US2427242A - Textile softening composition - Google Patents
Textile softening composition Download PDFInfo
- Publication number
- US2427242A US2427242A US593758A US59375845A US2427242A US 2427242 A US2427242 A US 2427242A US 593758 A US593758 A US 593758A US 59375845 A US59375845 A US 59375845A US 2427242 A US2427242 A US 2427242A
- Authority
- US
- United States
- Prior art keywords
- aliphatic
- weight
- carbon atoms
- water
- amine
- 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
- 239000000203 mixture Substances 0.000 title description 79
- 239000004753 textile Substances 0.000 title description 24
- 125000004432 carbon atom Chemical group C* 0.000 description 32
- 150000003839 salts Chemical class 0.000 description 17
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 15
- 125000000129 anionic group Chemical group 0.000 description 14
- 239000004094 surface-active agent Substances 0.000 description 14
- 150000001412 amines Chemical class 0.000 description 13
- 150000002357 guanidines Chemical class 0.000 description 13
- 229910052751 metal Inorganic materials 0.000 description 13
- 239000002184 metal Substances 0.000 description 13
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 11
- 125000002947 alkylene group Chemical group 0.000 description 11
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 10
- -1 ethylene, propylene Chemical group 0.000 description 10
- 229920005989 resin Polymers 0.000 description 10
- 239000011347 resin Substances 0.000 description 10
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 8
- 239000004744 fabric Substances 0.000 description 8
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical class NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 7
- 239000007859 condensation product Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 6
- 239000002752 cationic softener Substances 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 5
- DIZPMCHEQGEION-UHFFFAOYSA-H aluminium sulfate (anhydrous) Chemical compound [Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O DIZPMCHEQGEION-UHFFFAOYSA-H 0.000 description 5
- 150000001408 amides Chemical class 0.000 description 5
- 239000001569 carbon dioxide Substances 0.000 description 5
- 229910002092 carbon dioxide Inorganic materials 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 4
- MBHRHUJRKGNOKX-UHFFFAOYSA-N [(4,6-diamino-1,3,5-triazin-2-yl)amino]methanol Chemical class NC1=NC(N)=NC(NCO)=N1 MBHRHUJRKGNOKX-UHFFFAOYSA-N 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 239000004202 carbamide Substances 0.000 description 4
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 4
- 125000002091 cationic group Chemical group 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 238000009988 textile finishing Methods 0.000 description 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 150000001715 carbamic acids Chemical class 0.000 description 3
- MLYBIJPLWRODND-UHFFFAOYSA-L disodium;4-amino-4-oxo-2-sulfobutanoate Chemical compound [Na+].[Na+].NC(=O)CC(C([O-])=O)S(O)(=O)=O.NC(=O)CC(C([O-])=O)S(O)(=O)=O MLYBIJPLWRODND-UHFFFAOYSA-L 0.000 description 3
- ZRALSGWEFCBTJO-UHFFFAOYSA-O guanidinium Chemical class NC(N)=[NH2+] ZRALSGWEFCBTJO-UHFFFAOYSA-O 0.000 description 3
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 3
- 238000004900 laundering Methods 0.000 description 3
- BXXLBMBLLVIOKO-UHFFFAOYSA-N octadecylcarbamic acid Chemical compound CCCCCCCCCCCCCCCCCCNC(O)=O BXXLBMBLLVIOKO-UHFFFAOYSA-N 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 229920001187 thermosetting polymer Polymers 0.000 description 3
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical class C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 3
- FJLUATLTXUNBOT-UHFFFAOYSA-N 1-Hexadecylamine Chemical compound CCCCCCCCCCCCCCCCN FJLUATLTXUNBOT-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- 229920000297 Rayon Polymers 0.000 description 2
- 239000004902 Softening Agent Substances 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical compound OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 2
- 150000003973 alkyl amines Chemical class 0.000 description 2
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- LJZDFZSLLYVEAM-UHFFFAOYSA-N carbamic acid;guanidine Chemical class NC(N)=N.NC(O)=O LJZDFZSLLYVEAM-UHFFFAOYSA-N 0.000 description 2
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 2
- 229910000388 diammonium phosphate Inorganic materials 0.000 description 2
- 235000019838 diammonium phosphate Nutrition 0.000 description 2
- 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 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 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 2
- 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 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000002964 rayon Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 210000002268 wool Anatomy 0.000 description 2
- QIVUCLWGARAQIO-OLIXTKCUSA-N (3s)-n-[(3s,5s,6r)-6-methyl-2-oxo-1-(2,2,2-trifluoroethyl)-5-(2,3,6-trifluorophenyl)piperidin-3-yl]-2-oxospiro[1h-pyrrolo[2,3-b]pyridine-3,6'-5,7-dihydrocyclopenta[b]pyridine]-3'-carboxamide Chemical compound C1([C@H]2[C@H](N(C(=O)[C@@H](NC(=O)C=3C=C4C[C@]5(CC4=NC=3)C3=CC=CN=C3NC5=O)C2)CC(F)(F)F)C)=C(F)C=CC(F)=C1F QIVUCLWGARAQIO-OLIXTKCUSA-N 0.000 description 1
- GLKRSFJCYTXIOF-UHFFFAOYSA-N 2-octadecylguanidine Chemical compound CCCCCCCCCCCCCCCCCCN=C(N)N GLKRSFJCYTXIOF-UHFFFAOYSA-N 0.000 description 1
- NETFLLQHBBVMCB-UHFFFAOYSA-N 4-amino-1-octadecoxy-1,4-dioxobutane-2-sulfonic acid Chemical class CCCCCCCCCCCCCCCCCCOC(=O)C(S(O)(=O)=O)CC(N)=O NETFLLQHBBVMCB-UHFFFAOYSA-N 0.000 description 1
- DUFCMRCMPHIFTR-UHFFFAOYSA-N 5-(dimethylsulfamoyl)-2-methylfuran-3-carboxylic acid Chemical compound CN(C)S(=O)(=O)C1=CC(C(O)=O)=C(C)O1 DUFCMRCMPHIFTR-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 241000543381 Cliftonia monophylla Species 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 241001527806 Iti Species 0.000 description 1
- VGGLHLAESQEWCR-UHFFFAOYSA-N N-(hydroxymethyl)urea Chemical compound NC(=O)NCO VGGLHLAESQEWCR-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- HVWGGPRWKSHASF-UHFFFAOYSA-N Sulfuric acid, monooctadecyl ester Chemical compound CCCCCCCCCCCCCCCCCCOS(O)(=O)=O HVWGGPRWKSHASF-UHFFFAOYSA-N 0.000 description 1
- PLZVEHJLHYMBBY-UHFFFAOYSA-N Tetradecylamine Chemical compound CCCCCCCCCCCCCCN PLZVEHJLHYMBBY-UHFFFAOYSA-N 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical class C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000019658 bitter taste Nutrition 0.000 description 1
- 230000000740 bleeding effect Effects 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- SXPWTBGAZSPLHA-UHFFFAOYSA-M cetalkonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 SXPWTBGAZSPLHA-UHFFFAOYSA-M 0.000 description 1
- 229960000228 cetalkonium chloride Drugs 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000005562 fading Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000004312 hexamethylene tetramine Substances 0.000 description 1
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 229960004011 methenamine Drugs 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-N o-dicarboxybenzene Natural products OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- QUBQYFYWUJJAAK-UHFFFAOYSA-N oxymethurea Chemical class OCNC(=O)NCO QUBQYFYWUJJAAK-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003139 primary aliphatic amines Chemical class 0.000 description 1
- 150000003141 primary amines Chemical class 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
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- DIORMHZUUKOISG-UHFFFAOYSA-N sulfoformic acid Chemical class OC(=O)S(O)(=O)=O DIORMHZUUKOISG-UHFFFAOYSA-N 0.000 description 1
- 235000019640 taste Nutrition 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 229960001763 zinc sulfate Drugs 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 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
- D06M13/432—Urea, thiourea or derivatives thereof, e.g. biurets; Urea-inclusion compounds; Dicyanamides; Carbodiimides; Guanidines, e.g. dicyandiamides
Definitions
- Patented .9, 1947 UNITED STATES PATENT OFFICE.
