DE1116393B - Process for increasing the lightfastness of molded polyamides - Google Patents
Process for increasing the lightfastness of molded polyamidesInfo
- Publication number
- DE1116393B DE1116393B DED31887A DED0031887A DE1116393B DE 1116393 B DE1116393 B DE 1116393B DE D31887 A DED31887 A DE D31887A DE D0031887 A DED0031887 A DE D0031887A DE 1116393 B DE1116393 B DE 1116393B
- Authority
- DE
- Germany
- Prior art keywords
- increasing
- lightfastness
- polyamides
- molded
- nitrogen
- 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.)
- Pending
Links
- 239000004952 Polyamide Substances 0.000 title claims description 8
- 229920002647 polyamide Polymers 0.000 title claims description 8
- 238000000034 method Methods 0.000 title claims description 6
- 239000000126 substance Substances 0.000 claims description 7
- 230000000694 effects Effects 0.000 claims description 3
- 150000003918 triazines Chemical class 0.000 claims description 3
- 150000000183 1,3-benzoxazoles Chemical class 0.000 claims description 2
- 150000001565 benzotriazoles Chemical class 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 3
- 230000037072 sun protection Effects 0.000 claims 1
- 239000004611 light stabiliser Substances 0.000 description 6
- 239000012965 benzophenone Substances 0.000 description 5
- 239000000835 fiber Substances 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 229920002302 Nylon 6,6 Polymers 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 239000012433 hydrogen halide Substances 0.000 description 2
- 229910000039 hydrogen halide Inorganic materials 0.000 description 2
- 230000003711 photoprotective effect Effects 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 230000000475 sunscreen effect Effects 0.000 description 2
- 239000000516 sunscreening agent Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- 101100322245 Caenorhabditis elegans des-2 gene Proteins 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000004224 protection Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000000985 reactive dye Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/35—Heterocyclic compounds
- D06M13/355—Heterocyclic compounds having six-membered heterocyclic rings
- D06M13/358—Triazines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
- C08K5/3477—Six-membered rings
- C08K5/3492—Triazines
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Artificial Filaments (AREA)
Description
Verfahren zur Erhöhung der Lichtbeständigkeit von geformten Polyamiden Eine große Anzahl organischer Substanzen zur Erhöhung der Lichtbeständigkeit von Kunststoffen ist bekannt. Diese werden entweder dem Kunststoff vor oder nach der Verformung einverleibt. Es handelt sich bei diesen Lichtschutzmitteln meistens um Verbindungen, die ultraviolette Strahlen absorbieren.Process for increasing the lightfastness of molded polyamides A large number of organic substances to increase the light resistance of Plastics is known. These are either before or after the plastic Deformation incorporated. These sunscreens are mostly Compounds that absorb ultraviolet rays.
Einzelne Substanzen besitzen jedoch auch Schutzwirkung, ohne daß sie ultraviolette Strahlen absorbieren.However, individual substances also have protective effects without them absorb ultraviolet rays.
Die meisten der bekannten Lichtschutzmittel zeigen jedoch den Nachteil, daß sie schon nach wenigen Wäschen aus den geformten Gebilden, wie Fasern und Fäden, so weit herausgewaschen werden, daß die Lichtschutzwirkung verlorengeht. Most of the known light stabilizers, however, have the disadvantage that after just a few washes they leave the formed structures, such as fibers and threads, be washed out so far that the light protection effect is lost.
Gegenstand der vorliegenden Erfindung ist ein Verfahren zur Erhöhung der Lichtbeständigkeit von geformten Polyamiden, dadurch gekennzeichnet, daß als Lichtschutzmittel substituierte Triazine verwendet werden, die mit demPolyamid chemische Bindungen eingehen und als Substituenten organische Reste mitLichtschutzwirkung enthalten, z. B. auf Grundlage von Polyoxybenzophenonen, Benztriazolen bzw. Benzoxazolen. The present invention relates to a method for increasing the light resistance of molded polyamides, characterized in that as Light stabilizers substituted triazines are used, which chemical with the polyamide Form bonds and, as substituents, organic radicals with a photoprotective effect included, e.g. B. based on polyoxybenzophenones, benzotriazoles or benzoxazoles.
Läßt man Verbindungen dieser Art auf Polyamidfasern und-faden oder-gewebe oder-gewirke einwirken, gegebenenfalls unter Zusatz entsprechender Mengen organischer oder anorganischer Basen zum Abfangen des frei werdenden Halogenwasserstoffes, so wird das Lichtschutzmittel ohne praktische Einbuße in seiner Wirksamkeit an das Polyamid gebunden. One leaves connections of this kind on polyamide fibers and threads or fabrics or knitted fabrics act, if necessary with the addition of appropriate amounts of organic or inorganic bases to trap the liberated hydrogen halide, see above the light stabilizer is effective against the Polyamide bonded.
Es ist an sich bekannt, daß ein Teil der sogenannten » Reaktivfarbstoffe « in der Weise hergestellt wird, das an den Farbstoff durch Umsetzung mit Cyanurchlorid ein Triazinring mit mindestens einem noch aktiven Halogenatom gekoppelt wird. Die so umgesetzten Farbstoffe werden beim Färbevorgang an die Fasergrundlage chemisch gebunden. Es war jedoch nicht vorauszusehen, daß eine Verknüpfung von als Lichtschutzmittel in Frage kommenden organischen Verbindungen mit Cyanurchlorid fast keine Einwirkung auf dieAbsorptionskurve eines Ultraviolett absorbierenden Stoffes hat, selbst dann nicht, wenn man das aus der Umsetzung resultierende Produkt unter Halogenwasserstoffabspaltung an einen Fasergrundstoff bindet. It is known per se that some of the so-called »reactive dyes «In the way that the dye is produced by reacting it with cyanuric chloride a triazine ring is coupled with at least one still active halogen atom. the Dyes converted in this way are chemically applied to the fiber base during the dyeing process bound. However, it was not foreseeable that a combination of as a light stabilizer organic compounds with cyanuric chloride in question have almost no effect on the absorption curve of an ultraviolet absorbent, even then not if the product resulting from the reaction is split off with elimination of hydrogen halide binds to a fiber base.
Die sehr viel größere Waschbeständigkeit von reaktionsfähigen Lichtschutzmitteln gegenüber den entsprechenden, gleichfalls als Lichtschutzmittel angewendeten Ausgangssubstanzen zeigt das folgende Beispiel. The much greater resistance to washing of reactive sunscreens compared to the corresponding starting substances, which are also used as light stabilizers shows the following example.
Herstellung des als Ausgangsstoff dienenden Lichtschutzmittels Äquivalente Mengen 2,4-Dioxybenzophenon und Cyanurchlorid werden in Eiswasser in Gegenwart einer äquivalenten Menge Natriumhydroxyd zur Reaktion gebracht ; das 2,4-Dichlor-6- (3-oxy-4-benzoyl-phenoxy)-triazin fällt als farblose Substanz aus. Production of the light stabilizer used as the starting material equivalents Amounts of 2,4-dioxybenzophenone and cyanuric chloride are present in ice water one equivalent amount of sodium hydroxide reacted; 2,4-dichloro-6- (3-oxy-4-benzoyl-phenoxy) -triazine precipitates as a colorless substance.
Mit ihm werden folgende Versuche durchgeführt : 200-m-Faden aus Polyhexamethylenadipamid mit 2°/o Titanoxydzusatz, Stärke 40 den, 13 Fibrillen, wird in einer Lösung von 1,69 g 2,4-Dichlor-6- (3-oxy-4-benzoyl-phenoxy)-triazin und 0,8 g Pyridin in 20Q ml Aceton 3 Stunden zum Rückfluß erhitzt, die Fasern mit Wasser kurz gespült und bei 100°C getrocknet. The following tests are carried out with it: 200 m thread made of polyhexamethylene adipamide with 2% added titanium oxide, thickness 40 denier, 13 fibrils, is dissolved in a solution of 1.69 g of 2,4-dichloro-6- (3-oxy-4-benzoyl-phenoxy) -triazine and 0.8 g of pyridine in 20Q ml of acetone heated to reflux for 3 hours, the fibers rinsed briefly with water and dried at 100 ° C.
Der Gehalt an wirksamer Substanz (2,4-Dioxybenzophenon) wird photometrisch in konzentrierter Schwefelsäure bestimmt.The content of the active substance (2,4-dioxybenzophenone) is photometric determined in concentrated sulfuric acid.
Die nachfolgende Tabelle gibt die gefundenen Werte vor und nach einer bis drei Wäschen wieder im Vergleich zu dem Gehalt, den man findet, wenn das gleiche Material unter den gleichen Bedingungen mit unsubstituiertem 2,4-Dioxy-benzophenon behandelt wird. The following table shows the values found before and after a up to three washes again compared to the salary one finds if the same Material under the same conditions with unsubstituted 2,4-dioxy-benzophenone is treated.
Gehalt an 2,4-Dioxy-benzophenon in Polyhexamethylenadipamid bzw.
an lichtschutzwirksamer Substanz,
berechnet auf 2,4-Dioxy-benzophenon
in Gewichtsprozenten
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DED31887A DE1116393B (en) | 1959-11-14 | 1959-11-14 | Process for increasing the lightfastness of molded polyamides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DED31887A DE1116393B (en) | 1959-11-14 | 1959-11-14 | Process for increasing the lightfastness of molded polyamides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1116393B true DE1116393B (en) | 1961-11-02 |
Family
ID=7041099
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DED31887A Pending DE1116393B (en) | 1959-11-14 | 1959-11-14 | Process for increasing the lightfastness of molded polyamides |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1116393B (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1270277B (en) * | 1964-09-29 | 1968-06-12 | Ici Ltd | Process for the production of stabilized polyamides |
| EP0717140A3 (en) * | 1994-12-13 | 1996-06-26 | Ciba Geigy Ag | |
| CN102584727A (en) * | 2011-11-28 | 2012-07-18 | 江南大学 | Method for synthesizing novel reactive ultraviolet absorbent and application thereof |
| CN103088633A (en) * | 2012-12-21 | 2013-05-08 | 江南大学 | Method for improving light-perspiration color fastness of reactive brilliant red dyed fabric |
| CN118085582A (en) * | 2024-04-26 | 2024-05-28 | 广东胜宇电缆实业有限公司 | A high-insulation photovoltaic cable material and preparation method thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1121229A (en) * | 1953-03-12 | 1956-07-25 | Degussa | Process for treating polyamide fibers and fibers conforming to those obtained |
| GB755519A (en) * | 1953-08-14 | 1956-08-22 | Ici Ltd | Water-soluble organic nitrogen compounds |
-
1959
- 1959-11-14 DE DED31887A patent/DE1116393B/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1121229A (en) * | 1953-03-12 | 1956-07-25 | Degussa | Process for treating polyamide fibers and fibers conforming to those obtained |
| GB755519A (en) * | 1953-08-14 | 1956-08-22 | Ici Ltd | Water-soluble organic nitrogen compounds |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1270277B (en) * | 1964-09-29 | 1968-06-12 | Ici Ltd | Process for the production of stabilized polyamides |
| EP0717140A3 (en) * | 1994-12-13 | 1996-06-26 | Ciba Geigy Ag | |
| CN102584727A (en) * | 2011-11-28 | 2012-07-18 | 江南大学 | Method for synthesizing novel reactive ultraviolet absorbent and application thereof |
| CN103088633A (en) * | 2012-12-21 | 2013-05-08 | 江南大学 | Method for improving light-perspiration color fastness of reactive brilliant red dyed fabric |
| CN118085582A (en) * | 2024-04-26 | 2024-05-28 | 广东胜宇电缆实业有限公司 | A high-insulation photovoltaic cable material and preparation method thereof |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1282598B (en) | Process for making cellulosic material flame resistant | |
| EP0572923A1 (en) | Process for the "wash-and-wear" finishing of cellulose textile, without formaldehyde | |
| DE1156978B (en) | Process for finishing polyamide material | |
| DE1116393B (en) | Process for increasing the lightfastness of molded polyamides | |
| CH383326A (en) | Process for improving the mechanical properties of textiles | |
| EP0057668A2 (en) | Salts of phosphonic acids, their manufacture and their use for flame-proofing organic fibers | |
| EP0616071A1 (en) | Process for the treatment of fibrous materials with triazin derivatives | |
| DE1129451B (en) | Process to improve the colorability of heat-treated polyvinyl alcohol threads | |
| DE1594947C3 (en) | Phosphorus-containing, curable and water-soluble aminoplasts, as well as their use for making textile material flame-resistant | |
| EP0359039A2 (en) | Process for the wash-and-wear finishing of textiles | |
| DE2110415B2 (en) | Process for making cellulosic fiber materials flame resistant | |
| DE1094225B (en) | Process for crease and shrink-proof finishing of cellulose textiles | |
| DE1418756A1 (en) | Process for the production of cellulose or cellulose derivatives with improved light stability | |
| DE1114494B (en) | Process for the production of organic compounds which can be reacted with cellulose acetate or polyamide fibers and which absorb ultraviolet rays | |
| DE1010944B (en) | Process for chlorinating wool | |
| DE1921527B2 (en) | Process for the antistatic treatment of moldings made of linear crystallizable polyesters | |
| DE1940799A1 (en) | Process for the preparation of condensation products from methylene-bis-acrylamide and formaldehyde | |
| DE1047745B (en) | Process for the resin finishing of textiles | |
| DE1150651B (en) | Process for the wash-resistant flame-retardant finish on cellulose textiles | |
| DE1419364C (en) | ||
| AT233317B (en) | Process for protecting organic substances against microorganisms | |
| DE1011869B (en) | Process for upgrading cellulose or cellulose derivatives | |
| WO1993015138A1 (en) | Method of improving the heat-insulation properties of polyamide 6.6 filaments, and filaments produced by this method | |
| DE901408C (en) | Process for making woolen material shrink-proof | |
| AT158387B (en) | Process for the refinement of natural or artificial fibers. |