EP3421583A1 - Utilisation de copolymères vinylamine/vinylcarboxamide cationiques comme agent de protection des couleurs pour formulations de blanchissage - Google Patents

Utilisation de copolymères vinylamine/vinylcarboxamide cationiques comme agent de protection des couleurs pour formulations de blanchissage Download PDF

Info

Publication number: EP3421583A1
Authority: EP; European Patent Office
Prior art keywords: reactive; vinylcarboxamide; direct; cationic; mol
Prior art date: 2017-06-26
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 Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Withdrawn

Application number

EP17177768.3A

Other languages

German (de)

English (en)

Inventor

Yungi Lee

Alexandros LAMPROU

Hoang Trang TRAN-THIEN

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

BASF SE

Original Assignee

BASF SE

Priority date (The priority date 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 date listed.)

2017-06-26

Filing date

2017-06-26

Publication date

2019-01-02

2017-06-26 Application filed by BASF SE filed Critical BASF SE

2017-06-26 Priority to EP17177768.3A priority Critical patent/EP3421583A1/fr

2019-01-02 Publication of EP3421583A1 publication Critical patent/EP3421583A1/fr

Status Withdrawn legal-status Critical Current

Links

229920001577 copolymer Polymers 0.000 title claims abstract description 144
239000000203 mixture Substances 0.000 title claims abstract description 116
HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 title claims abstract description 111
125000002091 cationic group Chemical group 0.000 title claims abstract description 96
238000009472 formulation Methods 0.000 title claims abstract description 89
238000004900 laundering Methods 0.000 title claims abstract description 67
239000007788 liquid Substances 0.000 claims abstract description 35
238000000034 method Methods 0.000 claims abstract description 27
239000000975 dye Substances 0.000 claims description 108
239000003795 chemical substances by application Substances 0.000 claims description 50
239000004753 textile Substances 0.000 claims description 43
239000000178 monomer Substances 0.000 claims description 39
238000012546 transfer Methods 0.000 claims description 39
239000003945 anionic surfactant Substances 0.000 claims description 36
239000003112 inhibitor Substances 0.000 claims description 27
229920000742 Cotton Polymers 0.000 claims description 19
ZQXSMRAEXCEDJD-UHFFFAOYSA-N n-ethenylformamide Chemical compound C=CNC=O ZQXSMRAEXCEDJD-UHFFFAOYSA-N 0.000 claims description 17
UYMKPFRHYYNDTL-UHFFFAOYSA-N ethenamine Chemical compound NC=C UYMKPFRHYYNDTL-UHFFFAOYSA-N 0.000 claims description 14
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 12
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
229920001519 homopolymer Polymers 0.000 claims description 11
238000002360 preparation method Methods 0.000 claims description 11
239000000985 reactive dye Substances 0.000 claims description 8
QTTDXDAWQMDLOF-UHFFFAOYSA-J tetrasodium 3-[[4-[[4-[(6-amino-1-hydroxy-3-sulfonatonaphthalen-2-yl)diazenyl]-6-sulfonatonaphthalen-1-yl]diazenyl]naphthalen-1-yl]diazenyl]naphthalene-1,5-disulfonate Chemical compound [Na+].[Na+].[Na+].[Na+].Nc1ccc2c(O)c(N=Nc3ccc(N=Nc4ccc(N=Nc5cc(c6cccc(c6c5)S([O-])(=O)=O)S([O-])(=O)=O)c5ccccc45)c4ccc(cc34)S([O-])(=O)=O)c(cc2c1)S([O-])(=O)=O QTTDXDAWQMDLOF-UHFFFAOYSA-J 0.000 claims description 8
HZBTZQVWJPRVDN-UHFFFAOYSA-J copper;disodium;5-[[4-[4-[[2,6-dioxido-3-[(2-oxido-5-sulfonatophenyl)diazenyl]phenyl]diazenyl]phenyl]phenyl]diazenyl]-2-oxidobenzoate;hydron Chemical compound [H+].[H+].[Na+].[Na+].[Cu+2].C1=C([O-])C(C(=O)[O-])=CC(N=NC=2C=CC(=CC=2)C=2C=CC(=CC=2)N=NC=2C(=C(N=NC=3C(=CC=C(C=3)S([O-])(=O)=O)[O-])C=CC=2[O-])[O-])=C1 HZBTZQVWJPRVDN-UHFFFAOYSA-J 0.000 claims description 6
239000000982 direct dye Substances 0.000 claims description 6
239000000463 material Substances 0.000 claims description 5
UWOFGIXNNCPENM-UHFFFAOYSA-N 3,3-difluoropentan-2-one Chemical compound CCC(F)(F)C(C)=O UWOFGIXNNCPENM-UHFFFAOYSA-N 0.000 claims description 4
INOIOAWTVPHTCJ-UHFFFAOYSA-N 6-acetamido-4-hydroxy-3-[[4-(2-sulfooxyethylsulfonyl)phenyl]diazenyl]naphthalene-2-sulfonic acid Chemical compound CC(=O)NC1=CC=C2C=C(C(N=NC3=CC=C(C=C3)S(=O)(=O)CCOS(O)(=O)=O)=C(O)C2=C1)S(O)(=O)=O INOIOAWTVPHTCJ-UHFFFAOYSA-N 0.000 claims description 4
KXXFHLLUPUAVRY-UHFFFAOYSA-J [Na+].[Na+].[Na+].[Cu++].[O-]C(=O)C1=CC=C(C=C1N=N[C-](N=NC1=C([O-])C(NC2=NC(F)=NC(NCCOCCS(=O)(=O)C=C)=N2)=CC(=C1)S([O-])(=O)=O)C1=CC=CC=C1)S([O-])(=O)=O Chemical compound [Na+].[Na+].[Na+].[Cu++].[O-]C(=O)C1=CC=C(C=C1N=N[C-](N=NC1=C([O-])C(NC2=NC(F)=NC(NCCOCCS(=O)(=O)C=C)=N2)=CC(=C1)S([O-])(=O)=O)C1=CC=CC=C1)S([O-])(=O)=O KXXFHLLUPUAVRY-UHFFFAOYSA-J 0.000 claims description 4
239000000413 hydrolysate Substances 0.000 claims description 4
238000010348 incorporation Methods 0.000 claims description 4
RQAKESSLMFZVMC-UHFFFAOYSA-N n-ethenylacetamide Chemical compound CC(=O)NC=C RQAKESSLMFZVMC-UHFFFAOYSA-N 0.000 claims description 4
HTPJPKXFBLUBPI-UHFFFAOYSA-I pentasodium 5-[[4-[[4-anilino-6-[[8-hydroxy-7-[[4-[(8-hydroxy-3,6-disulfonatonaphthalen-1-yl)diazenyl]-2-methoxy-5-methylphenyl]diazenyl]-3,6-disulfonatonaphthalen-1-yl]amino]-1,3,5-triazin-2-yl]amino]phenyl]diazenyl]-2-hydroxybenzoate Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].COc1cc(N=Nc2cc(cc3cc(cc(O)c23)S([O-])(=O)=O)S([O-])(=O)=O)c(C)cc1N=Nc1c(O)c2c(Nc3nc(Nc4ccccc4)nc(Nc4ccc(cc4)N=Nc4ccc(O)c(c4)C([O-])=O)n3)cc(cc2cc1S([O-])(=O)=O)S([O-])(=O)=O HTPJPKXFBLUBPI-UHFFFAOYSA-I 0.000 claims description 4
FIXVWFINKCQNFG-UHFFFAOYSA-M sodium;4-[(4-aminophenyl)diazenyl]benzenesulfonate Chemical compound [Na+].C1=CC(N)=CC=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 FIXVWFINKCQNFG-UHFFFAOYSA-M 0.000 claims description 3
BMCYONWPAXGKRH-UHFFFAOYSA-N 2-[3-(ethylamino)phenyl]sulfonylethyl hydrogen sulfate Chemical compound CCNC1=CC=CC(S(=O)(=O)CCOS(O)(=O)=O)=C1 BMCYONWPAXGKRH-UHFFFAOYSA-N 0.000 claims description 2
AVERNFJXXRIVQN-XSDYUOFFSA-N 5-[(4-ethoxyphenyl)diazenyl]-2-[(e)-2-[4-[(4-ethoxyphenyl)diazenyl]-2-sulfophenyl]ethenyl]benzenesulfonic acid Chemical compound C1=CC(OCC)=CC=C1N=NC(C=C1S(O)(=O)=O)=CC=C1\C=C\C1=CC=C(N=NC=2C=CC(OCC)=CC=2)C=C1S(O)(=O)=O AVERNFJXXRIVQN-XSDYUOFFSA-N 0.000 claims description 2
IQFVPQOLBLOTPF-UHFFFAOYSA-L Congo Red Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(N=NC3=CC=C(C=C3)C3=CC=C(C=C3)N=NC3=C(C4=CC=CC=C4C(=C3)S([O-])(=O)=O)N)=CC(S([O-])(=O)=O)=C21 IQFVPQOLBLOTPF-UHFFFAOYSA-L 0.000 claims description 2
