be substituted with chlorine or bromine atoms and/or with nitro groups. Examples of such condensation products include, for instance, the following compounds: oxybenzyloctylamine, oxybenzyl dodecyldiethylenetriamine, (2-oxy-5-chloro-6-methylbenzyl)- dodecyldiethylenetriamine, (2-oxy-5-methylbenzyl)-octyldiethyl-enetriamine, (2-oxy-5-chloro-4,fi-dimethylbenzyl)-octyldiethylene-triamine, (tris-oxybenzyl )-dodecyltn'ethylenetriamine, o,o-bis-(tetradecylaminomethyl)-phenol, (octyl-diethylenetriaminomethyl)-p-cresol, o,o-bis-(dodecyldiethylenetriaminomethyl)-p-chloro-m-cresol, 7 mmbis(dodecyldiethylenetriarninomethyl)-p-oxybenzoic acid, 2,2-bis-p-oxy-m,m-di-(dodecyldiethylenetriaminomethyl)- phenolpropane, o,o-bis-(dodecyldiethylenetriaminomethyl)- p-nitrophenol, o,o-bis-(dodecylpropylenediaminomethyl)-pchloro-m,m-dimethylphenol, etc. The aforesaid tertiary amine compounds have a weakly acid reacting hydroxyl group and thus represent an intermediate type between the purely cationic and the hybrid (zwitter)-ionic surfactants. 1
The hybrid or zwitter ionic surfactants which have achieved particular importance as antimicrobials include compounds of the aminocarboxylic acid, polyaminocarboxylic acid and betaine type. i
Illustrative of the aminocarboxylic and polyaminocarboxylic acid antimicrobial agents are compounds having the following structural formula:
wherein R, represents an alkyl or alkylaryl radical of high molecular weight, preferably such a hydrocarbon radical having six to 18 and most preferably eight to 14 aliphatic carbon atoms, R represents an ethylene or propylene radical, x 20 represents a whole number of from one to six and R represents an aliphatic-aromatic or aromatic bridge having one to six carbon atoms. The following compounds are illustrative of aminocarboxylic and polyaminocarboxylic compounds having the above-mentioned formula: dodecylaminopropy[glycine, tetradecylaminoethyl-B-alanine, dodecyl-di-(aminoethyl)-glycine, dodecylaminoisopropylaminomethylsalicyclic acid, hexadecyl-tri-(aminoethyl)-B-aminobutyric acid, dodecylbenzylaminopropyl-B-alanine, octylphenoxyethyl-di- (aminoethyl)-glycine, dodecylaminoethylphenylalanine, dodecylaminoethylaminobenzoic acid, etc.
The radical R can also be interrupted by an ether oxygen atom, as is the case, for example, in the following compounds: dodecyloxypropylaminopropionic acid, lauryl-l,3-oxypropyl- B-aminobutyric acid, C, -alkyloxyethylaminoacetic acid, dodecyll ,2-0xypropylaminomethylsalicylic acid, octylphenoxyethylaminobenzoic acid.
The compounds that can be used according to the invention furthermore include carboxybetaines of the formula:
I which can be used both in the betaine form, i.e., in the form of inner salts, and in the form of acidic or basic salts. R has the same meaning as in the preceding formula, R represents an ethylene or propylene group, and R and R represent aliphatic radicals of low molecular weight, R represents an aliphatic bridge of low molecular weight, X an ether oxygen atom or the CONH group. Examples of such carboxybetaine compounds are lauryl-l,3-amidopropyldimethylaminoacetic acid, lauryloxyethyl-di-(hydroxyethyl)- aminoacetic acid, etc.
If the posttreatment agents according to the invention are in the form of solid products, they advantageously have the following composition:
70-5%, preferably 30-10%, by weight, textile softeners 3095%, preferably 70-90%, by weight, solid carrier substance 0-20%, preferably 1l5%, by weight, optical brighteners, most preferably a quantity amounting to from 5 to 25% of the quantity of the textile softener used.
030%, preferably l-l5%, by weight, surface active dispersing or emulsifying agents, although the quantity thereof must always be less than the quantity of the textile softener, preferably no more than 50%, and most preferably 5 to 25% of the quantity of the textile softener. 70
02%, preferably 01-10%, by weight, emulsion stabilizers or thickening agents, the quantity, however, not exceeding an amount whereby a 10% aqueous solution or dispersion of the entire solid preparation will still be a free-flowing liquid.
And, if desired,
05-20%, preferably 120%, by weight, of the above-named antimicrobial agents; wherein if these agents are antimicrobial, zwitter-ionic surfactants, their quantity is always to be smaller than the quantity of textile softener, amounting preferably to no more than 50%, and most preferably to 5 to 25%, of the quantity of the textile softener.
If the post-treatment agents according to the invention are in the form of liquid preparations, they advantageously have the following composition:
2-30%, preferably 515%, by weight, textile softeners 0-50%, preferably 5-30% by weight, solid water-soluble hydrotropic substance and/or water-soluble organic solvent.
0-l0%, preferably 0-5%, by weight, surface active emulsifying or dispersing agent, this quantity always to be smaller than the quantity of the textile softener, and preferably amounting to no more than 50%, and most preferably to 5 to 25%, by weight, of the quantity thereof.
010%, preferably l8%, by weight, optical brighteners, most preferably a quantity as to amount to 5 to 25% of the quantity of the textile softener.
020%, preferably 01-10%, by weight, water-soluble emulsion stabilizer or thickening agent, but not to exceed an amount whereby the preparation is no longer an easyflowing liquid.
and, if desired:
05-30%, preferably 120%, by weight, of the above-named antimicrobial agents; and if they are antimicrobial zwitter-ionic surfactants, their quantity is always to be less than the quantity of the textile softener, preferably no more than 50% and most preferably to 5 to 25% of the quantity thereof.
Remainder water and/or water-soluble organic solvent.
To illustrate the marfner in which the invention may be carried out, the following Examples are given. It is to be understood, however, that the Examples showing products of the invention are for the purpose of illustration and the invention is not to be regarded as limited to any of the specific materials or conditions recited therein.
The Examples described a number of liquid laundry posttreatment agents. The polyglycerylamide derivative has three CH CHOHCH O radicals per molecule. The ethoxylated dimethyl polysiloxane incorporated into a number of preparations as an emulsifier is marketed by Wackerchemie GmbH, Munich, under the trade name DC 202.
All percentages are percentages by weight.
EXAMPLE 1 5% glucamide R =C, C, mixture of tallow fatty acid, average approxi- 30% ethylene glycol monoethyl ether 2% nonylphenol plus 9.5 ethoxyl 5 8% water EXAMPLE 2 5% glucamide R,=C, H R C H 5% dihydroxypropylamide as described in Example 1 30% ethylglycol monoethylether 2% nonylphenol plus 9.5 ethoxyl 5 8% water EXAMPLE 3 10% polyglyceryl amide R,=C, C,,, mixture of coconut fatty acid, average approximately C R =C, -C mixture of tallow fatty acid, average approximately C Combined total approximately 29 carbon atoms. ethylene glycol monoethylether 4% nonylphenol plus 9.5 ethoxyl 66% water EXAMPLE 4 58% water EXAMPLE 5 8% glucamide R, H OC H Total 34 carbon atoms 2% dihydroxypropylamide R,=C, C mixture of tallow fatty acid, average approximately C R =C,,-C mixture of coconut fatty acid, average ap proximately C Total approximately 30 carbon atoms 90% isopropanol.
EXAMPLE 6 R1: l2 R2 n as Total 29 arbon atoms 5% dihydroxypropylamide as described in Example 5 90% isopropanol.
5% glucamide EXAMPLE 7 5% glucamide as described in Example 1 5% dihydroxypropylamide as described in ethylene glycol monoethyl ether l0% tartaric acid 2% alkyl phenol plus 9.5 ethoxyl 48% water Example 8 EXAMPLE 10 10% dihydroxypropylamide as described in Example 4 30% ethylene glycol monomethyl ether 2% ethoxylated dimethyl polysiloxane 10% tartaric acid 48% water EXAMPLE 1 1 l0% polyglycerylamide as described in Example 3 30% ethylene glycol monoethyl ether 2% ethoxylated dimethyl polysiloxane l0% gluconic acid 48% water EXAMPLE l2 l0% dihydroxypropylamide as described in Example 7 30% isopropanol 2% nonylphenol plus 9.5 ethoxyl 10% amidosulfonic acid 48% water EXAMPLE l3 l0% dihydroxypropylamide R, C H- R C H;
Total 29 carbon atoms 40% ethylene glycol monoethyl ether 2% nonylphenol plus 9.5 ethoxyl 1% brightening agent as described on page 26 47% water EXAMPLE l4 5% glucamide as described in Example 5 5% dihydroxypropylamide as described in Example 8 2% N-dodecyl-N-benzyl-N-N,N-dimethylammonium chloride 88% isopropanol EXAMPLE 15 5% glucamide as described in Example 8 5% dihydroxypropylamide as described in Example 8 30% ethylene glycol monoethyl ether 2% nonylphenol plus 9.5 ethoxyl 2% N-dodecyl-N-benzyl-N-N,N-dimethylammonium chloride 10% citric acid 46% water The preparations corresponding to Examples 1 to 4, 8 to 13, and 15, are in the form of dispersions, and the preparations according to Examples 5 to 7 and 14 are in the form of clear solutions.
