GB2031006A - Isoindoline Derivatives and Their Use - Google Patents
Isoindoline Derivatives and Their Use Download PDFInfo
- Publication number
- GB2031006A GB2031006A GB7928628A GB7928628A GB2031006A GB 2031006 A GB2031006 A GB 2031006A GB 7928628 A GB7928628 A GB 7928628A GB 7928628 A GB7928628 A GB 7928628A GB 2031006 A GB2031006 A GB 2031006A
- Authority
- GB
- United Kingdom
- Prior art keywords
- styrene
- parts
- compound
- acrylonitrile
- stable
- 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.)
- Granted
Links
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical class C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 title claims abstract description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 3
- 229920001169 thermoplastic Polymers 0.000 claims abstract description 3
- 239000004416 thermosoftening plastic Substances 0.000 claims abstract description 3
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 17
- 229920001577 copolymer Polymers 0.000 claims description 14
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 239000004793 Polystyrene Substances 0.000 claims description 6
- 229920002223 polystyrene Polymers 0.000 claims description 6
- 229920000193 polymethacrylate Polymers 0.000 claims description 3
- 229920003048 styrene butadiene rubber Polymers 0.000 claims description 3
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 claims description 2
- 238000004040 coloring Methods 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- 229920000058 polyacrylate Polymers 0.000 claims description 2
- 229920002239 polyacrylonitrile Polymers 0.000 claims description 2
- 239000004417 polycarbonate Substances 0.000 claims description 2
- 229920000515 polycarbonate Polymers 0.000 claims description 2
- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 abstract description 2
- 229920000728 polyester Polymers 0.000 abstract description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- RZVCEPSDYHAHLX-UHFFFAOYSA-N 3-iminoisoindol-1-amine Chemical compound C1=CC=C2C(N)=NC(=N)C2=C1 RZVCEPSDYHAHLX-UHFFFAOYSA-N 0.000 description 4
- 238000001746 injection moulding Methods 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 3
- 239000007859 condensation product Substances 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- LMKZNSKYLAQXJH-UHFFFAOYSA-N 2-(1-ethylbenzimidazol-2-yl)acetonitrile Chemical compound C1=CC=C2N(CC)C(CC#N)=NC2=C1 LMKZNSKYLAQXJH-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- DYWFJPNNNWXOAK-UHFFFAOYSA-N 2-(1-methylbenzimidazol-2-yl)acetonitrile Chemical compound C1=CC=C2N(C)C(CC#N)=NC2=C1 DYWFJPNNNWXOAK-UHFFFAOYSA-N 0.000 description 1
- BWOVACANEIVHST-UHFFFAOYSA-N 2-(1h-benzimidazol-2-yl)acetonitrile Chemical compound C1=CC=C2NC(CC#N)=NC2=C1 BWOVACANEIVHST-UHFFFAOYSA-N 0.000 description 1
- XSQOQQAZUCYJKU-UHFFFAOYSA-N 2-(4-methyl-1h-benzimidazol-2-yl)acetonitrile Chemical compound CC1=CC=CC2=C1N=C(CC#N)N2 XSQOQQAZUCYJKU-UHFFFAOYSA-N 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical group O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- NTXGQCSETZTARF-UHFFFAOYSA-N buta-1,3-diene;prop-2-enenitrile Chemical compound C=CC=C.C=CC#N NTXGQCSETZTARF-UHFFFAOYSA-N 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/04—Isoindoline dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
New isoindoline derivatives of the formula <IMAGE> where R<1> and R<2> are methyl or ethyl and are identical or different give deep red colorations in thermoplastics, which are very heat-stable. The N,N'- dimethyl compound (I), for example, is stable in linear polyesters at up to 300 DEG C.
Description
SPECIFICATION - Isoindoline Derivatives and Their Use
The present invention relates to novel isoindoline derivatives and to their use for masscoloring of thermo-plastics.
The novel isoindoline derivatives have the formula
where R1 and R2 are methyl or ethyl and may be identical or different.
