CN1752150A - Preparation process of azo reactive dye - Google Patents
Preparation process of azo reactive dye Download PDFInfo
- Publication number
- CN1752150A CN1752150A CN 200510095158 CN200510095158A CN1752150A CN 1752150 A CN1752150 A CN 1752150A CN 200510095158 CN200510095158 CN 200510095158 CN 200510095158 A CN200510095158 A CN 200510095158A CN 1752150 A CN1752150 A CN 1752150A
- Authority
- CN
- China
- Prior art keywords
- suspension
- diazonium salt
- weight part
- add
- acid
- 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
- 238000002360 preparation method Methods 0.000 title claims description 9
- 239000000985 reactive dye Substances 0.000 title abstract 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 30
- 239000012954 diazonium Substances 0.000 claims abstract description 23
- 150000001989 diazonium salts Chemical class 0.000 claims abstract description 23
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims abstract description 22
- 239000000725 suspension Substances 0.000 claims abstract description 22
- 239000002253 acid Substances 0.000 claims abstract description 21
- 238000006243 chemical reaction Methods 0.000 claims abstract description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 12
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims abstract description 12
- 229910052708 sodium Inorganic materials 0.000 claims abstract description 11
- 239000011734 sodium Substances 0.000 claims abstract description 11
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims abstract description 10
- 238000003756 stirring Methods 0.000 claims abstract description 9
- 229940051841 polyoxyethylene ether Drugs 0.000 claims abstract description 7
- 229920000056 polyoxyethylene ether Polymers 0.000 claims abstract description 7
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims abstract description 6
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000002156 mixing Methods 0.000 claims abstract description 6
- 235000010288 sodium nitrite Nutrition 0.000 claims abstract description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000000975 dye Substances 0.000 claims description 12
- 238000005516 engineering process Methods 0.000 claims description 11
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 6
- 150000008107 benzenesulfonic acids Chemical class 0.000 claims description 4
- 230000008878 coupling Effects 0.000 abstract description 10
- 238000010168 coupling process Methods 0.000 abstract description 10
- 238000005859 coupling reaction Methods 0.000 abstract description 10
- 150000001875 compounds Chemical class 0.000 abstract description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 abstract 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- APRRQJCCBSJQOQ-UHFFFAOYSA-N 4-amino-5-hydroxynaphthalene-2,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(O)=C2C(N)=CC(S(O)(=O)=O)=CC2=C1 APRRQJCCBSJQOQ-UHFFFAOYSA-N 0.000 description 5
- KXXFHLLUPUAVRY-UHFFFAOYSA-J [Na+].[Na+].[Na+].[Cu++].[O-]C(=O)C1=CC=C(C=C1N=N[C-](N=NC1=C([O-])C(NC2=NC(F)=NC(NCCOCCS(=O)(=O)C=C)=N2)=CC(=C1)S([O-])(=O)=O)C1=CC=CC=C1)S([O-])(=O)=O Chemical compound [Na+].[Na+].[Na+].[Cu++].[O-]C(=O)C1=CC=C(C=C1N=N[C-](N=NC1=C([O-])C(NC2=NC(F)=NC(NCCOCCS(=O)(=O)C=C)=N2)=CC(=C1)S([O-])(=O)=O)C1=CC=CC=C1)S([O-])(=O)=O KXXFHLLUPUAVRY-UHFFFAOYSA-J 0.000 description 5
- 239000013543 active substance Substances 0.000 description 2
- 239000012752 auxiliary agent Substances 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- DPDMMXDBJGCCQC-UHFFFAOYSA-N [Na].[Cl] Chemical compound [Na].[Cl] DPDMMXDBJGCCQC-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Landscapes
- Coloring (AREA)
Abstract
A process for preparing azo reactive dye includes mixing cyanuric chloride with water to form suspension; adding the 2.4-diaminobenzene sodium sulfonate solution into the suspension, adding the sodium hydroxide solution into the suspension, and keeping the reaction until the weight ratio content of the unreacted 2.4-diaminobenzene sodium sulfonate is less than 1%; adding 3- (beta-hydroxyvinylsulfone sulfate) aniline, adding sodium hydroxide solution, keeping the weight ratio of the unreacted 3- (beta-hydroxyvinylsulfone sulfate) aniline to be less than 0.8%, and adding hydrochloric acid and sodium nitrite for reaction to form diazonium salt; adding fatty amine polyoxyethylene ether and thiourea into the diazonium salt, fully stirring, adding 1-amino-8-naphthol-3.6-disulfonic acid, and reacting until the diazonium salt disappears to obtain the final point. The yield of the acid coupling compound is about 10 percent higher than that of the prior art, and the purity of the acid coupling compound is obviously improved.