OVSNDJXCFPSPDZ-UHFFFAOYSA-N Reactive red 120 Chemical compound OS(=O)(=O)C1=CC2=CC(S(O)(=O)=O)=CC(NC=3N=C(NC=4C=CC(NC=5N=C(NC=6C7=C(O)C(N=NC=8C(=CC=CC=8)S(O)(=O)=O)=C(C=C7C=C(C=6)S(O)(=O)=O)S(O)(=O)=O)N=C(Cl)N=5)=CC=4)N=C(Cl)N=3)=C2C(O)=C1N=NC1=CC=CC=C1S(O)(=O)=O OVSNDJXCFPSPDZ-UHFFFAOYSA-N 0.000 claims description 2
229910052799 carbon Inorganic materials 0.000 claims description 2
HFIYIRIMGZMCPC-UHFFFAOYSA-J chembl1326377 Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]S(=O)(=O)C1=CC2=CC(S([O-])(=O)=O)=C(N=NC=3C=CC(=CC=3)S(=O)(=O)CCOS([O-])(=O)=O)C(O)=C2C(N)=C1N=NC1=CC=C(S(=O)(=O)CCOS([O-])(=O)=O)C=C1 HFIYIRIMGZMCPC-UHFFFAOYSA-J 0.000 claims description 2
OIQPTROHQCGFEF-UHFFFAOYSA-L chembl1371409 Chemical compound [Na+].[Na+].OC1=CC=C2C=C(S([O-])(=O)=O)C=CC2=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 OIQPTROHQCGFEF-UHFFFAOYSA-L 0.000 claims description 2
XRPLBRIHZGVJIC-UHFFFAOYSA-L chembl3182776 Chemical compound [Na+].[Na+].NC1=CC(N)=CC=C1N=NC1=CC=C(C=2C=CC(=CC=2)N=NC=2C(=CC3=CC(=C(N=NC=4C=CC=CC=4)C(O)=C3C=2N)S([O-])(=O)=O)S([O-])(=O)=O)C=C1 XRPLBRIHZGVJIC-UHFFFAOYSA-L 0.000 claims description 2
VAVKOHVLNBBLQE-UHFFFAOYSA-I copper;trisodium;5-acetamido-4-oxido-3-[[2-oxido-5-(2-sulfonatooxyethylsulfonyl)phenyl]diazenyl]naphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].[Na+].[Cu+2].[O-]C1=C2C(NC(=O)C)=CC(S([O-])(=O)=O)=CC2=CC(S([O-])(=O)=O)=C1N=NC1=CC(S(=O)(=O)CCOS([O-])(=O)=O)=CC=C1[O-] VAVKOHVLNBBLQE-UHFFFAOYSA-I 0.000 claims description 2
UZZFFIUHUDOYPS-UHFFFAOYSA-L disodium 4-amino-3,6-bis[[4-[(2,4-diaminophenyl)diazenyl]phenyl]diazenyl]-5-oxido-7-sulfonaphthalene-2-sulfonate Chemical compound [Na+].[Na+].Nc1ccc(N=Nc2ccc(cc2)N=Nc2c(N)c3c(O)c(N=Nc4ccc(cc4)N=Nc4ccc(N)cc4N)c(cc3cc2S([O-])(=O)=O)S([O-])(=O)=O)c(N)c1 UZZFFIUHUDOYPS-UHFFFAOYSA-L 0.000 claims description 2
OYUZMQYZGSMPII-UHFFFAOYSA-L disodium 4-hydroxy-7-[(5-hydroxy-6-phenyldiazenyl-7-sulfonatonaphthalen-2-yl)amino]-3-phenyldiazenylnaphthalene-2-sulfonate Chemical compound [Na+].[Na+].Oc1c(N=Nc2ccccc2)c(cc2cc(Nc3ccc4c(O)c(N=Nc5ccccc5)c(cc4c3)S([O-])(=O)=O)ccc12)S([O-])(=O)=O OYUZMQYZGSMPII-UHFFFAOYSA-L 0.000 claims description 2
DSARWKALPGYFTA-UHFFFAOYSA-L disodium 4-hydroxy-7-[(5-hydroxy-6-phenyldiazenyl-7-sulfonatonaphthalen-2-yl)carbamoylamino]-3-phenyldiazenylnaphthalene-2-sulfonate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)C1=CC2=CC(NC(=O)NC=3C=C4C=C(C(N=NC=5C=CC=CC=5)=C(O)C4=CC=3)S([O-])(=O)=O)=CC=C2C(O)=C1N=NC1=CC=CC=C1 DSARWKALPGYFTA-UHFFFAOYSA-L 0.000 claims description 2
PHBXSOKXCTZJBO-UHFFFAOYSA-L disodium 7-amino-4-hydroxy-3-[[4-[4-[(1-hydroxy-4-sulfonatonaphthalen-2-yl)diazenyl]-3-methoxyphenyl]-2-methoxyphenyl]diazenyl]naphthalene-2-sulfonate Chemical compound [Na+].[Na+].COc1cc(ccc1N=Nc1cc(c2ccccc2c1O)S([O-])(=O)=O)-c1ccc(N=Nc2c(O)c3ccc(N)cc3cc2S([O-])(=O)=O)c(OC)c1 PHBXSOKXCTZJBO-UHFFFAOYSA-L 0.000 claims description 2
SKZFGYYJDVHJSA-UHFFFAOYSA-L disodium;4-[[2,4-diamino-5-[[4-[4-[(4-carboxy-3-oxidophenyl)diazenyl]phenyl]phenyl]diazenyl]phenyl]diazenyl]benzenesulfonate Chemical compound [Na+].[Na+].NC1=CC(N)=C(N=NC=2C=CC(=CC=2)S([O-])(=O)=O)C=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1N=NC1=CC=C(C([O-])=O)C(O)=C1 SKZFGYYJDVHJSA-UHFFFAOYSA-L 0.000 claims description 2
YYOYUTRZHZNCFZ-UHFFFAOYSA-I pentasodium 5-[[4-chloro-6-[4-(2-sulfooxyethylsulfonyl)anilino]-1,3,5-triazin-2-yl]amino]-3-[(1,5-disulfonatonaphthalen-2-yl)diazenyl]-4-oxidonaphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].Oc1c(N=Nc2ccc3c(cccc3c2S([O-])(=O)=O)S([O-])(=O)=O)c(cc2cc(cc(Nc3nc(Cl)nc(Nc4ccc(cc4)S(=O)(=O)CCOS([O-])(=O)=O)n3)c12)S([O-])(=O)=O)S([O-])(=O)=O YYOYUTRZHZNCFZ-UHFFFAOYSA-I 0.000 claims description 2
MDNHFVJYEPHAAQ-VPMNAVQSSA-L procion yellow MX-4R Chemical compound [Na+].[Na+].COC1=CC=C(S(=O)(=O)CCOS([O-])(=O)=O)C=C1\N=N\C1C(=O)N(C=2C(=CC(=CC=2C)S([O-])(=O)=O)Cl)N=C1C MDNHFVJYEPHAAQ-VPMNAVQSSA-L 0.000 claims description 2
KXXXUIKPSVVSAW-UHFFFAOYSA-K pyranine Chemical compound [Na+].[Na+].[Na+].C1=C2C(O)=CC(S([O-])(=O)=O)=C(C=C3)C2=C2C3=C(S([O-])(=O)=O)C=C(S([O-])(=O)=O)C2=C1 KXXXUIKPSVVSAW-UHFFFAOYSA-K 0.000 claims description 2
KUIXZSYWBHSYCN-UHFFFAOYSA-L remazol brilliant blue r Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C(N)=C2C(=O)C3=CC=CC=C3C(=O)C2=C1NC1=CC=CC(S(=O)(=O)CCOS([O-])(=O)=O)=C1 KUIXZSYWBHSYCN-UHFFFAOYSA-L 0.000 claims description 2
BQHRKYUXVHKLLZ-UHFFFAOYSA-M sodium 7-amino-2-[[4-[(4-aminophenyl)diazenyl]-2-methoxy-5-methylphenyl]diazenyl]-3-sulfonaphthalen-1-olate Chemical compound [Na+].COc1cc(N=Nc2ccc(N)cc2)c(C)cc1N=Nc1c(O)c2cc(N)ccc2cc1S([O-])(=O)=O BQHRKYUXVHKLLZ-UHFFFAOYSA-M 0.000 claims description 2
239000012209 synthetic fiber Substances 0.000 claims description 2
229920002994 synthetic fiber Polymers 0.000 claims description 2
OLSOUGWNONTDCK-UHFFFAOYSA-J tetrasodium 5-amino-3-[[4-[4-[(8-amino-1-hydroxy-3,6-disulfonatonaphthalen-2-yl)diazenyl]-3-methoxyphenyl]-2-methoxyphenyl]diazenyl]-4-hydroxynaphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].[Na+].[Na+].C1=C(S([O-])(=O)=O)C=C2C=C(S([O-])(=O)=O)C(N=NC3=CC=C(C=C3OC)C=3C=C(C(=CC=3)N=NC=3C(=CC4=CC(=CC(N)=C4C=3O)S([O-])(=O)=O)S([O-])(=O)=O)OC)=C(O)C2=C1N OLSOUGWNONTDCK-UHFFFAOYSA-J 0.000 claims description 2
MPCYPRXRVWZKGF-UHFFFAOYSA-J tetrasodium 5-amino-3-[[4-[4-[(8-amino-1-hydroxy-3,6-disulfonatonaphthalen-2-yl)diazenyl]phenyl]phenyl]diazenyl]-4-hydroxynaphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].[Na+].[Na+].C1=C(S([O-])(=O)=O)C=C2C=C(S([O-])(=O)=O)C(N=NC3=CC=C(C=C3)C3=CC=C(C=C3)N=NC3=C(C=C4C=C(C=C(C4=C3O)N)S([O-])(=O)=O)S([O-])(=O)=O)=C(O)C2=C1N MPCYPRXRVWZKGF-UHFFFAOYSA-J 0.000 claims description 2
GWAKFAUFNNPZFE-UHFFFAOYSA-K trisodium 2-[4-[(2-amino-4-oxidophenyl)diazenyl]anilino]-5-[(1-amino-8-oxido-7-phenyldiazenyl-3,6-disulfonaphthalen-2-yl)diazenyl]benzenesulfonate Chemical compound NC1=C(C(=CC2=CC(=C(C(=C12)O)N=NC1=CC=CC=C1)S(=O)(=O)[O-])S(=O)(=O)[O-])N=NC1=CC(=C(C=C1)NC1=CC=C(C=C1)N=NC1=C(C=C(C=C1)O)N)S(=O)(=O)[O-].[Na+].[Na+].[Na+] GWAKFAUFNNPZFE-UHFFFAOYSA-K 0.000 claims description 2
IHVXOVVDYSKGMH-UHFFFAOYSA-K trisodium 2-[[6-[(4-amino-6-chloro-1,3,5-triazin-2-yl)-methylamino]-1-hydroxy-3-sulfonatonaphthalen-2-yl]diazenyl]naphthalene-1,5-disulfonate Chemical compound [Na+].[Na+].[Na+].CN(c1ccc2c(O)c(N=Nc3ccc4c(cccc4c3S([O-])(=O)=O)S([O-])(=O)=O)c(cc2c1)S([O-])(=O)=O)c1nc(N)nc(Cl)n1 IHVXOVVDYSKGMH-UHFFFAOYSA-K 0.000 claims description 2