- softening materials densation with alkylene oxides of 2-4 carbon atoms such as ethylene, propylene or butylene' oxide, and in this condition they are shown to be good cationic softe n agents for textiles.
- Our present invention is based on the discovery that the addition of anion-active surface-active agents having singlelong aliphatic chain of 12 or more and preferably 16-18 carbon atoms to certain of the compositions described in the Thurston et al. application will result in textile finishing compositions of greatly improved perof the class of oils, waxes and the like have been proposed for improving the softness of hand of textiles, there is still a demand for softeners of improved permanency and laundry-resistance. Many of the compomtions now sold on the market will produce atemporary softening eifect, but the textiles soon become limp and raggy after they have been laundered several times. This is true even ofthe so-called cationic softeners, which are supposed to combinepermanently with textiles through the action of an opposite electrical charge, but many of which lose softening power almost completely by repeated launderings.
- our invention consists in the provision of a mixture-containing a major quantity of the reaction product of an alkylene oxide v of 2-4 carbon atoms with mixed N-aliphatic carbamic acid salts of aliphatic-substituted guanidines and amines in which all the aliphatic radicals contain 12 or more carbon atoms together with a smaller quantity of an anionic surfaceactiveagent containing a single long aliphatic
- the invention will appear from the following deand w. N. Oldham, Serial No.
- the aliphatic radical may be either saturated or unsaturated, for we have found that even a relatively high degree of unsaturation does not cause the stabilizing or antioxidant properties of the guanidine radical.
- This fact permits us to employ tes prepared from mixtures of higher aliphatic amines, such as are now available on the market at low cost and in large quantitles.
- One such mixture which we have used with advantage contains about 20-30% of hexadecyl amine and about 'I0-80% of a mixture of saturated and unsaturated amines of 18 carbon atoms. 1
- the reaction with cyanamide is so controlled that about -70% of the amines are con-' I in which R is a saturated or unsaturated *alif phatic radical of 12 or more carboniatomscorresponding to the amine used, while the remainder is present in the form of an amine salt 'of-anllsubstituted carbamic acid of the formula Rmnocormn in which ⁇ ! is as defined above. Under these con ditions the reaction product contains about 15-25 moi percent of unreacted amine, about 50. mol.
- the quantities of alkylene oxide condensed with .the mixture of carbamic acid salts should be limited to'avoid the formation of a product of excessive water-solubility, as otherwise the laun- 'dry-resistance of the finished composition will be Thus, for example; about 5-7 mols of ethylene olides'hoilld be condensed with mixinto guanidinium carbamates oftheforv t re in' which the aliphatic radicals. "contain- 16-18'carbonatoms, while quantities of 3-6 mols should be'used with guanidines of lower molecular weight.
- R is a saturated or unsaturated aliphatic radical of 12 or more carbon atoms, and preferably an unbranched aliphatic chain of 16-18 carbon atoms and Me is a salt-forming group such as sodium, ammonium, etc.
- R is a saturated or unsaturated aliphatic radical of 12 or more carbon atoms, and preferably an unbranched aliphatic chain of 16-18 carbon atoms and Me is a salt-forming group such as sodium, ammonium, etc.
- the hexadecyl and octadecyl sulfosuccinamates are preferred to the corresponding compounds of lower molecular weight because of their reduced water-solubility, and this is also true of the corresponding mono esters of sulfosuccinic acid.
- compositions of our invention can be applied to textiles in conjunction with thermosetting. resin finishes such as methylol melamines containing 13-6 methylol groups, di-
- methylolurea,-alky1ated methylol melamines such as tri, tetra, 1penta orhexamethylated methylol melamines or .withdimethylated dimethylol urea.
- compositions being those containing 5-7 mols of ethylene oxide for each molofan aliphatic amine of -16-l8 starting material.
- Any anionic surface-active agent containing a single long aliphatic radical'of 12 or more carbon atoms may be employed. Higher allryl sulfates carbon atoms used as resin finishes.
- the improved textile softening compositions of our invention are those. which contain a cationic softener consisting essentially of the condensation such as dodecyl, hexadecyl or octadecyl sulfate 1 or alkaryl sulfonates such as keryl benzene sulfonate may be used if desired.
- a cationic softener consisting essentially of the condensation such as dodecyl, hexadecyl or octadecyl sulfate 1 or alkaryl sulfonates such as keryl benzene sulfonate may be used if desired.
