Polyolefin resin composition

• US 5,218,048 A
• Filed: 12/10/1990
• Issued: 06/08/1993
• Est. Priority Date: 12/11/1989
• Status: Expired due to Term

• Current Assignee: Sumitomo Chemical Company Limited
• Original Assignee: Sumitomo Chemical Company Limited
• Inventors: Sanada, Takashi, Nagaoka, Kenji, Abe, Hiroomi
• Primary Examiner(s): Kight, III, John
• Assistant Examiner(s): DODSON, SHELLEY A
• Application Number:
  US07/624,563
• Time in Patent Office: 911 Days
• Field of Search: 525/57, 525/64, 525/66, 525/67, 525/68, 525/84, 525/95, 525/96, 525/98, 525/282, 525/285, 525/296, 525/301, 525/189, 525/92, 525/133, 525/146
• US Class Current: 525/92.00D
• CPC Class Codes: C08F 110/06 Propene
• CPC Class Codes: C08F 112/08 Styrene
• CPC Class Codes: C08F 210/16 Copolymers of ethene with alpha-alkenes, e.g. EP rubbers
• CPC Class Codes: C08F 2800/20 as weight or mass percentages
• CPC Class Codes: C08F 8/30 Introducing nitrogen atoms or nitrogen-containing groups
• CPC Class Codes: C08F 8/46 Reaction with unsaturated dicarboxylic acids or anhydrides thereof, e.g. maleinisation
• CPC Class Codes: C08K 5/17 Amines; Quaternary ammonium compounds
• CPC Class Codes: C08L 2205/04 containing interpenetrating networks
• CPC Class Codes: C08L 2205/08 containing additives to improve the compatibility between two polymers
• CPC Class Codes: C08L 23/02 not modified by chemical after-treatment
• CPC Class Codes: C08L 23/10 Homopolymers or copolymers of propene
• CPC Class Codes: C08L 2666/04 Macromolecular compounds according to groups C08L7/00 - C08L49/00, or C08L55/00 - C08L57/00; Derivatives thereof
• CPC Class Codes: C08L 2666/14 Macromolecular compounds according to C08L59/00 - C08L87/00; Derivatives thereof
• CPC Class Codes: C08L 51/06 grafted on to homopolymers or copolymers of aliphatic hydrocarbons containing only one carbon-to-carbon double bond

Abstract

A resin composition comprising (A) a thermoplastic resin, (B) a functional compound having one or more bonds or one or more functional groups selected from the group consisting of organic groups having a non-aromatic carbon-carbon multiple bonds, oxirane groups and substituted carboxyl groups and (C) a diamino compound represented by the following general formula:

R.sup.I NH--X--NHR.sup.II

wherein R^I and R^II each represents a hydrogen atom or an alkyl group optionally having one or more inactive substituents, and X represents an alkylene group having 7 to 30 carbon atoms and optionally having one or more inactive substituents.

Claims

1. A resin composition comprising

(A) a thermoplastic resin or resin mixture comprising a polyolefin resin alone or in admixture with at least one member selected from the group consisting of another thermoplastic resin and an elastomer,

(B) a functional compound having one or more bonds or one or more functional groups selected from the group consisting of non-aromatic carbon-carbon multiple bonds, oxirane groups and substituted carboxyl groups selected from the group consisting of --COOR₁, --COX, --CONR₂ R₃ and --CO--Y--CO--, wherein R₁ represents hydrogen or an alkyl or aryl having 1-20 carbon atoms optionally having one or more inactive substituents, X represents halogen, R₂ and R₃ each represents hydrogen or an alkyl or aryl having 1-10 carbon atoms optionally having one or more inactive substituents, and Y represents oxygen or NH, and

(C) a diamino compound represented by the formula:

space="preserve" listing-type="equation">R.sup.I NH--X--NHR.sup.II

wherein R^I and R^II each represents hydrogen or alkyl optionally having one or more inactive substituents, and X represents an alkylene group having 7 to 30 carbon atoms and optionally one or more inactive substituents,

wherein the inactive substituents are selected from the group consisting of aryl, halogen, cyano, nitro, carbonyl, sulfonyl, ether, sulfide, ester and amido.

2. A resin composition according to claim 1, wherein said thermoplastic resin (A) is a polyolefin resin.

3. A resin composition according to claim 1, wherein said diamino compound is a diamino compound represented by the formula:

space="preserve" listing-type="equation">NH.sub.2 --X--NH.sub.2

wherein X represents a straight chain alkylene group having 8 to 20 carbon atoms.

4. A resin composition according to claim 1, wherein said functional compound is a functional compound simultaneously having

(i) at least one bond or functional group selected from the group consisting of non-aromatic carbon-carbon multiple bonds, oxirane groups and substituted carboxyl groups selected from the group consisting of --COOR₁, --COX, --CONR₂ R₃ and --CO--Y--CO--, wherein R₁ represents hydrogen or an alkyl or aryl having 1-20 carbon atoms optionally having one or more inactive substituents, X represents halogen, R₂ and R₃ each represents hydrogen or an alkyl or aryl having 1-10 carbon atoms optionally having one or more inactive substituents, and Y represents oxygen or NH, and

(ii) at least one functional group selected from the group consisting of

substituted carboxyl groups selected from the group consisting of --COOR₁, --COX, --CONR₂ R₃ and --CO--Y--CO--, wherein R₁ represents hydrogen or an alkyl or aryl having 1-20 carbon atoms optionally having one or more inactive substituents, X represents halogen, R₂ and R₃ each represents hydrogen or an alkyl or aryl having 1-10 carbon atoms optionally having one or more inactive substituents, and Y represents oxygen or NH,

substituted hydroxyl groups selected from the group consisting of --OR₄, ##STR9## and --OSi(R)₆)₃, wherein R₄ and R₅ each represent hydrogen or an alkyl or aryl having 1-10 carbon atoms optionally having one or more inactive substituents, and the three R₆ s each represent identical or different alkyl, aryl or alkoxy having 1-10 carbon atoms optionally having one or more inactive substituents,

substituted amino groups selected from the group consisting of --NHR₇ and ##STR10## wherein R₇ represents hydrogen, cyano or an alkyl or aryl having 1-10 carbon atoms optionally having one or more inactive substituents, and R₈ represents hydrogen or an alkyl or aryl having 1-20 carbon atoms optionally having one or more inactive substituents,

substituted silyl groups of the formula --Si(R₉)₃, wherein the three R₉ s each represent hydrogen or identical or different alkyl, aryl or alkoxy having 1-10 carbon atoms optionally having one or more amino or mercapto,

substituted mercapto groups selected from the group consisting of --SR₁₀ and ##STR11## wherein R₁₀ and R₁₁ each represents hydrogen or an alkyl or aryl having 1-10 carbon atoms optionally having one or more inactive groups,

substituted sulfonic acid groups selected from the group consisting of --SO₃ R₁₂, --SO₂ X and --SO₂ NR₁₃ R₁₄, wherein R₁₂ represents hydrogen or an alkyl or aryl having 1-20 carbon atoms optionally having one or more inactive substituents, X represents halogen, and R₁₃ and R₁₄ each represent hydrogen or an alkyl or aryl having 1-10 carbon atoms optionally having one or more inactive substituents and

oxirane groups,

wherein the inactive substituents are selected from the group consisting of aryl, halogen, cyano, nitro, carbonyl, sulfonyl, ether, sulfide, ester and amido,

provided that the functional group of (ii) is different from the functional group of (i).

5. A resin composition according to claim 1, wherein said thermoplastic resin is a resin mixture consisting of a polyolefin resin and another thermoplastic resin.

6. A resin composition according to claim 1, wherein said thermoplastic resin is a resin mixture consisting of a polyolefin resin, another thermoplastic resin and an elastomer.

7. A resin composition according to claim 5, wherein said other thermoplastic resin is a polyphenylene ether resin.

8. A resin composition according to claim 5, wherein said other thermoplastic resin is a styrene resin.

9. A resin composition according to claim 5, wherein said other thermoplastic resin is a polyarylene sulfide resin.

10. A resin composition according to claim 1, wherein said diamino compound (C) is 1,12-diaminododecane.

15. A resin composition according to claim 6, wherein said other thermoplastic resin is a polyphenylene ether resin.

16. A resin composition according to claim 6, wherein said other thermoplastic resin is a styrene resin.

17. A resin composition according to claim 6, wherein said other thermoplastic resin is a polyarylene sulfide resin.

11. A process for producing a resin composition which comprises

melting and kneading

(A) a thermoplastic resin which is a polyolefin resin together with

(B) a functional compound having one or more bonds or one or more functional groups selected from the group consisting of non-aromatic carbon-carbon multiple bonds, oxirane groups and substituted carboxyl groups selected from the group consisting of --COOR₁, --COX, --CONR₂ R₃ and --CO--Y--CO--, wherein R₁ represents hydrogen or an alkyl or aryl having 1-20 carbon atoms optionally having one or more inactive substituents, X represents halogen, R₂ and R₃ each represents hydrogen or an alkyl or aryl having 1-10 carbon atoms optionally having one or more inactive substituents, and Y represents oxygen or NH, and

subsequently mixing thereinto

(C) a diamino compound represented by the following general formula:

space="preserve" listing-type="equation">R.sup.I NH--X--NHR.sup.II

wherein R^I and R^II each represents hydrogen or alkyl optionally having one or more inactive substituents and X represents an alkylene group having 7 to 30 carbon atoms and optionally having one or more inactive substituents

wherein the inactive substituents are selected from the group consisting of aryl, halogen, cyano, nitro, carbonyl, sulfonyl, either, sulfide, ester and amido.

12. A process for producing a resin composition according to claim 11, wherein said functional compound is a functional compound simultaneously having

(i) at least one bond or functional group selected from the group consisting of non-aromatic carbon-carbon multiple bonds, oxirane groups and substituted carboxyl groups selected from the group consisting of --COOR₁, --COX, --CONR₂ R₃ and --CO--Y--CO--, wherein R₁ represents hydrogen or an alkyl or aryl having 1-20 carbon atoms optionally having one or more inactive substituents, X represents halogen, R₂ and R₃ each represents hydrogen or an alkyl or aryl having 1-10 carbon atoms optionally having one or more inactive substituents, and Y represents oxygen or NH, and

(ii) at least one functional group selected from the group consisting of

substituted carboxyl groups selected from the group consisting of --COOR₁, --COX, --CONR₂ R₃ and --CO--Y--, wherein R₁ represents hydrogen or an alkyl or aryl having 1-20 carbon atoms optionally having one or more inactive substituents, X represents halogen, R₂ and R₃ each represents hydrogen or an alkyl or aryl having 1-10 carbon atoms optionally having one or more inactive substituents, and Y represents oxygen or NH,

substituted hydroxyl groups selected from the group consisting of --OR₄, ##STR12## and --OSi(R₆)₃, wherein R₄ and R₅ each represent hydrogen or an alkyl or aryl having 1-10 carbon atoms optionally having one or more inactive substituents, and the three R₆ s each represent identical or different alkyl, aryl or alkoxy having 1-10 carbon atoms optionally having one or more inactive substituents,

substituted amino groups selected from the group consisting of --NHR₇ and ##STR13## wherein R₇ represents hydrogen, cyano or an alkyl or aryl having 1-10 carbon atoms optionally having one or more inactive substituents, and R₈ represents hydrogen or an alkyl or aryl having 1-20 carbon atoms optionally having one or more inactive substituents,

substituted silyl groups of the formula --Si(R₉)₃, wherein the three R₉ s each represent hydrogen or identical or different alkyl, aryl or alkoxy having 1-10 carbon atoms optionally having one or more amino or mercapto,

substituted mercapto groups selected from the group consisting of --SR₁₀ and ##STR14## wherein R₁₀ and R₁₁ each represents hydrogen or an alkyl or aryl having 1-10 carbon atoms optionally having one or more inactive groups,

substituted sulfonic acid groups selected from the group consisting of --SO₃ R₁₂, --SO₂ X and --SO₂ NR₁₃₁₄, wherein R₁₂ represents hydrogen or an alkyl or aryl having 1-20 carbon atoms optionally having one or more inactive substituents, X represents halogen, and R₁₃ and R₁₄ each represent hydrogen or an alkyl or aryl having 1-10 carbon atoms optionally having one or more inactive substituents and

oxirane groups,

wherein the inactive substituents are selected from the group consisting of aryl, halogen, cyano, nitro, carbonyl, sulfonyl, ether, sulfide, ester and amido,

provided that the functional group of (ii) is different from the functional group of (i).

13. A process for producing a resin composition according to claim 11, wherein said thermoplastic resin (A) is a resin mixture consisting of a polyolefin resin and another thermoplastic resin.

14. A process for producing a resin composition according to claim 11, wherein said thermoplastic resin (A) is a resin mixture consisting of a polyolefin resin, another thermoplastic resin and an elastomer.