CS232759B1 - Method of polymer preparation with carboxyl end groups - Google Patents

Method of polymer preparation with carboxyl end groups Download PDF

Info

Publication number: CS232759B1
Authority: CS; Czechoslovakia
Prior art keywords: anhydride; polymers; living; lithium; molar ratio
Prior art date: 1981-05-07

Application number

CS324782A

Other languages

Czech (cs)

English (en)

Inventor

Elisabeth Antonova

Volker Griehl

Dieter Stubenrauch

Original Assignee

Elisabeth Antonova

Volker Griehl

Dieter Stubenrauch

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.)

1981-05-07

Filing date

1982-05-05

Publication date

1985-02-14

1982-05-05 Application filed by Elisabeth Antonova, Volker Griehl, Dieter Stubenrauch filed Critical Elisabeth Antonova

1985-02-14 Publication of CS232759B1 publication Critical patent/CS232759B1/cs

Links

229920000642 polymer Polymers 0.000 title claims description 41
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 title description 11
238000000034 method Methods 0.000 title description 6
238000002360 preparation method Methods 0.000 title description 4
238000006243 chemical reaction Methods 0.000 claims description 11
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical group [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 10
150000008064 anhydrides Chemical group 0.000 claims description 10
FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 10
229910052700 potassium Inorganic materials 0.000 claims description 9
LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims description 8
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 8
229910052744 lithium Inorganic materials 0.000 claims description 8
239000011591 potassium Substances 0.000 claims description 8
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 7
JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims description 7
150000004703 alkoxides Chemical class 0.000 claims description 6
150000001993 dienes Chemical class 0.000 claims description 6
-1 potassium alkoxide Chemical class 0.000 claims description 6
150000001875 compounds Chemical class 0.000 claims description 4
150000003972 cyclic carboxylic anhydrides Chemical class 0.000 claims description 4
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 description 3
229910052708 sodium Inorganic materials 0.000 claims description 3
239000011734 sodium Substances 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 2
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
239000003999 initiator Substances 0.000 description 8
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
239000001569 carbon dioxide Substances 0.000 description 4
229910002092 carbon dioxide Inorganic materials 0.000 description 4
KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
239000005062 Polybutadiene Substances 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
229920002857 polybutadiene Polymers 0.000 description 3
RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
238000005859 coupling reaction Methods 0.000 description 2
SMBQBQBNOXIFSF-UHFFFAOYSA-N dilithium Chemical compound [Li][Li] SMBQBQBNOXIFSF-UHFFFAOYSA-N 0.000 description 2
125000000524 functional group Chemical group 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
238000010539 anionic addition polymerization reaction Methods 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
230000021523 carboxylation Effects 0.000 description 1
238000006473 carboxylation reaction Methods 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
230000008878 coupling Effects 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
238000001212 derivatisation Methods 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000009472 formulation Methods 0.000 description 1
238000010528 free radical solution polymerization reaction Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
238000005304 joining Methods 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
150000002642 lithium compounds Chemical class 0.000 description 1
WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 1
KKHUSADXXDNRPW-UHFFFAOYSA-N malonic anhydride Chemical compound O=C1CC(=O)O1 KKHUSADXXDNRPW-UHFFFAOYSA-N 0.000 description 1
239000000203 mixture Substances 0.000 description 1
239000000178 monomer Substances 0.000 description 1
239000012454 non-polar solvent Substances 0.000 description 1
238000006384 oligomerization reaction Methods 0.000 description 1
150000002900 organolithium compounds Chemical class 0.000 description 1
125000001979 organolithium group Chemical group 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
239000000047 product Substances 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
150000003509 tertiary alcohols Chemical class 0.000 description 1
238000004448 titration Methods 0.000 description 1

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Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

CS324782A 1981-05-07 1982-05-05 Method of polymer preparation with carboxyl end groups CS232759B1 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DD22978581A DD158782A1 (de)	1981-05-07	1981-05-07	Verfahren zur herstellung von polymeren mit carboxylendgruppen

Publications (1)

Publication Number	Publication Date
CS232759B1 true CS232759B1 (en)	1985-02-14

Family

ID=5530785

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS324782A CS232759B1 (en)	1981-05-07	1982-05-05	Method of polymer preparation with carboxyl end groups

Country Status (2)

Country	Link
CS (1)	CS232759B1 (de)
DD (1)	DD158782A1 (de)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6451935B1 (en) *	2000-05-10	2002-09-17	Bridgestone Corporation	Highly functionalized polymers and a process for making the same

1981
- 1981-05-07 DD DD22978581A patent/DD158782A1/de unknown
1982
- 1982-05-05 CS CS324782A patent/CS232759B1/cs unknown

Also Published As

Publication number	Publication date
DD158782A1 (de)	1983-02-02

Publication	Publication Date	Title
Price et al.	1956	The Polymerization of l-Propylene Oxide1
US4518753A (en)	1985-05-21	Anionic polymerization of conjugated dienes in the presence of hindered triaryl boron or aluminum derivatives
US3668279A (en)	1972-06-06	Process for coupling living lithiopolymers
EP3313927B1 (de)	2021-12-15	Dilithium-initiatoren
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JP2619930B2 (ja)	1997-06-11	二官能性アルカリ金属化合物、その製法及び該化合物から成る重合開始剤
US4525549A (en)	1985-06-25	Process for preparing conjugate diolefins, and means suitable for this purpose
JP2004508434A (ja)	2004-03-18	ジリチウム化開始剤の調製方法およびアニオン重合方法
CS232759B1 (en)	1985-02-14	Method of polymer preparation with carboxyl end groups
US3862251A (en)	1975-01-21	Organo-dilithium initiator for anionic polymerization, a novel polyisoprene, and processes for production thereof
US4075253A (en)	1978-02-21	Organolithium polymerization initiators and their preparations
US3872068A (en)	1975-03-18	Process for preparing block copolymer resin
US3975339A (en)	1976-08-17	Manufacture of polymers of net-shaped structure
JPH0363963B2 (de)	1991-10-03
US4918145A (en)	1990-04-17	Process for producing a block copolymer resin and product thereof
JP4212064B2 (ja)	2009-01-21	疎水性親水性ａｂ型ブロックコポリマーの製造方法
GB2124228A (en)	1984-02-15	Organo-lithium polymerization initiator
US3951931A (en)	1976-04-20	Production of polymeric compounds having functional end groups
NL194674C (nl)	2002-11-04	Polymeersamenstelling en werkwijze voor het bereiden daarvan.
US20030096914A1 (en)	2003-05-22	Polymer having combined linear and nonlinear structure and its preparing method
EP0273291B1 (de)	1994-11-02	Transparentes, hochschlagfestes Blockkopolymer
KR970009240B1 (ko)	1997-06-09	음이온 중합에 의한 알킬렌옥사이드와 비닐계 또는 디엔계 단량체와의 블럭 공중합 방법
KR0124953B1 (ko)	1997-12-01	표면에 관능기가 있는 분산 고분자의 제조 방법
CS233415B1 (en)	1985-03-14	Method of selective polymerization of butadiene with c4 fraction
KR930002989B1 (ko)	1993-04-16	단분산성 폴리스티렌의 제조방법