- These compounds have the forproduct of mixed aliphatic amine and aliphaticsubstituted guanidine salts oflN-aliphatic' carbamic acids in which the aliphatic radical contain 12-18 carbonatoms with 2-10 mols of an alkylene oxide of 2-4 carbon atoms, this cationic I softener being mixed with an'anionic surfaceerienh'anced by the sincelarser quantities I ay causefharshnessinHthetreated fabrics; jln 'some cases the presence of substantial -.qua n tities' of] these 1 inorganic salts atom are preferred, and in such mixtures optimum results are obtained with about 90-94% by weight of the cationic material and about 6-10% by weight of the anionic material.
- compositions may be used as such or in admixture with 0.1-4% of water-soluble polyvalent metal salts such as aluminum sulfate, and in the latter case we prefer to add a water-soluble amide such as urea, thiourea and the like in amounts .'of about 1-5 times the weight of the metal salt.
- compositions of our invention may be applied to textiles by any of the known or approved methods for the application of softening agents.
- Lam-g1 disodium sulfosuccinainate I The lauryl ,disodi'um sulfosuccinamate was then ground to a white powder easily soluble in water.
- Tetradecyl disodium sulfosuccinamate was prepared using the general procedure described in Example 1 employing a commercial product was a white powder havinga sweet odor and a bitter taste. It was fairly soluble in water,- a 10% solution being slightly turbid at C.
- Octadecyl disodium sulfosaccinamate Octadecyl disodium sulfosuccinamate was prepared by the method described in Example? using commercial octadecyl amine, C18I'I3'1NH2. The product was ayellow waxy powder having a mildly soapy odor and taste. It was dispersed in water to a paste.
- a composition containing about 25-35% of the amine in the form of a higher aliphatic-substituted guanidine is formed by reacting the following materials:
- octadecylamine 269 Isopropyl alcohol 135 Carbon dioxide 25 Water 17 Cyanamide (23.9% solution in water) by heating at 45 C. and then the solution is pumped into a reaction vessel along with the water. During 1.5 hours the carbon dioxide, in the form'of dry ice, is added in small portions, the temperature being kept below C. by cooling.
- the carbon dioxide reacts with the amine to form and octadecyl amine N-octadecylcarbamate in which about 50% of the amine has been converted into N-octadecylcarbamate and about 30% is converted into mono octadecyl guanidine which is combined with a part of the octadecyl-substb tuted carbamic acid in the form of a guanidinium salt. The remainder of the amine is combined with the rest of the N-octadecyl carbamic acid inthe form of a salt.
- the amine is dissolved in the isopropyl alcohol
- the guanidine carbamate mixture was condensed with alkylene oxide to form the condensation products used as cationic softeners in the compositions of the present invention.
- the vessel containing the reaction product was adapted for pressure and an ethylene oxide tank was attached so that ethylene oxide could be introduced above the surface of the reaction mixture.
- Ethylene oxide was slowly added at 60- 66 C. at a rate such that the internal pressure did not exceed 20 lbs. per square inch.
- Suflicient ethylene oxide was added during about 4 hours so that the final product contained not less than 5 nor more than 7 mols of the oxide for each mol of amine used as starting material. This amounted to 220-308 parts by weight of ethylene oxide.
- Methylated methylol melamine (80%) weight in lbs. 86.0
- the accelerator was a mixture of approximately four parts by weight of hexamethylene tetramine I and 30 parts of diammonium hydrogen phosphate.
- Softness as determined by hand After soaping as follows: After Cure 5 min min. 60 min Softener A Fair. Softener B Do. Softener C. Good. Softener D Fair. Softener E Good. Softener F Do. Softener G. Very good. Softener H Do. CommerclalSoftener Soft but raggy. Example 4 alone Baggy. Blank Harsh.
- the product was heated to 90 C. for a few minutes, then cooled to 70 C. and allowed to stand overnight. The next day it was concentrated by evaporation under a partial vacuum until a. sample showed a solids content of 80% upon distillation with benzene. The concentrated product.
- Me is a monovalent salt-forming radical and X is a member of the group of OR and NHR
- B. being an aliphaticradical Softener 6 min. 50 min. 1 hour 2 hours 1 Vo replenish full-..”
- a polyvalent metal salt such as aluminum sulfate in amounts of about 0.1-4% of the weight of the softener therefore assists materially in the retention of hand on soapini; but the addition of too much of the metal salt causes harshness.
- Example 4" The product of Example 4" is preferably one in which the commercial mixture of hexadecyland octadecylamines is used as a starting material.
- This composition decreases the bleeding of dyed fabrics and does not cause dye fading, it does not chalk or dust upon storage of the treated textiles and it can be applied along with thermosetting resin finishes from-the same bath of 12-18 carbon atoms, together with 0.1-4% of a water-soluble aluminum salt, based on the weight b of said mixture.
- a softening composition for textiles comprising a mixture of 90-94% by weight of the condensation product of 5-7 mols of ethylene oxide with a mixture of 50-70 mol percent of an aliphatic-substituted guanidinium N-aliphatic carbamate and 50-30 mol percent of an aliphatic amine N-aliphatic carbamate in which the aliwithout impairing the bath stability or the curing action of curing accelerators contained therein.
- a softening composition for textiles comprising a mixture of 90-94% by weight of the condensation product of 5-7 mols of ethylene oxide with a mixture of 50-70 mol percent of an allphatic-substituted guanidinium N-aliphatic carbamate and 50-30 mol percent of an aliphatic amine N-aliphatic carbamate in which the all-- phatic radicals contain 16-18 carbon atoms and 10-6% by weight of an anionic surface-active agent containing a single long aliphatic radical of 16-18 carbon atoms together with 0.1-4% of a water-soluble aluminum salt, based on the weight of said mixture.
- a softening composition for textiles comprising a mixture of 90-94% by weight of the condensation product of 5-7 mols of ethylene oxide with a mixture of 50-70 mol percent of an aliphatic-substituted guanidinium N-aliphatic carbamate and 50-30 mol percent of an aliphatic amine N-aliphatic carbamate'in which the allphatic radicals contain 16-18 carbon atoms and phatic radicals contain 16-18 carbon atoms and 10-6% by weight of an N-aliphatic disodium sulfosuccinamate in which the aliphatic radical contains 16-18 carbon atoms, together with 0.1- 4% of aluminum sulfate, based on the weight of said mixture, and urea in amounts about twice the weight of said aluminum sulfate.
- a softening composition for textiles comprising 58 to 96 parts by weight of the condensation product of a mixture of aliphatic amine and aliphatic-substituted guanidine salts of N-aliphatic carbamic acids in which the aliphatic radicals contain 12 to 18 carbon atoms with 2 to 10 mols of an alkylene oxide of 2 to 4 carbon atoms and 42 to 4 parts by weight of an anionic surfaceactive agent containing a single long aliphatic radical of 12 to 18 carbon atoms.
- a composition according to claim 4 in which the mixture of aliphatic amine and aliphaticsubstituted guanidine salts of N-aliphatic carbamic acids is condensed with 3 to 7 mols of ethylene oxide.
- composition according to claim 5 in which the anionic surface-active agent is a compoun of the formula in which Me is a monovalent salt-forming radical and x is a member of the group consisting of --OR and NHR, It being an aliphatic radical of 12-18 carbon atoms.
- composition according to claim 6 which also contains 0.1 to 4% of a water-soluble polyvalent metal salt, based on the weight of the mixture recited in claim 6.
- composition according to claim 7. which also contains a water-soluble amide in an amount of about 1 to 5 times the weight of said polyvalent metal salt.
- a composition according to claim 4 in which a mixture of aliphatic amine and aliphatic-substituted guanidine salts of N-aliphatic carbamic acids in which the aliphatic radicals contain 16-18 carbon atoms is condensed with 5-7 mols of ethylene oxide.
- a softening composition for textiles comprising 58 to 96 parts by weight of the condensa- 11 tion product of a mixture of 50-70 mol percent of an aliphatic-substituted-guanidimum N-aliphatic carbamate and 50-30 mol per cent of an aliphatic amine N-aliphatic carbamate in which the aliphatic radicals contain 12-18 carbon atoms in which Me is a monovalent salt-forming radical and X is a member 01 the group consisting of OR and -NHR, B. being an aliphatic radical or 12-18 carbon atoms.
- a composition according to claim 12 which also contains 0.1 to 4% of a water-soluble polyvalent metal salt, based on the weight of the mixture recited in claim 12.
- composition according to claim 13 which also contains a water-soluble amide in an amount of about 1 to 5 times the weight oi. said polyvalent metal salt.
- a composition according to. claim 10 in which a mixture of aliphatic amine and aliphaticsubstituted guanidine salts of N-aliphatic carbamic acids in which the aliphatic radicals contain 16-18 carbon atoms is condensed with 5-7 mols of ethylene oxide.
- a softening composition for textiles comprising -96% by weight of the condensation product or a mixture of aliphatic amine and allphatic-substituted guanidine salts of N-aliphatlc carbamic acids in which the aliphatic radicals contain 12-18 carbon atoms with 2-10 mols of an alkylene oxide of 2-4 carbon atoms and 204% by weight of an anionic surface-active agent containing a single aliphatic radical of 12-18 carbon atoms.
- composition according to claim 17 which also contains 0.1 to 4% of a water-soluble polyvalent metal salt based on the weight of the mixture recited in claim 6.
- composition according to claim 18 which also contains a water-soluble amide in an amount of about 1 to 5 times the weight of said polyvalent metal salt.
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Description
Patented .9, 1947 UNITED STATES PATENT OFFICE.
'rnx'rma some COMPOSITION Emil A. Vitalis, East Port Chester, and John E. Lynn, Old Greenwich, Conn, asaignors to American Cyanamid Company,
New York,
N. Y., a corporation of Maine No Drawing. Application May 14, 1945,
Serial No. 593,758
19 Claims. (CL 252-835) 1 This invention relates to the softening of textiles such as wool, cotton, rayon, and nylon cloth,
I into a water-soluble condition by further conand is directed more particularly to the prorics, threads, and fibers with the aid of these softening compositions as will hereinafter be described.
Although a wide variety of softening materials densation with alkylene oxides of 2-4 carbon atoms such as ethylene, propylene or butylene' oxide, and in this condition they are shown to be good cationic softe n agents for textiles.
Our present invention is based on the discovery that the addition of anion-active surface-active agents having singlelong aliphatic chain of 12 or more and preferably 16-18 carbon atoms to certain of the compositions described in the Thurston et al. application will result in textile finishing compositions of greatly improved perof the class of oils, waxes and the like have been proposed for improving the softness of hand of textiles, there is still a demand for softeners of improved permanency and laundry-resistance. Many of the compomtions now sold on the market will produce atemporary softening eifect, but the textiles soon become limp and raggy after they have been laundered several times. This is true even ofthe so-called cationic softeners, which are supposed to combinepermanently with textiles through the action of an opposite electrical charge, but many of which lose softening power almost completely by repeated launderings.
It is a principal object of the present invention to provide textile softening compositions which can be used either alone or iii conjunction with other finishing agents to produce finished textiles having a soft and elastic hand which is not removed by repeated launderings. "A still further object is the provision of textile finishing compositions in the form of water-dispersible pastes which are stable upon storage.
scription of preferred embodiments thereof.
In the copending application of J. T. Thurston manency and laundry-resistance. In its broader "aspects, therefore, our invention consists in the provision of a mixture-containing a major quantity of the reaction product of an alkylene oxide v of 2-4 carbon atoms with mixed N-aliphatic carbamic acid salts of aliphatic-substituted guanidines and amines in which all the aliphatic radicals contain 12 or more carbon atoms together with a smaller quantity of an anionic surfaceactiveagent containing a single long aliphatic Other objects of ,the invention will appear from the following deand w. N. Oldham, Serial No. 542,246, filed June 26, 1944, there is described a new class of compounds obtained by conden'sing the reaction products of carbon dioxide and higher primary aliphatic amines containing 12 or more carbon atoms with aqueous cyanamide solutions. ,The products of this reaction contain guanidinium salts of N-aliphatic substituted carbamic acids in radical of 12 or more carbon atoms.
We have found that the addition of an aqueous solution of an anionic surface-active agent containing a single long aliphatic radical to aqueous solutions of the above-described alkylene oxide 7 sistant condition by heating textiles impregnated therewith for short periods of time. These mixtures may be applied to the textiles alone or in conjunction with small quantities on the order of 0.14% of water-soluble polyvalent metal salts such as aluminum sulfate, zinc sulfate, zirconium acetate and the like. They may be applied as such or in conjunction with starch or resin finishes. In all cases, however, it will be found that a marked improvement in the permanency of the finish is obtained, as compared with the laundry- The aliphatic radical may be either saturated or unsaturated, for we have found that even a relatively high degree of unsaturation does not cause the stabilizing or antioxidant properties of the guanidine radical. This fact permits us to employ tes prepared from mixtures of higher aliphatic amines, such as are now available on the market at low cost and in large quantitles. One such mixture which we have used with advantage contains about 20-30% of hexadecyl amine and about 'I0-80% of a mixture of saturated and unsaturated amines of 18 carbon atoms. 1
We have found that optimum results are ob tained when only apart of the higher aliphatic es are converted into guanidine salts. Preferably the reaction with cyanamide is so controlled that about -70% of the amines are con-' I in which R is a saturated or unsaturated *alif phatic radical of 12 or more carboniatomscorresponding to the amine used, while the remainder is present in the form of an amine salt 'of-anllsubstituted carbamic acid of the formula Rmnocormn in which}! is as defined above. Under these con ditions the reaction product contains about 15-25 moi percent of unreacted amine, about 50. mol. percent of N-aliphatic-substituted carbamic acid and about 25-35 mol. percent of aliphatic-aubsti-v I h 8. it v mm es used f cmc st n g og ogtil u iby? the? applicant-m 'thermwettmg properties for use in the compositions of our invention are obtained when reaction products hav- 7 ing these percentage compositions are condensed with 2-10 mols of alkylene oxides.
The quantities of alkylene oxide condensed with .the mixture of carbamic acid salts should be limited to'avoid the formation of a product of excessive water-solubility, as otherwise the laun- 'dry-resistance of the finished composition will be Thus, for example; about 5-7 mols of ethylene olides'hoilld be condensed with mixinto guanidinium carbamates oftheforv t re in' which the aliphatic radicals. "contain- 16-18'carbonatoms, while quantities of 3-6 mols should be'used with guanidines of lower molecular weight. Larger quantities of propylene or butylene oxides 'up to about 8-10 mols may be used, since the water-solubilizing action of these compounds is notas great as that of ethylene oxide. In general, therefore, about 2-10 mol of 1 your; invention "is. still H -adniixtur e or, small fiquantitiesof water-soluble polyvalent'metal s'altstherewith. However these v p .fhotmo're than" 'isbout o. 1"-4%. bssed mbined weight r I onic surface' activef ge "of inorganic salts in which R is a saturated or unsaturated aliphatic radical of 12 or more carbon atoms, and preferably an unbranched aliphatic chain of 16-18 carbon atoms and Me is a salt-forming group such as sodium, ammonium, etc. The hexadecyl and octadecyl sulfosuccinamates are preferred to the corresponding compounds of lower molecular weight because of their reduced water-solubility, and this is also true of the corresponding mono esters of sulfosuccinic acid.
One of the most important advantages of the compositions of our invention. is the fact that they can be applied to textiles in conjunction with thermosetting. resin finishes such as methylol melamines containing 13-6 methylol groups, di-
methylolurea,-alky1ated methylol melamines such as tri, tetra, 1penta orhexamethylated methylol melamines or .withdimethylated dimethylol urea.
'These and similar resin finishes are usually applied froman aqueous bathwhich also contains an-acidicY-or. i aids-releasing curing accelerator 1 such as sdiammoniumjhydrogen phosphate,- phthalic acid, oxalic acid and the like. Any of the softening compositions .ofourinvention may 7 be added to these baths'in quantities suitable to give the desired softness: of'hand in the finished j textiles since-.thei-stability ofthe bath is. not reducedjitherebygffMoreoveriwe have found that the creaseproofingshrinkproofing action t tues-l b dsave-term n animation with. resin finishes therefore constitute another .important-featureofour invention. v I Theperman cyofith softenin -agents of uan ities h uld'i mlted thesubstitutedfcar salts and .,the ani- I may cause tendering-ofjfthetreated fabrics, but this tendency can be overcome by the addition an alkylene oxide of 2-4 carbon atoms should be used in preparing the cationic softening agents employed in the softeners of our invention, the
preferred compositions being those containing 5-7 mols of ethylene oxide for each molofan aliphatic amine of -16-l8 starting material.
. Any anionic surface-active agent containing a single long aliphatic radical'of 12 or more carbon atoms may be employed. Higher allryl sulfates carbon atoms used as resin finishes. v
of small quantities of water-soluble amides such as urea, thiourea and the like. The presence of these quantitiesof' polyvalent metal salts does not interfere with the application of the softening compositionin 'conjun'ctionwith resins and From the foregoing it will be seen that the improved textile softening compositions of our invention are those. which containa cationic softener consisting essentially of the condensation such as dodecyl, hexadecyl or octadecyl sulfate 1 or alkaryl sulfonates such as keryl benzene sulfonate may be used if desired. However, wefprefer to use the mono-esters or mono-amides of allphatic sulfocarboxylic acids, since these have given'good results in commercial practice. Monolauryl, monocetyl, monostearyl and monooleyl esters of sulfosuccinic acid, used .as thedisodium salts, have given very good results. Still better results are obtained with the corresponding 'sulfosuccinamates. mula:
These compounds have the forproduct of mixed aliphatic amine and aliphaticsubstituted guanidine salts oflN-aliphatic' carbamic acids in which the aliphatic radical contain 12-18 carbonatoms with 2-10 mols of an alkylene oxide of 2-4 carbon atoms, this cationic I softener being mixed with an'anionic surfaceerienh'anced by the sincelarser quantities I ay causefharshnessinHthetreated fabrics; jln 'some cases the presence of substantial -.qua n tities' of] these 1 inorganic salts atom are preferred, and in such mixtures optimum results are obtained with about 90-94% by weight of the cationic material and about 6-10% by weight of the anionic material. These compositions may be used as such or in admixture with 0.1-4% of water-soluble polyvalent metal salts such as aluminum sulfate, and in the latter case we prefer to add a water-soluble amide such as urea, thiourea and the like in amounts .'of about 1-5 times the weight of the metal salt.
The compositions of our invention may be applied to textiles by any of the known or approved methods for the application of softening agents.
Thus, for example,.they can be diluted with water to any desired consistency and textile materials, such as spun rayon, cotton or wool'cloth may be impregnated with the resulting solutions. The cloth is then preferably heated for suitable times at temperatures of ZOO-400 F. to convert the softener into a water-insoluble condition, after which the finish possesses excellent laundryresistance. This method of application may be combined'with the application of other finishing agents such as resins, starch, etc., as will hereinafter be described in greater detail.
