JP2017504730A - ブロック化ポリイソシアネートを含む仕上げ剤 - Google Patents
ブロック化ポリイソシアネートを含む仕上げ剤 Download PDFInfo
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- JP2017504730A JP2017504730A JP2016533528A JP2016533528A JP2017504730A JP 2017504730 A JP2017504730 A JP 2017504730A JP 2016533528 A JP2016533528 A JP 2016533528A JP 2016533528 A JP2016533528 A JP 2016533528A JP 2017504730 A JP2017504730 A JP 2017504730A
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- Prior art keywords
- formulation
- group
- hydrophobic
- polyisocyanate
- formulation according
- Prior art date
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- 239000005056 polyisocyanate Substances 0.000 title claims abstract description 89
- 229920001228 polyisocyanate Polymers 0.000 title claims abstract description 89
- 239000003795 chemical substances by application Substances 0.000 title description 12
- 239000000203 mixture Substances 0.000 claims abstract description 121
- 238000009472 formulation Methods 0.000 claims abstract description 98
- 230000002209 hydrophobic effect Effects 0.000 claims abstract description 52
- 239000004744 fabric Substances 0.000 claims description 44
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 36
- 125000000129 anionic group Chemical group 0.000 claims description 25
- 125000002091 cationic group Chemical group 0.000 claims description 23
- 239000000839 emulsion Substances 0.000 claims description 22
- 239000007787 solid Substances 0.000 claims description 22
- 125000001165 hydrophobic group Chemical group 0.000 claims description 17
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 12
- 239000004753 textile Substances 0.000 claims description 12
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims description 11
- 229920002313 fluoropolymer Polymers 0.000 claims description 10
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 9
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 9
- 229930195729 fatty acid Natural products 0.000 claims description 9
- 239000000194 fatty acid Substances 0.000 claims description 9
- 229920001296 polysiloxane Polymers 0.000 claims description 9
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 7
- 238000010438 heat treatment Methods 0.000 claims description 7
- 239000004814 polyurethane Substances 0.000 claims description 7
- 229920002635 polyurethane Polymers 0.000 claims description 7
- 150000004665 fatty acids Chemical class 0.000 claims description 6
- 229920000233 poly(alkylene oxides) Polymers 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 239000002736 nonionic surfactant Substances 0.000 claims description 5
- 229920000193 polymethacrylate Polymers 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 150000007942 carboxylates Chemical class 0.000 claims description 4
- 239000003093 cationic surfactant Substances 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 239000002759 woven fabric Substances 0.000 claims description 4
- PCHXZXKMYCGVFA-UHFFFAOYSA-N 1,3-diazetidine-2,4-dione Chemical compound O=C1NC(=O)N1 PCHXZXKMYCGVFA-UHFFFAOYSA-N 0.000 claims description 3
- PJMDLNIAGSYXLA-UHFFFAOYSA-N 6-iminooxadiazine-4,5-dione Chemical compound N=C1ON=NC(=O)C1=O PJMDLNIAGSYXLA-UHFFFAOYSA-N 0.000 claims description 3
- 239000003945 anionic surfactant Substances 0.000 claims description 3
- 239000004202 carbamide Substances 0.000 claims description 3
- 150000001718 carbodiimides Chemical class 0.000 claims description 3
- 239000012141 concentrate Substances 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 3
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000003010 ionic group Chemical group 0.000 claims description 2
- 150000007974 melamines Chemical class 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 25
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 19
- -1 polyethylene Polymers 0.000 description 18
- 230000000694 effects Effects 0.000 description 15
- 239000006185 dispersion Substances 0.000 description 14
- 238000012360 testing method Methods 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 150000001412 amines Chemical class 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000000178 monomer Substances 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- 125000001931 aliphatic group Chemical group 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 8
- 238000004132 cross linking Methods 0.000 description 8
- 239000005871 repellent Substances 0.000 description 8
- 239000001993 wax Substances 0.000 description 8
- SDXAWLJRERMRKF-UHFFFAOYSA-N 3,5-dimethyl-1h-pyrazole Chemical compound CC=1C=C(C)NN=1 SDXAWLJRERMRKF-UHFFFAOYSA-N 0.000 description 7
- 150000003939 benzylamines Chemical group 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 239000004094 surface-active agent Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 6
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 229910052731 fluorine Inorganic materials 0.000 description 6
- 239000011737 fluorine Substances 0.000 description 6
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 230000002940 repellent Effects 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical compound C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 description 5
- 229920000742 Cotton Polymers 0.000 description 5
- 239000005058 Isophorone diisocyanate Substances 0.000 description 5
- 125000002511 behenyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 239000002981 blocking agent Substances 0.000 description 5
- 239000012973 diazabicyclooctane Substances 0.000 description 5
- 239000012153 distilled water Substances 0.000 description 5
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 5
- HIPXPABRMMYVQD-UHFFFAOYSA-N n-benzylbutan-1-amine Chemical compound CCCCNCC1=CC=CC=C1 HIPXPABRMMYVQD-UHFFFAOYSA-N 0.000 description 5
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 5
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- VATRWWPJWVCZTA-UHFFFAOYSA-N 3-oxo-n-[2-(trifluoromethyl)phenyl]butanamide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1C(F)(F)F VATRWWPJWVCZTA-UHFFFAOYSA-N 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000004566 IR spectroscopy Methods 0.000 description 4
- 239000002202 Polyethylene glycol Substances 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropyl acetate Chemical compound CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 4
- HGEMCUOAMCILCP-UHFFFAOYSA-N isotridecane Natural products CCCCCCCCCCC(C)C HGEMCUOAMCILCP-UHFFFAOYSA-N 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 125000006239 protecting group Chemical group 0.000 description 4
- 230000001681 protective effect Effects 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- WHIVNJATOVLWBW-PLNGDYQASA-N (nz)-n-butan-2-ylidenehydroxylamine Chemical compound CC\C(C)=N/O WHIVNJATOVLWBW-PLNGDYQASA-N 0.000 description 3
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 3
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 3
- 239000004971 Cross linker Substances 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
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- 150000001252 acrylic acid derivatives Chemical class 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 125000002723 alicyclic group Chemical class 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 150000004985 diamines Chemical class 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 3
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- 150000007522 mineralic acids Chemical class 0.000 description 3
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
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- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 2
- CUVLMZNMSPJDON-UHFFFAOYSA-N 1-(1-butoxypropan-2-yloxy)propan-2-ol Chemical compound CCCCOCC(C)OCC(C)O CUVLMZNMSPJDON-UHFFFAOYSA-N 0.000 description 2
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- WAEVWDZKMBQDEJ-UHFFFAOYSA-N 2-[2-(2-methoxypropoxy)propoxy]propan-1-ol Chemical compound COC(C)COC(C)COC(C)CO WAEVWDZKMBQDEJ-UHFFFAOYSA-N 0.000 description 2
- SGVYKUFIHHTIFL-UHFFFAOYSA-N 2-methylnonane Chemical compound CCCCCCCC(C)C SGVYKUFIHHTIFL-UHFFFAOYSA-N 0.000 description 2
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- 239000000376 reactant Substances 0.000 description 2
- 125000006850 spacer group Chemical group 0.000 description 2
- 238000007655 standard test method Methods 0.000 description 2
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- 150000003512 tertiary amines Chemical class 0.000 description 2
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
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Abstract
Description
(i)式(I)の少なくとも1つのブロック化ポリイソシアネート
R1は互いに独立に、水素、C1−C4−アルキルまたはC6−C10−シクロアルキル、好ましくは水素であり、
R2は互いに独立に、水素、C1−C4−アルキルまたはC6−C10−シクロアルキル、好ましくは水素であり、
R3は互いに独立に、水素、C1−C4−アルキルまたはC6−C10−シクロアルキル、好ましくは水素であり、
R4は互いに独立に、C1−C4−アルキル、C6−C10−シクロアルキルまたはC7−C14−アラルキル、好ましくはメチル、エチル、プロピル、イソプロピル、n−ブチル、sec−ブチル、tert−ブチル、より好ましくはtert−ブチルであり、
mは、1、2、3、4または5から選択される整数であり、
nは、2〜10、好ましくは2〜8、より好ましくは2〜6の数であり、および
Yは、ポリイソシアネート基であり、場合により、疎水基および/またはアニオン基、カチオン基および/または非イオン基により置換される;および
(ii)少なくとも1つの疎油性および/または疎水性仕上げ剤。
Zは、ポリイソシアネート基であり、
Tは、疎水基であり、
Wは、カチオン基、アニオン基および/または非イオン基を含み、
Bは、−O−および/または−NH−であり、
oは、0.1〜4、好ましくは0.1〜1であり、および
pは、0〜1、好ましくは0.1〜0.5である。
Rは、HまたはCH3であり、
aは、0〜6、好ましくは2〜4の整数、より好ましくは2であり、および
bは、0〜4の整数、より好ましくは4である。
(i)ポリイソシアネートを提供するステップ;
(ii)ポリイソシアネートを、式(IV)のベンジルアミン、
(i)上記に定義した、式(I)および/または(II)の少なくとも1つのブロック化ポリイソシアネート、および
(ii)少なくとも1つの疎油性および/または疎水性仕上げ剤。
(a)本発明に係る製剤を提供するステップ、または、キットの構成要素(i)および(ii)を混合するステップ、
(b)ステップ(a)で得られる製剤または混合物を、布に適用するステップ;および
(c)布の熱処理。
(a)本発明に係る製剤またはキットの構成要素(i)および(ii)の混合物の、布(特に織物)への適用、および
(b)布の熱処理、により得られる。
90=水滴の付着が分離している、または外面が濡れている;
80=水の衝突箇所で外面が濡れている;
70=外面全体が部分的に濡れている;
50=外面全体が完全に濡れている;
0=外面および内面の全体が完全に濡れている(びしょ濡れ)。
スコア4=大きな滴が形成される;
スコア3=滴が試験サンプルの所々にくっつく;
スコア2=試験サンプルが部分的に濡れている;
スコア1=試験サンプルの表面全体がびしょ濡れになる。
Ruco−Guard TIE:固形分:25%、ブタノンオキシム−ブロック化芳香族ポリイソシアネートの水性エマルション;Rudolf GmbH
Cassurit FF fl.:固形分:40%、3,5−ジメチルピラゾール−ブロック化脂肪族ポリイソシアネートの水性エマルション;Clariant
Ruco−Guard AFB6 conc.:固形分:27%、フルオロカーボンポリマー−含有の、2−(パーフルオロヘキシル)エチル(メタ)アクリレート系を含む、疎油性および疎水性の作用物質の水性エマルション、Rudolf GmbH
Ruco−Dry ECO:固形分:20%、フルオロカーボンポリマー−フリーの疎水性の作用物質の水性エマルション;Rudolf GmbH
Aduxol MPEG 750:ポリエチレングリコールモノメチルエーテル M=およそ750g/mol;Scharer and Schlafer AG
Aduxol MPEG 550:ポリエチレングリコールモノメチルエーテル M=およそ550g/mol;Scharer and Schlafer AG
Desmodur N 3300:脂肪族ポリイソシアネート(ヘキサメチレンジイソシアネートトリメリサート);Bayer Material Science
Desmodular N 3200:脂肪族ポリイソシアネート(ヘキサメチレンジイソシアネート ビウレット);Bayer Material Science
Tolonate IDT 70 B:脂肪族ポリイソシアネート(イソホロンジイソシアネートトリメリサート);Bayer Material Science
Lutensol TO 129:イソトリデカノール12 EO;BASF
Arquad T 50:牛脂脂肪トリメチルアンモニウム塩化物
還流濃縮器、調節可能な攪拌機および内部温度計を備える三つ口フラスコ中に、65.0g(337.2mmol NCO)のDesmodur N3300を、保護ガスの下で、60.0gのジプロピレングリコールジメチルエーテル中に溶解させる。それから、0.24gのジアザビシクロオクタンおよび4.85g(18.0mmol)のステアリルアルコールを加える。反応混合物を、30分間55℃で撹拌する。それから、10.0g(13.3mmol)のAduxol MPEG 750および0.14g(7.8mmol)の水を、反応混合物に加える。1時間後に、55℃で、残存するNCO−基を、47.0g(287.8mol)のtert.−ブチルベンジルアミンと反応させる。IR分光法を用いて、変換が完了していることを確認する。
還流濃縮器、調節可能な攪拌機および内部温度計を備える三つ口フラスコ中に、71.0g(207.9mmol NCO)のTolonate IDT 70 Bを、保護ガスの下で、60gの酢酸イソプロピル中に溶解させる。それから、0.1gのジアザビシクロオクタン、4.0g(12.3mmol)のベヘニルアルコールおよび29.50g(180,6mmol)のtert.−ブチルベンジルアミンを加える。反応混合物を30分間75℃で撹拌する。それから、1.0g(8.5mmol)の1,6−ヘキサンジオールを反応混合物に加える。1時間後に、75℃でIR分光法を用いて、変換が完了していることを確認する。もしそうならば65℃までの冷却を行なう。
