# US 8,785,553 B2 · Moisture curable propylene-α-olefin copolymers

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- Number: US 8,785,553 B2
- Document ID: US8785553B2
- Status: Granted
- Kind: B2
- Application number: 11/950,333
- Filed: 2007-12-04
- Published: 2009-06-04
- Granted: 2014-07-22
- Earliest claimed: 2007-12-04
- Assignees: ExxonMobil Chemical Patents Inc.
- Applicants: Trazollah Ouhadi; Jean-Roch H. Schauder
- Inventors: Trazollah Ouhadi; Jean-Roch H. Schauder
- Web page: https://patentgrep.com/patent/US8785553B2

## CPC

- C08F 8/42: Introducing metal atoms or metal-containing groups
- C08F 8/00: Chemical modification by after-treatment (graft polymers, block polymers, crosslinking with unsaturated monomers or with polymers C08F251/00 - C08F299/00; of conjugated diene rubbers C08C)
- C08F 255/04: on to ethylene-propylene copolymers {(C08F255/023 takes precedence)}
- C08F 255/06: on to ethylene-propylene-diene terpolymers {(C08F255/023 takes precedence)}
- C08J 3/24: Crosslinking, e.g. vulcanising, of macromolecules (mechanical aspects B29C35/00; crosslinking agents C08K)
- C08L 23/04: Homopolymers or copolymers of ethene
- C08L 23/10: Homopolymers or copolymers of propene
- C09J 151/06: grafted on to homopolymers or copolymers of aliphatic hydrocarbons containing only one carbon-to-carbon double bond
- C09K 3/1018: {Macromolecular compounds having one or more carbon-to-silicon linkages}
- C09K 3/24: for simulating ice or snow
- C08J 2300/108: containing hydrolysable silane groups
- C08J 2323/04: Homopolymers or copolymers of ethene
- C08J 2323/10: Homopolymers or copolymers of propene
- C08L 2666/14: Macromolecular compounds according to C08L59/00 - C08L87/00; Derivatives thereof
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08J: WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H (working, e.g. shaping, of plastics B29)
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- C09J: ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES (preparation of glue or gelatine C09H)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE

## Abstract

An aspect of the description is directed to hydrolysable silane graft propylene-α-olefin copolymers useful for moisture curable sealants, the copolymers comprising a propylene-α-olefin copolymer component comprising propylene-derived units and from 5 to 35 wt %, by weight of the propylene-α-olefin copolymer, of ethylene-derived units or a C4 to C10 α-olefin-derived unit, and having, in one embodiment, the following features: a density of from 0.850 to 0.920 g/cm3; a MWD of from 1.5 to 20; an Hf of less than or equal to 75 J/g; a Tm of from 25 to 105° C.; and a triad tacticity by 13C NMR of 75% or greater; and a hydrolysable silane component. The graft copolymer can be combined with oil and/or a thermoplastic to form a graft copolymer composition capable of being cross-linked by exposure to moisture.

## Claims

### Claim 1

A graft copolymer composition comprising a hydrolizable silane graft propylene-α-olefin copolymer, the composition comprising:
a hydrolizable silane graft propylene-α-olefin copolymer comprising a propylene-α-olefin copolymer component and a hydrolizable silane component, and
from 0.1 to 5 wt %, based on total weight of the hydrolizable silane graft propylene-α-olefin copolymer, of at least one silanol condensation catalyst:
wherein the propylene-α-olefin copolymer component comprises propylene-derived units and from 5 to 20 wt %, by weight of the propylene-α-olefin copolymer, of ethylene-derived units or C4 to C10 α-olefin-derived units, and having:
(i) a density of from 0.850 to 0.920 g/cm3;
(ii) a MWD of from 1.5 to 20;
(iii) an Hf of less than or equal to 75 J/g;
(iv) a Tm of from 25 to 105° C.;
(v) a triad tacticity by 13C NMR of 75% or greater;
(vi) a melt flow rate (2.16 kg, 230° C.) of from 0.2 to 100 dg/min;
(vii) a weight average molecular weight of 50,000 to 400,000; and
(viii) a number average molecular weight of 25,000 to 200,000; and
wherein the cured graft copolymer composition comprising the hydrolizable silane graft copolymer has an Elongation at Break as determined by ISO-37 (500 mm/min, 23° C.) greater than 400%;
wherein the hydrolizable silane component is derived from a vinyl silane having the following formula: YSiRR″2, wherein Y is selected from vinyl terminated radicals, each R″ is independently selected from hydrolizable organic radicals; and R can be an R″ radical, or selected from C1 to C10 alkyl radicals (both R and R″ are bound to the silicon atom); and
wherein the graft copolymer has a haze value of from less than 15%.