A number of experiments were carried out using ordinary cotton fabrics or cotton terry cloth in which the fabric samples were eashed in a drum-type washing machine using a conventional commercially available controlled-suds detergent and temperatures of up to 95 C. In the final rinse, one of the preparations described in the Examples was added in a quantity sufficient to provide a concentration of 0.3 grams of the textile softeners per liter of washing medium. The dried cotton fabrics all had a soft feel and excellent absorbency.
We claim:
1. A composition for softening laundered textiles consisting essentially of Rr-IIT-C -R2 and I Ri-NCO-R2 (IT) CHg-(CHOH) ,,CH OH wherein R, is
1. alkyl of 10 to 22 carbon atoms, or I 2. alkyl of 10 to 22 carbon atoms with an ether oxygen linkage in the vicinity of the nitrogen atom, R is alkyl of seven to 21 carbon atoms, R +R have 23 to 39 carbon atoms,
Z is (1) H2-CHOH-CH2OH 2 CH2OIPIIJJHCH2OH, or
3. an ether of l) or (2) with 1 to l4-additional glyceryl radicals, and n is 3 or 4, (11) being present to the extent of about 50 to 90 percent by weight of(l) and (ll). 2. A composition according to claim 1, wherein (I) and (11) constitute about 2-30 weight percent, said composition in- 3. A composition according to claim 2, wherein (I) and (II) constitute about -15 weight percent, wherein R, has 12 to 20 carbon atoms, wherein R has I l to 19 carbon atoms, and wherein R,+R have a total of 27 to 35 carbon atoms.
4. A composition according to claim 1, wherein (I) and (ii) constitute about 5-70 weight percent, and about 30-95 weight percent of solid carrier substance selected from the group consisting of salts of sulfuric acid, phosphoric acids, or aliphatic carboxylic acids containing up to about carbon atoms, urea, acetamide and polyethylene glycols.
5. A composition according to claim 1, including 0.5-20 weight percent of a heavy metal-free, nonoxidizing water-soluble antimicrobial agent.
6. A method for treating a textile-fabric article comprising laundering said article, and thereafter rinsing said article with water containing dissolved therein in the range of 0.05 to 2 grams per liter of a compound of the formula wherein: R, is
1. alkyl of 10 to 22 carbon atoms, or 2. alkyl of 10 to 22 carbon atoms with an ether oxygen linkage between either the 2 and 3 or 3 and 4 carbon atoms from the nitrogen atom, R is alkyl of seven to 21 carbon atoms, R,+R have 23 to 39 carbons atoms, and
Z iS
IIzCC1IOlI-Cliz0l[ ouzoi-r-orr-o molt, or
3. an ether of l or (2) with one to 14 additional glyceryl radicals; 7. A method according to claim 6 wherein the rinse water also has dissolved therein a compound of the formula R1-N C 0-Rz omorromn-cmon wherein R,, R have the same meanings as in claim 6 and n is 3 or 4, the compound (II) being present to the extent of about 50 to by weight of(I) and (ii).
8. A method according to claim 7, wherein R, has 12 to 20 carbon atoms, wherein R has 11 to 19 carbon atoms, and wherein R,+R have a total of 27 to 35 carbon atoms.
Claims (10)
- 2. alkyl of 10 to 22 carbon atoms with an ether oxygen linkage in the vicinity of the nitrogen atom, R2 is alkyl of seven to 21 carbon atoms, R1+R2 have 23 to 39 carbon atoms,
- 2. A composition according to claim 1, wherein (I) and (II) constitute about 2-30 weight percent, said composition including a solvent selected from the group consisting of water, a water-soluble organic solvent and a mixture of water and water-soluble organic solvent, said water-soluble organic solvent being selected from the group consisting of unsubstituted aliphatic monohydric alcohols of one to four carbon atoms, ether alcohols formed by the reaction of said aliphatic alcohols with a glycol selected from the group consisting of ethylene glycol, propylene glycol, butylene glycol and diethylene glycol, water-soluble lower ketones and monoethers and diethers formed by reacting said unsubstituted aliphatic monohydric alcohols with glycerine.