YQEHHPFEQLDFCN-UHFFFAOYSA-K trisodium 5-[(4,6-dichloro-1,3,5-triazin-2-yl)amino]-4-hydroxy-3-[(2-sulfonatophenyl)diazenyl]naphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].[Na+].Oc1c(N=Nc2ccccc2S([O-])(=O)=O)c(cc2cc(cc(Nc3nc(Cl)nc(Cl)n3)c12)S([O-])(=O)=O)S([O-])(=O)=O YQEHHPFEQLDFCN-UHFFFAOYSA-K 0.000 claims description 2
QTFHTNFVUCUDIR-UHFFFAOYSA-K trisodium 6-[(2,4-diaminophenyl)diazenyl]-3-[[4-[4-[[7-[(2,4-diaminophenyl)diazenyl]-1-hydroxy-3-sulfonatonaphthalen-2-yl]diazenyl]-2-sulfonatoanilino]phenyl]diazenyl]-4-hydroxynaphthalene-2-sulfonate Chemical compound C1=CC(=CC=C1NC2=C(C=C(C=C2)N=NC3=C(C=C4C=CC(=CC4=C3[O-])N=NC5=C(C=C(C=C5)N)N)S(=O)(=O)O)S(=O)(=O)[O-])N=NC6=C(C=C7C=CC(=CC7=C6[O-])N=NC8=C(C=C(C=C8)N)N)S(=O)(=O)O.[Na+].[Na+].[Na+] QTFHTNFVUCUDIR-UHFFFAOYSA-K 0.000 claims description 2
MBAYVHBJJXOOIY-UHFFFAOYSA-K trisodium 7-[[4-chloro-6-(3-sulfonatoanilino)-1,3,5-triazin-2-yl]-methylamino]-4-hydroxy-3-[(2-sulfonatophenyl)diazenyl]naphthalene-2-sulfonate Chemical compound [Na+].[Na+].[Na+].CN(c1ccc2c(O)c(N=Nc3ccccc3S([O-])(=O)=O)c(cc2c1)S([O-])(=O)=O)c1nc(Cl)nc(Nc2cccc(c2)S([O-])(=O)=O)n1 MBAYVHBJJXOOIY-UHFFFAOYSA-K 0.000 claims description 2
WTPOYMNMKZIOGO-UHFFFAOYSA-K trisodium;2,5-dichloro-4-[4-[[5-[[4-chloro-6-(4-sulfonatoanilino)-1,3,5-triazin-2-yl]amino]-2-sulfonatophenyl]diazenyl]-3-methyl-5-oxo-4h-pyrazol-1-yl]benzenesulfonate Chemical compound [Na+].[Na+].[Na+].CC1=NN(C=2C(=CC(=C(Cl)C=2)S([O-])(=O)=O)Cl)C(=O)C1N=NC(C(=CC=1)S([O-])(=O)=O)=CC=1NC(N=1)=NC(Cl)=NC=1NC1=CC=C(S([O-])(=O)=O)C=C1 WTPOYMNMKZIOGO-UHFFFAOYSA-K 0.000 claims description 2
UPDVDGUOBRUKAJ-UHFFFAOYSA-K trisodium;2-[[4-[[4-[(4,6-dichloro-1,3,5-triazin-2-yl)amino]-5-sulfonatonaphthalen-1-yl]diazenyl]-2,5-dimethylphenyl]diazenyl]benzene-1,4-disulfonate Chemical compound [Na+].[Na+].[Na+].CC=1C=C(N=NC=2C(=CC=C(C=2)S([O-])(=O)=O)S([O-])(=O)=O)C(C)=CC=1N=NC(C1=CC=CC(=C11)S([O-])(=O)=O)=CC=C1NC1=NC(Cl)=NC(Cl)=N1 UPDVDGUOBRUKAJ-UHFFFAOYSA-K 0.000 claims description 2
STOOUUMSJPLRNI-UHFFFAOYSA-N 5-amino-4-hydroxy-3-[[4-[4-[(4-hydroxyphenyl)diazenyl]phenyl]phenyl]diazenyl]-6-[(4-nitrophenyl)diazenyl]naphthalene-2,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC2=CC(S(O)(=O)=O)=C(N=NC=3C=CC(=CC=3)C=3C=CC(=CC=3)N=NC=3C=CC(O)=CC=3)C(O)=C2C(N)=C1N=NC1=CC=C([N+]([O-])=O)C=C1 STOOUUMSJPLRNI-UHFFFAOYSA-N 0.000 claims 1
ICIJDHUPWYQXGB-UHFFFAOYSA-N chembl1092740 Chemical compound C1=CC(NC(=O)C)=CC=C1N=NC(C(=CC1=C2)S(O)(=O)=O)=C(O)C1=CC=C2NC(=O)NC1=CC=C(C(O)=C(N=NC=2C=CC=CC=2)C(=C2)S(O)(=O)=O)C2=C1 ICIJDHUPWYQXGB-UHFFFAOYSA-N 0.000 claims 1
NDHOYLRUTRKFBM-UHFFFAOYSA-L disodium 6-amino-5-[[4-[4-[(1-amino-4-sulfonatonaphthalen-2-yl)diazenyl]phenyl]phenyl]diazenyl]-4-hydroxynaphthalene-2-sulfonate Chemical compound NC1=CC=C2C=C(C=C(O)C2=C1N=NC1=CC=C(C=C1)C1=CC=C(C=C1)N=NC1=C(N)C2=CC=CC=C2C(=C1)S(=O)(=O)O[Na])S(=O)(=O)O[Na] NDHOYLRUTRKFBM-UHFFFAOYSA-L 0.000 claims 1
238000005406 washing Methods 0.000 description 36
239000003599 detergent Substances 0.000 description 34
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229920002125 Sokalan® Polymers 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
HVWGGPRWKSHASF-UHFFFAOYSA-N Sulfuric acid, monooctadecyl ester Chemical compound CCCCCCCCCCCCCCCCCCOS(O)(=O)=O HVWGGPRWKSHASF-UHFFFAOYSA-N 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical class OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 1
BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
YDONNITUKPKTIG-UHFFFAOYSA-N [Nitrilotris(methylene)]trisphosphonic acid Chemical compound OP(O)(=O)CN(CP(O)(O)=O)CP(O)(O)=O YDONNITUKPKTIG-UHFFFAOYSA-N 0.000 description 1
SWLWZVHQLWXZTQ-UHFFFAOYSA-N acetonitrile;4-methylmorpholin-4-ium;methyl sulfate Chemical compound CC#N.COS([O-])(=O)=O.C[NH+]1CCOCC1 SWLWZVHQLWXZTQ-UHFFFAOYSA-N 0.000 description 1
239000013543 active substance Substances 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
125000002723 alicyclic group Chemical group 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
150000005215 alkyl ethers Chemical class 0.000 description 1
239000002168 alkylating agent Substances 0.000 description 1
229940100198 alkylating agent Drugs 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
235000019418 amylase Nutrition 0.000 description 1
229940025131 amylases Drugs 0.000 description 1
JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
229940053200 antiepileptics fatty acid derivative Drugs 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
235000003704 aspartic acid Nutrition 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
239000003139 biocide Substances 0.000 description 1
229920001400 block copolymer Polymers 0.000 description 1
239000000872 buffer Substances 0.000 description 1
238000012662 bulk polymerization Methods 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
239000008112 carboxymethyl-cellulose Substances 0.000 description 1
229920003118 cationic copolymer Polymers 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229940080284 cetyl sulfate Drugs 0.000 description 1
238000012512 characterization method Methods 0.000 description 1
NLMHXPDMNXMQBY-UHFFFAOYSA-L chembl260999 Chemical compound [Na+].[Na+].C1=CC(NC(=O)C)=CC=C1N=NC(C(=CC1=C2)S([O-])(=O)=O)=C(O)C1=CC=C2NC(=O)NC1=CC=C(C(O)=C(N=NC=2C=CC=CC=2)C(=C2)S([O-])(=O)=O)C2=C1 NLMHXPDMNXMQBY-UHFFFAOYSA-L 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
229910001919 chlorite Inorganic materials 0.000 description 1
229910052619 chlorite group Inorganic materials 0.000 description 1
FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
229940106681 chloroacetic acid Drugs 0.000 description 1
QBWCMBCROVPCKQ-UHFFFAOYSA-N chlorous acid Chemical compound OCl=O QBWCMBCROVPCKQ-UHFFFAOYSA-N 0.000 description 1
238000005056 compaction Methods 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
239000000470 constituent Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
239000002537 cosmetic Substances 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
STZIXLPVKZUAMV-UHFFFAOYSA-N cyclopentane-1,1,2,2-tetracarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CCCC1(C(O)=O)C(O)=O STZIXLPVKZUAMV-UHFFFAOYSA-N 0.000 description 1
239000008367 deionised water Substances 0.000 description 1
229910021641 deionized water Inorganic materials 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 description 1
VLFKFKCRUCJVNE-UHFFFAOYSA-L disodium 8-amino-7-[(4-nitrophenyl)diazenyl]-2-[[4-[4-[(4-oxidophenyl)diazenyl]phenyl]phenyl]diazenyl]-3,6-disulfonaphthalen-1-olate Chemical compound [Na+].[Na+].NC1=C(C(=CC2=CC(=C(C(=C12)O)N=NC1=CC=C(C=C1)C1=CC=C(C=C1)N=NC1=CC=C(C=C1)O)S(=O)(=O)[O-])S(=O)(=O)[O-])N=NC1=CC=C(C=C1)[N+](=O)[O-] VLFKFKCRUCJVNE-UHFFFAOYSA-L 0.000 description 1
BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
229940043264 dodecyl sulfate Drugs 0.000 description 1
DUYCTCQXNHFCSJ-UHFFFAOYSA-N dtpmp Chemical compound OP(=O)(O)CN(CP(O)(O)=O)CCN(CP(O)(=O)O)CCN(CP(O)(O)=O)CP(O)(O)=O DUYCTCQXNHFCSJ-UHFFFAOYSA-N 0.000 description 1
NFDRPXJGHKJRLJ-UHFFFAOYSA-N edtmp Chemical compound OP(O)(=O)CN(CP(O)(O)=O)CCN(CP(O)(O)=O)CP(O)(O)=O NFDRPXJGHKJRLJ-UHFFFAOYSA-N 0.000 description 1
238000010894 electron beam technology Methods 0.000 description 1
238000007720 emulsion polymerization reaction Methods 0.000 description 1
238000011067 equilibration Methods 0.000 description 1
GFJVXXWOPWLRNU-UHFFFAOYSA-N ethenyl formate Chemical compound C=COC=O GFJVXXWOPWLRNU-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
230000007717 exclusion Effects 0.000 description 1
239000003337 fertilizer Substances 0.000 description 1
239000002657 fibrous material Substances 0.000 description 1
238000005189 flocculation Methods 0.000 description 1
230000016615 flocculation Effects 0.000 description 1
239000012530 fluid Substances 0.000 description 1
239000003205 fragrance Substances 0.000 description 1
238000010528 free radical solution polymerization reaction Methods 0.000 description 1
239000000499 gel Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
239000000174 gluconic acid Substances 0.000 description 1
235000012208 gluconic acid Nutrition 0.000 description 1
125000004395 glucoside group Chemical group 0.000 description 1
239000008187 granular material Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 1
125000002636 imidazolinyl group Chemical group 0.000 description 1
150000004693 imidazolium salts Chemical class 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
239000003999 initiator Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
235000019421 lipase Nutrition 0.000 description 1
239000012669 liquid formulation Substances 0.000 description 1
229910003002 lithium salt Inorganic materials 0.000 description 1
159000000002 lithium salts Chemical class 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
GORGQKRVQGXVEB-UHFFFAOYSA-N n-ethenyl-n-ethylacetamide Chemical compound CCN(C=C)C(C)=O GORGQKRVQGXVEB-UHFFFAOYSA-N 0.000 description 1
PNLUGRYDUHRLOF-UHFFFAOYSA-N n-ethenyl-n-methylacetamide Chemical compound C=CN(C)C(C)=O PNLUGRYDUHRLOF-UHFFFAOYSA-N 0.000 description 1
OFESGEKAXKKFQT-UHFFFAOYSA-N n-ethenyl-n-methylformamide Chemical compound C=CN(C)C=O OFESGEKAXKKFQT-UHFFFAOYSA-N 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
150000004767 nitrides Chemical class 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
125000004433 nitrogen atom Chemical group N* 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000002245 particle Substances 0.000 description 1
239000006072 paste Substances 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
150000003009 phosphonic acids Chemical class 0.000 description 1
229920000885 poly(2-vinylpyridine) Polymers 0.000 description 1
229920005646 polycarboxylate Polymers 0.000 description 1
229920000867 polyelectrolyte Polymers 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
230000000379 polymerizing effect Effects 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
239000011591 potassium Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
UIIIBRHUICCMAI-UHFFFAOYSA-N prop-2-ene-1-sulfonic acid Chemical compound OS(=O)(=O)CC=C UIIIBRHUICCMAI-UHFFFAOYSA-N 0.000 description 1
ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
230000005855 radiation Effects 0.000 description 1
238000010526 radical polymerization reaction Methods 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
239000012966 redox initiator Substances 0.000 description 1
239000000523 sample Substances 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000000344 soap Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
URLJMZWTXZTZRR-UHFFFAOYSA-N sodium myristyl sulfate Chemical compound CCCCCCCCCCCCCCOS(O)(=O)=O URLJMZWTXZTZRR-UHFFFAOYSA-N 0.000 description 1
229950005425 sodium myristyl sulfate Drugs 0.000 description 1
239000012418 sodium perborate tetrahydrate Substances 0.000 description 1
IBDSNZLUHYKHQP-UHFFFAOYSA-N sodium;3-oxidodioxaborirane;tetrahydrate Chemical compound O.O.O.O.[Na+].[O-]B1OO1 IBDSNZLUHYKHQP-UHFFFAOYSA-N 0.000 description 1
KVSYNOOPFSVLNF-UHFFFAOYSA-M sodium;4-nonanoyloxybenzenesulfonate Chemical compound [Na+].CCCCCCCCC(=O)OC1=CC=C(S([O-])(=O)=O)C=C1 KVSYNOOPFSVLNF-UHFFFAOYSA-M 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
238000010186 staining Methods 0.000 description 1
238000005728 strengthening Methods 0.000 description 1
230000001180 sulfating effect Effects 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
238000010557 suspension polymerization reaction Methods 0.000 description 1
239000003760 tallow Substances 0.000 description 1
239000008399 tap water Substances 0.000 description 1
235000020679 tap water Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical compound OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
239000004034 viscosity adjusting agent Substances 0.000 description 1
229920003169 water-soluble polymer Polymers 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
210000002268 wool Anatomy 0.000 description 1
239000004711 α-olefin Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/0005—Other compounding ingredients characterised by their effect
- C11D3/0021—Dye-stain or dye-transfer inhibiting compositions
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/37—Polymers
- C11D3/3746—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C11D3/3769—(Co)polymerised monomers containing nitrogen, e.g. carbonamides, nitriles or amines
- 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
- C11D2111/00—Cleaning compositions characterised by the objects to be cleaned; Cleaning compositions characterised by non-standard cleaning or washing processes
- C11D2111/10—Objects to be cleaned
- C11D2111/12—Soft surfaces, e.g. textile
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/37—Polymers
- C11D3/3746—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C11D3/3769—(Co)polymerised monomers containing nitrogen, e.g. carbonamides, nitriles or amines
- C11D3/3773—(Co)polymerised monomers containing nitrogen, e.g. carbonamides, nitriles or amines in liquid compositions

