CA1115712A - (cyclo)alkylene diammonium salts of tetrahalophthalate half-esters - Google Patents
(cyclo)alkylene diammonium salts of tetrahalophthalate half-estersInfo
- Publication number
- CA1115712A CA1115712A CA294,951A CA294951A CA1115712A CA 1115712 A CA1115712 A CA 1115712A CA 294951 A CA294951 A CA 294951A CA 1115712 A CA1115712 A CA 1115712A
- Authority
- CA
- Canada
- Prior art keywords
- bis
- alkylene
- tetrahalophthalate
- carbon atoms
- cyclo
- 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
- 125000002947 alkylene group Chemical group 0.000 title claims abstract description 10
- 150000003839 salts Chemical class 0.000 title description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 14
- 238000009835 boiling Methods 0.000 claims abstract description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 9
- 125000002993 cycloalkylene group Chemical group 0.000 claims abstract description 8
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 125000005843 halogen group Chemical group 0.000 claims abstract description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 4
- 238000010438 heat treatment Methods 0.000 claims abstract description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- -1 cycloalkyI Chemical group 0.000 claims description 6
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical group NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 5
- QHWKHLYUUZGSCW-UHFFFAOYSA-N Tetrabromophthalic anhydride Chemical group BrC1=C(Br)C(Br)=C2C(=O)OC(=O)C2=C1Br QHWKHLYUUZGSCW-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 2
- 229910052794 bromium Inorganic materials 0.000 claims 2
- 125000001246 bromo group Chemical group Br* 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
- 239000003063 flame retardant Substances 0.000 abstract description 7
- 239000000543 intermediate Substances 0.000 abstract description 4
- 238000002360 preparation method Methods 0.000 abstract description 2
- 150000003949 imides Chemical class 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 150000008064 anhydrides Chemical class 0.000 description 5
- 150000004985 diamines Chemical class 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 2
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- KMBSSXSNDSJXCG-UHFFFAOYSA-N 1-[2-(2-hydroxyundecylamino)ethylamino]undecan-2-ol Chemical group CCCCCCCCCC(O)CNCCNCC(O)CCCCCCCCC KMBSSXSNDSJXCG-UHFFFAOYSA-N 0.000 description 1
- OIGFNQRFPUUACU-UHFFFAOYSA-N 3-bromophthalic acid Chemical compound OC(=O)C1=CC=CC(Br)=C1C(O)=O OIGFNQRFPUUACU-UHFFFAOYSA-N 0.000 description 1
- QRFTXHFUNIFHST-UHFFFAOYSA-N 4,5,6,7-tetrabromoisoindole-1,3-dione Chemical compound BrC1=C(Br)C(Br)=C2C(=O)NC(=O)C2=C1Br QRFTXHFUNIFHST-UHFFFAOYSA-N 0.000 description 1
- DZIHTWJGPDVSGE-UHFFFAOYSA-N 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1CC1CCC(N)CC1 DZIHTWJGPDVSGE-UHFFFAOYSA-N 0.000 description 1
- 101150009724 CYBA gene Proteins 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical class CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- BLEOWQIGEPJXHW-UHFFFAOYSA-N NCCCCCCN.COC(=O)C1=C(Br)C(Br)=C(Br)C(Br)=C1C(=O)OC Chemical compound NCCCCCCN.COC(=O)C1=C(Br)C(Br)=C(Br)C(Br)=C1C(=O)OC BLEOWQIGEPJXHW-UHFFFAOYSA-N 0.000 description 1
- ZLJNHKUVTZKFRC-UHFFFAOYSA-N NCCN.COC(=O)C1=C(Br)C(Br)=C(Br)C(Br)=C1C(=O)OC Chemical compound NCCN.COC(=O)C1=C(Br)C(Br)=C(Br)C(Br)=C1C(=O)OC ZLJNHKUVTZKFRC-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000005700 Putrescine Substances 0.000 description 1
