CN106459607A - 得自反应性染料的有机着色剂复合物和包含其的制品 - Google Patents
得自反应性染料的有机着色剂复合物和包含其的制品 Download PDFInfo
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- CN106459607A CN106459607A CN201580026689.8A CN201580026689A CN106459607A CN 106459607 A CN106459607 A CN 106459607A CN 201580026689 A CN201580026689 A CN 201580026689A CN 106459607 A CN106459607 A CN 106459607A
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- red
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- NOCGROPYCGRERZ-UHFFFAOYSA-M methoxymethyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(COC)C1=CC=CC=C1 NOCGROPYCGRERZ-UHFFFAOYSA-M 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 description 1
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 1
- 239000012184 mineral wax Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000006011 modification reaction Methods 0.000 description 1
- 235000019426 modified starch Nutrition 0.000 description 1
- AJDUTMFFZHIJEM-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 description 1
- LTSWGLIYXJGSGL-UHFFFAOYSA-N n-bromoprop-2-enamide Chemical compound BrNC(=O)C=C LTSWGLIYXJGSGL-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000000018 nitroso group Chemical group N(=O)* 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 150000002891 organic anions Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000005429 oxyalkyl group Chemical group 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- VAUKWMSXUKODHR-UHFFFAOYSA-M pentyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCCC)C1=CC=CC=C1 VAUKWMSXUKODHR-UHFFFAOYSA-M 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- OWDYUZMGYSMCTI-UHFFFAOYSA-N phenoxy iodate Chemical compound I(=O)(=O)OOC1=CC=CC=C1 OWDYUZMGYSMCTI-UHFFFAOYSA-N 0.000 description 1
- LHDMBYWDIBGTAR-UHFFFAOYSA-N phenyl hypoiodite Chemical compound IOC1=CC=CC=C1 LHDMBYWDIBGTAR-UHFFFAOYSA-N 0.000 description 1
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical class C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000371 poly(diallyldimethylammonium chloride) polymer Polymers 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 239000011527 polyurethane coating Substances 0.000 description 1
- 229920003225 polyurethane elastomer Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- MLGWTHRHHANFCC-UHFFFAOYSA-N prop-2-en-1-amine;hydrochloride Chemical compound Cl.NCC=C MLGWTHRHHANFCC-UHFFFAOYSA-N 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
- 230000005588 protonation Effects 0.000 description 1
- BBFCIBZLAVOLCF-UHFFFAOYSA-N pyridin-1-ium;bromide Chemical compound Br.C1=CC=NC=C1 BBFCIBZLAVOLCF-UHFFFAOYSA-N 0.000 description 1
- UEXZYUUKJQPTCQ-UHFFFAOYSA-N pyridin-1-ium;bromide;hydrobromide Chemical compound Br.Br.C1=CC=NC=C1 UEXZYUUKJQPTCQ-UHFFFAOYSA-N 0.000 description 1
- OENLEHTYJXMVBG-UHFFFAOYSA-N pyridine;hydrate Chemical compound [OH-].C1=CC=[NH+]C=C1 OENLEHTYJXMVBG-UHFFFAOYSA-N 0.000 description 1
- 150000004040 pyrrolidinones Chemical class 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 230000003252 repetitive effect Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 150000004756 silanes Chemical group 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 125000005373 siloxane group Chemical group [SiH2](O*)* 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- RSKNEEODWFLVFF-UHFFFAOYSA-N sulfuric acid;2,5,6-triamino-1h-pyrimidin-4-one Chemical compound OS(O)(=O)=O.NC1=NC(=O)C(N)=C(N)N1 RSKNEEODWFLVFF-UHFFFAOYSA-N 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- MCOWGUNDBBHKAM-UHFFFAOYSA-N thiohypoiodous acid Chemical compound IS MCOWGUNDBBHKAM-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical group CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- YZGRZYVLFYYYQQ-UHFFFAOYSA-M triphenyl(pyridin-3-ylmethyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)CC1=CC=CN=C1 YZGRZYVLFYYYQQ-UHFFFAOYSA-M 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000001043 yellow dye Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B68/00—Organic pigments surface-modified by grafting, e.g. by establishing covalent or complex bonds, in order to improve the pigment properties, e.g. dispersibility or rheology
- C09B68/40—Organic pigments surface-modified by grafting, e.g. by establishing covalent or complex bonds, in order to improve the pigment properties, e.g. dispersibility or rheology characterised by the chemical nature of the attached groups
- C09B68/44—Non-ionic groups, e.g. halogen, OH or SH
- C09B68/446—Amines or polyamines, e.g. aminopropyl, 1,3,4,-triamino-pentyl or polyethylene imine
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B68/00—Organic pigments surface-modified by grafting, e.g. by establishing covalent or complex bonds, in order to improve the pigment properties, e.g. dispersibility or rheology
- C09B68/40—Organic pigments surface-modified by grafting, e.g. by establishing covalent or complex bonds, in order to improve the pigment properties, e.g. dispersibility or rheology characterised by the chemical nature of the attached groups
- C09B68/42—Ionic groups, e.g. free acid
- C09B68/423—Cationic groups
- C09B68/4235—Ammonium groups or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B69/00—Dyes not provided for by a single group of this subclass
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B69/00—Dyes not provided for by a single group of this subclass
- C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/40—Dyes ; Pigments
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06N—WALL, FLOOR, OR LIKE COVERING MATERIALS, e.g. LINOLEUM, OILCLOTH, ARTIFICIAL LEATHER, ROOFING FELT, CONSISTING OF A FIBROUS WEB COATED WITH A LAYER OF MACROMOLECULAR MATERIAL; FLEXIBLE SHEET MATERIAL NOT OTHERWISE PROVIDED FOR
- D06N3/00—Artificial leather, oilcloth or other material obtained by covering fibrous webs with macromolecular material, e.g. resins, rubber or derivatives thereof
- D06N3/0056—Artificial leather, oilcloth or other material obtained by covering fibrous webs with macromolecular material, e.g. resins, rubber or derivatives thereof characterised by the compounding ingredients of the macro-molecular coating
- D06N3/0065—Organic pigments, e.g. dyes, brighteners
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06N—WALL, FLOOR, OR LIKE COVERING MATERIALS, e.g. LINOLEUM, OILCLOTH, ARTIFICIAL LEATHER, ROOFING FELT, CONSISTING OF A FIBROUS WEB COATED WITH A LAYER OF MACROMOLECULAR MATERIAL; FLEXIBLE SHEET MATERIAL NOT OTHERWISE PROVIDED FOR
- D06N3/00—Artificial leather, oilcloth or other material obtained by covering fibrous webs with macromolecular material, e.g. resins, rubber or derivatives thereof
- D06N3/12—Artificial leather, oilcloth or other material obtained by covering fibrous webs with macromolecular material, e.g. resins, rubber or derivatives thereof with macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. gelatine proteins
- D06N3/14—Artificial leather, oilcloth or other material obtained by covering fibrous webs with macromolecular material, e.g. resins, rubber or derivatives thereof with macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. gelatine proteins with polyurethanes
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06N—WALL, FLOOR, OR LIKE COVERING MATERIALS, e.g. LINOLEUM, OILCLOTH, ARTIFICIAL LEATHER, ROOFING FELT, CONSISTING OF A FIBROUS WEB COATED WITH A LAYER OF MACROMOLECULAR MATERIAL; FLEXIBLE SHEET MATERIAL NOT OTHERWISE PROVIDED FOR
- D06N2209/00—Properties of the materials
- D06N2209/08—Properties of the materials having optical properties
- D06N2209/0807—Coloured
- D06N2209/0823—Coloured within the layer by addition of a colorant, e.g. pigments, dyes
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06N—WALL, FLOOR, OR LIKE COVERING MATERIALS, e.g. LINOLEUM, OILCLOTH, ARTIFICIAL LEATHER, ROOFING FELT, CONSISTING OF A FIBROUS WEB COATED WITH A LAYER OF MACROMOLECULAR MATERIAL; FLEXIBLE SHEET MATERIAL NOT OTHERWISE PROVIDED FOR
