WO1998013392B1 - No-compounds for pseudo-living radical polymerization - Google Patents
No-compounds for pseudo-living radical polymerizationInfo
- Publication number
- WO1998013392B1 WO1998013392B1 PCT/EP1997/005009 EP9705009W WO9813392B1 WO 1998013392 B1 WO1998013392 B1 WO 1998013392B1 EP 9705009 W EP9705009 W EP 9705009W WO 9813392 B1 WO9813392 B1 WO 9813392B1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- groups
- hydroxylamine
- tris
- radical polymerization
- free radical
- Prior art date
Links
- 238000010526 radical polymerization reaction Methods 0.000 title claims abstract 4
- 238000000034 method Methods 0.000 claims abstract 5
- 150000001205 NO derivatives Chemical class 0.000 claims abstract 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract 3
- 230000000295 complement Effects 0.000 claims abstract 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 3
- 229920000642 polymer Polymers 0.000 claims abstract 3
- 238000004064 recycling Methods 0.000 claims abstract 3
- 229910052799 carbon Inorganic materials 0.000 claims abstract 2
- 125000004432 carbon atoms Chemical group C* 0.000 claims abstract 2
- 229920001577 copolymer Polymers 0.000 claims abstract 2
- 125000004122 cyclic group Chemical group 0.000 claims abstract 2
- 125000000524 functional group Chemical group 0.000 claims abstract 2
- 230000000977 initiatory Effects 0.000 claims abstract 2
- 150000008064 anhydrides Chemical class 0.000 claims 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
- IBAHLNWTOIHLKE-UHFFFAOYSA-N cyano cyanate Chemical compound N#COC#N IBAHLNWTOIHLKE-UHFFFAOYSA-N 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- LXQTYQSAEZCVKJ-UHFFFAOYSA-N 1-[(1-cyanocyclohexyl)-(1-cyanocyclohexyl)oxyamino]cyclohexane-1-carbonitrile Chemical compound C1CCCCC1(C#N)N(C1(CCCCC1)C#N)OC1(C#N)CCCCC1 LXQTYQSAEZCVKJ-UHFFFAOYSA-N 0.000 claims 1
- IDJVUSYCRWRGGR-UHFFFAOYSA-N 2-[2-cyanopropan-2-yl(2-cyanopropan-2-yloxy)amino]-2-methylpropanenitrile Chemical compound N#CC(C)(C)ON(C(C)(C)C#N)C(C)(C)C#N IDJVUSYCRWRGGR-UHFFFAOYSA-N 0.000 claims 1
- YDQHTZQPKOMBTH-UHFFFAOYSA-N 3-[(1-carboxy-2-methylpropan-2-yl)-(1-carboxy-2-methylpropan-2-yl)oxyamino]-3-methylbutanoic acid Chemical compound OC(=O)CC(C)(C)ON(C(C)(C)CC(O)=O)C(C)(C)CC(O)=O YDQHTZQPKOMBTH-UHFFFAOYSA-N 0.000 claims 1
- ZBTDAMRWKVYERG-UHFFFAOYSA-N 5-[5-carboxypentan-2-yl(5-carboxypentan-2-yloxy)amino]hexanoic acid Chemical compound OC(=O)CCCC(C)ON(C(C)CCCC(O)=O)C(C)CCCC(O)=O ZBTDAMRWKVYERG-UHFFFAOYSA-N 0.000 claims 1
- 125000004181 carboxyalkyl group Chemical group 0.000 claims 1
- -1 dialkoxyphosphonyl Chemical group 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 238000010550 living polymerization reaction Methods 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 125000004416 alkarylalkyl group Chemical group 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
Abstract
The invention pertains to a process for pseudo-living radical polymerization's in which use is made of specific NO-compounds, called initers, according to formula (I) or (II) wherein: R represents a group which has at least one carbon atom and is such that the free radical R. is capable of initiating the free radical polymerization of unsaturated monomers; at most five of the groups represented by X1-X6 are the same or different straight-chain or branched substituted or unsubstituted alkyl groups, wherein two or more of the groups may be linked to form cyclic structures, or wherein -CX1X2X3 and/or -CX4X5X6 are phenyl, the complementary groups X1-X6 are functional groups, and, X7 and X8 are independently selected from alkyl, aryl, alkaryl, and aralkyl, while X7 is optionally linked with X8 to form bridged structures. The invention further relates to certain NO compounds, (block) (co)polymers, and to a recycling process for such polymers.