- XMUZQOKACOLCSS-UHFFFAOYSA-N [2-(hydroxymethyl)phenyl]methanol Chemical compound OCC1=CC=CC=C1CO XMUZQOKACOLCSS-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- SSJXIUAHEKJCMH-UHFFFAOYSA-N cyclohexane-1,2-diamine Chemical compound NC1CCCCC1N SSJXIUAHEKJCMH-UHFFFAOYSA-N 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical class CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- AUHHYELHRWCWEZ-UHFFFAOYSA-N tetrachlorophthalic anhydride Chemical compound ClC1=C(Cl)C(Cl)=C2C(=O)OC(=O)C2=C1Cl AUHHYELHRWCWEZ-UHFFFAOYSA-N 0.000 description 1
- 238000002411 thermogravimetry Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/759,949 US4140862A (en) | 1977-01-17 | 1977-01-17 | Salts of diamines and tetrahalophthalates |
| US759,949 | 1977-01-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1115712A true CA1115712A (en) | 1982-01-05 |
Family
ID=25057562
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA294,951A Expired CA1115712A (en) | 1977-01-17 | 1978-01-13 | (cyclo)alkylene diammonium salts of tetrahalophthalate half-esters |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4140862A (en, 2012) |
| BE (1) | BE862992A (en, 2012) |
| CA (1) | CA1115712A (en, 2012) |
| DE (1) | DE2802292C3 (en, 2012) |
| FR (1) | FR2377371A1 (en, 2012) |
| GB (1) | GB1565791A (en, 2012) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4666958A (en) * | 1982-01-07 | 1987-05-19 | Ppg Industries, Inc. | Polymeric compositions containing polyhalophthalimidoalkyl-functional carbonates |
| US4515964A (en) * | 1982-01-07 | 1985-05-07 | Ppg Industries, Inc. | Polyhalophthalimidoalkyl-functional carbonates |
| US4414396A (en) * | 1982-01-07 | 1983-11-08 | Ppg Industries, Inc. | Polyhalophthalimidoalkyl-functional carbonates and haloformates |
| US4467062A (en) * | 1983-08-18 | 1984-08-21 | Ethyl Corporation | Flame retarded polyethylene terephthalate blends |
| CN1041718C (zh) * | 1994-11-14 | 1999-01-20 | 山东建筑材料工业学院 | 白色n,n'－烷撑双(四溴邻苯二甲酰胺)系列化合物的制备方法 |
| US6180560B1 (en) | 1997-08-14 | 2001-01-30 | Ricoh Company, Ltd. | Thermosensitive recording material and color developer compound therefor |
| FR2767283B1 (fr) * | 1997-08-14 | 2001-11-23 | Ricoh Kk | Materiau d'enregistrement thermosensible, developpateur de couleur pour celui-ci, et procede de preparation de ce developpateur de couleur |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS536857B2 (en, 2012) * | 1972-08-16 | 1978-03-11 | ||
| US4092345A (en) * | 1976-07-30 | 1978-05-30 | Cities Service Company | (Cyclo)alkylenediammonium-bis-tetrahalophthalates |
-
1977
- 1977-01-17 US US05/759,949 patent/US4140862A/en not_active Expired - Lifetime
-
1978
- 1978-01-13 CA CA294,951A patent/CA1115712A/en not_active Expired
- 1978-01-17 GB GB1778/78A patent/GB1565791A/en not_active Expired
- 1978-01-17 FR FR7801271A patent/FR2377371A1/fr active Granted
- 1978-01-17 BE BE184390A patent/BE862992A/xx not_active IP Right Cessation
- 1978-01-17 DE DE2802292A patent/DE2802292C3/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2802292C3 (de) | 1981-02-05 |
| GB1565791A (en) | 1980-04-23 |
| FR2377371A1 (fr) | 1978-08-11 |
| FR2377371B1 (en, 2012) | 1981-08-07 |
| US4140862A (en) | 1979-02-20 |
| DE2802292A1 (de) | 1978-07-20 |
| DE2802292B2 (de) | 1980-06-04 |
| BE862992A (fr) | 1978-05-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |