CN117264158A - Compound, treating agent and application thereof - Google Patents
Compound, treating agent and application thereof Download PDFInfo
- Publication number
- CN117264158A CN117264158A CN202310989101.5A CN202310989101A CN117264158A CN 117264158 A CN117264158 A CN 117264158A CN 202310989101 A CN202310989101 A CN 202310989101A CN 117264158 A CN117264158 A CN 117264158A
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- Prior art keywords
- equal
- formula
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 84
- 238000011282 treatment Methods 0.000 claims abstract description 39
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 32
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- 239000000047 product Substances 0.000 claims abstract description 22
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims abstract description 19
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- 229910052895 riebeckite Inorganic materials 0.000 claims abstract description 10
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- 125000003118 aryl group Chemical group 0.000 claims description 64
- 125000000217 alkyl group Chemical group 0.000 claims description 61
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 60
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- 238000000034 method Methods 0.000 claims description 27
- 125000002947 alkylene group Chemical group 0.000 claims description 25
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
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- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 claims description 2
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
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- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 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
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([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
- 150000002576 ketones Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 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
- 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
- 230000007935 neutral effect Effects 0.000 description 1
- 125000001400 nonyl 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])[H] 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000003961 organosilicon compounds Chemical class 0.000 description 1
- 125000005702 oxyalkylene group Chemical group 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 231100000719 pollutant Toxicity 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920001515 polyalkylene glycol Chemical class 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920005906 polyester polyol Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 238000003908 quality control method Methods 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000012502 risk assessment Methods 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
- 239000002210 silicon-based material Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000001502 supplementing effect Effects 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 239000012756 surface treatment agent Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water 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
- 239000012085 test solution Substances 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- JREYOWJEWZVAOR-UHFFFAOYSA-N triazanium;[3-methylbut-3-enoxy(oxido)phosphoryl] phosphate Chemical compound [NH4+].[NH4+].[NH4+].CC(=C)CCOP([O-])(=O)OP([O-])([O-])=O JREYOWJEWZVAOR-UHFFFAOYSA-N 0.000 description 1
- CEYYIKYYFSTQRU-UHFFFAOYSA-M trimethyl(tetradecyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCC[N+](C)(C)C CEYYIKYYFSTQRU-UHFFFAOYSA-M 0.000 description 1
- 125000002948 undecyl 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])[H] 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
- 239000011850 water-based material Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 230000037303 wrinkles Effects 0.000 description 1
Classifications
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/2805—Compounds having only one group containing active hydrogen
- C08G18/288—Compounds containing at least one heteroatom other than oxygen or nitrogen
- C08G18/289—Compounds containing at least one heteroatom other than oxygen or nitrogen containing silicon
-
- 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
- D06M15/564—Polyureas, polyurethanes or other polymers having ureide or urethane links; Precondensation products forming them
-
- 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
- D06M2101/00—Chemical constitution of the fibres, threads, yarns, fabrics or fibrous goods made from such materials, to be treated
- D06M2101/02—Natural fibres, other than mineral fibres
- D06M2101/04—Vegetal fibres
- D06M2101/06—Vegetal fibres cellulosic
-
- 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
- D06M2101/00—Chemical constitution of the fibres, threads, yarns, fabrics or fibrous goods made from such materials, to be treated
- D06M2101/16—Synthetic fibres, other than mineral fibres
- D06M2101/30—Synthetic polymers consisting of macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M2101/32—Polyesters
-
- 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
- D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
- D06M2200/01—Stain or soil resistance
-
- 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
- D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
- D06M2200/10—Repellency against liquids
- D06M2200/11—Oleophobic properties
-
- 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
- D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
- D06M2200/10—Repellency against liquids
- D06M2200/12—Hydrophobic properties
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
Abstract
The application relates to a compound, a treatment agent and application thereof. The preparation raw materials of the compound comprise an isocyanate group-containing compound and an isocyanate-reactive compound shown in a formula I, and the raw materials are defined as the specification. The compounds of the present application may be used in treatments including fabrics, leather, non-wovens, asbestos, fur, concrete, stone, paper products, plastics or paints, which can impart water-repellent, oil-repellent or soil-repellent functions to the surface of an article.
Description
Technical Field
The application relates to a compound, a treatment agent and application thereof. The compounds of the present application may be used in treatments including fabrics, leather, non-wovens, asbestos, fur, concrete, stone, paper products, plastics or paints, which can impart water-repellent, oil-repellent or soil-repellent functions to the surface of an article.
Technical Field
In the past, fluoropolymers have been used for surface water-repellent, oil-repellent or stain-repellent treatment of various articles such as fabrics, and the surface tension of the fluoropolymers is low, so that the surface properties of the fabrics can be changed, but the appearance and the like of the fabrics are not affected, and thus the fluoropolymers have been widely used.
However, in recent years, as the international society has increased attention to polyfluoroalkyl compounds (PFAS), month 3 of 2023, the european union chemical administration (ECHA) has opened public consultations concerning the increased restrictions on PFAS manufacture, release and use proposals in REACH restrictions (REACH appendix XIVII) submitted to ECHA in denmark, germany, the netherlands, norway and sweden, with the aim of giving the interested parties the opportunity to take PFAS REACH restrictions for regulatory comments, and after the public consultation has ended. The ECHA's Committee for Risk Assessment (RAC) and socioeconomic analysis Committee (SEAC) will evaluate proposed restrictions and develop comments based on consultation comments, ultimately being governed by the European Committee's decision whether to incorporate PFAS into restrictions.
In view of the above, new non-fluoropolymers have been proposed to replace existing fluorine-containing finishes.
CN107548406a proposes a polyurethane reacted with long chain alcohols, and the resulting polymer finishes textiles with good water repellency.
CN105980427a proposes a modified polyurethane, and the formed polymer has a good water repellent effect when finishing textiles.
The above polymers have only water repellent effect and no oil repellent effect, so the treated article surface such as fabric and the like has no barrier effect on oily stains.
Therefore, there is a need for a novel surface treatment agent which does not contain fluorine element, can reduce the burden on the environment, has excellent water-repellent effect and oil-repellent effect, and can effectively combat various stains on water and oil bases.
Disclosure of Invention
The object of the present application is to provide a novel compound, based on which a treatment agent prepared can treat various articles, thereby imparting excellent water and oil repellency and antifouling properties to the surfaces of the articles, and thus can effectively combat water-based and oil-based stains.
In a first aspect, the compounds of the present application are prepared from a starting material comprising an isocyanate group-containing compound and an isocyanate-reactive compound of formula I,
M-Z or Z-M-Z
I is a kind of
Wherein M is reactive with isocyanate;
z is selected from the structures shown in the following,
in Z, R 3 Each independently selected from C 1 -C 20 Alkyl, C of (2) 6 -C 20 Aryl, C of (2) 7 -C 12 Aralkyl of (C) 7 -C 12 Alkylaryl, C 1 -C 20 Alkoxy or R of (A) 4 -O-R 5 -a group, R 4 Is C 1 -C 20 Alkyl, C of (2) 6 -C 20 Aryl, C of (2) 7 -C 12 Aralkyl or C of (C) 7 -C 12 Alkylaryl group R of (2) 5 Is C 1 -C 20 An alkylene group of 1.ltoreq.a.ltoreq.200;
Y 1 and Y 2 Identical or different, each independently selected from C 1 -C 20 Alkyl, C of (2) 6 -C 20 Aryl, C of (2) 7 -C 12 Aralkyl of (C) 7 -C 12 Or an alkylaryl group of the formula (1):
R 7 each independently selected from C 1 -C 20 Alkyl, C of (2) 6 -C 20 Aryl, C of (2) 7 -C 12 Aralkyl or C of (C) 7 -C 12 Alkylaryl groups of (a); r is R 8 Each independently selected from C 1 -C 20 Alkyl, C of (2) 6 -C 20 Aryl, C of (2) 7 -C 12 Aralkyl of (C) 7 -C 12 Alkylaryl, C 1 -C 20 Alkoxy or R 9 -O-R 10 -a group wherein R 9 Is C 1 -C 20 Alkyl, C of (2) 6 -C 20 Aryl, C of (2) 7 -C 12 Aralkyl or C of (C) 7 -C 12 Alkylaryl group R of (2) 10 Is C 1 -C 20 The alkylene group of (2) is more than or equal to 0 and less than or equal to 200.
In some embodiments, the isocyanate group-containing compound is selected from one or more of hexamethylene diisocyanate homopolymer, 3-isocyanatomethyl-3, 4-trimethylcyclohexyl isocyanate, bis- (4-isocyanatocyclohexyl) methane, diisocyanate trimers of formulas II a through II e, polymeric diphenylmethane diisocyanate of formula II f, and isophorone diisocyanate prepolymer of formula II g,
in formula II f, n is 0 to 10, for example 1, 2, 3,4, 5, 6, 7, 8 or 9, and in formula II g, n is 0 to 10, for example 1, 2, 3,4, 5, 6, 7, 8 or 9.