- D06N2211/00—Specially adapted uses
- D06N2211/12—Decorative or sun protection articles
- D06N2211/28—Artificial leather
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06N—WALL, FLOOR, OR LIKE COVERING MATERIALS, e.g. LINOLEUM, OILCLOTH, ARTIFICIAL LEATHER, ROOFING FELT, CONSISTING OF A FIBROUS WEB COATED WITH A LAYER OF MACROMOLECULAR MATERIAL; FLEXIBLE SHEET MATERIAL NOT OTHERWISE PROVIDED FOR
- D06N3/00—Artificial leather, oilcloth or other material obtained by covering fibrous webs with macromolecular material, e.g. resins, rubber or derivatives thereof
- D06N3/0002—Artificial leather, oilcloth or other material obtained by covering fibrous webs with macromolecular material, e.g. resins, rubber or derivatives thereof characterised by the substrate
- D06N3/0011—Artificial leather, oilcloth or other material obtained by covering fibrous webs with macromolecular material, e.g. resins, rubber or derivatives thereof characterised by the substrate using non-woven fabrics
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06N—WALL, FLOOR, OR LIKE COVERING MATERIALS, e.g. LINOLEUM, OILCLOTH, ARTIFICIAL LEATHER, ROOFING FELT, CONSISTING OF A FIBROUS WEB COATED WITH A LAYER OF MACROMOLECULAR MATERIAL; FLEXIBLE SHEET MATERIAL NOT OTHERWISE PROVIDED FOR
- D06N3/00—Artificial leather, oilcloth or other material obtained by covering fibrous webs with macromolecular material, e.g. resins, rubber or derivatives thereof
- D06N3/0086—Artificial leather, oilcloth or other material obtained by covering fibrous webs with macromolecular material, e.g. resins, rubber or derivatives thereof characterised by the application technique
- D06N3/0095—Artificial leather, oilcloth or other material obtained by covering fibrous webs with macromolecular material, e.g. resins, rubber or derivatives thereof characterised by the application technique by inversion technique; by transfer processes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Textile Engineering (AREA)
- Wood Science & Technology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dispersion Chemistry (AREA)
- Combustion & Propulsion (AREA)
- Mechanical Engineering (AREA)
- General Engineering & Computer Science (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Paints Or Removers (AREA)
Abstract
具有以下通用结构的有机着色剂复合物:ABn(DE)mTxQy其中A是有机发色团;B是直接或通过连接基团共价结合到A的亲电反应基团;D是共价结合B和E的亲核连接基团,其选自NR、O、S和4‑氧苯胺基(‑‑HN‑‑Ph‑‑O‑‑);其中R选自H、烷基、芳基和E;E是有机烷基和芳基基团或端基;T是共价连接到A的离子基团;Q是通过与T的离子相互作用结合到有机发色团A的有机阳离子;n、m、x和y是1–10的独立整数。
Description
相关申请的交叉引用
本申请要求于2014年4月22日提交的题为“Organic Colorant Complexes fromReactive Dyes and Article Containing the Same”的美国专利申请号61/982,368的优先权,该文件通过引用整体并入本文。
发明领域
本发明涉及有机着色剂复合物及其制备方法、包含该着色剂复合物的制剂以及由该制剂制成的制品。
发明背景
着色剂大体上分类为颜料或染料。颜料基本上不可溶于将其加入其中的介质。染料在应用过程中溶解,在过程中丢失其晶体或颗粒结构。颜料分类为有机或无机。有机颜料基于碳链和碳环。然而,它们还可包含有助于稳定有机组分性质的金属(无机)元素。无机颜料通常为从溶液沉淀的金属盐。干燥的沉淀颜料可为能立即使用的形式,但通常这些原料需要进一步机械加工、加热或化学处理以使它们更适合用作颜料。无机颜料的平均粒径比有机颜料大得多。实现最大光散射(导致不透明)所需的最佳粒径为400-800nm(波长)。无机颜料的粒径与有机颜料的粒径相比与该最佳值要近得多,后者往往要低得多。这是为何大部分有机颜料被认为是透明的而大部分无机颜料不透明的主要原因。由于其具有更大的表面积,有机颜料提供高得多的色彩强度。然而,出于类似原因,其可分散性通常较差。由于其化学组成,无机颜料在有机溶剂存在下是稳定的——这与许多较简单的有机颜料不同,后者可溶解——并且对颜料渗色和迁移具有高抗性。除了少数例外,无机颜料与有机颜料相比具有更高的热稳定性。然而,光固性和耐候性则差异更大。颜料通常具有低色调强度(tinting strength)和沉闷色泽,这会限制使用它们所生产的制品的美学质量。颜料通常缺少增溶基团,这通常会使颜料颗粒在生产过程中聚集并形成较大的次级和三级聚集颗粒。由于这些困难,用常规颜料染色的涂层通常显示保色性差,具有暗或沉闷色泽,或者包含不合适的色深变化。尽管这些问题可通过添加分散剂或通过利用颜料分散液而部分解决,这些措施经常导致生产成本上升并且依然需要非常小心的处理以使因颜料沉降和/或这些组分与树脂不相容而产生的色差最小化。在另一方面,染料通常包含能促进染料在合适介质中分散的增溶基团。染料还通常显示相对高的色调强度、良好的透明度、良好的热稳定性和可接受的树脂相容性。尽管如此,染料通常显示耐候性差、耐水性差、耐油性差,并且经常迁移或渗出到涂料的转移衬底上。
颜料和染料有广泛的用途。染料提供高透明性和明亮色泽。它们用于染色织物、涂料、油漆、印刷油墨、喷墨油墨、木材涂饰和染色、纸和纸浆、塑料、泡沫、皮革、各种流体、粘合剂、食品和化妆品、药物、药品、防冻剂、冷却剂、燃料、蜡、蜡烛、洗涤剂、皂类、清洁剂、织物柔软剂、去冰制剂、农用产品和肥料、工艺品、饮料、陶瓷、玻璃、建筑材料。颜料的透明性低于染料。主要用途包括涂料、印刷油墨、皮革和纺织品涂饰、塑料、接合剂、玻璃、化妆品、油漆。