In plastics, e.g. polystyrene, polyacrylonitrile, polyacrylate, polymethacrylate, polycarbonate, styrene/acrylonitrile/acrylate copolymers, styrene/butadiene/acrylonitrile copolymers, styrene/acrylonitrile copolymers and styrene/butadiene copolymers, the compounds of the formula(l) give deep red colorations which are very heat-stable. For example, compounds (I) are stable in polystyrene at up to 3000C. By way of comparison, the most closely related known compound, described in Example 2 of German
Laid-Open Application DOS 2,615,394 and obtained by condensing 1 -amino-3-iminoisoindolenine with 2 moles of 2-cyanomethylbenzimidazole is only stable at up to 2200 C. This behavior of compounds (I) was surprising and unforeseeable.
The compound of the formula I where R1=R2=-CH3 is stable at up to 3000C in polymers composed of styrene, acrylonitrile and acrylates or styrene and butadiene, and in linear polyesters.
In polymethacrylates, the compound is stable at up to 2800C.
A compound (I) can be prepared by condensing a 1,3-disubstituted isoindolenine, e.g. a 1-amino3imino or 1 -amino-3,3-bis-alkoxy-isoindolenine, with 2 molar proportions of the appropriate 1alkyl-2-cyanomethylbenz-imidazole(s), in the conventional manner.
The condensation is carried out in an organic medium. Examples of suitable media are alkanols, advantageously used in the presence of aliphatic C2-C4-carboxylic acids, or polar waterimmiscible solvents, e.g. nitro-benzene.
The condensation is as a rule complete in from 2 to 5 hours at from 80 to 1 200C. The condensation product may be isolated from the reaction mixture in the conventional manner.
The compound (I) is obtained directly in a pure form, in which it may be used for coloring plastics of the stated type.
The Examples, and Use Examples, which follow illustrate the invention. Parts and percentages in the Examples and Use Examples are by weight.
Example 1
2 parts of a 1 -amino-3-imino-isoindolenine glycol adduct (obtained by reacting ophthalodinitrile with ammonia in ethylene glycol) and 5 parts of 1 -methyl-2-(cyanomethyl)- benzimidazole in 120 parts of methanol and 20 parts of glacial acetic acid are stirred under reflux for 4 hours. When the mixture has cooled, it is filtered and the filter residue is washed with methanol and water, and is dried.
Yield: 1.66 parts of the compound of the formula I, where R1=R2=-CH in the form of red needles.
Example 2
7.8 parts of the compound
and 5.5 parts of 1-ethyl-2-(cyanomethyl)- benzimidazole are introduced into 95 parts of methanol and 20 parts of glacial acetic acid and the mixture is stirred under reflux for 2 hours.
When it has cooled, the condensation product is filtered off, washed with methanol and dried.
Yield: 4.6 parts of the compound of the formula I, where R1=-CH3 and R2=-C2H6,in the form of bright red needles.
Example 3 414 parts of a 1 -amino-3-imino-isoindolenine glycol adduct (cf. Example 1) and 8.55 parts of 1 methyl-2-(cyanomethyl)-benzimidazole in 120 parts of nitro-benzene are stirred for 3 hours at 1 0O0C. When the mixture has cooled, the condensation product is filtered off, washed with methanol, acetic acid and again with methanol, and dried.
Yield: 7.6 parts of the compound of the formula I, where R1=R2=-CH3, in the form of red needles. The compound has the same properties as those of the compound obtained in Example 1.
Example 4
5.9 parts of the 1 -amino-3-imino-isoindolenine glycol adduct and 12.95 parts of 1 -ethyl-2 (cyanomethyl)-benzimidazole in 120 parts of nitrobenzene are stirred for 3 hours at 1000C.
When the mixture has cooled, it is filtered and the filter residue is washed with methanol, with acetic; acid and again with methanol and is dried.
Yield: 8.9 parts of the compound of the formula 1, where R1=R2= C2H 5, in the form of bright red needles.
Use Examples
a) 0.05% strength, transparent coloration of polystyrene.
0.05 part of the dye from Example 1 is mixed with 100 parts of milled polystyrene polymer in a drum mixer. The mixture is fused, and homogenized, in an extruder at a barrel temperature of from 200 to 25O0C. The colored material is granulated by face-cutting. Moldings are then produced from the granules on an injection molding machine at from 200 to 3000C.
The moldings are bright red, fluoresce in a similar hue, and exhibit excellent lightfastness.
No differences in hue are observed at processing temperatures from 200 to 3000C.
b) 0.05% strength transparent coloration of a styrene-budadiene copolymer.
The procedure described for a) is followed, but instead of polystyrene a styrene-butadiene copolymer is used.
The bright red injection moldings obtained are lightfast. The dye is stable at processing temperatures of up to 3000.
c) 0.05% strength transparent coloration of a styrene/acrylonitrile/acrylate copolymer.
The procedure described for a) is followed, but using a styrene/acrylonitrile/acrylate copolymer.
Bright red colorations are obtained. The dye is stable in this copolymer at up to 3000C.
d) 0.05% strength transparent coloration of polymethyl methacrylate.
The procedure described for a) is followed, but using a polymethyl methacrylate as the polymer.
Fluorescent lightfast bright red colorations are obtained. The dye is stable in this medium at up to 28O0C.
e) 0.05% strength transparent coloration of a styrene/acrylonitrile copolymer.
The procedure described for a) is followed, but using a copolymer comprising 35% of acrylonitrile units and 65% of styrene units. Fluorescent bright red injection moldings are obtained. The dye is stable in the copolymer at up to 3O00C.
ft 0.05% strength transparent coloration of a styrene/acrylonitrile/butadiene copolymer.
The- procedure described for a) is followed, but using a graft polymer based on styrene, acrylonitrile and rubber. Bright red injection moldings are obtained. The dye is stable in the copolymer at up to 3000C.
Claims (6)
1. An isoindoline derivative of the formula
where R1 and R2 are methyl or ethyl and are identical or different.
2. The isoindoline derivative claimed in claim 1 in which R' and R2 are both methyl.
3. An isoindoline derivative claimed in claim 1 when prepared by condensing a 1,3-disubstituted isoindolenine with 2 molar proportions of the appropriate 1-alkyl-2- cyanomethylbenzimidazole(s) in an organic medium at from 80 to 1200C.
4. A process for melt-coloring polystyrene, polyacrylonitrile, polyacrylate, polymethacrylate, polycarbonate, styrene/acrylonitrile/acrylate copolymers, styrene/butadiene/acrylonitrile copolymers, styrene/acrylonitrile copolymers and styrene/butadiene copolymers, wherein a compound as claimed in any of claims 1 to 3 is used as the dye.
5. Synthetic thermoplastics material colored with a compound as claimed in any of claims 1 to
3.
6. A process as claimed in claim 4 carried out
substantially as described in any of the foregoing
Use Examples a) to f).
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19782830501 DE2830501A1 (en) | 1978-07-12 | 1978-07-12 | ISOINDOL DERIVATIVES AND THEIR USE |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB2031006A true GB2031006A (en) | 1980-04-16 |
| GB2031006B GB2031006B (en) | 1982-10-27 |
Family
ID=6044108
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB7928628A Expired GB2031006B (en) | 1978-07-12 | 1979-08-16 | Isoindoline derivatives and their use |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE2830501A1 (en) |
| GB (1) | GB2031006B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3110953A1 (en) * | 1981-03-20 | 1982-09-30 | Basf Ag, 6700 Ludwigshafen | ELECTROPHOTOGRAPHIC RECORDING MATERIAL |
-
1978
- 1978-07-12 DE DE19782830501 patent/DE2830501A1/en not_active Withdrawn
-
1979
- 1979-08-16 GB GB7928628A patent/GB2031006B/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB2031006B (en) | 1982-10-27 |
| DE2830501A1 (en) | 1980-02-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |