IP Library Granted Patent US 9,840,581
Granted Patent B2
US 9,840,581 · App. 14/774,550 · Granted Dec 12, 2017

Use of polyesters having inherent flame protection in adhesives and sealants

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Quick Facts
Patent No.
US 9,840,581
App. No.
14/774,550
Granted
Dec 12, 2017
Kind
B2
Abstract

The present invention relates to the use of polyesters with inherent flame retardancy as or in adhesives, sealants and coatings, to polyesters with inherent flame retardancy and to processes for production thereof.

Claims (76)

1. A process for making a flame-retardant hot-melt adhesive, the process comprising

mixing a mixture comprising a flame-retardant polyester to obtain the flame-retardant hot-melt adhesive,

wherein:

the flame-retardant polyester is formed from adipic acid, 1,6-hexanediol, neopentyl glycol, and a diol of formula (I):

where

R is a saturated linear or branched alkyl moiety having from 1 to 10 C atoms, and

A and B are identical or different and are saturated linear or branched alkylene groups having from 1 to 10 C atoms or are mono- or polyalkylene glycol groups; and

no other diols or polyols having ether groups in addition to the diol of the formula (I) are used to form the flame-retardant polyester.

2. The process of claim 1 , wherein the flame-retardant hot-melt adhesive is a reactive hot-melt adhesive.

3. The process of claim 1 , wherein A and B are identical or different and are mono- or polyalkylene glycol groups, which are ethylene glycol groups of formula —CH 2 —CH 2 (—O—CH 2 —CH 2 ) n — or propylene glycol groups of formula —CH 2 —CHCH 3 (—O—CH 2 —CHCH 3 ) n —, where n is an integer from 1 to 10.

4. The process of claim 1 , wherein the diol of the formula (I) is bis[2-(2-hydroxyethoxy) ethyl] methanephosphonate.

5. An adhesive, sealant or coating, comprising

a polyester formed from adipic acid, 1,6-hexanediol, neopentyl glycol, and a diol of formula (I):

where

R is a saturated linear or branched alkyl moiety having from 1 to 10 C atoms, and

A and B are identical or different and are saturated linear or branched alkylene groups having from 1 to 10 C atoms or are mono- or polyalkylene glycol groups; and

no other diols or polyols having ether groups in addition to the diol of the formula (I) are used to form the polyester.

6. The adhesive, sealant or coating of claim 5 , which is a hot-melt adhesive.

7. The adhesive, sealant or coating of claim 6 , which is a reactive hot-melt adhesive.

8. A polyester, formed from adipic acid, 1,6-hexanediol, neopentyl glycol, and a diol of formula (I):

where

R is a saturated linear or branched alkyl moiety having from 1 to 10 C atoms; and

A and B are identical or different and are saturated linear or branched alkylene groups having from 1 to 10 C atoms or are mono- or polyalkylene glycol groups,

wherein no other di- or polycarboxylic acid or a derivative thereof in addition to adipic acid is used to form the polyester.

9. The polyester of claim 8 , wherein A and B are identical or different and are mono- or polyalkylene glycol groups, which are ethylene glycol groups of the general formula —CH 2 —CH 2 (—O—CH 2 —CH 2 ) n — or propylene glycol groups of formula —CH 2 —CHCH 3 (—O—CH 2 —CHCH 3 ) n —, where n is an integer from 1 to 10.

10. The polyester of claim 8 , wherein the diol of the formula (I) is bis[2-(2-hydroxyethoxy)ethyl] methanephosphonate.

11. The process of claim 1 , wherein a proportion of the diol of the formula (I) is from 4 to 12 mol % based on an entirety of the di- or polyols in the mixture.

12. The process of claim 1 , wherein the mixing takes place in a melt.

13. A process for making a flame-retardant hot-melt adhesive, the process comprising

mixing a mixture comprising a flame-retardant polyester and at least one of an isocyanate and a polyisocyanate to obtain the flame-retardant hot-melt adhesive,

wherein:

the flame-retardant polyester is formed from at least one di- or polycarboxylic acid and at least one di- or polyol;

the flame-retardant polyester is formed from at least one diol of formula (I):

where

R is a saturated linear or branched alkyl moiety having from 1 to 10 C atoms, and

A and B are identical or different and are saturated linear or branched alkylene groups having from 1 to 10 C atoms or are mono- or polyalkylene glycol groups; and

no other diols or polyols having ether groups are present in addition to the diol of the formula (I) in the flame-retardant polyester.