Definitions

the present invention relates to use of at least one cationic vinylcarboxamide/vinylamine copolymer as a color care agent for laundering, especially as a dye transfer inhibitor (DTI) and/or a dye fixation agent (DFA), to a method for preparation of liquid laundering formulations by incorporation of the at least one cationic vinylcarboxamide/vinylamine copolymer as a color care agent, and thus to liquid laundering formulations comprising at least one cationic vinylcarboxamide/vinylamine copolymer.
DTI dye transfer inhibitor
DFA dye fixation agent
Liquid detergent compositions contribute more and more proportionately to the portfolio of washing compositions for textiles today.
Liquid washing compositions comprise surfactants as a main component, including cationic, anionic, nonionic and amphoteric surfactants.
Further essential components used in liquid washing compositions are builders selected from for example polycarboxylates, and solubilizers selected from for example ethanol, glycerol or propanediol.
additional additive components are also comprised, typically in small concentrations, including different active substances such as foam regulators, graying inhibitors, soil release polymers, enzymes, optical brighteners and color care agents, such as dye transfer inhibitors and dye fixation agents.
dye molecules are often detached from colored textiles, often called as “bleeding”; these can in turn attach to other textiles, often called as “dye transferring".
color care agents such as dye transfer inhibitors (DTI) and dye fixation agents (DFA) are often used.
Dye transfer inhibitors and dye fixation agents have long been an important constituent of textile laundry detergents and cleaners of state of the art.
US 2007/0277327A1 describes detergents and cleaning agents that contain a soil-release polymer and a dye fixative selected from (a) reaction products of polyamines and cyanamides and organic and/or inorganic acids, or cyanamides and aldehydes and ammonium salts, or cyanamides and aldehydes and amines, or amines and epichlorohydrin, (b) the group containing polyamines and polyamine derivatives, (c) the group containing polyimines and polyimine derivatives, (d) the group of cationic polyelectrolytes, (e) the group containing polymers that comprise imidazoline units or (f) the group containing bis(chloromethyl)biphenyl polyquat.
a dye fixative selected from (a) reaction products of polyamines and cyanamides and organic and/or inorganic acids, or cyanamides and aldehydes and ammonium salts, or cyanamides and aldehydes and
US 2008/0103081A1 describes a liquid washing and cleaning composition
a liquid washing and cleaning composition comprising a) an anionic surfactant and d) a dye fixative selected from the group consisting of a homo- or a copolymer of diallyldimethylammonium chloride, a reaction product of cyanamides with aldehydes and ammonium salts, a reaction product of cyanamides with aldehydes and monoamines, a reaction product of monoamines and/or polyamines with epichlorohydrin, a reaction product of polyamines with cyanamides and amidosulfuric acid, and mixtures thereof.
the same dye fixative species were also proposed to be used in liquid washing and cleaning compositions in US 2008/0318830A1 , US 2008/0103080A1 , US 2009/0048137A1 and US 2008/0096788A1 .
US 2002/0193280A1 describes a laundry detergent comprising dye-transfer-inhibiting dye fixatives which are obtained by reacting a) amines with epichlorohydrin or b) cyanamide with amines and formaldehyde.
US 2003/0171249A1 describes a laundry detergent comprising dye-transfer-inhibiting dye fixatives which are obtained by reacting a) polyamines with cyanamides and amidosulfuric acid or b) cyanamides with aldehydes and ammonium salts or c) amines with epichlorohydrin.
DE 4235798A1 describes copolymers of 1-vinylpyrrolidone, 1-vinylimidazole, 1-vinylimidazolium compounds or mixtures thereof; further nitrogen-containing, basic ethylenically unsaturated monomers; and, if appropriate, other monoethylenically unsaturated monomers, and their use for inhibiting dye transfer during the washing process. Similar copolymers are described for this purpose in DE 19621509A1 and WO 98/30664A1 .
WO 2006/100246A1 describes use of cationic polycondensation products as additives for fixing colours and/or inhibiting the running of colours, for washing products and washing aftertreatment products.
the cationic polycondensation products can be produced by the condensation of (A1) non-cyclic amines obtained by the reaction of (A1a) mono(N,N-dialkylaminoalkyl)amines with (A1b) bifunctional compounds selected from the group containing urea, thiourea, dialkyl carbonates, aliphatic and aromatic dicarboxylic acids, and aliphatic and aromatic diisocyanates, in a molar ratio 1.2: 1 to 2.1: 1, or (A2) mixtures of non-cyclic amines (A1) and cyclic amines (A3) in a molar ratio 10: 1 to 1: 10 with (B) bifunctional compounds selected from the group containing alkylene di-halogenides, dihalogen alkyl ethers, halomethyl oxiran
EP 0753566A1 describes a fabric washing composition for inhibiting dye deposition, which comprises a dye deposition inhibiting polymer comprising vinyl amide monomer(s) and optionally vinyl ester monomer(s), acrylamide monomer(s) and ethylenically unsaturated monomer(s).
JP H07316590A describes a composition containing a water-soluble polymer comprising a (co)polymer of a specific amino group-containing monomer, effective for washing colored clothes and white clothes in the same bath, not requiring to select the kind of a surfactant, and not causing the problem of iron adsorption.
anionic surfactants such as linear alkylbenzenesulfonates (LAS), fatty alcohol sulfates (FAS), secondary alkanesulfonates (SAS) and in some cases also fatty alcohol ether sulfates (FAES), are basically indispensable in washing compositions due to their almost unique good washing performances.
Cationic vinylcarboxamide/vinylamine copolymers as described in the present application have never been proposed as a color care agent, especially as a dye transfer inhibitor (DTI) or a dye fixation agent (DFA), for a liquid laundry detergent formulation.
DTI dye transfer inhibitor
DFA dye fixation agent
WO 2005/026220A1 describes use of polymers containing polyvinylamine and polyvi-nylamide in order to prevent smell in dishwashers.
WO 1998/025981A1 describes a new amphiphilic graft polymer based on N-vinyl carboxamide units for use e.g. as paper strengthening agents, dispersants for pigments or plant protectants and thickeners in cosmetics.
EP 0753570A1 describes a composition useful in a washing process containing at least one vinyl amide polymer containing from 5 to 100 % by weight of at least one vinyl amide monomer and from 0 to 95 % by weight of one or more vinyl ester monomers.
the polymer is taught to be used for purpose of removing soil from an article, inhibiting soil deposition, or providing soil resistance to an article.
CH 690401A5 describes a process for fixing substantive dyes in textile industry onto cellulose-containing fibre materials comprises treating the fibre material before, during or after dyeing in a liquor containing a homo- or copolymer obtained by polymerisation of N-vinylformamide or N-vinylacetamide and optionally one or more copolymerisable monomers selected from allylamine or diallylamine derivatives, (meth)acrylic acid, maleic acid, N-vinylpyrrolidone, N-vinyl-N-methyl-formamide, N-vinyl-N-methylacetamide, N-vinyl-N-ethyl-acetamide, vinyl acetate, vinyl propionate, hydroxy-C 2 -C 4 -alkyl(meth)acrylate, (meth)acrylic acid-C 1 -C 22 -alkyl ester, (meth)acrylonitrile, (meth)acrylamide, N-mono/N,N-di-C1-C10-
US 6039768A describes a process for fixing reactive or substantive dyes on cellulosic fiber materials.
the process comprises treating the fiber before, during or after dyeing with a solution of homo- or copolymers of nitrogen-containing monomers, e.g. N-vinylforamide, N-vinylimidazole, N-vinylpyrrolidone and the like.
nitrogen-containing monomers e.g. N-vinylforamide, N-vinylimidazole, N-vinylpyrrolidone and the like.
WO 97/032477A1 describes use of polymers containing vinylamine or ethyleneimine units and optionally units from other monomers, for example N-vinyl carboxamides as biocides.
WO 95/025759A1 describes graft polymers in which monoethylenically unsaturated monomers are grafted onto the grafting base which is a polymer which contains N-vinylcarboxamides and N-vinylamines and the grafting base and use of the graft polymers as dispersants for pigments, as additives for detergents and cleaning agents, and strength agents for paper and as soil stabilizers and for fertilizer compaction.
WO 2014/148465A1 describes a cationizing agent for cationizing a cloth piror to the firm fixing of water-insoluble particles onto the cloth, the cationizing agent comprising a polymer derived from vinyl amine monomer.
WO 95/16815A1 describes a dye fixation agent for cellulosic fibers dyed with reactive dyes, comprising a homopolymer of vinylamine or a copolymer of vinylamine with diallylamine or vinyl compound.
the polymers are proposed to be used for treating cellulose fibers dyed with a reactive dye in order to improve chlorine fastness and wet fastness of cellulose fibers dyed with a reactive dye.
cationic vinylcarboxamide/vinylamine copolymers which comprise (1a) 30 to 95 mol% of vinylamine derived units, (1b) 5 to 70 mol % of vinylcarboxamide derived units and optionally (1c) 0 to 5mol % of units derived from one or more ethylenically unsaturated monomers, described in detail hereinafter.
the cationic vinylcarboxamide/vinylamine copolymers according to the present invention are well compatible with anionic surfactants in a liquid laundering formulation, which formulation is both, physically and chemically, stable at a pH from about pH 4.5 to about pH 11, and especially from about pH 7.0 to about 8.5, more preferably at a neutral pH of about 7, and without deterioration in cleaning or treatment performance of the laundering formulation.
the present invention relates to use of at least one cationic vinylcarboxamide/vinylamine copolymer according to the present invention as a color care agent, especially as a dye transfer inhibitor (DTI) and/or a dye fixation agent (DFA), in laundering formulations, especially liquid laundering formulations.
a color care agent especially as a dye transfer inhibitor (DTI) and/or a dye fixation agent (DFA)
DTI dye transfer inhibitor
DFA dye fixation agent