還流濃縮器、調節可能な攪拌機および内部温度計を備える三つ口フラスコ中に、45.0g(246.3mmol NCO)のDesmodur N 3200を、保護ガスの下で、83gの酢酸イソプロピル中に溶解させる。それから、0.1gのジアザビシクロオクタン、3.5g(18.8mmol)のラウリルアルコールおよび34.50g(211.3mmol)のtert.−ブチルベンジルアミンを加える。反応混合物を30分間75℃で撹拌する。それから、1.00g(8.5mmol)の1,6−ヘキサンジオールを反応混合物に加える。1時間後に、75℃でIR分光法を用いて、変換が完了していることを確認する。もしそうならば65℃までの冷却を行なう。
還流濃縮器、調節可能な攪拌機および内部温度計を備える三つ口フラスコ中に、65.0g(337.2mmol NCO)のDesmodur N3300を、保護ガスの下で100.0gのアセトン中に溶解させる。ここで、0.24gのジアザビシクロオクタンおよび5.9g(31.7mmol)のラウリルアルコールを加える。反応混合物を30分間55℃で撹拌する。それから、7.9g(14.4mmol)のAduxol MPEG 550および0.14g(7.8mmol)の水を反応混合物に加える。1時間後に、55℃で、残存するNCO−基を、45.0g(275.6mol)のtert.−ブチルベンジルアミンと反応させる。IR分光法を用いて、変換が完了していることを確認する。アセトンを留去して粘性マスを残し、それに6.96gのLutensol TO 129および1.41gの酢酸(60%)を加える。激しく撹拌して、それから、290gの蒸留水を、50℃で激しく撹拌しながら少量ずつ加える。結果物は、およそ25%の固形分を含む微細な粒子エマルションである。
Claims (26)
- 製剤であって、
(i)式(I)の少なくとも1つのブロック化ポリイソシアネート
R1は互いに独立に、水素、C1−C4−アルキルまたはC6−C10−シクロアルキル、好ましくは水素であり、
R2は互いに独立に、水素、C1−C4−アルキルまたはC6−C10−シクロアルキル、好ましくは水素であり、
R3は互いに独立に、水素、C1−C4−アルキルまたはC6−C10−シクロアルキル、好ましくは水素であり、
R4は互いに独立に、C1−C4−アルキル、C6−C10−シクロアルキルまたはC7−C14−アラルキル、好ましくはメチル、エチル、プロピル、イソプロピル、n−ブチル、sec−ブチル、tert−ブチル、より好ましくはtert−ブチルであり、
mは、1、2、3、4または5から選択される整数であり、
nは、2〜10、好ましくは2〜8、より好ましくは2〜6の数であり、および
Yは、ポリイソシアネート基であり、場合により、疎水基および/またはアニオン基、カチオン基および/または非イオン基で置換される;および
(ii)少なくとも1つの疎油性および/または疎水性仕上げ剤、
を含む、
製剤。 - 請求項1に記載の製剤であって、
R1、R2およびR3は、それぞれの場合においてHであり、
R4はtert−ブチルである、
製剤。 - 請求項1または2に記載の製剤であって、
前記ポリイソシアネート基Yは、6〜200炭素原子を有する脂肪族脂環式および/または芳香族炭化水素基であり、場合により、少なくとも1つのウレタン、アロファネート、尿素、ビウレット、ウレトジオン、イソシアヌレート、カルボジイミド、イミノオキサジアジンジオンおよび/またはウレトンイミン基を含む、
製剤。 - 請求項1から3のいずれか一項に記載の製剤であって、
前記の疎水基および/またはアニオン基、カチオン基および/または非イオン基は、ウレタンを介して、および/または尿素基を介して、前記ポリイソシアネート基に結合している、
製剤。 - 請求項1から4のいずれか一項に記載の製剤であって、
前記疎水基は、直鎖、環状または分岐の、飽和または少なくとも部分的に不飽和の、8〜24炭素原子を有する炭化水素基である、
製剤。 - 請求項1から5のいずれか一項に記載の製剤であって、
前記アニオン基は、カルボキシレートおよび/またはスルホナートを含み、
前記カチオン基は、第四級アンモニウムイオンを含む、
製剤。 - 請求項1から6のいずれか一項に記載の製剤であって、
前記非イオン基は、200〜2,000g/mol、好ましくは400〜1,000g/molの重量平均分子量を有するポリアルキレンオキシドを含む、
製剤。 - 請求項1から7のいずれか一項に記載の製剤であって、
前記ブロック化ポリイソシアネートは、式(II)を有し、
Zは、ポリイソシアネート基であり、
Tは、疎水基であり、
Wは、カチオン性、アニオン性および/または非イオン基を含み、
Bは、−O−および/または−NH−であり、
oは、0.1〜4、好ましくは0.1〜1であり、
pは、0〜1、好ましくは0.1〜0.5であり、および
R1〜R4、m、nは、上記の定義のとおりである、
製剤。 - 請求項8に記載の製剤であって、
n+o+pの合計に対して、n=70〜98%、好ましくは80〜95%である、
製剤。 - 請求項8または9のいずれか一項に記載の製剤であって、
n+o+pの合計に対して、p=0〜10%、好ましくは0〜7%である、
製剤。 - 請求項8から10のいずれか一項に記載の製剤であって、
n+o+pの合計に対して、o=2〜20%、好ましくは2〜10%である、
製剤。 - 請求項1から11のいずれか一項に記載の製剤であって、
前記の疎油性および/または疎水性仕上げ剤は、少なくとも1つのフルオロカーボンポリマーを含む、
製剤。 - 請求項12に記載の製剤であって、
前記フルオロカーボンポリマーは、少なくとも1つの式(III)の繰り返し単位を含み、
Rは、HまたはCH3であり、
aは、0〜6の整数、好ましくは2であり、および
bは、0〜6の整数、好ましくは4である、
製剤。 - 請求項1から13のいずれか一項に記載の製剤であって、
前記疎水性仕上げ剤は、フッ素フリーである、
製剤。 - 請求項14に記載の製剤であって、
前記フッ素フリーの疎水性仕上げ剤は、ワックス、ポリ(メタ)アクリレート、ポリウレタン、脂肪酸変性メラミン、オルガノポリシロキサン、脂肪酸の金属塩、脂肪酸濃縮物またはそれらの混合物を含む、
製剤。 - 請求項1から15のいずれか一項に記載の製剤であって、
