CA1134099A - Aldehydes a substitution dialkyle comme agents de transfert lineaire dans la polymerisation du chlorure de vinyle - Google Patents

Aldehydes a substitution dialkyle comme agents de transfert lineaire dans la polymerisation du chlorure de vinyle

Info

Publication number: CA1134099A
Authority: CA; Canada
Prior art keywords: vinyl chloride; chain transfer; transfer agent; polymer; weight
Prior art date: 1977-07-27
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

Application number

CA307,490A

Other languages

English (en)

Inventor

Bernard D. Bauman

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Air Products and Chemicals Inc

Original Assignee

Air Products and Chemicals Inc

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.)

1977-07-27

Filing date

1978-07-17

Publication date

1982-10-19

1978-07-17 Application filed by Air Products and Chemicals Inc filed Critical Air Products and Chemicals Inc

1982-10-19 Application granted granted Critical

1982-10-19 Publication of CA1134099A publication Critical patent/CA1134099A/fr

Status Expired legal-status Critical Current

Links

BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 title claims abstract description 14
239000012986 chain transfer agent Substances 0.000 title claims abstract description 9
150000001299 aldehydes Chemical class 0.000 title abstract description 12
238000006116 polymerization reaction Methods 0.000 title description 2
LGYNIFWIKSEESD-UHFFFAOYSA-N 2-ethylhexanal Chemical compound CCCCC(CC)C=O LGYNIFWIKSEESD-UHFFFAOYSA-N 0.000 claims abstract description 11
238000000034 method Methods 0.000 claims abstract description 10
229920001519 homopolymer Polymers 0.000 claims abstract description 8
239000000725 suspension Substances 0.000 claims abstract description 4
229920000642 polymer Polymers 0.000 claims description 21
239000000178 monomer Substances 0.000 claims description 9
150000003254 radicals Chemical class 0.000 claims description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
229920000915 polyvinyl chloride Polymers 0.000 claims description 4
239000004800 polyvinyl chloride Substances 0.000 claims description 4
239000003999 initiator Substances 0.000 claims description 3
239000000375 suspending agent Substances 0.000 claims description 2
230000006872 improvement Effects 0.000 claims 1
230000000379 polymerizing effect Effects 0.000 claims 1
238000000518 rheometry Methods 0.000 claims 1
229920001577 copolymer Polymers 0.000 abstract description 2
239000000839 emulsion Substances 0.000 abstract description 2
238000007720 emulsion polymerization reaction Methods 0.000 abstract description 2
238000004519 manufacturing process Methods 0.000 abstract description 2
238000010528 free radical solution polymerization reaction Methods 0.000 abstract 1
238000010557 suspension polymerization reaction Methods 0.000 abstract 1
239000003795 chemical substances by application Substances 0.000 description 16
239000011347 resin Substances 0.000 description 10
229920005989 resin Polymers 0.000 description 10
238000012546 transfer Methods 0.000 description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
125000000217 alkyl group Chemical group 0.000 description 6
229920002554 vinyl polymer Polymers 0.000 description 6
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 4
AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 4
-1 propyl3 butyl Chemical group 0.000 description 4
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 3
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
JARKCYVAAOWBJS-UHFFFAOYSA-N hexanal Chemical compound CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 description 3
150000002500 ions Chemical class 0.000 description 3
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
YGHRJJRRZDOVPD-UHFFFAOYSA-N 3-methylbutanal Chemical compound CC(C)CC=O YGHRJJRRZDOVPD-UHFFFAOYSA-N 0.000 description 2
HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
239000005977 Ethylene Substances 0.000 description 2
229940117913 acrylamide Drugs 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
ZQMIGQNCOMNODD-UHFFFAOYSA-N diacetyl peroxide Chemical compound CC(=O)OOC(C)=O ZQMIGQNCOMNODD-UHFFFAOYSA-N 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
239000000203 mixture Substances 0.000 description 2
238000000465 moulding Methods 0.000 description 2
229960002415 trichloroethylene Drugs 0.000 description 2
UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 2
JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 1
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
ZTVIKZXZYLEVOL-DGKWVBSXSA-N 2-hydroxy-2-phenylacetic acid [(1R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] ester Chemical group C([C@H]1CC[C@@H](C2)N1C)C2OC(=O)C(O)C1=CC=CC=C1 ZTVIKZXZYLEVOL-DGKWVBSXSA-N 0.000 description 1
NFPBWZOKGZKYRE-UHFFFAOYSA-N 2-propan-2-ylperoxypropane Chemical group CC(C)OOC(C)C NFPBWZOKGZKYRE-UHFFFAOYSA-N 0.000 description 1
101150034533 ATIC gene Proteins 0.000 description 1
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
239000004925 Acrylic resin Substances 0.000 description 1
229920000178 Acrylic resin Polymers 0.000 description 1
241000272808 Anser Species 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
241000861718 Chloris <Aves> Species 0.000 description 1
IWYRWIUNAVNFPE-UHFFFAOYSA-N Glycidaldehyde Chemical compound O=CC1CO1 IWYRWIUNAVNFPE-UHFFFAOYSA-N 0.000 description 1
239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
229930194542 Keto Natural products 0.000 description 1
239000004372 Polyvinyl alcohol Substances 0.000 description 1
NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 1
XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
208000027697 autoimmune lymphoproliferative syndrome due to CTLA4 haploinsuffiency Diseases 0.000 description 1
KQNZLOUWXSAZGD-UHFFFAOYSA-N benzylperoxymethylbenzene Chemical compound C=1C=CC=CC=1COOCC1=CC=CC=C1 KQNZLOUWXSAZGD-UHFFFAOYSA-N 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
239000008112 carboxymethyl-cellulose Substances 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
235000010980 cellulose Nutrition 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
239000004927 clay Substances 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 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 description 1
239000000975 dye Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
235000013305 food Nutrition 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
125000000468 ketone group Chemical group 0.000 description 1
239000000155 melt Substances 0.000 description 1
VKQFCGNPDRICFG-UHFFFAOYSA-N methyl 2-methylpropyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCC(C)C)C1C1=CC=CC=C1[N+]([O-])=O VKQFCGNPDRICFG-UHFFFAOYSA-N 0.000 description 1
239000011707 mineral Substances 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
238000004806 packaging method and process Methods 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000002904 solvent Substances 0.000 description 1
241000894007 species Species 0.000 description 1
235000015096 spirit Nutrition 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
229940035718 sular Drugs 0.000 description 1
BGRJTUBHPOOWDU-UHFFFAOYSA-N sulpiride Chemical compound CCN1CCCC1CNC(=O)C1=CC(S(N)(=O)=O)=CC=C1OC BGRJTUBHPOOWDU-UHFFFAOYSA-N 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
229920001897 terpolymer Polymers 0.000 description 1
OPQYOFWUFGEMRZ-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOC(=O)C(C)(C)C OPQYOFWUFGEMRZ-UHFFFAOYSA-N 0.000 description 1
KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F14/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen
- C08F14/02—Monomers containing chlorine
- C08F14/04—Monomers containing two carbon atoms
- C08F14/06—Vinyl chloride

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Polymerisation Methods In General (AREA)

CA307,490A 1977-07-27 1978-07-17 Aldehydes a substitution dialkyle comme agents de transfert lineaire dans la polymerisation du chlorure de vinyle Expired CA1134099A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US81955877A	1977-07-27	1977-07-27
US819,558		1977-07-27

Publications (1)

Publication Number	Publication Date
CA1134099A true CA1134099A (fr)	1982-10-19

Family

ID=25228469

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA307,490A Expired CA1134099A (fr)	1977-07-27	1978-07-17	Aldehydes a substitution dialkyle comme agents de transfert lineaire dans la polymerisation du chlorure de vinyle

Country Status (7)

Country	Link
JP (1)	JPS5424992A (fr)
BE (1)	BE869252A (fr)
CA (1)	CA1134099A (fr)
DE (1)	DE2832551A1 (fr)
FR (1)	FR2398763A1 (fr)
GB (1)	GB2001661B (fr)
NL (1)	NL7807851A (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB2004898B (en) *	1977-09-22	1982-02-24	Tenneco Chem	Production of vinyl halide polymers

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2729627A (en) *	1952-11-26	1956-01-03	Us Rubber Co	Polyvinyl chloride for use in plastisols
US4060677A (en) *	1975-02-25	1977-11-29	Hooker Chemicals & Plastics Corporation	Process for molecular weight lowering of vinyl halide polymers employing saturated carbon to carbon bonded aldehydes

1978
- 1978-07-17 CA CA307,490A patent/CA1134099A/fr not_active Expired
- 1978-07-21 FR FR7821657A patent/FR2398763A1/fr active Granted
- 1978-07-24 NL NL7807851A patent/NL7807851A/xx not_active Application Discontinuation
- 1978-07-25 BE BE189488A patent/BE869252A/fr not_active IP Right Cessation
- 1978-07-25 DE DE19782832551 patent/DE2832551A1/de not_active Withdrawn
- 1978-07-26 GB GB7831183A patent/GB2001661B/en not_active Expired
- 1978-07-26 JP JP9140478A patent/JPS5424992A/ja active Pending

Also Published As

Publication number	Publication date
FR2398763A1 (fr)	1979-02-23
BE869252A (fr)	1978-11-16
JPS5424992A (en)	1979-02-24
FR2398763B1 (fr)	1984-08-17
GB2001661A (en)	1979-02-07
DE2832551A1 (de)	1979-02-08
GB2001661B (en)	1982-02-10
NL7807851A (nl)	1979-01-30

Legal Events

Date	Code	Title	Description
1999-10-19	MKEX	Expiry

Publication	Publication Date	Title
US2882260A (en)	1959-04-14	Crosslinked polymers of ethylenically unsaturated blocked isocyanates
US2746944A (en)	1956-05-22	Process for preparing vinyl halide copolymers and copolymers produced thereby
US3839308A (en)	1974-10-01	Styrene-methacrylic acid copolymers and their preparation
EP0369727A1 (fr)	1990-05-23	Procédé de préparation de copolymères de tetrafluoroéthylène-éthylène
US4760152A (en)	1988-07-26	Pyrrolidonyl acrylate block polymers
US4143224A (en)	1979-03-06	Process for the manufacture of suspension polymers of vinyl chloride
CA1134099A (fr)	1982-10-19	Aldehydes a substitution dialkyle comme agents de transfert lineaire dans la polymerisation du chlorure de vinyle
US4251405A (en)	1981-02-17	Process for producing plasticized vinylidene chloride-vinyl chloride copolymer
US4806609A (en)	1989-02-21	Pyrrolidonyl acrylate block polymers
US3230203A (en)	1966-01-18	Process for the manufacture of copolymers of vinyl chloride
EP0195522B1 (fr)	1991-12-27	Composition polymère de chlorure de vinyle
US4401798A (en)	1983-08-30	Process for the production of vinyl halide polymers that uses an alkyl-substituted trisphenol as the chain-terminating agent
US3536675A (en)	1970-10-27	Process of polymerizing vinyl chloride in suspension
CA2057102A1 (fr)	1992-06-22	Methode de preparation de copolymeres d'acrylonitrile/methacrylonitrile transformables a l'etat fondu
US3585176A (en)	1971-06-15	Process for the peroxidic homopolymerization or copolymerization of vinyl monomers
US4521575A (en)	1985-06-04	Tetrafluoroethylene-ethylene type copolymer
CA1133196A (fr)	1982-10-05	Methode de fabrication en continu de polymeres de chlorure de vinyle
US5096988A (en)	1992-03-17	Process for preparing vinyl chloride polymer with two-stage addition of dispersion stabilizers
CA1225197A (fr)	1987-08-04	Production de polymeres d'halogenure de vinyle
US3812086A (en)	1974-05-21	Process for polymerizing vinyl chloride
EP0272012B1 (fr)	1992-08-19	Polymères, leur fabrication et leur application
US3037007A (en)	1962-05-29	Dispersing agents for ethylenically unsaturated compounds
EP0177974B1 (fr)	1990-09-12	Procédé de préparation d'une résine de chlorure de polyvinyle
US3565871A (en)	1971-02-23	Copolymers of ethylene and n-vinylazetidinones and process for preparing them
JPH10338701A (ja)	1998-12-22	塩化ビニル系重合体の製造方法