WO2004042136A1 - Lineare polyamino- und/oder polyammonium-polysiloxancopolymere ii - Google Patents
Lineare polyamino- und/oder polyammonium-polysiloxancopolymere ii Download PDFInfo
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- WO2004042136A1 WO2004042136A1 PCT/EP2003/050773 EP0350773W WO2004042136A1 WO 2004042136 A1 WO2004042136 A1 WO 2004042136A1 EP 0350773 W EP0350773 W EP 0350773W WO 2004042136 A1 WO2004042136 A1 WO 2004042136A1
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- quaternized
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- -1 polysiloxane copolymers Polymers 0.000 title claims abstract description 134
- 229920001296 polysiloxane Polymers 0.000 title claims abstract description 61
- 239000000203 mixture Substances 0.000 claims abstract description 32
- 238000009472 formulation Methods 0.000 claims abstract description 12
- 239000002537 cosmetic Substances 0.000 claims abstract description 9
- 239000000758 substrate Substances 0.000 claims abstract description 3
- 238000004381 surface treatment Methods 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 36
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 25
- 239000000178 monomer Substances 0.000 claims description 20
- 229920006395 saturated elastomer Polymers 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 125000004122 cyclic group Chemical group 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 125000000623 heterocyclic group Chemical group 0.000 claims description 14
- 150000002894 organic compounds Chemical class 0.000 claims description 11
- 125000004193 piperazinyl group Chemical group 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000003700 epoxy group Chemical group 0.000 claims description 9
- 239000000835 fiber Substances 0.000 claims description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 8
- 239000003599 detergent Substances 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- 229920000570 polyether Polymers 0.000 claims description 8
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000002883 imidazolyl group Chemical group 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 125000004185 ester group Chemical group 0.000 claims description 4
- 125000000524 functional group Chemical group 0.000 claims description 4
- 125000001188 haloalkyl group Chemical group 0.000 claims description 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 239000004615 ingredient Substances 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 125000004001 thioalkyl group Chemical group 0.000 claims description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 2
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 238000005406 washing Methods 0.000 abstract description 6
- 239000003795 chemical substances by application Substances 0.000 abstract description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 18
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 14
- 239000004753 textile Substances 0.000 description 14
- 150000004985 diamines Chemical class 0.000 description 13
- 125000001453 quaternary ammonium group Chemical group 0.000 description 13
- 125000003277 amino group Chemical group 0.000 description 11
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
- 239000004014 plasticizer Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 125000002947 alkylene group Chemical group 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 8
- 101150065749 Churc1 gene Proteins 0.000 description 8
- 102100038239 Protein Churchill Human genes 0.000 description 8
- 238000005956 quaternization reaction Methods 0.000 description 8
- 239000012048 reactive intermediate Substances 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 125000001302 tertiary amino group Chemical group 0.000 description 6
- 239000004593 Epoxy Substances 0.000 description 5
- 230000029936 alkylation Effects 0.000 description 5
- 238000005804 alkylation reaction Methods 0.000 description 5
- 239000003945 anionic surfactant Substances 0.000 description 5
- 238000006459 hydrosilylation reaction Methods 0.000 description 5
- 239000000123 paper Substances 0.000 description 5
- 150000003335 secondary amines Chemical class 0.000 description 5
- 0 C**1(C)CC*(C)(*)CC1 Chemical compound C**1(C)CC*(C)(*)CC1 0.000 description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 4
- 150000002118 epoxides Chemical class 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexamethylene diamine Natural products NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 4
- TXXWBTOATXBWDR-UHFFFAOYSA-N n,n,n',n'-tetramethylhexane-1,6-diamine Chemical compound CN(C)CCCCCCN(C)C TXXWBTOATXBWDR-UHFFFAOYSA-N 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 150000003512 tertiary amines Chemical class 0.000 description 4
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000013459 approach Methods 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- RXYPXQSKLGGKOL-UHFFFAOYSA-N 1,4-dimethylpiperazine Chemical compound CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 description 2
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 2
- KDHWOCLBMVSZPG-UHFFFAOYSA-N 3-imidazol-1-ylpropan-1-amine Chemical compound NCCCN1C=CN=C1 KDHWOCLBMVSZPG-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical group CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 125000004450 alkenylene group Chemical group 0.000 description 2
- 125000004419 alkynylene group Chemical group 0.000 description 2
- 150000007942 carboxylates Chemical class 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000010276 construction Methods 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 125000004427 diamine group Chemical group 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 125000005270 trialkylamine group Chemical group 0.000 description 2
- QLAJNZSPVITUCQ-UHFFFAOYSA-N 1,3,2-dioxathietane 2,2-dioxide Chemical compound O=S1(=O)OCO1 QLAJNZSPVITUCQ-UHFFFAOYSA-N 0.000 description 1
- ZZHIDJWUJRKHGX-UHFFFAOYSA-N 1,4-bis(chloromethyl)benzene Chemical compound ClCC1=CC=C(CCl)C=C1 ZZHIDJWUJRKHGX-UHFFFAOYSA-N 0.000 description 1
- UWFRVQVNYNPBEF-UHFFFAOYSA-N 1-(2,4-dimethylphenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(C)C=C1C UWFRVQVNYNPBEF-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical class CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 1
- NWLUZGJDEZBBRH-UHFFFAOYSA-N 2-(propan-2-yloxymethyl)oxirane Chemical compound CC(C)OCC1CO1 NWLUZGJDEZBBRH-UHFFFAOYSA-N 0.000 description 1
- SEFYJVFBMNOLBK-UHFFFAOYSA-N 2-[2-[2-(oxiran-2-ylmethoxy)ethoxy]ethoxymethyl]oxirane Chemical compound C1OC1COCCOCCOCC1CO1 SEFYJVFBMNOLBK-UHFFFAOYSA-N 0.000 description 1
- KUAUJXBLDYVELT-UHFFFAOYSA-N 2-[[2,2-dimethyl-3-(oxiran-2-ylmethoxy)propoxy]methyl]oxirane Chemical compound C1OC1COCC(C)(C)COCC1CO1 KUAUJXBLDYVELT-UHFFFAOYSA-N 0.000 description 1
- PUAQLLVFLMYYJJ-UHFFFAOYSA-N 2-aminopropiophenone Chemical group CC(N)C(=O)C1=CC=CC=C1 PUAQLLVFLMYYJJ-UHFFFAOYSA-N 0.000 description 1
- WOYWLLHHWAMFCB-UHFFFAOYSA-N 2-ethylhexyl acetate Chemical compound CCCCC(CC)COC(C)=O WOYWLLHHWAMFCB-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- XAYDWGMOPRHLEP-UHFFFAOYSA-N 6-ethenyl-7-oxabicyclo[4.1.0]heptane Chemical compound C1CCCC2OC21C=C XAYDWGMOPRHLEP-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- PHOQVHQSTUBQQK-SQOUGZDYSA-N D-glucono-1,5-lactone Chemical compound OC[C@H]1OC(=O)[C@H](O)[C@@H](O)[C@@H]1O PHOQVHQSTUBQQK-SQOUGZDYSA-N 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical class NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
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- 230000004913 activation Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
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- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
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- 230000033228 biological regulation Effects 0.000 description 1
- 239000007844 bleaching agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
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- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
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- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 1
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- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
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- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 1
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 1
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- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 1
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- 230000002349 favourable effect Effects 0.000 description 1
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- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
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- GKQPCPXONLDCMU-CCEZHUSRSA-N lacidipine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1C1=CC=CC=C1\C=C\C(=O)OC(C)(C)C GKQPCPXONLDCMU-CCEZHUSRSA-N 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- KBUZAJFRQCPULI-UHFFFAOYSA-N lead;1h-pyrazole Chemical compound [Pb].C=1C=NNC=1 KBUZAJFRQCPULI-UHFFFAOYSA-N 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- VEAZEPMQWHPHAG-UHFFFAOYSA-N n,n,n',n'-tetramethylbutane-1,4-diamine Chemical compound CN(C)CCCCN(C)C VEAZEPMQWHPHAG-UHFFFAOYSA-N 0.000 description 1
- GBCKRQRXNXQQPW-UHFFFAOYSA-N n,n-dimethylprop-2-en-1-amine Chemical compound CN(C)CC=C GBCKRQRXNXQQPW-UHFFFAOYSA-N 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- SBOJXQVPLKSXOG-UHFFFAOYSA-N o-amino-hydroxylamine Chemical group NON SBOJXQVPLKSXOG-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-M octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC([O-])=O QIQXTHQIDYTFRH-UHFFFAOYSA-M 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-M oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC([O-])=O ZQPPMHVWECSIRJ-KTKRTIGZSA-M 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- 238000009896 oxidative bleaching Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920006294 polydialkylsiloxane Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 125000003186 propargylic group Chemical group 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- TUNFSRHWOTWDNC-UHFFFAOYSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000009988 textile finishing Methods 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 125000000725 trifluoropropyl group Chemical group [H]C([H])(*)C([H])([H])C(F)(F)F 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
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/643—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
- A61K8/89—Polysiloxanes
- A61K8/896—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate
- A61K8/898—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate containing nitrogen, e.g. amodimethicone, trimethyl silyl amodimethicone or dimethicone propyl PG-betaine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/38—Polysiloxanes modified by chemical after-treatment
- C08G77/382—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon
- C08G77/388—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon containing nitrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/42—Block-or graft-polymers containing polysiloxane sequences
- C08G77/452—Block-or graft-polymers containing polysiloxane sequences containing nitrogen-containing sequences
-
- 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
- C11D3/3703—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C11D3/373—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicones
- C11D3/3742—Nitrogen containing silicones
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/02—Preparations for cleaning the hair
Definitions
- the invention relates to linear polyamino and / or polyammonium polysiloxane copolymers, in particular hydrophilic polyquaternary
- Polysiloxane copolymers and their use as washable hydrophilic plasticizers Polysiloxanes containing amino groups are known as textile plasticizers (EP 441530).
- textile plasticizers EP 441530.
- the introduction of amino structures modified by ethylene oxide / propylene oxide units as side chains brings about an improvement in the effect (US Pat. No. 5,591,880, US Pat. No. 5,650,529).