Description
Technical field
The present invention relates to a kind of preparation technology of dyestuff.
Background technology
The present invention relates to a kind of azo active dyestuff, the structural formula of this compound is:
In the prior art, the technology for preparing this compound is: cyanuric chloride, water, ice, adding thorough mixing under the situation of wetting agent, adding 2.4-diamino benzene sulfonic acid sodium, be reacted to terminal point after, add 3-(β-hydroxyalkyl vinyl sulfone sulfate) aniline again, keeping temperature is that 25-40 ℃, pH value are 5-5.5, be reacted to terminal point after, cooling on the rocks, the hydrochloric acid and the sodium nitrite solution that add specified amount carry out doazo reaction, generate diazonium salt.
In diazonium salt, add under urea and the Dispersant MF condition, after stirring, add 1-amino-8-naphthol-3.6-disulfonic acid (being also referred to as H acid) solution and carry out acid condensation, keeping temperature is 0-30 ℃, pH value is 0-3, is reacted to terminal point, thereby obtains the compound of said structure formula.
Reactive dyestuffs require to have enough direct colourabilitys, and simultaneously non-solid part is easy to washing, and they also should have good tint permanence and high reactivity, and above-mentioned technology synthetic dyestuff easily produces a large amount of isomer, and its structural formula is:
Therefore can not reach the requirement of above-mentioned characteristic.
Summary of the invention
The object of the invention provides a kind of preparation technology of azo active dyestuff, reduces the formation of isomer after can making this dyestuff synthetic as far as possible, and the reactive dyestuffs that make have the stability of high color fixation fastness and high fiber and dyestuff connection.
Technical scheme of the present invention is: a kind of preparation technology of azo active dyestuff, and it comprises following operation:
(1), weight part 18.4-19.8 part cyanuric chloride, 50 parts of water thorough mixing of weight part form suspension;
(2), 21 parts of 2.4-diamino benzene sulfonic acids of weight part sodium solution is added in the suspension, in suspension, add sodium hydroxide solution again, the pH value of suspension is remained between the 2.5-3, keep reaction to unreacted 2.4-diamino benzene sulfonic acid sodium weight ratio content less than 1%;
(3), add weight part 28-30 part 3-(β-hydroxyalkyl vinyl sulfone sulfate) aniline again, be warmed up to 25-40 ℃, adding sodium hydroxide solution accent pH value is 5-5.5, keep reaction to unreacted 3-(β-hydroxyalkyl vinyl sulfone sulfate) aniline weight ratio content less than 0.8%, be cooled to 0～5 ℃, add 25-28 part hydrochloric acid and 6.21-6.9 part Sodium Nitrite reaction back and form diazonium salt;
(4), the aliphatic amine polyoxyethylene ether and the weight part 0.1-5 part thiocarbamide that in diazonium salt, add weight part 0.3-5 part, fully stir the back and add weight part 30-34.1 part 1-amino-8-naphthol-3-6-disulfonic acid, maintaining the temperature at 0-20 ℃, pH value is 0-3, and reacting disappears to diazonium salt is terminal point.
In step (1), the temperature of described suspension remains on 0～2 ℃.
The present invention compared with prior art, has following advantage: the present invention relates to aliphatic amine polyoxyethylene ether and thiocarbamide promotor as acid coupling, in the presence of above material, acid coupling is more prone to reaction, thereby has prepared highly purified desired compound.Process recovery ratio of the present invention improves about 10% apparently higher than original technology, can not produce isomer in a large number, makes in the dyestuff preparation and obtains high-purity acid coupling thing.
Embodiment
A kind of preparation technology of azo active dyestuff, it comprises following operation:
(1), 50 parts of water thorough mixing of weight part 18.4-19.8 part cyanuric chloride, weight part form suspension, the temperature of described suspension remains on 0～2 ℃;
(2), 21 parts of 2.4-diamino benzene sulfonic acids of weight part sodium solution is added in the suspension, in suspension, add sodium hydroxide solution again, the pH value of suspension is remained between the 2.5-3, keep reaction to unreacted 2.4-diamino benzene sulfonic acid sodium weight ratio content less than 1%;
(3), add weight part 28-30 part 3-(β-hydroxyalkyl vinyl sulfone sulfate) aniline again, be warmed up to 25-40 ℃, adding sodium hydroxide solution accent pH value is 5-5.5, keep reaction to unreacted 3-(β-hydroxyalkyl vinyl sulfone sulfate) aniline weight ratio content less than 0.8%, be cooled to 0～5 ℃, add 25-28 part hydrochloric acid and 6.21-6.9 part Sodium Nitrite reaction back and form diazonium salt;
(4), the aliphatic amine polyoxyethylene ether and the weight part 0.1-5 part thiocarbamide that in diazonium salt, add weight part 0.3-5 part, fully stir the back and add weight part 30-34.1 part 1-amino-8-naphthol-3.6-disulfonic acid, maintaining the temperature at 0-20 ℃, pH value is 0-3, and reacting disappears to diazonium salt is terminal point.
With the above-mentioned acid coupling thing that reaches behind the reaction end, add sodium-chlor, and saltout, filter, prepare the even color base of C.I. Reactive Blue 222 acid that the present invention relates to.
Referring to several examples:
(1), weight part 18.4-19.8 part cyanuric chloride, 50 parts of water thorough mixing of weight part form suspension;
(2), 21 parts of 2.4-diamino benzene sulfonic acids of weight part sodium solution is added in the suspension, in suspension, add sodium hydroxide solution again, the pH value of suspension is remained between the 2.5-3, keep reaction to unreacted 2.4-diamino benzene sulfonic acid sodium weight ratio content less than 1%;
(3), add weight part 28-30 part 3-(β-hydroxyalkyl vinyl sulfone sulfate) aniline again, be warmed up to 25-40 ℃, adding sodium hydroxide solution accent pH value is 5-5.5, keep reaction to unreacted 3-(β-hydroxyalkyl vinyl sulfone sulfate) aniline weight ratio content less than 0.8%, be cooled to 0～5 ℃, add 25-28 part hydrochloric acid and 6.21-6.9 part Sodium Nitrite reaction back and form diazonium salt; Below the preceding step of each embodiment all identical with above-mentioned steps, therefore following each embodiment only enumerates a last step.
Embodiment 1:
In 0.1 mole diazonium salt, tensio-active agent 1860 (being aliphatic amine polyoxyethylene ether) and 3.1 parts of thiocarbamides of weight part of adding 1 part of weight part, after stirring, be under the 0-3 ℃ of condition, slowly add 1-amino-8-naphthol-3.6-disulfonic acid (being commonly called as H acid) solution of weight part 30-34.1 part in temperature, maintain the temperature at 0-20 ℃, pH value is 0-3, reacts 8 hours, and diazonium salt disappears, prepare needed C.I. Reactive Blue 222 acid coupling thing, yield is 92%.
Embodiment 2:
In the diazonium salt of 0.1mol, tensio-active agent 1860 (being aliphatic amine polyoxyethylene ether) and 6 parts of thiocarbamides of weight part of adding 2.5 parts of weight parts, after stirring, be under the 0-3 ℃ of condition, slowly add 1-amino-8-naphthol-3.6-disulfonic acid (being commonly called as H acid) solution of weight part 30-34.1 part in temperature, maintain the temperature at 0-20 ℃, pH value is 0-3, reacts 8 hours, and diazonium salt disappears, prepare C.I. Reactive Blue 222 acid coupling thing, yield is 80%.
Comparative example 1:
In the diazonium salt of 0.1mol, auxiliary agent MF and 5 parts of urea of adding 1.5 parts of weight parts, in good stirring and temperature is under the 0-3 ℃ of condition, slowly add 1-amino-8-naphthol-3.6-disulfonic acid (H acid) solution of weight part 30-34.1 part, keeping temperature is 0-20 ℃, and pH value is 0-3, reacted 8 hours, diazonium salt disappears, and prepares C.I. Reactive Blue 222 acid coupling thing, and yield is 80%.
Comparative example 2:
In the diazonium salt of 0.1mol, do not add any auxiliary agent, under good stirring, be under the 0-3 ℃ of condition in temperature, slowly add 1-amino-8-naphthol-3.6-disulfonic acid (H acid) solution of weight part 30-34.1 part, maintain the temperature at 0-20 ℃, pH value is 0-3, reacts 8 hours, and diazonium salt disappears, prepare C.I. Reactive Blue 222 acid coupling thing, yield is 70%.
Claims (2)
1, a kind of preparation technology of azo active dyestuff is characterized in that: it comprises following operation:
(1), weight part 18.4-19.8 part cyanuric chloride, 50 parts of water thorough mixing of weight part form suspension;
(2), 21 parts of 2.4-diamino benzene sulfonic acids of weight part sodium solution is added in the suspension, in suspension, add sodium hydroxide solution again, the pH value of suspension is remained between the 2.5-3, keep reaction to unreacted 2.4-diamino benzene sulfonic acid sodium weight ratio content less than 1%;
(3), add weight part 28-30 part 3-(β-hydroxyalkyl vinyl sulfone sulfate) aniline again, be warmed up to 25-40 ℃, adding sodium hydroxide solution accent pH value is 5-5.5, keep reaction to unreacted 3-(β-hydroxyalkyl vinyl sulfone sulfate) aniline weight ratio content less than 0.8%, be cooled to 0～5 ℃, add 25-28 part hydrochloric acid and 6.21-6.9 part Sodium Nitrite reaction back and form diazonium salt;
(4), the aliphatic amine polyoxyethylene ether and the weight part 0.1-5 part thiocarbamide that in diazonium salt, add weight part 0.3-5 part, fully stir the back and add weight part 30-34.1 part 1-amino-8-naphthol-3.6-disulfonic acid, maintaining the temperature at 0-20 ℃, pH value is 0-3, and reacting disappears to diazonium salt is terminal point.
2, the preparation technology of azo active dyestuff according to claim 1 is characterized in that: in step (1), the temperature of described suspension remains on 0～2 ℃.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2005100951582A CN100349989C (en) | 2005-10-27 | 2005-10-27 | Preparation process of azo reactive dye |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2005100951582A CN100349989C (en) | 2005-10-27 | 2005-10-27 | Preparation process of azo reactive dye |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1752150A true CN1752150A (en) | 2006-03-29 |
| CN100349989C CN100349989C (en) | 2007-11-21 |
Family
ID=36679158
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB2005100951582A Expired - Fee Related CN100349989C (en) | 2005-10-27 | 2005-10-27 | Preparation process of azo reactive dye |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN100349989C (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102311369A (en) * | 2011-09-13 | 2012-01-11 | 吴江桃源染料有限公司 | Preparation method of 1-amino-2-(4-sulfonic acid azobenzene)-8-hydroxy-3,6-disulfonic acid |
| CN104140690A (en) * | 2014-07-29 | 2014-11-12 | 嘉兴瑞奕环保科技有限公司 | Azo pigment acid coupling reaction auxiliary and application thereof |
| CN104327542A (en) * | 2014-10-13 | 2015-02-04 | 天津德凯化工股份有限公司 | Red reactive dye and its preparation method |