The inventors of the present application have unexpectedly found that, after the surface of an article such as a fabric is treated with the above-mentioned compound obtained by reacting an isocyanate with a linear or branched silicon-containing compound, the article has excellent water-repellent and oil-repellent effects, thereby giving the surface of the treated article excellent resistance to various pollutants.
It is particularly pointed out that compounds containing isocyanate groups as reaction substrates, containing two or more isocyanate groups, especially in the case of multiple isocyanate groups, can increase the branching properties of the compounds. When reacted with compounds of the formula I containing isocyanate-reactive groups, for example Zerewitinoff hydrogen atoms, the compounds produced may contain a branched structure, the performance of which is also more excellent.
In some embodiments, the isocyanate group-containing compound is generally available from chemical manufacturers, such as Wanhua chemistryTT，/>PM,/>HT,/>HB,IT,/>IPP, etc.
In some embodiments, the isocyanate group-containing compound is selected from aliphatic and aromatic polyisocyanates having biuret structures, preferably under the trade name Wanhua chemistryHT (trimer of hexamethylene diisocyanate) andHB (hexamethylene diisocyanate based biuret polyisocyanate).
In some embodiments, one or more Zerewitinoff hydrogen atoms are contained in the M group of formula I.
In some embodiments, M is as shown in formula I-1:
H-X-B-
formula I-1
In formula I-1, B is selected from C 1 -C 20 Alkylene group, C 6 -C 20 Aryl groups of (a) and combinations thereof; x is-O-, -S-, -N (R) 1 )-，-O-(CH 2 ) k -N(R 2 )-，-O-C(O)-，R 1 Selected from hydrogen atoms or C 1 -C 20 Alkyl, R 2 Selected from hydrogen atoms or C 1 -C 20 Alkyl is more than or equal to 1 and less than or equal to 6.
In some embodiments, in formula I-1, B is C 1 -C 10 Alkylene groups of (2), e.gIs C 1 -C 3 Alkylene group, C 4 -C 6 Alkylene or C of (2) 8 -C 10 Alkylene groups of (a).
In some embodiments, in formula I-1, B is C 6 -C 15 Arylene groups of (2), e.g. C 6 -C 9 Arylene of (C) 10 -C 12 Arylene or C of (2) 13 -C 15 Arylene group of (a).
In some embodiments, in formula I-1, X is-N (R 1 )-，R 1 Selected from hydrogen atoms or C 1 -C 10 Alkyl radicals, e.g. C 1 -C 3 Alkyl, C of (2) 4 -C 6 Alkyl or C of (2) 8 -C 10 Is a hydrocarbon group. In some embodiments, in formula I-1, R 1 Selected from hydrogen atoms or methyl groups.
In some embodiments, in formula I-1, X is-O- (CH) 2 ) k -N(R 2 )-，R 2 Selected from hydrogen atoms or C 1 -C 10 Alkyl radicals, e.g. C 1 -C 3 Alkyl, C of (2) 4 -C 6 Alkyl or C of (2) 8 -C 10 K is 1, 2, 3,4, 5 or 6. In some embodiments, in formula I-1, R 2 Selected from hydrogen atoms or methyl groups.
In some embodiments, M is as shown in formula I-2:
formula I-2
In formula I-2, B is selected from C 1 -C 20 Alkylene group, C 6 -C 20 Arylene groups of (a) and combinations thereof.
In some embodiments, in formula I-2, B is C 1 -C 10 Alkylene of (C) 1 -C 3 Alkylene group, C 4 -C 6 Alkylene or C of (2) 8 -C 10 Alkylene groups of (a).
In some embodiments, in formula I-2, B is C 6 -C 15 Arylene of (2)For example C 6 -C 9 Arylene of (C) 10 -C 12 Arylene or C of (2) 13 -C 15 Arylene group of (a).
In some embodiments, in Z, R 3 Each independently is C 1 -C 10 Alkyl, C of (2) 6 -C 10 Aryl, C of (2) 7 -C 12 Aralkyl of (C) 7 -C 12 Alkylaryl, C 1 -C 10 Alkoxy or R 4 -O-R 5 -a group, R 4 Is C 1 -C 10 Alkyl, C of (2) 6 -C 10 Aryl, C of (2) 7 -C 12 Aralkyl or C of (C) 7 -C 12 Alkylaryl group R of (2) 5 Is C 1 -C 10 An alkylene group of 1.ltoreq.a.ltoreq.100; r is R 7 Each independently is C 1 -C 10 Alkyl, C of (2) 6 -C 10 Aryl, C of (2) 7 -C 12 Aralkyl or C of (C) 7 -C 12 Alkylaryl groups of (a); r is R 8 Each independently is C 1 -C 10 Alkyl, C of (2) 6 -C 10 Aryl, C of (2) 7 -C 12 Aralkyl of (C) 7 -C 12 Alkylaryl, C 1 -C 10 Alkoxy or R 9 -O-R 10 -a group wherein R 9 Is C 1 -C 10 Alkyl, C of (2) 6 -C 10 Aryl, C of (2) 7 -C 12 Aralkyl or C of (C) 7 -C 12 Alkylaryl group R of (2) 10 Is C 1 -C 10 And b is more than or equal to 0 and less than or equal to 100.
In some embodiments, in Z, R 3 Each independently is C 1 -C 6 Alkyl, C of (2) 6 -C 10 Aryl, C of (2) 7 -C 10 Aralkyl of (C) 7 -C 10 Alkylaryl, C 1 -C 6 Alkoxy or R 4 -O-R 5 -a group, R 4 Is C 1 -C 6 Alkyl, C of (2) 6 -C 10 Aryl, C of (2) 7 -C 10 Aralkyl or C of (C) 7 -C 10 Alkylaryl group R of (2) 5 Is C 1 -C 6 Sub-group of (2)Alkyl, a is more than or equal to 1 and less than or equal to 30; r is R 7 Each independently is C 1 -C 6 Alkyl, C of (2) 6 -C 10 Aryl, C of (2) 7 -C 10 Aralkyl or C of (C) 7 -C 10 Alkylaryl groups of (a); r is R 8 Each independently is C 1 -C 6 Alkyl, C of (2) 6 -C 10 Aryl, C of (2) 7 -C 10 Aralkyl of (C) 7 -C 10 Alkylaryl, C 1 -C 6 Alkoxy or R 9 -O-R 10 -a group wherein R 9 Is C 1 -C 6 Alkyl, C of (2) 6 -C 10 Aryl, C of (2) 7 -C 10 Aralkyl or C of (C) 7 -C 10 Alkylaryl group R of (2) 10 Is C 1 -C 16 The alkylene group of (2) is more than or equal to 0 and less than or equal to 30.
In some embodiments, a is an integer from 1 to 80, an integer from 1 to 30, an integer from 1 to 20, or an integer from 1 to 10.
In some embodiments, b is 0. In some embodiments, b is an integer from 1 to 30, an integer from 1 to 20, an integer from 1 to 10, or an integer from 1 to 5.
In some embodiments, each Z is independently selected from one or more of the following structures i-1 to i-6:
r is each independently selected from C 1 -C 10 Alkyl, C 6 -C 10 Aryl, C 7 -C 12 Aralkyl or C of (C) 7 -C 12 Alkylaryl groups of (a);
m+1 is less than or equal to 1 and less than or equal to 60, preferably m+1 is less than or equal to 1 and less than or equal to 30; p is more than or equal to 0 and less than or equal to 60, preferably more than or equal to 0 and less than or equal to 30; q is more than or equal to 0 and less than or equal to 60, preferably more than or equal to 0 and less than or equal to 30; x is not less than 1 and not more than 9, preferably not less than 1 and not more than 7, and each x can be the same or different.
In some embodiments, R is C 1 -C 3 For example methyl.
In some embodiments, Z is selected from
One or more of the following;
r is each independently selected from C 1 -C 10 Alkyl, C 6 -C 10 Aryl, C 7 -C 12 Aralkyl or C of (C) 7 -C 12 Alkylaryl groups of (a);
me represents methyl, ph represents phenyl; m+1 is less than or equal to 1 and less than or equal to 60, preferably m+1 is less than or equal to 1 and less than or equal to 30; p is more than or equal to 0 and less than or equal to 60, preferably more than or equal to 0 and less than or equal to 30; q is more than or equal to 0 and less than or equal to 60, preferably more than or equal to 0 and less than or equal to 30; x is not less than 1 and not more than 9, preferably not less than 1 and not more than 7, and each x can be the same or different.
In some embodiments, m is 0, 1, 2, 3,4, 5, 6, 7, 8, or 9.
