DD232286A5 - Verfahren zur herstellung von nylon-block-copolymeren - Google Patents

Verfahren zur herstellung von nylon-block-copolymeren Download PDF

Info

Publication number: DD232286A5
Authority: DD; German Democratic Republic
Prior art keywords: magnesium; solution; caprolactam; acid halide; functional
Prior art date: 1983-12-12

Application number

DD84270604A

Other languages

German (de)

English (en)

Inventor

Albert Y Garner

James D Gabbert

Ross M Hedrick

Original Assignee

Monsanto Company,Us

Priority date (The priority date 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 date listed.)

1983-12-12

Filing date

1984-12-11

Publication date

1986-01-22

1984-12-11 Application filed by Monsanto Company,Us filed Critical Monsanto Company,Us

1986-01-22 Publication of DD232286A5 publication Critical patent/DD232286A5/de

Links

229920001400 block copolymer Polymers 0.000 title claims abstract description 24
229920001778 nylon Polymers 0.000 title claims abstract description 24
239000004677 Nylon Substances 0.000 title claims abstract description 23
238000004519 manufacturing process Methods 0.000 title description 4
JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 claims abstract description 78
239000002253 acid Substances 0.000 claims abstract description 57
-1 acyl lactam Chemical class 0.000 claims abstract description 55
239000011777 magnesium Substances 0.000 claims abstract description 53
229910052749 magnesium Inorganic materials 0.000 claims abstract description 53
150000004820 halides Chemical class 0.000 claims abstract description 52
239000000463 material Substances 0.000 claims abstract description 45
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims abstract description 41
238000000034 method Methods 0.000 claims abstract description 36
239000000203 mixture Substances 0.000 claims abstract description 21
150000003951 lactams Chemical class 0.000 claims abstract description 11
238000006243 chemical reaction Methods 0.000 claims description 18
229930195733 hydrocarbon Natural products 0.000 claims description 17
238000002360 preparation method Methods 0.000 claims description 17
229920000570 polyether Polymers 0.000 claims description 16
150000002430 hydrocarbons Chemical class 0.000 claims description 15
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 14
239000004721 Polyphenylene oxide Substances 0.000 claims description 13
229920000728 polyester Polymers 0.000 claims description 13
239000004215 Carbon black (E152) Substances 0.000 claims description 12
AWPZMYBGHAYSFU-UHFFFAOYSA-N magnesium;pyrrolidin-2-one Chemical compound [Mg].O=C1CCCN1.O=C1CCCN1 AWPZMYBGHAYSFU-UHFFFAOYSA-N 0.000 claims description 11
229920001296 polysiloxane Polymers 0.000 claims description 7
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 6
125000005843 halogen group Chemical group 0.000 claims description 5
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 4
239000005062 Polybutadiene Substances 0.000 claims description 4
229920002857 polybutadiene Polymers 0.000 claims description 4
239000011541 reaction mixture Substances 0.000 claims description 4
JHWNWJKBPDFINM-UHFFFAOYSA-N Laurolactam Chemical compound O=C1CCCCCCCCCCCN1 JHWNWJKBPDFINM-UHFFFAOYSA-N 0.000 claims description 3
229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 3
229920001451 polypropylene glycol Polymers 0.000 claims description 3
125000002102 aryl alkyloxo group Chemical group 0.000 claims description 2
125000003118 aryl group Chemical group 0.000 claims description 2
125000004104 aryloxy group Chemical group 0.000 claims description 2
239000000460 chlorine Substances 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 2
150000001732 carboxylic acid derivatives Chemical class 0.000 claims 2
239000000178 monomer Substances 0.000 claims 2
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
229910000147 aluminium phosphate Inorganic materials 0.000 claims 1
125000001309 chloro group Chemical group Cl* 0.000 claims 1
125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 abstract description 8
229910001629 magnesium chloride Inorganic materials 0.000 abstract description 4
125000002252 acyl group Chemical group 0.000 abstract description 2
239000000243 solution Substances 0.000 description 40
238000006116 polymerization reaction Methods 0.000 description 16
229920005862 polyol Polymers 0.000 description 11
229920000642 polymer Polymers 0.000 description 10
150000003077 polyols Chemical class 0.000 description 10
239000003054 catalyst Substances 0.000 description 9
DVPHDWQFZRBFND-DMHDVGBCSA-N 1-o-[2-[(3ar,5r,6s,6ar)-2,2-dimethyl-6-prop-2-enoyloxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-[4-[(2s,3r)-1-butan-2-ylsulfanyl-2-(2-chlorophenyl)-4-oxoazetidin-3-yl]oxy-4-oxobutanoyl]oxyethyl] 4-o-[(2s,3r)-1-butan-2-ylsulfanyl-2-(2-chloropheny Chemical group C1([C@H]2[C@H](C(N2SC(C)CC)=O)OC(=O)CCC(=O)OC(COC(=O)CCC(=O)O[C@@H]2[C@@H](N(C2=O)SC(C)CC)C=2C(=CC=CC=2)Cl)[C@@H]2[C@@H]([C@H]3OC(C)(C)O[C@H]3O2)OC(=O)C=C)=CC=CC=C1Cl DVPHDWQFZRBFND-DMHDVGBCSA-N 0.000 description 7
229920001577 copolymer Polymers 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
239000003999 initiator Substances 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
150000002009 diols Chemical class 0.000 description 5
LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
229920002292 Nylon 6 Polymers 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
238000005266 casting Methods 0.000 description 3
238000011065 in-situ storage Methods 0.000 description 3
239000003921 oil Substances 0.000 description 3
239000004033 plastic Substances 0.000 description 3
229920003023 plastic Polymers 0.000 description 3
229920001281 polyalkylene Polymers 0.000 description 3
239000002516 radical scavenger Substances 0.000 description 3
238000011084 recovery Methods 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
239000004952 Polyamide Substances 0.000 description 2
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 2
OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 2
125000000753 cycloalkyl group Chemical group 0.000 description 2
229920001971 elastomer Polymers 0.000 description 2
239000000806 elastomer Substances 0.000 description 2
238000011049 filling Methods 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000011521 glass Substances 0.000 description 2
239000012535 impurity Substances 0.000 description 2
238000012693 lactam polymerization Methods 0.000 description 2
239000008204 material by function Substances 0.000 description 2
238000002156 mixing Methods 0.000 description 2
239000012299 nitrogen atmosphere Substances 0.000 description 2
229920002647 polyamide Polymers 0.000 description 2
229920000098 polyolefin Polymers 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
230000002028 premature Effects 0.000 description 2
238000010107 reaction injection moulding Methods 0.000 description 2
238000007711 solidification Methods 0.000 description 2
230000008023 solidification Effects 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
230000003068 static effect Effects 0.000 description 2
238000003756 stirring Methods 0.000 description 2
238000005292 vacuum distillation Methods 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-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
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
229920000393 Nylon 6/6T Polymers 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
239000004743 Polypropylene Substances 0.000 description 1
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
239000004809 Teflon Substances 0.000 description 1
229920006362 Teflon® Polymers 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
ABMPLDRTDDMKHF-UHFFFAOYSA-N azepan-2-one;magnesium Chemical compound [Mg].O=C1CCCCCN1.O=C1CCCCCN1 ABMPLDRTDDMKHF-UHFFFAOYSA-N 0.000 description 1
238000009835 boiling Methods 0.000 description 1
235000011089 carbon dioxide Nutrition 0.000 description 1
RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 1
125000002843 carboxylic acid group Chemical group 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000007872 degassing Methods 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
239000004205 dimethyl polysiloxane Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
125000001033 ether group Chemical group 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000010419 fine particle Substances 0.000 description 1
125000001475 halogen functional group Chemical group 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
238000010952 in-situ formation Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
230000000977 initiatory effect Effects 0.000 description 1
229910001507 metal halide Inorganic materials 0.000 description 1
150000005309 metal halides Chemical class 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
229920000233 poly(alkylene oxides) Polymers 0.000 description 1
229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
229920001155 polypropylene Polymers 0.000 description 1
239000000047 product Substances 0.000 description 1
238000005086 pumping Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229910052710 silicon Inorganic materials 0.000 description 1
239000010703 silicon Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000013638 trimer Substances 0.000 description 1

Landscapes

Polyamides (AREA)

DD84270604A 1983-12-12 1984-12-11 Verfahren zur herstellung von nylon-block-copolymeren DD232286A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US56064483A	1983-12-12	1983-12-12

Publications (1)

Publication Number	Publication Date
DD232286A5 true DD232286A5 (de)	1986-01-22

Family

ID=24238690

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
DD84270604A DD232286A5 (de)	1983-12-12	1984-12-11	Verfahren zur herstellung von nylon-block-copolymeren
DD28260085A DD238056A5 (de)	1983-12-12	1985-11-07	Zusammensetzung zur verwendung bei der schnellpolymerisation von epsilon-caprolactamzur bildung von nylon-6-blockcopolymeren

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
DD28260085A DD238056A5 (de)	1983-12-12	1985-11-07	Zusammensetzung zur verwendung bei der schnellpolymerisation von epsilon-caprolactamzur bildung von nylon-6-blockcopolymeren

Country Status (3)

Country	Link
JP (1)	JPS60168723A (ja)
DD (2)	DD232286A5 (ja)
ZA (1)	ZA849640B (ja)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4596865A (en) *	1984-12-17	1986-06-24	Monsanto Company	Promotion of ε-caprolactam block copolymerization
KR910003646B1 (ko) *	1986-04-10	1991-06-08	몬산토 캄파니	폴리아실락탐

1984
- 1984-12-11 JP JP26011784A patent/JPS60168723A/ja active Pending
- 1984-12-11 ZA ZA849640A patent/ZA849640B/xx unknown
- 1984-12-11 DD DD84270604A patent/DD232286A5/de unknown
1985
- 1985-11-07 DD DD28260085A patent/DD238056A5/de unknown

Also Published As

Publication number	Publication date
DD238056A5 (de)	1986-08-06
ZA849640B (en)	1985-07-31
JPS60168723A (ja)	1985-09-02

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