- 2. alkyl of 10 to 22 carbon atoms with an ether oxygen linkage between either the 2 and 3 or 3 and 4 carbon atoms from the nitrogen atom, R2 is alkyl of seven to 21 carbon atoms, R1+R2 have 23 to 39 carbons atoms, and
- 3. an ether of (1) or (2) with one to 14 additional glyceryl radicals. 7. A method according to claim 6 wherein the rinse water also has dissolved therein a compound of the formula wherein R1, R2 have the same meanings as in claim 6 and n is 3 or 4, the compound (II) being present to the extent of about 50 to 90% by weight of (I) and (II).
- 3. an ether of (1) or (2) with 1 to 14 additional glyceryl radicals, and n is 3 or 4, (II) being present to the extent of about 50 to 90 percent by weight of (I) and (II).
- 3. A composition according to claim 2, wherein (I) and (II) constitute about 5-15 weight percent, wherein R1 has 12 to 20 carbon atoms, wherein R2 has 11 to 19 carbon atoms, and wherein R1+R2 have a total of 27 to 35 carbon atoms.
- 4. A composition according to claim 1, wherein (I) and (II) constitute about 5-70 weight percent, and about 30-95 weight percent of solid carrier substance selected from the group consisting of salts of sulfuric acid, phosphoric acids, or aliphatic carboxylic acids containing up to about 10 carbon atoms, urea, acetamide and polyethylene glycols.
- 5. A composition according to claim 1, including 0.5-20 weight percent of a heavy metal-free, nonoxidizing water-soluble antimicrobial agent.
- 6. A method for treating a textile-fabric article comprising laundering said article, and thereafter rinsing said article with water containing dissolved therein in the range of 0.05 to 2 grams per liter of a compound of the formula wherein: R1 is
- 8. A method according to claim 7, wherein R1 has 12 to 20 carbon atoms, wherein R2 has 11 to 19 carbon atoms, and wherein R1+R2 have a total of 27 to 35 carbon atoms.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEH0063600 | 1967-08-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3644204A true US3644204A (en) | 1972-02-22 |
Family
ID=7162379
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US743610A Expired - Lifetime US3644204A (en) | 1967-08-14 | 1968-07-10 | Agent for the post-treatment of washed laundry |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3644204A (en) |
| BE (1) | BE719461A (en) |
| DE (1) | DE1619086A1 (en) |
| ES (1) | ES357208A1 (en) |
| FR (1) | FR1586913A (en) |
| GB (1) | GB1244505A (en) |
| NL (1) | NL6810097A (en) |
| SE (1) | SE333131B (en) |
Cited By (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3764531A (en) * | 1966-08-01 | 1973-10-09 | Henkel & Cie Gmbh | Antimicrobial and laundry softening compositions |
| US3904359A (en) * | 1972-09-07 | 1975-09-09 | Colgate Palmolive Co | Post-wash fabric treating method |
| US3919091A (en) * | 1972-05-19 | 1975-11-11 | Henkel & Cie Gmbh | Fabric softening compositions containing quaternary allophanoylmethylammonium compounds |
| US3997450A (en) * | 1972-04-10 | 1976-12-14 | Fiber Industries, Inc. | Synthetic fibers of enhanced processability |
| US3997453A (en) * | 1974-02-11 | 1976-12-14 | Colgate-Palmolive Company | Softener dispersion |
| US4051299A (en) * | 1974-03-15 | 1977-09-27 | Fiber Industries Inc. | Synthetic fibers of enhanced processability |
| US4115289A (en) * | 1973-08-02 | 1978-09-19 | A. B. Dick Company | Dry powdered or liquid developer compositions |
| US4134838A (en) * | 1977-02-15 | 1979-01-16 | Lever Brothers Company | Fabric conditioning product |
| TR22593A (en) * | 1987-05-18 | 1987-12-15 | Ahmet Ecevit | SELF STORED UECGEN PRISM TYPE DUEZ GUENES COLLECTOR |
| US4895667A (en) * | 1988-05-24 | 1990-01-23 | The Dial Corporation | Fabric treating compositions |
| US5009814A (en) * | 1987-04-08 | 1991-04-23 | Huls Aktiengesellschaft | Use of n-polyhydroxyalkyl fatty acid amides as thickening agents for liquid aqueous surfactant systems |