The invention will be, further illustrated by the following specific examples, which describe the preparation of preferred ingredients and preferred softening compositions for textiles' It should be understood, however, that these examples are given primarily for purposes of i1- lustration and that the invention in its broader aspects is not limited thereto.
EXAMPLE 1 Lam-g1 disodium sulfosuccinainate I The lauryl ,disodi'um sulfosuccinamatewas then ground to a white powder easily soluble in water.
EXAMPLE 2 v Tetradecyl disodium sulfosuccinamate Tetradecyl disodium sulfosuccinamate was prepared using the general procedure described in Example 1 employing a commercial product was a white powder havinga sweet odor and a bitter taste. It was fairly soluble in water,- a 10% solution being slightly turbid at C.
. Exulrmr 3 Octadecyl disodium sulfosaccinamate Octadecyl disodium sulfosuccinamate was prepared by the method described in Example? using commercial octadecyl amine, C18I'I3'1NH2. The product was ayellow waxy powder having a mildly soapy odor and taste. It was dispersed in water to a paste.
EXAMPLE 4 Mixtures or higher aliphatic-substituted guanidine salts with carbamates of the corresponding higher alkyl amines are prepared by reacting the grade (88.5%) of tetradecyl amine, C14H29NH2. .The-
alkyl amines with aqueous cyanamide solutions in the presence of carbon dioxide. Reaction products in which about 15-40 mol percent of the amine has been converted into an aliphaticsubstituted guanidine produce the best textile softening compositions. With less than 15% of the amine converted into guanidine the composition exhibits yellowing on the fabric, while with more than 40%;the composition is too strongly basic and tends to neutralize acid curing agents of the type of diammonium hydrogen phosphate when used in textile finishing baths containing thermosetting resins.
A composition containing about 25-35% of the amine in the form of a higher aliphatic-substituted guanidine is formed by reacting the following materials:
Parts by weight octadecylamine 269 Isopropyl alcohol 135 Carbon dioxide 25 Water 17 Cyanamide (23.9% solution in water) by heating at 45 C. and then the solution is pumped into a reaction vessel along with the water. During 1.5 hours the carbon dioxide, in the form'of dry ice, is added in small portions, the temperature being kept below C. by cooling.
The carbon dioxide reacts with the amine to form and octadecyl amine N-octadecylcarbamate in which about 50% of the amine has been converted into N-octadecylcarbamate and about 30% is converted into mono octadecyl guanidine which is combined with a part of the octadecyl-substb tuted carbamic acid in the form of a guanidinium salt. The remainder of the amine is combined with the rest of the N-octadecyl carbamic acid inthe form of a salt.
A considerably cheaper product of approximately the same molecular composition and having equally good softening properties is obtained by substituting commercial mixtures of higher aliphatic amines for the octadecyl amine in the above preparation. Thus, for example, a mix- A ture containing about 25% 0f hexadecylamine,
25% of saturated octadecylamine and 50% of unsaturated primary amines of 18 carbon atoms is (5 responding molecular quantities.
The amine is dissolved in the isopropyl alcohol The guanidine carbamate mixture was condensed with alkylene oxide to form the condensation products used as cationic softeners in the compositions of the present invention. Upon completion of the procedure described above the vessel containing the reaction product was adapted for pressure and an ethylene oxide tank was attached so that ethylene oxide could be introduced above the surface of the reaction mixture. Ethylene oxide was slowly added at 60- 66 C. at a rate such that the internal pressure did not exceed 20 lbs. per square inch. Suflicient ethylene oxide was added during about 4 hours so that the final product contained not less than 5 nor more than 7 mols of the oxide for each mol of amine used as starting material. This amounted to 220-308 parts by weight of ethylene oxide.
8 for use in a textile finishing bath having the following composition:
Component:
Methylated methylol melamine (80%) weight in lbs. 86.0
Accelerator do 2.4 Softener do 6.0 Water to make gallons 100 The accelerator was a mixture of approximately four parts by weight of hexamethylene tetramine I and 30 parts of diammonium hydrogen phosphate.
Softness as determined by hand After soaping as follows: After Cure 5 min min. 60 min Softener A Fair. Softener B Do. Softener C. Good. Softener D Fair. Softener E Good. Softener F Do. Softener G. Very good. Softener H Do. CommerclalSoftener Soft but raggy. Example 4 alone Baggy. Blank Harsh.
l Cetyl dimethyl benzyl ammonium chloride.
After the ethylene oxide addition was completed the product was heated to 90 C. for a few minutes, then cooled to 70 C. and allowed to stand overnight. The next day it was concentrated by evaporation under a partial vacuum until a. sample showed a solids content of 80% upon distillation with benzene. The concentrated product.
Exunu: 5
Evaluation of softener compositions Various mixtures of the product of Example 4 with the product of Example 3 were prepared as shown in the following table:
Softener A B C D E F G H Example4(l00%) 24.5 24.5 25.5 18.0 2.5.0 20.0 30.0325 Example3(35%) 0 20. .5 .0 30.0 12.5 0.5 H01 Water ii 0 In all cases the two surface-active agents were dissolved in separate portions of water at 120 F. and the solutions were mixed and stirred for 15 minutes or until homogeneous.
The mixtures were then evaluated as softeners These results show that permanency against washing is obtained by mixing the cationic softeners with anionic surface-active agents throughout a range of ratios including as little as 58 parts by weight of the cationic softener to 42 parts by weight of the anionic surface-active agent (composition D) up to 93.5 parts of the softener to 6.5 parts of the anionic surface-active agent, as in composition H. However, the best hands are obtained when the alkylene oxide condensation products ar present in a substantial excess ranging from about 3-15:1. The cationic softeners alone will produce a very good hand on the resin-treated fabric, but are not resistant to soaping in the absence of the anionic surfaceactive agent.
ExAmL: 6
Composition of Softener Example 4 25 25. 00 25.0 25 25 Example 3 (35%). 5 5.00 5.0 5 5 Al1(SO4)s.l8H20-- 0 0. 25 0. 5 l 2 Water 70 69. 75 69. 5 69 68 6 eral times and the hand after each laundering was determined. The results obtained are given in the following table:
10 106% by weight of an anionic surface-active agent of the formula Me:S.OH.C0.0Mc
' m.oo.x
in which Me is a monovalent salt-forming radical and X is a member of the group of OR and NHR, B. being an aliphaticradical Softener 6 min. 50 min. 1 hour 2 hours 1 Vo soit full-.." V loft full-.-.- Vorysoit BoftbutsLraggy. 2 "H in in Verysoit,full.- Fullandsoft. 3 do do do Do. 4 Mediumsoft Mediumsoft Modiumsoit Do. 5 S1. harsh .harsh .hsrsh Sl. harsh. None Veryharsh.- Harsh Harsh Harsh.
The addition of a polyvalent metal salt such as aluminum sulfate in amounts of about 0.1-4% of the weight of the softener therefore assists materially in the retention of hand on soapini; but the addition of too much of the metal salt causes harshness.
EXAMPLE 7 Per cent by weight Product of Example 4 (80% solids) 40 Product of Example 3 (35% solids) 8 A1a(SO4)3.18H2O 0.26 Urea 0.52 Water 51.22
The product of Example 4" is preferably one in which the commercial mixture of hexadecyland octadecylamines is used as a starting material.
This composition decreases the bleeding of dyed fabrics and does not cause dye fading, it does not chalk or dust upon storage of the treated textiles and it can be applied along with thermosetting resin finishes from-the same bath of 12-18 carbon atoms, together with 0.1-4% of a water-soluble aluminum salt, based on the weight b of said mixture.
3. A softening composition for textiles comprising a mixture of 90-94% by weight of the condensation product of 5-7 mols of ethylene oxide with a mixture of 50-70 mol percent of an aliphatic-substituted guanidinium N-aliphatic carbamate and 50-30 mol percent of an aliphatic amine N-aliphatic carbamate in which the aliwithout impairing the bath stability or the curing action of curing accelerators contained therein.
What we claim is:
1. A softening composition for textiles comprising a mixture of 90-94% by weight of the condensation product of 5-7 mols of ethylene oxide with a mixture of 50-70 mol percent of an allphatic-substituted guanidinium N-aliphatic carbamate and 50-30 mol percent of an aliphatic amine N-aliphatic carbamate in which the all-- phatic radicals contain 16-18 carbon atoms and 10-6% by weight of an anionic surface-active agent containing a single long aliphatic radical of 16-18 carbon atoms together with 0.1-4% of a water-soluble aluminum salt, based on the weight of said mixture. a
2. A softening composition for textiles comprising a mixture of 90-94% by weight of the condensation product of 5-7 mols of ethylene oxide with a mixture of 50-70 mol percent of an aliphatic-substituted guanidinium N-aliphatic carbamate and 50-30 mol percent of an aliphatic amine N-aliphatic carbamate'in which the allphatic radicals contain 16-18 carbon atoms and phatic radicals contain 16-18 carbon atoms and 10-6% by weight of an N-aliphatic disodium sulfosuccinamate in which the aliphatic radical contains 16-18 carbon atoms, together with 0.1- 4% of aluminum sulfate, based on the weight of said mixture, and urea in amounts about twice the weight of said aluminum sulfate.
4. A softening composition for textiles comprising 58 to 96 parts by weight of the condensation product of a mixture of aliphatic amine and aliphatic-substituted guanidine salts of N-aliphatic carbamic acids in which the aliphatic radicals contain 12 to 18 carbon atoms with 2 to 10 mols of an alkylene oxide of 2 to 4 carbon atoms and 42 to 4 parts by weight of an anionic surfaceactive agent containing a single long aliphatic radical of 12 to 18 carbon atoms.
5. A composition according to claim 4 in which the mixture of aliphatic amine and aliphaticsubstituted guanidine salts of N-aliphatic carbamic acids is condensed with 3 to 7 mols of ethylene oxide.
6. A composition according to claim 5 in which the anionic surface-active agent is a compoun of the formula in which Me is a monovalent salt-forming radical and x is a member of the group consisting of --OR and NHR, It being an aliphatic radical of 12-18 carbon atoms.
7. A composition according to claim 6 which also contains 0.1 to 4% of a water-soluble polyvalent metal salt, based on the weight of the mixture recited in claim 6.
8.A composition according to claim 7. which also contains a water-soluble amide in an amount of about 1 to 5 times the weight of said polyvalent metal salt.
9. A composition according to claim 4 in which a mixture of aliphatic amine and aliphatic-substituted guanidine salts of N-aliphatic carbamic acids in which the aliphatic radicals contain 16-18 carbon atoms is condensed with 5-7 mols of ethylene oxide.
10. A softening composition for textiles comprising 58 to 96 parts by weight of the condensa- 11 tion product of a mixture of 50-70 mol percent of an aliphatic-substituted-guanidimum N-aliphatic carbamate and 50-30 mol per cent of an aliphatic amine N-aliphatic carbamate in which the aliphatic radicals contain 12-18 carbon atoms in which Me is a monovalent salt-forming radical and X is a member 01 the group consisting of OR and -NHR, B. being an aliphatic radical or 12-18 carbon atoms.
13. A composition according to claim 12 which also contains 0.1 to 4% of a water-soluble polyvalent metal salt, based on the weight of the mixture recited in claim 12.
14. A composition according to claim 13 which also contains a water-soluble amide in an amount of about 1 to 5 times the weight oi. said polyvalent metal salt.
15. A composition according to. claim 10 in which a mixture of aliphatic amine and aliphaticsubstituted guanidine salts of N-aliphatic carbamic acids in which the aliphatic radicals contain 16-18 carbon atoms is condensed with 5-7 mols of ethylene oxide.
16. A softening composition for textiles comprising -96% by weight of the condensation product or a mixture of aliphatic amine and allphatic-substituted guanidine salts of N-aliphatlc carbamic acids in which the aliphatic radicals contain 12-18 carbon atoms with 2-10 mols of an alkylene oxide of 2-4 carbon atoms and 204% by weight of an anionic surface-active agent containing a single aliphatic radical of 12-18 carbon atoms.
17. A composition according to claim 16 in which the mixture of aliphatic amine and aliphatic-substituted guanidine salts of N-aliphatic carbamic acids is condensed with 3 to 7 mols of ethylene oxide.
18. A composition according to claim 17 which also contains 0.1 to 4% of a water-soluble polyvalent metal salt based on the weight of the mixture recited in claim 6.
19. A composition according to claim 18 which also contains a water-soluble amide in an amount of about 1 to 5 times the weight of said polyvalent metal salt.
EMIL A. VITALIS. JOHN E. LYNN.
REFERENCES CITED The following references are of record in the file of this patent:
UNITED STATES PATENTS Jaeger Aug. 12, 1941
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US593758A US2427242A (en) | 1945-05-14 | 1945-05-14 | Textile softening composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US593758A US2427242A (en) | 1945-05-14 | 1945-05-14 | Textile softening composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2427242A true US2427242A (en) | 1947-09-09 |
Family
ID=24376040
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US593758A Expired - Lifetime US2427242A (en) | 1945-05-14 | 1945-05-14 | Textile softening composition |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2427242A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2573956A (en) * | 1949-06-28 | 1951-11-06 | American Cyanamid Co | Process for treating nonfibrous cellulosic film and resulting product |
| US2574510A (en) * | 1947-02-04 | 1951-11-13 | American Cyanamid Co | Cationic surface active agents and method of preparation |
| US2597708A (en) * | 1948-12-30 | 1952-05-20 | American Cyanamid Co | Antistatic agent, treatment of shaped articles therewith, and treated articles |
| US2637693A (en) * | 1949-04-16 | 1953-05-05 | Celanese Corp | Yarn lubricant |
| US2654678A (en) * | 1949-01-28 | 1953-10-06 | American Cyanamid Co | Antistatic treatment of shaped articles comprising a vinyl resin and treated articles |
| US2784159A (en) * | 1952-12-23 | 1957-03-05 | American Cyanamid Co | Flameproofing composition |
| US4153561A (en) * | 1976-12-31 | 1979-05-08 | Hoechst Aktiengesellschaft | Conditioning agent |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2142688A (en) * | 1936-06-13 | 1939-01-03 | Ig Farbenindustrie Ag | Artificial silk fabric |
| US2236074A (en) * | 1935-12-19 | 1941-03-25 | American Ecla Corp | Waterproofing of textile materials |
| US2252401A (en) * | 1937-04-15 | 1941-08-12 | American Cyanamid & Chem Corp | Amine derivatives of sulphodicarboxylic acids |
| US2258321A (en) * | 1939-08-12 | 1941-10-07 | American Cyanamid Co | Condensation products of amines and monoalkylol cyanamides |
| US2299012A (en) * | 1941-01-30 | 1942-10-13 | American Cyanamid Co | Symmetrical disubstituted alkylol guanidines |
| US2304113A (en) * | 1940-08-03 | 1942-12-08 | Arnold Hoffman & Co Inc | Treated textile product |
-
1945
- 1945-05-14 US US593758A patent/US2427242A/en not_active Expired - Lifetime
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2236074A (en) * | 1935-12-19 | 1941-03-25 | American Ecla Corp | Waterproofing of textile materials |
| US2142688A (en) * | 1936-06-13 | 1939-01-03 | Ig Farbenindustrie Ag | Artificial silk fabric |
| US2252401A (en) * | 1937-04-15 | 1941-08-12 | American Cyanamid & Chem Corp | Amine derivatives of sulphodicarboxylic acids |
| US2258321A (en) * | 1939-08-12 | 1941-10-07 | American Cyanamid Co | Condensation products of amines and monoalkylol cyanamides |
| US2304113A (en) * | 1940-08-03 | 1942-12-08 | Arnold Hoffman & Co Inc | Treated textile product |
| US2299012A (en) * | 1941-01-30 | 1942-10-13 | American Cyanamid Co | Symmetrical disubstituted alkylol guanidines |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2574510A (en) * | 1947-02-04 | 1951-11-13 | American Cyanamid Co | Cationic surface active agents and method of preparation |
| US2597708A (en) * | 1948-12-30 | 1952-05-20 | American Cyanamid Co | Antistatic agent, treatment of shaped articles therewith, and treated articles |
| US2654678A (en) * | 1949-01-28 | 1953-10-06 | American Cyanamid Co | Antistatic treatment of shaped articles comprising a vinyl resin and treated articles |
| US2637693A (en) * | 1949-04-16 | 1953-05-05 | Celanese Corp | Yarn lubricant |
| US2573956A (en) * | 1949-06-28 | 1951-11-06 | American Cyanamid Co | Process for treating nonfibrous cellulosic film and resulting product |
| US2784159A (en) * | 1952-12-23 | 1957-03-05 | American Cyanamid Co | Flameproofing composition |
| US4153561A (en) * | 1976-12-31 | 1979-05-08 | Hoechst Aktiengesellschaft | Conditioning agent |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US2427242A (en) | Textile softening composition | |
| US2694688A (en) | Antistatic compositions for textiles | |
| US2304369A (en) | Condensation product | |
| US2795513A (en) | Process for finishing textile material and product | |
| US3723377A (en) | Process of reducing formaldehyde odor of aqueous mixtures containing methylolated carbamates | |
| US2693460A (en) | Materials for finishing textiles and processes for producing and using the same | |
| US2784159A (en) | Flameproofing composition | |
| US2258321A (en) | Condensation products of amines and monoalkylol cyanamides | |
| US2785145A (en) | Siliconate-aminoplast compositions and textiles coated therewith | |
| US3958061A (en) | Composition for making textiles flame-proof and its application | |
| US2684346A (en) | Latent curing catalysts and compositions containing same | |
| US2491249A (en) | Water repellent composition containing stearamide and methylated methylol melamine | |
| US3087905A (en) | Durable fluorochemical-melamine resin textile finish | |
| US2688607A (en) | Modified melamine resin and process for preparing the same | |
| US2676936A (en) | Aqueous textile finishing composition containing methylol higher fatty acid monoamides | |
| US3871822A (en) | Treatment of cellulosic textile fabrics with methylolated alkoxyalkyl carbamates | |
| US2729577A (en) | Method of imparting antistatic properties to textile materials | |
| US3903033A (en) | Urea-glyoxal-formaldehyde cellulose reactant | |
| US2861054A (en) | Water repellents techniques | |
| US2302762A (en) | Isothioureas and process for making them | |
| GB683410A (en) | Production of impregnating agent for treating fibres or fibrecontaining substances and objects | |
| US3378397A (en) | Highly alkylolated textile finishing composition and process for treating textile fabric therewith | |
| US3134686A (en) | Durable antistatic finish and process for applying same | |
| US2850407A (en) | Textile finishing compositions containing adduct of beta-amino lower alkyl carbamateand formaldehyde, method of applying same, and the treated textile | |
| US2284609A (en) | Treatment of fibrous materials |