前記製剤は、少なくとも1つの有機溶媒、水またはそれらの混合物をさらに含む、
製剤。 - 請求項1から16のいずれか一項に記載の製剤であって、
前記製剤は、エマルションである、
製剤。 - 請求項1から17のいずれか一項に記載の製剤であって、
少なくとも1つのアニオン性、カチオン性および/または非イオン性界面活性剤をさらに含む、
製剤。 - 請求項1から18のいずれか一項に記載の製剤であって、
前記製剤は、固形分に対して、10%〜80%、好ましくは20%〜70%、より好ましくは30%〜60%の割合で、ブロック化ポリイソシアネートを含む、
製剤。 - 請求項1から19のいずれか一項に記載の製剤であって、
前記製剤は、固形分に対して、15%〜90%、好ましくは30%〜80%、より好ましくは40%〜70%の割合で、疎油性および/または疎水性仕上げ剤を含む、
製剤。 - 式(II)のブロック化ポリイソシアネートであって、
製剤。 - 式(II)のブロック化ポリイソシアネートを生産する方法であって、
以下のステップ:
(i)ポリイソシアネートを提供するステップ;
(ii)前記ポリイソシアネートを、式(IV)のベンジルアミン
を含む、
方法。 - キットであって、
(i)請求項1から11または21のいずれか一項に定義される、式(I)および/または(II)の少なくとも1つのブロック化ポリイソシアネート、および
(ii)請求項12から15のいずれか一項に定義される、少なくとも1つの疎油性および/または疎水性仕上げ剤、
を含む、
キット。 - 請求項1から20のいずれか一項に記載の製剤、請求項21に記載の化合物、または請求項23に記載のキットの、使用であって、
布(特に織物)の、疎油性および/または疎水性仕上げのための、
使用。 - 布(特に織物)を仕上げるための方法であって、
以下のステップ:
(a)請求項1から20のいずれか一項に記載の製剤または請求項23に記載のキットの構成要素(i)および(ii)の混合物を提供するステップ;
(b)前記製剤またはステップ(a)で得られる前記混合物を、布に適用するステップ;および
(c)前記布の熱処理、を含む、
方法。 - 疎油性および/または疎水性に仕上げられた布(特に織物)であって、
(i)請求項1から20のいずれか一項に記載の製剤または請求項23に記載のキットの構成要素(i)および(ii)の混合物の、布(特に織物)への適用、および
(ii)前記布の熱処理、
により得られる、
布。
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JPWO2020203602A1 (ja) * | 2019-03-29 | 2020-10-08 | ||
WO2024058204A1 (ja) * | 2022-09-14 | 2024-03-21 | ダイキン工業株式会社 | 撥液性繊維の製造方法 |
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EP3497166A1 (en) | 2016-08-12 | 2019-06-19 | 3M Innovative Properties Company | Fluorine-free fibrous treating compositions, treated substrates, and treating methods |
JP2020506256A (ja) * | 2017-01-13 | 2020-02-27 | コベストロ、ドイチュラント、アクチエンゲゼルシャフトCovestro Deutschland Ag | 織物用の低溶剤コーティング系 |
DE102018114549A1 (de) | 2018-06-18 | 2019-12-19 | CHT Germany GmbH | Polyurethan-Organopolysiloxane mit Carbodiimid-Gruppen |
WO2021107911A1 (en) * | 2019-11-25 | 2021-06-03 | Hewlett-Packard Development Company, L.P. | Printing fluids with blocked polyisocyante crosslinkers |
CN112030550A (zh) * | 2020-09-04 | 2020-12-04 | 应急管理部天津消防研究所 | 一种织物用阻燃、疏水、疏油、疏冰整理剂及其制备和应用方法 |
WO2024012662A1 (en) * | 2022-07-12 | 2024-01-18 | Huntsman Textile Effects (Germany) Gmbh | Extender compounds for durable water repellence |
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MX2016006797A (es) | 2017-02-17 |
EP3074437B1 (de) | 2018-01-17 |
KR101956377B1 (ko) | 2019-03-08 |
US20170022657A1 (en) | 2017-01-26 |
DK3074437T3 (en) | 2018-04-23 |
ES2658141T3 (es) | 2018-03-08 |
CN105980427A (zh) | 2016-09-28 |
DE102013224140A1 (de) | 2015-05-28 |
PE20160876A1 (es) | 2016-09-10 |
JP6649886B2 (ja) | 2020-02-19 |
MX357782B (es) | 2018-07-25 |
WO2015078811A1 (de) | 2015-06-04 |
ZA201603357B (en) | 2017-07-26 |
TR201802299T4 (tr) | 2018-03-21 |
KR20160091947A (ko) | 2016-08-03 |
US10253450B2 (en) | 2019-04-09 |
EP3074437A1 (de) | 2016-10-05 |
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