| US5223179A (en) * | 1992-03-26 | 1993-06-29 | The Procter & Gamble Company | Cleaning compositions with glycerol amides |
| US5283009A (en) * | 1992-03-10 | 1994-02-01 | The Procter & Gamble Co. | Process for preparing polyhydroxy fatty acid amide compositions |
| US5476671A (en) * | 1993-12-17 | 1995-12-19 | Chesebrough-Pond's Usa Co., Division Of Conopco, Inc. | Synthetic ceramides and their use in cosmetic compostions |
| US5538648A (en) * | 1991-03-20 | 1996-07-23 | Sandoz Ltd. | Process for pretreating a textile material |
| US6346217B1 (en) * | 1999-06-02 | 2002-02-12 | Water Whole International, Inc. | Composition and method for cleaning drink water tanks |
| US20030060390A1 (en) * | 2001-03-07 | 2003-03-27 | The Procter & Gamble Company | Rinse-added fabric conditioning composition for use where residual detergent is present |
| US7026278B2 (en) | 2000-06-22 | 2006-04-11 | The Procter & Gamble Company | Rinse-added fabric treatment composition, kit containing such, and method of use therefor |
| US20130184197A1 (en) * | 2008-01-04 | 2013-07-18 | Lg Household & Health Care Ltd | Functional sheet for delivering laundry actives in low-temperature water |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL79365A0 (en) * | 1985-07-12 | 1986-10-31 | Cogent Ltd | Methods and products for treating and colouring materials |
| DE69417564D1 (en) * | 1993-09-09 | 1999-05-06 | Procter & Gamble | GRANULAR CLEANER CONTAINING AN N-ALKOXYPOLYHYDROXY FATTY ACID AMIDIDE |
| EP0919608A1 (en) * | 1997-11-25 | 1999-06-02 | The Procter & Gamble Company | Use of a polyhydroxyfatty acid amide compound as a softening compound |
| CN114423851A (en) * | 2019-09-19 | 2022-04-29 | 联合利华知识产权控股有限公司 | Detergent composition |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2002613A (en) * | 1932-02-29 | 1935-05-28 | Gen Aniline Works Inc | Reaction product of an organic acid amide and an alkylene oxide |
| US2334852A (en) * | 1940-07-16 | 1943-11-23 | Alrose Chemical Company | Textile wetting and softening bath |
| US3122502A (en) * | 1960-10-10 | 1964-02-25 | Milton M Waldman | Stabilized germicidal textile softeners |
| US3349033A (en) * | 1964-08-26 | 1967-10-24 | Millmaster Onyx Corp | Stable microbiologically active laundry softener |
| US3356526A (en) * | 1964-05-13 | 1967-12-05 | Armour & Co | Method of preparing water-dispersible softener compositions and products produced thereby |
| US3424680A (en) * | 1965-08-05 | 1969-01-28 | American Cyanamid Co | Soil retardant compositions and textile materials |
| US3454494A (en) * | 1965-08-03 | 1969-07-08 | Standard Chem Products Inc | Textile softener compositions |
-
1967
- 1967-08-14 DE DE19671619086 patent/DE1619086A1/en active Pending
-
1968
- 1968-04-30 SE SE5883/68A patent/SE333131B/en unknown
- 1968-07-10 US US743610A patent/US3644204A/en not_active Expired - Lifetime
- 1968-07-17 NL NL6810097A patent/NL6810097A/xx unknown
- 1968-08-13 ES ES357208A patent/ES357208A1/en not_active Expired
- 1968-08-13 GB GB38589/68A patent/GB1244505A/en not_active Expired
- 1968-08-14 FR FR1586913D patent/FR1586913A/fr not_active Expired
- 1968-08-14 BE BE719461D patent/BE719461A/xx unknown
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2002613A (en) * | 1932-02-29 | 1935-05-28 | Gen Aniline Works Inc | Reaction product of an organic acid amide and an alkylene oxide |
| US2334852A (en) * | 1940-07-16 | 1943-11-23 | Alrose Chemical Company | Textile wetting and softening bath |
| US3122502A (en) * | 1960-10-10 | 1964-02-25 | Milton M Waldman | Stabilized germicidal textile softeners |
| US3356526A (en) * | 1964-05-13 | 1967-12-05 | Armour & Co | Method of preparing water-dispersible softener compositions and products produced thereby |
| US3349033A (en) * | 1964-08-26 | 1967-10-24 | Millmaster Onyx Corp | Stable microbiologically active laundry softener |