由于在染色过程中发生的共价结合,反应性染料具有良好的固色特性。反应性染料最常用于纤维素(棉、亚麻)、羊毛和尼龙的染色。反应性染色现在是用于纤维素纤维着色的最重要方法。反应性染料带有单官能或者双官能和多官能反应性位点。反应性基团越多,染料的固色性越好,而成本越高。有方法可进一步修饰反应性染料以制备可用着色剂。US5151106教导了将反应性染料共价结合到亲水聚合物上的方法,所述亲水聚合物是由多种单体的混合物的自由基聚合制成的接触镜片。US 20120225803公开了含有由反应性染料和聚乙烯亚胺制成的聚合调色染料(shading dyes)的衣物洗涤剂。WO 2012130492公开了包含染料聚合物的衣物处理组合物,在该染料聚合物中聚乙烯醇聚合物被拴系到反应性染料上。WO 2012098046公开了由羟烷基纤维素和反应性染料制成的聚合调色染料。US4070296公开了由与反应性染料共价结合的氨化聚合物制成的碳粉颗粒。WO2012126987公开了包括肽染料的染料组合物,所述肽染料包括与带负电的反应性染料共价结合的肽;其中所述肽染料可通过使包含伯胺、仲胺、OH、SH基团或混合物的肽与带负电的反应性染料反应来制备。US5766268公开了由具有亲电反应性基团的反应性染料与具有亲核反应性基团的含聚(氧化烯)的部分的反应制成的着色剂。US6287348公开了包含有机发色团的着色剂,特别是反应性染料,其包括亲电反应性基团,并且其还通过氨基连接基团共价连接到脂肪胺部分。US5789515公开了由反应性染料AB与XYZ(聚(氧化烯)-聚硅氧烷共聚物)的反应制成的着色剂组合物。US5773405公开了由具有亲电反应性基团的反应性染料与具有亲核反应性基团的含聚(氧化烯)部分的反应制成的着色剂的清洁剂组合物。WO2009030344公开了由反应性染料与聚醚多元醇制成的反应性染料。US5770557公开了包括由具有亲电反应性基团的反应性染料与具有亲核反应性基团的含聚(氧化烯)部分的反应制成的着色剂的液体织物柔软剂组合物。US5725794公开了包含由反应性染料制成的聚(氧化烯)-取代的着色剂的防冻剂组合物。
US5948152公开了阴离子有机染料与季铵化合物的液体复合物,其是均相的,因此基本不含不需要的无机盐。
US5938828公开了阴离子有机染料与季铵化合物的固体复合物,其平均分子量低于约900,其基本不含不需要的盐。
US5948153公开了荧光增白剂与季铵化合物的水溶性复合物,其基本不含不需要的盐。
US6046330公开了紫外吸收剂与季铵化合物的复合物,其基本不含不需要的盐。
US8273166公开了包含由阴离子染料与N-烷基或N-芳基季铵阳离子制成的着色剂的相变油墨组合物。
US6248161公开了包含阴离子染料和至少一种耐水鏻盐的耐水染料基水性喷墨油墨。
无论是由反应性染料与亲核试剂制成的着色剂还是阴离子染料与季铵化合物制成的着色剂都不能被调节为具有所有理想特性。需要这样的着色剂:其可以多种方式调整为具有不同特性,其具有染料的明亮色泽以及高透明性和颜料的不迁移性和良好光固性。本发明提供了这样的着色剂、其制备方法和包含这样的着色剂的制品。
发明内容
本发明涉及具有以下通用结构的有机着色剂复合物:
ABn(DE)mTxQy
其中A是有机发色团;B是直接或通过连接基团与A共价结合的亲电反应性基团;D是共价结合B和E的亲核连接基团,选自NR、O、S和4-氧苯胺基(--HN--Ph--O--);其中R选自H、烷基、芳基;E是有机端基;T是与A共价结合的离子基团,其为阴离子或阳离子的,优选阴离子基团;Q是通过与T的离子相互作用结合到有机发色团的抗衡离子;n、m、x和y是1–10的独立整数。
本发明的有机着色剂复合物可通过以下通用方法制备:(a)使具有ABnTxMx(在这里,A、B和T如上所定义;M是金属抗衡阳离子)结构的反应性染料与如上所定义的亲核有机化合物DE在碱性条件下反应。(b)将得自步骤(a)的阴离子染料ABn(DE)mTxMx与有机阳离子化合物Q+Z-(在这里Q是阳离子,且Z是阴离子)反应形成本发明的有机着色剂复合物ABn(DE)mTxQy。(c)将着色剂复合物纯化,去除无机盐。所得着色剂复合物在环境条件下可为液体、糊状物或固体。它们可为高度水溶性的或完全不溶于水的,这取决于用于制备这种复合物的亲核和阳离子化合物。它们可为聚合物或非聚合物。它们可为疏水或亲水或介于二者之间的。
本发明着色剂复合物可用于需要高色彩浓度而不会形成不理想的沉淀物的用途中。所述着色剂可具有低染色因子(staining factor),从而减少或消除了在大部分硬表面、皮肤、织物和设备上的染色。这样的着色剂通常可用冷水清理去除。本发明的着色剂尤其适用于需要低染色因子的非油墨用途。例如,这样的用途包括用于清洁剂的染料,其中要求染料不会使所清洁的物品着色。本发明的着色剂可在很宽的pH范围上使用,并且与香料和防腐剂相容而不会与所得混合物复合或使所得混合物去稳定。它们还与大部分阳离子、阴离子、非离子和四元体系(quaternary system)相容。由于这些着色剂形成真溶液而非乳液或分散液,所得制剂在外观上是澄清明亮的。所述着色剂可被加入到涂料制剂中,因为其具有良好的相容性、明亮的色泽和良好的不迁移特性。所述着色剂可用于染色烃类、热塑性塑料、热固性塑料和蜡,以及用于喷墨和印刷油墨制剂中,染色水性组合物,有机制剂。
具体实施方式
本文所用的术语“聚合着色剂”是指在分子结构中有至少两个重复单元,且分子的分子量为至少300。
本发明涉及具有以下通用结构(I)的有机着色剂复合物:
(I) ABn(DE)mTxQy
其中A是有机发色团;B是直接或通过连接基团与A共价结合的亲电反应性基团;D是共价结合B和E的亲核连接基团,选自NR、O、S和4-氧苯胺基(--HN--Ph--O--);其中R选自H、烷基和芳基;E是有机部分或端基;T是与A共价结合的离子基团,其是阴离子或阳离子的,优选阴离子基团;Q是通过与T的离子相互作用结合到有机发色团的抗衡离子;n、m、x和y是1-10的独立整数,它们可相同或不同。
本发明包括由式(II)所定义的反应性染料制成的着色剂化合物:
(II) ABnTxMx
其中A是有机发色团,B是直接或通过连接基团与A共价结合的亲电反应性基团,T是与A共价结合的阴离子基团,M是阳离子金属离子,n和x是1–10的整数。
基团A是发色团,包括偶氮,诸如单偶氮、二偶氮和多偶氮,包括其与Cr、Fe、Co和Cu的复合物;酞菁、蒽醌、氮杂[18]轮烯、甲瓒铜复合物、三苯二噁嗪、亚硝基、硝基、二芳基甲烷、三芳基甲烷、呫吨、acridene(acridine,吖啶)、次甲基、噻唑、吲哒胺、吖嗪、噁嗪、噻嗪、喹啉、靛蓝类、靛酚、内酯、氨基酮、羟基酮和茋类发色团。优选地,反应性染料包含偶氮、酞菁或蒽醌发色团基团。反应性染料部分AB包含有机发色团A和至少一个亲电官能团B。当提供多个官能团时,通常希望基团活性有所不同以使转化率最大化。可被包含在反应性染料中的亲电官能团BL的实例包括:单卤代三嗪;二卤代三嗪;单卤代嘧啶;二卤代嘧啶;三卤代嘧啶;二卤代喹喔啉;二卤代哒嗪酮;二卤代酞嗪;卤代苯并噻唑;单-(间-羧基吡啶鎓)-三嗪;氨基环氧化物;甲基氨基;硫酸乙基砜;硫酸乙基磺酰胺;氯乙基砜;乙烯砜;苯氨基砜;丙烯酰胺;α-卤代丙烯酰酰胺;α,β-二卤代丙酰胺;卤代磺酰嘧啶;硫酸乙基氨基砜;硫酸丙酰胺;卤代磺基噻嗪酰胺和卤代乙酰胺。所述卤代组分可选自氟、氯和溴。优选地,反应性染料包含选自以下的亲电官能团:单氯代三嗪、单氟三嗪、二氯三嗪、硫酸乙基砜、乙烯砜、2,3-二氯喹喔啉和2,4-二氟-5-氯嘧啶基团。当在反应性染料中存在多于一个亲电反应性基团时,两个或多个反应性基团可彼此不同。
符合以上描述的反应性染料可通过商业渠道获得,在颜料索引第三版(theSociety of Dyers and Colourists,1971)中及可用公开文件中描述。通过举例的方式,并且没有限制地,可使用以下反应性染料:C.I.反应黑5,C.I.反应蓝2,C.I.反应蓝4,C.I.反应蓝5,C.I.反应蓝7,C.I.反应蓝15,C.I.反应蓝19,C.I.反应蓝27,C.I.反应紫3,C.I.反应紫5,C.I.反应红2,C.I.反应红24,C.I.反应橙4,C.I.反应橙13,C.I.反应橙16,C.I.反应橙78,C.I.反应黄3,C.I.反应黄13,C.I.反应黄14,C.I.反应黄17和C.I.反应黄95。
反应性染料还在Industrial Dyes(K.Hunger编,Wiley VCH 2003)中描述。许多反应性染料在颜色索引(Society of Dyers and Colourists and American Associationof Textile Chemists and Colorists)中描述。反应性基团优选选自杂环反应性基团和/或磺氧基乙基磺酰基反应性基团(-SO2CH2CH2OSO3Na)。
磺氧基乙基磺酰基反应性基团在碱中转化为乙烯砜。杂环反应性基团优选为与卤素或铵基团或季铵基团结合的含氮芳环,其与肽的NH2或NH基团反应形成共价键。优选卤素,最优选Cl或F。优选反应性染料包含多于一个反应性基团,优选两个或三个。
优选地,反应性染料包括选自以下的反应性基团:二氯三嗪基、二氟氯嘧啶、单氟三嗪基、二氯喹喔啉、乙烯基砜、二氟三嗪、单氯代三嗪基、溴代丙烯酰胺和三氯嘧啶。除了铜酞菁类染料例外之外,所述染料不包括金属复合物染料,优选所述染料不包含偶氮基金属复合物染料。反应性基团可经由烷基间隔子连接到染料发色团,例如:染料-NH-CH2CH2-反应性基团。尤其优选的杂环反应性基团是
其中R1选自H或烷基,优选H;
X选自F或Cl;
当X=Cl时,Z1选自-Cl、-NR2R3、-OR2、-SO3Na;
当X=F时,Z选自-NR2R3;