### Claim 2 (depends on 1)

The graft copolymer composition of claim 1, wherein the propylene-α-olefin copolymer comprises from 6 to 20 wt % ethylene-derived units.

### Claim 3 (depends on 1)

The graft copolymer composition of claim 1, wherein the Hf of the propylene-α-olefin copolymer is less than or equal to 60 J/g.

### Claim 4 (depends on 1)

The graft copolymer composition of claim 1, wherein the composition comprises from 0.03 to 5 wt % of the hydrolizable silane component, based on weight of the hydrolizable silane graft propylene-α-olefin copolymer.

### Claim 5 (depends on 1)

The graft copolymer composition of claim 1, wherein the propylene-α-olefin copolymer also comprises from 0.1 to 6 wt % diene-derived units.

### Claim 6

A composition consisting of:
(a) a hydrolizable silane graft propylene-α-olefin copolymer comprising propylene-derived units and from 11 to 20 wt %, by weight of the propylene-α-olefin copolymer, of ethylene-derived units or C4 to C10 α-olefin-derived units, and having:
(i) a density of from 0.850 to 0.920 g/cm3;
(ii) a MWD of from 1.5 to 20;
(iii) an Hf of less than or equal to 75 J/g;
(iv) a Tm of from 25 to 105° C.;
(v) a triad tacticity by 13C NMR of 75% or greater;
(vi) a melt flow rate (2.16 kg, 230° C.) of from 0.2 to 100 dg/min;
(vii) a weight average molecular weight of 50,000 to 400,000;
(viii) a number average molecular weight of 25,000 to 200,000; and
(ix) a hydrolizable silane component;
(b) a non-grafted polymer selected from propylene homopolymers, propylene random copolymers, impact copolymers, plastomers, polyethylenes, and combinations thereof;
(c) oil and filter; and
(d) from 0.1 to 5 wt %, based on total weight of the hydrolizable silane graft propylene-α-olefin copolymer, of at least one silanol condensation catalyst;
wherein the cured composition has an Elongation at Break as determined by ISO-37 (500 mm/min, 23° C.) greater than 400%;
wherein the hydrolizable silane component is derived from an amino silane having the following formula: YHN(CH2)nSiRR″2, wherein N is a nitrogen atom, n is from 1 to 20 and wherein Y radical is either hydrogen or one alkyl radical C1 to C20 alkyl radical terminated by —NH2; R″ is selected from hydrolizable organic radicals, and R can be an alkyl group or a R″ radical, or selected from C1 to C10 alkyl radicals; and
wherein the raft copolymer has a haze value of from less than 15%.

### Claim 7 (depends on 6)

The composition of claim 6, wherein the composition includes from 1 to 60 wt %, by weight of the composition, of the non-grafted polymer.

### Claim 8 (depends on 7)

The composition of claim 7, wherein the composition includes from 5 to 60 wt % of the oil.

### Claim 9 (depends on 1)

A moisture curable sealant formed from the graft copolymer composition of claim 1.

### Claim 10 (depends on 6)

The composition of claim 6, wherein the propylene-α-olefin copolymer also comprises from 0.1 to 6 wt % diene-derived units.

### Claim 11 (depends on 1)

The graft copolymer composition of claim 1, wherein the composition comprises from 0.1 to 1 wt %, based on total weight of the hydrolizable silane graft propylene-α-olefin copolymer, of at least one silanol condensation catalyst.

### Claim 12 (depends on 6)

The composition of claim 6, wherein the composition comprises from 0.1 to 1 wt %, based on total weight of the hydrolizable silane graft propylene-α-olefin copolymer, of at least one silanol condensation catalyst.

### Claim 13 (depends on 1)

The composition of claim 1, wherein the graft copolymer composition is cross-linked upon exposure to a liquid or vapor water.

### Claim 14 (depends on 6)

The composition of claim 6, wherein the graft copolymer composition is cross-linked upon exposure to a liquid or vapor water.