- the alkylene oxide units allow the targeted adjustment of the hydrophilic-hydrophobic balance. From the synthetic point of view, disadvantage is the difficult esterification of amino alcohols with siloxane-linked carboxylic acid groups, which is included in the synthesis strategy, and the general comb structure of the products with regard to the softening properties.
- polysiloxanes are polydiorganosiloxane-polyalkylammonium compounds
- the quaternary ammonium structure is introduced via the silane, the quaternary nitrogen atom being substituted by alkylene Strictly comb-like alkylene oxide-modified polysiloxane tranquates have also been described (US Pat. No. 5,098,979).
- No. 6,242,554 describes ⁇ , co-difunctional siloxane derivatives, each of which has a separate quaternary ammonium and alkylene oxide unit. These materials are characterized by improved compatibility with polar environments.
- imidazole and suitable difunctional alkylating agents are used to synthesize two diamines containing imidazole units, which are subsequently converted into polyquaternary polysiloxanes in a manner analogous to EP 282720.
- Cationic compounds produced in this way are said to have a further increased compatibility compared to the anionic surfactants present in cosmetic formulations.
- washout resistance from hair refers to the short-term attack of primarily water and very mild surfactants that do not irritate the skin
- wash-resistant, hydrophilic plasticizers for textiles have to withstand the attack of concentrated surfactant solutions with high fat and dirt-dissolving properties.
- modern detergents contain strongly alkaline complexing agents, oxidative bleaching agents and complex enzyme systems and the fibers are often exposed to the effects for hours at elevated temperatures.
- polyquaternary polysiloxane compounds are known, in which hydrophilic units (EO units) are additionally incorporated and the arrangement and sequence of the quat units to form hydrophilic units can be changed in such a way that, as a result, a better hydrophilic soft feel without loss of substantivity on textiles (cotton, polyester).
- EO units hydrophilic units
- Further approaches to improve compatibility with anionic surfactant systems and the efficiency of siloxane deposition on surfaces are aimed at using larger amounts of cationic surfactants (WO 00/71806 and WO 00/71807) or the use of cationic polysaccharide derivatives (JN.Gruber et. Al. , Colloids and Surfaces B: Biointerfaces 19 (2000) 127-135) in mixtures with polydimethylsiloxanes.
- WO 02/10257 discloses polysiloxane compounds with quaternary ammonium groups, which are built up from diamines, diepoxides containing polydiorganosiloxane groups and di (haloalkyl) ester polyether compounds. However, due to the production process, these contain a certain proportion of ester groups, which are sensitive to hydrolysis, especially under alkaline conditions, as an essential constituent. In addition, the polysiloxane compounds described therein have a rigid relationship between plasticizing polydiorganosiloxane blocks and hydrophilic blocks.
- polysiloxane compounds can therefore not always be tailored to specific requirements. This is hydrophilicity for certain applications. These polysiloxane compounds are not always satisfactory, while in other applications the softness or substantivity leave something to be desired. None of the solutions cited teaches how a further increase in hydrophilicity and substantivity can be achieved while maintaining the soft feel, or how, in particular, these properties can be quasi tailored to specific applications.
- linear polysiloxane copolymers their preparation and their use as wash-resistant hydrophilic plasticizers, the linear polysiloxane copolymers giving the textiles, after appropriate application, a soft grip typical of silicone and a pronounced hydrophilicity, and this property profile even after exposure to detergent formulations during repeated washing processes is not lost if the temperature is increased. It is a further object of the invention to provide the use of these linear polysiloxane copolymers as separate plasticizers after the washing of fibers and / or textiles or as plasticizers in the laundry with formulations based on nonionic or anionic / nonionic surfactants.
- linear polysiloxane copolymers are intended to prevent or reverse textile creasing.
- object of the present invention is to provide a linear polysiloxane copolymer, the properties of which with regard to soft hand, substantivity, hydrophilicity or the like can be tailored to a particular application in a simple manner.
- the present invention thus provides linear polyamino and / or polyammonium polysiloxane copolymers with the repeating unit:
- R in each case represents hydrogen or a monovalent organic radical, where Q does not bind to a carbonyl carbon atom,
- V represents at least one group V 1 and at least one group V 2 ,
- V 2 is selected from divalent or trivalent, straight-chain, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon radicals with up to 1000 carbon atoms (the
- R 2 is hydrogen, a monovalent, straight-chain, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon radical having up to 100 carbon atoms, which has one or more groups selected from -O-, -NH-, -C ( O) - and -C (S) -, and optionally by one or more substituents selected from the group consisting of a hydroxyl group, an optionally substituted, preferably containing one or more nitrogen atoms, heterocyclic group, amino, alkylamino , Dialkylamino, ammonium, polyether residues and polyether ester residues can be substituted, where if there are several groups -CONR 2 - these can be the same or different,
- -C (O) - and -C (S) - may contain, and
- radical V 2 may optionally be substituted by one or more hydroxyl groups
- V 1 is selected from divalent or trivalent, straight-chain, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon radicals with up to 1000 carbon atoms, optionally one or more groups selected from
- -C (O) -, -C (S) - and XL 1 - may contain, wherein -Z 1 - a group of the formula
- radical V 1 must not have an ester group (s) -C (O) -O- or -OC (O) -,
- Q is selected from the group consisting of:
- R is as defined above and V 1 and V 2 are divalent radicals.
- Q is selected from the group consisting of:
- t is from 2 to 10
- R 2 is as defined above, and the meaning of R 2 can be the same or different from the meaning of the above group R 2 ,
- R 3 has the meaning of R 2 , where R 2 and R 3 may be the same or different, or
- R 2 and R 3 together with the positively charged nitrogen atom form a five- to seven-membered heterocycle which can optionally additionally have one or more nitrogen, oxygen and / or sulfur atoms,
- R 5 , R 6 , R 7 can be the same or different and are selected from the group consisting of: H, halogen, hydroxyl group, nitro group, cyano group, Thiol group, carboxyl group, alkyl group, monohydroxyalkyl group, polyhydroxyalkyl group, thioalkyl group, cyanoalkyl group, alkoxy group, acyl group, acetyloxy group, cycloalkyl group, aryl group, alkylaryl group, and groups of the type -NHR, in which R w is H, alkyl group, monohydroxyalkyl group, polyhydroxyalkyl group, acetyl group, acetyl group and in each case two of the adjacent radicals R 5 , R 6 and R 7 with which they can form aromatic five- to seven-membered rings with the carbon atoms which bind to the heterocycle, and R 8 has the meaning of R 2 , where R 8 and R 2 are identical or different can.
- V 2 represents a group of the formula
- V 2 * is a divalent straight-chain, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon radical having up to 40 carbon atoms, which may be one or a plurality of groups selected from -O-, -CONH-, -CONR 2 -, in which R 2 is as defined above, can contain -C (O) - and -C (S) -, and the radical V 2 * optionally by one or more hydroxyl groups can be substituted.
- V 2 and V 2 * preferably also contain no ester groups -C (O) -O- or -OC (O) -.
- the linear polysiloxane copolymer according to the invention has the following repeating units:
- the molar ratio of the repeat units - [V 2 * -Z 2 -V 2 * -Q] - to - [VQ] - corresponds to the ratio V 2 / V L ⁇ 1.
- the linear polysiloxane copolymers according to the invention necessarily contain blocks which contain more than one - [V'-Qj unit or [V -Q] unit, linked to one another.
- the regular connection in which, for example, a prepolymer corresponding to the group -Q-jV-Qj x is reacted with monomer units corresponding to V 2 in a molar ratio of 1: 1, the linear polysiloxane copolymers can be prepared as follows:
- x can preferably be 1.01 to 2000 and is the mean.
- the linear polysiloxane copolymers represented by the formula - ⁇ V 2 -Q- [N 1 -Q] X - ⁇ - are characterized in that they have essentially no linked -V 2 -Q units, or in other words, are two -V 2 -Q units are always interrupted by at least one -V'-Q unit.
- x in the above formula is preferably about 0.001 to 0.99.
- the linear polysiloxane copolymers contain at least one linked -V 2 -Q unit, or in other words, two V'-Q units are always interrupted by at least one V 2 -Q unit.
- the group V 1 is selected from divalent, straight-chain, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon radicals with up to 400 carbon atoms, which optionally have one or more groups selected from -O-, -CO ⁇ H -, -CO ⁇ R 2 -, wherein R 2 is as defined above, -C (O>, -C (S and -Z 1 - may contain, wherein -Z 1 - a group of the formula
- R 1 is Ci to C 3 alkyl, fluoro (C -C 6 ) alkyl or Cö-aryl, and n 2 is as defined above.
- the group Q is selected from:
- R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 are as defined above.
- the molar ratio V 2 / V ] fulfills the relationship
- the molar ratio V 2 / V * preferably fulfills the relationship
- R, ⁇ Ci to Cis alkyl, especially methyl, ethyl, perfluoroalkylethylene, such as trifluoropropyl and phenyl,
- ni is between 20 and 50 or between 80 and 200.
- the number ni is the average degree of polymerization of the diorganosiloxy units in group Z 2nd
- n 2 0 to 15, particularly preferably 0 to 10, especially 0 to 5, more particularly 0.
- the number n 2 is the average degree of polymerization from Mn of the diorganosiloxy units in group Z 1 .
- R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 are as defined above.
- -CH CHCH 2 OC (O) CH 2 -
- -CH HCH 2 OC (O) CH 2 CH 2 -
- CH -CH CHCH2CH2 (OCH2CH2) v (OCH2CH) w OC (O) CH2CH2-
- -CH CHCH 2 -
- -CH CHCH 2 CH 2 -
- R 2 preferably represents:
- R 4 straight-chain, cyclic or branched Ci to C ⁇ 8 KoMenhydrogenrest, which by one or more groups, selected from -O-, -NH-, -C (O) -, and -C (S) - can contain and by one or more OH groups can be substituted, especially unsubstituted C 5 to 7 hydrocarbon residues which are derived from the corresponding fatty acids or hydroxylated C 3 to C ⁇ ⁇ residues which can be attributed to hydroxylated carboxylic acids, especially saccharide carboxylic acids, and very specifically
- V preferably stands for
- R 9 represents a divalent, saturated or mono- or polyunsaturated, straight-chain or branched hydrocarbon radical with two to 25 carbon atoms *,
- V 1 Preferred variants of V 1 are
- Q 1 to 50, in particular 2 to 50, especially 1 to 20, very particularly 1 to 10, and 1 or 2
- r 0 to 100, in particular 0 to 50, especially 0 to 20, very particularly 0 to 10, are preferred , as well as 0 or 1 or 2.
- the invention further relates to a method for producing the linear polysiloxanes according to the invention, in which a) at least one amine compound, selected from a diamine compound and / or a primary or secondary monoamine compound, is reacted with at least two difunctional organic compounds which are capable of reacting with the amino functions of the amine compound, the molar ratio of the organic compounds being so warmed, that the
- Condition V7V 1 ⁇ 1 is met, b) at least two moles of an amine compound, selected from a diamine compound and / or a primary or secondary monoamine compound, with one mole of a difunctional organic compound which is reactive with the amine functions of the amine compound to form a
- the diamine compound (monomer) is reacted, which is subsequently reacted with at least one amine compound, selected from a diamine compound and / or a primary or secondary monoamine compound, and at least one further difunctional organic compound which is reacted with the amino functions of the amine compounds, c) one Amine compound, selected from a diamine compound and / or a primary or secondary monoamine compound, is reacted with a difunctional organic compound which is capable of reacting with the amino functions of the amine compounds to form a diamine compound (amino-terminated oligomer), which is then reacted with at least one difunctional compound organic compound capable of reacting with the amino functions of the diamine compounds is reacted, d) an amine compound selected from a diamine compound and / or a primary or secondary monoamine compound with a difunctional one Reaction with the amino functions of the amine compound allowed organic
- Amino-functional compound (difunctional oligomer) is reacted, which is then reacted with at least one amine compound selected from a diamine compound and / or a primary or secondary monoamine compound, and at least one other
- AminofuMctionen capable compound is reacted, optionally monofunctional, preferably tertiary monoamines or suitable monoamines and / or monofunctional compounds which are capable of reacting with amino functions can be added as chain terminators, and the stoichiometry of the amino functions and of the functional groups which are capable of reacting with amino functions is always about 1: 1 in the last stage of the reaction, and any anaine functions present protonate, alkylate or can be quaternized.
- Variant a wherein at least one diamine compound, selected from a diamine compound and / or a primary or secondary monoamine compound, is reacted with at least two difunctional organic compounds capable of reacting with the amino functions of the amine compound, the molar ratio of the organic compounds Connections are chosen so that the
- Condition V TV ⁇ 1 is fulfilled, can be represented schematically as follows, for example:
- - [ ⁇ -V 2 - ⁇ ] - may include, from the latter two Q units and one V 1 and two V 2 Units emerge, and - [V 1 ] - and - [V 2 ] - the repetition units V 1 and V 2 corresponding
- At least one higher alkylated amine or one quaternary ammonium unit Q is formed, with the
- Polymerization secondary or tertiary amino functions can optionally be protomerized or quaternized in a separate step after the polymerization.
- the formation of quaternary ammonium atoms is preferred.
- Preferred examples of - [NN] - are as described in more detail below: piperazine and imidazole, preferred diamine units - [NV ⁇ N] - include, for example: polymethylene diamines, such as tetramethyl hexamethylene diamine, ⁇ -diamino-terminated polyethers, such as Jeffamine, etc.
- Preferred diamine units - NV 2 * -Z 2 -Y 2 * -N] - include, for example, reaction products of, ⁇ -dihydrogenpolydialkylsiloxanes with allylamines. Preferred examples of - [N] - are described in more detail below, for example dimethylamine.
- diamines - [N-N] - is preferred per se.
- Preferred - [V'j monomers have to be, for example, epic morhydrin, bisepoxides or bisacrylates. Mixtures of the mentioned - [V'j monomers, such as e.g. Mixtures of epichlorohydrin, bis-CMoralkyl esters or bisepoxides are implemented.
- Preferred - [V 2 ] monomers are monomers of the formula - [V 2 * -Z 2 -V 2 *] -, in which Z 2 is as defined above, and - [V 2 *] a functionalized one corresponding to the repeat unit V 2 * Represents group.
- Preferred - [V 2 ] monomers for forming the V 2 repeat units are, in particular, oc, ⁇ -diepoxy-terminated
- Variant b) can be carried out with diamines, - [N-N] -, and also suitable monoamines - [N] - du ⁇ -ch, and can be represented schematically, for example, as follows:
- Variant c can be represented schematically, for example, as follows:
- Variant d can be represented schematically, for example, as follows:
- Step 1) - [V 1 ] - + - [NN] - ⁇ - [ ⁇ - (NN-V ⁇ J- Step 2): - ⁇ - (NNV 1 ) * ] - + - [V 2 ] - + - [ N] - or - [NN] - ⁇ with respect to the preferred monomer units - [NN] -, - [V 1 ] - and - [V 2 ] - what has been said for ScMitt a) applies.
- R 1 has the meaning given above and n, depending on the desired repeat unit, is V 1 or V 2 , n 2 or ni, which are defined as above.
- these siloxanes can be prepared by known methods, for example by equilibration (Silicone, Chemistry and Technology, Vulkan-Verlag, Essen 1989, pp. 82-84). The emitting EinMüMung the structural elements V 2 * and Q can z. B. done in two ways.
- reactive ⁇ , ⁇ -functionalized intermediates by hydrosilylation, which can subsequently be converted into, ⁇ -di-tertiary amino structures or directly into the quaternary ammonium structures according to the invention.
- Suitable starting materials for the production of reactive intermediates are, for example, halogenated alkenes or alkynes, especially allyl chloride, allyl bromide, chlorpropine and CMorbutin, unsaturated halocarboxylic acid esters, especially CMoracetic acid allyl esters,
- the general implementation of hydrosilylations with representatives of the substance groups mentioned is also known (B. Marcimec, Comprehensive Handbook on Hydrosilylation, Pergamon Press, Oxford 1992, pp. 116-121, 127-130, 134-137, 151-155).
- the reactive intermediates can then be reacted with compounds bearing secondary amino functions.
- Suitable representatives are N, N-dialkylamines, for example dimethylamine, diethylamine, dibutylamine, diethanolamine and N-methylglucamine, cyclic secondary amines, for example morpholine and piperidine, aminoamides which carry secondary amino functions, for example the reaction products of diethylenetriamine or dipropylenetriamine with lactones, such as ⁇ -butyrolone, such as ⁇ -butyrolactone , Gluconic acid ⁇ -lactone and Glucopyranosylarabonklalacton (DE-OS 4318536, Examples 11a, 12a, 13a), or secondary-tertiary diamines, such as N-methylpiperazine. It is particularly preferred to use corresponding imidazole or pyrazole derivatives, especially imidazole and pyrazole, for introducing tertiary amino functions.
- Particularly suitable as partners for the epoxy derivatives used in one embodiment are the secondary-tertiary diamines mentioned, and also imidazole and pyrazole. In this way, the alkylations can be directed regioselectively and without additional effort to the nitrogen atoms carrying hydrogen atoms.
- the amines are used in a ratio of 1 ⁇ secondary amino groups: reactive groups ⁇ 10, preferably 1 to 3, especially 1 to 2, very particularly 1. Excess amine may need to be removed.
- a preliminary provision of prepolymers terminated by amino groups, such as - [NC 1 - ⁇ ] - opens up the possibility of carrying out the copolymer formation directly with suitable reactive intermediates, for example epoxy derivatives. It is also preferred to present the reactive intermediates and the starting components for the construction of - [V 1 - (QV 1 ) X ] - together and then to react them.
- the total stoichiometry is selected such that the sum of the amino functions and the groups reactive with them is approximately 1: 1.
- the alkylene, alkenylene, alkynylene and aryl units are preferably introduced starting from the corresponding halogens, especially CMorides and bromides.
- exemplary representatives are 1,6-DicMorhexan, 1,4-DicMorbut (2-) en, 1,4-DicMorbut (2-) in and 1,4-Bis (chloromethyl) benzene.
- Polyalkylene oxide units can also be introduced via the ⁇ , ⁇ -dihalogen compounds. These are from the oligomeric and polymeric AUcylenoxiden of the general composition
- Mono-, di- or polyhydroxy-functional units as group V 1 can be introduced starting from epoxy derivatives.
- a partial or complete subsequent quarter of remaining tertiary Amino structures represent a preferred variant for setting a desired high density of the quaternary ammonium groups.
- the corresponding aromatic amines imidazole or pyrazole lead to products with a delocalized charge.
- primary tertiary diamines for example N, N-dimethylpropylenediamine and 1- (3-aminopropyl) imidazole
- comb-like structures can be built up, for which the degree of quaternization can be warmed during a final alkylation.
- the alkylations can also achieve quaternization levels of, on average, less than one quaternary ammonium group per repeating unit
- the secondary amines initially provide Merbei with poly-tertiary amino-modified siloxane copolymers or prepolymers, which can be quaternized in part or in full in an abscMiessere reaction to - [V 1 - (QV 1 ) X ] -. However, it is also preferred in this variant to quaternize at least one nitrogen atom per repeat unit.
- Suitable quaternization agents are the generally known groups of substances such as alkyl halides, halocarboxylic acid esters, epoxy derivatives in the presence of H * and dialkyl sulfates, especially dimethyl sulfate.
- Misc commercially available secondary amines are produced in a preferred embodiment starting from the corresponding diprimeric amines, for example hexamethylenediamine, by alkylation with epoxides, such as e.g. Ethylene oxide, propylene oxide, isopropyl glycidyl ether using the different reaction rates of primary and secondary amines.
- epoxides such as e.g. Ethylene oxide, propylene oxide, isopropyl glycidyl ether using the different reaction rates of primary and secondary amines.
- Aons A " which neutralize positive charges resulting from the ammonium groups are preferably the ions formed during the quaternization, such as halide ions, especially chloride and bromide, acyl sulfates, especially methosulfate, carboxylates, especially acetate, propionate, octanoate, decanoate, dodecanoate, tetradecanoate, Hexadecanoate, octadecanoate, oleate, sufonates, especially toluenesulfonate, but other amones can also be introduced by ion exchange, for example organic AMons, such as polyether carboxylates and polyether sulfates.
- organic AMons such as polyether carboxylates and polyether sulfates.
- the quaternization reactions are preferably carried out in water, polar organic solvents or mixtures of the two components mentioned.
- Suitable are e.g. Alcohols, especially methanol, ethanol, i-propanol and n-butanol, glycols, such as ethylene glycol, diethylene glycol, triethylene glycol, the methyl, ethyl and butyl ethers of the glycols mentioned, 1,2-propylene glycol and 1,3-propylene glycol, ketones, such as acetone and methyl ethyl ketone, esters such as ethyl acetate, butyl acetate and 2-ethylhexyl acetate, ethers such as tetrahydrofuran and nitro compounds such as nitromethane.
- the choice of solvent depends essentially on the solubility of the reactants, the desired reaction temperature and a reactivity which may be present and disrupt the reaction.
- the reactions are carried out in the range from 20 ° C. to 130 ° C., preferably 40 ° C. to 100 ° C.
- the molecular weight is expediently limited.
- the linear polyorganosiloxane polymers can, in addition to the terminal groups naturally resulting from the reaction of the monomeric starting materials, also from monofunctional chain terminators, such as trialkylamines etc. and for example resulting AmmoMum, amino, ether or hydroxy end groups.
- the present invention further relates to the use of the linear polyorganosiloxane polymers according to the invention or the linear polyorganosiloxane polymers obtained by the process of the invention in cosmetic formulations, in detergents or for the surface treatment of substrates.
- the linear polyorganosiloxane polymers according to the invention which combine the softening properties of siloxane structures and the tendency of quaternary ammonium groups to adsorb onto negatively charged solid surfaces, can • be used successfully in cosmetic formulations for skin and hair care, in polishes for treatment and Hard surface finishing, in formulations for drying automobiles and other hard surfaces after mascMnelle washes, for finishing textiles, textile fibers, paper, paper fibers, paper nonwovens, including fiber, textile and paper pretreatment and finishing, finishing of paper for cosmetics and sanitary areas, especially permanent hydropMle plasticizers, as separate plasticizers after washing textiles with aMomschen / nonionic detergent formulations, as a plasticizer in formulations for textile washing
- the invention further relates to compositions comprising at least one of the linear polyorganosiloxane polymers according to the invention together with at least one other ingredient customary for the composition, such as cosmetic compositions, detergent compositions, polishes, shampoos, ironing mats,
- polysiloxane derivatives according to the invention when used in the hair cosmetics sector, has favorable effects in terms of gloss, fixation (hold), body, volume, moisture regulation, color retention, protection from environmental influences (UV, salt water, etc.), reshapeability, antistatic properties, dyeability, combability, etc.
- the quaternary polysiloxane compounds can preferably be used in the cosmetic and hair care formulations according to WO 02-10257.
- the ratio V / 2 IV 7 * 1 in this example is approximately 0.058.
- the ratio MS V IV in this example is approximately 0.12.
- the ratio V / V in this example is approximately 0.058.
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Abstract
Description
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Priority Applications (8)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/533,837 US7563856B2 (en) | 2002-11-04 | 2003-10-31 | Linear polyamino and/or polyammonium polysiloxane copolymers II |
AU2003301831A AU2003301831A1 (en) | 2002-11-04 | 2003-10-31 | Linear polyamino and/or polyammonium polysiloxane copolymers ii |
BRPI0315973A BRPI0315973A8 (pt) | 2002-11-04 | 2003-10-31 | copolímeros ii lineares de poliamino e/ou poliamônio-polissiloxano |
EP03810454A EP1563136B1 (de) | 2002-11-04 | 2003-10-31 | Lineare polyamino- und/oder polyammonium-polysiloxancopolymere ii |
DE50309853T DE50309853D1 (de) | 2002-11-04 | 2003-10-31 | Lineare polyamino- und/oder polyammonium-polysiloxancopolymere ii |
MXPA05004751A MXPA05004751A (es) | 2002-11-04 | 2003-10-31 | Copolimeros de poliamino y/o poliamonio polisiloxano ii lineales. |
JP2004549174A JP2006505643A (ja) | 2002-11-04 | 2003-10-31 | 線状ポリアミノおよび/またはポリアンモニウムポリシロキサン共重合体ii |
CA002504981A CA2504981A1 (en) | 2002-11-04 | 2003-10-31 | Linear polyamino and/or polyammonium polysiloxane copolymers ii |
Applications Claiming Priority (2)
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DE10251524 | 2002-11-04 | ||
DE10251524.7 | 2002-11-04 |
Publications (1)
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WO2004042136A1 true WO2004042136A1 (de) | 2004-05-21 |