the cationic vinylcarboxamide/vinylamine copolymers according to the present invention also show good compatibility with anionic surfactants, especially LAS surfactants widely used in laundering formulations, which will not result in any deterioration in cleaning or caring performance of the laundering formulations.
the cationic vinylcarboxamide/vinylamine copolymers according to the present invention show a color care effect, particularly, a dye (or color) fixing effect and/or a dye transfer inhibiting effect during laundering without any deterioration in cleaning or caring performance of the laundering formulations.
the dye fixing effect refers to an effect of preventing dyes from fading out of colored textiles during laundering or reducing the amount of the dyes fading out of colored textiles during laundering.
the dye transfer inhibiting effect refers to an effect of preventing dyes fading out of darker colored textiles from transferring to lighter colored textiles during laundering.
the cationic vinylcarboxamide/vinylamine copolymer used for the purpose of the present invention is a hydrolysate of copolymers or homopolymers comprising the vinylcarboxamide derived units represented by formula (II), especially a hydrolysate of homopolymers of N-vinylformamide or N-vinylacetamide.
the cationic vinylcarboxamide/vinylamine copolymer for the purpose of the present invention is prepared and obtained from a polyvinylformamide (PVF) with a number average molecular weight M n of from 1,000 to 100,000, preferably from 3,000 to 60,000 and most preferably from 5,000 to 45,000.
PVF polyvinylformamide
it is prepared and obtained from a polyvinylformamide (PVF) with a number average molecular weight M n of less than 50,000.
the laundering formulations according to the present invention comprise in addition to the cationic vinylcarboxamide/vinylamine copolymer of the present invention at least one anionic surfactant.
anionic surfactant is selected from linear alkylbenzenesulfonate anionic surfactants.
the present invention also comprises methods for preparing such laundering formulations by incorporating such anionic surfactant, especially linear alkylbenzenesulfonate anionic surfactants.
the laundering formulations according to the present invention show good compatibility anionic surfactants at a pH from about pH 4.0 to about pH 11.0, and especially preferably from about pH 7.0 to about pH 8.5.
the cationic vinylcarboxamide/vinylamine copolymers for the purpose of the present invention can be applied as dye transfer inhibitor agents in laundering formulations and/or as dye fixation agents in laundering formulations.
the present invention also relates to methods for preparing laundering formulations, especially liquid laundering formulations, by incorporating at least one cationic vinylcarboxamide/vinylamine copolymer of the present invention as a color care agents, acting as dye transfer inhibitor and/or as dye fixation agent.
the present invention relates to use of at least one cationic vinylcarboxamide/vinylamine copolymer as a color care agent in laundering formulations, particularly liquid laundering formulations.
the expression “the cationic vinylcarboxamide/vinylamine copolymer(s) according to the present invention” or “the cationic copolymer(s) according to the present invention” or “the vinylcarboxamide/vinylamine copolymer(s) according to the present invention” or the “cationic vinylcarboxamide/vinylamine copolymer(s)” are used.
the terms used for the cationic vinylcarboxamide/vinylamine copolymer(s) according to the present invention may be interpreted with the single meaning of one "copolymer” as well as with the plural meaning of more than one "copolymers”. It is to be understood that the cationic vinylcarboxamide/vinylamine copolymer(s) may optionally be at least partly in form of salt with any suitable counterions. Counterions that may be present in the salt are not particularly limited.
Suitable counterions are for example, but not limited to, halide anions such as chloride, bromide, iodide anions, as well as polyatomic anions, such as chlorate, chlorite, hypochlorite, sulfate, sulfonate, hydroxide, hydrogen sulfate, hydrogen bisulfate, sulfide, sulfite, phosphate, hydrogen phosphate, dihydrogen phosphate, phosphonate, nitride, nitrite, nitrate, carbonate, hydrogen carbonate, hydrogen bicarbonate, acetate anions.
halide anions such as chloride, bromide, iodide anions
polyatomic anions such as chlorate, chlorite, hypochlorite, sulfate, sulfonate, hydroxide, hydrogen sulfate, hydrogen bisulfate, sulfide, sulfite, phosphate, hydrogen phosphate, dihydrogen
the cationic vinylcarboxamide/vinylamine copolymers of a number average molecular weight (Mn) of up to 400,000 g/mol useful as a color care agent in laundering formulations comprise
nitrogen atoms in the units represented by formula (I) and formula (II) may be in form of ammonium salt with suitable anions which are not shown in the formulae.
suitable counterions are for example, but not limited to, halide anions such as chloride anion, sulfate anion and sulfonate anions.
alkyl comprises straight-chain or branched alkyl groups, in particular C 1 -C 6 -alkyl.
C 1 -C 6 -alkyl are methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, neo-pentyl, n-hexyl, and position isomers thereof.
any co-monomers having an ethylenically unsaturated bond can be used.
the ethylenically unsaturated co-monomers from which units (1c) are derived may be nitrogenous monomers polymerizable via vinyl or allyl groups, for example N-vinylpyrrolidone, N-vinylimidazole, N-vinylcaprolactam, 4-vinylpyridine, N-vinylpyridine, diallyldimethylammonium chloride, allylamine, (meth)acrylamide, N-substituted and N,N-substituted (meth)acrylamide.
R-OH C 1 -C 18 -alkyl, benzyl, ethylphenyl, cyclohexy
the cationic vinylcarboxamide/vinylamine copolymers according to the present invention comprises
the cationic vinylcarboxamide/vinylamine copolymers according to the present invention consist of (1a) 30 to 95 mol% of vinylamine derived units represented by formula (I), and (1 b) 5 to 70 mol % of vinylcarboxamide derived units represented by formula (II), wherein the unit described under (1c) hereinabove is not present and the formula (I) and formula (II) are as described hereinabove, provided that if the M n is below 25,000 g/mol, the content of unit (1a) is equal to or higher than 40 mol%, and if the M n is equal to or above 25,000 g/mol, the content of unit (1 a) is equal to or less than 80 mol%.
the cationic vinylcarboxamide/vinylamine copolymers according to the present invention consist of (1a) 40 to 80 mol% of vinylamine derived units represented by formula (I), and (1 b) 20 to 60 mol % of vinylcarboxamide derived units represented by formula (II), wherein the unit described under (1c) hereinabove is not present and the formula (I) and formula (II) are as described hereinabove.
both R 1 in formula (I) and R 3 in formula (II) are H. Additionally or alternatively, both R 2 in formula (I) and R 5 in formula (II) are H. Additionally or alternatively, R 4 in formula (II) is preferably H or methyl. In a preferred embodiment, both R 1 in formula (I) and R 3 in formula (II) are H and both R 2 in formula (I) and R 5 in formula (II) are H. In a more preferred embodiment, both R 1 in formula (I) and R 3 in formula (II) are H, both R 2 in formula (I) and R 5 in formula (II) are H, and R 4 in formula (II) is H.
the cationic vinylcarboxamide/vinylamine copolymers according to the present invention have a number average molecular weight (M n ) of up to 400,000.
the cationic vinylcarboxamide/vinylamine copolymers according to the present invention have a number average molecular weight (M n ) of preferably of from 1,000 to 100,000.
the cationic vinylcarboxamide/vinylamine copolymers according to the present invention have a number average molecular weight (M n ) of more preferably from 3,000 to 60,000.
the cationic vinylcarboxamide/vinylamine copolymers according to the present invention have a number average molecular weight (M n ) of most preferably of less than 50,000.
the cationic vinylcarboxamide/vinylamine copolymers according to the present invention have a number average molecular weight (M n ) of from 5,000 to 45,000.
the cationic vinylcarboxamide/vinylamine copolymers according to the present invention preferably have a dispersity PDI (M w /M n ) in the range from 1.1 to 4.0, more preferably from 2.0 to 3.0.
the cationic vinylcarboxamide/vinylamine copolymers according to the present invention are hydrolysates of copolymers or homopolymers comprising the vinylcarboxamide derived units represented by formula (II) which is as described hereinabove.
the cationic vinylcarboxamide/vinylamine copolymers according to the present invention are hydrolysates of homopolymers of N-vinylformamide or N-vinylacetamide.
the hydrolysis degree of the copolymers is equal to or higher than 40 mol% if the M n is below 25,000 g/mol, and the hydrolysis degree of the copolymers is equal to or less than 80 mol% if the M n is equal to or above 25,000 g/mol.
the cationic vinylcarboxamide/vinylamine copolymers according to the present invention are obtainable or obtained by polymerization of monomers from which the units (1a), (1b) and (1c) are derived.
the monomers are selected from substituted or non-substituted N-vinylcarboxamides from which both units (1a) and (1b) are derived by hydrolysis.
the cationic vinylcarboxamide/vinylamine copolymers according to the present invention can be prepared by a process which comprises
the units (1a) and units (1b) contained in the cationic vinylcarboxamide/vinylamine copolymers according to the present invention are both derived from the N-vinylcarboxamide monomer of formula (III).
the units (1a) are derived from the N-vinylcarboxamide monomer of formula (III) through polymerization thereof and subsequent hydrolysis.
Suitable ethylenically unsaturated co-monomers for the polymerization are as described hereinabove for the ethylenically unsaturated co-monomers from which units (1c) are derived.
the polymerization of the monomers in the process for preparing the cationic vinylcarboxamide/vinylamine copolymers is not particularly limited, and various known polymerization methods can be applied, for example but not limited to, bulk polymerization, solution polymerization, suspension polymerization, emulsion polymerization and the like, e.g. as described in Principles of Polymerization, G. Odian, 4th Ed. (2004), Wiley, New jersey .
radical polymerization initiator a redox initiator, azo initiator, peroxide, etc.
Polymerization can be carried out continuously or batchwise.
the polymerization can optionally be initiated solely by the action of energy-rich radiation, e.g. electron beams or UV rays.
energy-rich radiation e.g. electron beams or UV rays.
an amount of from 0.01 to 20% by weight, preferably 0.05 to 5% by weight, based on the monomers can be applied.
the polymerization can be carried out in the presence or absence of inert solvents or diluents. Since polymerization in the absence of inert solvents or diluents usually leads to inhomogeneous polymers, polymerization in an inert solvent or diluent is preferred.
Suitable inert diluents are, for example, those in which the N-vinylcarboxamides are soluble, for example, methanol, ethanol, isopropanol, n-propanol, n-butanol, sec-butanol, tetrahydrofuran, dioxane, water and any mixtures thereof.
the polymerization of the monomers is customarily carried out in an inert gas atmosphere with exclusion of atmospheric oxygen.
the monomers can be copolymerized batchwise by heating the reaction mixture to the polymerization temperature and then allowing the reaction to proceed. In this case, these temperatures are in the range from 40 to 180 °C.
the polymerization can be carried out under normal pressure (i.e. about 1.0 bar), reduced pressure (for example, about 0.5 bar) or elevated pressure (for example, about 2 bar).
the aqueous solution is preferably adjusted to a pH in the range of from 4 to 9, in particular from 5 to 8. In many cases, it is recommended to carry out the polymerization in the presence of buffers, e.g. to add primary or secondary sodium phosphate to the aqueous phase.
the hydrolysis to partially remove the group -COR 4 from the obtained polymers is preferably carried out in the presence of water under the action of acids, bases or enzymes.
a strong acid such as hydrochloric acid or sulfuric acid is preferable.
the pH is in the range of from 0 to 5.
a strong base such as sodium hydroxide, potassium hydroxide or ammonia is preferable.
the pH is in the range of from 8 to 14.
the acid or base is generally used in an amount of from 0.05 to 1.5 equivalents, preferably of from 0.4 to 1.2 equivalents, per acyl group equivalent in the cationic vinylcarboxamide/vinylamine copolymers according to the present invention.
Hydrolysis in the presence of acid or base is carried out, for example, at a temperature in the range of 30 to 170 °C or, preferably 50 to 120 °C.
the reaction time differs depending on temperature, which however is normally about 2 to 8, preferably 3 to 5 hours.
a procedure has proven particularly suitable in which, for hydrolysis, the bases or acids are added in aqueous solution.
neutralization is preferably carried out such that the pH of the hydrolyzed polymer solution is in the range of from 2 to 8, preferably 3 to 7, in order to obtain the desired hydrolysis degree, that is relative to the contents of the units (1a) and the units (1b).
the hydrolysis can also be carried out with the aid of enzymes.
the degree of hydrolysis of the polymers can easily be determined analytically by conventional methods known in the art.
the preparation of the cationic vinylcarboxamide/vinylamine copolymers is not limited to the above process.
the cationic vinylcarboxamide/vinylamine copolymers can also be prepared by any other processes known in the art, for example, deriving the units (1a) from arylamide monomers through polymerization and Hoffman reaction as described in EP 2977 507A1 .
the cationic vinylcarboxamide/vinylamine copolymers according to the present invention can be used generally in all types of formulations for laundering, for example, various detergents such as laundry detergents, especially color care detergents, heavy-duty detergents, mild detergents, specialty detergents for black textiles, detergents for jeans, and wool detergents, or laundry after-treatment formulations.
various detergents such as laundry detergents, especially color care detergents, heavy-duty detergents, mild detergents, specialty detergents for black textiles, detergents for jeans, and wool detergents, or laundry after-treatment formulations.
the laundering formulations in which the cationic vinylcarboxamide/vinylamine copolymers according to the present invention can be used in semi-liquid form or in liquid form, but most preferably in liquid form.
the cationic vinylcarboxamide/vinylamine copolymers according to the present invention may be used in a laundering formulation in a conventional amount known in the art for a dye transfer inhibitor or a dye fixation agent.
the cationic vinylcarboxamide/vinylamine copolymers are used in an amount of from 0.01 % to 20.0 % by weight, preferably from 0.05 to 10.0 % by weight, particularly from 0.05 % to 5.0 % by weight and especially from 0.1 % to 2.0 % by weight, based on the total weight of the formulation.
the laundry detergent formulations, after-treatment formulations and the like may have any known compositions in the field of laundering and may contain in addition to or in place of conventional care color agents, such as dye transfer inhibitors or dye fixation agents, the cationic vinylcarboxamide/vinylamine copolymers according to the present invention as a color care agent.
conventional care color agents such as dye transfer inhibitors or dye fixation agents, the cationic vinylcarboxamide/vinylamine copolymers according to the present invention as a color care agent.
liquid laundry detergent formulations may comprise following components:
laundry care rinse formulations in particular laundry care rinse formulations generally comprise
Suitable nonionic surfactants include, for example:
Suitable anionic surfactants include, for example:
the anionic surfactants are preferably added to the laundry formulations in the form of salts.
Suitable salts are, for example, alkali metal salts, such as sodium, potassium and lithium salts, and ammonium salts, such as hydroxyethylammonium, di(hydroxyethyl)ammonium and tri(hydroxyethyl)ammonium salts.
Suitable cationic surfactants include, for example:
Amphoteric surfactants may also be used in the laundry formulations, for example, alkylbetaines, alkylamidobetaines, aminopropionates, aminoglycinates and amphoteric imidazolium compounds.
cationic vinylcarboxamide/vinylamine copolymers according to the present invention are notable especially in those detergent formulations which comprise only anionic surfactants as surface active compounds or a major fraction of anionic surfactants, especially linear alkylbenzenesulfonates (LAS) anionic surfactants.
anionic surfactants especially anionic surfactants as surface active compounds or a major fraction of anionic surfactants, especially linear alkylbenzenesulfonates (LAS) anionic surfactants.
LAS linear alkylbenzenesulfonates
a detergent formulation comprising the cationic vinylcarboxamide/vinylamine copolymers according to the present invention may contain a total of 0.5 to 70% % by weight of surfactants.
the total percentage of surfactants ranges from 10 to 40 % by weight in a detergent formulation according to the present invention.
a higher ratio of anionic surfactant can be incorporated into the final detergent formulation without affecting the compatibility of the components. For instance, a fraction of anionic surfactants of up to 90 % by weight, based on the total amount of surfactants in the laundering formulation, may be tolerated without negative impact on the formulation. In case the anionic surfactants are linear alkylbenzenesulfonates (LAS), a total a fraction of up to 25 % by weight, based on the total amount of surfactants in the laundering formulation, may still result in stable formulations.
LAS linear alkylbenzenesulfonates
Suitable organic builders include, for example:
Suitable graying inhibitors are, for example, carboxymethylcellulose and graft polymers of vinyl acetate onto polyethylene glycols.
Suitable bleaches are, for example, adducts of hydrogen peroxide onto inorganic salts, such as sodium perboratemonohydrate, sodium perboratetetrahydrate and sodium carbonate perhydrate, and percarboxylic acids, such as phthalimidopercaproic acid.
inorganic salts such as sodium perboratemonohydrate, sodium perboratetetrahydrate and sodium carbonate perhydrate
percarboxylic acids such as phthalimidopercaproic acid.
Suitable bleach activators are, for example, N,N,N',N'-tetraacetylethylenediamine (TAED), sodium p-nonanoyloxybenzenesulfonate and N-methylmorpholinium acetonitrile methyl sulfate.
TAED N,N,N',N'-tetraacetylethylenediamine
sodium p-nonanoyloxybenzenesulfonate sodium p-nonanoyloxybenzenesulfonate
N-methylmorpholinium acetonitrile methyl sulfate N,N,N',N'-tetraacetylethylenediamine
Enzymes preferably used in detergents are proteases, lipases, amylases, cellulases, oxidases and peroxidases.
Suitable further dye transfer inhibitors include, for example, homopolymers, copolymers and graft polymers of 1-vinylpyrrolidone, 1-vinylimidazole or 4-vinylpyridine N-oxide. Homopolymers and copolymers of 4-vinylpyridine reacted with chloroacetic acid are also suitable as dye transfer inhibitors.
Such dye transfer inhibitors are commercially available, for example polyvinylpyrrolidones, vinylpyrrolidone-vinylimidazole copolymers, poly(4-vinylpyridine N-oxides) or poly(4-vinylpyridine N-carboxymethyl)betaines.
Detergent ingredients are otherwise generally known. Detailed descriptions can be found, for example, in Liquid Detergents, Editor: Kuo-Yann Lai, Surfactant Sci. Ser., Vol. 67, Marcel Decker, New York, 1997, p. 272-304 or in patent (application) publications such as WO 99/06524A1 .
the incorporation of the cationic vinylcarboxamide/vinylamine copolymers according to the present invention into the respective formulations can be carried out in a manner known per se, the cationic vinylcarboxamide/vinylamine copolymers often being used in liquid form, i.e. dissolved or dispersed form.
the cationic vinylcarboxamide/vinylamine copolymers can also be used in powder or granule form.
the present invention relates to a method for preparation of a laundering formulation, especially a liquid laundering formulation by incorporation of the cationic vinylcarboxamide/vinylamine copolymers according to the present invention, as a color care agent. More particularly, the cationic vinylcarboxamide/vinylamine copolymers according to the present invention functions as dye transfer inhibitor agent or dye fixation agent in the prepared laundering formulations.