| CN115466524A (en) * | 2022-09-02 | 2022-12-13 | 浙江劲光实业股份有限公司 | Synthesis method of reactive dye |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1108348C (en) * | 2000-10-24 | 2003-05-14 | 泰兴市锦鸡染料有限公司 | Reactive azo orange dye and its preparing process |
| CN1261505C (en) * | 2004-08-02 | 2006-06-28 | 吴江桃源染料厂 | Preparation process of azo reactive dye |
-
2005
- 2005-10-27 CN CNB2005100951582A patent/CN100349989C/en not_active Expired - Fee Related
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102311369A (en) * | 2011-09-13 | 2012-01-11 | 吴江桃源染料有限公司 | Preparation method of 1-amino-2-(4-sulfonic acid azobenzene)-8-hydroxy-3,6-disulfonic acid |
| CN104140690A (en) * | 2014-07-29 | 2014-11-12 | 嘉兴瑞奕环保科技有限公司 | Azo pigment acid coupling reaction auxiliary and application thereof |
| CN104140690B (en) * | 2014-07-29 | 2016-06-08 | 嘉兴瑞奕环保科技有限公司 | AZOpigments acid idol reaction promoter and application thereof |
| CN104327542A (en) * | 2014-10-13 | 2015-02-04 | 天津德凯化工股份有限公司 | Red reactive dye and its preparation method |
| CN115466524A (en) * | 2022-09-02 | 2022-12-13 | 浙江劲光实业股份有限公司 | Synthesis method of reactive dye |
Also Published As
| Publication number | Publication date |
|---|---|
| CN100349989C (en) | 2007-11-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN100349989C (en) | Preparation process of azo reactive dye | |
| US8088182B2 (en) | Azo dyes, a process for the preparation thereof and the use thereof | |
| KR100270403B1 (en) | Reactive red dyes containing monochlorotriazine and acetoxyethyl sulfone groups | |
| CN102337045A (en) | Blue active dye mixture and preparation and application thereof | |
| CN1294212C (en) | Composition of high washing fastness reactive black compound dyestuff | |
| CN101037404A (en) | Preparation method of para-(beta-Ethyl Sulfonyl Sulfate) aniline sulfonic acid | |
| CN1261505C (en) | Preparation process of azo reactive dye | |
| JP2002507654A (en) | Black reactive dye composition for cellulose fiber | |
| CN1869004A (en) | Monoazo compound, preparation method and application thereof | |
| DE60121363T2 (en) | DISORZOES AND THEIR COPPER COMPLEXES FOR PAPERING | |
| KR100633672B1 (en) | Processes for producing 4,6-bis(substituted)phenylazoresorcinols | |
| CN101942215A (en) | Orange reactive dye for wool and preparation method thereof | |
| KR100313583B1 (en) | Azocoupling 2,4-disubstituted phenols with 2-nitroaniline | |
| KR100270401B1 (en) | Reactive black dyes containing acetoxyethylsulfone moiety | |
| US6992179B1 (en) | Reactive orange dyes containing vinyl sulfones | |
| KR100411189B1 (en) | Disperse-reactive dyes containing vinyl sulfone moiety | |
| KR100270404B1 (en) | Reacrive blue dyes containing monochlorotriazine and acetoxyethyl sulfone groups | |
| KR0141020B1 (en) | Reactive monoazodye and method for their production | |
| KR100288120B1 (en) | Reactive blue dyes containing monochlorotriazine and acetoxyethyl sulfone groups | |
| CN1187412C (en) | Double active group orange dye and its preparing method | |
| CN111517963A (en) | Preparation method of environment-friendly 2, 6-dichloro-4-nitroaniline | |
| KR100830421B1 (en) | Reactive dyes for polyamide fiber and its manufacturing method | |
| JP4482671B2 (en) | Pyridone azo dye | |
| CN1786078A (en) | Preparation process of direct blending purple dye | |
| JP2999920B2 (en) | Process for producing isonitrosoacetanilides |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| CF01 | Termination of patent right due to non-payment of annual fee | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20071121 Termination date: 20191027 |