R2和R3独立选自H、烷基和芳基基团。芳基基团优选为苯基,并且优选被-SO3Na或-SO2CH2CH2OSO3Na取代。烷基基团优选为甲基或乙基。
苯基基团可被合适的无电荷有机基团(优选分子量低于200)进一步取代。优选的基团包括-CH3、-C2H5和-OCH3。烷基基团可被合适的无电荷基团(优选分子量低于200)进一步取代。优选的基团包括-CH3、-C2H5、-OH、-OCH3、-OC2H4OH。最优选的杂环反应性基团选自
其中R1和R2选自H或烷基,优选H;
其中n=1或2,优选1。
优选反应性染料包含多于一个反应性基团,优选两个、三个或四个。优选地,反应性染料包括选自以下的发色团:偶氮、蒽醌、酞菁、甲瓒和三苯二噁嗪。当所述染料是偶氮染料时,优选该偶氮染料不是偶氮-金属复合物染料。
反应性染料的实例包括反应黑5、反应蓝19、反应红2、反应蓝171、反应蓝269、反应蓝11、反应黄17、反应橙4、反应橙16、反应绿19、反应棕2和反应棕50。
反应蓝染料优选选自蒽醌、单偶氮、二-偶氮、三苯二噁嗪和酞菁,更优选蒽醌、二-偶氮和三苯二噁嗪,最优选二-偶氮和三苯二噁嗪。
优选的蓝色二-偶氮染料具有以下形式:
其中A和B环中的一个或两个被反应性基团取代。A和B环可被磺酸盐基团(SO3Na)进一步取代。A和B环可被合适的无电荷有机基团(优选分子量低于200)进一步取代。优选的无电荷有机基团是-CH3、-C2H5和-OCH3。
优选的蓝色蒽醌染料具有以下形式:
其中C环被反应性基团取代。所述染料可被磺酸盐基团(SO3Na)和合适的无电荷有机基团(优选分子量低于200)进一步。优选的无电荷有机基团是-CH3、-C2H5和-OCH3。
优选的蓝色三苯二噁嗪染料具有以下形式:
其中D和E环被反应性基团取代。优选地,D和E环被磺酸盐基团(SO3Na)进一步取代。
反应蓝染料的例子是反应蓝2、反应蓝4、反应蓝5、反应蓝7、反应蓝15、反应蓝19、反应蓝27、反应蓝29、反应蓝49、反应蓝50、反应蓝74、反应蓝94、反应蓝246、反应蓝247、反应蓝247、反应蓝166、反应蓝109、反应蓝187、反应蓝213、反应蓝225、反应蓝238和反应蓝256。其它结构如下示例:
反应红染料优选选自单-偶氮和二-偶氮染料。优选的反应红偶氮染料具有以下形式:
其中F环任选被扩大形成萘基基团,并且任选被选自磺酸盐基团(SO3Na)和反应性基团的基团取代。G选自反应性基团、H或烷基基团。反应性基团必须存在于染料上。反应红染料的例子是反应红2、反应红3、反应红4、反应红8、反应红9、反应红12、反应红13、反应红17、反应红22反应红24、反应红29、反应红33、反应红120、反应红139、反应红198和反应红141。其它结构如下示例:
反应黄和橙染料优选选自单-偶氮染料。反应黄和橙染料的例子是反应黄1、反应黄2、反应黄3、反应黄16、反应黄17、反应黄25、反应黄39、反应橙107、反应黄176和反应黄135。其它结构如下示例:
可使用反应性染料的组合,以利用有限数量的染料得到广泛调色。优选地,可使用由三种反应性染料的混合物组成的三色体系。优选地,所述三色体系包含反应蓝或反应黑染料、反应红和反应黄染料的组合。例如,组合可包括反应黑5、反应黄176和反应红239;或者组合可包括反应蓝176、反应黄176和反应红141。
具有代表性化学式DE的亲核有机化合物(在这里,D是具有用于亲核反应的孤对电子对的原子,E是与D共价连接的有机部分)能与如式(II)所定义的反应性染料反应形成具有通式(III)的阴离子着色剂:
(III) ABn(DE)mTxMx
亲核试剂通过D共价连接到反应性染料AB的亲电基团B,其中所述D为选自NR、O、S和4-氧苯胺基(--HN--Ph--O--)的亲核连接基团;在这里R选自H、烷基和芳基;E是亲核试剂的有机部分或端基,其可为聚合物或低聚物。T共价连接到A的阴离子基团,M是阳离子金属离子;n、m和X是1–10的整数。
合适的亲核化合物可为任何伯胺或仲胺、任何烷基胺或芳族胺、取代胺、一元胺或多元胺、具有其它可相容官能团的胺、酰胺、含羟基化合物或硫化合物。
可由其制备本发明的着色剂组合物的亲核化合物的合适例子包括聚氧化烯胺(polyoxyalkylene amines),其可商购自JEFFAMINE Huntsman化学产品系列,并且在Texaco Chemical Company,New Product Development brochures中描述为M、D、ED、DU、BuD、T、MNPA和EDR系列。这些聚氧化烯胺包含连接到聚醚主链末端的伯氨基基团,所述聚醚主链可基于环氧丙烷(PO)、环氧乙烷(EO)或EO/PO混合物。JEFFAMINE产品由以下组成:单胺、二胺和三胺,它们可以范围在230–6000内的多种分子量获得。JEFFAMINE化合物以字母和数字命名,后者代表大致分子量。JEFFAMINE(单胺)、D-系列(胺-封端的聚丙二醇)、ED-系列(主要基于赋予水溶性的聚环氧乙烷主链的聚醚二胺)、DU-系列(D-系列产品的脲缩合物,提供具有更高分子量的胺封端的二胺产品)、BuD-系列(D-系列产品的脲缩合物,提供脲封端的产品)和T-系列(通过使PO与三元醇引发剂反应然后将末端羟基基团胺化制成的环氧丙烷基三胺)。这些胺在授予Kluger等的美国专利5,270,363中第7–12栏中描述。
本发明中所用的着色剂的溶解性可因以下而不同:聚(氧化烯)取代基和端基的相对亲水/亲油特性,以及在有机发色团上存在离子基团与否。
制备聚(氧乙烯)-取代的着色剂的一般反应条件:
在一个方面,将一当量的反应性染料与约5-10mol%过量的亲核聚合物、一当量碳酸钠(或其它合适的除酸剂)和足够的水混合以提供混合物。随后将反应混合物加热至80℃,随后使所得溶液相分离。随后使浓缩的聚合着色剂相达到中性pH,并根据需要用水进一步稀释。
可使用许多聚合胺或胺混合物与反应性染料反应,形成用于将多种合成制品着色的聚合着色剂。希望所述胺是伯胺。还希望所述胺由聚氧化烯结构单元组成。优选地,所述聚氧化烯为聚环氧乙烷,其通常提供了良好的水溶性和/或水混溶性。有很多可商购的聚合胺可用于本发明。例如,可使用诸如得自Huntsman的胺的聚氧化烯胺,其包括单胺如M-600、M-100、M-2005和M-2070;二胺如EDR-148、D-230、D-400、D-2000、XTJ-502、XTJ-511和XTJ-512;三胺如T-403和T-5000。具有羟基基团的胺的例子包括二乙二醇胺、氨基丙基二乙二醇(其可得自Dixie Chemical Company,商品名为DCA 163)和二(羟烷基)二胺如得自Tomah的APDEA和APDIPA。得自Tomah的二醇醚伯胺的另一个系列包括PA-EGM、PA-EGB、PA-EGH、PA-DEGM、PA-DEGB、PA-PGM、PA-PGB、PA-DPGM和PA-DPGB。得自Tomah的二伯胺的另一个系列包括DPA-DEG、DPA-200E、DPA-400E、DPA-1000E和NDPA-10。
亲核化合物的另一个例子是为DYZ的含聚(氧化烯)化合物,在这里D是连接基团,Y是聚(氧化烯)链,Z是有机端基。两个含聚(氧化烯)的取代基可通过包含三价原子(例如N)的连接基团结合到反应性染料AB。每个发色团的聚(氧化烯)链的数量可为1-6,优选1-4,最优选1、2或3。
含聚(氧化烯)的取代基Y
Y可为含聚(氧化烯)的部分,其具有式(CaH2aO)m(CbH2bO)n,在这里a和b不同,并且为1–8,优选1-4,例如,a是2,b是3,m是至少3,优选至少11,例如,在希望所得着色剂组合物具有较低染色因子的情况中;n是0–15(含0和15)的整数,例如,0或1。Y部分的分子量可低于4000,并且可在130–4000范围内,优选480-4000。这样的Y取代基的典型例子是聚(氧化烯)聚合物和共聚物。在这方面,可用于提供本发明的着色剂的聚氧化烯及其共聚物是,但不限于,聚环氧乙烷,聚环氧丙烷,聚环氧丁烷,聚环氧乙烷、聚环氧丙烷和聚环氧丁烷的共聚物,以及其它共聚物,包括其中大部分聚合取代基为聚环氧乙烷、聚环氧丙烷和/或聚环氧丁烷的嵌段共聚物。尽管这样的取代基的平均分子量通常在130–4000范围内,例如130–1400,但它们不限于此。
在本发明的特定实施方式中,Y可被描述为聚硅氧烷-聚(氧化烯)共聚物,其包括:
(a)表征为--Si(R1)(R2)O--重复基团的聚硅氧烷链段,其中R1和R2各自选自烷基、苯基、乙烯基、3,3,3-三氟丙基和氢(优选R1和R2是烷基,尤其优选甲基);和
(b)表征为聚(氧化烯)基团的聚醚链段,其可i)位于共聚物主链中,或ii)为硅氧烷或硅烷重复基团上的侧基。
沿聚硅氧烷主链具有聚(氧化烯)侧基的Y共聚物可通过将带有反应性官能团的硅氧烷基团加入聚合物主链中来合成。硅氧烷基团可被烷氧基化、酯化或以其它方式配有聚(氧化烯)官能度。具有聚硅氧烷主链和聚氧化烯侧基的共聚物可通过商业途径获得,MasilSilicone Surfactants产品系列,可得自PPG Industries,Inc.,Gurnee,Ill.,USA。聚硅氧烷-聚醚共聚物在以下专利中公开:Azechi等,美国专利号5,271,868;Kasprzak等,美国专利号5,300,667;和Fleuren等,美国专利号5,376,301。合成聚硅氧烷-聚醚共聚物的另一种方法被Jainlong Ni等公开,"Synthesis of a Novel Polysiloxane-based PolymersElectrolyte and its Ionic Conductivity",Polymers for Advanced TechnologiesVol.4,pp 80-84(1993)。将烯丙基聚醚接枝到聚硅氧烷上形成共聚物。Sela等,"NewlyDesigned Polysiloxane-graft-poly(oxyethylene)Copolymeric Surfactants,"ColloidPolymSci 272:684-691(1994)公开了基于用乙烯基封端的聚(氧乙烯)基团硅烷化的聚(甲基氢硅氧烷)/聚(二甲基硅氧烷)嵌段共聚物主链的梳型接枝的表面活性剂。
或者可选地,聚硅氧烷-聚(氧化烯)共聚物是引入了聚(氧化烯)取代硅烷的嵌段共聚物,例如,包含硅烷、具有--Si(R3-聚(氧化烯))(R4)--结构的基团的共聚物,其中R3是亚烷基基团,优选亚甲基或亚乙基,R4是H、烷基或苯基,优选甲基。这样的共聚物可通过商业途径获得,例如,如可得自Petrarch Systems,Silanes and Silicones Group,Bristol,Pa.,USA的二甲基硅氧烷-氧化烯共聚物。
在主链中具有聚(氧化烯)链段的嵌段共聚物可通过本领域公知的程序合成,并且可商购自Dow Corning,Midland,Mich.,USA,名为5103Fluid和Q2-5211湿润剂产品系列。
Y还可描述为选自以下的含聚(氧化烯)的聚硅氧烷部分:(OSi(R')(R"))i O(SiR'R'"O(CaH2aO)m(CbH2bO)n)j和(OSi(R')(R"))i(R'"O(CaH2aO)m(CbH2bO)n)j,在这里R'和R"各自是烷基,优选C1-C4烷基,更优选甲基,R'"是亚烷基,优选C1-C3亚烷基,更优选亚乙基,i和j是如下选择的整数:其为Y提供300–10000、优选450–5000、更优选800–1400的分子量,i是至少3,j是至少1,a和b不同并且为1-8,优选1-4,更优选2–3,m是至少3,优选5–15,n是0-15,优选0。
含聚(氧化烯)的取代基Y的分子量可在300–10000范围内,优选450-5000,更优选800–1400。
对本发明中可用的聚硅氧烷聚(氧化烯)共聚物的进一步描述可见Encyclopediaof Polymer Science and Engineering,John Wiley&Sons,Vol.15,page 234-244(1989)及其中引用的参考文件。
端基Z
含聚(氧化烯)的取代基Y的端基Z可为任何合适的末端基团,例如,其为选自以下的一种:羟基,烷基例如C1-C4烷基,氨基,酰胺基,烷基酯,例如,当Y具有亲核端基时(诸如当聚硅氧烷-聚(氧化烯)共聚物是二胺时),乙酰基、苯酯、烷基醚、烷基缩醛和BA。端基本身可有助于着色剂产品的溶解度特性。其它合适的末端基团的例子如授予Kluger等的美国专利号5,270,363中所公开的用于聚(氧化烯)聚合物的那些。当Z是XBA时,所得着色剂具有ABXYXBA结构,其中X、B和A如上所述。
阳离子基团可包括氨基、铵、亚氨基、锍或鏻基团。
包括季铵盐、吡啶鎓盐、哌啶鎓盐等的多种季铵化合物已显示可用于实施本发明。本发明中可能有用的季铵化合物的广泛列表包括三烷基、二烷基、二烷氧烷基、单烷氧基、苄基和咪唑啉鎓季铵化合物。多种类型的季铵化合物可成功地适用于本文所述发明。季铵化合物是其中原始铵阳离子的所有四个氢被有机基团取代的铵盐类似物。取代基可为烷基、芳基、芳烷基或烷氧基化物,或者氮可为环体系的一部分。通过举例方式并且没有限制地,季铵化合物的优选类别和实例名单在下表1中示出:
表1
其它氮基阳离子化合物包括4-(二甲基氨基)吡啶鎓三溴化物、月桂基乙基二甲基溴化铵、1-月桂基吡啶鎓盐酸盐水合物、月桂基三甲基溴化铵、1-乙基-3-甲基-1H-咪唑鎓氯化物、1-甲基-4-(甲氧基羰基)吡啶鎓碘化物、6-羟基-2,4,5-三氨基嘧啶硫酸盐、2-羟基-4-甲基嘧啶盐酸盐、硬脂酰基三甲基氯化铵、对-二甲苯-二(四氢噻吩鎓氯化物)、三甲基碘化锍、联苯氯化碘鎓、六氟磷酸二茂铁、月桂基二甲基(3-磺丙基)氢氧化铵、1-(N,N-二甲基氨基甲酰基)-4(2-磺基-乙基)吡啶鎓氢氧化物和2-甲基-5-苯基异噁唑-3′-磺酸盐、阳离子季铵氟烷基表面活性剂,诸如FLUORAD FC-135表面活性剂(3M Co.of St.Paul,Minn.生产)、SURFLON S-121表面活性剂(Seimi Chemical Co.,Japan生产)或NeosFTERGENT 300表面活性剂(Neos,Japan生产)。
其它常规阳离子物种包括碳鎓盐、碘鎓盐、锍盐、吡喃鎓盐(pyrrilium salts)、鏻盐等也可用于本发明。这些阳离子化合物中的一些能提高着色剂复合物的耐水性。鏻盐选自烯丙基三苯基溴化鏻、烯丙基三苯基氯化鏻、乙烯基三苯基溴化鏻、(3-溴丁基)三苯基溴化鏻、(4-溴丁基)三苯基溴化鏻、(一溴二氟甲基)三苯基溴化鏻、氯乙烯三苯基溴化鏻、1,1,1-三氟丙酮基三苯基溴化鏻、甲基三苯基溴化鏻、乙基三苯基溴化鏻、丙基三苯基溴化鏻、正-丁基三苯基溴化鏻、异丙基三苯基溴化鏻、正-戊基三苯基溴化鏻、丙酮基三苯基溴化鏻、4-羧基丁基三苯基溴化鏻、(乙氧羰基甲基)三苯基溴化鏻、(甲氧甲基)三苯基溴化鏻、三苯基氢溴化鏻、(2-羟乙基)三苯基氯化鏻、(2-羟乙基)三苯基溴化鏻、[3-羟基-2-甲基丙基]三苯基溴化鏻、[2-(三甲基甲硅烷基)乙氧基甲基]三苯基氯化鏻、甲基三苯氧基碘化鏻、[3-(二甲基氨基)丙基]三苯基溴化鏻和二甲基氨基乙基三苯基溴化鏻。其它鏻盐:选自以下的鏻盐:(乙氧羰基甲基)三苯基溴化鏻、(乙氧羰基甲基)三苯基氯化鏻、(甲氧基甲基)三苯基溴化鏻、三苯基氢溴化鏻、(2-羟乙基)三苯基氯化鏻、(2-羟乙基)三苯基溴化鏻、[3-羟基-2-甲基丙基]三苯基溴化鏻、[2-(三甲基甲硅烷基)乙氧基甲基]三苯基氯化鏻、甲基三苯氧基碘化鏻、[3-(二甲基氨基)丙基]三苯基溴化鏻、丙酮基三苯基溴化鏻、四(羟甲基)氯化鏻、2-乙酰萘基三苯基溴化鏻、2′,5′-二甲氧基苯甲酰甲基三苯基溴化鏻、1-羟基月桂基三苯基溴化鏻、2-乙基二氢吲哚基三苯基溴化鏻、3′-甲氧基苯甲酰甲基三苯基溴化鏻、3-甲基吡啶基三苯基溴化鏻、苯甲酰甲基二甲基氨基苯基联苯氯化鏻、甲基(二甲基氨基苯基联苯)溴化鏻、[3-(乙氧羰基)-2-氧丙基]三苯基氯化鏻、(2-羟基苄基)三苯基溴化鏻、苯并三唑-1-基氧基三吡咯烷基-六氟磷酸鏻、三苯基(2-吡啶甲基)氯化鏻盐酸盐、(4-乙氧基苄基)三苯基溴化鏻、(3-苄氧基丙基)三苯基溴化鏻、苯甲酰甲基三苯基氯化鏻、苯并三唑-1-基氧基三(二甲基氨基)六氟磷酸鏻和2-乙酰萘基三苯基溴化鏻。
阳离子化合物可选自合适的离子液体,包括有机阳离子和无机或有机阴离子。例子是N-甲基-N'-甲基咪唑鎓(EMIM)、N-甲基咪唑鎓(MEHIM)、N-丁基-N'-甲基咪唑鎓(BMIM)、N-乙基-N'-乙基咪唑鎓(EEIM)、N-正-丙基-N'-正-丙基咪唑鎓(PPIM)和得自BASF的其它BasionicsTM离子液体产品。
阳离子聚合物选自聚(乙烯基苄基三甲基氯化铵)、聚(4-乙烯吡啶盐酸盐)、80%乙氧基化的聚乙烯亚胺、聚苯胺和磺化聚(二烯丙基二甲基氯化铵)。
无论用于制备其的单体的数量、类型或浓度如何,阳离子聚合物适合用于本发明的目的。阳离子聚合物可为液体形式或干燥为粉末。这样的聚合物的例子是Degussa以商品名Praestaret K-325和Praestaret K-350以及Praestol E-125和Praestor E-150出售的那些。
阳离子聚合物通常包括阳离子含氮部分,诸如季铵或阳离子氨基部分或其混合物。任何阴离子抗衡离子可用于阳离子聚合物,只要符合水溶性标准。合适的抗衡离子包括卤离子(例如,Cl、Br、I或F,优选Cl、Br或I)、硫酸根和甲基硫酸根。也可使用其它物质,因为该列表不是排他性的。
阳离子含氮部分通常将作为取代基存在于全部单体单元中的一部分上。因此,阳离子聚合物可包括季铵或阳离子胺-取代的单体单元和本文称为间隔单体单元的其它非-阳离子单元的共聚物、三元共聚物等。
合适的阳离子聚合物包括,例如,具有阳离子胺或季铵官能度的乙烯基单体与诸如以下的水溶性间隔单体的共聚物:丙烯酰胺、甲基丙烯酰胺、烷基和二烷基丙烯酰胺、烷基和二烷基甲基丙烯酰胺、丙烯酸烷基酯、甲基丙烯酸烷基酯、乙烯基己内酯和乙烯基吡咯烷酮。烷基和二烷基取代的单体优选具有C1-C7烷基基团,更优选C1-C3烷基基团。其它合适的间隔单体包括乙烯酯、乙烯醇(通过聚醋酸乙烯酯的水解制成)、马来酸酐、丙二醇和乙二醇。
阳离子胺可为伯胺、仲胺或叔胺。通常,优选仲胺和叔胺,尤其是叔胺。
胺-取代的乙烯基单体可以胺形式聚合,随后可任选通过季铵化反应转化为铵。类似地,胺还可在形成聚合物之后进行季铵化。例如,叔胺官能度可通过与式R'X的盐反应而季铵化,其中R'是短链烷基,优选C1-C7烷基,更优选C1-C3烷基,X是与季铵形成水溶性盐的阴离子。
合适的阳离子氨基和季铵单体包括,例如,被以下取代的乙烯基化合物:二烷基氨基烷基丙烯酸酯、二烷基氨基烷基甲基丙烯酸酯、单烷基氨基烷基丙烯酸酯、单烷基氨基烷基甲基丙烯酸酯、三烷基甲基丙烯酰氧基烷基铵盐、三烷基丙烯酰氧基烷基铵盐、二烯丙基季铵盐和具有环状阳离子含氮环(诸如吡啶鎓、咪唑鎓和季铵化吡咯烷酮)的乙烯基季铵单体,例如,烷基乙烯基咪唑鎓、烷基乙烯基吡啶鎓、烷基乙烯基吡咯烷酮盐。这些单体的烷基部分优选为低级烷基,诸如C1-C3烷基,更优选C1和C2烷基。
适合用于这里的胺-取代的乙烯基单体包括二烷基氨基烷基丙烯酸酯、二烷基氨基烷基甲基丙烯酸酯、二烷基氨基烷基丙烯酰胺和二烷基氨基烷基甲基丙烯酰胺,其中烷基基团优选为C1-C7烃基,更优选C1-C3烷基。
本文的阳离子聚合物可包括源自胺-和/或季铵-取代的单体的单体单元和/或相容性间隔单体的混合物。
合适的阳离子聚合物包括,例如:1-乙烯基-2-吡咯烷酮和1-乙烯基-3-甲基-咪唑鎓盐(例如,氯化物盐)的共聚物(在工业中被the Cosmetic,Toiletry and FragranceAssociation,"CTFA"称为Polyquaternium-16),诸如可商购自BASF Wyandotte Corp.(Parsippany,NJ,USA)的LUVIQUAT(RTM)商品名的那些(例如,LUVIQUAT FC 370(RTM));1-乙烯基-2-吡咯烷酮和二甲基氨基乙基甲基丙烯酸酯的共聚物(在工业中被CTFA称为Polyquaternium-11),诸如可商购自Gaf Corporation(Wayne,NJ,USA)的GAFQUAT商品名的那些(例如,GAFQUAT 755N(RTM));含二烯丙基季铵的阳离子聚合物,包括,例如,二甲基二烯丙基氯化铵均聚物和丙烯酰胺与二甲基二烯丙基氯化铵的共聚物,在工业中(CTFA)分别被称为Polyquaternium 6和Polyquaternium 7;以及具有3–5个碳原子的不饱和羧酸的均聚物和共聚物的氨基-烷基酯的无机酸盐,如US-A-4,009,256中所述。
可使用的其它阳离子聚合物包括多糖聚合物,诸如阳离子纤维素衍生物和阳离子淀粉衍生物。适合用于这里的阳离子多糖聚合物材料包括下式的那些:
其中:
P是脱水葡萄糖残基,诸如淀粉或纤维素脱水葡萄糖残基,
R是亚烷基氧化烯、聚氧化烯或羟基亚烷基基团或其组合,
R1、R2和R3独立为烷基、芳基、烷基芳基、芳基烷基、烷氧基烷基或烷氧基芳基,每个基团包含至多约18个碳原子,每个阳离子部分的碳原子总数(即,R1、R2和R3中的碳原子之和)优选为约20或以下,且X是阴离子抗衡离子。
阳离子纤维素可得自Amerchol Corp.(Edison,NJ,USA),为其聚合物和聚合物系列聚合物,其是羟乙基纤维素与三甲基铵取代的环氧化物反应所得的盐,在工业中(CTFA)被称为Polyquaternium 10。另一种类型的阳离子纤维素包括羟乙基纤维素与月桂基二甲基铵-取代的环氧化物反应得到的聚合季铵盐,在工业中(CTFA)称为Polyquaternium 24。这些材料可得自Amerchol Corp.(Edison,NJ,USA),商品名为PolymerLM-200。
可使用的其它阳离子聚合物包括阳离子瓜尔胶衍生物,诸如瓜尔胶羟丙基三甲基氯化铵(可商购自Celanese Corp.,其系列)。其它材料包括含四价氮纤维素醚(例如,如US-A-3,962,418中所述的,其通过引用并入本文)以及醚化纤维素与淀粉的共聚物(例如,如US-A-3,958,581中所述的)。
多官能阳离子盐可用于这里,并且选自海美溴铵(hexadimethrine bromide)、对-二甲苯-二(四氢噻吩鎓氯化物)、1,1′-三亚甲基二[4-(羟基亚氨基-甲基)吡啶鎓溴化物]、1,1′-二庚基-4,4′-二吡啶鎓二溴化物、1,1′-双十八烷基-4,4′-二吡啶鎓二高氯酸盐、乙基紫精二溴化物、1,1′-双十八烷基-4,4′-二吡啶鎓溴化物和六氟磷酸二茂铁。
本发明的着色剂复合物可通过以下方法而容易地制得:
方法1:首先,通过将亲核试剂和染料的水性或有机组合物加热至至少30℃、优选至少60℃的温度而将反应性染料AB与亲核试剂共价结合。通常,升高温度将会加快反应速度。例如,在85℃,反应通常在2小时内完成。保持反应组合物的pH以避免如果存在于反应混合物中的胺的质子化。通常使用摩尔过量的亲核试剂以确保完全转化和使未反应和未取代的反应性染料(其能导致不理想的性质)的存在最小化。除酸剂诸如碳酸钠优选存在于反应混合物,例如,约等量。其次,将由步骤1形成的阴离子着色剂进一步与阳离子化合物反应,形成所需的着色剂复合物。第三,将着色剂复合物通过萃取或洗涤进一步纯化以去除不需要的无机盐,由此使最终产物基本不含盐。
方法2:将所有原材料,包括反应性染料、亲核化合物、阳离子化合物和合适的溶剂和碱在反应器中在一步中共同加热,直到形成所需的着色剂复合物且反应完成。粗产物进一步纯化以去除不需要的盐。
实施本发明的基本途径是首先确定所需的反应性染料对于要被染色的受试基底的色泽、光固性、热稳定性等;其次,选择能共价连接于反应性染料上的合适的亲核试剂;第三,将两种化合物共同反应形成阴离子着色剂;第四,根据所必需的物理特性诸如迁移、均匀分散、溶解度、耐洗牢固度等选择适合于受试基底的阳离子化合物;第五,将来自步骤3的阴离子着色剂与阳离子化合物共同反应形成着色剂复合物;和最后,去除反应中形成的不需要的盐。
本发明的有机着色剂复合物可用于多种产品用途。例如,着色剂可用于聚合物染色,为水性溶液提供着色和为固体或半固体产品如洗涤剂提供颜色。蜡笔、油墨、抽水马桶着色剂、塑料、皂类和许多其它产品可使用该着色剂复合物着色。
本发明的复合物可用于对许多不同介质染色,包括热塑性复合物、热固性塑料和蜡,还可用于印刷油墨制剂中,所有仅作为例子。本发明的复合物具有聚合着色剂的有利特性,诸如高染色强度、理想的迁移特性和对塑料物理性质的最小影响。同时,基本所有类型和类别的发色团可用于实施本发明。然而,这样的发色团分子优选具有至少一个反应性位点(诸如乙烯砜)和一个阴离子官能团(诸如磺酸或羧酸官能度)以与阳离子化合物形成必要的复合物。阳离子铵基团与这样的酸(即,磺酸和/或羧酸)基团通过离子键结合。不完全理解季铵的阳离子部分与阴离子染料的阴离子部分之间的相互作用如何实施;然而,如上面所讨论的,很明显季铵化合物对阴离子染料比对这种季铵化合物通常所结合的阴离子抗衡离子具有更大的亲和力。对于阴离子染料也是如此,其对阳离子季铵化合物比对阳离子抗衡离子具有更大亲和力。随后,当复合时,两种组分的自由抗衡离子共同反应形成前述不需要的盐,其需要从所得复合物中去除(至少大部分去除)以提供理想的前述有利特性。剩余盐的可容许水平和由此本发明对本发明复合物基本不含盐的定义为至多约5,000ppm。理论上,不可能从该复合物中去除全部不需要的盐;然而,在如此低的可容许和可达到的盐的水平下,可获得理想的迁移和着色剂特性。当然,完全无盐的水平将是最优选的,尽管这样的水平,如上所述地,几乎是不可能实现的。
术语烃意图包含反应性染料基本不溶于其中的基本由碳和氢组成的任何有机组成。更具体而言,烃意图包含燃料(诸如煤油)、石油醚、油、稀释剂、溶剂和未修饰反应性染料基本不溶于其中的其它任何含碳氢的有机组成。术语蜡意图包含未修饰反应性染料基本不溶于其中的任何蜡或蜡样物质。蜡通常定义为高分子量脂肪酸与高分子量醇的酯或任何这样的酯的混合物。更具体类型的这种蜡包括矿物蜡,诸如石蜡、褐煤蜡、地蜡、微晶、泥土等;动物蜡,诸如蜂蜡、胡蜂蜡、中国蜡(虫蜡)蜡;植物蜡,诸如棕榈蜡、甘蔗蜡、烛树蜡、亚麻蜡;和合成蜡,诸如Fischer-Tropsch蜡、聚乙烯蜡。蜡组合物可模制为不同制品,诸如蜡烛和蜡笔(添加足够量的合适增塑剂,诸如硬脂酸)、耳塞蜡。着色剂通常以如下比例添加:蜡介质的约0.005-约15.0wt%,优选约0.01-约10.0%,更优选约0.05-约5.0%,最优选约0.1-约3.0%。
以下实施例提供用于说明,并且不应被视为限制本发明的范围。
实施例:从反应性染料合成着色复合物:
实施例1:从反应红120、3-(2-乙基己氧基)丙胺和336合成红色复合物
将14.7克反应红120(50%染料含量)、2.81克3-(2-乙基己氧基)-丙胺、0.84克碳酸氢钠和30mL水装入配有搅拌器、温控和冷凝器的反应器中。混合物加热至80℃数小时,直到TLC监控原材料反应红120耗尽。随后缓慢添加12.1克336,并于80℃搅拌1小时。反应混合物冷却至室温,并析出暗红色固体。将固体过滤并用水洗涤以去除盐。得到24.1克红色固体,色值为12.8。
实施例2:从反应红120、Jeffamine M-1000和336合成红色复合物
将14.7克反应红120(50%染料含量)、11克Jeffamine M-1000、0.84克碳酸氢钠和50mL水装入配有搅拌器、温控和冷凝器的反应器中。混合物加热至80℃数小时,直到TLC监控原材料反应红120耗尽。随后缓慢添加12.1克336,并于80℃搅拌1小时。反应混合物冷却至室温,添加150mL氯仿。氯仿层用水洗涤以去除盐。在去除氯仿后得到20.6克暗红色糊状物,色值为9.6。
实施例3:从反应红120、Polyglycol Amine H-163和C/25合成红色复合物
将14.7克反应红120(50%染料含量)、2.0克Polyglycol Amine H-163、0.84克碳酸氢钠和60mL水装入配有搅拌器、温控和冷凝器的反应器中。混合物加热至80℃数小时,直到TLC监控原材料反应红120耗尽。随后缓慢添加18.1克Ethoquad C/25,并于80℃搅拌1小时。反应混合物冷却至室温,添加150mL氯仿。氯仿层用水洗涤以去除盐。在去除氯仿后得到27.5克暗红色粘稠液体,在甲醇中在544nm的最大吸收峰处的色值为5.8。
实施例4:从反应红120、Jeffamine M-1000和苄基三苯基氯化鏻合成红色复合物
将7.35克反应红120(50%染料含量)、5.0克Jeffamine M-1000、0.42克碳酸氢钠和50mL水装入配有搅拌器、温控和冷凝器的反应器中。混合物加热至80℃数小时,直到TLC监控原材料反应红120耗尽。随后缓慢添加5.85克苄基三苯基氯化鏻并于80℃搅拌1小时。反应混合物冷却至室温并添加150mL氯仿。氯仿层用水洗涤以去除盐。在去除氯仿后得到15.4克暗红色糊状物,在543nm的最大吸收处的色值为8.3。
实施例5:从反应红120、二甘醇胺和苄基三苯基氯化鏻合成红色复合物
将14.69克反应红120(50%染料含量)、2.1克二甘醇胺、1.05克碳酸氢钠和50mL水装入配有搅拌器、温控和冷凝器的反应器中。混合物加热至80℃数小时,直到TLC监控原材料反应红120耗尽。随后缓慢添加11.8克苄基三苯基氯化鏻并于80℃搅拌1小时。反应混合物冷却至室温,并从液相析出红色固体。将暗红色固体用大量水清洗并干燥。所得红色粉末在甲醇中543nm的最大吸收处的色值为8.3。
实施例6:从反应黄81、Jeffamine M-1000和Ethoquad C/25合成黄色复合物
将8.2克反应黄81、11克Jeffamine M-1000、0.84克碳酸氢钠、26.9克Ethoquad C/25和50mL水装入配有搅拌器、温控和冷凝器的反应器中。混合物加热至80℃数小时,直到TLC监控原材料反应黄81耗尽。反应混合物冷却至室温,添加150mL氯仿。氯仿层用水洗涤以去除盐。在去除氯仿后得到43.9克暗黄色粘稠液体,在366nm的吸收峰处的色值为2.8。
实施例7:从反应紫5、Polyglycol Amine H-163和Aliquat 336合成紫色复合物
将7.36克反应紫5、4.89克Polyglycol Amine H-163、0.84克碳酸氢钠、8.09克336和50mL水装入配有搅拌器、温控和冷凝器的反应器中。混合物加热至80℃数小时,直到TLC监控原材料反应紫5完全反应。反应混合物冷却至室温,添加150mL氯仿。氯仿层用水洗涤以去除盐。在去除氯仿后得到14.1克暗紫色糊状物,在565nm的吸收峰处的色值为6.2。
实施例8:从反应黑5、二甘醇胺和336合成黑色复合物
将36.08克反应黑5(染料%是55%)、6.3克二甘醇胺、3.28克碳酸氢钠和50mL水装入配有搅拌器、温控和冷凝器的反应器中。混合物加热至60℃数小时,直到TLC监控原材料反应黑5完全反应。随后将16.2克336于60℃缓慢添加至反应混合物,并搅拌1小时。反应混合物冷却至室温,析出暗蓝黑色固体。将固体用大量水洗涤数次以去除无机盐。所得的暗蓝黑色固体在甲醇中在587nm处具有吸收峰。
实施例9:从反应蓝4、二甘醇胺和三己基十四烷基氯化鏻合成蓝色复合物
9.1克反应蓝4(染料%为35%)、2.1克二甘醇胺、1.0克碳酸氢钠和30mL水装入配有搅拌器、温控和冷凝器的反应器中。混合物加热至60℃数小时,直到TLC监控原材料反应蓝4完全反应。随后将5.19克三己基十四烷基氯化鏻于60℃缓慢添加至反应混合物并搅拌1小时。反应混合物冷却至室温,析出暗蓝色固体。将固体用大量水洗涤数次以去除无机盐。所得的暗蓝色固体在甲醇中在628nm处具有吸收峰。
实施例10:从反应蓝4、二甘醇胺和苄基三苯基氯化鏻合成蓝色复合物
将9.03克反应蓝4(35%染料含量)、2.21克二甘醇胺、1.03克碳酸氢钠和50mL水装入配有搅拌器、温控和冷凝器的反应器中。混合物加热至80℃数小时,直到TLC监控原材料反应蓝4耗尽。随后缓慢添加4.02克苄基三苯基氯化鏻并于80℃搅拌1小时。反应混合物冷却至室温,并从液相析出蓝色固体。将暗蓝色固体用大量水洗涤并干燥。所得的8.63克蓝色粉末在甲醇中在591nm的最大吸收处具有6.05的色值。
着色剂复合物的应用
实施例A:制造作为合成皮革的有色聚氨酯涂层
该实施例验证了根据本发明的合成皮革制品的制造。将5份实施例1的红色聚合着色剂复合物与100份得自Stahl的聚氨酯树脂SU-9704充分混合。将该红色聚氨酯树脂溶液直接涂布到市售的用硅酮处理过的镜面防粘纸上,形成厚度约15微米的薄膜涂层。然后将厚度为1mm的基础基材(base substrate)(厚度为80微米的非织造纤维片和浸渍/涂布并固化于一侧上的聚氨酯高弹体)压制/粘合到该薄膜涂层上。随后,将组件在烘箱中加热至约120℃的温度并在该温度保持约3分钟。随后将组件从烘箱中取出并冷却至室温,随后将防粘纸从组件上剥离。由此得到具有红色皮层的合成皮革制品。而且,在防粘纸上检测不到可见的红色,这意味着没有红色着色剂迁移到防粘纸上。对合成皮革制品进行皮革测试以检测皮革迁移。将合成皮革制品在70℃烘箱中用干净的白色PVC或PU合成皮革样品按压24小时。随后测量白色PVC或PVC合成皮革样品上从本发明的合成皮革转移的颜色。在PVC或PU合成测试皮革表面上检测不到可见的红色。
实施例B:着色蜡的制备
将实施例1的着色剂复合物添加到熔融的石蜡(熔点130-150°F)中,其量为约0.01wt%,搅拌直到熔融蜡变为均匀的浅红色泽。随后将着色的熔融蜡倾倒入模具(nalgene烧杯)中并使其冷却形成均匀的浅红色着色蜡。
实施例C:着色烃燃料和液体的制备
将实施例4的着色剂复合物添加到煤油中,其量为约0.01wt%,搅拌直到组合物变为均匀的浅红色泽。
实施例D:着色PVA膜的制造
将实施例3的着色剂复合物添加到30%wt PVA水溶液(MW~108,000)中,其量为约2wt%,搅拌直到组合物变为均匀的红色溶液。通过在光滑的纸基材上去水(drawdown)并于105℃烘箱中干燥5分钟获得均匀的红色独立式膜。
实施例E:着色PU泡沫的制备
将实施例8的着色剂复合物添加到聚氨酯泡沫制剂(4份/100份多元醇)中。得到均匀的黑色聚氨酯泡沫。
实施例F:着色液体多功能清洁剂的制备
将0.1克实施例6的黄色复合物添加到100克未着色的液体多功能清洁剂中。得到澄清的均匀的黄色多功能清洁剂。
实施例G:着色液体洗涤剂的制备
将0.1克实施例3的红色复合物添加到100克未着色的AATCC标准液体洗涤剂中。得到澄清的、均匀的红色液体洗涤剂。
本文中所引用的所有参考文件,包括公开出版物、专利申请和专利,均通过引用在此并入,其程度如同每篇参考文件被单独和具体表明通过引用并入一样,并且以其整体中本文中阐述。
除非在本文中另外表明或者在上下文中明确矛盾,在描述本发明的上下文中(尤其是在后面的权利要求书的上下文中)术语“一/一个/一种”和“所述/该”以及类似指示对象的使用应解释为同时涵盖单数和复数。除非另外表明,术语“包括”、“具有”、“包含”和“含有”应解释为开放式术语(即,表示“包括,但不限于”)。除非另外表明,本文中对数值范围的阐述仅意图用作单独设计落入该范围内的每个独立值的简写方法,每个独立值包含在说明书中,如果其在本文中被单独述及一样。除非在本文中另外表明,本文所述的所有方法可以任何合适的顺序实施。除非另外要求,本文提供的任何和所有实施例或示例性语言(例如,“诸如”)的使用仅意图更高地解释发明,并非对发明范围提出限制。说明书中没有任何语言应理解为表示任何未被要求的要素对发明实施是不可缺少的。
本发明的优选实施方式在本文中阐述,包括发明人已知实施发明的最佳方式。在阅读前述说明书时,本领域技术人员能容易地做出那些优选实施方式的变化。发明人预计技术人员能适当采用这样的变化,并且发明人意图以不同于本文具体所述者不同的其它方式实施本发明。因此,本发明包括适用法律所允许的所附权利要求中所述主题的所有修改和等价范围。另外,除非在本文中另外表明或者上下文中明确矛盾,其所有可能变化中上述要素的任何组合均涵盖在本发明中。
Claims (1)
1.具有以下通用结构(I)的有机着色剂复合物:
(I) ABn(DE)mTxQy
其中A是有机发色团;B是直接或通过连接基团共价结合到A的亲电反应基团;D是共价结合B和E的亲核连接基团,其选自NR、O、S和4-氧苯胺基(--HN--Ph--O--);其中R选自H、烷基、芳基和E;E是有机部分或端基;T是与A共价结合的离子基团,其为阴离子或阳离子的,优选阴离子基团;Q是通过与T的离子相互作用结合到有机发色团的抗衡离子;n、m、x和y是1–10的独立整数,且它们可相同或不同。
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PCT/US2015/026753 WO2015164299A1 (en) | 2014-04-22 | 2015-04-21 | Organic colorant complexes from reactive dyes and articles containing the same |
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