| US3454494A (en) * | 1965-08-03 | 1969-07-08 | Standard Chem Products Inc | Textile softener compositions |
| US3424680A (en) * | 1965-08-05 | 1969-01-28 | American Cyanamid Co | Soil retardant compositions and textile materials |
Cited By (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3764531A (en) * | 1966-08-01 | 1973-10-09 | Henkel & Cie Gmbh | Antimicrobial and laundry softening compositions |
| US3997450A (en) * | 1972-04-10 | 1976-12-14 | Fiber Industries, Inc. | Synthetic fibers of enhanced processability |
| US3919091A (en) * | 1972-05-19 | 1975-11-11 | Henkel & Cie Gmbh | Fabric softening compositions containing quaternary allophanoylmethylammonium compounds |
| US3904359A (en) * | 1972-09-07 | 1975-09-09 | Colgate Palmolive Co | Post-wash fabric treating method |
| US3954630A (en) * | 1972-09-07 | 1976-05-04 | Colgate-Palmolive Company | Post-wash fabric treating composition and method |
| US4115289A (en) * | 1973-08-02 | 1978-09-19 | A. B. Dick Company | Dry powdered or liquid developer compositions |
| US3997453A (en) * | 1974-02-11 | 1976-12-14 | Colgate-Palmolive Company | Softener dispersion |
| US4051299A (en) * | 1974-03-15 | 1977-09-27 | Fiber Industries Inc. | Synthetic fibers of enhanced processability |
| US4134838A (en) * | 1977-02-15 | 1979-01-16 | Lever Brothers Company | Fabric conditioning product |
| US5009814A (en) * | 1987-04-08 | 1991-04-23 | Huls Aktiengesellschaft | Use of n-polyhydroxyalkyl fatty acid amides as thickening agents for liquid aqueous surfactant systems |
| TR22593A (en) * | 1987-05-18 | 1987-12-15 | Ahmet Ecevit | SELF STORED UECGEN PRISM TYPE DUEZ GUENES COLLECTOR |
| US4895667A (en) * | 1988-05-24 | 1990-01-23 | The Dial Corporation | Fabric treating compositions |
| US5538648A (en) * | 1991-03-20 | 1996-07-23 | Sandoz Ltd. | Process for pretreating a textile material |
| US5283009A (en) * | 1992-03-10 | 1994-02-01 | The Procter & Gamble Co. | Process for preparing polyhydroxy fatty acid amide compositions |
| US5223179A (en) * | 1992-03-26 | 1993-06-29 | The Procter & Gamble Company | Cleaning compositions with glycerol amides |
| WO1993019145A1 (en) * | 1992-03-26 | 1993-09-30 | The Procter & Gamble Company | Cleaning compositions with glycerol amides |
| US5476671A (en) * | 1993-12-17 | 1995-12-19 | Chesebrough-Pond's Usa Co., Division Of Conopco, Inc. | Synthetic ceramides and their use in cosmetic compostions |
| US6346217B1 (en) * | 1999-06-02 | 2002-02-12 | Water Whole International, Inc. | Composition and method for cleaning drink water tanks |
| US7026278B2 (en) | 2000-06-22 | 2006-04-11 | The Procter & Gamble Company | Rinse-added fabric treatment composition, kit containing such, and method of use therefor |
| US20060075576A1 (en) * | 2000-06-22 | 2006-04-13 | Price Kenneth N | Rinse-added fabric treatment composition, kit containing such, and method of use therefor |
| US20030060390A1 (en) * | 2001-03-07 | 2003-03-27 | The Procter & Gamble Company | Rinse-added fabric conditioning composition for use where residual detergent is present |
| US20060019867A1 (en) * | 2001-03-07 | 2006-01-26 | Demeyere Hugo J M | Rinse-added fabric conditioning composition for use where residual detergent is present |
| US20060030516A1 (en) * | 2001-03-07 | 2006-02-09 | Demeyere Hugo J M | Rinse-added fabric conditioning composition for use where residual detergent is present |
| US20130184197A1 (en) * | 2008-01-04 | 2013-07-18 | Lg Household & Health Care Ltd | Functional sheet for delivering laundry actives in low-temperature water |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1586913A (en) | 1970-03-06 |
| SE333131B (en) | 1971-03-08 |
| GB1244505A (en) | 1971-09-02 |
| NL6810097A (en) | 1969-02-18 |
| ES357208A1 (en) | 1970-05-01 |
| DE1619086A1 (en) | 1969-08-21 |
| BE719461A (en) | 1969-02-14 |
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