Claims
AMENDED CLAIMS
[received by the International Bureau on 29 April 1998 (29.04.98); original claim 10 amended; remaining claims unchanged (2 pages)]
9. A (block) (co)polymer obtainable by any one of the processes of claims 1-8.
10. An NO-compound containing at least one moiety of the formula (I),
R O
• R represents a group which has at least one carbon atom and is such that the free radical R* is capable of initiating the free radical polymerization of unsaturated monomers;
• at most five of the groups represented by X^ through Xβ are the same or different straight-chain or branched substituted or unsubstituted (cyclo) alkyl groups, while two or more of the groups may be linked to form cyclic structures, • the complementary groups Xi through Xβ are functional groups selected from substituted or unsubstituted phenyl, cyano, ether, hydroxy, nitro, dialkoxyphosphonyl, and carbonyl containing groups, such as ester, carboxyalkyl, aldehyde, anhydride, and ketoalk(ar)yl groups, and • R is not polymeric when -N(CXιX2X3) 0X4X5X5 is 2,5-dimethyl-2,5- diphenylpyrrolidin-1 -, with the proviso that the NO-compound is not tris-(2-cyano-2-propyl)- hydroxylamine, tris-(2-carboxyethyl-2-propyl) hydroxylamine, tris-(1- cyanocyclohexyl) hydroxylamine, and/or tris-(2-carboxymethyl-2-propyl) hydroxylamine.
11. An NO-compound according to claim 10, characterized in that the complementary groups X are selected from substituted or unsubstituted phenyl, cyano, ether, and carbonyl containing groups, such as ester, anhydride, and ketoalk(ar)yl groups.
12. A recycling process in which a polymer is converted into low-molecular weight fragments, characterized in that the polymer is obtained from a pseudo-living polymerization process according to any one of claims 1-8.
13. A recycling process according to claim 12, characterized in that the processing temperature is below 300°C.
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP97910285A EP0928296B1 (en) | 1996-09-25 | 1997-09-11 | No-compounds for pseudo-living radical polymerization |
| DE69708896T DE69708896T2 (en) | 1996-09-25 | 1997-09-11 | NITROSO CONNECTIONS TO PSEUDO-LIVING RADICAL POLYMERIZATION |
| JP10515215A JP2001500914A (en) | 1996-09-25 | 1997-09-11 | NO compounds for simulated living radical polymerization |
| AT97910285T ATE210156T1 (en) | 1996-09-25 | 1997-09-11 | NITROSO COMPOUNDS FOR PSEUDO-LIVING RADICAL POLYMERIZATION |
| AU47739/97A AU4773997A (en) | 1996-09-25 | 1997-09-11 | No-compounds for pseudo-living radical polymerization |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP96202676 | 1996-09-25 | ||
| EP96202676.1 | 1996-09-25 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO1998013392A1 WO1998013392A1 (en) | 1998-04-02 |
| WO1998013392B1 true WO1998013392B1 (en) | 1998-06-18 |
Family
ID=8224422
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP1997/005009 WO1998013392A1 (en) | 1996-09-25 | 1997-09-11 | No-compounds for pseudo-living radical polymerization |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP0928296B1 (en) |
| JP (1) | JP2001500914A (en) |
| AT (1) | ATE210156T1 (en) |
| AU (1) | AU4773997A (en) |
| DE (1) | DE69708896T2 (en) |
| WO (1) | WO1998013392A1 (en) |
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| ES2246585T3 (en) | 1998-12-21 | 2006-02-16 | Ciba Specialty Chemicals Holding Inc. | COMPOSITION AND PROCEDURE FOR CONTROLLED RADICAL POLYMERIZATION USING MULTIFUNCTIONAL INITIATOR COMPOUNDS / REGULATORS. |
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| CN109071422A (en) * | 2015-11-04 | 2018-12-21 | 迪斯普泰科有限公司 | The regulator that linear and false ring extension for controlling vinyl monomer polymerize |
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Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU571240B2 (en) * | 1983-07-11 | 1988-04-14 | Commonwealth Scientific And Industrial Research Organisation | Alkoxy-amines, useful as initiators |
| US5627248A (en) * | 1995-09-26 | 1997-05-06 | The Dow Chemical Company | Difunctional living free radical polymerization initiators |
-
1997
- 1997-09-11 DE DE69708896T patent/DE69708896T2/en not_active Expired - Fee Related
- 1997-09-11 AU AU47739/97A patent/AU4773997A/en not_active Abandoned
- 1997-09-11 EP EP97910285A patent/EP0928296B1/en not_active Expired - Lifetime
- 1997-09-11 JP JP10515215A patent/JP2001500914A/en active Pending
- 1997-09-11 AT AT97910285T patent/ATE210156T1/en not_active IP Right Cessation
- 1997-09-11 WO PCT/EP1997/005009 patent/WO1998013392A1/en active IP Right Grant
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