liquid laundering formulation is intended to include any fluid forms of formulation, including liquid and semi-liquid formulations, for example liquids, gels and pastes.
the cationic vinylcarboxamide/vinylamine copolymers according to the present invention are mixed with surfactants such as nonionic, anionic and/or cationic surfactants and other conventional ingredients for a laundering formulation, in a solvent, preferably water.
the other conventional ingredients include, for example but not limited to, organic builder, enzymes, perfume, complexing agents, corrosion inhibitors, amphoteric surfactants, bleaches, bleach activators, bleach catalysts, further color protection additives and dye transfer inhibitors, graying inhibitors, soil release polyesters, fiber protection additives, silicones, dyes, bactericides and preservatives, organic solvents, solubility promoters, hydrotropes, foam regulators, thickeners and/or alkanolamines.
organic builder enzymes, perfume, complexing agents, corrosion inhibitors, amphoteric surfactants, bleaches, bleach activators, bleach catalysts, further color protection additives and dye transfer inhibitors, graying inhibitors, soil release polyesters, fiber protection additives, silicones, dyes, bactericides and preservatives, organic solvents, solubility promoters, hydrotropes, foam regulators, thickeners and/or alkanolamines.
laundering is intended to comprise washing, rinsing, after-treatment and any other possible operations for laundry.
laundering formulations comprise any formulations that may be used during laundering methods, for example, washing, rinsing, after-treatment and the like.
the present invention further relates to a method for color care of colored textiles during laundering, wherein the cationic vinylformamide/vinylamine copolymers according to the present invention are brought into contact with the textiles.
the present invention relates to a method for fixing dyes on colored textiles during laundering, wherein the cationic vinylformamide/vinylamine copolymers according to the present invention are brought into contact with the textiles.
the present invention relates to a method for preventing and inhibiting dye transfer from colored textiles to white or lighter colored textiles during laundering, wherein the cationic vinylformamide/vinylamine copolymers according to the present invention are brought into contact with the textiles.
the methods for color care of colored textiles during laundering according to the present invention can be applied to textiles of various sources, for example, cotton, linen, silk and synthetic fiber materials, preferably to textiles of cotton and cotton blends.
the colored textiles that can be treated by the method for color care according to the present invention are preferably those colored with reactive dyes or direct dyes.
the colored textiles that can be treated by the method for color care according to the present invention, are for example dyed with direct dyes selected from, including but not limited to, C.I. Direct Yellow 11, C.I. Direct Yellow 12, C.I. Direct Orange 26, C.I. Direct Orange 39, C.I. Direct Red 23, C.I. Direct Red 28, C.I. Direct Red 31, C.I. Direct Red 13, C.I. Direct Red 83.1 C.I. Direct Red 227, C.I. Direct Green 6, C.I. Direct Green 26, C.I. Direct Blue 6, C.I. Direct Blue 15, C.I. Direct Blue 71, C.I. Direct Blue 151, C.I. Direct brown 1, C.I. Direct Brown 2, C.I. Direct Brown MM, C.I. Direct Brown RN, C.I. Direct Violet 66, C.I. Direct Black 38, C.I. Direct Black 19, C.I. Direct Black 22, C.I. Direct Black 168 or C.I. Direct Black 17.
direct dyes selected from, including but not limited to, C.I
the colored textiles that can be treated by the method for color care according to the present invention, are for example dyed with reactive dyes selected from, including but not limited to, C.I. Reactive Yellow 2, C.I. Reactive Yellow 125, C.I. Reactive Yellow 158, C.I. Reactive Yellow 14, C.I. Reactive Red 1, C.I. Reactive Red 120, C.I. Reactive Red 241, C.I. Reactive Red 158, C.I. Reactive Red 35, C.I. Reactive Green 6, C.I. Reactive Green 8, C.I. Reactive Blue 19, C.I. Reactive Blue 181, C.I. Reactive Blue 162, C.I. Reactive Blue 221, C.I. Reactive Orange 5, C.I. Reactive Orange 13, C.I.
reactive dyes selected from, including but not limited to, C.I. Reactive Yellow 2, C.I. Reactive Yellow 125, C.I. Reactive Yellow 158, C.I. Reactive Yellow 14, C.I. Reactive Red 1, C.I. Reactive
Reactive Orange 127 C.I. Reactive Orange 122, C.I. Reactive Brown 11, C.I. Reactive Brown 23, C.I. Reactive Brown 7, C.I. Reactive Violet 4, C.I. Reactive Violet 33, C.I. Reactive Violet 12, C.I. Reactive Black 8, C.I. Reactive Black 5 or C.I. Reactive Black 11.
CVVC cationic vinylcarboxamide/vinylamine copolymers
a 35% wt. aqueous solution of polyvinylformamide (PVF) with a number average molecular weight M n as specified Table 1, at pH of 8.0 and a density of 1.1 g/cm 3 was placed inside a Systag FlexyCuybe automated glass reactor and heated under stirring at 200 rpm. After temperature equilibration at 80°C, 40% wt. aqueous sodium bisulfite and/or 50% wt. aqueous NaOH solutions in amounts as specified in Table 1 as vinylformamide (VFA) equivalents were fed inside the reactor within 1 h. The hydrolysis reaction was left to proceed for the time as specified in Table 1, after which the reactor was rapidly cooled down to room temperature.
PVF polyvinylformamide
reaction time [h] Degree of hydrolysis, [mol%] CVVC 3 10,000 8,300 0 0.8 6.0 43 CVVC 4 10,000 7,900 0 0.8 4.5 54 CVVC 5 10,000 7,200 0.02 0.8 3.0 70 CVVC 6 10,000 6,300 0.02 1.05 6.0 95 CVVC 8 45,000 39,700 0.02 0.35 3.0 30 CVVC 9 45,000 32,600 0.02 0.8 3.0 70 CVVC 10 45,000 30,800 0 1.1 4.0 80 CVVC 12 400,000 352,700 0.02 0.35 3.0 30
Comparative vinylcarboxamide/vinylamine copolymers were prepared according to the preparation method described hereinabove and under the conditions and parameters as specified in the respective lines of Tables 2.1 and 2.2.
Table 2.1 Parameters for Comparative CVVCs showing no color care effect Copolymers Number average molecular weight (M n ) [g/mol] of starting PVF Number average molecular weight (M n ) [g/mol] of final Copolymers (calculated) NaHSO 3 solution, VFA eq. NaOH solution, VFA eq.
the number average molecular weights of the starting polyvinylformamide (PVF) for preparing cationic vinylcarboxamide/vinylamine copolymers CVVC 1 to CVVC 13 as shown above were determined by Size-Exclusion Chromatography (SEC), using an Agilent 1200 chromatograph, equipped with a binary pump, a refractive index detector and a PSS Novema Max Ultrahigh analytical column.
SEC Size-Exclusion Chromatography
Poly(2-vinylpyridine) was used as standard and water comprising 0.1 w/w% trifluorace-tic acid and 0.1 mol/l NaCl was used as effluent under following conditions:
the hydrolysis degrees of the cationic vinylcarboxamide/vinylamine copolymers CVVC 1 to CVVC 13 as prepared above according to Tables 1, 2.1 and 2.2 were determined by the ratio of the peak area of the released formic acid protons over the sum of the peak areas of the released formic acid protons plus the unhydrolyzed formyl protons as measured by 1 H NMR.
the number average molecular weight of the final copolymers after hydrolysis was estimated and calculated based on the weight of the leaving formyl groups and the weight of protons combined that correspond to the respective degree of hydrolysis. Specifically, the corresponding weight of the formyl groups released during hydrolysis was subtracted, while the corresponding weight of the protons combined during hydrolysis was added to the number average molecular weight of the polymer before hydrolysis.
dyed textile samples also called dye bleeders
the textiles were instrumentally assessed with a Datacolor reflection spectrometer Model Type ELREPHO before and after washing. From the reflection data readings L*, a*, b*, Y were derived and further expressed in ⁇ E and ⁇ Y values.
⁇ E is adopted as conventionally used in the art.
the values L* initial , a* initial , and b* initial are measured on white acceptor textile before washing.
the values L* washed , a* washed and b* washed are measured on the white acceptor textile after washing. Standard colorimetric measurement was used to obtain L*, a* and b* values.
⁇ Y Y washed ⁇ Y initial
Dye bleeder 1 Linear alkyl benzene sulfonate 2 Alkyl ether sulfate 3 Alkyl ether ethoxylate (7 EO) CVVC 5 ⁇ Y of Empa 130 (Direct Red 83.1) ⁇ Y of Empa 133 (Direct Blue 71) 1 0 0 0 0 1.36 0.80 2 0 0 0 0.025 0.04 0.54 3 1 0 0 0 1.23 1.57 4 1 0 0 0.025 1.16 1.12 5 0 1 0 0 1.34 1.55 6 0 1 0 0.025 1.11 1.22 7 0 0 1 0 0.87 0.98 8 0 0 1 0.025 -0.14* 0.60 * ⁇ Y with a negative value represents darker in color.
solutions containing CCVC 5 copolymer according to the present invention show a lower ⁇ Y value of the dye bleeder compared to solutions without the inventive copolymers respectively, thereby demonstrating a better dye fixation performance in presence of the CCV5 copolymer of the present invention for each solution.
dye bleeder (2 g) and white acceptor textiles (18 g) were washed with 200 ml washing solutions prepared from water with a hardness of 250 ppm and 3.25 g/L of a detergent of a model formulation (specified above) to which 0.5 % by weight of color care agent based on the weight of the detergent has been added, at 40°C for 30 min. After washing, the textiles were rinsed with tap water and dried at 37°C in an oven.
SDL ATLAS Launder-Ometer
Compatibility of the cationic vinylcarboxamide/vinylamine copolymers according to the present invention with anionic surfactants is demonstrated under different concentrations such as 15 wt% as shown in Table 10 and up to 24 wt% as shown in Table 9.
the results in Table 11 show compatibility of the cationic vinylcarboxamide/vinylamine copolymers according to the present invention in liquid detergent of various model formulations, thereby demonstrating the cationic vinylcarboxamide/vinylamine copolymers according to the present invention can be applied widely in liquid detergent formulations, expecially those containing an anionic surfactant.

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EP17177768.3A 2017-06-26 2017-06-26 Utilisation de copolymères vinylamine/vinylcarboxamide cationiques comme agent de protection des couleurs pour formulations de blanchissage Withdrawn EP3421583A1 (fr)

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