14. The process of claim 13 , wherein a ratio of OH:NCO in the mixture is from 1:1.2 to 1:3.

15. A process for making a flame-retardant hot-melt adhesive, the process comprising

mixing a mixture comprising a flame-retardant polyester and an organosilane to obtain the flame-retardant hot-melt adhesive,

wherein:

the flame-retardant polyester is formed from at least one di- or polycarboxylic acid and at least one di- or polyol;

the flame-retardant polyester is formed from at least one diol of formula (I):

where

R is a saturated linear or branched alkyl moiety having from 1 to 10 C atoms, and

A and B are identical or different and are saturated linear or branched alkylene groups having from 1 to 10 C atoms or are mono- or polyalkylene glycol groups; and

no other diols or polyols having ether groups are present in addition to the diol of the formula (I) in the flame-retardant polyester.

16. An adhesive, sealant, or coating, comprising

a polyester formed from at least one di- and/or polycarboxylic acid and at least one di- and/or polyol, and

at least one of an isocyanate and a polyisocyanate,

wherein

the polyester is formed from at least one diol of formula (I):

where

R is a saturated linear or branched alkyl moiety having from 1 to 10 C atoms, and

A and B are identical or different and are saturated linear or branched alkylene groups having from 1 to 10 C atoms or are mono- or polyalkylene glycol groups; and

no other diols or polyols having ether groups are present in addition to the diol of the formula (I) in the polyester.

17. An adhesive, sealant, or coating, comprising:

a polyester formed from at least one di- and/or polycarboxylic acid and at least one di- and/or polyol, and

an organosilane,

wherein

the polyester is formed from at least one dial of formula (I):

where

R is a saturated linear or branched alkyl moiety having from 1 to 10 C atoms, and

A and B are identical or different and are saturated linear or branched alkylene groups having from 1 to 10 C atoms or are mono- or polyalkylene glycol groups; and

no other diols or polyols having ether groups are present in addition to the diol of the formula (I) in the polyester.

18. The polyester of claim 8 , which has a functionality of 1.0 to 3.0.

19. The process of claim 13 , wherein the flame-retardant hot-melt adhesive is a reactive hot-melt adhesive.

20. The process of claim 13 , wherein A and B are identical or different and are mono- or polyalkylene glycol groups, which are ethylene glycol groups of formula —CH 2 —CH 2 (—O—CH 2 —CH 2 ) n — or propylene glycol groups of formula —CH 2 —CHCH 3 (—O—CH 2 —CHCH 3 ) n —, where n is an integer from 1 to 10.

21. The process of claim 13 , wherein the diol of the formula (I) is bis[2-(2-hydroxyethoxy) ethyl] methanephosphonate.

22. The process of claim 15 , wherein the flame-retardant hot-melt adhesive is a reactive hot-melt adhesive.

23. The process of claim 15 , wherein A and B are identical or different and are mono- or polyalkylene glycol groups, which are ethylene glycol groups of formula —CH 2 —CH 2 (—O—CH 2 —CH 2 ) n — or propylene glycol groups of formula —CH 2 —CHCH 3 (—O—CH 2 —CHCH 3 ) n —, where n is an integer from 1 to 10.

24. The process of claim 15 , wherein the diol of the formula (I) is bis[2-(2-hydroxyethoxy) ethyl] methanephosphonate.

25. The adhesive, sealant or coating of claim 16 , which is a hot-melt adhesive.

26. The adhesive, sealant or coating of claim 25 , which is a reactive hot-melt adhesive.

27. The adhesive, sealant or coating of claim 17 , which is a hot-melt adhesive.

28. The adhesive, sealant or coating of claim 27 , which is a reactive hot-melt adhesive.

Assignments (3)
CHANGE OF NAME Recorded Jan 31, 2020
From: EVONIK DEGUSSA GMBH
To: EVONIK OPERATIONS GMBH
Reel/Frame 051765/0166 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 1, 2015
From: EVONIK INDUSTRIES AG
To: EVONIK DEGUSSA GMBH
Reel/Frame 037174/0982 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 10, 2015
From: DIEHL, CHRISTINA; BRENNER, GABRIELE; SCHLEIMER, BERNHARD
To: EVONIK DEGUSSA GMBH
Reel/Frame 036535/0408 →