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ID=32308479
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PCT/EP2003/050773 WO2004042136A1 (de) | 2002-11-04 | 2003-10-31 | Lineare polyamino- und/oder polyammonium-polysiloxancopolymere ii |
Country Status (12)
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US (1) | US7563856B2 (de) |
EP (1) | EP1563136B1 (de) |
JP (1) | JP2006505643A (de) |
CN (1) | CN100487025C (de) |
AT (1) | ATE395458T1 (de) |
AU (1) | AU2003301831A1 (de) |
BR (1) | BRPI0315973A8 (de) |
CA (1) | CA2504981A1 (de) |
DE (1) | DE50309853D1 (de) |
ES (1) | ES2308036T3 (de) |
MX (1) | MXPA05004751A (de) |
WO (1) | WO2004042136A1 (de) |
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WO2004069137A3 (de) * | 2003-02-07 | 2004-10-21 | Ge Bayer Silicones Gmbh & Co | Verwendung von polyamino- und/oder polyammonium-polysiloxancopolymeren |
DE102007012908A1 (de) | 2007-03-19 | 2008-09-25 | Momentive Performance Materials Gmbh | Neue Polyamid-Polysiloxan-Verbindungen |
WO2008138363A1 (de) * | 2007-05-10 | 2008-11-20 | Evonik Goldschmidt Gmbh | Stickstoffhaltige polyether-polysiloxan-blockcopolymere , verfahren zu deren herstellung und deren verwendung zur verbesserung der oberflächeneigenschaften von geweben und fasern |
WO2008142109A1 (de) | 2007-05-21 | 2008-11-27 | Momentive Performance Materials Gmbh | Polycarbonat- und/oder polyurethan-polyorganosiloxan-verbindungen |
DE102007027027A1 (de) | 2007-06-08 | 2008-12-11 | Momentive Performance Materials Gmbh & Co. Kg | Neue Polyharnstoff- und/oder Polyurethan-Polyorganosiloxan-Verbindungen |
JP2009503216A (ja) * | 2005-08-01 | 2009-01-29 | モーメンテイブ・パーフオーマンス・マテリアルズ・ゲゼルシヤフト・ミツト・ベシユレンクテル・ハフツング | ポリアンモニウム/ポリシロキサンコポリマー |
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Cited By (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2004069137A3 (de) * | 2003-02-07 | 2004-10-21 | Ge Bayer Silicones Gmbh & Co | Verwendung von polyamino- und/oder polyammonium-polysiloxancopolymeren |
US8076442B2 (en) * | 2005-03-30 | 2011-12-13 | Momentive Performance Materials Gmbh | Polyamino and/or polyammonium/polysiloxane copolymer compounds with polyalkylene oxide units in comb-shaped arrangement |
JP2009503216A (ja) * | 2005-08-01 | 2009-01-29 | モーメンテイブ・パーフオーマンス・マテリアルズ・ゲゼルシヤフト・ミツト・ベシユレンクテル・ハフツング | ポリアンモニウム/ポリシロキサンコポリマー |
KR101331264B1 (ko) | 2005-08-01 | 2013-11-22 | 모멘티브 퍼포먼스 머티리얼즈 게엠베하 | 폴리암모늄/폴리실록산 공중합체 |
US8362185B2 (en) * | 2005-08-01 | 2013-01-29 | Momentive Performance Materials Gmbh | Polyammonium/polysiloxane copolymers |
DE102007012908A1 (de) | 2007-03-19 | 2008-09-25 | Momentive Performance Materials Gmbh | Neue Polyamid-Polysiloxan-Verbindungen |
US8013097B2 (en) | 2007-04-11 | 2011-09-06 | Dow Corning Corporation | Silicone polyether block copolymers having organofunctional endblocking groups |
WO2008138363A1 (de) * | 2007-05-10 | 2008-11-20 | Evonik Goldschmidt Gmbh | Stickstoffhaltige polyether-polysiloxan-blockcopolymere , verfahren zu deren herstellung und deren verwendung zur verbesserung der oberflächeneigenschaften von geweben und fasern |
DE102007023869A1 (de) | 2007-05-21 | 2008-12-18 | Momentive Performance Materials Gmbh & Co. Kg | Neue Polycarbonat- und/oder Polyurethan-Polyorganosiloxan-Verbindungen |
WO2008142109A1 (de) | 2007-05-21 | 2008-11-27 | Momentive Performance Materials Gmbh | Polycarbonat- und/oder polyurethan-polyorganosiloxan-verbindungen |
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DE102008013584A1 (de) | 2008-03-11 | 2009-09-17 | Momentive Performance Materials Gmbh | Neue Polycarbonat-Polyorganosiloxan- und/oder Polyurethan-Polyorganosiloxan-Verbindungen |
WO2009115412A1 (de) * | 2008-03-18 | 2009-09-24 | Momentive Performance Materials Gmbh | Verwendung von polyamino- und/oder polyammonium-polysiloxan-copolymer-verbindungen |
US9593208B2 (en) | 2013-09-23 | 2017-03-14 | Rudolf Gmbh | Polysiloxanes with quaternized heterocyclic groups |
Also Published As
Publication number | Publication date |
---|---|
EP1563136A1 (de) | 2005-08-17 |
AU2003301831A1 (en) | 2004-06-07 |
BR0315973B1 (pt) | 2013-03-19 |
EP1563136B1 (de) | 2008-05-14 |
CA2504981A1 (en) | 2004-05-21 |
BRPI0315973A8 (pt) | 2018-05-15 |
US20060235181A1 (en) | 2006-10-19 |
DE50309853D1 (de) | 2008-06-26 |
CN100487025C (zh) | 2009-05-13 |
CN1735728A (zh) | 2006-02-15 |
JP2006505643A (ja) | 2006-02-16 |
MXPA05004751A (es) | 2005-08-03 |
ATE395458T1 (de) | 2008-05-15 |
ES2308036T3 (es) | 2008-12-01 |
BR0315973A (pt) | 2005-09-27 |
US7563856B2 (en) | 2009-07-21 |
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