CA1112797A - Polymeric colour indicators and a method of their preparation - Google Patents
Polymeric colour indicators and a method of their preparationInfo
- Publication number
- CA1112797A CA1112797A CA289,155A CA289155A CA1112797A CA 1112797 A CA1112797 A CA 1112797A CA 289155 A CA289155 A CA 289155A CA 1112797 A CA1112797 A CA 1112797A
- Authority
- CA
- Canada
- Prior art keywords
- derivatives
- group
- sulpho
- hydroxy
- amino
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title claims description 6
- -1 N-substituted amides Chemical class 0.000 claims abstract description 18
- 239000007793 ph indicator Substances 0.000 claims abstract description 14
- 239000000178 monomer Substances 0.000 claims abstract description 11
- 150000001408 amides Chemical class 0.000 claims abstract description 8
- 238000005859 coupling reaction Methods 0.000 claims abstract description 8
- 150000002148 esters Chemical class 0.000 claims abstract description 7
- 230000008878 coupling Effects 0.000 claims abstract description 6
- 238000010168 coupling process Methods 0.000 claims abstract description 6
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims abstract description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims abstract description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000005395 methacrylic acid group Chemical class 0.000 claims abstract description 4
- 239000012736 aqueous medium Substances 0.000 claims abstract description 3
- 238000006116 polymerization reaction Methods 0.000 claims abstract 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 12
- 150000001412 amines Chemical class 0.000 claims description 12
- 229920000642 polymer Polymers 0.000 claims description 12
- 150000004982 aromatic amines Chemical class 0.000 claims description 6
- 239000007822 coupling agent Substances 0.000 claims description 5
- AAPMEIVPRREKGM-UHFFFAOYSA-N 5-(n-ethylanilino)-2-methylpent-1-en-3-one Chemical compound CC(=C)C(=O)CCN(CC)C1=CC=CC=C1 AAPMEIVPRREKGM-UHFFFAOYSA-N 0.000 claims description 4
- 150000001491 aromatic compounds Chemical class 0.000 claims description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 4
- 150000002989 phenols Chemical class 0.000 claims description 4
- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 claims description 3
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 claims description 3
- GTLFLKPYMGGXKO-UHFFFAOYSA-N n-[4-[ethyl-(4-methyl-3-oxopent-4-enyl)amino]phenyl]acetamide Chemical compound CC(=C)C(=O)CCN(CC)C1=CC=C(NC(C)=O)C=C1 GTLFLKPYMGGXKO-UHFFFAOYSA-N 0.000 claims description 3
- 150000003254 radicals Chemical class 0.000 claims description 2
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 claims 2
- NIXIJMXBXHWPEK-UHFFFAOYSA-N 2-methyl-5-phenyl-4h-pyrazol-3-one Chemical class C1C(=O)N(C)N=C1C1=CC=CC=C1 NIXIJMXBXHWPEK-UHFFFAOYSA-N 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 239000012954 diazonium Substances 0.000 abstract description 2
- 150000001989 diazonium salts Chemical class 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 239000002609 medium Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000003973 paint Substances 0.000 description 4
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 2
- 238000013494 PH determination Methods 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Chemical compound CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000007670 refining Methods 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000012798 spherical particle Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229950000244 sulfanilic acid Drugs 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- CLRSZXHOSMKUIB-UHFFFAOYSA-M benzenediazonium chloride Chemical compound [Cl-].N#[N+]C1=CC=CC=C1 CLRSZXHOSMKUIB-UHFFFAOYSA-M 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 235000013365 dairy product Nutrition 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical class [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- 229940063559 methacrylic acid Drugs 0.000 description 1
- 125000002496 methyl group Chemical class [H]C([H])([H])* 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000001139 pH measurement Methods 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N31/00—Investigating or analysing non-biological materials by the use of the chemical methods specified in the subgroup; Apparatus specially adapted for such methods
- G01N31/22—Investigating or analysing non-biological materials by the use of the chemical methods specified in the subgroup; Apparatus specially adapted for such methods using chemical indicators
- G01N31/221—Investigating or analysing non-biological materials by the use of the chemical methods specified in the subgroup; Apparatus specially adapted for such methods using chemical indicators for investigating pH value
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Analytical Chemistry (AREA)