In some embodiments, x is 1, 2, 3,4, 5, 6, or 7.
In some embodiments, the isocyanate-reactive compound is selected from the group consisting of
HO-(CH 2 ) 3 Si(OSi(CH 3 ) 3 ) 3 ；
HS-(CH 2 ) 3 Si(OSi(CH 3 ) 3 ) 3 ；
HO-(CH 2 ) 3 Si(CH 3 )(OSi(CH 3 ) 3 ) 2 ；
NH 2 -(CH 2 ) 3 Si(OSi(CH 3 ) 3 ) 3 ；
NH(CH 3 )-(CH 2 ) 3 Si(OSi(CH 3 ) 3 ) 3 ；
NH 2 -(CH 2 ) 3 Si(CH 3 )(OSi(CH 3 ) 3 ) 2 ；
NH(CH 3 )-(CH 2 ) 3 Si(CH 3 )(OSi(CH 3 ) 3 ) 2 ；
HO-(CH 2 ) 3 Si(OSi(CH 2 CH 3 ) 3 ) 3 ；
HO-CH 2 -Si(OSi(CH 3 ) 3 ) 3 ；
HO-(CH 2 ) 3 Si(CH 3 )[O-[Si(CH 3 ) 2 O]n-Si(CH 3 ) 2 C 4 H 9 ] 2 ，0≤n≤25；
HO-(CH 2 ) 3 [Si(CH 3 ) 2 O]n-Si(CH 3 ) 2 C 4 H 9 ，1≤n≤25；
HO-(CH 2 ) 3 [Si(CH 3 ) 2 O]n-Si(CH 3 ) 2 C 8 H 17 ，1≤n≤25；
HO-(CH 2 ) 3 [Si(CH 3 ) 2 O]n-Si(CH 3 ) 3 ，1≤n≤25；
NH 2 -(CH 2 ) 3 -[Si(CH 3 ) 2 O]n-Si(CH 3 ) 2 C 4 H 9 (C 4 H 9 Represents butyl), n is more than or equal to 1 and less than or equal to 25;
HO-(CH 2 ) 2 -NH-(CH 2 ) 3 Si(OSi(CH 3 ) 3 ) 3 ；
HO-(CH 2 ) 2 -NH-(CH 2 ) 3 [Si(CH 3 ) 2 O]n-Si(CH 3 ) 2 C 4 H 9 (C 4 H 9 represents butyl), n is more than or equal to 1 and less than or equal to 25;
NH[-(CH 2 ) 3 -Si(OSi(CH 3 ) 3 ) 3 ] 2 ；
NH[-(CH 2 ) 3 -Si(CH 3 )(OSi(CH 3 ) 3 ) 2 ] 2 ；
NH[-(CH 2 ) 3 -(Si(CH 3 ) 2 O) n -Si(CH 3 ) 2 C 4 H 9 ] 2 (C 4 H 9 represents butyl), n is more than or equal to 1 and less than or equal to 25.
In some embodiments, the isocyanate-reactive compounds include isocyanate-reactive compounds I-A and/or isocyanate-reactive compounds I-B;
the general formula of the compound I-A is the same as that of the formula I, and also satisfies Y when a is 1 1 And/or Y 2 Is of the formula (1), at least one Y when a is greater than 1 and less than or equal to 200 1 Is a structure of formula (1) and/or at least one Y 2 Is a structure of formula (1);
the general formula of the compounds I-B is the same as that of the formula I, and Y is also satisfied 1 And Y 2 Identical or different, each independently selected from C 1 -C 20 Alkyl, C of (2) 6 -C 20 Aryl, C of (2) 7 -C 12 Aralkyl and C of (C) 7 -C 12 Alkylaryl groups of (a).
In some embodiments, the compound I-A has the formula I-A:
M-Z 1 or Z is 1 -M-Z 1
Formula I-A
Wherein M is reactive with isocyanate;
Z 1 selected from the group consisting of the structures shown in the following,
Z 1 wherein R is 3 Each independently selected from C 1 -C 20 Alkyl, C of (2) 6 -C 20 Aryl, C of (2) 7 -C 12 Aralkyl of (C) 7 -C 12 Alkylaryl, C 1 -C 20 Alkoxy or R of (A) 4 -O-R 5 -a group, R 4 Is C 1 -C 20 Alkyl, C of (2) 6 -C 20 Aryl, C of (2) 7 -C 12 Aralkyl or C of (C) 7 -C 12 Alkylaryl group R of (2) 5 Is C 1 -C 20 An alkylene group of 1.ltoreq.a.ltoreq.200;
Y 1 and Y 2 Identical or different, each independently selected from C 1 -C 20 Alkyl, C of (2) 6 -C 20 Aryl, C of (2) 7 -C 12 Aralkyl of (C) 7 -C 12 And the structure of formula (1) below, provided that when a is 1, Y 1 And/or Y 2 Is of the formula (1), at least one Y when a is greater than 1 and less than or equal to 200 1 Is a structure of formula (1) and/or at least one Y 2 Is a structure of formula (1):
R 7 each independently selected from C 1 -C 20 Alkyl, C of (2) 6 -C 20 Aryl, C of (2) 7 -C 12 Aralkyl or C of (C) 7 -C 12 Alkylaryl groups of (a); r is R 8 Each independently selected from C 1 -C 20 Alkyl, C of (2) 6 -C 20 Aryl, C of (2) 7 -C 12 Aralkyl of (C) 7 -C 12 Alkylaryl, C 1 -C 20 Alkoxy or R 9 -O-R 10 -a group wherein R 9 Is C 1 -C 20 Alkyl, C of (2) 6 -C 20 Aryl, C of (2) 7 -C 12 Aralkyl or C of (C) 7 -C 12 Alkylaryl group R of (2) 10 Is C 1 -C 20 The alkylene group of (2) is more than or equal to 0 and less than or equal to 200.
The definition of M in formula I-A is the same as that of M in formula I.
In some embodiments, Z 1 Wherein R is 3 Each independently is C 1 -C 10 Alkyl, C of (2) 6 -C 10 Aryl, C of (2) 7 -C 12 Aralkyl of (C) 7 -C 12 Alkylaryl, C 1 -C 10 Alkoxy or R 4 -O-R 5 -a group, R 4 Is C 1 -C 10 Alkyl, C of (2) 6 -C 10 Aryl, C of (2) 7 -C 12 Aralkyl or C of (C) 7 -C 12 Alkylaryl group R of (2) 5 Is C 1 -C 10 An alkylene group of 1.ltoreq.a.ltoreq.100; r is R 7 Each independently is C 1 -C 10 Alkyl, C of (2) 6 -C 10 Aryl, C of (2) 7 -C 12 Aralkyl or C of (C) 7 -C 12 Alkylaryl groups of (a); r is R 8 Each independently is C 1 -C 10 Alkyl, C of (2) 6 -C 10 Aryl, C of (2) 7 -C 12 Aralkyl of (C) 7 -C 12 Alkylaryl, C 1 -C 10 Alkoxy or R 9 -O-R 10 -a group wherein R 9 Is C 1 -C 10 Alkyl, C of (2) 6 -C 10 Aryl, C of (2) 7 -C 12 Aralkyl or C of (C) 7 -C 12 Alkylaryl group R of (2) 10 Is C 1 -C 10 And/or 0.ltoreq.b.ltoreq.80.
According to some embodiments of the invention, Z 1 Wherein R is 3 Each independently is C 1 -C 6 Alkyl, C of (2) 6 -C 10 Aryl, C of (2) 7 -C 10 Aralkyl of (C) 7 -C 10 Alkylaryl, C 1 -C 6 Alkoxy or R 4 -O-R 5 -a group, R 4 Is C 1 -C 6 Alkyl, C of (2) 6 -C 10 Aryl, C of (2) 7 -C 10 Aralkyl or C of (C) 7 -C 10 Alkylaryl group R of (2) 5 Is C 1 -C 6 An alkylene group of 1.ltoreq.a.ltoreq.30; r is R 7 Each independently is C 1 -C 6 Alkyl, C of (2) 6 -C 10 Aryl, C of (2) 7 -C 10 Aralkyl or C of (C) 7 -C 10 Alkylaryl groups of (a); r is R 8 Each independently is C 1 -C 6 Alkyl, C of (2) 6 -C 10 Aryl, C of (2) 7 -C 10 Aralkyl of (C) 7 -C 10 Alkylaryl, C 1 -C 6 Alkoxy or R 9 -O-R 10 -a group which is a group,wherein R is 9 Is C 1 -C 6 Alkyl, C of (2) 6 -C 10 Aryl, C of (2) 7 -C 10 Aralkyl or C of (C) 7 -C 10 Alkylaryl group R of (2) 10 Is C 1 -C 16 The alkylene group of (2) is more than or equal to 0 and less than or equal to 30.
In some embodiments, in formula I-A, a is an integer from 1 to 80, an integer from 1 to 30, an integer from 1 to 20, or an integer from 1 to 10.
In some embodiments, b is 0 in formula I-A. In some embodiments, in formula I-A, b is an integer from 1 to 30, an integer from 1 to 20, an integer from 1 to 10, or an integer from 1 to 5.
Specifically indicated, R 3 ，R 8 Representative is C 1 -C 20 Alkyl of C 1 -C 20 Alkoxy, C 6 -C 20 Of the aryl radicals, in particular C 1 -C 8 Alkyl of C 1 -C 4 Alkoxy groups of (a). For example, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, methoxy, ethoxy, propoxy, butoxy, and the like. Aryl groups such as phenyl, tolyl, naphthyl, and the like. R is R 3 ，R 8 It is also possible to have such a structure (R 5 -O-R 6 )-，R 5 Is C 1 -C 10 Alkyl of R 6 Is C 1 -C 10 Alkylene groups of (2), more commonly such as CH 3 O(CH 2 ) x -and the like. R is R 6 Is a slave C 1 -C 20 Alkyl groups and C of (C) 6 -C 20 For example, an aryl group selected from the group consisting of methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, hexadecyl and the like, and an aryl group such as phenyl, tolyl, naphthyl and the like.
In some embodiments, Z 1 One or more selected from the following structures i-3 to i-6:
r is each independently selected from C 1 -C 10 Alkyl, C 6 -C 10 Aryl, C 7 -C 12 Aralkyl or C of (C) 7 -C 12 Alkylaryl groups of (a);
m+1 is less than or equal to 1 and less than or equal to 60, preferably m+1 is less than or equal to 1 and less than or equal to 30; p is more than or equal to 0 and less than or equal to 60, preferably more than or equal to 0 and less than or equal to 30; q is more than or equal to 0 and less than or equal to 60, preferably more than or equal to 0 and less than or equal to 30; x is not less than 1 and not more than 9, preferably not less than 1 and not more than 7, and each x can be the same or different.
In some embodiments, R is C 1 -C 3 For example methyl.
In some preferred embodiments, Z 1 Selected from the following structures:
one or more of the following;
me represents methyl, 1.ltoreq.m+1.ltoreq.60, preferably 1.ltoreq.m+1.ltoreq.30; p is more than or equal to 0 and less than or equal to 60, preferably more than or equal to 0 and less than or equal to 30; q is more than or equal to 0 and less than or equal to 60, preferably more than or equal to 0 and less than or equal to 30; x is not less than 1 and not more than 9, preferably not less than 1 and not more than 7, and each x can be the same or different.
In some embodiments, the isocyanate-reactive compound I-A is selected from
HO-(CH 2 ) 3 Si(OSi(CH 3 ) 3 ) 3 ；
HS-(CH 2 ) 3 Si(OSi(CH 3 ) 3 ) 3 ；
HO-(CH 2 ) 3 Si(CH 3 )(OSi(CH 3 ) 3 ) 2 ；
NH 2 -(CH 2 ) 3 Si(OSi(CH 3 ) 3 ) 3 ；
NH(CH 3 )-(CH 2 ) 3 Si(OSi(CH 3 ) 3 ) 3 ；
NH 2 -(CH 2 ) 3 Si(CH 3 )(OSi(CH 3 ) 3 ) 2 ；
NH(CH 3 )-(CH 2 ) 3 Si(CH 3 )(OSi(CH 3 ) 3 ) 2 ；
HO-(CH 2 ) 3 Si(OSi(CH 2 CH 3 ) 3 ) 3 ；
HO-CH 2 -Si(OSi(CH 3 ) 3 ) 3 ；
HO-(CH 2 ) 3 Si(CH 3 )[O-[Si(CH 3 ) 2 O]n-Si(CH 3 ) 2 C 4 H 9 ] 2 ，0≤n≤25
HO-(CH 2 ) 2 -NH-(CH 2 ) 3 Si(OSi(CH 3 ) 3 ) 3 ；
NH[-(CH 2 ) 3 -Si(OSi(CH 3 ) 3 ) 3 ] 2 ；
NH[-(CH 2 ) 3 -Si(CH 3 )(OSi(CH 3 ) 3 ) 2 ] 2 。
In some embodiments, compounds I-B have the formula I-B:
M-Z 2 or Z is 2 -M-Z 2
Formula I-B
Wherein M is reactive with isocyanate;
Z 2 selected from the group consisting of the structures shown in the following,
Z 2 in (1), Y 1 And Y 2 Identical or different, each independently selected from C 1 -C 20 Alkyl, C of (2) 6 -C 20 Aryl, C of (2) 7 -C 12 Aralkyl and C of (C) 7 -C 12 Alkylaryl groups of (a); r is R 3 Each independently selected from C 1 -C 20 Alkyl, C of (2) 6 -C 20 Aryl, C of (2) 7 -C 12 Aralkyl of (C) 7 -C 12 Alkylaryl, C 1 -C 20 Alkoxy or R of (A) 4 -O-R 5 -a group, R 4 Is C 1 -C 20 Alkyl, C of (2) 6 -C 20 Aryl, C of (2) 7 -C 12 Aralkyl or C of (C) 7 -C 12 Alkylaryl group R of (2) 5 Is C 1 -C 20 Is not less than 1 and not more than 200.
The definition of M in formulas I-B is the same as that of M in formula I.
In some embodiments, Z 2 In (1), Y 1 And Y 2 Identical or different, each independently selected from C 1 -C 10 Alkyl, C of (2) 6 -C 10 Aryl, C of (2) 7 -C 12 Aralkyl and C of (C) 7 -C 12 Alkylaryl groups of (a); r is R 3 Each independently selected from C 1 -C 10 Alkyl, C of (2) 6 -C 12 Aryl, C of (2) 7 -C 12 Aralkyl of (C) 7 -C 12 Alkylaryl, C 1 -C 10 Alkoxy or R of (A) 4 -O-R 5 -a group, R 4 Is C 1 -C 10 Alkyl, C of (2) 6 -C 12 Aryl, C of (2) 7 -C 12 Aralkyl or C of (C) 7 -C 12 Alkylaryl group R of (2) 5 Is C 1 -C 10 Alkylene groups of (a).
According to some embodiments of the invention, Z 2 In the formula, a is more than or equal to 1 and less than or equal to 80. According to some embodiments of the invention, Z 2 In the formula, a is more than or equal to 1 and less than or equal to 30. According to some embodiments of the invention, Z 2 In the formula, a is more than or equal to 1 and less than or equal to 20. According to some embodiments of the invention, Z 2 In the formula, a is more than or equal to 1 and less than or equal to 10.
In some embodiments, Z 2 In (1), Y 1 And Y 2 Identical or different, each independently selected from C 1 -C 6 Alkyl, C of (2) 6 -C 10 Aryl, C of (2) 7 -C 10 Aralkyl and C of (C) 7 -C 10 Alkylaryl groups of (a); r is R 3 Each independently selected from C 1 -C 6 Alkyl, C of (2) 6 -C 10 Aryl, C of (2) 7 -C 10 Aralkyl of (C) 7 -C 10 Alkylaryl, C 1 -C 6 Alkoxy or R of (A) 4 -O-R 5 -a group, R 4 Is C 1 -C 6 Alkyl, C of (2) 6 -C 10 Aryl, C of (2) 7 -C 10 Aralkyl or C of (C) 7 -C 10 Alkylaryl group R of (2) 5 Is C 1 -C 6 Alkylene groups of (a).
In some embodiments, Z 2 One or more selected from the following structures i-1 to i-2:
r is each independently selected from C 1 -C 10 Alkyl, C 6 -C 10 Aryl, C 7 -C 12 Aralkyl or C of (C) 7 -C 12 Alkylaryl groups of (a);
m+1 is less than or equal to 1 and less than or equal to 60, preferably m+1 is less than or equal to 1 and less than or equal to 30; x is more than or equal to 1 and less than or equal to 9, preferably x is more than or equal to 1 and less than or equal to 7.
Z 2 The following structure is preferred:
one or more of the following;
me represents methyl, ph represents phenyl; m+1 is less than or equal to 1 and less than or equal to 60, preferably m+1 is less than or equal to 1 and less than or equal to 30; x is more than or equal to 1 and less than or equal to 9, preferably x is more than or equal to 1 and less than or equal to 7.
In some embodiments, the isocyanate-reactive compound I-B is selected from
HO-(CH 2 ) 3 [Si(CH 3 ) 2 O]n-Si(CH 3 ) 2 C 4 H 9 ，1≤n≤25；
HO-(CH 2 ) 3 [Si(CH 3 ) 2 O]n-Si(CH 3 ) 2 C 8 H 17 ，1≤n≤25；
HO-(CH 2 ) 3 [Si(CH 3 ) 2 O]n-Si(CH 3 ) 3 ，1≤n≤25；
NH 2 -(CH 2 ) 3 -[Si(CH 3 ) 2 O]n-Si(CH 3 ) 2 C 4 H 9 (C 4 H 9 Represents butyl), n is more than or equal to 1 and less than or equal to 25;
HO-(CH 2 ) 2 -NH-(CH 2 ) 3 [Si(CH 3 ) 2 O]n-Si(CH 3 ) 2 C 4 H 9 (C 4 H 9 represents butyl), n is more than or equal to 1 and less than or equal to 25;
NH[-(CH 2 ) 3 -(Si(CH 3 ) 2 O) n -Si(CH 3 ) 2 C 4 H 9 ] 2 (C 4 H 9 represents butyl), n is more than or equal to 1 and less than or equal to 25.
In some embodiments, the compounds of the present application are formed by reacting an isocyanate group-containing compound with a Zerewitinoff hydrogen atom-containing organosilicon compound in a molar ratio of isocyanate groups to active hydrogen atoms of from 0.5:1 to 1.5:1, preferably from 0.8:1 to 1.2:1.
In some embodiments, the synthesis of the compounds of the present application is performed in a suitable dry organic solvent without groups reactive with isocyanate groups. Ketones are preferred solvents, with methyl isobutyl ketone (MIBK) being particularly preferred. In some embodiments, the compounds of the present application can be dispersed and emulsified with emulsifiers, co-solvents, water, and the like, by a high speed homogenizing and emulsifying machine to provide a uniform and stable emulsion.
In a second aspect, the present application provides a treatment agent comprising a compound according to the first aspect, an emulsifier and an aqueous medium.
In some embodiments, the emulsifier is selected from one or more of a nonionic surfactant, an anionic surfactant, a cationic surfactant, an N-oxide, and an amphoteric surfactant.
In some embodiments, the nonionic surfactant is selected from one or more of ethers, esters, ester ethers, alkanolamides, polyols, and amine oxide surfactants. In some embodiments, the nonionic surfactant is a nonionic surfactant having an oxyalkylene group.
In some embodiments, the nonionic surfactant may be one or more of alkylene oxide adducts of linear and/or branched aliphatic groups, polyalkylene glycol esters of linear and/or branched fatty acids, polyoxyethylene (POE)/polyoxypropylene (POP) copolymers (random or block copolymers), alkylene oxide adducts of acetylenic diols.
In some embodiments, the nonionic surfactant includes addition products of ethylene oxide with hexylphenol, isooctylphenol, cetyl alcohol, oleic acid, an alkyl (C12-C16) thiol, sorbitan mono fatty acid (C7-C9) or (C12-C18) amine, and the like.
In some embodiments, the cationic surfactant is selected from one or more of amines, amine salts, delegate amine salts, imidazolines, and imidazolinium salt surfactants.
In some embodiments, examples of cationic surfactants are R 1 -N + (R 2 R 3 R 4 )X - Wherein R is 1 、R 2 、R 3 And R is 4 Independently of one another, are identical or different hydrogen atoms or hydrocarbon radicals having 1 to 50 carbon atoms (e.g. C 1 -C 6 Alkyl, C 7 -C 10 Alkyl, C 11 -C 15 Alkyl or C 16 -C 20 Alkyl), an aryl group having 6 to 50 carbon atoms, an aralkyl group having 7 to 50 carbon atoms, or an alkylaryl group having 7 to 50 carbon atoms, and X is a halogen (for example, chlorine or bromine), an acid (for example, an inorganic acid such as hydrochloric acid, or an organic acid (particularly, a fatty acid) such as acetic acid).
In some embodiments, the cationic surfactant includes one or more of dodecyl trimethyl ammonium acetate, tetradecyl trimethyl ammonium chloride, hexadecyl trimethyl ammonium bromide, trimethyl octadecyl ammonium chloride, and stearamidopropyl dimethylamine.
In some embodiments, the emulsifiers are nonionic surfactants and cationic surfactants.
In some embodiments, the emulsifier is used in an amount of 0.1 to 20 parts by weight relative to 100 parts by weight of the compound.
In some embodiments, the aqueous medium comprises water and optionally an organic solvent. In some embodiments, the aqueous medium is preferably water. The aqueous medium may be mixed with water and an organic solvent as required, and the organic solvent is not particularly limited as long as it is a water-miscible organic solvent, and examples thereof include acetone, methyl ethyl ketone, ethyl acetate, ethanol, isopropyl alcohol, butyl diglycol, propylene glycol, dipropylene glycol, tripropylene glycol, dipropylene glycol monomethyl ether, tripropylene glycol monomethyl ether, dipropylene glycol monobutyl ether, dipropylene glycol dimethyl ether, propylene glycol monomethyl ether acetate, and the like. The ratio of water to the organic solvent is not particularly limited.
In a third aspect, the present application provides a process for preparing a treatment agent according to the second aspect, comprising mixing a solution comprising a compound according to the first aspect with a solution comprising an emulsifier and water.
In some embodiments, the method of preparing the treatment agent comprises the steps of:
(1) Reacting an isocyanate group-containing compound with an isocyanate-reactive compound in the presence of a solvent and a catalyst to obtain a reaction product;
(2) Mixing the reaction product of (1) with a solution containing an emulsifier and water, and removing the solvent to obtain the treating agent.
In some embodiments, the method of treating a subject comprises the steps of:
(1) Adding a solvent, a compound containing isocyanate groups, an isocyanate-reactive compound and a catalyst into a reaction kettle, heating to a certain temperature, and reacting for a period of time until the isocyanate functional groups are basically reacted completely;
(2) Mixing emulsifier and water to form emulsifier solution, slowly adding into the above obtained compound, homogenizing in high pressure homogenizer to obtain stable emulsion, and removing solvent by vacuum distillation to obtain the final product.
In some embodiments, the solvent is selected from one or more of acetone, methyl ethyl ketone, ethyl acetate, ethanol, isopropanol, butyl diglycol, propylene glycol, dipropylene glycol, tripropylene glycol, dipropylene glycol monomethyl ether, tripropylene glycol monomethyl ether, dipropylene glycol monobutyl ether, dipropylene glycol dimethyl ether, and propylene glycol monomethyl ether acetate.
In some embodiments, the catalyst is selected from one or more of ferric chloride, dibutyltin dilaurate, and sodium carbonate.
In a fourth aspect, the present application provides the use of a compound according to the first aspect or a treatment according to the second aspect or a treatment prepared by a method according to the third aspect in a fibrous web, leather, non-woven, asbestos, fur, concrete, stone, paper products, plastics or paint.
In a fifth aspect, the present application provides a water-repellent oil-repellent or stain-repellent product comprising a product and a compound according to the first aspect or a treating agent according to the second aspect or a treating agent prepared by a method according to the third aspect, said product being a fibrous fabric, leather, nonwoven, asbestos, fur, concrete, stone, paper product, plastic or paint.
In some embodiments, the compound of the first aspect or the treatment agent of the second aspect or the treatment agent prepared by the method of the third aspect is attached to the surface and/or the interior of the product.
In a sixth aspect, the present application provides a method of treating a product comprising contacting the product with a compound according to the first aspect or a treating agent according to the second aspect or a treating agent prepared by a method according to the third aspect, the product being a fibrous fabric, leather, non-woven fabric, asbestos, fur, concrete, stone, paper product, plastic or paint.
In some embodiments, the contacting is achieved by a surface sizing process, a surface coating process, a wet end addition process, or a soaking treatment process.
The treating agent of the present application can be applied to an object to be treated by a conventionally known method. In general, the treatment agent is diluted in an organic solvent or water, and is applied to the surface of the object to be treated by a known method such as dip coating, spray coating, or foam, followed by drying. In addition, vulcanization may be applied with a suitable crosslinking agent (e.g., blocked isocyanate) if desired. Insect repellent, softener, antibacterial agent, flame retardant, antistatic agent, crease-resist agent, etc. may be added to the treatment agent of the present application. The concentration of the compound in the treatment liquid in contact with the substrate may be 0.01 to 10% by weight (particularly in the case of dip coating), for example, 0.05 to 10% by weight.
In the present application, the fiber fabric includes animal or plant natural fibers such as cotton, hemp, wool, silk, etc., synthetic fibers such as polyamide, polyester, polyvinyl alcohol, polyacrylonitrile, polyvinyl chloride, polypropylene, acrylic fibers, semi-synthetic fibers such as rayon and acetate fibers, inorganic fibers such as glass fibers, carbon fibers, asbestos fibers, etc., or mixed fiber fabrics thereof.
ADVANTAGEOUS EFFECTS OF INVENTION
The compound and the generated treating agent can be applied to surface treatment of various articles such as fiber fabrics, leather, non-woven fabrics, asbestos, fur, concrete, natural stone, paper, plastics or paint under acidic, alkaline and neutral conditions. The treatment modes comprise soaking, surface coating, surface sizing, internal addition (wet end addition) and the like, and the treatment modes can endow the surface of the article with excellent water and oil repellent performance or antifouling performance after the treatment.
Detailed Description
In order to make the objects, technical solutions and advantages of the present application more apparent, the present application will be further described in detail with reference to the following examples. These examples are only for the purpose of explaining the present application and are not intended to constitute any limitation to the present application. The actual scope of the application is set forth in the following claims.
Unless otherwise indicated herein, the terms used herein have their ordinary meanings as known to those skilled in the art.
In this application, the term "alkyl" refers to a straight chain alkyl or branched alkyl group, non-limiting examples of which include: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, 1-ethylpropyl, 2-methylbutyl, 3-methylbutyl, 2-dimethylpropyl, n-hexyl, 2-methylpentyl, 3-methylpentyl, and the like.
In this application, the term "alkylene" refers to a straight chain alkylene or branched chain alkylene, non-limiting examples of which include: methylene, ethylene, n-propylene, n-butylene, n-pentylene, -CHCH 3 CH 2 -、-CHCH 3 CH 2 CH 2 -、CH 2 CH 3 CHCH 2 -and the like.
In the present application, "%" means mass percent unless otherwise specified.
1. Synthesis method
(1) Adding a solvent, a compound containing isocyanate groups, an isocyanate-reactive compound and a catalyst into a reaction kettle, heating to a certain temperature, and reacting for a period of time until the isocyanate functional groups are basically reacted completely;
(2) Mixing emulsifier and water to form emulsifier solution, slowly adding into the above obtained compound, homogenizing in high pressure homogenizer to obtain stable emulsion, and removing solvent by vacuum distillation to obtain the final product.
2. Test method
Treatment of fibrous fabrics
The fabrics treated in this application may be dyed 100% polyester fabrics and 100% kaki fabrics. The treatment method comprises the following steps: the cloth sample was placed into an aqueous solution containing a concentration of the treating agent of the present application for padding treatment (stock absorption of 70%), and then dried at 110 ℃ for 90 seconds and baked at 170 ℃ for 60 seconds. The sample cloth was evaluated for water repellency, and oil repellency.
Evaluation method
Method for testing water resistance of fiber fabrics
According to the Teflon global specification and quality control test method, the samples are tested by using liquids with different isopropanol volume contents, and the degree of surface wetting is observed and determined. This test provides a rough index of resistance to water staining. The higher the repellency rating, the better the resistance of the final substrate to water-based materials, the composition of the standard test liquids is shown in table 1 below,
table 1 Water resistance test grade composition
| Water resistance rating | Composition by volume, isopropanol | Make up volume percent, water |
| 1 | 2 | 98 |
| 2 | 5 | 95 |
| 3 | 10 | 90 |
| 4 | 20 | 80 |
| 5 | 30 | 70 |
| 6 | 40 | 60 |
| 7 | 50 | 50 |
| 8 | 60 | 40 |
| 9 | 70 | 30 |
| 10 | 80 | 20 |
| 11 | 90 | 10 |
| 12 | 100 | 0 |
Method for testing fiber fabrics-spray water repellency test
The dynamic water resistance of the treated substrates was measured according to the American textile dyeing chemical Association (AATCC) TM-22, reference being made to published standards. A glass funnel having a volume of at least 250ml and a nozzle capable of ejecting 250ml of water in 20-30 seconds was used. The test piece frame was a metal frame having a diameter of 15 cm. 3 test pieces having a size of about 20cmX cm were prepared, and the pieces were fixed to a test piece holder frame so that the pieces were free from wrinkles. The center of the spray was centered on the sheet, room temperature water (250 ml) was added to the glass funnel and sprayed onto the test sheet (for 25 seconds to 30 seconds). The holding frame is removed from the table, one end of the frame is grasped, the underside of the front face is brought into contact with the opposite end with a hard object. The same procedure was repeated while the rotation was maintained at 180 ° again, so that the excessive water droplets were dropped. Wet test pieces were given scores of 0, 50, 70, 80, 90, 100 in the order of starting poor water repellency (as shown in table 2 below). Comparison was made with a wet comparison standard. The results were obtained from the average of 3 determinations.
Table 2 Water repellency rating table
| Water repellency No. | Status of |
| 100 | The surface is free from wetting or adhesion of water drops |
| 90 | The surface is not moist but exhibits the adhesion of small water droplets |
| 80 | The surface presents a small, individual drop-like wetting |
| 70 | Half of the surface is moist and assumes the state of a small, individually moist, permeable cloth |
| 50 | The surface as a whole is moist |
| 0 | The surface and the back are integrally wet |
Method for testing oil resistance of fiber fabrics
The oil repellency was evaluated according to the test method of AATCC-TM118, the basic principle being to apply test oil drops of different surface tension to the test cloth, the higher the rating, the better the oil repellency, the composition of the standard test liquid being shown in Table 3 below.
Table 3 fabric oil repellency test grade composition
| Oil resistance grade | Test solution | Surface tension mN/m |
| 8 | N-heptane | 20.0 |
| 7 | N-octane | 21.8 |
| 6 | N-decane | 23.5 |
| 5 | N-dodecane | 25.0 |
| 4 | N-tetradecane | 26.7 |
| 3 | N-hexadecane | 27.3 |
| 2 | 65 parts of liquid paraffin and 35 parts of n-hexadecane | 29.6 |
| 1 | Liquid paraffin | 31.2 |
Three examples and comparative examples
Abbreviations for chemicals see table 4:
table 4 codes and formulas of the respective compounds
Example 1
Step (1) 65 g (340 mmol NCO) of a four-necked flask equipped with a reflux condenser, a nitrogen inlet tube, a thermometer and a stirrer was charged withHB-100 (hexamethylene diisocyanate-based biuret polyisocyanate) was dissolved in 100 g of methyl isobutyl ketone (abbreviated as MIBK) under nitrogen blanket gas, and 121 g (340 mmol) of Si-B3-OH was then added. Heated to 55℃and then 0.025 g of Er in 2 ml of MIBK was addedThe solution of tin butyldilaurate was further heated to 95℃and reacted for 6 hours.
Step (2) 450 g of water, 7.8 g of stearamidopropyl dimethylamine, 4 g of fatty alcohol polyoxyethylene ether (EO number 9), 42 g of dipropylene glycol and 4.7 g of acetic acid were added to a beaker and stirred to form a uniform surfactant solution. The solution was heated to 65 ℃, the reaction mixture in step (1) was cooled to 65 ℃ and the surfactant solution was slowly added to produce a milky solution. The mixture was blended (2 minutes) by an immersion mixer and homogenized at 6000psi, followed by evaporation under reduced pressure to remove MIBK to give a dispersion. The solids content of the dispersion was adjusted to 25% by make-up water.
Example 2-example 6
As in example 1, except that Si-B3-OH, si-B3-SH (example 2), si-B3-NHM (example 3), si-B2-OH (example 4), si-N2-B2-NH (example 5), si-5-OH (example 6), the solids content of the dispersion was set to about 25% by the amount of water supplied in the last step.
Example 7
Step (1) 65 g (340 mmol NCO) of a four-necked flask equipped with a reflux condenser, a nitrogen inlet tube, a thermometer and a stirrer was charged withHT-100 (HDI trimer) was dissolved in 100 g of methyl isobutyl ketone (MIBK) under nitrogen blanket, and 121 g (340 mmol) of Si-B3-OH was added. Heated to 55℃and then a solution of 0.025 g of dibutyltin dilaurate in 2 ml of MIBK was added and the mixture was further heated to 95℃and reacted for 6 hours.
Step (2) 450 g of water, 7.8 g of stearamidopropyl dimethylamine, 4 g of fatty alcohol polyoxyethylene ether (EO number 9), 42 g of dipropylene glycol and 4.7 g of acetic acid were added to a beaker and stirred to form a uniform surfactant solution. The solution was heated to 65 ℃, the reaction mixture in step (1) was cooled to 65 ℃ and the surfactant solution was slowly added to produce a milky solution. The mixture was blended (2 minutes) by an immersion mixer and homogenized at 6000psi, followed by evaporation under reduced pressure to remove MIBK to give a dispersion. The solids content of the dispersion was adjusted to 25% by make-up water.
Example 8
Step (1) into a four-necked flask equipped with a reflux condenser, a nitrogen inlet tube, a thermometer and a stirrer, 84 g (340 mmol NCO) was chargedIT-100 (IPDI trimer) was dissolved in 100 g of methyl isobutyl ketone (abbreviated as MIBK) under nitrogen blanket, and 121 g (340 mmol) of Si-B3-OH was added. Heated to 55℃and then a solution of 0.025 g of dibutyltin dilaurate in 2 ml of MIBK was added and the mixture was further heated to 95℃and reacted for 6 hours.
Step (2) 450 g of water, 7.8 g of stearamidopropyl dimethylamine, 4 g of fatty alcohol polyoxyethylene ether (EO number 9), 42 g of dipropylene glycol and 4.7 g of acetic acid were added to a beaker and stirred to form a uniform surfactant solution. The solution was heated to 65 ℃, the reaction mixture in step (1) was cooled to 65 ℃ and the surfactant solution was slowly added to produce a milky solution. The mixture was blended (2 minutes) by an immersion mixer and homogenized at 6000psi, followed by evaporation under reduced pressure to remove MIBK to give a dispersion. The solids content of the dispersion was adjusted to 25% by make-up water.
Example 9
Step (1) into a four-necked flask equipped with a reflux condenser, a nitrogen inlet tube, a thermometer and a stirrer, 53 g (340 mmol of NCO) was chargedIPP (IPDI prepolymer) was dissolved in 100 g of methyl isobutyl ketone (abbreviated as MIBK) under nitrogen blanket gas, and 121 g (340 mmol) of Si-B3-OH was added. Heated to 55℃and then a solution of 0.025 g of dibutyltin dilaurate in 2 ml of MIBK was added and the mixture was further heated to 95℃and reacted for 6 hours.
Step (2) 450 g of water, 7.8 g of stearamidopropyl dimethylamine, 4 g of fatty alcohol polyoxyethylene ether (EO number 9), 42 g of dipropylene glycol and 4.7 g of acetic acid were added to a beaker and stirred to form a uniform surfactant solution. The solution was heated to 65 ℃, the reaction mixture in step (1) was cooled to 65 ℃ and the surfactant solution was slowly added to produce a milky solution. The mixture was blended (2 minutes) by an immersion mixer and homogenized at 6000psi, followed by evaporation under reduced pressure to remove MIBK to give a dispersion. The solids content of the dispersion was adjusted to 25% by make-up water.
Textile testing of the above dispersion: 100% polyester cloth and 100% cotton cloth were selected, respectively, the dispersion was diluted with tap water to 5%,3% and 2% (dispersion content) liquids, subjected to padding treatment (absorption rate 70%), and then dried at 110℃for 90 seconds and baked at 170℃for 60 seconds. The water repellency, and oil repellency of the resulting swatches were evaluated and the results are shown in Table 5.
Table 5 performance test table
As can be seen from Table 5, the dispersions obtained in examples 1-9 of the present application each impart good oil and water repellency properties to polyester or cotton fabrics, and in particular the dispersions (i.e., treatments) comprising compound I-A are more excellent than the treatments comprising compound I-B.
Comparative example 1
Step (1) 65 g (340 mmol NCO) of a four-necked flask equipped with a reflux condenser, a nitrogen inlet tube, a thermometer and a stirrer was charged withHB-100 (hexamethylene diisocyanate-based biuret polyisocyanate) was dissolved in 100 g of methyl isobutyl ketone (abbreviated as MIBK) under nitrogen blanket gas, and 92 g (340 mmol) of StA-OH was then added. Heated to 55℃and then a solution of 0.025 g of dibutyltin dilaurate in 2 ml of MIBK was added and the mixture was further heated to 95℃and reacted for 6 hours.
Step (2) 450 g of water, 7.8 g of stearamidopropyl dimethylamine, 4 g of fatty alcohol polyoxyethylene ether (EO number 9), 42 g of dipropylene glycol and 4.7 g of acetic acid were added to a beaker and stirred to form a uniform surfactant solution. The solution was heated to 65 ℃, the reaction mixture in step (1) was cooled to 65 ℃ and the surfactant solution was slowly added to produce a milky solution. The mixture was blended (2 minutes) by an immersion mixer and homogenized at 6000psi, followed by evaporation under reduced pressure to remove MIBK to give a dispersion. The solids content of the dispersion was adjusted to 25% by make-up water.
Comparative example 2
Polyester polyol (Qingdao New chemical Co., ltd., trade name 7112T,1.5 g), isocyanate IPDI (11.1 g) and a double OH-terminated polysiloxane SF8427 (Dow chemical, 31 g) were charged into a three-necked flask and mixed at 80℃for 1 hour, and then 0.2g of dibutyltin dilaurate as a catalyst was added to the flask to start the reaction. The reaction was continued for two hours to yield a first prepolymerized intermediate. Dimethylolpropionic acid (1.68 g) was added to the flask and reacted for 2 hours. The first pre-polymerized intermediate was cooled to 40 ℃ and neutralized with triethanolamine (1.26 g) for 30 minutes. A small amount of acetone was added to the flask during the above process to maintain the viscosity of the reaction system at about 500cps. The flask was cooled to room temperature and 135g of an aqueous solution of ethylenediamine (0.83 g) was added to the flask with vigorous stirring to form a dispersion. Finally, the acetone was removed from the dispersion by distillation under reduced pressure, the solids content of the dispersion being adjusted to 25% by supplementing water.
Performance tests were conducted according to the test methods of examples 1 to 9, and the results are shown in Table 6.
Table 6 performance test table
The dispersions obtained in examples 1-9 of the present application, together with the performance test results of tables 5, 6, impart good oil and water repellency properties to fibrous fabrics, and in particular the treatment comprising compound I-A provides better oil and water repellency properties than the treatment comprising compound I-B.
The treatment agent obtained by reacting the long carbon chain with isocyanate in comparative example 1 has better water repellency but no oil repellency.
Comparative example 2 uses a dihydroxy terminated polysiloxane as the primary reactant and the results show that the treatment has some water repellency but no oil repellency in the fibrous web.
The technical solution of the present application is not limited to the above specific embodiments, and all technical modifications made according to the technical solution of the present application fall within the protection scope of the present application.
Claims (13)
1. A compound prepared from isocyanate group-containing compound and isocyanate-reactive compound represented by formula I,
M-Z or Z-M-Z
I is a kind of
Wherein M is reactive with isocyanate;
z is selected from the structures shown in the following,
in Z, R 3 Each independently selected from C 1 -C 20 Alkyl, C of (2) 6 -C 20 Aryl, C of (2) 7 -C 12 Aralkyl of (C) 7 -C 12 Alkylaryl, C 1 -C 20 Alkoxy or R of (A) 4 -O-R 5 -a group, R 4 Is C 1 -C 20 Alkyl, C of (2) 6 -C 20 Aryl, C of (2) 7 -C 12 Aralkyl or C of (C) 7 -C 12 Alkylaryl group R of (2) 5 Is C 1 -C 20 An alkylene group of 1.ltoreq.a.ltoreq.200;
Y 1 and Y 2 Identical or different, each independently selected from C 1 -C 20 Alkyl, C of (2) 6 -C 20 Aryl, C of (2) 7 -C 12 Aralkyl of (C) 7 -C 12 Alkylaryl groups of (C) or e.gThe structure of the following formula (1):
R 7 each independently selected from C 1 -C 20 Alkyl, C of (2) 6 -C 20 Aryl, C of (2) 7 -C 12 Aralkyl or C of (C) 7 -C 12 Alkylaryl groups of (a); r is R 8 Each independently selected from C 1 -C 20 Alkyl, C of (2) 6 -C 20 Aryl, C of (2) 7 -C 12 Aralkyl of (C) 7 -C 12 Alkylaryl, C 1 -C 20 Alkoxy or R 9 -O-R 10 -a group wherein R 9 Is C 1 -C 20 Alkyl, C of (2) 6 -C 20 Aryl, C of (2) 7 -C 12 Aralkyl or C of (C) 7 -C 12 Alkylaryl group R of (2) 10 Is C 1 -C 20 The alkylene group of (2) is more than or equal to 0 and less than or equal to 200.
2. The compound according to claim 1, wherein the isocyanate group-containing compound is selected from one or more of hexamethylene diisocyanate homopolymer, 3-isocyanatomethyl-3, 4-trimethylcyclohexyl isocyanate, bis- (4-isocyanatocyclohexyl) methane, diisocyanate trimer represented by formulas II a to II e, polymeric diphenylmethane diisocyanate represented by formula II f and isophorone diisocyanate prepolymer represented by formula II g,
in the formula II f, n is 0-10, and in the formula II g, n is 0-10.
3. A compound according to claim 1 or 2, wherein the group M of formula I contains one or more Zerewitinoff hydrogen atoms.
4. A compound according to any one of claims 1 to 3, wherein M is as shown in formula I-1:
H-X-B-
formula I-1
In formula I-1, B is selected from C 1 -C 20 Alkylene group, C 6 -C 20 Arylene groups of (a) and combinations thereof; x is-O-, -S-, -N (R) 1 )-，-O-(CH 2 ) k -N(R 2 )-，-O-C(O)-，R 1 Selected from hydrogen atoms or C 1 -C 20 Alkyl, R 2 Selected from hydrogen atoms or C 1 -C 20 Alkyl, k is more than or equal to 1 and less than or equal to 6;
and/or
M is shown as a formula I-2:
in formula I-2, B is selected from C 1 -C 20 Alkylene group, C 6 -C 20 Arylene groups of (a) and combinations thereof.
5. A compound according to any one of claims 1 to 4, wherein:
the isocyanate-reactive compounds include isocyanate-reactive compounds I-A and/or isocyanate-reactive compounds I-B;
the general formula of the compound I-A is the same as that of the formula I, and also satisfies Y when a is 1 1 And/or Y 2 Is of the formula (1), at least one Y when a is greater than 1 and less than or equal to 200 1 Is a structure of formula (1) and/or at least one Y 2 Is a structure of formula (1);
the general formula of the compounds I-B is the same as that of the formula I, and Y is also satisfied 1 And Y 2 Identical or different, each independently selected from C 1 -C 20 Alkyl, C of (2) 6 -C 20 Aryl, C of (2) 7 -C 12 Aralkyl and C of (C) 7 -C 12 Alkylaryl groups of (a).
6. A compound according to any one of claims 1 to 5,
in the formula I-1, B is C 1 -C 10 Alkylene of (C), preferably B is C 1 -C 6 An alkylene group of (a); x, R 1 Selected from hydrogen atoms or C 1 -C 10 Alkyl, preferably R 1 Selected from a hydrogen atom or a methyl group;
in the formula I-2, B is C 1 -C 10 Alkylene of (C), preferably B is C 1 -C 6 An alkylene group of (a);
in Z, R 3 Each independently is C 1 -C 10 Alkyl, C of (2) 6 -C 10 Aryl, C of (2) 7 -C 12 Aralkyl of (C) 7 -C 12 Alkylaryl, C 1 -C 10 Alkoxy or R 4 -O-R 5 -a group, R 4 Is C 1 -C 10 Alkyl, C of (2) 6 -C 10 Aryl, C of (2) 7 -C 12 Aralkyl or C of (C) 7 -C 12 Alkylaryl group R of (2) 5 Is C 1 -C 10 An alkylene group of 1.ltoreq.a.ltoreq.100; r is R 7 Each independently is C 1 -C 10 Alkyl, C of (2) 6 -C 10 Aryl, C of (2) 7 -C 12 Aralkyl or C of (C) 7 -C 12 Alkylaryl groups of (a); r is R 8 Each independently is C 1 -C 10 Alkyl, C of (2) 6 -C 10 Aryl, C of (2) 7 -C 12 Aralkyl of (C) 7 -C 12 Alkylaryl, C 1 -C 10 Alkoxy or R 9 -O-R 10 -a group wherein R 9 Is C 1 -C 10 Alkyl, C of (2) 6 -C 10 Aryl, C of (2) 7 -C 12 Aralkyl or C of (C) 7 -C 12 Alkylaryl group R of (2) 10 Is C 1 -C 10 And b is more than or equal to 0 and less than or equal to 100.
7. The compound of any one of claims 1-6, wherein each Z is independently selected from one or more of the following structures i-1 to i-6:
z is preferably from
One or more of the following;
r is each independently selected from C 1 -C 10 Alkyl, C 6 -C 10 Aryl, C 7 -C 12 Aralkyl or C of (C) 7 -C 12 Alkylaryl groups of (a);
me represents methyl, ph represents phenyl; m+1 is less than or equal to 1 and less than or equal to 60, preferably m+1 is less than or equal to 1 and less than or equal to 30; p is more than or equal to 0 and less than or equal to 60, preferably more than or equal to 0 and less than or equal to 30; q is more than or equal to 0 and less than or equal to 60, preferably more than or equal to 0 and less than or equal to 30; x is not less than 1 and not more than 9, preferably not less than 1 and not more than 7, and each x can be the same or different.
8. A compound according to any one of claims 1 to 7,
the isocyanate-reactive compound I-A is selected from
HO-(CH 2 ) 3 Si(OSi(CH 3 ) 3 ) 3 ；
HS-(CH 2 ) 3 Si(OSi(CH 3 ) 3 ) 3 ；
HO-(CH 2 ) 3 Si(CH 3 )(OSi(CH 3 ) 3 ) 2 ；
NH 2 -(CH 2 ) 3 Si(OSi(CH 3 ) 3 ) 3 ；
NH(CH 3 )-(CH 2 ) 3 Si(OSi(CH 3 ) 3 ) 3 ；
NH 2 -(CH 2 ) 3 Si(CH 3 )(OSi(CH 3 ) 3 ) 2 ；
NH(CH 3 )-(CH 2 ) 3 Si(CH 3 )(OSi(CH 3 ) 3 ) 2 ；
HO-(CH 2 ) 3 Si(OSi(CH 2 CH 3 ) 3 ) 3 ；
HO-CH 2 -Si(OSi(CH 3 ) 3 ) 3 ；
HO-(CH 2 ) 3 Si(CH 3 )[O-[Si(CH 3 ) 2 O]n-Si(CH 3 ) 2 C 4 H 9 ] 2 ，0≤n≤25；
HO-(CH 2 ) 2 -NH-(CH 2 ) 3 Si(OSi(CH 3 ) 3 ) 3 ；
NH[-(CH 2 ) 3 -Si(OSi(CH 3 ) 3 ) 3 ] 2 ；
NH[-(CH 2 ) 3 -Si(CH 3 )(OSi(CH 3 ) 3 ) 2 ] 2 ；
And/or
The isocyanate-reactive compounds I-B are selected from
HO-(CH 2 ) 3 [Si(CH 3 ) 2 O]n-Si(CH 3 ) 2 C 4 H 9 ，1≤n≤25；
HO-(CH 2 ) 3 [Si(CH 3 ) 2 O]n-Si(CH 3 ) 2 C 8 H 17 ，1≤n≤25；
HO-(CH 2 ) 3 [Si(CH 3 ) 2 O]n-Si(CH 3 ) 3 ，1≤n≤25；
NH 2 -(CH 2 ) 3 -[Si(CH 3 ) 2 O]n-Si(CH 3 ) 2 C 4 H 9 (C 4 H 9 Represents butyl), n is more than or equal to 1 and less than or equal to 25;
HO-(CH 2 ) 2 -NH-(CH 2 ) 3 [Si(CH 3 ) 2 O]n-Si(CH 3 ) 2 C 4 H 9 (C 4 H 9 represents butyl), n is more than or equal to 1 and less than or equal to 25;
NH[-(CH 2 ) 3 -(Si(CH 3 ) 2 O) n -Si(CH 3 ) 2 C 4 H 9 ] 2 (C 4 H 9 represents butyl), n is more than or equal to 1 and less than or equal to 25.
9. A treatment agent comprising a compound according to any one of claims 1 to 8, an emulsifier and an aqueous medium, preferably the aqueous medium comprises water and optionally an organic solvent.
10. A process for preparing a treatment agent according to claim 9, comprising mixing a solution comprising a compound according to any one of claims 1-8 with a solution comprising an emulsifier and water, preferably comprising the steps of:
(1) Reacting an isocyanate group-containing compound with an isocyanate-reactive compound in the presence of a solvent and a catalyst to obtain a reaction product;
(2) Mixing the reaction product in (1) with a solution containing an emulsifier and water, homogenizing, and removing the solvent to obtain the treating agent.
11. Use of a compound according to any one of claims 1 to 8 or a treatment agent according to claim 9 or a treatment agent prepared by a method according to claim 10 in a fibre fabric, leather, non-woven fabric, asbestos, fur, concrete, stone, paper products, plastics or paint.
12. A water-repellent oil-repellent or stain-repellent product comprising a product which is a fibrous fabric, leather, nonwoven, asbestos, fur, concrete, stone, paper product, plastic or paint, and a compound according to any one of claims 1 to 8 or a treatment agent according to claim 9 or a treatment agent prepared by a method according to claim 10,
preferably, a compound according to any one of claims 1 to 8 or a treatment agent according to claim 9 or a treatment agent prepared by a method according to claim 10 is attached to the surface and/or the interior of the product.
13. A method for treating a product comprising contacting the product with a compound according to any one of claims 1 to 8 or a treating agent according to claim 9 or a treating agent prepared by a method according to claim 10, said product being a fibrous fabric, leather, nonwoven fabric, asbestos, fur, concrete, stone, paper product, plastic or paint,
preferably, the contacting is achieved by a surface sizing process, a surface coating process, a wet end addition process, or a soaking treatment process.
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