- Molecular Biology (AREA)
- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Biophysics (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Immunology (AREA)
- Pathology (AREA)
- Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CSPV6778-76 | 1976-10-21 | ||
| CS766778A CS188348B1 (en) | 1976-10-21 | 1976-10-21 | Polymere colour indicators ph and method of preparation thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1112797A true CA1112797A (en) | 1981-11-17 |
Family
ID=5415563
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA289,155A Expired CA1112797A (en) | 1976-10-21 | 1977-10-20 | Polymeric colour indicators and a method of their preparation |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4166804A (enExample) |
| CA (1) | CA1112797A (enExample) |
| CS (1) | CS188348B1 (enExample) |
| DE (1) | DE2747434A1 (enExample) |
| GB (1) | GB1579069A (enExample) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4287153A (en) * | 1978-09-20 | 1981-09-01 | Towsend Marvin S | Disposable article with non-leachable saline water indicator |
| US4547202A (en) * | 1982-02-02 | 1985-10-15 | Atlantic Richfield Company | Hydrocarbon oils with improved pour points |
| AT381172B (de) * | 1983-08-26 | 1986-09-10 | Avl Verbrennungskraft Messtech | Verfahren zur bestimmung der ionenstaerke einer elektrolytloesung sowie messeinrichtung zur durchfuehrung des verfahrens |
| GB8401166D0 (en) * | 1984-01-17 | 1984-02-22 | Bevaloid Ltd | Labelled polymer compositions |
| US4801655A (en) * | 1985-06-21 | 1989-01-31 | Gould, Inc. | Fiber optic pH sensor having low drift rate |
| US4793977A (en) * | 1987-04-09 | 1988-12-27 | Cape Cod Research, Inc. | Colorimetric detector for monitoring oil degradation |
| US6541260B1 (en) | 2001-04-19 | 2003-04-01 | Blake Pariseau | Device for detecting and indicating fluid properties |
| KR100505021B1 (ko) * | 2002-07-25 | 2005-08-01 | 박상규 | 진단계측기용 센서 |
| US20100210745A1 (en) * | 2002-09-09 | 2010-08-19 | Reactive Surfaces, Ltd. | Molecular Healing of Polymeric Materials, Coatings, Plastics, Elastomers, Composites, Laminates, Adhesives, and Sealants by Active Enzymes |
| US20100233146A1 (en) * | 2002-09-09 | 2010-09-16 | Reactive Surfaces, Ltd. | Coatings and Surface Treatments Having Active Enzymes and Peptides |
| US20110070376A1 (en) * | 2002-09-09 | 2011-03-24 | Reactive Surfaces, Ltd. | Anti-fouling Paints & Coatings |
| US20040109853A1 (en) * | 2002-09-09 | 2004-06-10 | Reactive Surfaces, Ltd. | Biological active coating components, coatings, and coated surfaces |
| US20090238811A1 (en) * | 2002-09-09 | 2009-09-24 | Mcdaniel C Steven | Enzymatic Antimicrobial and Antifouling Coatings and Polymeric Materials |
| US20060008912A1 (en) * | 2004-07-09 | 2006-01-12 | Simon Patrick L | Temporary visual indicators for paint and other compositions |
| US8388904B1 (en) | 2008-12-22 | 2013-03-05 | Reactive Surfaces, Ltd., Llp | Equipment decontamination system and method |
| DE102011003517A1 (de) * | 2011-02-02 | 2012-08-02 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Kleidungsstück |
| US8945936B2 (en) * | 2011-04-06 | 2015-02-03 | Fresenius Medical Care Holdings, Inc. | Measuring chemical properties of a sample fluid in dialysis systems |
| US9688946B2 (en) | 2012-12-10 | 2017-06-27 | Milliken & Company | Cleaning composition and method for using the same |
| WO2016071465A1 (en) * | 2014-11-05 | 2016-05-12 | Tap Biosystems (Phc) Limited | Luminescent ruthenium (ii) complexes and their use in ph sensors |
| JP6594280B2 (ja) * | 2016-09-21 | 2019-10-23 | 学校法人東京電機大学 | 広範囲ｐＨ指示用共重合体及びその合成方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2732382A (en) * | 1956-01-24 | -chjoh | ||
| US2929829A (en) * | 1956-10-12 | 1960-03-22 | Union Carbide Corp | Organosilicon acylamino compounds and process for producing the same |
| US3544484A (en) * | 1967-12-18 | 1970-12-01 | American Standard Inc | Optical ph indicator comprising aromatic aminoazo dye and inert polymer containing carbonyl radicals |
| US4029598A (en) * | 1969-03-14 | 1977-06-14 | E. Merck A. G. | Non-bleeding indicator and dyes therefor |
| CS176421B1 (enExample) * | 1972-11-06 | 1977-06-30 | ||
| US3904373A (en) * | 1973-10-26 | 1975-09-09 | Gerald Bruce Harper | Indicators covalently bound to insoluble carriers |
-
1976
- 1976-10-21 CS CS766778A patent/CS188348B1/cs unknown
-
1977
- 1977-10-14 US US05/842,273 patent/US4166804A/en not_active Expired - Lifetime
- 1977-10-20 CA CA289,155A patent/CA1112797A/en not_active Expired
- 1977-10-20 GB GB43679/77A patent/GB1579069A/en not_active Expired
- 1977-10-21 DE DE19772747434 patent/DE2747434A1/de active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| GB1579069A (en) | 1980-11-12 |
| DE2747434A1 (de) | 1978-04-27 |
| DE2747434C2 (enExample) | 1988-01-14 |
| US4166804A (en) | 1979-09-04 |
| CS188348B1 (en) | 1979-03-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |